CA1082381A - Chalk-resistant, medium to dark colored polyurethanes, polymer/polyol and polyisocyanate compositions for use in producing same and methods for making said polyurethanes - Google Patents

Chalk-resistant, medium to dark colored polyurethanes, polymer/polyol and polyisocyanate compositions for use in producing same and methods for making said polyurethanes

Info

Publication number: CA1082381A
Authority: CA; Canada
Prior art keywords: polymer; polyol; composition; ferrocene; polyurethane
Prior art date: 1976-11-22
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

CA282,630A

Other languages

English (en)

French (fr)

Inventor

William A. Gill

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.)

Union Carbide Corp

Original Assignee

Union Carbide Corp

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.)

1976-11-22

Filing date

1977-07-13

Publication date

1980-07-22

1977-06-20 Priority claimed from US05/807,590 external-priority patent/US4143002A/en

1977-07-13 Application filed by Union Carbide Corp filed Critical Union Carbide Corp

1980-07-22 Application granted granted Critical

1980-07-22 Publication of CA1082381A publication Critical patent/CA1082381A/en

Status Expired legal-status Critical Current

Links

229920000642 polymer Polymers 0.000 title claims abstract description 188
229920005862 polyol Polymers 0.000 title claims abstract description 174
150000003077 polyols Chemical class 0.000 title claims abstract description 173
239000000203 mixture Substances 0.000 title claims abstract description 89
239000004814 polyurethane Substances 0.000 title claims abstract description 78
229920002635 polyurethane Polymers 0.000 title claims abstract description 67
239000005056 polyisocyanate Substances 0.000 title claims abstract description 28
229920001228 polyisocyanate Polymers 0.000 title claims abstract description 25
238000000034 method Methods 0.000 title claims description 31
KTWOOEGAPBSYNW-UHFFFAOYSA-N ferrocene Chemical compound [Fe+2].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 KTWOOEGAPBSYNW-UHFFFAOYSA-N 0.000 claims abstract description 71
239000000178 monomer Substances 0.000 claims abstract description 39
239000003054 catalyst Substances 0.000 claims abstract description 28
238000006243 chemical reaction Methods 0.000 claims abstract description 24
239000000049 pigment Substances 0.000 claims abstract description 18
ILZSSCVGGYJLOG-UHFFFAOYSA-N cobaltocene Chemical compound [Co+2].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 ILZSSCVGGYJLOG-UHFFFAOYSA-N 0.000 claims abstract description 13
KZPXREABEBSAQM-UHFFFAOYSA-N cyclopenta-1,3-diene;nickel(2+) Chemical compound [Ni+2].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 KZPXREABEBSAQM-UHFFFAOYSA-N 0.000 claims abstract description 10
230000006872 improvement Effects 0.000 claims abstract description 6
239000000806 elastomer Substances 0.000 claims description 36
229920001971 elastomer Polymers 0.000 claims description 32
239000006229 carbon black Substances 0.000 claims description 21
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 19
239000006260 foam Substances 0.000 claims description 16
125000002947 alkylene group Chemical group 0.000 claims description 14
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 12
238000004519 manufacturing process Methods 0.000 claims description 8
239000004604 Blowing Agent Substances 0.000 claims description 7
125000003118 aryl group Chemical group 0.000 claims description 6
229920003225 polyurethane elastomer Polymers 0.000 claims description 6
NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 5
FAGBBSPMGNEZEQ-UHFFFAOYSA-N cyclopenta-1,3-diene 5-(2-cyclopenta-2,4-dien-1-ylpropan-2-yl)cyclopenta-1,3-diene iron(2+) Chemical group [Fe++].[Fe++].c1cc[cH-]c1.c1cc[cH-]c1.CC(C)([c-]1cccc1)[c-]1cccc1 FAGBBSPMGNEZEQ-UHFFFAOYSA-N 0.000 claims description 5
239000004970 Chain extender Substances 0.000 claims description 4
238000005187 foaming Methods 0.000 claims description 3
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 3
