IUPAC

Preferred names of co nstitutional units for use in structure - based names of polymers For Peer Review Only

Journal: Pure and Applied Chemistry

Manuscript ID PAC-REC-16-05-02

Manuscript Type: Recommendation

Date Submitted by the Author: 28-May-2016

Complete List of Authors: Mormann, Werner; University of Siegen, Macromolecular Chemistry; Hellwich, Karl-Heinz Chen, Jiazhong Wilks, Edward

IUPAC nomenclature; polymer nomenclature; names of constitutional Keywords: units; names of common polymers

Author-Supplied Keywords:

P.O. 13757, Research Triangle Park, NC (919) 485-8700 Page 1 of 40 IUPAC

1 1 2 3 4 5 6 7 8 Preferred names of constitutional units for use in 9 10 structure-based names of polymers (IUPAC

11 Recommendations 2016) ∗∗∗ 12 13 Werner Mormann 1†, Karl-Heinz Hellwich 2†, Jiazhong Chen 3, Edward S. Wilks 4 14 For Peer Review Only 15 1Makromolekulare Chemie, Universität Siegen, Adolf-Reichwein-Straße 2, 57068 Siegen, 16 2 3 Germany; Postfach 10 07 31, 63007 Offenbach, Germany; DuPont Experimental Station, Rte. 17 141 & Henry Clay Road, Wilmington, DE 19883, USA; 4113 Meriden Drive, Canterbury Hills, 18 Hockessin, DE 19707, USA 19 20 21 ABSTRACT: A list of constitutional units (CU) used for naming polymers according to IUPAC nomenclature rules 22 is provided. This list contains CUs of commercial and wellknown polymers as well as CUs which have been used in 23 polymernomenclaturerelated IUPAC documents. A preferred name is provided for each constitutional unit. Other 24 acceptable names, and names which must not be used because they are outdated or incorrect although they may have 25 been correct in the past or in a different context are also listed. A second table contains names of common polymers: 26 structurebased, sourcebased, retained traditional polymer names and not acceptable names, again because they are 27 outdated or incorrect. These tables supersede similar tables and names in previous documents. The rules given in those 28 documents are still valid but names of constitutional units should be checked for agreement with the present document. 29 The preferred names of constitutional units in Table 1 should be used in structurebased names of regular and irregular 30 polymers. 31 32 KEYWORDS: IUPAC nomenclature; polymer nomenclature; names of constitutional units; names of common 33 polymers 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 ∗ Sponsoring bodies: IUPAC Division of and Structure Representation and IUPAC Polymer 56 Division, SubCommittee on Polymer Terminology: see more details on p. XX. 57 † Corresponding authors: Email: [email protected]siegen.de ; [email protected] 58 59 60 P.O. 13757, Research Triangle Park, NC (919) 485-8700 IUPAC Page 2 of 40

1 2 2 3 4 CONTENTS 5 6 ABSTRACT 7 PNP0 INTRODUCTION 8 PNP1 PRINCIPLES OF STRUCTUREBASED NOMENCLATURE OF POLYMERS 9 PNP2 CONSTITUTIONAL UNITS FOR NAMING POLYMERS 10 PNP3 STRUCTUREBASED, SOURCEBASED AND TRADITIONAL NAMES OF COMMON POLYMERS 11 PNP4 SUMMARY 12 MEMBERSHIP OF SPONSORING BODIES 13 REFERENCES 14 For Peer Review Only 15 PNP-0 INTRODUCTION 16 17 The development of chemical nomenclature for polymeric substances is an ongoing endeavor. Over recent decades, 18 some of the general principles and also details on how to name polymers have undergone changes. Thus, the first IUPAC document on structurebased nomenclature of singlestrand polymers [1] named, for example, the polymer 19 obtained from tetrahydrofuran (oxolane) through cationic polymerization, poly(oxytetramethylene). At that time, 20 polypropylene was a systematic name, the constitutional unit –CH –CH – was named , and the –CH=CH–CH – 21 2 2 2 CH – unit was named 1butenylene to give only few examples of then uptodate nomenclature. As organicchemical 22 2 nomenclature developed, a necessary revision of [1] appeared in 2002 [2]. The “polymethylene” names (e.g., 23 hexamethylene) as well as the alkylene names for constitutional units (e.g., butylene) were abandoned in favour of 24 alkane1, x-diyl and further changes were made to accord with organicchemical nomenclature [3, 4]. Minor revisions of 25 [2] were also made in the 2 nd edition of the Compendium of Polymer Terminology and Nomenclature, “The Purple 26 Book” [5]. Changes in the recently issued new editions of the IUPAC Nomenclature of Organic Chemistry (“The Blue 27 Book”) [6] and Inorganic Chemistry (“The Red Book”) [7] again have implications on naming polymers. 28 There are two principal approaches to naming polymers [5], sourcebased nomenclature and structurebased 29 nomenclature. Sourcebased nomenclature uses the IUPAC names of the monomer or monomers from which the 30 polymer is presumed to have been prepared. Structurebased nomenclature uses IUPAC nomenclature for the 31 constitutional units of the constituent macromolecules. In this document, constitutional units are collated only for 32 structurebased names; for sourcebased names of polymers, the names of units, the monomer units, to be used are those 33 recommended in the IUPAC nomenclature of organic [6] and inorganic [7] chemistry and in the new document on 34 sourcebased nomenclature [8]. 35 Published rules [2, 5] give clear instructions on how to determine constitutional repeating units (CRUs) and the order 36 of their subunits in a regular macromolecule. These rules lead to a single, preferred CRU, i.e., a unique structure 37 (sequence of constitutional units), which is the basis for naming a polymer by structurebased nomenclature. However, 38 for many constitutional units (CUs) there is more than one possibility of naming them which results in a number of 39 different possible structurebased names for a given polymer. These different possibilities have been favoured 40 differently at different times, and have thus been sources of inconsistencies. 41 One principal rule in polymer nomenclature is that the names of constitutional units and monomer units must be those 42 recommended in organicchemical nomenclature. Therefore, in structurebased polymer nomenclature the names of the 43 corresponding groups in organic chemistry should be used for each CU. There should hence seem to be no need to 44 discuss the naming of CUs or CRUs. However, polymer nomenclature has some specific requirements, which in a 45 number of cases will nevertheless lead to a different name. One of these requirements is expressed in the very basic rule used in structurebased nomenclature: groups not constituting the backbone of a macromolecule are always named as 46 . This rule overrides the abovementioned principal rule, which results in the situation that in practice a large 47 number of CRUs will have names that differ from the names that these groups have in organicchemical nomenclature. 48 One example is the group –CH(CH 3)–CH 2–, called propane1,2diyl in organic chemistry. This name is not used in 49 polymer nomenclature because at least with the order of locants (1,2) it would refer to a different orientation of the 50 constitutional unit. If one follows the selection rules for the determination of the preferred CRU the name would have to 51 be propane2,1diyl. More importantly, however, the general rule for naming groups that do not constitute the backbone 52 (here the methyl group) as substituents, leaves a substituted –CH 2–CH 2– group in the backbone. This results in the name 53 1methylethylene for this example, or more systematically, 1methylethane1,2diyl. As with this example, a number of 54 preferred names in the context of organicchemical nomenclature will therefore have to be stated as being incorrect in 55 contexts within polymer nomenclature. However, for each part of the constitutional unit (structure) the corresponding 56 component name should still be that used in organicchemical nomenclature. These principles also apply to the naming 57 of inorganic or hybrid organicinorganic polymers. 58 Another example is the group –CH 2–CH 2–, a very important CU in the naming of polymers, probably being the most 59 60 P.O. 13757, Research Triangle Park, NC (919) 485-8700 Page 3 of 40 IUPAC

1 3 2 3 4 frequently occurring CU in polymer nomenclature. There are two names for this constitutional unit: 5 – the traditional name ethylene and 6 – the systematic name 1,2diyl. 7 The former is in common usage, while in [6] the latter is recommended to be used in a preferred IUPAC name (PIN), 8 the argument being that this name is more systematic. 9 Replacement of the name ethylene with ethane1,2diyl as done in the Purple Book [5] would result in new and 10 longer names for a large number of polymers (in particular polymers of industrial importance) without gaining any 11 advantage. Therefore it is recommended that the preferred name for the group –CH 2–CH 2– in structurebased polymer 12 nomenclature remains ethylene. The unfortunate change of the respective names in the Purple Book [5] was based on 13 the erroneous assumption that the Blue Book [6] would abandon the name ethylene completely. 14 RecommendationsFor in this documentPeer attempt to Reviewremove inconsistencies in structurebased Only polymer nomenclature and 15 aim at making a clear statement as to which of the diverse names of CUs are still recommended and which of several 16 alternative acceptable names is the preferred one. The document is restricted to singlestrand polymers, because the vast 17 majority of polymers have this structural feature. 18 This document consists mainly of tables together with explanatory footnotes and a section on how to use the tables. As the whole document will be searchable, the authors hope that anyone having to deal with polymer nomenclature will 19 use this collection of constitutional units for correctly naming polymers. 20 The preferred names of constitutional units in Table 1 should be used in structurebased names of regular and 21 irregular polymers (e.g., constitutional repeating units, subunits of constitutional repeating units, junction units, and 22 single constitutional units in names of irregular polymers). 23 24 25 PNP-1 PRINCIPLES OF STRUCTURE-BASED NOMENCLATURE FOR POLYMERS 26 The principles of structurebased polymer nomenclature have been described in detail in Refs. [2], [5], [9]and [12] for 27 regular and irregular polymers. Concise versions are given in Refs. [10], [11] and [14]. Depending on how detailed 28 available knowledge of the structure is, the structurebased name of a polymer is long and application of the rules of 29 organicchemical nomenclature in the frame of polymer nomenclature. Examples can be found in the IUPAC 30 recommendations on cyclic organic macromolecules [12]. 31 Regular polymers consist of macromolecules, the structure of which essentially comprises the repetition of a single 32 constitutional unit with all units connected identically with respect to directional sense (definition from Ref. [5], p. 4). In 33 the vast majority of cases regular polymers are idealized structures where irregularities are neglected. 34 A constitutional unit (CU) is an atom or a group of atoms (with pendant atoms or groups, if any) comprising a part of the 35 essential structure of a macromolecule, an oligomer molecule, a regular block, or a regular chain (definition from Ref. 36 [5], p. 5). 37 A constitutional repeating unit (CRU) is the smallest constitutional unit, the repetition of which constitutes a regular 38 macromolecule, a regular oligomer molecule, a regular block, or a regular chain (definition from Ref. [5], p. 5). 39 Structurebased nomenclature of regular polymers uses the name of the preferred CRU. It is determined as follows: 40 (i) a part of the polymer chain large enough to show the structural repetition is drawn, typically, 41 42 CH CH2 O CH CH2 O CH CH2 O 43 Br Br Br 44 (ii) the smallest repeating portion is a CRU so all possibilities in either direction are identified, in this case: 45 CH O CH 46 2 O CH CH2 CHCH2 O 47 Br Br Br 48 49 CH O CH2 CH2 CH O O CH2 CH 50 Br Br Br 51 52 (iii) the next step is to identify the subunits that make up each of these structures, i.e., the largest groups that can be 53 named using IUPAC nomenclature of organic or (when appropriate) inorganic chemistry, 54 55 (iv) the correct order of the subunits, that of decreasing seniority is then determined, then if this leaves a choice 56 57 (v) the preferred CRU is chosen as that with the lowest possible locant(s) for substituents. 58 59 60 P.O. 13757, Research Triangle Park, NC (919) 485-8700 IUPAC Page 4 of 40

