CN1775825A - 聚天冬酰亚胺 - Google Patents
聚天冬酰亚胺 Download PDFInfo
- Publication number
- CN1775825A CN1775825A CNA2005101250452A CN200510125045A CN1775825A CN 1775825 A CN1775825 A CN 1775825A CN A2005101250452 A CNA2005101250452 A CN A2005101250452A CN 200510125045 A CN200510125045 A CN 200510125045A CN 1775825 A CN1775825 A CN 1775825A
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- China
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- Prior art date
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- Granted
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- 239000005056 polyisocyanate Substances 0.000 claims abstract description 28
- 229920001228 polyisocyanate Polymers 0.000 claims abstract description 28
- 238000000034 method Methods 0.000 claims abstract description 19
- 239000000203 mixture Substances 0.000 claims abstract description 11
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 claims description 19
- 150000001412 amines Chemical class 0.000 claims description 18
- 125000004432 carbon atom Chemical group C* 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 239000008199 coating composition Substances 0.000 claims description 14
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 12
- 125000003118 aryl group Chemical group 0.000 claims description 11
- 229920000570 polyether Polymers 0.000 claims description 11
- 125000003277 amino group Chemical group 0.000 claims description 9
- 229910052799 carbon Inorganic materials 0.000 claims description 9
- 239000003795 chemical substances by application Substances 0.000 claims description 9
- 230000000694 effects Effects 0.000 claims description 9
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 5
- 125000000524 functional group Chemical group 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 abstract description 5
- 150000003923 2,5-pyrrolediones Chemical class 0.000 abstract description 2
- 239000011527 polyurethane coating Substances 0.000 abstract description 2
- 238000006243 chemical reaction Methods 0.000 description 25
- -1 aspartic acid carboxylic acid Chemical group 0.000 description 15
- 239000011248 coating agent Substances 0.000 description 15
- 238000000576 coating method Methods 0.000 description 15
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 12
- 239000002904 solvent Substances 0.000 description 12
- 229940009098 aspartate Drugs 0.000 description 11
- 239000003973 paint Substances 0.000 description 10
- 229920000768 polyamine Polymers 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 7
- 238000005516 engineering process Methods 0.000 description 6
- 150000003141 primary amines Chemical class 0.000 description 6
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical class OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 5