238000011065 in-situ storage Methods 0.000 claims description 3
239000001054 red pigment Substances 0.000 claims description 2
239000003381 stabilizer Substances 0.000 claims description 2
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical group ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 3
241000872198 Serjania polyphylla Species 0.000 claims 1
125000001931 aliphatic group Chemical group 0.000 claims 1
-1 benzoyl ferrocene Chemical compound 0.000 description 31
239000000047 product Substances 0.000 description 30
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 12
125000002887 hydroxy group Chemical group [H]O* 0.000 description 12
230000000694 effects Effects 0.000 description 10
229910052751 metal Inorganic materials 0.000 description 10
239000002184 metal Substances 0.000 description 10
238000012360 testing method Methods 0.000 description 10
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
238000002156 mixing Methods 0.000 description 9
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 8
229920001577 copolymer Polymers 0.000 description 8
239000002245 particle Substances 0.000 description 8
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 7
239000000463 material Substances 0.000 description 7
230000000704 physical effect Effects 0.000 description 7
230000008569 process Effects 0.000 description 7
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 6
239000004606 Fillers/Extenders Substances 0.000 description 6
GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 6
239000007795 chemical reaction product Substances 0.000 description 6
239000012948 isocyanate Substances 0.000 description 6
229920002554 vinyl polymer Polymers 0.000 description 6
150000001875 compounds Chemical class 0.000 description 5
150000002513 isocyanates Chemical class 0.000 description 5
150000002739 metals Chemical class 0.000 description 5
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 4
229920006311 Urethane elastomer Polymers 0.000 description 4
UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 4
229920001400 block copolymer Polymers 0.000 description 4
239000003795 chemical substances by application Substances 0.000 description 4
238000000576 coating method Methods 0.000 description 4
239000012975 dibutyltin dilaurate Substances 0.000 description 4
229910052748 manganese Inorganic materials 0.000 description 4
239000011572 manganese Substances 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
229910052718 tin Inorganic materials 0.000 description 4
PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
101100010166 Mus musculus Dok3 gene Proteins 0.000 description 3
SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
229910052782 aluminium Inorganic materials 0.000 description 3
229910017052 cobalt Inorganic materials 0.000 description 3
239000010941 cobalt Substances 0.000 description 3
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 3
239000006185 dispersion Substances 0.000 description 3
238000009472 formulation Methods 0.000 description 3
235000011187 glycerol Nutrition 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 3
150000002500 ions Chemical class 0.000 description 3
239000007788 liquid Substances 0.000 description 3
229910052757 nitrogen Inorganic materials 0.000 description 3
125000002524 organometallic group Chemical group 0.000 description 3
239000003973 paint Substances 0.000 description 3
229920001610 polycaprolactone Polymers 0.000 description 3
239000004632 polycaprolactone Substances 0.000 description 3
238000006116 polymerization reaction Methods 0.000 description 3
238000002360 preparation method Methods 0.000 description 3
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 3
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 3
150000003839 salts Chemical class 0.000 description 3
239000002904 solvent Substances 0.000 description 3
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
WCVOGSZTONGSQY-UHFFFAOYSA-N 2,4,6-trichloroanisole Chemical compound COC1=C(Cl)C=C(Cl)C=C1Cl WCVOGSZTONGSQY-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