1 4 2 3 4 Commonly the preferred CRU of a polymer is written citing its subunits in decreasing order of seniority from left to 5 right, i.e., for the above example as follows: 6 O CH CH2 7 Br 8 Using the CU names of entries 152 and 29 in Table 1 the name of this polymer will then be: 9 poly[oxy(1bromoethylene)]. 10 However, it should be noted that the correct name for the preferred CRU is independent of how the formula is actually 11 drawn: 12 NH C [CH ] and C [CH ] NH 13 2 5 n 2 5 n 14 ForO Peer ReviewO Only 15 Both structural representations are correct, the correct name for both is poly[azanediyl(1oxohexane1,6diyl)] applying 16 the above mentioned rules for determination of the CRU with entries 159 and 93 from Table 1. 17 Irregular polymers consist of macromolecules, the structure of which essentially comprises the repetition of more than 18 one type of constitutional unit or of macromolecules the structure of which comprises constitutional units not all 19 connected identically with respect to directional sense (definition from Ref. [5], p. 4). 20 Irregular polymers are named by placing the prefix “poly” before the structurebased names of the constitutional units, 21 collectively enclosed in parentheses or brackets, with the individual constitutional units separated by oblique strokes. 22 23 A simple example of an irregular polymer is the polymer derived from chloroethene, the units of which are linked both 24 headtotail and headtohead: 25 26 CH CH2 CH CH2 CH2 CH CH CH2 CH2 CH CH2 CH 27 Cl Cl Cl Cl Cl Cl 28 The constitutional units are: 29 CHCH2 and CH2 CH 30 Cl Cl 31 32 The name of the polymer is: poly[(1chloroethylene)/(2chloroethylene)] with entries 32 and 33 from Table 1. 33 For details on structurebased nomenclature of irregular polymers see Ref. [9]. 34 35 PNP-2 CONSTITUTIONAL UNITS FOR NAMING POLYMERS 36 37 Constitutional units (CUs) for naming common polymers (commercial or otherwise wellknown) and CUs that have been used in IUPAC documents on polymer nomenclature and terminology have been identified and collected in Table 38 1. This table includes the chemical formula of each CU and its preferred name, which should be used when naming a 39 polymer. The column headed “Other acceptable names of CU” contains acceptable alternative names. The next column 40 lists names for these CUs, which should no longer be used because they are outdated, ambiguous or incorrect for various 41 reasons, typically: 42 43 – a change of the position of locants in a name, e.g., “but1ene1,4diyl” not “1butene1,4diyl”; 44 – the use of a substituted “ethylene” instead of alkane1,2diyl, e.g., “1methylethylene” not “propane1,2diyl”; 45 – formerly used for different structures, e.g., propylene, 46 – etc. 47 Formulae in Table 1 are drawn with "open" bonds for free valences as common in polymer chemistry when the 48 element symbols of the atoms with the free valences are shown. A wavy line perpendicular to the end of each bond line 49 indicating a free valence of a CU is used in accordance with [22] if any element symbol of an atom with a free valence 50 in this CU is not shown. 51 Names of CUs which are always enclosed in enclosing marks (substituted subunits) are shown with the corresponding 52 enclosing marks in the table. CUs without enclosing marks in Table 1 are not parenthesised in a polymer name except 53 when they constitute the only and complete CRU. 54 55 In Table 1, these names have been arranged to facilitate location of a constitutional unit for the convenience of the 56 reader. Entries are arranged in 6 groups: 57 1. carbon chains according to number of chain atoms and degree of unsaturation; 58 2. carbon rings according to ring size and degree of unsaturation; 59 60 P.O. 13757, Research Triangle Park, NC (919) 485-8700 Page 5 of 40 IUPAC

1 5 2 3 4 3. chains containing hetero atoms; 5 4. heterocycles according to ring size and number and type of hetero atoms; 6 5. spiro units; 7 6. units with connectivity greater than two. 8 Entries within these groups are listed in order of increasing complexity (unsubstituted, mono and multiply 9 substituted, number and size of rings). Structural formulae in most cases are written in decreasing order of seniority of 10 subunits as they will appear in a preferred CRU (see PNP1) when reading from left to right. In some cases (e.g. blocks 11 linked to each other in a particular way, or single [linking] constitutional units, or irregular polymers) a different order 12 or orientation of constitutional units will result, and the name of the corresponding CU in the polymer name will reflect 13 this. Some names that deviate from a name for a preferred CRU (if the polymer is composed of this CU only) are 14 exemplified in entriesFor 33 and 76Peer in Table 1. Review Only 15 Reasons as to why some names of CUs are no longer acceptable are given in the corresponding column or explained 16 in footnotes, which can be found at the end of the table (p. ##). 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60 P.O. 13757, Research Triangle Park, NC (919) 485-8700 IUPAC Page 6 of 40

1 2 3 6 4 5 Table 1 Structure, preferred names, other acceptable names and not acceptable names of constitutional units for naming polymers 6 Footnotes to this table are found at the end of the table on p. ##. 7 8 Document No. Chemical structure of CU Preferred name of CU Other acceptable names of CU Not acceptable names of CU 9 (source) 10 For Peer Review Only [1, 2, 12, 13, 1 CH methanediyl 11 2 14, 15] 12 methylidyne 1, 3) ; 13 2 methanylylidene [2, 12, 13] CH methylylidene 14 15 NH2 3 (aminomethylene) [12] 16 C H 17 Br 18 4 C (bromomethylene) [12] 19 H 20 Cl 21 5 C (chloromethylene) [1, 9, 12] 22 H 23 OCH3 24 C O 25 6 [(2methoxy2oxoethyl)methylene] {[(methoxycarbonyl)methyl]methylene} [2(methoxycarbonyl)ethylidene] 2, 3) [1] 26 CH2 27 C H 28 29 CH3 ethylidene 2, 3); 7 (methylmethylene) [1, 2, 12, 13] 30 C ethane1,1diyl 2 H 31 C H 32 3 7 1,1diyl 2); 8 (propylmethylene) [2] 33 C butylidene 2, 3) 34 H 35 36 9 (phenylmethylene) benzylidene 2, 3) [1, 2, 12, 16] 37 C 38 H 39 CCl3 40 10 C [(trichloromethyl)methylene] [17] 41 H 42 43 44 45 46 P.O. 13757, Research Triangle Park, NC (919) 485-8700 47 48 49 50 51 52 53 54 55 56 57 58 59 60 Page 7 of 40 IUPAC

1 2 3 7 4 CF3 5 6 11 {[3(trifluoromethyl)phenyl]methylene} [2] 7 C H 8 Cl 9 12 C (dichloromethylene) [9] 10 Cl For Peer Review Only 11 F 12 tetrafluoroethylene 3); [1, 2], 14, 13 C (difluoromethylene) 13 (1,1difluoromethylene) 15] 14 F 15 CH3 isopropylidene 2, 3); [2, 13, 14, 16 14 C (dimethylmethylene) 1methylethane1,1diyl 2); 18] propane2,2diyl 2) 17 CH3 18 CF 19 3 C 20 15 [bis(trifluoromethyl)methylene] [13] 21 CF3

22 C6H5 23 16 C (diphenylmethylene) [2] 24 C H 25 6 5 26 CH vinylidene 3, 4); 27 17 2 (methylidenemethylene) [2] ethene1,1diyl 2 28 C 29 30 NH 18 carbonimidoyl (iminomethylene) iminocarbonyl 5) [2, 9] 31 C 32 33 CH3 34 H C CH 19 3 3 (tert butylcarbonimidoyl) [( tert butylimino)methylene] [17] 35 N 36 C 37 38 ({[4(2methylpropan2 39 20 [(4tert butylphenyl)carbonimidoyl] {[(4tert butylphenyl)imino]methylene} [13] 40 yl)phenyl]imino}methylene) 41 42 S 21 carbonothioyl thiocarbonyl [1, 2] 43 C 44 45 46 P.O. 13757, Research Triangle Park, NC (919) 485-8700 47 48 49 50 51 52 53 54 55 56 57 58 59 60 IUPAC Page 8 of 40

1 2 3 8 O [1, 2, 12, 13, 4 22 carbonyl 5 C 16] 6 7 23 CH2 CH2 ethylene ethane1,2diyl [2] 8 [1, 2, 12, 13, 9 24 C C ethene1,2diyl vinylene H H 14] 10 For Peer Review Only 3) 11 25 C C ethenetetrayl ethenediylidene (only for =C=C=) [12] 12 13 26 C C ethanediylidene [2, 12] 14 H H 15 16 27 C C ethynediyl ethyne1,2diyl [13] 17 H 18 C CH2 19 (1acetoxyethane1,2diyl); [1, 2, 9, 14, 28 O (1acetoxyethylene) 20 C O [1(acetyloxy)ethane1,2diyl] 15] 21 CH 22 3 23 H 29 C CH2 (1bromoethylene) (1bromoethane1,2diyl) [1, 2, 14] 24 Br 25 H 26 C CH2 30 (1carbamoylethylene) (1carbamoylethane1,2diyl) [18] 27 C 28 O NH2 29 (1 30 H {[(carboxylatomethyl)dimethylammonio]m 31 C CH (1 2 ethyl}ethylene); 32 31 {[(carboxylatomethyl)dimethylazaniumyl] [13] CH2 (1 33 + – methyl}ethylene) Me2N CH2 COO {[(carboxylatomethyl)dimethylammonio]m 34 ethyl}ethane 1,2 diyl) 35 H 36 [1, 2, 9, 12, 32 C CH2 (1chloroethylene) (1chloroethane1,2diyl) 37 14, 15, 18] Cl 38 39 Preferred CRU of homopolymer: 40 33 (2chloroethylene) (2chloroethane1,2diyl) [9] (1chloroethylene) 41 42 43 44 45 46 P.O. 13757, Research Triangle Park, NC (919) 485-8700 47 48 49 50 51 52 53 54 55 56 57 58 59 60 Page 9 of 40 IUPAC