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 5
- 125000001261 isocyanato group Chemical group *N=C=O 0.000 description 5
- 239000011976 maleic acid Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- IEPRKVQEAMIZSS-UHFFFAOYSA-N Di-Et ester-Fumaric acid Natural products CCOC(=O)C=CC(=O)OCC IEPRKVQEAMIZSS-UHFFFAOYSA-N 0.000 description 4
- IEPRKVQEAMIZSS-WAYWQWQTSA-N Diethyl maleate Chemical compound CCOC(=O)\C=C/C(=O)OCC IEPRKVQEAMIZSS-WAYWQWQTSA-N 0.000 description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- RYDVBNBVYVMEDT-UHFFFAOYSA-N n-carbamoyl-2-hydroxyacetamide Chemical group NC(=O)NC(=O)CO RYDVBNBVYVMEDT-UHFFFAOYSA-N 0.000 description 4
- 229920001451 polypropylene glycol Polymers 0.000 description 4
- 150000003335 secondary amines Chemical class 0.000 description 4
- 238000003860 storage Methods 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 239000012948 isocyanate Substances 0.000 description 3
- 238000004448 titration Methods 0.000 description 3
- 229940008841 1,6-hexamethylene diisocyanate Drugs 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- 235000009161 Espostoa lanata Nutrition 0.000 description 2
- 240000001624 Espostoa lanata Species 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 2
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 2
- GHAZCVNUKKZTLG-UHFFFAOYSA-N N-ethyl-succinimide Natural products CCN1C(=O)CCC1=O GHAZCVNUKKZTLG-UHFFFAOYSA-N 0.000 description 2
- HDFGOPSGAURCEO-UHFFFAOYSA-N N-ethylmaleimide Chemical compound CCN1C(=O)C=CC1=O HDFGOPSGAURCEO-UHFFFAOYSA-N 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 150000004705 aldimines Chemical group 0.000 description 2
- 125000002723 alicyclic group Chemical group 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000007697 cis-trans-isomerization reaction Methods 0.000 description 2
- 230000008602 contraction Effects 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 2
- WJRBRSLFGCUECM-UHFFFAOYSA-N hydantoin Chemical compound O=C1CNC(=O)N1 WJRBRSLFGCUECM-UHFFFAOYSA-N 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- 150000002513 isocyanates Chemical class 0.000 description 2
- YDNLNVZZTACNJX-UHFFFAOYSA-N isocyanatomethylbenzene Chemical compound O=C=NCC1=CC=CC=C1 YDNLNVZZTACNJX-UHFFFAOYSA-N 0.000 description 2
- 229940043265 methyl isobutyl ketone Drugs 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- VIKNJXKGJWUCNN-XGXHKTLJSA-N norethisterone Chemical compound O=C1CC[C@@H]2[C@H]3CC[C@](C)([C@](CC4)(O)C#C)[C@@H]4[C@@H]3CCC2=C1 VIKNJXKGJWUCNN-XGXHKTLJSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000004814 polyurethane Substances 0.000 description 2
- 229920002635 polyurethane Polymers 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 2
- YDNMHDRXNOHCJH-REOHCLBHSA-N (3s)-3-aminopyrrolidine-2,5-dione Chemical group N[C@H]1CC(=O)NC1=O YDNMHDRXNOHCJH-REOHCLBHSA-N 0.000 description 1
