CA1219986A - Melanges durcissables d'urethane et de resine epoxy - Google Patents

Melanges durcissables d'urethane et de resine epoxy

Info

Publication number: CA1219986A
Authority: CA; Canada
Prior art keywords: amine; amino; groups; per molecule; reaction product
Prior art date: 1982-12-15
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.): Expired

Application number

CA000442530A

Other languages

English (en)

Inventor

Christian Burba

Hermann-Josef Lucas

Bernd Neffgen

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Bayer Pharma AG

Original Assignee

Schering AG

Priority date (The priority date 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 date listed.)

1982-12-15

Filing date

1983-12-05

Publication date

1987-03-31

1982-12-15 Priority claimed from US06/450,015 external-priority patent/US4435558A/en

1983-12-05 Application filed by Schering AG filed Critical Schering AG

1987-03-31 Application granted granted Critical

1987-03-31 Publication of CA1219986A publication Critical patent/CA1219986A/fr

Status Expired legal-status Critical Current

Links

239000000203 mixture Substances 0.000 title claims abstract description 33
239000003822 epoxy resin Substances 0.000 title description 19
229920000647 polyepoxide Polymers 0.000 title description 19
150000001412 amines Chemical class 0.000 claims abstract description 43
-1 glycidyl compound Chemical class 0.000 claims abstract description 38
239000004721 Polyphenylene oxide Substances 0.000 claims abstract description 16
238000006243 chemical reaction Methods 0.000 claims abstract description 15
150000001875 compounds Chemical class 0.000 claims abstract description 15
229920000570 polyether Polymers 0.000 claims abstract description 15
230000007062 hydrolysis Effects 0.000 claims abstract description 8
238000006460 hydrolysis reaction Methods 0.000 claims abstract description 8
125000003700 epoxy group Chemical group 0.000 claims abstract description 5
239000000654 additive Substances 0.000 claims abstract description 3
239000000945 filler Substances 0.000 claims abstract description 3
239000000049 pigment Substances 0.000 claims abstract description 3
239000007795 chemical reaction product Substances 0.000 claims description 28
238000000034 method Methods 0.000 claims description 22
239000012948 isocyanate Substances 0.000 claims description 21
150000002513 isocyanates Chemical class 0.000 claims description 21
125000003277 amino group Chemical group 0.000 claims description 18
229920005862 polyol Polymers 0.000 claims description 17
150000003077 polyols Chemical class 0.000 claims description 14
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 11
125000001931 aliphatic group Chemical group 0.000 claims description 9
239000005058 Isophorone diisocyanate Substances 0.000 claims description 8
NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical group CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 claims description 8
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 7
IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 6
125000004432 carbon atom Chemical group C* 0.000 claims description 5
239000007859 condensation product Substances 0.000 claims description 5
239000005056 polyisocyanate Substances 0.000 claims description 5
229920001228 polyisocyanate Polymers 0.000 claims description 5
125000000217 alkyl group Chemical group 0.000 claims description 4
150000004985 diamines Chemical class 0.000 claims description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
239000004215 Carbon black (E152) Substances 0.000 claims description 3
229930195733 hydrocarbon Natural products 0.000 claims description 3
150000002430 hydrocarbons Chemical class 0.000 claims description 3
239000001257 hydrogen Substances 0.000 claims description 3
229910052739 hydrogen Inorganic materials 0.000 claims description 3
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
229910052799 carbon Inorganic materials 0.000 claims description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
239000004848 polyfunctional curative Substances 0.000 claims description 2
229920006295 polythiol Polymers 0.000 claims description 2
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
229920001730 Moisture cure polyurethane Polymers 0.000 claims 1
125000004429 atom Chemical group 0.000 claims 1
150000001732 carboxylic acid derivatives Chemical class 0.000 claims 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
239000005076 polymer ester Substances 0.000 claims 1
229920000136 polysorbate Polymers 0.000 claims 1
229920003002 synthetic resin Polymers 0.000 abstract description 7
