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(12) Patent Application Publication (10) Pub. No.: US 2012/0220736A1 BURCKHARDT (43) Pub

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(12) Patent Application Publication (10) Pub. No.: US 2012/0220736A1 BURCKHARDT (43) Pub US 2012022O736A1 (19) United States (12) Patent Application Publication (10) Pub. No.: US 2012/0220736A1 BURCKHARDT (43) Pub. Date: Aug. 30, 2012 (54) ALDIMINES AND COMPOSITIONS Publication Classification COMPRISING ALDIMINE (51) Int. Cl. C08G 73/00 (2006.01) (75)75) InventorI tOr: Urss BURCKHARDT,, Zurich (CH)(CH C07C 251/08 (2006.01) (73) Assignee: SIKATECHNOLOGY AG, Baar (CH) (52) U.S. Cl. ......................................... 525/453: 560/330 (21) Appl. No.: 13/462,347 (57) ABSTRACT (22) Filed: May 2, 2012 Aldimino containing compounds obtained from a reaction of O O aldimines of formula (I) with a compound that bears at least Related U.S. Application Data one reactive group that can enter into addition reactions with (62) Division of application No. 12/451.955, filed on Dec. an HX group of an aldimine of formula I. The compounds 9, 2009, filed as application No. PCT/EP2008/059267 containing aldimine groups can be used primarily in adhesive on Jul 16, 2008. and Sealant materials, but also in coatings, and can be pro s duced easily from readily available source materials, and (30) Foreign Application Priority Data have good thermal stability. The tertiary amino group thereof has a Surprisingly low alkalinity and can in some cases have a Jul. 16, 2007 (EP) .................................. O7112503.3 catalytic effect in chemical reaction systems. US 2012/O220736A1 Aug. 30, 2012 ALDIMINES AND COMPOSITIONS simple process from primary amines and sterically hindered, COMPRISING ALDIMINE aliphatic aldehydes having a tertiary amino group. The aldi mines possess good thermal stability. The tertiary amino group thereof has a Surprisingly low basicity and can, under 0001. This is a divisional of application Ser. No. 12/451, 955 filed Dec. 9, 2009, which is a National Stage Application Some circumstances, display catalytic action in chemical of PCT/EP2008/059267 filed Jul 16, 2008, and claims the reaction systems. benefit of European Patent Application No. 07112503.3 filed 0008. These aldimines are suitable, for example, as latent Jul. 16, 2007. The entire disclosures of the prior applications hardeners for curable compositions which have groups reac are hereby incorporated by reference herein in their entirety. tive toward amines, such as epoxide groups, anhydride groups and especially isocyanate groups. Especially in polyurethane TECHNICAL FIELD compositions, they have very good compatibility and low 0002. The disclosure relates to the field of aldimines. plasticizing action. STATE OF THE ART DETAILED DESCRIPTION OF EMBODIMENTS 0003 Aldimines are condensation products formed from primary amines and aldehydes, and constitute a Substance 0009 Provided herein are aldimines of formula (I): class which has been known for some time. On contact with water, aldimines can be hydrolyzed to the corresponding amines and aldehydes. Owing to this property, they can be (I) used as a protected form of amines, or of aldehydes. For R3 example, aldimines are used in polyurethane chemistry, R4 where they serve as moisture-activable crosslinkers, known (HX--A--N1 N1 as “blocked amines' or “latent hardeners', for one- or two component compositions having isocyanate groups. R1 R2 k 0004. The advantages of the use of aldimines as latent hardeners in systems having isocyanate groups are especially that the formation of undesired gas bubbles can be avoided, 0010 where since the curing reaction via the blocked amine—in contrast 0011 A is either the radical of an amine after removal of n to the direct reaction of isocyanates with moisture—does not primary aliphatic amino groups and m HXgroups, or together proceed with release of carbon dioxide (CO), and that higher with Risan (n+2)-valent hydrocarbon radical which has 3 to curing rates and/or longer open times can be achieved. The use of aldimines as latent hardeners in compositions having 20 carbon atoms and optionally contains at least one heteroa isocyanate groups can, however, also cause problems. In the tom, especially in the form of ether oxygen or tertiary amine case of one-component compositions, the storage stability nitrogen; can be restricted significantly as a result of the presence of the 0012 n is 1 or 2 or 3 or 4, preferably 1 or 2, and m is 0 or aldimine. Depending on the aldehydes used to prepare the 1 or 2 or 3 or 4, with the proviso that m+n is 2 or 3 or 4 or 5: aldimine and released again in the curing reaction, the com (0013 R' and Rare either each independently a monova positions may additionally have a very strong odor, which is lent hydrocarbon radical having 1 to 12 carbon atoms, or intolerable for many applications. together are a divalent hydrocarbon radical having 4 to 12 0005 WO 2004/013088 A1 describes