- ZTNJGMFHJYGMDR-UHFFFAOYSA-N 1,2-diisocyanatoethane Chemical class O=C=NCCN=C=O ZTNJGMFHJYGMDR-UHFFFAOYSA-N 0.000 description 1
- NBIYKOUEZOEMMC-UHFFFAOYSA-N 1-(2-methylpropyl)pyrrole-2,5-dione Chemical compound CC(C)CN1C(=O)C=CC1=O NBIYKOUEZOEMMC-UHFFFAOYSA-N 0.000 description 1
- JNPCNDJVEUEFBO-UHFFFAOYSA-N 1-butylpyrrole-2,5-dione Chemical compound CCCCN1C(=O)C=CC1=O JNPCNDJVEUEFBO-UHFFFAOYSA-N 0.000 description 1
- NKHIHGVHWGKXMQ-UHFFFAOYSA-N 1-ethyl-3-methylpyrrole-2,5-dione Chemical compound CCN1C(=O)C=C(C)C1=O NKHIHGVHWGKXMQ-UHFFFAOYSA-N 0.000 description 1
- VRVUKQWNRPNACD-UHFFFAOYSA-N 1-isocyanatopentane Chemical class CCCCCN=C=O VRVUKQWNRPNACD-UHFFFAOYSA-N 0.000 description 1
- VGDRJOYRXIROMB-UHFFFAOYSA-N 1-methyl-3-(3-methylbutyl)pyrrole-2,5-dione Chemical compound CC(C)CCC1=CC(=O)N(C)C1=O VGDRJOYRXIROMB-UHFFFAOYSA-N 0.000 description 1
- HIDBROSJWZYGSZ-UHFFFAOYSA-N 1-phenylpyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C1=CC=CC=C1 HIDBROSJWZYGSZ-UHFFFAOYSA-N 0.000 description 1
- AIDLAEPHWROGFI-UHFFFAOYSA-N 2-methylbenzene-1,3-dicarboxylic acid Chemical compound CC1=C(C(O)=O)C=CC=C1C(O)=O AIDLAEPHWROGFI-UHFFFAOYSA-N 0.000 description 1
- QBGQIMOGHUXVKB-UHFFFAOYSA-N 2-phenyl-4,5,6,7-tetrahydroisoindole-1,3-dione Chemical compound O=C1C(CCCC2)=C2C(=O)N1C1=CC=CC=C1 QBGQIMOGHUXVKB-UHFFFAOYSA-N 0.000 description 1
- YDNMHDRXNOHCJH-UHFFFAOYSA-N 3-aminopyrrolidine-2,5-dione Chemical compound NC1CC(=O)NC1=O YDNMHDRXNOHCJH-UHFFFAOYSA-N 0.000 description 1
- IDKISNULXBMYIB-UHFFFAOYSA-N 3-hexyl-1-methylpyrrole-2,5-dione Chemical compound CCCCCCC1=CC(=O)N(C)C1=O IDKISNULXBMYIB-UHFFFAOYSA-N 0.000 description 1
- QAVUFFJVZGZJMO-UHFFFAOYSA-N 3-methyl-1-phenylpyrrole-2,5-dione Chemical compound O=C1C(C)=CC(=O)N1C1=CC=CC=C1 QAVUFFJVZGZJMO-UHFFFAOYSA-N 0.000 description 1
- ZLPORNPZJNRGCO-UHFFFAOYSA-N 3-methylpyrrole-2,5-dione Chemical compound CC1=CC(=O)NC1=O ZLPORNPZJNRGCO-UHFFFAOYSA-N 0.000 description 1
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 239000009261 D 400 Substances 0.000 description 1
- 239000005058 Isophorone diisocyanate Substances 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- KYIMHWNKQXQBDG-UHFFFAOYSA-N N=C=O.N=C=O.CCCCCC Chemical compound N=C=O.N=C=O.CCCCCC KYIMHWNKQXQBDG-UHFFFAOYSA-N 0.000 description 1
- QOSMNYMQXIVWKY-UHFFFAOYSA-N Propyl levulinate Chemical compound CCCOC(=O)CCC(C)=O QOSMNYMQXIVWKY-UHFFFAOYSA-N 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical group CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 description 1
- 239000004902 Softening Agent Substances 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 239000004411 aluminium Substances 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 238000005576 amination reaction Methods 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000012296 anti-solvent Substances 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
