DE60009689T2 - Polyaldimines of oligomeric aminobenzoic acid derivatives, and their use for preparation of moisture-curable, storage-stable, one-part polyureas - Google Patents
Polyaldimines of oligomeric aminobenzoic acid derivatives, and their use for preparation of moisture-curable, storage-stable, one-part polyureas Download PDFInfo
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- DE60009689T2 DE60009689T2 DE60009689T DE60009689T DE60009689T2 DE 60009689 T2 DE60009689 T2 DE 60009689T2 DE 60009689 T DE60009689 T DE 60009689T DE 60009689 T DE60009689 T DE 60009689T DE 60009689 T2 DE60009689 T2 DE 60009689T2
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- Germany
- Prior art keywords
- composition
- group
- polyisocyanate
- aromatic
- composition according
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 238000002360 preparation method Methods 0.000 title claims 3
- 150000005417 aminobenzoic acid derivatives Chemical class 0.000 title 1
- 239000000203 mixture Substances 0.000 claims abstract description 50
- -1 heterocyclic aryl radical Chemical group 0.000 claims abstract description 38
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 8
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 8
- 125000004414 alkyl thio group Chemical group 0.000 claims abstract description 7
- 229910052736 halogen Chemical group 0.000 claims abstract description 6
- 229920001228 polyisocyanate Polymers 0.000 claims description 28
- 239000005056 polyisocyanate Substances 0.000 claims description 26
- 125000003118 aryl group Chemical group 0.000 claims description 22
- 238000000034 method Methods 0.000 claims description 16
- UCHUCWHZVSIPQI-UHFFFAOYSA-N 4-(4-aminobenzoyl)oxybutyl 4-aminobenzoate Chemical compound C1=CC(N)=CC=C1C(=O)OCCCCOC(=O)C1=CC=C(N)C=C1 UCHUCWHZVSIPQI-UHFFFAOYSA-N 0.000 claims description 13
- 150000001875 compounds Chemical class 0.000 claims description 12
- 229910052751 metal Inorganic materials 0.000 claims description 12
- 239000002184 metal Substances 0.000 claims description 12
- 239000000654 additive Substances 0.000 claims description 11
- 238000000576 coating method Methods 0.000 claims description 11
- 239000003086 colorant Substances 0.000 claims description 11
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 10
- 238000002156 mixing Methods 0.000 claims description 10
- 239000000843 powder Substances 0.000 claims description 10
- 239000002904 solvent Substances 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 9
- 229920002635 polyurethane Polymers 0.000 claims description 9
- 238000003860 storage Methods 0.000 claims description 9
- 239000011248 coating agent Substances 0.000 claims description 8
- 239000000945 filler Substances 0.000 claims description 8
- 239000003973 paint Substances 0.000 claims description 8
- 239000004014 plasticizer Substances 0.000 claims description 8
- 239000003381 stabilizer Substances 0.000 claims description 8
- 239000013008 thixotropic agent Substances 0.000 claims description 8
- 239000003139 biocide Substances 0.000 claims description 7
- 239000004202 carbamide Substances 0.000 claims description 7
- 239000000463 material Substances 0.000 claims description 7
- ZRSNZINYAWTAHE-UHFFFAOYSA-N p-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C=C1 ZRSNZINYAWTAHE-UHFFFAOYSA-N 0.000 claims description 7