odorless polyaldi mines which are prepared from primary polyamines and carbon atoms which is part of an optionally Substituted car odorless aldehydes. WO 2007/036571 A1 describes odorless bocyclic ring having 5 to 8, preferably 6, carbon atoms; aldimines comprising at least one hydroxyl, mercapto or sec (0014) R is a hydrogen atom or an alkyl group or an ary ondary amino group, which are likewise obtainable proceed lalkyl group or an alkoxycarbonyl group, especially having 1 ing from odorless aldehydes. These odorless aldehydes may, to 12 carbon atoms; in polymer compositions, especially in polyurethane compo sitions, have a significant plasticizing action, which may be I0015I R' and Rare either each independently a monova undesired. The relatively high molecular weight of the alde lent aliphatic, cycloaliphatic or arylaliphatic radical which hydes leads, moreover, to a need to use the aldimines prepared has 1 to 20 carbon atoms and is free of hydroxyl groups and therefrom in a relatively large amount as latent hardeners, optionally contains heteroatoms in the form of ether oxygen which can make them expensive to use. or tertiary amine nitrogen, or together are a divalent aliphatic radical which has 3 to 20 carbon atoms and is part of an SUMMARY optionally substituted heterocyclic ring having 5 to 8, prefer 0006. It is an object of the present disclosure to provide ably 6, ring atoms, this ring being free of hydroxyl groups novel aldimines which can be used as latent hardeners in and, as well as the nitrogen atom, optionally containing fur curable compositions, especially in one- or two-component ther heteroatoms in the form of ether oxygen or tertiary amine compositions having isocyanate groups. nitrogen; 0007. It has been found that, surprisingly, the aldimines in (0016 X is O or S or N-R or N-R, where R is eithera accordance with this disclosure achieve this object and have monovalent hydrocarbon radical which has 1 to 20 carbon advantageous properties. These are usually room temperature atoms and optionally has at least one carboxylic ester, nitrile, liquid compounds which have barely any aldehyde odor and nitro, phosphonic ester, Sulfone or Sulfonic ester group, or a are preparable from readily obtainable base materials in a substituent of formula (II) US 2012/O220736A1 Aug. 30, 2012 hydrocarbon radical which has 3 to 20 carbon atoms and optionally contains at least one heteroatom, especially in the (II) R3 form of ether oxygen or tertiary amine nitrogen; 0031 X is O or S or N R or N R, where R is either ----B-I-N1 r R4 a monovalent hydrocarbon radical which has 1 to 20 carbon atoms and optionally has at least one carboxylic ester, nitrile, R R.2 R5 p nitro, phosphonic ester, Sulfone or Sulfonic ester group, or a substituent of formula (IIa) 0017 where 0018 p is 0 or an integer from 1 to 10 000, and 0019 B is a (p+1)-valent hydrocarbon radical which (IIa) optionally contains ether oxygen, tertiary amine nitrogen, hydroxyl groups, secondary amino groups or mercapto groups; and R together with A is an (n+2)-valent hydrocar bon radical which has 3 to 20 carbon atoms and optionally contains at least one heteroatom, especially in the form of ether oxygen or tertiary amine nitrogen. 0020. The broken lines in the formulae in this document each represent the bond between a substituent and the rest of 0032 where B' is a divalent hydrocarbon radical which the associated molecule. has 2 to 12 carbon atoms and optionally has ether oxygen or 0021. The term “primary amino group” in the present tertiary amine nitrogen; and document denotes an amino group in the form of an NH I0033 R together with A' is a trivalent hydrocarbon radi group which is bonded to an organic radical. The term "sec cal which has 3 to 20 carbon atoms and optionally contains at ondary amino group' denotes an amino group in which the least one heteroatom, especially in the form of ether oxygen nitrogen atom is bonded to two organic radicals which may or tertiary amine nitrogen, and also together be part of a ring. The term “tertiary amino group' denotes an amino group in which the nitrogenatom is 0034) R', R. R. R. and Rare each as defined above. bonded to three organic radicals, where two of these radicals 0035 Inafurther embodiment of the aldimines of formula may also together be part of a ring tertiary amine nitrogen). (I), the index m is Zero and the index n is 2 or 3 or 4. Such 0022 "Aliphatic' refers to an amine or an amino group in aldimines are polyaldimines. Substance names beginning which the nitrogen atom is bonded exclusively to aliphatic, with “poly'. Such as polyaldimine, polyamine or polyisocy cycloaliphatic or arylaliphatic radicals. anate, refer in the present document to Substances which, in a 0023 The term “active hydrogen' in the present document formal sense, contain two or more of the functional groups refers to the hydrogen atom of a hydroxyl, mercapto or sec which occur in their name per molecule.
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