1 2 3 9 4 H C CH 5 34 2 [1(chloromethyl)ethylene] [1(chloromethyl)ethane1,2diyl] [14] 6 CH2Cl H 7 [1, 2, 9, 14, 35 C CH2 (1cyanoethylene) (1cyanoethane1,2diyl) 8 15] 9 CN 10 36 For(2cyanoethylene) Peer Review (2cyanoethane1,2diyl) Only [9] 11 12 H 13 37 C CH2 (1decylethylene) (1decylethane1,2diyl) dodecane2,1diyl 2) [2] 14 [CH ] CH 15 2 9 3 H 16 38 C CH2 (1fluoroethylene) (1fluoroethane1,2diyl) [1, 2, 14] 17 F 18 H 19 39 C CH2 (1hydroxyethylene) (1hydroxyethane1,2diyl) [1, 2, 9, 14] 20 OH 21 H 22 40 C CH2 (1iodoethylene) (1iodoethane1,2diyl) [1] 23 I 24 H propylene 2); [1, 2, 12, 13, 25 41 C CH2 (1methylethylene) (1methylethane1,2diyl) 26 propane2,3diyl 2 14, 19, 15] CH3 27 preferred CRU of homopolymer: 28 42 (2methylethylene) (2methylethane1,2diyl) [2] 29 (1methylethylene)

30 H 31 C CH2 [1(oxiranyl)ethane1,2diyl]; 43 [1(oxiranyl)ethylene] [18] 32 [1(oxiran2yl)ethane1,2diyl] 33 O 34 H 35 44 C CH2 (sodium 1carboxylatoethylene) (sodium 1carboxylatoethane1,2diyl) [1, 2] – + 36 COO Na 37 H 38 C CH2 [1, 2, 9, 13, benzylidenemethylene 6); 39 45 (1phenylethylene) (1phenylethane1,2diyl) 14, 15, 18, 1phenyldimethylene 40 20] 41 42 43 44 45 46 P.O. 13757, Research Triangle Park, NC (919) 485-8700 47 48 49 50 51 52 53 54 55 56 57 58 59 60 IUPAC Page 10 of 40

1 2 3 10 4 5 preferred CRU of homopolymer: 46 (2phenylethylene) (2phenylethane1,2diyl) [9] 6 (1phenylethylene) 7 8 9 H C CH (1vinylethylene); 10 2 [9, 13, 14, 19 47 CH For(1ethenylethylene) Peer Review(1ethenylethane1,2diyl); Only 18] 11 (1vinylethane1,2diyl) 12 CH2

13 C CH2 14 CH [1(phenylmethylidene)ethylene]; 15 48 (1benzylideneethylene) [13] 16 [1(phenylmethylidene)ethane1,2diyl] 17 18 19 H 20 49 CH2 C (2butylethylene) (2butylethane1,2diyl) [1, 2] 21 [CH2]3 CH3 22 CH3 23 (1{[2carboxylato2 C CH 24 2 (trimethylammonio)ethoxy]carbonyl}1 (1{[2carboxylato2 25 O methylethylene); 50 (trimethylazaniumyl)ethoxy]carbonyl}1 [13] 26 O (1{[2carboxylato2 methylethylene) 27 H2C (trimethylammonio)ethoxy]carbonyl}1 28 + – methylethane1,2diyl) 29 Me3N COO 30 Cl 31 51 C CH2 (1,1dichloroethylene) (1,1dichloroethane1,2diyl) [1] 32 Cl 33 CH3 34 52 C CH (1cyano1methylethylene) (1cyano1methylethane1,2diyl) [1, 16] 35 2 36 CN 37 F [1, 14, 19 38 53 C CH (1,1difluoroethylene) (1,1difluoroethane1,2diyl) 2 15] 39 F 40 CH3 41 [1, 2, 13, 14, 54 C CH (1,1dimethylethylene) (1,1dimethylethane1,2diyl) isobutylene 42 2 16, 15] 43 CH3 44 45 46 P.O. 13757, Research Triangle Park, NC (919) 485-8700 47 48 49 50 51 52 53 54 55 56 57 58 59 60 Page 11 of 40 IUPAC

1 2 3 11 4 CH3 [1(methoxycarbonyl)1methylethane1,2 5 55 C CH2 [1(methoxycarbonyl)1methylethylene] [1, 9, 14] 6 diyl] 7 O OCH3

8 C CH2 9 56 (1oxoethylene) (1oxoethane1,2diyl) [16] O 10 O For Peer Review Only 11 H 12 57 C C (1chloro2oxoethylene) (1chloro2oxoethane1,2diyl) [1, 2] 13 Cl 14 O O ethanedioyl; 15 58 oxalyl [1, 2] C C 1,2dioxoethane1,2diyl 16 17 CH 2 H 18 C C 19 59 (1methylidene2phenylethylene) (1methylidene2phenylethane1,2diyl) [1, 13] 20 21

22 CH CH 23 3 3 60 (1,2dimethylethylene) (1,2dimethylethane1,2diyl) (butane2,3diyl) 2 [2, 19, 17] 24 C C H H 25 C H 26 6 5 S [1oxo2(phenylthio)ethylene]; 27 61 [1oxo2(phenylsulfanyl)ethylene] [1oxo2(phenylsulfanyl)ethane1,2diyl] [1, 2] 28 C C [1oxo2(phenylthio)ethane1,2diyl] H 29 O 30 31 H5C6 C6H5 62 (1,2diphenylethene1,2diyl) [2] 32 C C 33 34 35 63 CH2 CH2 CH2 propane1,3diyl trimethylene 36 37 64 prop1en1yl3ylidene 1propen1yl3ylidene [1, 2] 38 39 40 65 CH CH CH prop2en3yl1ylidene 2propen3yl1ylidene [1, 2] 41 42 43 44 45 46 P.O. 13757, Research Triangle Park, NC (919) 485-8700 47 48 49 50 51 52 53 54 55 56 57 58 59 60 IUPAC Page 12 of 40

1 2 3 12 4 5 66 CH CH2 CH propane1,3diylidene 1,3propanediylidene [1, 2] 6 7 CH CH CH 8 67 2 2 propan1yl3ylidene 9 10 68 CH CH2 CH2 Forpropan3yl1ylidene Peer Review Only [12] 11 12 13 69 (3bromopropane1,3diyl) (3bromotrimethylene) [1] 14 15 Br Cl 16 70 (1bromo3chloropropane1,3diyl) 1bromo3chlorotrimethylene [2] C CH2 C 17 H H 18 Cl 19 71 (1chloropropane1,3diyl) 1chlorotrimethylene [1, 2] C CH2 CH2 20 H 21 D 2 72 [(1 H1)propane1,3diyl] trimethylene1-d [2] 22 C CH2 CH2 23 H 24 73 (2chloropropane1,3diyl) (2chlorotrimethylene) [1, 2] 25 26 27 74 (2hydroxypropane1,3diyl) [18]

28 O 29 75 (1oxopropane1,3diyl) [18] C [CH ] 30 2 2 O O malonyl; preferred CRU in homopolymer: 31 76 propanedioyl [2] 32 C CH2 C (1,3dioxopropane1,3diyl) (1,2dioxopropane1,3diyl) 33 [2, 9, 12, 13, 77 CH CH CH CH butane1,4diyl tetramethylene 34 2 2 2 2 14, 18] 35 36 [1, 2, 9, 13, 78 CH CH CH CH but1ene1,4diyl 1butenylene 37 2 2 14, 18] 38 39 40 79 CH2 CH CH CH2 but2ene1,4diyl 2butenylene [9, 2] 41 42 (1,2dioxotetramethylene); O O succinyl; 43 80 butanedioyl preferred CRU in homopolymer: [1, 13, 14] C CH CH C (1,4dioxobutane1,4diyl) 44 2 2 (1,2dioxobutane1,4diyl) 45 46 P.O. 13757, Research Triangle Park, NC (919) 485-8700 47 48 49 50 51 52 53 54 55 56 57 58 59 60 Page 13 of 40 IUPAC

1 2 3 13 4 (2chlorosuccinyl); 5 81 (2chlorobutanedioyl) preferred CRU in homopolymer: [1, 16] 6 (1,2dioxo3chlorobutane1,4diyl) 7 CH3 CH3 preferred CRU in homopolymer: 8 82 (2,3dimethylbutane1,4diyl) [19] 9 CH2 CH CH CH2 (1,2dimethylbutane1,4diyl) 10 For Peer Review Only 11 83 (1chlorobut1ene1,4diyl) (1chloro1butenylene) [16], 12 13 [1, 2, 14, 15, 84 (1methylbut1ene1,4diyl) 1methyl1butenylene 14 19] 15 16 17 85 (3methylbut1ene1,4diyl) [19] 18 19 20 [3(methoxycarbonyl)4methylbut1ene 86 [19] 21 1,4diyl] 22 23 O O 24 87 butenedioyl fumaroyl ( E), maleoyl ( Z) [2, 13], C CH CH C 25 26 88 CH [CH ] CH pentane1,5diyl pentamethylene [2] 27 2 2 3 2 28 29 89 (2amino4carboxypentane1,5diyl) (2amino4carboxypentamethylene) [1, 2] 30 31 Cl Br (5bromo3chloropentamethylene); 32 90 (5bromo3chloropentane1,5diyl) preferred CRU in homopolymer: [1, 2] CH CH CH CH CH 33 2 2 2 (1bromo3chloropentane1,5diyl) 34 O O glutaryl; preferred CRU in homopolymer: 35 91 pentanedioyl [2] 36 C [CH2]3 C (1,5dioxopentane1,5diyl) (1,2dioxopentane1,5diyl) 37 38 [1, 2, 9, 12, 39 92 CH2 [CH2]4 CH2 hexane1,6diyl hexamethylene 13, 14, 16, 40 18] 41 O 1oxohexamethylene; [1, 2, 13, 14, 42 93 (1oxohexane1,6diyl) hexanoyl (monofunctional) 20] 43 C [CH2]5 44 45 46 P.O. 13757, Research Triangle Park, NC (919) 485-8700 47 48 49 50 51 52 53 54 55 56 57 58 59 60 IUPAC Page 14 of 40