- 239000004814 polyurethane Substances 0.000 claims description 7
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 6
- 150000001299 aldehydes Chemical class 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 6
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- 239000002671 adjuvant Substances 0.000 claims description 5
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 claims description 4
- 150000001735 carboxylic acids Chemical class 0.000 claims description 4
- 150000002367 halogens Chemical group 0.000 claims description 4
- 229920000768 polyamine Polymers 0.000 claims description 4
- 150000003460 sulfonic acids Chemical class 0.000 claims description 4
- 239000000853 adhesive Substances 0.000 claims description 3
- 230000001070 adhesive effect Effects 0.000 claims description 3
- 230000003373 anti-fouling effect Effects 0.000 claims description 3
- 239000012298 atmosphere Substances 0.000 claims description 3
- 238000009408 flooring Methods 0.000 claims description 3
- UIFVCPMLQXKEEU-UHFFFAOYSA-N 2,3-dimethylbenzaldehyde Chemical compound CC1=CC=CC(C=O)=C1C UIFVCPMLQXKEEU-UHFFFAOYSA-N 0.000 claims description 2
- FSMCOBJDZVRWIZ-UHFFFAOYSA-N 2-butoxybenzaldehyde Chemical compound CCCCOC1=CC=CC=C1C=O FSMCOBJDZVRWIZ-UHFFFAOYSA-N 0.000 claims description 2
- QWYIWOLZHRIGCX-UHFFFAOYSA-N 2-decoxybenzaldehyde Chemical compound CCCCCCCCCCOC1=CC=CC=C1C=O QWYIWOLZHRIGCX-UHFFFAOYSA-N 0.000 claims description 2
- FKZSPBKGUNSVCV-UHFFFAOYSA-N 2-dodecoxybenzaldehyde Chemical compound CCCCCCCCCCCCOC1=CC=CC=C1C=O FKZSPBKGUNSVCV-UHFFFAOYSA-N 0.000 claims description 2
- NTWBHJYRDKBGBR-UHFFFAOYSA-N 2-ethylbenzaldehyde Chemical compound CCC1=CC=CC=C1C=O NTWBHJYRDKBGBR-UHFFFAOYSA-N 0.000 claims description 2
- CSDSSGBPEUDDEE-UHFFFAOYSA-N 2-formylpyridine Chemical compound O=CC1=CC=CC=N1 CSDSSGBPEUDDEE-UHFFFAOYSA-N 0.000 claims description 2
- YTWQTYKKFWMTBK-UHFFFAOYSA-N 2-hexadecoxybenzaldehyde Chemical compound CCCCCCCCCCCCCCCCOC1=CC=CC=C1C=O YTWQTYKKFWMTBK-UHFFFAOYSA-N 0.000 claims description 2
- IFOIDROUJIGQAV-UHFFFAOYSA-N 2-hexoxybenzaldehyde Chemical compound CCCCCCOC1=CC=CC=C1C=O IFOIDROUJIGQAV-UHFFFAOYSA-N 0.000 claims description 2
- DTALCVXXATYTQJ-UHFFFAOYSA-N 2-propan-2-ylbenzaldehyde Chemical compound CC(C)C1=CC=CC=C1C=O DTALCVXXATYTQJ-UHFFFAOYSA-N 0.000 claims description 2
- JRHHJNMASOIRDS-UHFFFAOYSA-N 4-ethoxybenzaldehyde Chemical compound CCOC1=CC=C(C=O)C=C1 JRHHJNMASOIRDS-UHFFFAOYSA-N 0.000 claims description 2
- 229920001730 Moisture cure polyurethane Polymers 0.000 claims description 2
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 claims description 2
- 235000011007 phosphoric acid Nutrition 0.000 claims description 2
- 150000003016 phosphoric acids Chemical class 0.000 claims description 2
- 229920005862 polyol Polymers 0.000 claims description 2
- 150000003077 polyols Chemical class 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims 3
- 238000007789 sealing Methods 0.000 claims 2
- 125000001931 aliphatic group Chemical group 0.000 claims 1
- YFNONBGXNFCTMM-UHFFFAOYSA-N butoxybenzene Chemical group CCCCOC1=CC=CC=C1 YFNONBGXNFCTMM-UHFFFAOYSA-N 0.000 claims 1
- VPKDCDLSJZCGKE-UHFFFAOYSA-N carbodiimide group Chemical group N=C=N VPKDCDLSJZCGKE-UHFFFAOYSA-N 0.000 claims 1
