Claims
- 1. A composition crosslinkable in an aqueous acidic medium comprising a compound having at least two formylamido groups and a polymer having at least two amidocarbonyl groups, the formylamido group and the amidocarbonyl group of said compound and polymer reacting in the aqueous acidic medium to form crosslink bridges of structural units of the formula --NR.sup.x --CH.dbd.N--CO--, wherein R.sup.x represents hydrogen, alkyl having 1 to 4 carbon atoms or --CH.sub.2 OH.
- 2. A crosslinkable, water-soluble composition according to claim 1 comprising:
- A. a water-soluble homo- or copolymer having amidocarbonyl groups in an amount of more that 10%, calculated on the weight of the polymer and
- B. a member selected from the group consisting of (a) a bis-acylamido-compound of the formula I ##STR67## wherein R.sup.1 and R.sup.2 represent hydrogen, alkyl having 1 to 4 carbon atoms or --CH.sub.2 OH,
- n represents a number from 1 to 3 and
- m represents a number from 0 or to 1, and
- (b) a water soluble homo- or copolymer having formylamido groups of the formula ##STR68## wherein R.sup.9 stands for hydrogen or alkyl having 1 to 4 carbon atoms or --CH.sub.2 OH, the amount of formylamido groups being not less than 1 mol per 500 g of the polymer.
- 3. A crosslinkable, water-soluble composition according to claim 2 wherein component A comprises 50 to 100% by weight of entities of the formula II ##STR69## wherein R.sup.4 stands for hydrogen or methyl and of 0 to 50% by weight of entities of the formula III ##STR70## wherein R.sup.5 stands for hydrogen, alkyl having 1 to 3 carbon atoms, and Y stands for formylamido; N-substituted formylamido where the N-substituent is methyl or hydroxy methyl; cyano; carboxyl; the alkali or ammonium salts of carboxyl; the alkoxycarbonyl group having 1 to 6 carbon atoms; the hydroxy-alkoxycarbonyl group having 1 to 3 carbon atoms; the N-methylolamidocarbonyl group HOCH.sub.2 NH--CO--; the N-methylolamidocarbonyl group wherein the methylol group is etherified with alkanols having 1 to 4 carbon atoms; the mono- or dialkylamino group having altogether 1 to 8 carbon atoms in the alkyl radicals; the alkanoylamino group having 1 to 4 carbon atoms; the alkanoylamino group having 1 to 4 carbon atoms which is N-substituted with methylol or alkyl having 1 to 4 carbon atoms; pyrrolidonyl-(1); phenyl; pyridinium; the sulfonic acid group; the sulfoalkylamidocarbonyl group having 1 to 4 carbon atoms; the phosphonic acid group; the alkali or ammonium salts of said sulfonic acids and phosphonic acid groups; a radical of the formula IV ##STR71## a radical of the formula V ##STR72## wherein R.sup.7 and R.sup.8 are the same or different and stand for alkyl having 1 to 4 carbon atoms and p represents a number from 1 to 4, or quaternary salts of formulas IV and V.
- 4. A crosslinkable, water-soluble composition according to claim 2 wherein components (A) and (B) are present in a ratio by weight of from 1:0.2 to 1:20.
- 5. A crosslinkable, water-soluble composition according to claim 1 comprising a water-soluble homo- or copolymer having amidocarbonyl groups and a water-soluble homo- or copolymer having formylamido groups of the formula ##STR73## wherein R.sup.9 is hydrogen or alkyl having 1 to 5 carbon atoms.
- 6. A crosslinkable, water-soluble composition according to claim 1 wherein the polymer having formylamido groups is a homopolymer of vinyl formamide.