1 2 3 14 4 O O 5 94 (1,3dioxohexane1,6diyl) 1,3dioxohexamethylene [1, 2] C CH2 C CH2 CH2 CH2 6 1,6dioxohexamethylene; 7 O O adipoyl; [1, 2, 9, 13, 95 hexanedioyl preferred CRU in homopolymer: 8 C [CH ] C (1,6dioxohexane1,6diyl) 14, 15] 2 4 (1,2 dioxohexane 1,6 diyl) 9 10 96 CH2 [CH2]6 CH2 For octane1,8diyl Peer Review Only [13] 11 97 C C [CH2]5 CH2 oct1ene1,8diyl [12] 12 H H 13 98 C C [CH ] CH oct1yne1,8diyl [13] 14 2 5 2 15 in case of homopoylmer: 99 (1,3,5,7tetramethyloctane1,8diyl) [19] 16 poly(1methylethylene) 17 100 CH [CH ] CH decane1,10diyl [13] 18 2 2 8 2 19 O O 101 decanedioyl 1,10dioxodecane1,10diyl sebacyl [1, 2, 12, 13] 20 C [CH2]8 C 21 102 CH2 [CH ] CH2 dodecane1,12diyl [13] 22 2 10 7) 1 2 3 4 5 6 7 oxymethyleneoxymethyleneoxymethylenea (1,3,5trioxa7azaheptane1,7diyl) 23 103 [2] 24 O CH2 O CH2 O CH2 NH zanediyl (see oxy, methylene, azanediyl) 25 (1oxa6thia4,9diazanonane)1,9 26 diyl 7); 1 2 3 4 5 6 7 8 9 oxyethyleneazanediylmethylenesulfanediyl 27 104 O CH CH NH CH S CH CH NH oxyethyleneiminomethylenethioethyle [1, 2] 2 2 2 2 2 ethyleneazanediyl 5) 28 neimino ; (see oxy, ethylene, 29 azanediyl, sulfanediyl, methylene) 30 (1,3dioxa8thia5,10 7) 31 diazadodecane1,12diyl) ; oxymethyleneoxymethyleneazanediylethyle 105 O CH O CH NH CH CH S CH NH CH CH oxymethyleneoxymethyleneiminoethy [2] 32 2 2 2 2 2 2 2 nesulfanediylmethyleneazanediylethylene lenesulfanediylmethyleneiminoethyle 33 5) 34 ne 35 36 106 cyclopentane1,2diyl 1,2cyclopentylene [1, 2, 19] 37 O2N 38 {2[2,4dinitrophenyl)hydrazono] 39 H {2[(2,4 1,3cyclopentylene}; N NO2 40 107 N dinitrophenyl)hydrazinylidene]cyclopentan {2[(2,4 [1, 2] 41 e1,3diyl} dinitrophenyl)hydrazono]cyclopentan 42 e1,3diyl} 43 44 45 46 P.O. 13757, Research Triangle Park, NC (919) 485-8700 47 48 49 50 51 52 53 54 55 56 57 58 59 60 Page 15 of 40 IUPAC

1 2 3 15 4 5 108 cyclohexane1,1diyl cyclohexylidene 3) [2, 12] 6 7 8 9 109 cyclohexane1,2diyl [14] 10 For Peer Review Only 11 12 110 cyclohexane1,3diyl 1,3cyclohexylene [1, 2, 14] 13

14 15 111 cyclohexane1,4diyl 1,4cyclohexylene [1, 2, 16] 16 17 112 cyclohex4ene1,3diyl 4cyclohexen1,3ylene [1, 2] 18 19 20 113 (cyclohexa2,5diene1,4diylidene) [2] 21 22 23 114 (6chlorocyclohex1ene1,3diyl) (6chloro1cyclohexen1,3ylene) [1, 2] 24 Cl 25 26 115 tricyclo[2.2.1.0 2,6 ]heptane3,5diyl tricyclo[2.2.1.0 2,6 ]hept3,5ylene [1] 27 28 29 30 116 1,2phenylene 1,2diyl ophenylene 8) [14] 31 32 33 34 117 1,3phenylene benzene1,3diyl mphenylene 8) [2, 9], 14] 35 36 37 [1, 2, 9, 12, 38 118 1,4phenylene benzene1,4diyl pphenylene 8) 13, 14, 16, 39 15] 40 41 42 43 44 45 46 P.O. 13757, Research Triangle Park, NC (919) 485-8700 47 48 49 50 51 52 53 54 55 56 57 58 59 60 IUPAC Page 16 of 40

1 2 3 16 CH3 4 H3C 5 CH 3 (4tert butylbenzene1,2diyl); 6 119 (4tert butyl1,2phenylene) (4tert butylophenylene) 8) [12] 7 [4(1,1dimethylethyl)1,2phenylene] 8 9 10 For Peer Review Only 11 120 (2methyl1,3phenylene) [13] 12 13 14 15 16 121 (4methyl1,3phenylene) [13] 17 18 19 20 122 (4nitro1,3phenylene) [1, 2] 21 NO2 22 23 H3C 24 123 (xmethyl1,3phenylene) [2] 25 26 27 28 29 124 (2phenyl1,3phenylene) (2,6biphenylylene) 2) [1, 2, 16] 30 31 32 33 34 35 36 125 (5phenyl1,3phenylene) biphenyl3,5diyl 2) [2, 16], 37 38 39 40 41 126 (2methyl1,4phenylene) [13] 42 43 44 45 46 P.O. 13757, Research Triangle Park, NC (919) 485-8700 47 48 49 50 51 52 53 54 55 56 57 58 59 60 Page 17 of 40 IUPAC

1 2 3 17 4 5 127 (2methoxy1,4phenylene) [13, 16] 6 7 8 OH 9 O C 10 128 For(2carboxy1,4phenylene) Peer Review Only [13] 11 12 13 14 129 (2chloro1,4phenylene) (2chlorobenzene1,4diyl) (2chloropphenylene) [12] 15 16 17 preferred CRU in homopolymer: 18 130 (3chloro1,4phenylene) [1, 2] (2chloro1,4phenylene) 19

20 21 CH3 22 131 (methylphenylene) [2] 23 24 25 O 26 C 27 132 phthaloyl carbonyl1,2phenylenecarbonyl benzene1,2dicarbonyl 9) [2], [13] 28 C 29 30 O 31 O O 32 133 C C isophthaloyl carbonyl1,3phenylenecarbonyl benzene1,3dicarbonyl 9) [2] 33 34 35 O O [1, 2, 13, 14, 36 134 terephthaloyl carbonyl1,4phenylenecarbonyl benzene1,4dicarbonyl 9) 37 C C 15, 16, 18] 38 39 OH OH 40 O C C O 41 135 (4,6dicarboxy1,3phenylene) [13, 18] 42 43 44 45 46 P.O. 13757, Research Triangle Park, NC (919) 485-8700 47 48 49 50 51 52 53 54 55 56 57 58 59 60 IUPAC Page 18 of 40

1 2 3 18 4 5 6 136 (2,5dioctyl1,4phenylene) [13] 7 8 9 10 For Peer Review Only 11 137 (2,5diamino1,4phenylene) [18] 12 13

14 15 16 17 138 (2,6dimethyl1,4phenylene) [13] 18 19 20 21 22 23 24 139 (2,6diphenyl1,4phenylene) 1,1':3',1''terphenyl2',5'diyl 2) [13] 25 26 27 28 29 H3CO OCH3 30 31 140 (2,3,5,6tetramethoxy1,4phenylene) (tetramethoxy1,4phenylene) [2] 32 33 H3CO OCH3 34 35 4,4'biphenylene; 141 [1,1'biphenyl]4,4'diyl biphenyl4,4'diyl [2] 36 4,4'biphenylylene

37 38 39 142 (3chloro[1,1'biphenyl]4,4'diyl) (3chlorobiphenyl4,4′diyl) (3chloro4,4'biphenylylene) [1, 2] 40 41 42 43 44 45 46 P.O. 13757, Research Triangle Park, NC (919) 485-8700 47 48 49 50 51 52 53 54 55 56 57 58 59 60 Page 19 of 40 IUPAC

1 2 3 19 4 5 6 143 1,4diyl [13] 7 8 9 10 For Peer Review Only 11 144 naphthalene1,5diyl [2] 12 13 14 15 16 145 naphthalene1,8diyl [2] 17 18 19 20 146 naphthalene2,6diyl [2] 21

22 23 2,7naphthylene; 147 naphthalene2,7diyl [1, 2] 24 2,7naphthalenediyl 25 26 27 28 (3'bromo2chloro[1,1':4',1''terphenyl] (3'bromo2chloropterphenyl4,4'' 148 [1, 2] 29 4,4''diyl) ylene) 30 31 32 33 34 149 (5′chloro[1,2′binaphthalene]4,7′diyl) (5'chloro1,2'binaphthyl4,7'ylene) [1, 2] 35 36 Cl 37 38 39 150 acenaphthylene3,7diyl [2] 40 41 42 43 44 45 46 P.O. 13757, Research Triangle Park, NC (919) 485-8700 47 48 49 50 51 52 53 54 55 56 57 58 59 60 IUPAC Page 20 of 40

1 2 3 20 4 5 6 151 acenaphthylene3,8diyl 3,8acenaphthylenylene [1, 2] 7 8 9 [1, 2, 13, 14, 152 O oxy 10 For Peer Review Only 16] 11 12 153 O O peroxy dioxy [2] 13 14 [1, 2, 12, 13, 15 154 S sulfanediyl thio 16 14, 16] 17 18 155 S S disulfanediyl dithio [2, 13] 19 O 20 156 sulfinyl thionyl [1, 2] S 21 O 22 [1, 2, 12, 13, 157 S sulfonyl sulfuryl 23 14] 24 O 25 26 158 Se selanediyl [12] 27 28 [1, 2, 12, 13, 159 H azanediyl imino 11) 29 N 14] 30 OH 31 160 (hydroxyazanediyl) (hydroxyimino) 11) [2] 32 N 33 CH 34 161 3 (methylazanediyl) (methylimino) 11) [1, 2] 12] 35 N

36 CH3 37 11) 162 CH2 (ethylazanediyl) (ethylimino) [14] 38 N 39 40 R 41 163 (alkylazanediyl) (alkylimino) 11) [13] N 42 43 44 45 46 P.O. 13757, Research Triangle Park, NC (919) 485-8700 47 48 49 50 51 52 53 54 55 56 57 58 59 60 Page 21 of 40 IUPAC