- 125000002541 furyl group Chemical group 0.000 claims 1
- 238000010422 painting Methods 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 229920002396 Polyurea Polymers 0.000 abstract description 10
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 239000000049 pigment Substances 0.000 description 14
- 238000004040 coloring Methods 0.000 description 13
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 229920000642 polymer Polymers 0.000 description 8
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 6
- 150000004705 aldimines Chemical class 0.000 description 5
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- 150000003934 aromatic aldehydes Chemical class 0.000 description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
- 230000007062 hydrolysis Effects 0.000 description 4
- 238000006460 hydrolysis reaction Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- NRCMAYZCPIVABH-UHFFFAOYSA-N Quinacridone Chemical compound N1C2=CC=CC=C2C(=O)C2=C1C=C1C(=O)C3=CC=CC=C3NC1=C2 NRCMAYZCPIVABH-UHFFFAOYSA-N 0.000 description 3
- MYONAGGJKCJOBT-UHFFFAOYSA-N benzimidazol-2-one Chemical compound C1=CC=CC2=NC(=O)N=C21 MYONAGGJKCJOBT-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 238000002329 infrared spectrum Methods 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 0 *c(cc1)ccc1N* Chemical compound *c(cc1)ccc1N* 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 239000005711 Benzoic acid Substances 0.000 description 2
- IRIAEXORFWYRCZ-UHFFFAOYSA-N Butylbenzyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCC1=CC=CC=C1 IRIAEXORFWYRCZ-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 2
- 150000004056 anthraquinones Chemical class 0.000 description 2
- DMEGYFMYUHOHGS-UHFFFAOYSA-N cycloheptane Chemical compound C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 2
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 235000019239 indanthrene blue RS Nutrition 0.000 description 2
- UHOKSCJSTAHBSO-UHFFFAOYSA-N indanthrone blue Chemical compound C1=CC=C2C(=O)C3=CC=C4NC5=C6C(=O)C7=CC=CC=C7C(=O)C6=CC=C5NC4=C3C(=O)C2=C1 UHOKSCJSTAHBSO-UHFFFAOYSA-N 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 2
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000003566 sealing material Substances 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- YEVQZPWSVWZAOB-UHFFFAOYSA-N 2-(bromomethyl)-1-iodo-4-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=C(I)C(CBr)=C1 YEVQZPWSVWZAOB-UHFFFAOYSA-N 0.000 description 1
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 description 1
- ALKCLFLTXBBMMP-UHFFFAOYSA-N 3,7-dimethylocta-1,6-dien-3-yl hexanoate Chemical compound CCCCCC(=O)OC(C)(C=C)CCC=C(C)C ALKCLFLTXBBMMP-UHFFFAOYSA-N 0.000 description 1
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 1
- WZSFTHVIIGGDOI-UHFFFAOYSA-N 4,5,6,7-tetrachloro-3-[2-methyl-3-[(4,5,6,7-tetrachloro-3-oxoisoindol-1-yl)amino]anilino]isoindol-1-one Chemical compound ClC1=C(Cl)C(Cl)=C(Cl)C2=C1C(NC1=CC=CC(NC=3C4=C(C(=C(Cl)C(Cl)=C4Cl)Cl)C(=O)N=3)=C1C)=NC2=O WZSFTHVIIGGDOI-UHFFFAOYSA-N 0.000 description 1
- 229940086681 4-aminobenzoate Drugs 0.000 description 1
- ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 description 1