- 7. A crosslinked polymer composition obtained by reacting in a highly acidic aqueous medium pendant amidocarbonyl groups of the formula --CONH.sub.2 of component (A) with formylamido groups of component (B), component (A) comprising a water-soluble homo- or copolymer having amidocarbonyl groups in an amount of more than 10%, calculated on the weight of the polymer and component (B) comprising a member selected from the group consisting of
- (a) a bis-acylamido-compound of the formula I ##STR74## wherein R.sup.1 and R.sup.2 represent hydrogen, alkyl having 1 to 4 carbon atoms or --CH.sub.2 OH,
- n represents a number from 1 to 3 and
- m represents a number from 0 to 1, and
- (b) a water-soluble homo- or copolymer having formylamido groups of the formula ##STR75## wherein R.sup.9 stands for hydrogen or alkyl having 1 to 4 carbon atoms or --CH.sub.2 OH, the amount of formylamido groups being not less than 1 mol per 500 g of the polymer.
- 8. A crosslinked polymer composition according to claim 7 wherein component (A) comprises 50 to 100% by weight of entities of the formula II ##STR76## wherein R.sup.4 stands for hydrogen or methyl and of 0 to 50% by weight of entities of the formula III ##STR77## wherein R.sup.5 stands for hydrogen, alkyl having 1 to 3 carbon atoms and
- Y stands for formylamido; N-substituted formylamido where the N-substituent is methyl or hydroxymethyl; cyano; carboxyl; or the alkali or ammonium salts of carboxyl; the alkoxycarbonyl group having 1 to 6 carbon atoms; the hydroxy-alkoxycarbonyl group having 1 to 3 carbon atoms; the N-methylolamidocarbonyl group HOCH.sub.2 NH--CO--; the N-methylolamidocarbonyl group wherein the methylol group is etherified with alkanols having 1 to 4 carbon atoms; the mono- or dialkylamino group having altogether 1 to 8 carbon atoms in the alkyl radicals; the alkanoylamino group having 1 to 4 carbon atoms; the alkanoylamino group having 1 to 4 carbon atoms which is N-substituted with methylol or alkyl having 1 to 4 carbon atoms; pyrrolidonyl-(1); phenyl; pyridinium; the sulfonic acid group; the sulfoalkylamidocarbonyl group having 1 to 4 carbon atoms; the phosphonic acid group; the alkali or ammonium salts of said sulfonic acids and phosphonic acid groups; a radical of the formula IV ##STR78## a radical of the formula V ##STR79## wherein R.sup.7 and R.sup.8 are the same or different and stand for alkyl having 1 to 4 carbon atoms and p represents a number from 1 to 4; or quaternary salts of formulas IV and V.
- 9. A crosslinked polymer composition according to claim 7 or claim 8 wherein component (B) comprises 50 to 100% by weight of entities of the formula VI ##STR80## wherein R.sup.9 stands for hydrogen, methyl or hydroxy methyl and of 0 to 50% by weight of entities of the formula VII ##STR81## wherein R.sup.11 stands for hydrogen or methyl and
- X stands for cyano; the carboxyl group; the alkali or ammonium salts of carboxyl; the alkoxycarbonyl group having 1 to 6 carbon atoms; the hydroxy-alkoxycarbonyl group having 1 to 3 carbon atoms; the N-methylolamidocarbonyl group HOCH.sub.2 NH--CO--; the N-methylolamidocarbonyl group wherein the methylol group is etherified with alkanols having 1 to 4 carbon atoms; the alkanoylamino group having 1 to 4 carbon atoms; the alkanoylamino group having 1 to 4 carbon atoms which is N-substituted with methylol or alkyl having 1 to 4 carbon atoms; pyrrolidonyl-(1); phenyl; pyridinium; the sulfonic acid group; a sulfoalkylamidocarbonyl group having 1 to 4 carbon atoms; the phosphonic acid group; the alkali or ammonium salts of said sulfonic acids and phosphonic acid groups; a radical of the formula VIII ##STR82## wherein R.sup.12 and R.sup.13 are the same or different and stand for alkyl having 1 to 4 carbon atoms; a radical of the formula IX ##STR83## wherein p represents a number from 1 to 4; a radical of the formula X ##STR84## wherein R.sup.14 and R.sup.15 are the same or different and stand for alkyl having 1 to 4 carbon atoms quaternary salts of formula IX and X.
