Claims
- 1. A composition, suitable for coating, impregnating, and/or bonding purposes and adapted to be cured under ambient conditions, comprising a liquid vehicle containing:
- (1) A soluble vinyl addition polymer of monoethylenically unsaturated monomers, said polymer containing a plurality of primary or secondary amine groups and/or aldimine or ketimine groups pendant from spaced mers or polymer units in the polymer chain,
- (2) At least one compound having at least two acryloxy groups of the formula
- H.sub.2 C.dbd.C(H)C(O)--O--
- and
- (3) Optionally when component (1) is a polymer containing only primary and/or secondary amine groups, a volatile (C.sub.3 -C.sub.10) ketone or (C.sub.3 -C.sub.10) aldehyde stabilizer which retards the reaction of (1) and (2) under ambient conditions,
- wherein component (1) comprises at least one of:
- (a) An amidation product of a vinyl addition copolymer of a mixture of monoethylenically unsaturated monomers containing a lower alkyl (meth)acrylate with a polyamine having at least two amino groups selected from primary and secondary amino groups and having their nitrogen atoms attached to aliphatic carbon atoms,
- (b) A ketimine or aldimine derivative of (a) obtained by reaction of primary amine groups in (a) with a (C.sub.3 -C.sub.10) ketone or a (C.sub.3 -C.sub.10) aldehyde, and
- (c) A soluble vinyl addition copolymer of a monomer having a general formula H-I, H-II, H-III or E-I, these formulas being as follows: ##STR18## where m is an integer having a value of 4 to 5,
- n is an integer having a value of 1 to 2,
- A is a C.sub.2 -C.sub.12 alkylene group,
- R' is a (C.sub.1 -C.sub.12) alkyl or cycloalkyl group,
- R.sup.2 is a (C.sub.1 -C.sub.12) alkyl or cycloalkyl group, and
- R.sup.3 is selected from the group consisting of phenyl, halophenyl, and alkoxyphenyl in which the alkoyl group has one to four carbon atoms, and ##STR19## wherein: Q is selected from the group consisting of ##STR20## R is H or it may be methyl in one CHR unit, R.sup.1 is selected from the group consisting of (C.sub.1 -C.sub.12) alkyl and cyclohexyl groups,
- R.sup.2 is selected from the group consisting of (C.sub.1 -C.sub.12) alkyl and cyclohexyl groups,
- R.sup.3 is selected from the group consisting of phenyl halophenyl, (C.sub.1 -C.sub.12) alkyl, cyclohexyl, and (C.sub.1 -C.sub.4) alkoxyphenyl groups,
- A', B, and D are the same or different oxyalkylene groups having the formula ##STR21## R.degree. being individually selected from the group consisting of H and alkyl radicals having 1 to 2 carbon atoms,
- m is an integer having a value of 1 to 2,
- x is an integer having a value of 4 to 5,
- n is an integer having a value of 1 to 200,
- n' is an integer having a value of 1 to 200,
- n" is an integer having a value of 1 to 200, the sum of n-1, n'-1, and n"-1 having a value of 2 to 200,
- the relative amount of (2) to (1), based respectively on acryloxy unsaturation equivalency of (2) and amine (primary and/or secondary) nitrogen equivalency of (1), being such as to provide at least from 0.5 to 3.5 equivalents of (2) for each equivalent of (1).
- 2. A composition according to claim 1 wherein component (1) is a copolymer of a (meth)acryloxyalkyl ketimine or aldimine as defined in formulas H-I, H-II and H-III therein, or of a (meth)acryloxyalkyloxyalkyl ketimine or aldimine of formula E-I therein.
- 3. A composition according to claim 2 wherein component (1) is a copolymer of diisopropylketiminoethyl methacrylate.
- 4. A composition according to claim 3 wherein component (2) is a diacrylate ester of a liquid epoxy resin.