- CGLVZFOCZLHKOH-UHFFFAOYSA-N 8,18-dichloro-5,15-diethyl-5,15-dihydrodiindolo(3,2-b:3',2'-m)triphenodioxazine Chemical compound CCN1C2=CC=CC=C2C2=C1C=C1OC3=C(Cl)C4=NC(C=C5C6=CC=CC=C6N(C5=C5)CC)=C5OC4=C(Cl)C3=NC1=C2 CGLVZFOCZLHKOH-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 229910000906 Bronze Inorganic materials 0.000 description 1
- RHFJVTCOXRBNDP-UHFFFAOYSA-N COC1=CC=C(CC=NC(C=C2)=CC=C2C(OCCCCOC(C(C=C2)=CC=C2N=CCC(C=C2)=CC=C2OC)=O)=O)C=C1 Chemical compound COC1=CC=C(CC=NC(C=C2)=CC=C2C(OCCCCOC(C(C=C2)=CC=C2N=CCC(C=C2)=CC=C2OC)=O)=O)C=C1 RHFJVTCOXRBNDP-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- MQIUGAXCHLFZKX-UHFFFAOYSA-N Di-n-octyl phthalate Natural products CCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCC MQIUGAXCHLFZKX-UHFFFAOYSA-N 0.000 description 1
- ZVFDTKUVRCTHQE-UHFFFAOYSA-N Diisodecyl phthalate Chemical compound CC(C)CCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCC(C)C ZVFDTKUVRCTHQE-UHFFFAOYSA-N 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 229920001328 Polyvinylidene chloride Polymers 0.000 description 1
- 239000006087 Silane Coupling Agent Substances 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 1
- 229910021536 Zeolite Inorganic materials 0.000 description 1
- 238000010521 absorption reaction Methods 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
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- DIZPMCHEQGEION-UHFFFAOYSA-H aluminium sulfate (anhydrous) Chemical compound [Al+3].[Al+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O DIZPMCHEQGEION-UHFFFAOYSA-H 0.000 description 1
- CEGOLXSVJUTHNZ-UHFFFAOYSA-K aluminium tristearate Chemical compound [Al+3].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CEGOLXSVJUTHNZ-UHFFFAOYSA-K 0.000 description 1
- 229940063655 aluminum stearate Drugs 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- HIFVAOIJYDXIJG-UHFFFAOYSA-N benzylbenzene;isocyanic acid Chemical class N=C=O.N=C=O.C=1C=CC=CC=1CC1=CC=CC=C1 HIFVAOIJYDXIJG-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- BJQHLKABXJIVAM-UHFFFAOYSA-N bis(2-ethylhexyl) phthalate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)OCC(CC)CCCC BJQHLKABXJIVAM-UHFFFAOYSA-N 0.000 description 1
- ZFMQKOWCDKKBIF-UHFFFAOYSA-N bis(3,5-difluorophenyl)phosphane Chemical compound FC1=CC(F)=CC(PC=2C=C(F)C=C(F)C=2)=C1 ZFMQKOWCDKKBIF-UHFFFAOYSA-N 0.000 description 1
- OHJMTUPIZMNBFR-UHFFFAOYSA-N biuret Chemical compound NC(=O)NC(N)=O OHJMTUPIZMNBFR-UHFFFAOYSA-N 0.000 description 1
- 239000010974 bronze Substances 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 150000001718 carbodiimides Chemical class 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 229910000423 chromium oxide Inorganic materials 0.000 description 1
- 239000008119 colloidal silica Substances 0.000 description 1
- KUNSUQLRTQLHQQ-UHFFFAOYSA-N copper tin Chemical compound [Cu].[Sn] KUNSUQLRTQLHQQ-UHFFFAOYSA-N 0.000 description 1
- XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- PUFGCEQWYLJYNJ-UHFFFAOYSA-N didodecyl benzene-1,2-dicarboxylate Chemical compound CCCCCCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCCCCCC PUFGCEQWYLJYNJ-UHFFFAOYSA-N 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- PPSZHCXTGRHULJ-UHFFFAOYSA-N dioxazine Chemical compound O1ON=CC=C1 PPSZHCXTGRHULJ-UHFFFAOYSA-N 0.000 description 1