1 2 3 21 4 C6H5 5 164 (phenylazanediyl) (phenylimino) 11) [2, 12, 13] 6 N 7 8 9 10 165 For(benzoylazanediyl) Peer Review Only(benzoylimino) 11) [2] 11 C O 12 N 13 14 + 11) 15 166 NH2 azaniumdiyl iminio [2, 13] 16 17 CH3 + 11) 18 167 N (dimethylazaniumdiyl) (dimethyliminio) [1, 2, 13, 16] 19 CH3 20 3) 21 168 N azanylylidene nitrilo [1, 2, 12, 13] 22 23 [1, 2, 13, 14, 169 NH NH hydrazine1,2diyl diazane1,2diyl hydrazo 24 18] 25 26 170 N N diazenediyl azo [2] 27 O 28 171 (1oxidodiazen1ium1,2diyl) (ONN azoxy) [1, 2] 29 N N triazenediyl; 30 172 H triaz1ene1,3diyl triazene1,3diyl [2] 31 N N N azoimino 5) 32 H H iminocarbonylimino ; 33 173 N C N azanediylcarbonylazanediyl ureylene, [13] 10) 34 O carbonylbisazanediyl 35 OC2H5 36 174 P (diethoxyλ5phosphanylylidene) (diethoxyλ5phosphanetriyl) [2] 37 OC H 38 2 5 39 OC2F5 [bis(pentafluoroethoxy)λ5 40 175 P [13] 41 phosphanylylidene] OC2F5 42 43 44 45 46 P.O. 13757, Research Triangle Park, NC (919) 485-8700 47 48 49 50 51 52 53 54 55 56 57 58 59 60 IUPAC Page 22 of 40

1 2 3 22 4 Cl 5 176 P (dichloroλ5phosphanylylidene) [13] 6 Cl 7 177 SiH silanediyl silylene [1, 2, 14] 8 2 9 CH3 10 178 Si For[methyl(phenyl)silanediyl] Peer Review Only(methylphenylsilylene) [2] 11 C6H5 12 CH3 13 [12, 13, 14, 179 Si (dimethylsilanediyl) (dimethylsilylene) 14 21] 15 CH3 16 CH3 17 180 Sn (dimethylstannanediyl) (dimethylstannylene) [9, 13, 21] 18 CH 19 3 20 CH3 21 181 Ge (dimethylgermanediyl) (dimethylgermylene) [13] 22 CH3 23 24 H N 25 182 1Hpyrrole2,5diyl pyrrole2,5diyl [13] 26 27 28 29 183 1Hpyrrole3,4diyl pyrrole3,4diyl [1, 2] 30 N 31 H 32 CH3 33 184 N (1methyl1Hpyrrole2,5diyl) (1methylpyrrole2,5diyl) [13] 34 35 36 37 38 185 (3octyl1Hpyrrole2,5diyl) (3octylpyrrole2,5diyl) [13] 39 40 41 42 43 44 45 46 P.O. 13757, Research Triangle Park, NC (919) 485-8700 47 48 49 50 51 52 53 54 55 56 57 58 59 60 Page 23 of 40 IUPAC

1 2 3 23 4 H N 5 6 186 N (4phenyl1H2,5diyl) (4phenylimidazole2,5diyl) [13] 7 8 9 10 H N For Peer Review Only 11 12 187 N (4phenyl1Himidazole5,2diyl) (4phenylimdiazole5,2diyl) [13] 13 14 15 16 17 18 188 NH (5phenyl1Himidazole4,2diyl) (5phenylimidazole4,2diyl) [13] 19 20 N 21 22 23 24 189 (2,4dioxoimidazolidine1,3diyl) [13] 25 26 27 28 29 190 (2,5dioxoimidazolidine1,3diyl) [13] 30 31 32 H 33 N 34 191 4H1,2,4triazole3,5diyl [1], [2], [16] 35 N N 36 N 37 NO 38 192 1,2,3oxadiazole4,5diyl [13] 39 40 NO 41 193 1,2,4oxadiazole3,5diyl [13, 18] 42 N 43 44 45 46 P.O. 13757, Research Triangle Park, NC (919) 485-8700 47 48 49 50 51 52 53 54 55 56 57 58 59 60 IUPAC Page 24 of 40

1 2 3 24 4 O NN 5 194 1,2,5oxadiazole3,4diyl [13] 6 7 8 NN 9 195 1,3,4oxadiazole2,5diyl [13, 18] 10 O For Peer Review Only 11 N 12 S N preferred CRU in homopolymer: 196 1,2,3thiadiazole5,4diyl [13] 13 1,2,3thiadiazole4,5diyl 14 15 S N 16 preferred CRU in homopolymer: 197 1,2,4thiadiazole5,3diyl [13] 17 N 1,2,4thiadiazole3,5diyl 18 19 S NN 20 198 1,2,5thiadiazole3,4diyl [13] 21 22 23 NN 24 199 1,3,4thiadiazole2,5diyl [13] 25 S 26 27 O 200 2,5diyl [13] 28

29 30 31 201 (2,5dioxooxolane3,4diyl) (2,5dioxotetrahydrofuran3,4diyl) [14, 15] 32 33 34 S 35 202 thiophene2,4diyl [14] 36 37 38 S 39 203 thiophene2,5diyl [13, 14], 40 41 42 43 44 45 46 P.O. 13757, Research Triangle Park, NC (919) 485-8700 47 48 49 50 51 52 53 54 55 56 57 58 59 60 Page 25 of 40 IUPAC

1 2 3 25 4 5 204 (3,4dioctylthiophene2,5diyl) [13] 6 7 8 9 N S 205 ([2,2'bi(1,3thiazole)]4,4'diyl) [13] 10 S N For Peer Review Only 11 12 13 206 N piperidine1,4diyl [2, 12] 14 15 207 piperidine2,4diyl 2,4piperidinediyl [1, 2] 16 HN 17 18 208 piperidine3,5diyl [2, 14] 19 N H 20 21 209 piperidine4,2diyl 4,2piperidinediyl [1, 2] 22 NH 23 24 210 piperidine3,5diylidene [2] 25 N H 26 N 27 211 2,6diyl [13] 28 29 2,4pyridinediyl; 212 pyridine2,4diyl [1, 2] 30 pyridin2,4ylene 31 32 213 pyridine3,5diyl 3,5pyridinediyl [1, 2, 14, 16] 33

34 35 214 pyridine4,2diyl 4,2pyridinediyl [1, 2, 16] 36 37 38 215 NN 1,4diyl [14]

39 40 41 216 morpholine2,6diyl 2,6morpholinediyl [1, 2] 42 43 44 45 46 P.O. 13757, Research Triangle Park, NC (919) 485-8700 47 48 49 50 51 52 53 54 55 56 57 58 59 60 IUPAC Page 26 of 40

1 2 3 26 4 5 217 oxane3,5diyl (tetrahydropyran3,5diyl) [1, 2] 6 O 7 218 1,3dioxane4,6diyl [13] 8 OO 9 10 For Peer Review Only [1, 2, 13, 14, 11 219 (2propyl1,3dioxane4,6diyl) 12 16, 15] 13 14 [1methyl1(3 15 220 sulfonatopropyl)phosphinan1ium3,5 [13] 16 + P - diyl] 17 H3C CH2 CH2 CH2 SO3 18 N N 19 221 1,2,4,5tetrazine3,6diyl [13] 20 NN 21 22 222 [2,3'bipyridine]4,5'diyl (2,3'bipyridine)4,5'diyl [1, 2] 23 N N 24 Cl 25 26 223 (4chloro[3,3'bipyridine]5,5'diyl) [1, 2] 27 N N 28 29 30 224 N quinoline2,4diyl [13] 31 32 33 34 35 225 (2,3dihydro1benzofuran2,3diyl) [17] 36

37 38 (3oxo1,3dihydro2benzofuran1,1 39 226 (3oxo2benzofuran1,1(3 H)diyl) [13] 40 diyl) 41 42 43 44 45 46 P.O. 13757, Research Triangle Park, NC (919) 485-8700 47 48 49 50 51 52 53 54 55 56 57 58 59 60 Page 27 of 40 IUPAC

1 2 3 27 4 5 227 2Hfuro[3,2b]pyran2,6diyl [1, 2] 6 7 O O 8 (1,3,5,7tetraoxo1,2,3,5,6,7 (1,3,5,7tetraoxo5,7dihydrobenzo[1,2 9 228 N N 12) hexahydrobenzo[1,2c:4,5c']dipyrrole2,6 [13, 18] c:4,5c’]dipyrrole2,6(1 H,3 H)diyl) 10 For Peer Reviewdiyl) 12) Only 11 O O 12 H N N (1,5dihydrobenzo[1,2d:4,5 13 229 [13] 14 N N d’]diimidazole2,6diyl) 15 H 16 17 230 10 Hphenoxazine2,8diyl 2,8phenoxazinediyl [1, 16] 18 19 20 231 thianthrene2,8diyl 2,8thianthrenediyl [1, 2] 21 22 23 N N 24 232 [6,6'bi(1,3benzoxazole)]2,2'diyl [13] O O 25 26 27 N N 233 [6,6'bi(1,3benzothiazole)]2,2'diyl [13] 28 S S 29 30 31 234 HN NH 1H,1' H[5,5'bibenzimidazole]2,2'diyl [5,5'bibenzimidazole]2,2'diyl [13] 32 N N 33 O 34 O (1,1′,3,3′tetraoxo[5,5′biisoindoline]2,2′ 35 235 N N [2] 36 diyl) 37 O O 38 [6,6'biquinoline]3,3'diyl; 39 236 [3,3'biquinoline]6,6'diyl [1, 2] (3,3'biquinoline)6,6'diyl 40 N N 41 42 43 44 45 46 P.O. 13757, Research Triangle Park, NC (919) 485-8700 47 48 49 50 51 52 53 54 55 56 57 58 59 60 IUPAC Page 28 of 40

1 2 3 28 4 5 6 237 (3,3'diphenyl[6,6'biquinoxaline]2,2'diyl) [13] 7 8 9 10 238 Forspiro[3.5]nona2,5diene7,1diyl Peer Review Onlyspiro[3.5]nona2,5dien7,1ylene [1, 2] 11 12 13 239 spiro[4.5]decane2,8diyl spiro[4.5]dec2,8ylene [1, 2, 16] 14 O 15 240 (5oxaspiro[3.5]nonane2,7diyl) (5oxaspiro[3.5]non2,7ylene) [1] 16 17 (2,4,8,10tetraoxaspiro[5.5]undecane3,9 18 241 [2] diyl) 19 20 (2,4,8,10tetraoxaspiro[5.5]undecane 21 242 [18] 3,3,9,9tetrayl) 22 23 24 243 C methanetriyl [12] H 25 26 244 C methanetetrayl [12] 27 28 29 245 N nitrilo azanetriyl