- 5. A composition according to claim 3 wherein component (2) is an acrylated glycidyl methacrylate/styrene copolymer having at least two unsaturated acryloxy groups.
- 6. A composition according to claim 1 wherein component (2) also contains a monoethylenically unsaturated monomer of the formula
- H.sub.2 C.dbd.C(R)--X IV
- wherein R is H or CH.sub.3, preferably H, and X is an electron-withdrawing group, examples of such compounds being acrylonitrile, alkyl (meth)acrylates, (meth)acrylamides, and N-alkyl-substituted-(meth)acrylamides.
- 7. A composition according to claim 1 wherein component (1) is a soluble vinyl addition polymer amidation product (a) containing amine groups, at least a portion of such groups being at least partially blocked by reaction thereof with isobornyl acrylate prior to mixing components (1) and (2) whereby pot-life of the composition is extended, and the properties of coatings obtained are modified.
- 8. A composition according to claim 1 wherein the relative amount of (2) to (1) based respectively on acryloxy unsaturation equivalency of (2) and amine (primary and/or secondary) nitrogen equivalency of (1) is such as to provide from about 1 to 2 equivalents of (2) for each equivalent of (1).
- 9. A composition according to claim 1 wherein amine-containing or imine-containing polymer in (1) has a molecular weight in the range of at least about 600 to 5,000 number average.
- 10. A composition according to claim 1 wherein (2) also contains at least one compound having a single (meth)acryloxy group.
- 11. A composition according to claim 1 wherein component (1) comprises an amidation product of a vinyl addition copolymer of monoethylenically unsaturated monomers containing a lower alkyl (meth)acrylate with a polyamine having at least two amino groups selected from primary and secondary amino groups and having their nitrogen atoms attached to aliphatic carbon atoms.
- 12. A composition according to claim 11 wherein the polyamine is selected from those having the formula
- H.sub.2 N--R.degree.--(NHR.degree.).sub.n --NH.sub.2 (II)
- wherein R.degree. is an alkylene group having 2 to 3 carbon atoms and n is 0, 1, 2 or 3.
- 13. A composition according to claim 11 wherein the polyamine is ethylenediamine and the amidation product in (1) contains units of the formula ##STR22## wherein R is H or CH.sub.3.
- 14. A composition according to claim 11 wherein the polyamine is 1,3-propylenediamine.
- 15. A composition according to claim 11 wherein component (3) is present and comprises a volatile aldehyde or ketone having 3 to 10 carbon atoms whereby primary amine groups in component (1) are converted to aldimine or ketimine groups thereby retarding the reaction between components (1) and (2) under ambient conditions.
- 16. A composition according to claim 1 wherein (3) is present and comprises a volatile aldehyde or ketone having 3 to 10 carbon atoms.
- 17. A composition according to claim 1 in which component (2) comprises a simple ester obtained by the reaction of a polyol having at least two hydroxyl groups with acrylic acid or methacrylic acid.
- 18. A composition according to claim 17 in which component (2) is trimethylolpropane triacrylate.
- 19. A composition according to claim 1 in which component (2) is a poly(200)ethylene glycolacrylate.
- 20. A composition according to claim 1 in which component (2) comprises a urethane acrylate obtained by reacting at least two isocyanate groups of a polyisocyanate with a hydroxyalkyl acrylate.
- 21. A composition according to claim 1 in which component (2) comprises a polyester having at least two acrylate groups obtained by esterifying hydroxy groups with (meth)acrylic acid.
- 22. A composition according to claim 1 in which component (2) comprises a polyfunctional acrylate obtained by reaction of a hydroxyalkyl acrylate with (a) a dicarboxylic acid having 4 to 15 carbon atoms, (b) a polyepoxide having terminal glycidyl groups, or (c) a polyisocyanate having terminal reactive isocyanate groups.
- 23. A composition according to claim 1 in which component (2) comprises a acrylate-terminated polyester made from acrylic acid, a polyol having at least three hydroxyl groups, and a dicarboxylic acid.