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 150000002484 inorganic compounds Chemical class 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- PXZQEOJJUGGUIB-UHFFFAOYSA-N isoindolin-1-one Chemical compound C1=CC=C2C(=O)NCC2=C1 PXZQEOJJUGGUIB-UHFFFAOYSA-N 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- CWQXQMHSOZUFJS-UHFFFAOYSA-N molybdenum disulfide Chemical compound S=[Mo]=S CWQXQMHSOZUFJS-UHFFFAOYSA-N 0.000 description 1
- 229910052982 molybdenum disulfide Inorganic materials 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229910052755 nonmetal Inorganic materials 0.000 description 1
- ZZSIDSMUTXFKNS-UHFFFAOYSA-N perylene red Chemical compound CC(C)C1=CC=CC(C(C)C)=C1N(C(=O)C=1C2=C3C4=C(OC=5C=CC=CC=5)C=1)C(=O)C2=CC(OC=1C=CC=CC=1)=C3C(C(OC=1C=CC=CC=1)=CC1=C2C(C(N(C=3C(=CC=CC=3C(C)C)C(C)C)C1=O)=O)=C1)=C2C4=C1OC1=CC=CC=C1 ZZSIDSMUTXFKNS-UHFFFAOYSA-N 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 239000005033 polyvinylidene chloride Substances 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000013535 sea water Substances 0.000 description 1
- 239000000565 sealant Substances 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/02—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups
- C07C251/24—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups having carbon atoms of imino groups bound to carbon atoms of six-membered aromatic rings
-
- 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
- C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
- C08G18/3225—Polyamines
- C08G18/3253—Polyamines being in latent form
- C08G18/3256—Reaction products of polyamines with aldehydes or ketones
-
- 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
- C08G18/40—High-molecular-weight compounds
- C08G18/48—Polyethers
- C08G18/50—Polyethers having heteroatoms other than oxygen
- C08G18/5021—Polyethers having heteroatoms other than oxygen having nitrogen
- C08G18/5024—Polyethers having heteroatoms other than oxygen having nitrogen containing primary and/or secondary amino groups
- C08G18/503—Polyethers having heteroatoms other than oxygen having nitrogen containing primary and/or secondary amino groups being in latent form
-
- 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
- C08G2115/00—Oligomerisation
- C08G2115/06—Oligomerisation to carbodiimide or uretone-imine groups
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31551—Of polyamidoester [polyurethane, polyisocyanate, polycarbamate, etc.]
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31551—Of polyamidoester [polyurethane, polyisocyanate, polycarbamate, etc.]
- Y10T428/31605—Next to free metal
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Polyurethanes Or Polyureas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Epoxy Resins (AREA)
- Medicinal Preparation (AREA)
- Furan Compounds (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IL12958399A IL129583A (en) | 1999-04-25 | 1999-04-25 | Diesters of oligobutyleneglycol and amidine benzoic acid and their use for preparation of moisture-curable, storage-stable, one-part polyurethane/urea compositions |
| IL12958399 | 1999-04-25 | ||
| PCT/IL2000/000237 WO2000064860A1 (en) | 1999-04-25 | 2000-04-23 | Polyaldimines of oligomeric aminobenzoic acid derivatives, and their use for preparation of moisture-curable, storage-stable, one-part polyreas |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE60009689D1 DE60009689D1 (de) | 2004-05-13 |