239000000057 synthetic resin Substances 0.000 abstract description 7
239000000047 product Substances 0.000 description 23
230000000875 corresponding effect Effects 0.000 description 16
239000003795 chemical substances by application Substances 0.000 description 15
AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 11
IGFHQQFPSIBGKE-UHFFFAOYSA-N 4-nonylphenol Chemical compound CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 10
239000004593 Epoxy Substances 0.000 description 10
238000002360 preparation method Methods 0.000 description 10
LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 7
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 6
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical class C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 6
235000014113 dietary fatty acids Nutrition 0.000 description 6
229930195729 fatty acid Natural products 0.000 description 6
239000000194 fatty acid Substances 0.000 description 6
150000004665 fatty acids Chemical class 0.000 description 6
229920001281 polyalkylene Polymers 0.000 description 6
229920000768 polyamine Polymers 0.000 description 6
RNLHGQLZWXBQNY-UHFFFAOYSA-N 3-(aminomethyl)-3,5,5-trimethylcyclohexan-1-amine Chemical compound CC1(C)CC(N)CC(C)(CN)C1 RNLHGQLZWXBQNY-UHFFFAOYSA-N 0.000 description 5
239000003054 catalyst Substances 0.000 description 5
229920005989 resin Polymers 0.000 description 5
239000011347 resin Substances 0.000 description 5
FKTHNVSLHLHISI-UHFFFAOYSA-N 1,2-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC=C1CN=C=O FKTHNVSLHLHISI-UHFFFAOYSA-N 0.000 description 4
230000002378 acidificating effect Effects 0.000 description 4
150000001298 alcohols Chemical class 0.000 description 4
WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 4
238000007334 copolymerization reaction Methods 0.000 description 4
GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical class C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 4
NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 4
229920001451 polypropylene glycol Polymers 0.000 description 4
230000008569 process Effects 0.000 description 4
238000003756 stirring Methods 0.000 description 4
239000000126 substance Substances 0.000 description 4
IGFHQQFPSIBGKE-RWFIAFQRSA-N 4-nonylphenol Chemical class CCCCCCCCC[13C]1=[13CH][13CH]=[13C](O)[13CH]=[13CH]1 IGFHQQFPSIBGKE-RWFIAFQRSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical group NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 3
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 3
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 3
239000000853 adhesive Substances 0.000 description 3
230000001070 adhesive effect Effects 0.000 description 3
KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 3
150000001735 carboxylic acids Chemical class 0.000 description 3
238000000576 coating method Methods 0.000 description 3
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
150000002148 esters Chemical group 0.000 description 3
125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 3
XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 3
125000002636 imidazolinyl group Chemical group 0.000 description 3
239000004014 plasticizer Substances 0.000 description 3
238000006068 polycondensation reaction Methods 0.000 description 3
230000035939 shock Effects 0.000 description 3
239000002904 solvent Substances 0.000 description 3
125000003396 thiol group Chemical group [H]S* 0.000 description 3
NHXVNEDMKGDNPR-UHFFFAOYSA-N zinc;pentane-2,4-dione Chemical compound [Zn+2].CC(=O)[CH-]C(C)=O.CC(=O)[CH-]C(C)=O NHXVNEDMKGDNPR-UHFFFAOYSA-N 0.000 description 3
YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 2
BUZMJVBOGDBMGI-UHFFFAOYSA-N 1-phenylpropylbenzene Chemical compound C=1C=CC=CC=1C(CC)C1=CC=CC=C1 BUZMJVBOGDBMGI-UHFFFAOYSA-N 0.000 description 2
VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 2
AHDSRXYHVZECER-UHFFFAOYSA-N 2,4,6-tris[(dimethylamino)methyl]phenol Chemical compound CN(C)CC1=CC(CN(C)C)=C(O)C(CN(C)C)=C1 AHDSRXYHVZECER-UHFFFAOYSA-N 0.000 description 2
WJIOHMVWGVGWJW-UHFFFAOYSA-N 3-methyl-n-[4-[(3-methylpyrazole-1-carbonyl)amino]butyl]pyrazole-1-carboxamide Chemical compound N1=C(C)C=CN1C(=O)NCCCCNC(=O)N1N=C(C)C=C1 WJIOHMVWGVGWJW-UHFFFAOYSA-N 0.000 description 2
QHPQWRBYOIRBIT-UHFFFAOYSA-N 4-tert-butylphenol Chemical compound CC(C)(C)C1=CC=C(O)C=C1 QHPQWRBYOIRBIT-UHFFFAOYSA-N 0.000 description 2
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
229910021532 Calcite Inorganic materials 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 2
PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
GKXVJHDEWHKBFH-UHFFFAOYSA-N [2-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=CC=C1CN GKXVJHDEWHKBFH-UHFFFAOYSA-N 0.000 description 2
UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 2
WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
IMUDHTPIFIBORV-UHFFFAOYSA-N aminoethylpiperazine Chemical compound NCCN1CCNCC1 IMUDHTPIFIBORV-UHFFFAOYSA-N 0.000 description 2
150000007860 aryl ester derivatives Chemical class 0.000 description 2
PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-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
239000012975 dibutyltin dilaurate Substances 0.000 description 2
150000001991 dicarboxylic acids Chemical class 0.000 description 2
239000003085 diluting agent Substances 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
150000002009 diols Chemical class 0.000 description 2
238000006266 etherification reaction Methods 0.000 description 2
238000011049 filling Methods 0.000 description 2
IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
230000000873 masking effect Effects 0.000 description 2
SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 2
229940117969 neopentyl glycol Drugs 0.000 description 2
BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 2
239000002245 particle Substances 0.000 description 2
150000002989 phenols Chemical class 0.000 description 2
WLJVNTCWHIRURA-UHFFFAOYSA-N pimelic acid Chemical compound OC(=O)CCCCCC(O)=O WLJVNTCWHIRURA-UHFFFAOYSA-N 0.000 description 2
229920000151 polyglycol Polymers 0.000 description 2
239000010695 polyglycol Substances 0.000 description 2
229920000909 polytetrahydrofuran Polymers 0.000 description 2
229920000166 polytrimethylene carbonate Polymers 0.000 description 2
WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 2
GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
238000007789 sealing Methods 0.000 description 2
CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 description 2
YODZTKMDCQEPHD-UHFFFAOYSA-N thiodiglycol Chemical compound OCCSCCO YODZTKMDCQEPHD-UHFFFAOYSA-N 0.000 description 2
229950006389 thiodiglycol Drugs 0.000 description 2
KJAMZCVTJDTESW-UHFFFAOYSA-N tiracizine Chemical compound C1CC2=CC=CC=C2N(C(=O)CN(C)C)C2=CC(NC(=O)OCC)=CC=C21 KJAMZCVTJDTESW-UHFFFAOYSA-N 0.000 description 2
229960001124 trientine Drugs 0.000 description 2
ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 2
XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 2
JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 2
NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 2
NGZXDRGWBULKFA-NSOVKSMOSA-N (+)-Bebeerine Chemical compound C([C@@H]1N(C)CCC=2C=C(C(=C(OC3=CC=C(C=C3)C[C@H]3C=4C=C(C(=CC=4CCN3C)OC)O3)C=21)O)OC)C1=CC=C(O)C3=C1 NGZXDRGWBULKFA-NSOVKSMOSA-N 0.000 description 1
DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 1
OYHQOLUKZRVURQ-NTGFUMLPSA-N (9Z,12Z)-9,10,12,13-tetratritiooctadeca-9,12-dienoic acid Chemical compound C(CCCCCCC\C(=C(/C\C(=C(/CCCCC)\[3H])\[3H])\[3H])\[3H])(=O)O OYHQOLUKZRVURQ-NTGFUMLPSA-N 0.000 description 1
WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
ZWVMLYRJXORSEP-UHFFFAOYSA-N 1,2,6-Hexanetriol Chemical compound OCCCCC(O)CO ZWVMLYRJXORSEP-UHFFFAOYSA-N 0.000 description 1
229940008841 1,6-hexamethylene diisocyanate Drugs 0.000 description 1
DOJHEVQGYQYOSP-UHFFFAOYSA-N 1-(3-piperazin-1-ylpropyl)piperazine Chemical compound C1CNCCN1CCCN1CCNCC1 DOJHEVQGYQYOSP-UHFFFAOYSA-N 0.000 description 1
AMBFNDRKYCJLNH-UHFFFAOYSA-N 1-(3-piperidin-1-ylpropyl)piperidine Chemical compound C1CCCCN1CCCN1CCCCC1 AMBFNDRKYCJLNH-UHFFFAOYSA-N 0.000 description 1
NTAKERMABXDBQW-UHFFFAOYSA-N 1-[3-(1-aminocyclohexyl)propyl]cyclohexan-1-amine Chemical compound C1CCCCC1(N)CCCC1(N)CCCCC1 NTAKERMABXDBQW-UHFFFAOYSA-N 0.000 description 1
RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 1
RNZADDREKMLIBY-UHFFFAOYSA-N 2-(2-aminoethoxymethoxy)ethanamine Chemical compound NCCOCOCCN RNZADDREKMLIBY-UHFFFAOYSA-N 0.000 description 1
YSUQLAYJZDEMOT-UHFFFAOYSA-N 2-(butoxymethyl)oxirane Chemical compound CCCCOCC1CO1 YSUQLAYJZDEMOT-UHFFFAOYSA-N 0.000 description 1
NCIAZCLIFWUDPR-UHFFFAOYSA-N 2-butyl-3,4,5,6-tetramethylphenol Chemical class CCCCC1=C(C)C(C)=C(C)C(C)=C1O NCIAZCLIFWUDPR-UHFFFAOYSA-N 0.000 description 1
GJYCVCVHRSWLNY-UHFFFAOYSA-N 2-butylphenol Chemical class CCCCC1=CC=CC=C1O GJYCVCVHRSWLNY-UHFFFAOYSA-N 0.000 description 1
ABMULKFGWTYIIK-UHFFFAOYSA-N 2-hexylphenol Chemical class CCCCCCC1=CC=CC=C1O ABMULKFGWTYIIK-UHFFFAOYSA-N 0.000 description 1
JZUHIOJYCPIVLQ-UHFFFAOYSA-N 2-methylpentane-1,5-diamine Chemical compound NCC(C)CCCN JZUHIOJYCPIVLQ-UHFFFAOYSA-N 0.000 description 1
MEEKGULDSDXFCN-UHFFFAOYSA-N 2-pentylphenol Chemical class CCCCCC1=CC=CC=C1O MEEKGULDSDXFCN-UHFFFAOYSA-N 0.000 description 1
LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