- 10. A crosslinked, polymer composition according to claim 7 wherein components (A) and (B) are present in a ratio by weight of from 1:0.2 to 1:20.
- 11. A crosslinked, polymer composition according to claim 7 wherein component (A) is a water-soluble homo- or copolymer having pendant amidocarbonyl groups of the formula --CONH.sub.2 and component (B) is a bis-acylamide-compound of the formula I ##STR85## wherein R.sup.1 and R.sup.2 are hydrogen, alkyl having 1 to 4 carbon atoms or CH.sub.2 OH.
- 12. A crosslinked, polymer composition according to claim 11 wherein component (B) is methylene-bis-formamide or bis-(N-formyl-aminomethyl)ether.
- 13. A crosslinked polymer composition according to claim 7 wherein component (A) is a water-soluble homo- or copolymer having pendant amidocarbonyl groups of the formula CONH.sub.2 and component (B) is a water-soluble homo- or copolymer having formylamide groups of the formula ##STR86## wherein R.sup.9 is hydrogen or alkyl having 1 to 4 carbon atoms or --CH.sub.2 OH.
- 14. A crosslinked, polymer composition according to claim 7 wherein component (B) is a homopolymer of vinyl formamide.
- 15. A method of forming a crosslinked composition having crosslink bridges of structural units of the formula --NR.sup.x --CH.dbd.N--CO-- comprising reacting a compound having at least two formylamido groups with a polymer having at least two amidocarbonyl groups in an aqueous acidic medium.
- 16. A method of forming a crosslinked composition which comprises reacting in a highly acidic aqueous medium pendant amidocarbonyl groups of the formula --CONH.sub.2 of component (A) with formylamido groups of component (B), component (A) comprising a water-soluble homo- or copolymer having amidocarbonyl groups in an amount of more than 10%, calculated on the weight of the polymer and component (B) comprising a member selected from the group consisting of (a) a bis-acylamido-compound of the formula I ##STR87## wherein R.sup.1 and R.sup.2 represent hydrogen, alkyl having 1 to 4 carbon atoms or --CH.sub.2 OH,
- n represents a number from 1 to 3 and
- m represents a number from 0 to 1 and
- (b) a water-soluble homo- or copolymer having formylamido groups of the formula ##STR88## wherein R.sup.9 stands for hydrogen or alkyl having 1 to 4 carbon atoms or --CH.sub.2 OH the amount of formylamido groups being not less than 1 mol per 500 g of the polymer.
- 17. A method according to claim 16 wherein component (A) comprises 50 to 100% by weight of entities of the formula II ##STR89## wherein R.sup.4 stands for hydrogen or methyl and of 0 to 50% by weight of entities of the formula III ##STR90## wherein R.sup.5 stands for hydrogen, alkyl having 1 to 3 carbon atoms and Y stands for formylamido; N-substituted formylamido where the N-substituent is methyl or hydroxy methyl; cyano; carboxyl; or the alkali or amonium salts of carboxyl; the alkoxycarbonyl group having 1 to 6 carbon atoms; the hydroxy-alkoxycarbonyl group having 1 to 3 carbon atoms; the N-methylolamidocarbonyl group HOCH.sub.2 NH--CO--; the N-methylolamidocarbonyl group wherein the methylol group is etherified with alkanols having 1 to 4 carbon atoms; the mono- or dialkylamino groups having altogether 1 to 8 carbon atoms; the alkanoylamino group having 1 to 4 carbon atoms, the alkanoylamino group having 1 to 4 carbon atoms which is N-substituted with methylol or alkyl having 1 to 4 carbon atoms, pyrrolidonyl-(1); phenyl; pyridinium; the sulfonic acid group; the sulfoalkylamidocarbonyl group having 1 to 4 carbon atoms; the phosphonic acid group; the alkyl or ammonium salts of said sulfonic acids and phosphonic acid groups, a radical of the formula IV ##STR91## a radical of the formula V ##STR92## wherein R.sup.7 and R.sup.8 are the same or different and stand for alkyl having 1 to 4 carbon atoms and p represents a number from 1 to 4; or quaternary salts of formulas IV and V.