- CKLJMWTZIZZHCS-REOHCLBHSA-L aspartate group Chemical group N[C@@H](CC(=O)[O-])C(=O)[O-] CKLJMWTZIZZHCS-REOHCLBHSA-L 0.000 description 1
- 235000003704 aspartic acid Nutrition 0.000 description 1
- OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- OHJMTUPIZMNBFR-UHFFFAOYSA-N biuret Chemical group NC(=O)NC(N)=O OHJMTUPIZMNBFR-UHFFFAOYSA-N 0.000 description 1
- 229940043232 butyl acetate Drugs 0.000 description 1
- VPKDCDLSJZCGKE-UHFFFAOYSA-N carbodiimide group Chemical group N=C=N VPKDCDLSJZCGKE-UHFFFAOYSA-N 0.000 description 1
- 150000001728 carbonyl compounds Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000005253 cladding Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N ferric oxide Chemical compound O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000007667 floating Methods 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 1
- 239000004922 lacquer Substances 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- SEEYREPSKCQBBF-UHFFFAOYSA-N n-methylmaleimide Chemical compound CN1C(=O)C=CC1=O SEEYREPSKCQBBF-UHFFFAOYSA-N 0.000 description 1
- 238000010422 painting Methods 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 108010064470 polyaspartate Proteins 0.000 description 1
- 229920005906 polyester polyol Polymers 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 230000037452 priming Effects 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 230000003335 steric effect Effects 0.000 description 1
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical group O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 1
- 238000005829 trimerization reaction Methods 0.000 description 1
- AVWRKZWQTYIKIY-UHFFFAOYSA-N urea-1-carboxylic acid Chemical group NC(=O)NC(O)=O AVWRKZWQTYIKIY-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/30—Low-molecular-weight compounds
- C08G18/38—Low-molecular-weight compounds having heteroatoms other than oxygen
- C08G18/3819—Low-molecular-weight compounds having heteroatoms other than oxygen having nitrogen
- C08G18/3842—Low-molecular-weight compounds having heteroatoms other than oxygen having nitrogen containing heterocyclic rings having at least one nitrogen atom in the ring
- C08G18/3844—Low-molecular-weight compounds having heteroatoms other than oxygen having nitrogen containing heterocyclic rings having at least one nitrogen atom in the ring containing one nitrogen atom in the ring
- C08G18/3846—Low-molecular-weight compounds having heteroatoms other than oxygen having nitrogen containing heterocyclic rings having at least one nitrogen atom in the ring containing one nitrogen atom in the ring containing imide groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/36—Oxygen or sulfur atoms