RXFCIXRFAJRBSG-UHFFFAOYSA-N 3,2,3-tetramine Chemical compound NCCCNCCNCCCN RXFCIXRFAJRBSG-UHFFFAOYSA-N 0.000 description 1
KRPRVQWGKLEFKN-UHFFFAOYSA-N 3-(3-aminopropoxy)propan-1-amine Chemical compound NCCCOCCCN KRPRVQWGKLEFKN-UHFFFAOYSA-N 0.000 description 1
UIOLCZFGHGKMDD-UHFFFAOYSA-N 3-[12-(3-aminopropoxy)dodecoxy]propan-1-amine Chemical compound NCCCOCCCCCCCCCCCCOCCCN UIOLCZFGHGKMDD-UHFFFAOYSA-N 0.000 description 1
POTQBGGWSWSMCX-UHFFFAOYSA-N 3-[2-(3-aminopropoxy)ethoxy]propan-1-amine Chemical compound NCCCOCCOCCCN POTQBGGWSWSMCX-UHFFFAOYSA-N 0.000 description 1
NMOVZJTXSAJASG-UHFFFAOYSA-N 3-[3-(3-aminopropoxy)butoxy]propan-1-amine Chemical compound NCCCOC(C)CCOCCCN NMOVZJTXSAJASG-UHFFFAOYSA-N 0.000 description 1
PHNLANCZOOOBPJ-UHFFFAOYSA-N 3-[5-(3-aminopropoxy)pentoxy]propan-1-amine Chemical compound NCCCOCCCCCOCCCN PHNLANCZOOOBPJ-UHFFFAOYSA-N 0.000 description 1
NVOQLEBSTHAENC-UHFFFAOYSA-N 3-[6-(3-aminopropoxy)hexoxy]propan-1-amine Chemical compound NCCCOCCCCCCOCCCN NVOQLEBSTHAENC-UHFFFAOYSA-N 0.000 description 1
UVLSCMIEPPWCHZ-UHFFFAOYSA-N 3-piperazin-1-ylpropan-1-amine Chemical compound NCCCN1CCNCC1 UVLSCMIEPPWCHZ-UHFFFAOYSA-N 0.000 description 1
YBRVSVVVWCFQMG-UHFFFAOYSA-N 4,4'-diaminodiphenylmethane Chemical compound C1=CC(N)=CC=C1CC1=CC=C(N)C=C1 YBRVSVVVWCFQMG-UHFFFAOYSA-N 0.000 description 1
LHDWPFTUPAOSNR-UHFFFAOYSA-N 4,5-dihydro-1h-imidazole;hydrazine Chemical compound NN.C1CN=CN1 LHDWPFTUPAOSNR-UHFFFAOYSA-N 0.000 description 1
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BVUDKBBYMKCBAM-UHFFFAOYSA-N 4-[2-[2-(3-aminopropoxy)ethoxy]ethoxy]butan-1-amine Chemical compound NCCCCOCCOCCOCCCN BVUDKBBYMKCBAM-UHFFFAOYSA-N 0.000 description 1
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RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
XPXMKIXDFWLRAA-UHFFFAOYSA-N hydrazinide Chemical compound [NH-]N XPXMKIXDFWLRAA-UHFFFAOYSA-N 0.000 description 1
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
230000006872 improvement Effects 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
150000004658 ketimines Chemical class 0.000 description 1
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239000000463 material Substances 0.000 description 1
239000012764 mineral filler Substances 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
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BEPGHZIEOVULBU-UHFFFAOYSA-N n,n'-diethylpropane-1,3-diamine Chemical compound CCNCCCNCC BEPGHZIEOVULBU-UHFFFAOYSA-N 0.000 description 1
WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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235000021313 oleic acid Nutrition 0.000 description 1
239000012766 organic filler Substances 0.000 description 1
RPQRDASANLAFCM-UHFFFAOYSA-N oxiran-2-ylmethyl prop-2-enoate Chemical compound C=CC(=O)OCC1CO1 RPQRDASANLAFCM-UHFFFAOYSA-N 0.000 description 1
125000004430 oxygen atom Chemical group O* 0.000 description 1
229920001568 phenolic resin Polymers 0.000 description 1
BSCCSDNZEIHXOK-UHFFFAOYSA-N phenyl carbamate Chemical class NC(=O)OC1=CC=CC=C1 BSCCSDNZEIHXOK-UHFFFAOYSA-N 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical class OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 1
229920006324 polyoxymethylene Polymers 0.000 description 1
239000004814 polyurethane Substances 0.000 description 1
229920002635 polyurethane Polymers 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
230000001698 pyrogenic effect Effects 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
235000012239 silicon dioxide Nutrition 0.000 description 1
239000000243 solution Substances 0.000 description 1
239000000758 substrate Substances 0.000 description 1
150000005846 sugar alcohols Polymers 0.000 description 1
239000003784 tall oil Substances 0.000 description 1
ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 1
TUNFSRHWOTWDNC-HKGQFRNVSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCC[14C](O)=O TUNFSRHWOTWDNC-HKGQFRNVSA-N 0.000 description 1
FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
229920001187 thermosetting polymer Polymers 0.000 description 1
239000004634 thermosetting polymer Substances 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
230000007704 transition Effects 0.000 description 1
LWBHHRRTOZQPDM-UHFFFAOYSA-N undecanedioic acid Chemical compound OC(=O)CCCCCCCCCC(O)=O LWBHHRRTOZQPDM-UHFFFAOYSA-N 0.000 description 1
235000021122 unsaturated fatty acids Nutrition 0.000 description 1
150000004670 unsaturated fatty acids Chemical class 0.000 description 1
229940005605 valeric acid Drugs 0.000 description 1
235000013311 vegetables Nutrition 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1

Landscapes

Polyurethanes Or Polyureas (AREA)

CA000442530A 1982-12-15 1983-12-05 Melanges durcissables d'urethane et de resine epoxy Expired CA1219986A (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US450,015		1982-12-15
US06/450,015 US4435558A (en)	1981-12-28	1982-12-15	Hardenable urethane-epoxy resin mixtures

Publications (1)

Publication Number	Publication Date
CA1219986A true CA1219986A (fr)	1987-03-31

Family

ID=23786410

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000442530A Expired CA1219986A (fr)	1982-12-15	1983-12-05	Melanges durcissables d'urethane et de resine epoxy

Country Status (1)

Country	Link
CA (1)	CA1219986A (fr)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5219975A (en) *	1990-05-12	1993-06-15	Bayer Aktiengesellschaft	Process for the preparation of amines, the amines thus obtained and the use thereof as hardeners for epoxide resins
WO2004046217A1 (fr) *	2002-11-15	2004-06-03	Bayer Materialscience Ag	Systeme reactif durcissant a temperature ambiante
US6977279B1 (en)	1999-07-28	2005-12-20	Bayer Aktiengesellschaft	Solvent-free room temperature curing reactive systems and the use thereof in the production of adhesives, sealing agents, casting compounds, molded articles or coatings
US7001972B1 (en)	1999-07-28	2006-02-21	Bayer Aktiengesellschaft	Polyamines comprising urea groups, method for their production, and their use as hardeners for epoxide resins
US20230127025A1 (en) *	2020-04-08	2023-04-27	Covestro Deutschland Ag	Low-viscous isocyanate prepolymers blocked with phenols obtainable from cashew nutshell oil, method for the production thereof and use thereof