- 18. A method according to claim 16 wherein component (B) comprises 50 to 100% by weight of entities of the formula VI ##STR93## wherein R.sup.9 stands for hydrogen, methyl or hydroxyl methyl and of 0 to 50% by weight of entities of the formula VII ##STR94## wherein R.sup.11 stands for hydrogen or methyl and
- X stands for cyano; the carboxyl group; the alkali or ammonium salts of carboxyl; the alkoxy carbonyl group having 1 to 6 carbon atoms; the hydroxy-alkoxycarbonyl group having 1 to 3 carbon atoms, the N-methylolamidocarbonyl group HOCH.sub.2 NH--CO--; the N-methylolamidocarbonyl group wherein the methylol group is etherified with alkanols having 1 to 4 carbon atoms; the alkanoylamino group having 1 to 4 carbon atoms; the alkanoylamino group having 1 to 4 carbon atoms which is N-substituted with methylol or alkyl having 1 to 4 carbon atoms; pyrrolidonyl-(1); phenyl; pyridinium; the sulfonic acid group; a sulfoalkylamidocarbonyl group having 1 to 4 carbon atoms; the phosphonic acid group; the alkali or ammonium salts of said sulfonic acids and phosphonic acid groups; a radical of the formula VIII ##STR95## wherein R.sup.12 and R.sup.13 are the same or different and stand for alkyl having 1 to 4 carbon atoms; a radical of the formula IX ##STR96## wherein p represents a number from 1 to 4; a radical of the formula X ##STR97## wherein R.sup.14 and R.sup.15 are the same or different and stand for alkyl having 1 to 4 carbon atoms; or quaternary salts of formulas IX and X.
- 19. A method according to claim 16 wherein component (A) is a water-soluble homo- or copolymer having pendant amido.dbd.carbonyl groups of the formula --CONH.sub.2 and component (B) is a bis-acylamide-compound of the formula I ##STR98## wherein R.sup.1 and R.sup.2 are hydrogen, alkyl having 1 to 4 carbon atoms or CH.sub.2 OH.
- 20. A method according to claim 16 wherein component (A) is a water-soluble homo- or copolymer having pendant amidocarbonyl groups of the formula --CONH.sub.2 and component (B) is a water-soluble homo- or copolymer having formylamide groups of the formula ##STR99## wherein R.sup.9 is hydrogen or alkyl having 1 to 4 carbon atoms or --CH.sub.2 OH.
- 21. A crosslinkable, water-soluble composition comprising:
- (A) a water-soluble homo- or copolymer having pendant amidocarbonyl groups of the formula --CONH.sub.2 in an amount of more than 10%, calculated on the weight of the polymer and
- (B) a water-soluble homo- or copolymer having 50 to 100% by weight of formylamido entities of the formula VI ##STR100## wherein R.sup.9 stands for hydrogen, methyl or hydroxy methyl and of 0 to 50% by weight of entities of the formula VII ##STR101## wherein R.sup.11 stands for hydrogen or methyl and
- X stands for cyano; the carboxyl group; the alkali or ammonium salts of carboxyl; the alkoxy carbonyl group having 1 to 6 carbon atoms; the hydroxy-alkoxycarbonyl group having 1 to 3 carbon atoms; the N-methylolamidocarbonyl group HOCH.sub.2 NH--CO--; the N-methylolamidocarbonyl group wherein the methylol group is etherified with alkanols having 1 to 4 carbon atoms; the alkanoylamino group having 1 to 4 carbon atoms; the alkanoylamino group having 1 to 4 carbon atoms which is N-substituted with methylol or alkyl having 1 to 4 carbon atoms; pyrrolidonyl-(1); phenyl; pyridinium; the sulfonic acid group; a sulfoalkylamidocarbonyl group having 1 to 4 carbon atoms; the phosphonic acid group; the alkali or ammonium salts of said sulfonic acids and phosphonic acid groups; a radical of the formula VIII ##STR102## wherein R.sup.12 and R.sup.13 are the same or different and stand for alkyl having 1 to 4; a radical of the formula IX ##STR103## wherein p represents a number from 1 to 3; a radical of the formula X ##STR104## wherein R.sup.14 and R.sup.15 are the same or different and stand for alkyl having 1 to 4 carbon atoms; or quaternary salts of formulas IX and X.