30 31 246 Ge germanetetrayl [12] 32 33 34 35 247 benzene1,3,5triyl 1,3,5benzenetriyl [2, 12] 36

37 38 248 piperidine1,2,6triyl [12] 39 N 40 41 N 42 249 quinoxaline2,3:6,7tetrayl [13] 43 N 44 45 46 P.O. 13757, Research Triangle Park, NC (919) 485-8700 47 48 49 50 51 52 53 54 55 56 57 58 59 60 Page 29 of 40 IUPAC

1 2 3 29 4 N N (10oxo3,10dihydroimidazo[4,5 5 (10oxoimidazo[4,5f]isoindolo[2,1 6 250 f]isoindolo[2,1a]benzimidazole [13] N N a]benzimidazole2,3(10 H):7,8tetrayl) 12) 7 2,3:7,8tetrayl) 8 O 9 10 1. Methylidyne is the name of the group H–CFor≡ with a carbon triplePeer bond. Review Only 11 2. Name is no longer used for CRUs, because side groups must be treated as substituents. 12 3. Name refers to a different structure. 13 4. Vinylidene is the name of the group CH 2=C= (ethenylidene). 14 5. Iminocarbonyl is a former name for the constitutional unit –NH–CO–, the correct name is azanediylcarbonyl. 15 6. Ambiguous because it is also used for different structure. 16 7. In IUPAC organicchemical nomenclature ‘a’ nomenclature is applicable for heterochains containing 4 or more heteroatom units (see P51.4.1.1 [6]). CRUs of the type shown in entries 103– 17 105 have been used in [2] for demonstration of seniority of units and heteroatoms. Names based on ‘a’ nomenclature were given as additional names in that document. Such units are highly 18 unlikely to occur as CRUs in real regular polymers or as constitutional units in irregular polymers. The use of ‘a’ nomenclature for acyclic components is not acceptable in polymer 19 nomenclature. 8. The letters o, m, and p as locants have been in use for ortho , meta , and para , respectively, to designate the 1,2, 1,3, and 1,4 isomers of disubstituted benzene. This usage is no longer retained 20 in IUPAC nomenclature (P14.3.1 [6]). 21 9. All constitutional units within the polymer backbone must be named consecutively. 22 10. Multiplicative operations cannot be used to name subunits for a C(R)U because all constitutional units within the polymer backbone must be named consecutively. 23 11. The traditional name for both the groups >NH (or –NH–) and =NH has been imino. As these names can lead to ambiguity the name of –NH– in agreement with [6] is azanediyl, the name of 24 =NH remains imino. 25 12. Hydro prefixes have not been alphabetised together with prefixes since 1993, but placed after the substituent prefixes right at the beginning of the modified parent hydride name, see 26 R4.1, Note 49 [3] and P31.2.1 [6]. 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 P.O. 13757, Research Triangle Park, NC (919) 485-8700 47 48 49 50 51 52 53 54 55 56 57 58 59 60 IUPAC Page 30 of 40

1 30 2 3 4 5 PNP-3 STRUCTURE-BASED, SOURCE-BASED AND TRADITIONAL NAMES OF COMMON 6 POLYMERS 7 8 A number of common polymers, in addition to structurebased names have sourcebased names and semisystematic or 9 trivial names that are well established by usage because they are also used for regulatory purposes. So a change to a 10 correct structure or sourcebased name would require changes in many official and legal documents. The most 11 important of these names are included in the following table. In general, however, the use of semisystematic or trivial 12 names for polymers should be kept to a minimum. In particular ambiguous names or names not based on any systematic 13 type of nomenclature should not be used at all. 14 The followingFor Table 2 contains Peer idealized structural Review representations, structurebased Only names and sourcebased names. 15 Equivalent names for close analogues of these polymers [e.g., other alkyl analogues of poly(methyl acrylate) or 16 ester analogues of poly(vinyl )] are also acceptable as long as the alkyl and acid names, respectively, are retained names [6]. Further, Table 2 contains a limiting list of retained traditional polymer names. 17 The terminology used in this context is mainly derived from usage in the socalled IUPAC “Blue Book”, 18 “Nomenclature of Organic Chemistry” [6]. The relevant terms and their meanings are given in the following. 19 20 Preferred IUPAC name (PIN) 21 A name preferred among two or more names generated from two or more IUPAC recommendations including the many 22 synonyms that have been coined and used over the years. 23 General IUPAC nomenclature 24 The principles, rules, and conventions by which IUPAC names other than preferred IUPAC names (PINs) are generated. 25 26 Retained name A traditional or a name in common use either as the preferred IUPAC name or as an alternative name in general IUPAC 27 nomenclature. 28 29 In addition, the following term is important in the context of classifying polymer names. 30 Traditional name 31 A name in common use within one or more sectors of the chemical community. 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60 P.O. 13757, Research Triangle Park, NC (919) 485-8700 Page 31 of 40 IUPAC

1 2 3 31 4 Table 2: Structure-based, source-based and traditional names of common polymers 5 PIN = preferred IUPAC name; 6 bold face type = preferred amongst several sourcebased polymer names; 7 footnotes to this table are found at the end of the table on p. ##. 8 9 10 1) Retained traditional No longer acceptable Polymer structure For Structure-based Peer polymer name Review Source-based polymer name Only 2) 11 polymer name polymer names 12 CH 3) 13 2 n poly(methylene) polyethene polyethylene (PIN) 14 3) 15 CF2 poly(difluoromethylene) poly(tetrafluoroethene) polytetrafluoroethylene n 16 H CH 17 C 2 n poly(1methylethylene) polypropene polypropylene 18 CH3 19 H CH 20 C 2 n poly(1ethylethylene) poly(but1ene) polybutylene 21 CH2 CH3 22 H poly(allyl alcohol), C CH2 n poly[1(hydroxymethyl)ethylene] 23 poly(prop2en1ol) 24 CH2OH 25 H C CH 26 2 n poly[1(methoxycarbonyl)ethylene] poly(methyl acrylate) 27 O OCH3 28 H polyacrylonitrile, 29 C CH2 poly(1cyanoethylene) n poly(prop2enenitrile) 30 CN 31 H C CH polyacrylamide, 32 2 n poly(1carbamoylethylene) 33 poly(prop2enamide) O NH2 34 poly(vinyl chloride) , 35 H C CH2 poly(1chloroethylene) poly(chloroethene), 36 n Cl poly(ethenyl chloride), 37 H poly(vinyl ) , 38 CH C 2 n poly(1fluoroethylene) poly(ethenyl fluoride), 39 F poly(fluoroethene) 40 41 42 43 44 45 46 P.O. 13757, Research Triangle Park, NC (919) 485-8700 47 48 49 50 51 52 53 54 55 56 57 58 59 60 IUPAC Page 32 of 40

1 2 3 32 4 H poly(vinyl alcohol) , C CH2 poly(1hydroxyethylene) 5 n poly(ethenol) 6 OH 7 H C CH2 8 n poly(1acetoxyethylene), poly(vinyl acetate) , O C CH 9 3 poly[1(acetyloxy)ethylene] poly(ethenyl acetate) O 10 H For Peer Review Only 11 C CH2 polystyrene , 12 n poly(1phenylethylene) poly(ethenylbenzene), 13 poly(vinylbenzene) 14 15 H 16 C CH2 n poly(9vinyl9Hcarbazole) poly( Nvinylcarbazole), 17 N poly[1(9 Hcarbazol9yl)ethylene] poly(9vinylcarbazole) 18 poly(9ethenyl9Hcarbazole) poly(vinylcarbazole) 19 20 CH3 poly(2methylpropene), 21 C CH2 poly(1,1dimethylethylene) polyisobutene polyisobutylene n poly(2methylprop1ene) 22 CH3 23 CH3 24 poly[1(methoxycarbonyl)1 C CH2 poly(methyl methacrylate) 25 n methylethylene] 26 O OCH3 27 CH3 28 polymethacrylamide, C CH2 poly(1carbamoyl1methylethylene) 29 n poly(2methylprop2enamide) 30 O NH2 31 Cl 32 C CH2 poly(1,1dichloroethylene) poly(1,1dichloroethene) poly(vinylidene chloride) 33 n Cl 34 35 F 36 C CH2 n poly(1,1difluoroethylene) poly(1,1difluoroethene) poly(vinylidene fluoride) 37 F

38 CH3 39 C CH2 poly[(isopropenyl)benzene], n poly(1methyl1phenylethylene) poly(αmethylstyrene) 40 poly[(prop1en2yl)benzene] 41 42 43 44 45 46 P.O. 13757, Research Triangle Park, NC (919) 485-8700 47 48 49 50 51 52 53 54 55 56 57 58 59 60 Page 33 of 40 IUPAC

1 2 3 33 4 poly(chlorotrifluoroethylene), CClF CF2 poly(chlorotrifluoroethene) polychlorotrifluoroethylene 5 n poly(1chloro1,2,2trifluoroethylene) 6 4) CH CH polyacetylene , 7 n poly(ethene1,2diyl) 8 polyethyne C CH 9 n poly(1methylethene1,2diyl) polypropyne polymethylacetylene 10 CH3 For Peer Review Only 11 poly(but1ene1,4diyl) 12 1,4-polymerization 5) 13 H poly(1vinylethylene), poly(buta1,3diene) polybutadiene C CH 14 2 n poly(1ethenylethylene) 15 HC CH2 1,2 -polymerization 16 poly(1methylbut1ene1,4diyl)

17 1,4-polymerization 18 CH3 poly(1ethenyl1methylethylene), 19 C CH 2 n poly(1methyl1vinylethylene) 20 5) HC polyisoprene , CH 1,2-polymerization 21 2 poly(2methylbuta1,3 diene) 22 poly[1(1methylethenyl)ethylene], H poly[1(1methylvinyl)ethylene], 23 C CH2 24 n poly(1isopropenylethylene), C CH 25 H2C 3 poly[1(prop1en2yl)ethylene] 26 3,4-polymerization poly(1chlorobut1ene1,4diyl) 27 28 1,4-polymerization 29 Cl poly(1chloro1ethenylethylene), C CH 30 2 n poly(1chloro1vinylethylene) 31 CH 1,2- polymerization poly(2chlorobuta1,3diene) polychloroprene H2C 32 H poly[1(1chloroethenyl)ethylene], 33 C CH 2 n poly[1(1chlorovinyl)ethylene] 34 C Cl 3,4-polymerization 35 H2C 36 poly(cyclopent4ene1,3diylethene1,2 diyl) 37 poly(bicyclo[2.2.1]hepta2,5 for linear polymer (ROMP) – other poly(norbornadiene) 38 diene) n 39 polymerization methods usually give a network poly mer 40 41 42 43 44 45 46 P.O. 13757, Research Triangle Park, NC (919) 485-8700 47 48 49 50 51 52 53 54 55 56 57 58 59 60 IUPAC Page 34 of 40