- C07D207/40—2,5-Pyrrolidine-diones
- C07D207/416—2,5-Pyrrolidine-diones with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to other ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/77—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur
- C08G18/78—Nitrogen
- C08G18/79—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates
- C08G18/791—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing isocyanurate groups
- C08G18/792—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing isocyanurate groups formed by oligomerisation of aliphatic and/or cycloaliphatic isocyanates or isothiocyanates
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
-
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Abstract
本发明涉及一种新型的聚天冬酰亚胺及其制备方法和这些聚天冬酰亚胺作为两组分聚氨酯涂料组合物中的多异氰酸酯的活性组分的应用。该聚天冬酰亚胺由聚醚胺与马来酰亚胺反应来制备。
Description
技术领域
本发明涉及一种新型的聚天冬酰亚胺(polyaspartimide)、一种由具体的伯胺和马来酰亚胺制备它们的方法、以及它们作为两组分聚氨酯涂料组合物中的聚异氰酸酯的活性组分的应用。
背景技术
含有作为粘合剂的多异氰酸酯组分与一种或多种异氰酸酯-活性组分相结合的两组分涂料组合物是已知的。它们适合用于制备坚硬、有弹性、耐磨、耐溶剂和耐侯的高质量涂层。
含有酯基团的聚仲胺已在两组分的表面涂料工业中得到了公认。它们特别适合与漆料多异氰酸酯相结合用作溶剂含量低或不含溶剂、高固体含量的涂料组合物的粘合剂，因为它们提供低温下涂层的快速固化。
这些聚仲胺是聚天冬氨酸酯，在例如美国专利5126170、5214086、5236741、5243012、5364955、5412056、5623045、5736604、6183870、6355829、6458293、6482333和欧洲专利申请公开667362中有描述。另外，含有醛亚胺基团的天冬氨酸酯也是已知的(参见美国专利5489704、5559204和5847195)。仲天冬酸酰胺酯(secondary aspartic acid amide ester)也是已知的(参见美国专利6005062)。它们在两组分涂料组合物中单独用作异氰酸酯-活性组分或与其它异氰酸酯-活性组分混合使用，也描述在上述专利中。制备这些聚天冬氨酸酯的方法是相应的聚伯胺与马来酸酯或延胡索酸酯反应，导致聚仲胺的形成。因为空间效应、结构效应和电子效应，这些聚仲胺基团对于异氰酸酯基团活性有了充足的下降，可以可靠又简易的方法与多异氰酸酯相混合。
如同现有技术中已知的，用于制备聚天冬氨酸酯的反应是伯胺与烯键式羰基化合物中的活性C-C双键的加成反应。但是，已发现该反应在实际的合成工艺过程(例如，60℃下搅拌24小时)中不能进行完全。实际的反应程度取决于伯胺的类型。因此，使用1，6-环己烷二胺在反应1天后的转化度(通过测量游离的、未转化的马来酸酯和延胡索酸酯的浓度来确定，在碱性催化剂存在下，马来酸酯重排成延胡索酸酯)约为90％至93％。而使用具有空间位阻伯胺基团的脂环族多胺，即4，4’-二氨基-3，3’-二甲基二环己基甲烷，在1天后的转化度仅为77％。完全转化或基本上完全转化只能在若干天后才能实现，若是4，4’-二氨基-3，3’-二甲基二环己基甲烷的话，则需要几个月的时间才能完全转化。
在通常的商业生产中，反应进行16个小时，取决于所使用的胺，转化度在75％至95％之间。“未完成的”材料装桶且存储直到反应完全。这通常需要二个星期至六个月不等。美国专利5821326中描述了某种五元芳香环化合物作为催化剂在加快天冬氨酸酯的制备速度中的应用。
常规的天冬氨酸酯能够进一步转化(用异氰酸酯固化后)，形成乙内酰脲环结构。乙内酰脲的形成可导致涂层的收缩和不利的醇的形成。期望制备出一种天冬氨酸酯，其形成乙内酰脲的趋势较小。
于2004年1月21日提交的美国申请序列号10/761643描述了通过将过量的伯胺与马来酸酯或延胡索酸酯反应，然后将所得的产物与马来酰亚胺反应形成一种同时具有天冬氨酸酯基团和天冬酰亚胺基团的产物来制备天冬氨酸酯。
发明内容
本发明涉及一种新型的聚天冬酰亚胺，其通式为：
其中，X代表n价的通过从对应于通式X-(NH2)n的的聚醚胺中除去n个氨基基团得到的聚醚基，其中所述的聚醚胺的数均分子量约为200至6000，并含有其它或者对异氰酸酯基团有反应活性、或者在最高为100℃的温度下对异氰酸酯基团呈惰性的官能团，
R2和R3可等同或不同，代表选自i)、ii)、iii)和iv)的部分：i)氢；ii)直链或支链的C1至C8烷基基团，其最多可被三个含有6至10个碳原子的芳基基团取代；iii)C6至C10芳基基团，其最多可被三个含有1至3个碳原子的烷基基团取代；iv)R2和R3一起形成五元或六元环烷基基团，所述环烷基基团被0到3个含有1至3个碳原子的烷基基团取代；
R1代表选自i)、ii)和iii)的部分：i)氢；ii)直链或支链的C1至C8烷基基团，其最多可被三个含有6至10个碳原子的芳基基团取代；iii)C6至C10芳基基团，其最多可被三个含有1至3个碳原子的烷基基团取代，以及
n代表2至4的整数。
本发明的产物与多异氰酸酯组合时，会具有较长的贮存期，并比现有技术中基于聚醚的天冬氨酸酯提供更为坚硬的涂层，产物形成乙内酰脲环的趋势较小。