| DE60009689T2 true DE60009689T2 (de) | 2005-06-02 |
Family
ID=11072726
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE60009689T Expired - Fee Related DE60009689T2 (de) | 1999-04-25 | 2000-04-23 | Polyaldimines of oligomeric aminobenzoic acid derivatives, and their use for preparation of moisture-curable, storage-stable, one-part polyureas |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US6552155B1 (enExample) |
| EP (1) | EP1173411B1 (enExample) |
| JP (2) | JP2002543221A (enExample) |
| AT (1) | ATE263749T1 (enExample) |
| AU (1) | AU3986700A (enExample) |
| CA (1) | CA2371224A1 (enExample) |
| DE (1) | DE60009689T2 (enExample) |
| DK (1) | DK1173411T3 (enExample) |
| ES (1) | ES2220452T3 (enExample) |
| IL (1) | IL129583A (enExample) |
| MX (1) | MXPA01010801A (enExample) |
| PT (1) | PT1173411E (enExample) |
| WO (1) | WO2000064860A1 (enExample) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1384735A1 (de) * | 2002-07-26 | 2004-01-28 | Sika Technology AG | Polyaldimin enthaltende Polyurethanzusammensetzung |
| US20060216267A1 (en) * | 2002-08-20 | 2006-09-28 | Kovacs Stephen G | Hydrophobic elastomeric polymer chemistry device for inhibiting the growth of onychomycosis and urushiol-induced allergic contact dermatitis |
| US7572461B2 (en) * | 2004-03-05 | 2009-08-11 | Kenneth I. Sawyer | Borer-resistant wood, wood products, and wooden structures and methods |
| CA2566605A1 (en) * | 2004-05-14 | 2005-12-01 | Kenneth I. Sawyer | Polyurea compositions and compounds for the preparation thereof |
| EP1876196A1 (de) * | 2006-06-30 | 2008-01-09 | Sika Technology AG | VOC-freie oder VOC-arme Polyurethanbeschichtung |
| US8771725B2 (en) * | 2007-10-12 | 2014-07-08 | Chesson Laboratory Associates, Inc. | Poly(urea-urethane) compositions useful as topical medicaments and methods of using the same |
| KR101622003B1 (ko) | 2013-07-16 | 2016-05-17 | 제일모직주식회사 | 편광판용 접착제 조성물 |
| CA3008952A1 (en) | 2015-12-21 | 2017-06-29 | Sika Technology Ag | Polyaldimine and curable polyurethane composition |
| US11161930B2 (en) | 2015-12-21 | 2021-11-02 | Sika Technology Ag | Two component polyurethane composition |
| US11214706B2 (en) | 2015-12-21 | 2022-01-04 | Sika Technology Ag | Polyurethane composition with low plasticiser migration |
| EP3394134A1 (de) | 2015-12-21 | 2018-10-31 | Sika Technology AG | Hydroxyaldimin und härtbare polyurethanzusammensetzung mit niedrigem gehalt an monomeren isocyanaten |
| CN121046162A (zh) * | 2016-07-27 | 2025-12-02 | 弗门尼舍有限公司 | 制备微胶囊的方法 |
| EP3372652A1 (en) * | 2017-03-07 | 2018-09-12 | Sika Technology Ag | Water-swellable moisture curing one-component polyurethane sealant |
| EP3372651B1 (en) * | 2017-03-07 | 2021-04-07 | Sika Technology Ag | Water-swellable moisture curing one-component polyurethane sealant |
| US11518736B2 (en) * | 2017-06-19 | 2022-12-06 | Sika Technology Ag | Blocking agent for amines, latent hardeners and polyurethane compositions |
| WO2018234267A1 (de) * | 2017-06-19 | 2018-12-27 | Sika Technology Ag | Latenter härter und härtbare polyurethanzusammensetzung |
| US10662329B1 (en) | 2018-06-26 | 2020-05-26 | Jalapeno Holdings, LLC | Bis-Schiff-base thermosetting elastomers |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1064841A (en) | 1963-02-04 | 1967-04-12 | Ici Ltd | Manufacture of polymers containing biuret and urea groups |