1 2 3 34 4 5 poly(bicyclo[2.2.1]heptane2,3diyl) 6 poly(bicyclo[2.2.1]hept2ene), n poly(norbornene) 7 poly(cyclopentane1,3diylethene1,2diyl) poly(8,9,10trinorborn2ene) 8 ring opening metathesis polymerization n 9 (ROMP) 10 polyformaldehyde , O CH2 Forpoly(oxymethylene) Peer Review Only 11 n polymethanal 12 O CH polyacetaldehyde , 13 n poly[oxy(methylmethylene)] CH polyethanal 14 3 O CH poly(trichloroacetaldehyde), 15 n poly{oxy[(trichloromethyl)methylene]} polychloral 16 CCl3 poly(trichloroethanal) poly(), 17 poly(oxirane) , poly() 18 OCH2 CH2 poly(oxyethylene) polyethylene oxide, n poly(ethene oxide) 19 polyethylene glycol poly(propylene glycol), 20 O CH CH2 poly(2-methyloxirane) , 21 n poly[oxy(1methylethylene)] poly(propylene oxide) polypropylene oxide, CH3 poly( oxide) 22 polypropylene glycol OCH CH 23 2 n poly(2-phenyloxirane) , 24 poly[oxy(1phenylethylene)] poly(phenyloxirane), 25 poly(styrene oxide) 26 poly(trimethylene ether 27 poly(oxypropane1,3diyl) poly(oxetane) glycol), 28 polyoxetane 29 poly(tetramethylene ether 30 poly(oxolane) , poly(oxybutane1,4diyl) glycol), 31 polytetrahydrofuran 32 poly(tetramethylene oxide) 33 34 CH3 poly(lactic acid) OC C poly[oxy(1methyl2oxoethylene)] poly(2hydroxypropanoic acid), 35 H n 36 O poly(3methyloxiran2one) 37 poly(oxolan-2-one) , 38 OC [CH2]3 n poly[oxy(1oxobutane1,4diyl)] poly(butano4lactone), poly( γbutyrolactone) 39 O poly(4hydroxybutanoic acid) 40 OC [CH ] poly(oxepan-2-one) , 41 2 5 poly[oxy(1oxohexane1,6diyl)] poly( εcaprolactone) polycaprolactone n poly(hexano6lactone) 42 O 43 44 45 46 P.O. 13757, Research Triangle Park, NC (919) 485-8700 47 48 49 50 51 52 53 54 55 56 57 58 59 60 Page 35 of 40 IUPAC

1 2 3 35 4 CH3 poly[oxy(dimethylsilanediyl)], 5 O Si poly(dimethylsiloxane) poly[oxy(dimethylsilylene)] n catena poly[(dimethylsilicon)µoxido] 6) 6 CH3 7 CH3 poly[azanylylidene(diethoxyλ5 8 N P poly(diethoxyphosphazene) 9 n phosphanylylidene)] CH3 10 O ForO Peer Review Only 11 O [CH2]2 O C C poly(oxyethyleneoxyterephthaloyl) poly(ethylene terephthalate) 12 n 13 O O poly(propane1,3diyl poly(trimethylene 14 poly(oxypropane1,3diyloxyterephthaloyl) O [CH2]3 O C C terephthalate) terephthalate) 15 n O O 16 poly(oxybutane1,4diyloxyterephthaloyl) poly(butane1,4diyl poly(butylene O [CH2]4 O C C 17 n terephthalate) terephthalate) 18 19 O poly[oxy(1,4phenylene)] polyphenol poly(1,4phenylene oxide) poly(phenylene oxide) 7) n 20 H C 21 3 poly(2,6dimethyl1,4 22 O 7) n poly[oxy(2,6dimethyl1,4phenylene)] poly(2,6dimethylphenol) poly(phenylene oxide) 23 phenylene oxide) 24 H3C O 25 poly(oxy1,4phenylenecarbonyl1,4

26 O C phenylene) n 27 O CH3 poly[oxycarbonyloxy1,4 28 poly[(dimethylmethylene)bis(4,1 O C O phenylene(dimethylmethylene)1,4 29 phenylene) ] CH3 n phenylene] 30 polybenzenethiol, 31 S poly(sulfanediyl1,4phenylene) poly(thiophenol) n poly(1,4phenylene sulfide) 32 33 NHCH2 CH2 poly(azanediylethylene) poly(aziridine) polyethylenimine n 34 poly[imino(1oxopropane CH polyalanine , 35 3 1,2diyl)], NHC C poly[azanediyl(1methyl2oxoethylene)] poly(2aminopropanoic acid), 36 H n poly[imino(1methyl2 O poly(3methylaziridin2one), 37 oxoethylene)] 38 poly(pyrrolidin-2-one) , poly( γbutyrolactam), NHC [CH2]3 39 n poly[azanediyl(1oxobutane1,4diyl)] poly(4aminobutanoic acid), poly[imino(1oxobutane 40 O poly(butano 4lactam) 1,4 diyl)] 41 42 43 44 45 46 P.O. 13757, Research Triangle Park, NC (919) 485-8700 47 48 49 50 51 52 53 54 55 56 57 58 59 60 IUPAC Page 36 of 40

1 2 3 36 4 poly(azepan-2-one) , polycaprolactam, NHC [CH2]5 5 n poly[azanediyl(1oxohexane1,6diyl)] poly(6aminohexanoic acid), poly( εcaprolactam) poly[imino(1oxohexane O 6 poly(hexano 6lactam) 1,6 diyl)] 7 O O poly(azanediyl1,4 poly[ N,N’(1,4 NH NH C C 8 n phenyleneazanediylterephthaloyl) phenylene)terephthalamide] 9 O O poly(azanediyl1,3 10 poly[ N,N’(1,3 NH NH C ForC Peer Review Only 11 n phenyleneazanediylisophthaloyl) phenylene)isophthalamide] 12 poly(azanediyladipoylazanediylhexane1,6 poly[ N,N’(hexane1,6 13 O O poly(hexamethylene diyl), diyl)hexanediamide], 14 NH C [CH ] C NH [CH ] 2 4 2 6 poly(azanediylhexanedioylazanediylhexane poly[ N,N’(hexane1,6 adipamide) 15 n 1,6diyl) diyl)adipamide] 16 poly[(butane1,4diol)alt (1,3 17 O O poly[oxybutane1,4 diisocyanato2methylbenzene)], 18 O[CH]4 O C NH NH C diyloxycarbonylazanediyl(2methyl1,3 poly[(butane1,4diol)alt (2,6 19 CH n phenylene)azanediylcarbonyl] 3 diisocyanatotoluene)] 20 poly[(1,4diisocyanatobenzene) 21 O O poly(oxyhexane1,6 alt (hexane1,6diol)], 22 O [CH]6 O C NH NHC diyloxycarbonylazanediyl1,4 poly[hexane1,6diyl N,N’(1,4 23 n phenyleneazanediylcarbonyl) phenylene)dicarbamate] 24 CH 25 3 Si poly[methyl(phenyl)silylen 26 n poly[methyl(phenyl)silanediyl], 6) poly[methyl(phenyl)silane] 27 catena poly[methyl(phenyl)silicon] e] 28 29 O O O 30 CH CH2 poly[(2,5dioxotetrahydrofuran3,4diyl)(1 poly[(maleic anhydride)alt n 31 phenylethylene)] styrene] 32 33

34 CH2 n poly[(2methyl1,3dioxane4,6 35 OO poly( divinyl acetal) poly(vinyl acetal) polyvinyl acetal 8) 36 diyl)methylene] CH 37 3 38 CH2 n poly[(2propyl1,3dioxane4,6 39 OO poly(butanal divinyl acetal) poly(vinyl butyral) 40 diyl)methylene] CH -CH -CH 41 2 2 3 42 43 44 45 46 P.O. 13757, Research Triangle Park, NC (919) 485-8700 47 48 49 50 51 52 53 54 55 56 57 58 59 60 Page 37 of 40 IUPAC

1 2 3 37 4 CH 2 n 5 poly(1,3dioxane4,6diylmethylene) poly( divinyl acetal) poly(vinyl formal) OO 6 CH3 poly[(1,1’ 7 diyl)(dimethylsilanediyl)], Si poly[1,1’ 8 catena poly{[1,1’bis( η5 CH3 Fe (dimethylsilanediyl)ferrocene] 9 cyclopentadienyl)iron]µ 10 n For(dimethylsilicon)} Peer6) Review Only 11 12 1) Structurebased polymer names based on ‘ethylene’ are preferred to the equivalent names for such constitutional units based on ‘ethane1,2diyl’, which are also 13 acceptable. It should be kept in mind, however, that substituents in substituted ethane1,2diyl must have locants. 14 15 2) Because of their widespread use within industry and academia a limited number of wellestablished traditional names of homopolymers are retained. These are found in 16 this column.

17 3) The formulae –[CH 2CH 2]n– and –[CF 2CF 2]n– are more often used; they are acceptable due to past usage and also an attempt to retain some similarity to the formulae of 18 homopolymers derived from other ethene derivatives. 19 4) Polyacetylene is the sourcebased name of poly(ethene1,2diyl) and also a class name. [13] 20 21 5) Polybutadiene (polyisoprene) can be used as name for a polymer made from butadiene (isoprene), if the structure is not known. 22 6) Name according to the rules for linear inorganic polymers. Similar names are adopted for other polysiloxanes, polysilanes and their analogues. [21] 23 24 7) Poly(phenylene oxide) was originally a trade name for poly(2,6dimethyl1,4phenylene oxide) that was accepted into common usage. As it indicates a nonsubstituted 25 ring system it is a misnomer and its use is therefore not acceptable. 26 8) Polyvinyl acetal is a class name. 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 P.O. 13757, Research Triangle Park, NC (919) 485-8700 47 48 49 50 51 52 53 54 55 56 57 58 59 60 IUPAC Page 38 of 40

1 Project # 2008-015-1-800 draft for SPT, Divisions IV and VIII 2 3 4 5 PNP-4 SUMMARY 6 7 A number of existing IUPAC recommendations on polymer nomenclature and terminology have been screened in 8 terms of naming and names of polymers. From these, a list of constitutional units (CU) used for naming polymers 9 according to IUPAC nomenclature rules has been made (PNP2). This list comprises also CUs of commercial and well 10 known polymers. A preferred name is provided for each CU. Other acceptable names, and names which are not 11 acceptable because they are outdated or ambiguous or incorrect, although they may have been correct in the past or in a 12 different context, are also listed. In a second table (PNP3) names of common polymers are given. This table includes 13 structurebased names, sourcebased names, retained traditional polymer names and not acceptable names. These tables 14 replace similar tablesFor in previous Peer documents. The Reviewpreferred names of constitutional Only units in Table 1 should be used in 15 structurebased names of regular and irregular polymers. It is hoped that in the printed version of this document, entries 16 of tables can be searched by the functions provided in programs for reading pdffiles; this should enable or facilitate 17 construction of names using the names for CUs and common polymers given in the tables.