本发明还涉及一种制备上述通式的聚天冬酰亚胺的方法，其包括在约室温至约100℃的温度下，在溶液中或在无溶剂的情况下，对应于通式x[-NH2]n的二胺或多胺与马来酰亚胺以马来酰亚胺对氨基基团的当量比为约0.95∶1至约1.05∶1的比例反应，其中X和n如上文所定义。最优的比例为1∶1。
本发明还涉及一种两组分涂料组合物，其含有作为粘合剂的
a)多异氰酸酯组分，和
b)异氰酸酯-活性组分，其含有
b1)对应于本发明的聚天冬酰亚胺的化合物，和
b2)任选的其它异氰酸酯-活性化合物，
其中，异氰酸酯基团对异氰酸酯-活性基团的当量比为约0.8∶1至约2∶1，以及任选的表面涂料技术中已知的添加剂。
具体实施方式
分子量为数均分子量(Mn)，并且由端基分析来确定(NH值)。
合适的多胺对应于现有技术中已知并用于制备异氰酸酯封端预聚物的聚醚多元醇，除了链端的羟基基团转化成了氨基基团，该转化或者是通过氨基化作用，或者是将羟基基团与二异氰酸酯反应、且随后将链端的异氰酸酯基团水解为氨基基团来实现。优选的多胺为氨基封端的聚醚，诸如可从Huntsman公司购得的Jeffamine树脂。
聚醚胺组分包括任何能实现本发明目的的聚醚胺。合适的聚醚胺通常包括具有聚环氧丙烷基团的二官能胺和多官能胺。这些胺是众所周知的，可通过如德国专利公开1193671、美国专利3236895和法国专利1466708中描述的方法来制备，其内容通过引用包括于此。合适的二官能胺的实例为可从Hunstman公司购得的聚环氧丙烷二胺，诸如JeffamineD-230、JeffamineD-400、JeffamineD-2000。合适的三官能聚环氧丙烷胺包括聚氧化丙三胺、(JeffamineT-403)、JeffamineT-3000和JeffamineT-5000，它们也从Huntsman公司购得。据信也可以使用多官能聚醚胺如四官能聚环氧丙烷胺。
有用的马来酰亚胺是那些具有以下结构的马来酰亚胺：
其中，R1、R2和R3如上文所定义。具体有用的马来酰亚胺包括N-甲基马来酰亚胺、N-乙基马来酰亚胺、N-丙基马来酰亚胺、N-异丙基马来酰亚胺、N-异丁基马来酰亚胺、N-丁基马来酰亚胺、N-戊基马来酰亚胺、N-乙基戊基马来酰亚胺、N-甲基异戊基马来酰亚胺、N-甲基己基马来酰亚胺、N-苯基马来酰亚胺、N-乙基-2-甲基马来酰亚胺、N-2，3-三甲基甲基马来酰亚胺、3-甲基-N-苯基马来酰亚胺、N-苯基-3，4，5，6-四氢邻苯二甲酰亚胺和3-苯基-N苯基马来酰亚胺。
反应通常在约50至约100℃的温度下进行约1小时至4小时。马来酰亚胺对胺基基团的当量比为约0.95∶1至约1.05∶1，1∶1的比率为佳。然后可除去任何过量的马来酰亚胺以提供100％树脂产品，或者过量的马来酰亚胺也可以留在产品中并作为增塑剂起作用。如果使用过量的胺，通常是可容许的，但是此类的产品会具有较高的活性，从而缩短了总体系的贮存时间。
制备本发明的聚天冬酰亚胺的方法可在溶液中或无溶剂的情况下实施。溶剂也可在合成过程之后加入，例如，用来降低粘度。合适的溶剂包括任何有机溶剂，优选那些根据表面涂料技术已知不与任何反应参与物反应的溶剂。实例包括乙酸正丁酯、乙酸羟甲基丙酯、甲苯、二甲苯和高级芳香族溶剂(诸如Exxon的Solvesso溶剂)。
依据本发明制备的聚天冬酰亚胺可在合成过程结束后直接用作多异氰酸酯的活性组分。
本发明的聚天冬酰亚胺的一种用途是由两组分涂料组合物制备涂层，该涂料组合物包括作为粘合剂的以下组合
a)多异氰酸酯组分，和
b)异氰酸酯-活性组分，其含有
b1)一种或多种本发明的聚天冬酰亚胺，和
b2)任选的其它已知的异氰酸酯-活性组分。
合适的多异氰酸酯组分a)是已知的且包括聚氨酯化学中已知的多异氰酸酯，例如，低分子量的多异氰酸酯和由这些低分子量的多异氰酸酯制得的漆料多异氰酸酯(lacquer polyisocyanate)。优选的是表面涂料技术中已知的漆料多异氰酸酯。这些漆料多异氰酸酯可含有缩二脲基团、异氰尿酸酯基团、脲基甲酸酯基团、脲二酮基团、碳二亚胺基团和/或氨基甲酸乙酯基团，并优选由脂环族多异氰酸酯制备得到。
适用于本发明的、或用于制备漆料多异氰酸酯的低分子量多异氰酸酯是那些分子量为140至300的多异氰酸酯，诸如1，4-四亚甲基二异氰酸酯、1，6-六亚甲基二异氰酸酯(HDI)、2，2，4-和/或2，4，4-三甲基-六亚甲基二异氰酸酯、十二亚甲基二异氰酸酯、2-甲基-1，5-二异氰酸基戊烷、1，4-二异氰酸基环己烷、1-异氰酸基-3，3，5-三甲基-5-异氰酸基-甲基环己烷(IPDI)、2，4-和/或4，4’-二异氰酸基-二环己基甲烷、1-异氰酸基-1-甲基-3(4)-异氰酸基甲基环己烷(IMIC)、2，4-和/或2，6-六氢甲代亚苯基二异氰酸酯(H6TDI)、2，4-和/或4，4’-二异氰酸基二苯基甲烷或这些同分异构体与它们的高级同系物(可通过已知的方法由苯胺/甲醛的缩合产物的光气化作用得到)的混合物、2，4-和/或2，6-二异氰酸基甲苯、和它们的混合物。使用低分子量的多异氰酸酯本身不是首选。同样，使用由芳族多异氰酸酯如2，4-和/或2，6-二异氰酸基甲苯制得的漆料多异氰酸酯也不怎么好。含有氨基甲酸乙酯基团的漆料多异氰酸酯最好是基于分子量为62至300的低分子量多元醇化合物，诸如乙二醇、丙二醇和/或三羟甲基丙烷。
优选的用作组分a)的漆料多异氰酸酯是那些基于1，6-六亚甲基二异氰酸酯、NCO含量为16重量％至24重量％、23℃下最大粘度为10000毫帕秒-较优的为3000毫帕秒的多异氰酸酯。优选的还有那些基于TPDI的异氰酸酯。
任选的原料组分b2)是已知的含有至少两个异氰酸酯-活性基团的化合物，异氰酸酯-活性基团包括在受潮或/和受热的效应下可与异氰酸酯基团反应的基团。实例包括羟基官能聚丙烯酸酯、聚酯多元醇和聚醚多元醇和现有技术中已知类型的天冬氨酸酯和醛亚胺。也可以使用这些化合物的混合物。
依据本发明，对在粘合剂中使用的组分a)、b1)和(任选的)b2)的量加以选择以使异氰酸酯基团对异氰酸酯-活性基团的当量比为约0.8∶1至约2.0∶1，较优的约0.8∶1至约1.2∶1。
依据本发明，粘合剂的制备方法是在没有溶剂的情况下、或者是在聚氨酯表面涂料技术中常用的溶剂存在下，将各个组分混合。合适的溶剂包括乙酸乙酯、乙酸丁酯、乙酸甲氧基丙酯、甲基异丁基酮、甲基乙基酮、二甲苯、N-甲基吡咯烷酮、石油溶剂油、氯苯、Solvesso溶剂或它们的混合物。
优选地，根据本发明，粘合剂组分a)和b)对涂料组合物中的溶剂的重量比为约40∶60至约100∶0，约60∶40至约100∶0更佳。
涂料组合物还可以含有表面涂料技术中已知的添加剂。这些添加剂包括颜料、填充物、流动控制剂、催化剂和防沉降剂。