239000004215 Carbon black (E152) Substances 0.000 description 2
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
239000005977 Ethylene Substances 0.000 description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 2
CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 2
BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 2
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
239000004743 Polypropylene Substances 0.000 description 2
229920005830 Polyurethane Foam Polymers 0.000 description 2
UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 2
YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 2
239000002253 acid Substances 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
239000000654 additive Substances 0.000 description 2
229910052784 alkaline earth metal Inorganic materials 0.000 description 2
150000001342 alkaline earth metals Chemical class 0.000 description 2
XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 2
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
229910052787 antimony Inorganic materials 0.000 description 2
150000004982 aromatic amines Chemical class 0.000 description 2
229910052785 arsenic Inorganic materials 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
229910052797 bismuth Inorganic materials 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
238000009833 condensation Methods 0.000 description 2
230000005494 condensation Effects 0.000 description 2
QXYJCZRRLLQGCR-UHFFFAOYSA-N dioxomolybdenum Chemical compound O=[Mo]=O QXYJCZRRLLQGCR-UHFFFAOYSA-N 0.000 description 2
239000007789 gas Substances 0.000 description 2
229920001519 homopolymer Polymers 0.000 description 2
229930195733 hydrocarbon Natural products 0.000 description 2
239000001257 hydrogen Substances 0.000 description 2
229910052739 hydrogen Inorganic materials 0.000 description 2
239000004615 ingredient Substances 0.000 description 2
IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 2
229910052745 lead Inorganic materials 0.000 description 2
239000004611 light stabiliser Substances 0.000 description 2
229920002521 macromolecule Polymers 0.000 description 2
229910052760 oxygen Inorganic materials 0.000 description 2
229910052698 phosphorus Inorganic materials 0.000 description 2
239000011574 phosphorus Substances 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
229920003023 plastic Polymers 0.000 description 2
239000004033 plastic Substances 0.000 description 2
230000000379 polymerizing effect Effects 0.000 description 2
229920001451 polypropylene glycol Polymers 0.000 description 2
239000011496 polyurethane foam Substances 0.000 description 2
230000002265 prevention Effects 0.000 description 2
YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 2
150000003254 radicals Chemical class 0.000 description 2
SMQUZDBALVYZAC-UHFFFAOYSA-N salicylaldehyde Chemical compound OC1=CC=CC=C1C=O SMQUZDBALVYZAC-UHFFFAOYSA-N 0.000 description 2
DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 2
TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 description 1
FVQMJJQUGGVLEP-UHFFFAOYSA-N (2-methylpropan-2-yl)oxy 2-ethylhexaneperoxoate Chemical compound CCCCC(CC)C(=O)OOOC(C)(C)C FVQMJJQUGGVLEP-UHFFFAOYSA-N 0.000 description 1
KAKVFSYQVNHFBS-UHFFFAOYSA-N (5-hydroxycyclopenten-1-yl)-phenylmethanone Chemical compound OC1CCC=C1C(=O)C1=CC=CC=C1 KAKVFSYQVNHFBS-UHFFFAOYSA-N 0.000 description 1
ZBBLRPRYYSJUCZ-GRHBHMESSA-L (z)-but-2-enedioate;dibutyltin(2+) Chemical compound [O-]C(=O)\C=C/C([O-])=O.CCCC[Sn+2]CCCC ZBBLRPRYYSJUCZ-GRHBHMESSA-L 0.000 description 1
DGLFZUBOMRZNQX-UHFFFAOYSA-N 1,1,2,2,3,3-hexafluorocyclobutane Chemical compound FC1(F)CC(F)(F)C1(F)F DGLFZUBOMRZNQX-UHFFFAOYSA-N 0.000 description 1
FRCHKSNAZZFGCA-UHFFFAOYSA-N 1,1-dichloro-1-fluoroethane Chemical compound CC(F)(Cl)Cl FRCHKSNAZZFGCA-UHFFFAOYSA-N 0.000 description 1
IYJMQRLCWBFHJL-UHFFFAOYSA-N 1,11-diisocyanatoundecane Chemical compound O=C=NCCCCCCCCCCCN=C=O IYJMQRLCWBFHJL-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
ZGDSDWSIFQBAJS-UHFFFAOYSA-N 1,2-diisocyanatopropane Chemical compound O=C=NC(C)CN=C=O ZGDSDWSIFQBAJS-UHFFFAOYSA-N 0.000 description 1