- 22. A crosslinkable, water-soluble composition according to claim 21 wherein component (A) comprises 50 to 100% by weight of entities of the formula II ##STR105## wherein R.sup.4 stands for hydrogen or methyl and of 0 to 50% by weight of entities of the formula III ##STR106## wherein R.sup.5 stands for hydrogen, alkyl having 1 to 3 carbon atoms, and
- Y stands for formylamido; N-substituted formylamido where the N-substituent is methyl or hydroxy methyl; cyano; carboxyl; the alkali or ammonium salts of carboxyl; the alkoxycarbonyl group having 1 to 6 carbon atoms; the hydroxy-alkoxycarbonyl group having 1 to 3 carbon atoms; the N-methylolamidocarbonyl group HOCH.sub.2 NH--CO--; the N-methylolamidocarbonyl group wherein the methylol group is etherified with alkanols having 1 to 4 carbon atoms; the mono- or dialkylamino group having altogether 1 to 8 carbon atoms in the alkyl radicals; the alkanoylamino group having 1 to 4 carbon atoms; the alkanoylamino group having 1 to 4 carbon atoms which is N-substituted with methylol or alkyl having 1 to 4 carbon atoms; pyrrolidonyl-(1); phenyl; pyridinium; the sulfonic acid group, the sulfoalkylamidocarbonyl group having 1 to 4 carbon atoms; the phosphonic acid group; the alkali or ammonium salts of said sulfonic acids and phosphonic acid groups; a radical of the formula IV ##STR107## a radical of the formula V ##STR108## wherein R.sup.7 and R.sup.8 are the same or different and stand for alkyl having 1 to 4 carbon atoms and p represents a number from 1 to 3; or quaternary salts of formulas IV and V.
- 23. A cross-linkable, water-soluble composition according to claim 1 wherein component (B) comprises a bis-acylamide compound of the formula (I) ##STR109## wherein R.sup.1 and R.sup.2 are hydrogen, alkyl having 1 to 4 carbon atoms or --CH.sub.2 OH and wherein n represents a number from 1 to 3 and m represents a number from 0 to 1.
- 24. A crosslinkable, water-soluble composition according to claim 23 where the compound of formula I is methylene-bis-formamide or bis-(N-formylaminomethyl)ether.
- 25. A crosslinked polymer composition comprising a homo- or copolymer chain of acrylamide or methacrylamide crosslinked to a second compound to form a polymer network wherein the crosslink bridges have the formula --NR.sup.x --CH.dbd.N--CO-- wherein R.sup.x represents hydrogen, alkyl having 1 to 4 carbon atoms or --CH.sub.2 OH.
- 26. A crosslinked composition according to claim 25 wherein crosslink bridges of the formula --NR.sup.x --CH.dbd.N--CO-- are formed by the reaction in an aqueous acidic medium of a compound having at least two formylamido groups with a homo- or copolymer having at least two amidocarbonyl groups.
Parent Case Info
This application is a continuation of application Ser. No. 216,672 filed Dec. 15, 1980 now abandoned.
US Referenced Citations (21)
Foreign Referenced Citations (3)
Number |
Date |
Country |
0023712 |
Feb 1981 |
EPX |
0044508 |
Jan 1982 |
EPX |
482897 |
Apr 1938 |
GBX |
Non-Patent Literature Citations (2)
Entry |
Copolymerization, edited by George E. Ham, Interscience Publishers. |
Kunststoff-Handbuch, vol. I, "Grundlagen", by Braun, pp.91-95, (1975). |
Continuations (1)
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Number |
Date |
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Parent |
216672 |
Dec 1980 |
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