由依据本发明的涂料组合物制得的涂层性质可通过适当选择原料组分a)、b1)和b2)的类型和比率来调节。
涂料组合物可通过任何已知的方法以单层或多层的形式施涂到任何基材上，例如，通过喷涂、涂漆、浸渍、浮涂(flood)或使用辊或涂布机来施涂。依据本发明的涂料组合物适用于在基材上制备涂层，诸如在金属、塑料、木材或玻璃上。涂料组合物特别适用于涂敷用来生产车身、机器、外挂板、桶和容器的不锈钢板材。在施涂本发明的涂料组合物之前，可先给基材上合适的底漆。涂层的干燥可在约0至160℃的温度下进行。
本发明的聚天冬酰亚胺可在合成过程完成后直接使用，因为与现有技术的天冬氨酸酯相比，可以达到几乎百分之百的转化度。产物对异氰酸酯表现出合理的而不是剧烈的活性。因为它们粘度低，所以，作为活性稀释剂，它们远不只是以前使用的污染环境的有机溶剂的合适的替代品，因此使用在高质量、低溶剂或甚至不含溶剂的、高固体的两组分涂料组合中。
马来酰亚胺的反应比马来酸二烷基酯要快得多，这是因为在马来酰亚胺中不可能发生顺反异构化，而顺反异构化出现在马来酸酯异构化为延胡索酸酯时，且使反应缓慢。这是一个优势，因为减少了合成时间且消除了老化过程。另一个优势在于琥珀酰亚胺部分不能象天冬氨酸酯一样进一步转化(在用异氰酸酯固化后)形成乙内酰脲环结构。此类乙内酰脲环的形成伴随着醇的脱去，这会导致涂层的收缩。而本技术的另一个优势在于可能形成基于如Jeffamine多胺之类的慢胺(slow amine)天冬酰亚胺。令人惊喜的是，与Jeffamine多胺和马来酸二乙酯的反应相比，基于Jeffamine多胺和马来酰亚胺的产物可在短时间内完全形成。与马来酸二乙酯和Jeffamine多胺的反应相比，马来酰亚胺与Jeffamine多胺的反应可在数个小时内反应完全，而马来酸二乙酯和Jeffamine多胺的反应如此之慢以致于6个月内只有50％转化为天冬氨酸酯。这给更为灵活地合成天冬氨酸酯类共反应物提供了可能性。
如无相反指示，以下实施例中所有的份数和百分数都以重量计。
实施例
胺1是JeffamineT-3000。
胺2-给一圆底烧瓶配置搅拌器、加热罩、氮气进口、热电偶和加料漏斗。在室温下向烧瓶中加入1170份(1.0当量)的JeffamineT-3000。然后加入125.13份(1.0当量)的N-乙基马来酰亚胺。烧瓶的温度上升到60℃。然后将反应在60℃保持24小时，此时碘量滴定表明反应进行完全。反应混合物冷却至室温。透明的近无色的最终产物的粘度为1420厘泊，胺值为46.9：(理论胺值：43.3)。
对比例-给一圆底烧瓶配置搅拌器、加热罩、氮气进口、热电偶和加料漏斗。在室温下向烧瓶中加入500份(0.5当量)的JeffamineT-3000。然后加入62.6份(0.5当量)的马来酸二乙酯。烧瓶的温度上升到60℃。然后将反应在60℃保持24小时，此时碘量滴定表明反应只完成了24％。将反应混合物冷却并在室温下保持2个月，此时碘量滴定表明向天冬氨酸酯的转化只完成了50％。
将实施例1中的样品与Desmodur N-3300(NCO含量为21.8重量％、当量重量为192的三聚己烷二异氰酸酯)以(NCO∶NH)比率为1的指数手工混合。在Brookfield粘度计上测量粘度。样品干燥时间通过对混合样品在玻璃上进行刮涂来测量。样品以10密耳湿进行刮涂。每隔2分钟，将一棉球压在刮涂面上以测试膜的固化。当棉球不留下印迹时，样品膜即完全固化。Shore D硬度通过将混合样品倒入铝杯中并在3天后用D-2型Shore硬度计按ASTM D2240来测量。
| 产物 | 干燥时间(分钟) | 贮存时间 | Shore D(混合后3天) | 膜外观 |
| 实施例1 | 25 | 10 | 13 | 透明 |
| 胺1 | - | ＜＜10秒* | - | - |
| *太快以致于无法准备测试样 | ||||
虽然在前文中为了举例说明的目的对本发明进行了详细的描述，但应理解，这些详细描写仅仅是为了该目的，本领域一般技术人员可对其进行修改，而不背离本发明的精神和范围，除由权利要求书所限制者。
Claims (5)
1.一种如下式所示的聚天冬酰亚胺：
其中，X代表n价的聚醚基，所述聚醚基为通过从对应于通式X-(NH2)n的聚醚胺中除去n个氨基基团所得，其中所述聚醚胺的数均分子量为约200至约6000，并可含有其它官能团，所述的官能团或者对异氰酸酯基团有反应活性、或者在最高为100℃的温度下对异氰酸酯基团呈惰性，
R2和R3可等同或不同，并代表选自下组的部分：i)氢；ii)直链或支链的C1至C8烷基基团，所述烷基基团可最多被三个含有6至10个碳原子的芳基基团所取代；iii)C6至C10芳基基团，所述芳基基团可最多被三个含有1至3个碳原子的烷基基团所取代；和iv)R2和R3一起形成五元或六元的环烷基基团，所述环烷基基团被0到3个含有1至3个碳原子的烷基基团所取代，
R1代表选自下组的部分：i)氢；ii)直链或支链的C1至C8烷基基团，所述烷基基团可最多被三个含有6至10个碳原子的芳基基团取代的；iii)C6至C10芳基基团，所述芳基基团可最多被三个含有1至3个碳原子的烷基基团所取代，以及
n代表2至4的整数。
2.一种制备如下式所示的聚天冬酰亚胺的方法：
其中，X代表n价的聚醚基，所述聚醚基为通过从对应于通式X-(NH2)n的聚醚胺中除去n个氨基基团所得，其中所述聚醚胺的数均分子量为约200至约6000，并可含有其它官能团，所述的官能团或者对异氰酸酯基团有反应活性、或者在最高为100℃的温度下对异氰酸酯基团呈惰性，
R2和R3可等同或不同，并代表选自下组的部分：i)氢；ii)直链或支链的C1至C8烷基基团，所述烷基基团可最多被三个含有6至10个碳原子的芳基基团所取代；iii)C6至C10芳基基团，所述芳基基团可最多被三个含有1至3个碳原子的烷基基团所取代；和iv)R2和R3一起形成五元或六元的环烷基基团，所述环烷基基团被0到3个含有1至3个碳原子的烷基基团所取代，
R1代表选自下组的部分：i)氢；ii)直链或支链的C1至C8烷基基团，所述烷基基团可最多被三个含有6至10个碳原子的芳基基团取代的；iii)C6至C10芳基基团，所述芳基基团可最多被三个含有1至3个碳原子的烷基基团所取代，以及
n代表2至4的整数，所述方法包括：在约室温至约100℃的温度下，在溶液中或在无溶剂的情况下，使式X[-NH2]n所示的胺以马来酰亚胺对氨基基团的当量比为约0.95∶1至约1.05∶1的比例发生反应，其中X和n如上所定义。
3.如权利要求2所述的方法，其特征在于，所述马来酰亚胺如下式所示：
其中，R1、R2和R3如上所定义。