18 19 20 MEMBERSHIP OF SPONSORING BODIES 21 Membership of the Division Committee of the IUPAC Division of Chemical Nomenclature and Structure 22 Representation for the period 2016–2017 was as follows: 23 24 President : K.H. Hellwich (Germany); Vice President : A. T. Hutton (South Africa); Secretary : R. S. Laitinen 25 (Finland); Titular Members : O. Achmatowicz (Poland); T. Damhus (Denmark); P. Hodge (UK); R. Macaluso (USA); 26 27 J. Nagy (Hungary); M. M. Rogers (USA); J. Vohlídal (Czech Republic); Associate Members : M. A. Beckett (UK); I. 28 L. Dukov (Bulgaria); G. A. Eller (Austria); E. Mansfield (USA); K. T. Taylor (USA); National Representatives : F. 29 Aricó (Italy); H. W. Lee (Korea); T. L. Lowary (Canada); E. Nordlander (Sweden); M. Putala (Slovakia); A. P. Rauter 30 31 (Portugal); J. P. van Lune (Netherlands); A. Yerin (Russia); Ex Officio : R. M. Hartshorn (New Zealand); G. P. Moss 32 (UK). 33 34 Membership of the IUPAC Polymer Division Committee for the period 2016–2017 was as follows: 35 36 President : G. T. Russell (New Zealand); Vice President : C. K. Luscombe (USA); Secretary : M. G. Walter (USA); Past 37 President : M. Buback (Germany); Titular Members : S. Beuermann (Germany); J. He (China); I. Lacík (Slovakia); 38 39 M. Sawamoto (Japan); N. Stingelin (UK); Y. Yagci (Turkey); Associate Members : R. C. Hiorns (France); M. Hess 40 (Germany); R. Hutchinson (Canada); G. Moad (Australia); R. Advincula (USA); D. Auhl (Netherlands); National 41 Representatives : R. Adhikari (Nepal); M. C. H. Chan (Malaysia); C. dos Santos (Brazil); V. P. Hoven (Thailand); C.S. 42 43 Hsu (Taiwan); R. G. Jones (UK); D. S. Lee (Korea); M. Malinconico (Italy); O. Philippova (Russia); J. Vohlídal (Czech 44 Republic 45 46 47 Membership of the Subcommittee on Polymer Terminology during the preparation of this document (2008–2016) was 48 49 as follows: Chair: R. G. Jones (UK), 2006–2013; R. C. Hiorns (France), from 2014; Secretary: T. Kitayama (Japan), 50 2008–2009; R. C. Hiorns (France), 2010–2013; C. K. Luscombe (USA), 2014–2015; P. D. Topham (UK), from 2016; 51 Members: R. Adhikari (Nepal); G. Allegra (Italy); M. Barón (Argentina); R. Boucher (UK); T. Chang (Korea); J. Chen 52 53 (USA); C. Fellows (Australia); A. Fradet (France); K. Hatada (Japan); J. He (China); K.H. Hellwich (Germany); 54 M. Hess (Germany); R. C. Hiorns (France); P. Hodge (UK); K. Horie ‡ (Japan); A. D. Jenkins (UK); J.I. Jin (Korea); 55 56 R. G. Jones (UK); J. Kahovec (Czech Republic); T. Kitayama (Japan); P. Kratochvíl (Czech Republic); P. Kubisa 57 (Poland); C. K. Luscombe (USA); E. Maréchal ‡ (France); S. V. Meille (Italy); I. Meisel (Germany); W. V. Metanomski ‡ 58 59 60 38 P.O. 13757, Research Triangle Park, NC (919) 485-8700 Page 39 of 40 IUPAC

1 Project # 2008-015-1-800 draft for SPT, Divisions IV and VIII 2 3 4 (USA); I. Mita ‡ (Japan); G. Moad (Australia); W. Mormann (Germany); N. Nakabayashi (Japan); T. Nakano (Japan), 5 C. K. Ober (USA); S. Penczek (Poland); M. D. Purbrick (UK); L. P. Rebelo (Portugal); M. Rinaudo (France); G. 6 ‡ 7 Russell (New Zealand); C. dos Santos (Brazil); I. Schopov (Bulgaria); C. Scholz (USA); F. Schué (France); V. P. 8 Shibaev (Russia); S. Słomkowski (Poland); D. W. Smith (USA), R. F. T. Stepto ‡ (UK); N. Stingelin (UK); D. Tabak 9 10 (Brazil); P. D. Topham (UK); J.P. Vairon (France); M. Vert (France); J. Vohlídal (Czech Republic); M. G. Walter 11 (USA); E. S. Wilks (USA); W. J. Work (USA). 12 13 ‡ = Deceased 14 For Peer Review Only 15 16 REFERENCES 17 18 1 IUPAC. “Nomenclature of regular singlestrand organic polymers (IUPAC Recommendations 1975)”, Pure Appl. 19 Chem. 48 , 373–385 (1976). 20 21 2 IUPAC, “Nomenclature of regular singlestrand organic polymers (IUPAC Recommendations 2002)”, Pure Appl. 22 Chem. 74 , 1921–1956 (2002). (Ref. 5, chapter 15) 23 3 IUPAC. “A Guide to IUPAC Nomenclature of Organic Compounds (Recommendations 1993)”, R. Panico, W. H. 24 Powell, J.C. Richer (Eds.), Blackwell Scientific Publications, Oxford (1993); for corrections see [4]. 25 4 IUPAC, “Corrections to A Guide to IUPAC Nomenclature of Organic Compounds ”, Pure Appl. Chem . 71 , 1327– 26 1330 (1999). 27 28 5 IUPAC. Compendium of Polymer Terminology and Nomenclature (Recommendation 2008), R. G. Jones, J. 29 Kahovec, R. Stepto, E. S. Wilks, M. Hess, T. Kitayama, W. V. Metanomski (Eds.), RSC Publishing, Cambridge, UK 30 (2008). 31 6 IUPAC. “Nomenclature of Organic Chemistry (IUPAC Recommendations and Preferred Names 2013)”, H. A. 32 Favre, W. H. Powell (Eds.), XLIII, 1568 p, RSC Publishing, Cambridge, UK, (2014), ISBN: 9780854041824; a 33 list of errata can be found on the web at the address http://www.chem.qmul.ac.uk/iupac/bibliog/BBerrors.html. 34 7 “Nomenclature of Inorganic Chemistry” (IUPAC Recommendations 2005), N. G. Connelly, T. Damhus, R. M. 35 Hartshorn, A. T. Hutton (Eds.), RSC Publishing, Cambridge, UK, 2005, ISBN: 0854044388. 36 37 8 IUPAC, “Sourcebased Nomenclature for Singlestrand Homopolymers and Copolymers (IUPAC Recommendations 38 2015)” Pure Appl. Chem. to be inserted. 39 9 IUPAC, “StructureBased Nomenclature for Irregular SingleStrand Organic Polymers (IUPAC Recommendations, 40 1994)”, Pure Appl. Chem. 66 , 873–889 (1994). (Ref. 5, chapter 17) 41 42 10 IUPAC “A brief guide to polymer nomenclature (IUPAC Recommendations 2012)”, Pure Appl. Chem. 84 , 2167– 43 2169 (2012). 44 11 Principles of Chemical Nomenclature A guide to IUPAC Recommendations, 2011 Edition, G. J. Leigh (Ed.) XII, 45 257 pp. RSC Publishing, Cambridge (2011). 46 12 IUPAC, “Structurebased nomenclature for cyclic organic macromolecules (IUPAC Recommendations 2008)”, Pure 47 Appl. Chem ., 80 , 201–232 (2008). 48 49 13 IUPAC, “Glossary of Class Names of Polymers (IUPAC Recommendations 2009)”, Pure Appl. Chem. 81 , 1131– 50 1186 (2009). 51 14 IUPAC, “Guide for the Authors of Papers and Reports in Polymer Science and Technology” (pdf June 2001). This 52 guide is outofdate. http://old.iupac.org/reports/IV/guide.html 53 This document is currently under revision (http://www.iupac.org/project/20080201400). 54 55 15 Ref. 5, chapter 14. 56 16 IUPAC, “A Classification of Linear SingleStrand Polymers (IUPAC Recommendations 1989)”, Pure Appl. Chem. 57 61 , 243–254 (1989). 58 59 60 39 P.O. 13757, Research Triangle Park, NC (919) 485-8700 IUPAC Page 40 of 40

1 Project # 2008-015-1-800 draft for SPT, Divisions IV and VIII 2 3 4 17 IUPAC. “Definitions relating to stereochemically asymmetric polymerizations” (IUPAC Recommendations 2001)”, 5 Pure Appl. Chem . 74 , 915–922 (2002). (Ref. 5, chapter 5) 6 18 IUPAC. “Generic sourcebased nomenclature for polymers (IUPAC Recommendations 2001)”, Pure Appl. Chem . 7 73 , 1511–1519 (2001). (Ref. 4, chapter 21) 8 9 19 IUPAC, “Stereochemical Definitions and Notations Relating to Polymers (IUPAC Recommendations 1980)” Pure 10 Appl. Chem . 53 , 733–752 (1981). (Ref. 5, chapter 15) 11 20 IUPAC. “Graphic representations (chemical formulae) of macromolecules (IUPAC Recommendations 1994)”, Pure 12 Appl.Chem. , 66 , 2469–2482 (1994). (Ref. 5, chapter 18) 13 21 IUPAC, “Nomenclature for Regular Singlestrand and Quasi Singlestrand Inorganic and Coordination Polymers 14 (IUPAC RecommendationsFor Peer 1984)”, Pure Appl. Review Chem. 57 , 149–168 (1985) Only (this document is currently under 15 revision). 16 17 22IUPAC. “Graphical representation standards for chemical structure diagrams”. Pure Appl. Chem. 80 , 277–410 18 (2008). 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60 40 P.O. 13757, Research Triangle Park, NC (919) 485-8700