IKYNWXNXXHWHLL-UHFFFAOYSA-N 1,3-diisocyanatopropane Chemical compound O=C=NCCCN=C=O IKYNWXNXXHWHLL-UHFFFAOYSA-N 0.000 description 1
MCICIPKNWSPYOA-UHFFFAOYSA-N 1,4-diisocyanato-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC(N=C=O)=CC=C1N=C=O MCICIPKNWSPYOA-UHFFFAOYSA-N 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
OVBFMUAFNIIQAL-UHFFFAOYSA-N 1,4-diisocyanatobutane Chemical compound O=C=NCCCCN=C=O OVBFMUAFNIIQAL-UHFFFAOYSA-N 0.000 description 1
KCMMASHQZUIAOW-UHFFFAOYSA-N 1,5-diisocyanato-2,2,4-trimethylpentane Chemical compound O=C=NCC(C)CC(C)(C)CN=C=O KCMMASHQZUIAOW-UHFFFAOYSA-N 0.000 description 1
QUPKOUOXSNGVLB-UHFFFAOYSA-N 1,8-diisocyanatooctane Chemical compound O=C=NCCCCCCCCN=C=O QUPKOUOXSNGVLB-UHFFFAOYSA-N 0.000 description 1
GHSZVIPKVOEXNX-UHFFFAOYSA-N 1,9-diisocyanatononane Chemical compound O=C=NCCCCCCCCCN=C=O GHSZVIPKVOEXNX-UHFFFAOYSA-N 0.000 description 1
SZBXTBGNJLZMHB-UHFFFAOYSA-N 1-chloro-2,4-diisocyanatobenzene Chemical compound ClC1=CC=C(N=C=O)C=C1N=C=O SZBXTBGNJLZMHB-UHFFFAOYSA-N 0.000 description 1
JRVZITODZAQRQM-UHFFFAOYSA-N 1-isocyanato-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1N=C=O JRVZITODZAQRQM-UHFFFAOYSA-N 0.000 description 1
CVBUKMMMRLOKQR-UHFFFAOYSA-N 1-phenylbutane-1,3-dione Chemical compound CC(=O)CC(=O)C1=CC=CC=C1 CVBUKMMMRLOKQR-UHFFFAOYSA-N 0.000 description 1
OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 1
OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 description 1
GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 description 1
AKCRQHGQIJBRMN-UHFFFAOYSA-N 2-chloroaniline Chemical compound NC1=CC=CC=C1Cl AKCRQHGQIJBRMN-UHFFFAOYSA-N 0.000 description 1
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 1
LYKQCVSVGJKFGJ-UHFFFAOYSA-N 3,5-diisocyanato-3,5-dimethylcyclohexene Chemical group O=C=NC1(C)CC=CC(C)(N=C=O)C1 LYKQCVSVGJKFGJ-UHFFFAOYSA-N 0.000 description 1
AIMDYNJRXHEXEL-UHFFFAOYSA-N 3-phenylprop-1-enylbenzene Chemical compound C=1C=CC=CC=1CC=CC1=CC=CC=C1 AIMDYNJRXHEXEL-UHFFFAOYSA-N 0.000 description 1
JLBJTVDPSNHSKJ-UHFFFAOYSA-N 4-Methylstyrene Chemical compound CC1=CC=C(C=C)C=C1 JLBJTVDPSNHSKJ-UHFFFAOYSA-N 0.000 description 1
HVCNXQOWACZAFN-UHFFFAOYSA-N 4-ethylmorpholine Chemical compound CCN1CCOCC1 HVCNXQOWACZAFN-UHFFFAOYSA-N 0.000 description 1
XRUDAAKPTLVBMB-UHFFFAOYSA-N 6-(methylazaniumyl)hexanoate Chemical compound CNCCCCCC(O)=O XRUDAAKPTLVBMB-UHFFFAOYSA-N 0.000 description 1
NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
NUQHZWXJISCJGY-UHFFFAOYSA-N C1(=CC=CC1)[Ni]C1=CC=CC1.[CH-]1C=CC=C1.[CH-]1C=CC=C1.[Ni+2] Chemical compound C1(=CC=CC1)[Ni]C1=CC=CC1.[CH-]1C=CC=C1.[CH-]1C=CC=C1.[Ni+2] NUQHZWXJISCJGY-UHFFFAOYSA-N 0.000 description 1
NHFBQCFQJAPUOK-UHFFFAOYSA-N C1(C=CC=C1)[Co]C1C=CC=C1.[CH-]1C=CC=C1.[CH-]1C=CC=C1.[Co+2] Chemical compound C1(C=CC=C1)[Co]C1C=CC=C1.[CH-]1C=CC=C1.[CH-]1C=CC=C1.[Co+2] NHFBQCFQJAPUOK-UHFFFAOYSA-N 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
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 1
HEBKCHPVOIAQTA-QWWZWVQMSA-N D-arabinitol Chemical compound OC[C@@H](O)C(O)[C@H](O)CO HEBKCHPVOIAQTA-QWWZWVQMSA-N 0.000 description 1
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NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 description 1
229910052726 zirconium Inorganic materials 0.000 description 1
PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- 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
- C08G18/63—Block or graft polymers obtained by polymerising compounds having carbon-to-carbon double bonds on to polymers
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/56—Organo-metallic compounds, i.e. organic compounds containing a metal-to-carbon bond
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L57/00—Compositions of unspecified polymers obtained by reactions only involving carbon-to-carbon unsaturated bonds
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L75/00—Compositions of polyureas or polyurethanes; Compositions of derivatives of such polymers
- C08L75/04—Polyurethanes