4.如权利要求2所述的方法，其特征在于，所述马来酰亚胺对胺基基团的当量比为1∶1。
5.一种两组分涂料组合物，所述组合物含有作为粘合剂的以下组合：
a)多异氰酸酯组分，和
b)异氰酸酯-活性组分，所述异氰酸酯-活性组分含有
b1)权利要求1所述的聚天冬酰亚胺，
b2)任选的其它异氰酸酯-活性化合物，
其中，异氰酸酯基团对异氰酸酯-活性基团的当量比为约O.8∶1至约2.0∶1。
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| CN105462598A (zh) * | 2014-09-25 | 2016-04-06 | 奇美实业股份有限公司 | 液晶取向剂、液晶取向膜以及液晶显示元件 |
| CN113912840A (zh) * | 2021-08-25 | 2022-01-11 | 浙江艾特普科技有限公司 | 一种中空玻璃微珠改性聚天门冬氨酸酯的制备方法及应用 |
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| US20090165676A1 (en) * | 2007-12-26 | 2009-07-02 | E.I. Du Pont De Nemours And Company | Bis(n-silylalkyl)aspartimides and processes therefor |
| US20100063241A1 (en) * | 2008-09-09 | 2010-03-11 | Spirit Aerosystems, Inc. | High performance polyaspartimide resin |
| US20220089901A1 (en) * | 2020-09-24 | 2022-03-24 | Covestro Llc | Clear coating compositions having low solvent content |
| CN117510831A (zh) * | 2023-11-08 | 2024-02-06 | 南京维新高分子科技有限公司 | 水可分散的聚天门冬氨酸酯树脂及水性汽车罩光清漆及其制备方法、应用 |
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| EP0667362A1 (en) | 1994-02-09 | 1995-08-16 | Bayer Corporation | Polyurea coating compositions having improved pot lives |
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| US5489704A (en) | 1994-08-29 | 1996-02-06 | Bayer Corporation | Polyisocyanate/polyamine mixtures and their use for the production of polyurea coatings |
| EP0816326B1 (de) | 1996-07-02 | 2000-05-10 | Bayer Ag | Verfahren zur Herstellung von Mono- und Polyasparaginsäureestern |
| US5736604A (en) | 1996-12-17 | 1998-04-07 | Bayer Corporation | Aqueous, two-component polyurea coating compositions |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105462598A (zh) * | 2014-09-25 | 2016-04-06 | 奇美实业股份有限公司 | 液晶取向剂、液晶取向膜以及液晶显示元件 |
| CN105462598B (zh) * | 2014-09-25 | 2017-11-24 | 奇美实业股份有限公司 | 液晶取向剂、液晶取向膜以及液晶显示元件 |
| CN113912840A (zh) * | 2021-08-25 | 2022-01-11 | 浙江艾特普科技有限公司 | 一种中空玻璃微珠改性聚天门冬氨酸酯的制备方法及应用 |
| CN113912840B (zh) * | 2021-08-25 | 2023-06-23 | 浙江艾特普科技有限公司 | 一种中空玻璃微珠改性聚天门冬氨酸酯的制备方法及应用 |
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| ATE434606T1 (de) | 2009-07-15 |
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| TWI350283B (en) | 2011-10-11 |
| CA2527069A1 (en) | 2006-05-16 |
| CA2527069C (en) | 2014-04-08 |
| US20060106194A1 (en) | 2006-05-18 |
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| DK1666461T3 (da) | 2009-10-05 |
| US7307140B2 (en) | 2007-12-11 |
| DE602005015072D1 (de) | 2009-08-06 |
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| JP4950477B2 (ja) | 2012-06-13 |
| JP2006144012A (ja) | 2006-06-08 |
| EP1666461A3 (en) | 2006-11-29 |
| KR101232559B1 (ko) | 2013-02-12 |
| EP1666461A2 (en) | 2006-06-07 |
| HK1088347A1 (en) | 2006-11-03 |
| EP1666461B1 (en) | 2009-06-24 |
| TW200631937A (en) | 2006-09-16 |
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