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Part I Block Copolymers Part Ii Polymers of 1,3 Part I: Block copolymers Part II: Polymers of 1,3-dithioles Item Type text; Dissertation-Reproduction (electronic) Authors Leland, John Everard, 1944- Publisher The University of Arizona. Rights Copyright © is held by the author. Digital access to this material is made possible by the University Libraries, University of Arizona. Further transmission, reproduction or presentation (such as public display or performance) of protected items is prohibited except with permission of the author. Download date 26/09/2021 01:56:12 Link to Item http://hdl.handle.net/10150/565253 PART I BLOCK COPOLYMERS PART II POLYMERS OF 1,3-DITHIOLES i by | ' ' John Everard Leland A Dissertation Submitted to the Faculty of the DEPARTMENT OF CHEMISTRY In Partial Fulfillment of the Requirements For the Degree of ■ DOCTOR OF PHILOSOPHY In the Graduate College THE UNIVERSITY OF ARIZONA 1 9 7 2 THE UNIVERSITY OF ARIZONA GRADUATE COLLEGE I hereby recommend that this dissertation prepared under my direction by John Everard Leland______________________________ entitled _______ Part I Block Copolymers_________________________ _______ Part II Polymers of 1.3-Dithioles_______________ be accepted as fulfilling the dissertation requirement of the Doctor of Philosophy degree of ________________________ ________________________________ JU-C4-J O r h Dissertation Director J Date After inspection of the final copy of the dissertation, the following members of the Final Examination Committee concur in its approval and recommend its acceptance:- 8/7/72 This approval and acceptance is contingent on the candidate's adequate performance and defense of this dissertation at the final oral examination. The inclusion of this sheet bound into the library copy of the dissertation is evidence of satisfactory performance at the final examination. STATEMENT BY AUTHOR This dissertation has been submitted in partial fulfillment of requirements for an advanced degree at The University of Arizona and is deposited in the University Library to be made available to bor­ rowers under rules of ,the Library. Brief quotations from this dissertation are allowable without special permission, provided that accurate acknowledgment of source is made. Requests for permission for extended quotation from or re­ production of this manuscript in whole or in part may be granted by the head of the major department or the Dean of the Graduate College when in his judgment the proposed use of the material is in the in­ terests of scholarship. In all other instances, however, permission must be obtained from the author. SIGNED: To Rita Kay, Michael, Mark, and Matthew iii ACKNOWLEDGMENT The author wishes to thank Dr. James E. Mulvaney for his guidance and help during the course of this research and the v . Petroleum Research Fund of the American Chemical Society for its financial support. ' TABLE OF CONTENTS Page LIST OF T A B L E S ............ ix ABSTRACT x PART I: BLOCK COPOLYMERS ................... 1 I ' INTRODUCTION . 2 RESULTS AND DISCUSSION ........... 11 EXPERIMENTAL .............. ..... 24 Materials............ ................... 24 Instrumentation ........... .................. 25 Elemental Analyses .......... 25 Experimental Procedure ......... ... 26 Poly(styrene-co-vinylene Carbonate) (17) ...... 26 Poly(styrene-co-vinylene Glycol) (17a) ....... 26 Preparation of Carboxyl-terminated Polystyrene (17b) . .......... .. 26 Poly(4-vinyltoluene-co-vinylene Carbonate) (22) . 27 Poly(4-vinyItoluene-co-vinylene Glycol) (22a) .... 27 Preparation of Carboxyl-terminated Poly(4-vinyl- toluene) ( 2 2 b ) .............................. 27 Titration of Carboxyl-terminated Polymers ...... 28 Methylation of Carboxyl-terminated Polystyrene . 28 Treatment of Carboxyl-terminated Polystyrene with Periodic Acid .......... 29 Preparation of Hydroxy1-terminated Poly(ethylene Adipate) (23) ............ 29 Titration and Molecular Weight Determination of Hydroxyl-terminated Poly(ethylene Adipate) (23) . 29 Viscosity of a 50:50 Molar Solution of Hydroxyl- terminated Poly (ethylene Adipate) (23) and Carboxyl-terminated Polystyrene (19b) ....... 29 Attempt to Couple Carboxyl-terminated Polystyrene (18b) with Hexamethylenediamine by the Inter- facial Method ...... ........ 30 Coupling of Carboxyl-terminated Polystyrene (18b) with Hexamethylenediamine by the Solution Polycondensation Process in Chloroform with Triethylamine ................... 30 v vi TABLE OF CONTENTS— Continued Page Coupling of Carboxyl-terminated Polystyrene (19b) with Hexamethylenediamine by the Solution Polycondensation Process in 1,2-Dichloroethane with Tri ethyl am i n e ................................... 31 Attempt to Couple Carboxyl-terminated Polystyrene (19b) with Hydroxyl-terminated Poly(ethylene Adipate) (23) by the Solution Polycondensation Process in 1,2-Dichloroethane with Triethy1- amine ....................... 