| DE2040644C3 (de) | 1970-08-17 | 1978-11-02 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von polyurethankunststoffen |
| US4007239A (en) | 1970-08-17 | 1977-02-08 | Bayer Aktiengesellschaft | Aromatic diamines |
| US3817940A (en) | 1970-08-17 | 1974-06-18 | Bayer Ag | Aromatic diamines |
| US3932360A (en) | 1974-03-14 | 1976-01-13 | Polaroid Corporation | Polyurethane elastomers prepared from diamine curing agents |
| JPS56135514A (en) * | 1979-12-03 | 1981-10-23 | Polaroid Corp | Synthetic polymer and manufacture |
| US4328322A (en) | 1979-12-03 | 1982-05-04 | Polaroid Corporation | Synthetic polymers by polyisocyanate polyaddition process |
| DE3607996A1 (de) | 1986-03-11 | 1987-09-17 | Basf Ag | Feuchtigkeitshaertende, lagerstabile einkomponenten-polyurethansysteme und deren verwendung |
| US5162481A (en) | 1990-03-30 | 1992-11-10 | Minnesota Mining And Manufacturing Company | Polyurethaneurea composition |
| CA2038104C (en) * | 1990-03-30 | 2002-07-23 | Thomas S. Reid | Polyurethaneurea composition |
| JP3207216B2 (ja) * | 1990-07-20 | 2001-09-10 | 三井化学株式会社 | ポリアルジミンを含有する湿気硬化性ポリウレタン組成物、同組成物を含有してなる防水材、床材、シーリング材、壁材、及び塗料 |
| JPH0725976A (ja) * | 1993-07-09 | 1995-01-27 | Mitsui Toatsu Chem Inc | 潜在性硬化剤を含有するイソシアネート組成物の硬化方法 |
| EP1135444B1 (en) * | 1998-11-20 | 2004-08-11 | The Sherwin-Williams Company | Curable compositions comprising acetoacetoxy and imine functionality |
-
1999
- 1999-04-25 IL IL12958399A patent/IL129583A/xx not_active IP Right Cessation
-
2000
- 2000-04-23 MX MXPA01010801A patent/MXPA01010801A/es active IP Right Grant
- 2000-04-23 WO PCT/IL2000/000237 patent/WO2000064860A1/en not_active Ceased
- 2000-04-23 DK DK00919124T patent/DK1173411T3/da active
- 2000-04-23 PT PT00919124T patent/PT1173411E/pt unknown
- 2000-04-23 AU AU39867/00A patent/AU3986700A/en not_active Abandoned
- 2000-04-23 CA CA002371224A patent/CA2371224A1/en not_active Abandoned
- 2000-04-23 AT AT00919124T patent/ATE263749T1/de not_active IP Right Cessation
- 2000-04-23 ES ES00919124T patent/ES2220452T3/es not_active Expired - Lifetime
- 2000-04-23 DE DE60009689T patent/DE60009689T2/de not_active Expired - Fee Related
- 2000-04-23 EP EP00919124A patent/EP1173411B1/en not_active Expired - Lifetime
- 2000-04-23 JP JP2000613813A patent/JP2002543221A/ja not_active Withdrawn
- 2000-04-23 US US09/959,430 patent/US6552155B1/en not_active Expired - Fee Related
-
2007
- 2007-08-03 JP JP2007203684A patent/JP2007284695A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| JP2002543221A (ja) | 2002-12-17 |
| ATE263749T1 (de) | 2004-04-15 |
| AU3986700A (en) | 2000-11-10 |
| MXPA01010801A (es) | 2003-09-04 |
| DE60009689D1 (de) | 2004-05-13 |
| JP2007284695A (ja) | 2007-11-01 |
| EP1173411B1 (en) | 2004-04-07 |
| US6552155B1 (en) | 2003-04-22 |
| DK1173411T3 (da) | 2004-08-02 |
| IL129583A (en) | 2005-05-17 |
| EP1173411A1 (en) | 2002-01-23 |
| WO2000064860A1 (en) | 2000-11-02 |
| CA2371224A1 (en) | 2000-11-02 |
| PT1173411E (pt) | 2004-08-31 |
| ES2220452T3 (es) | 2004-12-16 |
| IL129583A0 (en) | 2000-02-29 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8332 | No legal effect for de | ||
| 8370 | Indication related to discontinuation of the patent is to be deleted | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |