CA2030443A1 - Polyamines par amination de polyoxyalkyleneglycols amorcee par un groupement polyamino - Google Patents

Polyamines par amination de polyoxyalkyleneglycols amorcee par un groupement polyamino

Info

Publication number: CA2030443A1
Authority: CA; Canada
Prior art keywords: amine; type; methyl; polyamine; group
Prior art date: 1990-11-21
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.): Abandoned

Application number

CA 2030443

Other languages

English (en)

Inventor

Michael Cuscurida

John M. Larkin

Kathy B. Sellstrom

Robert A. Grigsby, Jr.

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.)

Huntsman Corp

Original Assignee

Texaco Chemical Co

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.)

1990-11-21

Filing date

1990-11-21

Publication date

1992-05-22

1990-11-21 Application filed by Texaco Chemical Co filed Critical Texaco Chemical Co

1990-11-21 Priority to CA 2030443 priority Critical patent/CA2030443A1/fr

1992-05-22 Publication of CA2030443A1 publication Critical patent/CA2030443A1/fr

Status Abandoned legal-status Critical Current

Links

229920000768 polyamine Polymers 0.000 title claims abstract description 39
150000002334 glycols Chemical class 0.000 title abstract description 5
238000005576 amination reaction Methods 0.000 title description 7
238000000034 method Methods 0.000 claims abstract description 29
229920000647 polyepoxide Polymers 0.000 claims abstract description 27
150000001875 compounds Chemical class 0.000 claims abstract description 26
230000008569 process Effects 0.000 claims abstract description 22
238000010107 reaction injection moulding Methods 0.000 claims abstract description 21
239000003822 epoxy resin Substances 0.000 claims abstract description 18
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims abstract description 14
239000003795 chemical substances by application Substances 0.000 claims abstract description 14
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims abstract description 4
150000001412 amines Chemical class 0.000 claims description 51
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 30
229910052757 nitrogen Inorganic materials 0.000 claims description 27
239000000203 mixture Substances 0.000 claims description 26
239000001257 hydrogen Substances 0.000 claims description 24
229910052739 hydrogen Inorganic materials 0.000 claims description 24
QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 claims description 23
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 20
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 19
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 14
239000005056 polyisocyanate Substances 0.000 claims description 12
229920001228 polyisocyanate Polymers 0.000 claims description 11
229910021529 ammonia Inorganic materials 0.000 claims description 10
239000004970 Chain extender Substances 0.000 claims description 8
WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims description 7
125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
125000005263 alkylenediamine group Chemical group 0.000 claims description 4
150000002118 epoxides Chemical class 0.000 claims description 3
150000002431 hydrogen Chemical group 0.000 claims description 3
125000005702 oxyalkylene group Chemical group 0.000 claims description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
230000006872 improvement Effects 0.000 claims description 2
239000004615 ingredient Substances 0.000 claims description 2
238000006243 chemical reaction Methods 0.000 abstract description 11
239000003999 initiator Substances 0.000 abstract description 11
239000012948 isocyanate Substances 0.000 abstract description 4
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 abstract description 3
150000002513 isocyanates Chemical class 0.000 abstract description 3
238000004519 manufacturing process Methods 0.000 abstract description 3
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 42
239000000047 product Substances 0.000 description 35
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 33
WTFAGPBUAGFMQX-UHFFFAOYSA-N 1-[2-[2-(2-aminopropoxy)propoxy]propoxy]propan-2-amine Chemical compound CC(N)COCC(C)OCC(C)OCC(C)N WTFAGPBUAGFMQX-UHFFFAOYSA-N 0.000 description 29
GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 24
229960005419 nitrogen Drugs 0.000 description 22
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 19
239000000806 elastomer Substances 0.000 description 19
229920001971 elastomer Polymers 0.000 description 18
239000004593 Epoxy Substances 0.000 description 17
239000003054 catalyst Substances 0.000 description 17
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 17
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
-1 aliphatic alcohols Chemical class 0.000 description 14
229920005862 polyol Polymers 0.000 description 13
150000003077 polyols Chemical class 0.000 description 13
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 12
239000000306 component Substances 0.000 description 12
235000011118 potassium hydroxide Nutrition 0.000 description 11
238000002360 preparation method Methods 0.000 description 10
150000003512 tertiary amines Chemical class 0.000 description 10
239000000463 material Substances 0.000 description 8
XTUSEBKMEQERQV-UHFFFAOYSA-N propan-2-ol;hydrate Chemical compound O.CC(C)O XTUSEBKMEQERQV-UHFFFAOYSA-N 0.000 description 8
239000009261 D 400 Substances 0.000 description 7
238000005266 casting Methods 0.000 description 7
230000000704 physical effect Effects 0.000 description 7
229920000570 polyether Polymers 0.000 description 7
229920006389 polyphenyl polymer Polymers 0.000 description 7
PISLZQACAJMAIO-UHFFFAOYSA-N 2,4-diethyl-6-methylbenzene-1,3-diamine Chemical compound CCC1=CC(C)=C(N)C(CC)=C1N PISLZQACAJMAIO-UHFFFAOYSA-N 0.000 description 6
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 6
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 6
125000003118 aryl group Chemical group 0.000 description 6
239000010949 copper Substances 0.000 description 6
230000000875 corresponding effect Effects 0.000 description 6
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 6
239000011734 sodium Substances 0.000 description 6
229910052708 sodium Inorganic materials 0.000 description 6
239000000853 adhesive Substances 0.000 description 5
230000001070 adhesive effect Effects 0.000 description 5
239000011651 chromium Substances 0.000 description 5
230000000052 comparative effect Effects 0.000 description 5
238000009472 formulation Methods 0.000 description 5
150000002989 phenols Chemical class 0.000 description 5
239000011591 potassium Substances 0.000 description 5
229910052700 potassium Inorganic materials 0.000 description 5
229940093932 potassium hydroxide Drugs 0.000 description 5
239000002002 slurry Substances 0.000 description 5
238000003756 stirring Methods 0.000 description 5
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 4
239000007868 Raney catalyst Substances 0.000 description 4
229910000564 Raney nickel Inorganic materials 0.000 description 4
229910052802 copper Inorganic materials 0.000 description 4
230000029087 digestion Effects 0.000 description 4
150000002009 diols Chemical class 0.000 description 4
HCWCAKKEBCNQJP-UHFFFAOYSA-N magnesium orthosilicate Chemical compound [Mg+2].[Mg+2].[O-][Si]([O-])([O-])[O-] HCWCAKKEBCNQJP-UHFFFAOYSA-N 0.000 description 4
239000000391 magnesium silicate Substances 0.000 description 4
229960002366 magnesium silicate Drugs 0.000 description 4
229910052919 magnesium silicate Inorganic materials 0.000 description 4
235000019792 magnesium silicate Nutrition 0.000 description 4
150000003141 primary amines Chemical class 0.000 description 4
GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 4
150000005846 sugar alcohols Polymers 0.000 description 4
QWQNFXDYOCUEER-UHFFFAOYSA-N 2,3-ditert-butyl-4-methylphenol Chemical compound CC1=CC=C(O)C(C(C)(C)C)=C1C(C)(C)C QWQNFXDYOCUEER-UHFFFAOYSA-N 0.000 description 3
VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 3
BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 3
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
229920002396 Polyurea Polymers 0.000 description 3
239000000654 additive Substances 0.000 description 3
125000000217 alkyl group Chemical group 0.000 description 3
229910052804 chromium Inorganic materials 0.000 description 3
150000004985 diamines Chemical class 0.000 description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
239000007788 liquid Substances 0.000 description 3
229910052759 nickel Inorganic materials 0.000 description 3
229920003986 novolac Polymers 0.000 description 3
AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
229920005989 resin Polymers 0.000 description 3
239000011347 resin Substances 0.000 description 3
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 2
FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
239000004721 Polyphenylene oxide Substances 0.000 description 2
QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
125000001931 aliphatic group Chemical group 0.000 description 2
125000002947 alkylene group Chemical group 0.000 description 2
150000001414 amino alcohols Chemical class 0.000 description 2
IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 2
WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
230000003197 catalytic effect Effects 0.000 description 2
238000003776 cleavage reaction Methods 0.000 description 2
229910017052 cobalt Inorganic materials 0.000 description 2
239000010941 cobalt Substances 0.000 description 2
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 2
235000014113 dietary fatty acids Nutrition 0.000 description 2
GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical class C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 2
125000005442 diisocyanate group Chemical group 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
150000002170 ethers Chemical class 0.000 description 2
239000000194 fatty acid Substances 0.000 description 2
229930195729 fatty acid Natural products 0.000 description 2
239000000945 filler Substances 0.000 description 2
125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 2
230000009477 glass transition Effects 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 2
AMWRITDGCCNYAT-UHFFFAOYSA-L hydroxy(oxo)manganese;manganese Chemical compound [Mn].O[Mn]=O.O[Mn]=O AMWRITDGCCNYAT-UHFFFAOYSA-L 0.000 description 2
239000004850 liquid epoxy resins (LERs) Substances 0.000 description 2
239000011777 magnesium Substances 0.000 description 2
229910052749 magnesium Inorganic materials 0.000 description 2
235000001055 magnesium Nutrition 0.000 description 2
229940091250 magnesium supplement Drugs 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
238000002156 mixing Methods 0.000 description 2
229940059574 pentaerithrityl Drugs 0.000 description 2
WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 2
229920000642 polymer Polymers 0.000 description 2
229920001296 polysiloxane Polymers 0.000 description 2
239000004814 polyurethane Substances 0.000 description 2
229920002635 polyurethane Polymers 0.000 description 2
229920003225 polyurethane elastomer Polymers 0.000 description 2
230000009467 reduction Effects 0.000 description 2
229920006395 saturated elastomer Polymers 0.000 description 2
230000007017 scission Effects 0.000 description 2
150000003335 secondary amines Chemical class 0.000 description 2
239000000600 sorbitol Substances 0.000 description 2
235000010356 sorbitol Nutrition 0.000 description 2
239000007858 starting material Substances 0.000 description 2
239000000126 substance Substances 0.000 description 2
239000004094 surface-active agent Substances 0.000 description 2
238000012360 testing method Methods 0.000 description 2
CNHDIAIOKMXOLK-UHFFFAOYSA-N toluquinol Chemical compound CC1=CC(O)=CC=C1O CNHDIAIOKMXOLK-UHFFFAOYSA-N 0.000 description 2
XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 2
PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-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
150000005208 1,4-dihydroxybenzenes Chemical class 0.000 description 1
ALQLPWJFHRMHIU-UHFFFAOYSA-N 1,4-diisocyanatobenzene Chemical compound O=C=NC1=CC=C(N=C=O)C=C1 ALQLPWJFHRMHIU-UHFFFAOYSA-N 0.000 description 1
FJLUATLTXUNBOT-UHFFFAOYSA-N 1-Hexadecylamine Chemical compound CCCCCCCCCCCCCCCCN FJLUATLTXUNBOT-UHFFFAOYSA-N 0.000 description 1
ICLCCFKUSALICQ-UHFFFAOYSA-N 1-isocyanato-4-(4-isocyanato-3-methylphenyl)-2-methylbenzene Chemical compound C1=C(N=C=O)C(C)=CC(C=2C=C(C)C(N=C=O)=CC=2)=C1 ICLCCFKUSALICQ-UHFFFAOYSA-N 0.000 description 1
DTZHXCBUWSTOPO-UHFFFAOYSA-N 1-isocyanato-4-[(4-isocyanato-3-methylphenyl)methyl]-2-methylbenzene Chemical compound C1=C(N=C=O)C(C)=CC(CC=2C=C(C)C(N=C=O)=CC=2)=C1 DTZHXCBUWSTOPO-UHFFFAOYSA-N 0.000 description 1
VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 1
KGRVJHAUYBGFFP-UHFFFAOYSA-N 2,2'-Methylenebis(4-methyl-6-tert-butylphenol) Chemical group CC(C)(C)C1=CC(C)=CC(CC=2C(=C(C=C(C)C=2)C(C)(C)C)O)=C1O KGRVJHAUYBGFFP-UHFFFAOYSA-N 0.000 description 1
MQXNNWDXHFBFEB-UHFFFAOYSA-N 2,2-bis(2-hydroxyphenyl)propane Chemical compound C=1C=CC=C(O)C=1C(C)(C)C1=CC=CC=C1O MQXNNWDXHFBFEB-UHFFFAOYSA-N 0.000 description 1
CVFRFSNPBJUQMG-UHFFFAOYSA-N 2,3-bis(2-hydroxyethyl)benzene-1,4-diol Chemical compound OCCC1=C(O)C=CC(O)=C1CCO CVFRFSNPBJUQMG-UHFFFAOYSA-N 0.000 description 1
TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 1
QZWKEPYTBWZJJA-UHFFFAOYSA-N 3,3'-Dimethoxybenzidine-4,4'-diisocyanate Chemical compound C1=C(N=C=O)C(OC)=CC(C=2C=C(OC)C(N=C=O)=CC=2)=C1 QZWKEPYTBWZJJA-UHFFFAOYSA-N 0.000 description 1
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 1
AGNTUZCMJBTHOG-UHFFFAOYSA-N 3-[3-(2,3-dihydroxypropoxy)-2-hydroxypropoxy]propane-1,2-diol Chemical compound OCC(O)COCC(O)COCC(O)CO AGNTUZCMJBTHOG-UHFFFAOYSA-N 0.000 description 1
ATVJXMYDOSMEPO-UHFFFAOYSA-N 3-prop-2-enoxyprop-1-ene Chemical compound C=CCOCC=C ATVJXMYDOSMEPO-UHFFFAOYSA-N 0.000 description 1
CDBAMNGURPMUTG-UHFFFAOYSA-N 4-[2-(4-hydroxycyclohexyl)propan-2-yl]cyclohexan-1-ol Chemical compound C1CC(O)CCC1C(C)(C)C1CCC(O)CC1 CDBAMNGURPMUTG-UHFFFAOYSA-N 0.000 description 1
ZBJWYPACNNDIOL-UHFFFAOYSA-N 5-isocyanato-1-[(5-isocyanato-5-methylcyclohexa-1,3-dien-1-yl)methyl]-5-methylcyclohexa-1,3-diene Chemical compound C1=CC(C)(N=C=O)CC(CC=2CC(C)(C=CC=2)N=C=O)=C1 ZBJWYPACNNDIOL-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
229930185605 Bisphenol Natural products 0.000 description 1
229920000049 Carbon (fiber) Polymers 0.000 description 1
JJLJMEJHUUYSSY-UHFFFAOYSA-L Copper hydroxide Chemical compound [OH-].[OH-].[Cu+2] JJLJMEJHUUYSSY-UHFFFAOYSA-L 0.000 description 1
239000005750 Copper hydroxide Substances 0.000 description 1
QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 description 1
239000005751 Copper oxide Substances 0.000 description 1
FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
101100536354 Drosophila melanogaster tant gene Proteins 0.000 description 1
239000004386 Erythritol Substances 0.000 description 1
UNXHWFMMPAWVPI-UHFFFAOYSA-N Erythritol Natural products OCC(O)C(O)CO UNXHWFMMPAWVPI-UHFFFAOYSA-N 0.000 description 1
DJOWTWWHMWQATC-KYHIUUMWSA-N Karpoxanthin Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1(O)C(C)(C)CC(O)CC1(C)O)C=CC=C(/C)C=CC2=C(C)CC(O)CC2(C)C DJOWTWWHMWQATC-KYHIUUMWSA-N 0.000 description 1
229930195725 Mannitol Natural products 0.000 description 1
REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical compound CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 description 1
229920000538 Poly[(phenyl isocyanate)-co-formaldehyde] Polymers 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
208000036366 Sensation of pressure Diseases 0.000 description 1
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 1
XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
OORDEDRRTSWSRC-UHFFFAOYSA-N [3-hydroxy-2,2-bis(hydroxymethyl)propyl] acetate Chemical compound CC(=O)OCC(CO)(CO)CO OORDEDRRTSWSRC-UHFFFAOYSA-N 0.000 description 1
BWVAOONFBYYRHY-UHFFFAOYSA-N [4-(hydroxymethyl)phenyl]methanol Chemical compound OCC1=CC=C(CO)C=C1 BWVAOONFBYYRHY-UHFFFAOYSA-N 0.000 description 1
230000001133 acceleration Effects 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
230000000996 additive effect Effects 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
150000003973 alkyl amines Chemical class 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
239000003963 antioxidant agent Substances 0.000 description 1
230000003078 antioxidant effect Effects 0.000 description 1
238000013459 approach Methods 0.000 description 1
150000004984 aromatic diamines Chemical class 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
229910052788 barium Inorganic materials 0.000 description 1
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229910001956 copper hydroxide Inorganic materials 0.000 description 1
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238000000354 decomposition reaction Methods 0.000 description 1
239000007857 degradation product Substances 0.000 description 1
238000006356 dehydrogenation reaction Methods 0.000 description 1
239000000539 dimer Substances 0.000 description 1
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JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical compound CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 description 1
239000000975 dye Substances 0.000 description 1
238000004134 energy conservation Methods 0.000 description 1
125000003700 epoxy group Chemical group 0.000 description 1
UNXHWFMMPAWVPI-ZXZARUISSA-N erythritol Chemical compound OC[C@H](O)[C@H](O)CO UNXHWFMMPAWVPI-ZXZARUISSA-N 0.000 description 1
235000019414 erythritol Nutrition 0.000 description 1
229940009714 erythritol Drugs 0.000 description 1
230000001747 exhibiting effect Effects 0.000 description 1
150000004665 fatty acids Chemical class 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
235000019256 formaldehyde Nutrition 0.000 description 1
229960004279 formaldehyde Drugs 0.000 description 1
239000003365 glass fiber Substances 0.000 description 1
231100001261 hazardous Toxicity 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
235000010299 hexamethylene tetramine Nutrition 0.000 description 1
239000004312 hexamethylene tetramine Substances 0.000 description 1
VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
NWVVVBRKAWDGAB-UHFFFAOYSA-N hydroquinone methyl ether Natural products COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 1
125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 description 1
239000012263 liquid product Substances 0.000 description 1
239000000594 mannitol Substances 0.000 description 1
235000010355 mannitol Nutrition 0.000 description 1
229960001855 mannitol Drugs 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
229910044991 metal oxide Inorganic materials 0.000 description 1
150000004706 metal oxides Chemical class 0.000 description 1
239000003863 metallic catalyst Substances 0.000 description 1
150000002739 metals Chemical class 0.000 description 1
HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 description 1
WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
229960004011 methenamine Drugs 0.000 description 1
KEZAKPHSMMMPQD-UHFFFAOYSA-N methylsulfanyl-(2-methylsulfanylphenyl)methanediamine Chemical compound CSC1=CC=CC=C1C(N)(N)SC KEZAKPHSMMMPQD-UHFFFAOYSA-N 0.000 description 1
230000005012 migration Effects 0.000 description 1
238000013508 migration Methods 0.000 description 1
239000002557 mineral fiber Substances 0.000 description 1
239000006082 mold release agent Substances 0.000 description 1
229910000476 molybdenum oxide Inorganic materials 0.000 description 1
PJUIMOJAAPLTRJ-UHFFFAOYSA-N monothioglycerol Chemical compound OCC(O)CS PJUIMOJAAPLTRJ-UHFFFAOYSA-N 0.000 description 1
238000000465 moulding Methods 0.000 description 1
239000000025 natural resin Substances 0.000 description 1
229910000480 nickel oxide Inorganic materials 0.000 description 1
BFDHFSHZJLFAMC-UHFFFAOYSA-L nickel(ii) hydroxide Chemical compound [OH-].[OH-].[Ni+2] BFDHFSHZJLFAMC-UHFFFAOYSA-L 0.000 description 1
239000011368 organic material Substances 0.000 description 1
PQQKPALAQIIWST-UHFFFAOYSA-N oxomolybdenum Chemical compound [Mo]=O PQQKPALAQIIWST-UHFFFAOYSA-N 0.000 description 1
GNRSAWUEBMWBQH-UHFFFAOYSA-N oxonickel Chemical compound [Ni]=O GNRSAWUEBMWBQH-UHFFFAOYSA-N 0.000 description 1
UWJJYHHHVWZFEP-UHFFFAOYSA-N pentane-1,1-diol Chemical class CCCCC(O)O UWJJYHHHVWZFEP-UHFFFAOYSA-N 0.000 description 1
DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 1
239000000049 pigment Substances 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
239000004848 polyfunctional curative Substances 0.000 description 1
229920001451 polypropylene glycol Polymers 0.000 description 1
238000011417 postcuring Methods 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
150000003142 primary aromatic amines Chemical class 0.000 description 1
238000012545 processing Methods 0.000 description 1
229940095050 propylene Drugs 0.000 description 1
230000000717 retained effect Effects 0.000 description 1
239000003340 retarding agent Substances 0.000 description 1
YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical class OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
150000003333 secondary alcohols Chemical class 0.000 description 1
239000007787 solid Substances 0.000 description 1
229960002920 sorbitol Drugs 0.000 description 1
241000894007 species Species 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
229920003002 synthetic resin Polymers 0.000 description 1
239000000057 synthetic resin Substances 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
AGGKEGLBGGJEBZ-UHFFFAOYSA-N tetramethylenedisulfotetramine Chemical compound C1N(S2(=O)=O)CN3S(=O)(=O)N1CN2C3 AGGKEGLBGGJEBZ-UHFFFAOYSA-N 0.000 description 1
150000003568 thioethers Chemical class 0.000 description 1
ZCUFMDLYAMJYST-UHFFFAOYSA-N thorium dioxide Chemical compound O=[Th]=O ZCUFMDLYAMJYST-UHFFFAOYSA-N 0.000 description 1
229910003452 thorium oxide Inorganic materials 0.000 description 1
RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 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
239000013638 trimer Substances 0.000 description 1
229940113165 trimethylolpropane Drugs 0.000 description 1
229960004418 trolamine Drugs 0.000 description 1
JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1

Landscapes

Polyethers (AREA)

CA 2030443 1990-11-21 1990-11-21 Polyamines par amination de polyoxyalkyleneglycols amorcee par un groupement polyamino Abandoned CA2030443A1 (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA 2030443 CA2030443A1 (fr)	1990-11-21	1990-11-21	Polyamines par amination de polyoxyalkyleneglycols amorcee par un groupement polyamino

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA 2030443 CA2030443A1 (fr)	1990-11-21	1990-11-21	Polyamines par amination de polyoxyalkyleneglycols amorcee par un groupement polyamino

Publications (1)

Publication Number	Publication Date
CA2030443A1 true CA2030443A1 (fr)	1992-05-22

Family

ID=4146487

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA 2030443 Abandoned CA2030443A1 (fr)	1990-11-21	1990-11-21	Polyamines par amination de polyoxyalkyleneglycols amorcee par un groupement polyamino

Country Status (1)

Country	Link
CA (1)	CA2030443A1 (fr)

1990
- 1990-11-21 CA CA 2030443 patent/CA2030443A1/fr not_active Abandoned

Legal Events

Date	Code	Title	Description
1995-05-21	FZDE	Dead

Publication	Publication Date	Title
AU2003262972B2 (en)	2008-11-20	Polyether polyamine agents and mixtures therefor
US4002598A (en)	1977-01-11	Polyether urea epoxy curing agent
US4940770A (en)	1990-07-10	Novel compositions from polyoxyalkylene amines and epoxides
EP2614103B1 (fr)	2015-04-15	Polyétheramines, composition incluant des polyétheramines, et procédés de fabrication
US4178427A (en)	1979-12-11	Polyether urea epoxy curing agent
CN106632994A (zh)	2017-05-10	醚胺及其在聚合物合成中作为中间体的用途
US5422042A (en)	1995-06-06	Imidazolidone polyetheramine strength enhancing additives of epoxy resin systems
US4886867A (en)	1989-12-12	Novel compositions from polyoxyalkylene amines and epoxides
US4992590A (en)	1991-02-12	Polyamines by amination of polyamino initiated polyoxyalkylene glycols
US5128441A (en)	1992-07-07	Block polyamido condensation products
US10731034B2 (en)	2020-08-04	Polyurethane urea composition and preparation method thereof
EP0584967A1 (fr)	1994-03-02	Polyetherpolyols et polyetherdiamines contenant des groupes imidazolidone
EP0301716A2 (fr)	1989-02-01	Polyamidopolyamines
US4825000A (en)	1989-04-25	Phenyl glycidyl ether modified polyoxyalkylene diamines and epoxy resin compositions therefrom
US5391826A (en)	1995-02-21	Amidopolyamines derived from amino-carboxylic acid
US5068444A (en)	1991-11-26	Tetramines by amination of dialdehyde glycol adducts
US4518720A (en)	1985-05-21	Flexible polyurethane foams made from polyether polyols modified with epoxy resin-diamine adducts
US4578412A (en)	1986-03-25	Extended amine curing agents [and epoxy resins cured therewith]
US4990576A (en)	1991-02-05	Tetramines by amination of polyoxyalkylene glycols
US5241016A (en)	1993-08-31	Epoxy adhesives containing aminated, long chain monoepoxide capped polyols
CA2030443A1 (fr)	1992-05-22	Polyamines par amination de polyoxyalkyleneglycols amorcee par un groupement polyamino
US4535133A (en)	1985-08-13	Polyether polyols modified with epoxy resin-diamine adducts
EP0570149B1 (fr)	1997-11-05	Procédé pour la préparation de compositions de résine époxyde
CA1303063C (fr)	1992-06-09	Utilisation de nitrilo(tris)polyoxyalkyleneamines dans un procede de moulage par injection et reaction
US4996294A (en)	1991-02-26	Preparation of aminotetramines