Landscapes

Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Medicinal Chemistry (AREA)
Polymers & Plastics (AREA)
Organic Chemistry (AREA)
Polyurethanes Or Polyureas (AREA)
Compositions Of Macromolecular Compounds (AREA)

CA282,630A 1976-11-22 1977-07-13 Chalk-resistant, medium to dark colored polyurethanes, polymer/polyol and polyisocyanate compositions for use in producing same and methods for making said polyurethanes Expired CA1082381A (en)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
US74361476A	1976-11-22	1976-11-22
US743,614		1976-11-22
US05/807,590 US4143002A (en)	1976-11-22	1977-06-20	Chalk-resistant, medium to dark colored polyurethanes, polymer/polyol and polyisocyanate compositions for use in producing same and methods for making said polyurethanes
US807,590		1977-06-20

Publications (1)

Publication Number	Publication Date
CA1082381A true CA1082381A (en)	1980-07-22

Family

ID=27114179

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA282,630A Expired CA1082381A (en)	1976-11-22	1977-07-13	Chalk-resistant, medium to dark colored polyurethanes, polymer/polyol and polyisocyanate compositions for use in producing same and methods for making said polyurethanes

Country Status (14)

Country	Link
JP (1)	JPS5850619B2 (it)
AU (1)	AU509221B2 (it)
BR (1)	BR7704813A (it)
CA (1)	CA1082381A (it)
DE (1)	DE2733243C3 (it)
ES (1)	ES460953A1 (it)
FR (1)	FR2371487A1 (it)
GB (1)	GB1563029A (it)
HK (1)	HK27881A (it)
IT (1)	IT1081601B (it)
MX (1)	MX147293A (it)
MY (1)	MY8200040A (it)
NL (1)	NL7708172A (it)
SE (2)	SE437844B (it)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS5938247B2 (ja) *	1976-12-08	1984-09-14	三菱化学株式会社	難燃性フオ−ムの製造法
US4448903A (en) *	1983-07-25	1984-05-15	Mobay Chemical Corporation	Novel system for the production of polyurethanes
US5364906A (en) *	1993-08-20	1994-11-15	Arco Chemical Technology, L.P.	Low viscosity polymer polyols with improved dispersion stability

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
BE795480A (fr) *	1972-02-17	1973-08-16	Syntex Corp	Additifs de polymeres pour la suppression des fumees

1977
- 1977-07-13 CA CA282,630A patent/CA1082381A/en not_active Expired
- 1977-07-20 AU AU27189/77A patent/AU509221B2/en not_active Expired
- 1977-07-22 GB GB30973/77A patent/GB1563029A/en not_active Expired
- 1977-07-22 JP JP52087473A patent/JPS5850619B2/ja not_active Expired
- 1977-07-22 MX MX169948A patent/MX147293A/es unknown
- 1977-07-22 NL NL7708172A patent/NL7708172A/xx not_active Application Discontinuation
- 1977-07-22 ES ES460953A patent/ES460953A1/es not_active Expired
- 1977-07-22 FR FR7722558A patent/FR2371487A1/fr active Granted
- 1977-07-22 SE SE7708474A patent/SE437844B/xx unknown
- 1977-07-22 IT IT26048/77A patent/IT1081601B/it active
- 1977-07-22 BR BR7704813A patent/BR7704813A/pt unknown
- 1977-07-22 DE DE2733243A patent/DE2733243C3/de not_active Expired
1981
- 1981-06-25 HK HK278/81A patent/HK27881A/xx unknown
1982
- 1982-12-30 MY MY40/82A patent/MY8200040A/xx unknown
1983
- 1983-04-28 SE SE8302410A patent/SE8302410L/sv not_active Application Discontinuation

Also Published As

Publication number	Publication date
DE2733243A1 (de)	1978-05-24
DE2733243C3 (de)	1982-03-18
MY8200040A (en)	1982-12-31
SE7708474L (sv)	1978-05-23
FR2371487B1 (it)	1984-06-15
GB1563029A (en)	1980-03-19
JPS5850619B2 (ja)	1983-11-11
MX147293A (es)	1982-11-10
FR2371487A1 (fr)	1978-06-16
SE437844B (sv)	1985-03-18
SE8302410D0 (sv)	1983-04-28
DE2733243B2 (de)	1981-07-16
BR7704813A (pt)	1978-08-15
IT1081601B (it)	1985-05-21
ES460953A1 (es)	1978-05-16
AU2718977A (en)	1979-01-25
NL7708172A (nl)	1978-05-24
SE8302410L (sv)	1983-04-28
JPS5364264A (en)	1978-06-08
HK27881A (en)	1981-07-03
AU509221B2 (en)	1980-05-01

Publication	Publication Date	Title
EP0095653B1 (en)	1991-10-09	Polymer/polyol compositions having improved combustion resistance and a process for preparing polyurethanes
US4381352A (en)	1983-04-26	Process for reinforced reaction injection molding of polyurethanes
US5011908A (en)	1991-04-30	Polymer polyol compositions and their use in the preparation of polyurethane foams
CA1105182A (en)	1981-07-14	High ethylene oxide content polyols and polymer/polyols and polyurethanes made therefrom
DE60209596T2 (de)	2006-08-10	Polyurethanschaum-Zusammensetzung verwendbar in Schuhsohlen und Verfahren zu ihrer Herstellung
US4332716A (en)	1982-06-01	Polymer/polyisocyanate compositions, processes for making same and processes for making polyurethane products therefrom
US5171759A (en)	1992-12-15	Polymer polyol compositions and their use in the preparation of polyurethane foams
DE2912330A1 (de)	1979-10-04	Polymer/polyol-praeparate, verfahren zu deren herstellung und verfahren zur herstellung von polyurethanen aus denselben
US4994502A (en)	1991-02-19	Process for the preparation of integral skin polyurethane steering wheels
DE2334259A1 (de)	1974-01-31	Polyurethanschaum mit einer feuerhemmenden vollstaendigen haut
US4963399A (en)	1990-10-16	Polyurethane foam with low vinyl-staining tendencies
CA1314115C (en)	1993-03-02	Flexible flame resistant polyurethane foams
US5132329A (en)	1992-07-21	Integral skin polyurethane foam
US4458050A (en)	1984-07-03	Polymer dispersions and their uses
US4539339A (en)	1985-09-03	Polyurethane foams made from vinyl polymer polyols
CA1082381A (en)	1980-07-22	Chalk-resistant, medium to dark colored polyurethanes, polymer/polyol and polyisocyanate compositions for use in producing same and methods for making said polyurethanes
US4622361A (en)	1986-11-11	Flame retarded high modulus polyurethane elastomers and method of making same
EP0451559A2 (en)	1991-10-16	Integral skin polyurethane foam
JP2550091B2 (ja)	1996-10-30	重合体／ポリイソシアネート分散体
CA1188049A (en)	1985-05-28	Graft polyol rim system possessing excellent thermal properties
GB2270320A (en)	1994-03-09	Blown integral skin polyurethane foam
CA1269492A (en)	1990-05-22	Rim microcellular polyurethane elastomer employing heteric or internal block ethylene oxide polyols
EP0350868B1 (en)	1994-11-30	Polymer polyol composition and their use in the preparation of polyurethane foams
US4143002A (en)	1979-03-06	Chalk-resistant, medium to dark colored polyurethanes, polymer/polyol and polyisocyanate compositions for use in producing same and methods for making said polyurethanes
EP0343180A1 (en)	1989-11-29	PROCESS FOR FORMING THERMOFORMABLE POLYURETHANE FOAM OBJECTS.

Legal Events

Date	Code	Title	Description
1997-07-22	MKEX	Expiry