31 Coupling of Carboxyl-terminated Polystyrene (19b) with Hydroxyl-terminated Poly(ethylene Adipate) (23) by the Solution Polycondensation Process in Dioxane with Pyridine 32 Coupling of Carboxyl-terminated Polystyrene (19b) with Hydroxyl-terminated Poly(ethylene Adipate) (23) by the Solution Polycondensation Process in Dioxane • . 32 Coupling of Carboxyl-terminated Polystyrene (19b) with Hydroxyl-terminated Poly(ethylene Adipate) (23) by the Solution Polycondensation Process in Nitrobenzene .................. 32 Coupling of Carboxyl-terminated Polystyrene (19b) with 1,10-Decanediol by Melt ........... 33 Coupling of Carboxyl-terminated Polystyrene (19b) with 1,10-Decanediol by the Solution Polycondensation Process in Nitrobenzene ...... 33 Coupling of Carboxyl-terminated Poly(4-viny1- toluene) (22b) with Methylene Bis(4-phenyl Isocyanate) . ............ 34 Coupling of Carboxyl-terminated Poly(4-viny1- toluene) (22b) with 1,10-Decanediol Using Trifluoroacetic Anhydride ..... ... 34 Coupling of Carboxyl-terminated Poly(4-vinyl- toluene) (22b) with Hexamethylenediamine by the Solution Polycondensation Process with Diamine as the Acid Acceptor ^ 35 Coupling of Carboxyl-terminated Poly(4-vinyl- toluene) (22b) with Hexamethylenediamine- terminated Poly(4-viny1toluene) by a Solution Process ................. 35 Coupling of Carboxyl-terminated Poly(4-viny1- toluene) (22b) with Excess Hydroxyl-terminated Poly(ethylene Adipate) (23) by a Solution Process ...................... 36 TABLE OF CONTENTS— Continued Page Coupling of Carboxyl-terminated Poly(4-viny1- toluene) (22b) with Hydroxyl-terminated Poly(4-vinyltoluene) (24) by a Solution Process . .................... 36 Coupling of Carboxyl-terminated Poly(4-vinyl- toluene) (22b) with Hydroxyl-terminated Poly(ethylene Adipate) (23) by a Solution Process in Pyridine...................... 36 ■ Coupling of Carboxyl-terminated Polystyrene (20b) with Hydroxyl-terminated Poly(ethylene Adipate) (23) by the Solution Process in Pyridine i . 37 Coupling of Carboxyl-terminated Poly(4-viny1- toluene) (22b) with Hydroxyl-terminated Poly(propylene Glycol) by the Solution Process........... ... « . .............. 37 PART II: POLYMERS OF 1,3-DITHIOLES . .........................38 INTRODUCTION . , . .......... 39 RESULTS AND D I S C U S S I O N ................ 43 EXPERIMENTAL . .......... 52 Materials .......... ................ 52 Instrumentation .............................. .. .. 54 Elemental Analyses ^ 0 . 54 Experimental Procedures . ............... 54 Preparation of l,3-Dithiole-2-thione . ............ 54 Preparation of l,3"Dithiole-2-one ^ » 55 Attempt to Polymerize 193-Dithiole- 2-thione R a d i c a l l y ........ .............. .. 55 Attempt to Polymerize 153-Dithiole- 2-thione Cationically . 55 Attempt to Copolymerize 153-Dithiole- 2-thione and Styrene . .......... 56 Attempt to Polymerize 1,3-Dithiole- 2-one Radically • . 56 Copolymerization of l,3-Dithiole"2-one and Methyl Methacrylate with Zinc Chloride .......... 56 Preparation of 153-Dithiolane-4?5-dione Bis(dicyano Vinylene Thioketal) : 57 viii TABLE OF CONTENTS "Continued Page Attempt to Prepare 2,3,6,7-Tetracyano- 1.4.5.8-tetrathiafulvalene by the Pyrolysis of l,3-Dithiolane-4,5-dione Bis (dicyano Vinylene Thioketal) .......... 57 Attempt to Prepare 2,3,6,7-Tetracyano- 1,4,5,8~tetrathiafulvalene by Desulfu- rization of 4,5-Dicyano-l,3-dithiole- 2-thione * . , . , . 58 Attempt to form Diels-Alder Adduct of 4,5-Dicyano~ 1.3-dithiole~2-thione with Cyclopentadiene ........ 58 Polycondensation of 1,3-Dithiole-2~thione-4,5- dicarboxylic Acid with Hexamethylenediamine . 59 Attempt to Prepare 2,3,6,7-Tetracarboxylie Acid- 1.4.5.8-tetrathiafulvalene ...... ............ 59 Preparation of 2,3,6,7-Tetramethy1~1,4,5,8- tetrathiafulvalene Tetracarboxylate ................ 60 Attempted Preparation of Diethyl-1,4,5,8- tetrathiafulvalene Dicarboxylate.......... .. 61 Attempt to Prepare Diethyl-1,4, 5,8-tetrathiaful- valene Dicarboxylate ................. 61 Preparation of Dimethyl-2-benzylidene~l,3- dithiole-4,5-dicarboxylate e . e ......... 62 Polycondensation of 2,3,6,7-Tetramethyl- . 1.4.5.8-tetrathiafulvalene Tetracarboxylate with Hexamethylenediamine by a Melt Process ..... 62 Condensation of 2', 3,6, 7-Tetramethyl-l,4, 5, 8- tetrathiafulvalene Tetracarboxylate with Butylamine . ................... 63 Hydrolysis of 2,3,6,7-Tetramethyl-l,4,5,8- tetrathiafulvalene Tetracarboxylate ......... 63 Polycondensation of Dimethy1-2-benzylidene- 1.3-dithiole-4,5-dicarboxylate with Hexa­ methy lenediamine by a Solution Process ....... 64 Polycondensation of Dimethyl-2-benzylidene- 1.3-dithiole-4,5-dicarboxylate with Hexa­ methy lenediamine by a Melt Process
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