1983
- 1983-12-05 CA CA000442530A patent/CA1219986A/fr not_active Expired

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5219975A (en) *	1990-05-12	1993-06-15	Bayer Aktiengesellschaft	Process for the preparation of amines, the amines thus obtained and the use thereof as hardeners for epoxide resins
US6977279B1 (en)	1999-07-28	2005-12-20	Bayer Aktiengesellschaft	Solvent-free room temperature curing reactive systems and the use thereof in the production of adhesives, sealing agents, casting compounds, molded articles or coatings
US7001972B1 (en)	1999-07-28	2006-02-21	Bayer Aktiengesellschaft	Polyamines comprising urea groups, method for their production, and their use as hardeners for epoxide resins
WO2004046217A1 (fr) *	2002-11-15	2004-06-03	Bayer Materialscience Ag	Systeme reactif durcissant a temperature ambiante
US6977289B2 (en)	2002-11-15	2005-12-20	Bayer Aktiengesellschaft	Reactive systems that harden at room temperature
US20230127025A1 (en) *	2020-04-08	2023-04-27	Covestro Deutschland Ag	Low-viscous isocyanate prepolymers blocked with phenols obtainable from cashew nutshell oil, method for the production thereof and use thereof

Legal Events

Date	Code	Title	Description
2004-03-31	MKEX	Expiry

Publication	Publication Date	Title
US4847319A (en)	1989-07-11	Sealant compositions or coating mixtures containing functional silane or siloxane adhesion promotors nonreactive with blocked isocyanates
US4435558A (en)	1984-03-06	Hardenable urethane-epoxy resin mixtures
US3993708A (en)	1976-11-23	Elastic hardened epoxy resin polymers
KR102351716B1 (ko)	2022-01-13	콘크리트용 무용제 이액형 프라이머 조성물
EP0950675B1 (fr)	2004-10-13	Systèmes réactifs et leur utilisation pour la production de revêtements, adhésifs, matériaux d'étanchéité, matériaux de coulée ou des pièces moulées
EP0350890B1 (fr)	1993-12-01	Polyuréthanes préparés à partir de mélanges de polyoxypropylène-polyols et de polyols intermédiaires basés sur des copolymères à blocs d'organo-silicone
JP2023521346A (ja)	2023-05-24	カシューナッツ殻油から得られるフェノールでブロックされた低粘度イソシアネートプレポリマー、その製造方法及びその使用
EP0457089B1 (fr)	1994-03-09	Procédé de préparation d'amines et leur utilisation comme durcisseur pour des résines époxydes
JP2677346B2 (ja)	1997-11-17	硬化性ポリエポキシド樹脂組成物
US5510432A (en)	1996-04-23	Mixed blocked isocyanate prepolymers, a process for their production and their use for the production of flexible epoxy resin systems
US4632970A (en)	1986-12-30	Epoxy resin composition
US4870150A (en)	1989-09-26	Polyurethanes made from blends of polypropyleneoxide polyol and polybutyleneoxide polyol intermediates
EP1208128B1 (fr)	2003-10-01	Polyamines comportant des groupes uree, procede permettant de les preparer et leur utilisation comme durcisseurs de resines epoxydes
EP1204691B1 (fr)	2003-10-01	Systemes reactifs exempts de solvants et durcissant a temperature ambiante et leur utilisation pour la production d'adhesifs, de masses d'etancheite, de masses de remplissage, de pieces moulees ou de revetements
US5187253A (en)	1993-02-16	Method of manufacturing polyetherurethane urea amines, and use of same
EP0082983B1 (fr)	1987-02-04	Compositions de résine synthétique durcissables et agents pour compositions de résine synthétique durcissables à base d'amines de polyéther-uréthanne-urée et de résines époxide et/ou d'esters aryliques/aromatiques de l'acide carbamique
US5153296A (en)	1992-10-06	Epoxide resin mixtures which harden at room temperature
WO2004046217A1 (fr)	2004-06-03	Systeme reactif durcissant a temperature ambiante
WO2004003050A1 (fr)	2004-01-08	Amines de polyether-urethane
DE19755031B4 (de)	2004-07-29	Bei Raumtemperatur härtbare Epoxidharzmischungen und ihre Verwendung
KR920009737B1 (ko)	1992-10-22	에폭시 수지 조성물