- 24. A composition according to claim 1 in which component (2) comprises a polyfunctional acrylate obtained by the reaction of acrylic acid with at least 2 epoxy groups of an epoxidized drying oil, or epoxidized drying oil fatty acid ester, or amide thereof, or a corresponding alcohol, containing at least two epoxy groups.
- 25. A composition according to claim 1 in which component (2) comprises a urethane derivative or amine derivative of a polyfunctional acrylate of claim 21 obtained by the reaction of an isocyanate or amine respectively with the polyfunctional acrylate while retaining at least two acrylate groups therein.
- 26. A composition according to claim 1 in which component (2) comprises an acrylic acid adduct to an epoxidized vegetable or animal oil having ten or more carbon atoms in the fatty acid component and sufficient unsaturation to provide at least two epoxy groups in the epoxidized oil.
- 27. A composition according to claim 26 in which the oil is soybean oil.
- 28. A composition according to claim 26 in which the oil is linseed oil.
- 29. A composition according to claim 1 in which component (2) comprises a polyacrylate obtained by the reaction of acrylic acid by addition to the epoxy groups of an aromatic bisphenol-based epoxy resin.
- 30. A composition according to claim 1 in which component (2) comprises a diacrylate ester of a liquid bisphenol A epoxy resin.
- 31. A composition according to claim 1 in which component (2) comprises a polyacrylate obtained by the addition of acrylic acid to a liquid vinyl polymer having pendant glycidyl groups resulting from addition polymerization of a monomer mixture comprising glycidyl acrylate, glycidyl vinyl ether or glycidyl vinyl sulfide.
- 32. A composition according to claim 1 in which component (2) comprises a polyfunctional acrylate derived from acrylic acid anhydride and a polyepoxide.
- 33. A composition according to claim 1 in which component (2) comprises a polyfunctional acrylate urethane ester obtained from the combining of a hydroxyalkyl acrylate, a diisocyanate, and a hydroxy functional alkyd condensate.
- 34. A composition according to claim 1 in which component (2) comprises a acrylate-terminated polyester obtained by the reaction of a polycaprolactone diol or triol with a diisocyanate, and a hydroxyalkyl acrylate.
- 35. A composition according to claim 1 in which component (2) comprises a urethane polyacrylate obtained by the reaction of a hydroxyl-containing ester of a polyol with acrylic acid and a polyisocyanate.
- 36. An essentially anhydrous composition according to claim 1 wherein component (1) consists essentially of a ketimine-containing amidation product of a vinyl addition copolymer containing a lower alkyl acrylate with an aliphatic polyamine having at least two primary amine groups, substantially all of the primary amine groups in the amidation product having been converted into ketimine groups by reaction with an aliphatic or alicyclic C.sub.3 to C.sub.10 ketone with removal of the water liberated by that reaction, whereby the composition has improved pot-life and is hydrocurable when applied to surfaces of a substrate for coating, adhering or sealing thereof under ambient conditions of temperature (20.degree.-25.degree. C.) and relative humidity of at least 20%.
- 37. A composition according to claim 36 wherein the polyamine is ethylenediamine and the ketone is diisopropyl ketone.
- 38. A composition according to claim 36 wherein the polyamine is ethylenediamine and the ketone is ethyl amyl ketone.
- 39. A composition according to claim 1 in which component (1) contains no aldimine or ketimine groups and the composition contains volatile ketone or aldehyde stabilizer which retards reaction of amine groups in component (1) with component (2).
CROSS-REFERENCE TO RELATED APPLICATION
This application is a continuation-in-part of our copending application Ser. No. 965,673, filed Jan. 1, 1978, and of our copending application Ser. No. 865,568 filed Dec. 29, 1977, now abandoned.
US Referenced Citations (15)
Continuation in Parts (1)
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Number |
Date |
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965673 |
Jan 1978 |
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