CA1042134A - Polyols de polyepoxide et de caprolactone comme produits de revetement - Google Patents

Polyols de polyepoxide et de caprolactone comme produits de revetement

Info

Publication number: CA1042134A
Authority: CA; Canada
Prior art keywords: polyol; reaction; caprolactone; coatings; polyepoxide
Prior art date: 1973-11-14
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

CA292,318A

Other languages

English (en)

Inventor

Richard M. Gerkin

Lowell R. Comstock

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.)

1973-11-14

Filing date

1977-12-02

Publication date

1978-11-07

1973-11-14 Priority claimed from US415791A external-priority patent/US3896303A/en

1977-12-02 Application filed by Union Carbide Corp filed Critical Union Carbide Corp

1978-11-07 Application granted granted Critical

1978-11-07 Publication of CA1042134A publication Critical patent/CA1042134A/fr

Status Expired legal-status Critical Current

Links

229920005862 polyol Polymers 0.000 title claims abstract description 122
238000000576 coating method Methods 0.000 title abstract description 77
-1 caprolactone polyol Chemical class 0.000 claims abstract description 55
238000006243 chemical reaction Methods 0.000 claims abstract description 42
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 39
239000000203 mixture Substances 0.000 claims abstract description 36
229920000647 polyepoxide Polymers 0.000 claims abstract description 35
PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 claims abstract description 24
XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 claims abstract description 15
239000007795 chemical reaction product Substances 0.000 claims abstract description 12
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 10
239000001257 hydrogen Substances 0.000 claims abstract description 10
150000003077 polyols Chemical class 0.000 claims description 84
239000005056 polyisocyanate Substances 0.000 claims description 37
229920001228 polyisocyanate Polymers 0.000 claims description 34
239000000376 reactant Substances 0.000 claims description 28
239000003054 catalyst Substances 0.000 claims description 20
125000003700 epoxy group Chemical group 0.000 claims description 20
125000004432 carbon atom Chemical group C* 0.000 claims description 16
239000008199 coating composition Substances 0.000 claims description 10
ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 claims description 7
239000011527 polyurethane coating Substances 0.000 claims description 6
125000000217 alkyl group Chemical group 0.000 claims description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
125000001931 aliphatic group Chemical group 0.000 claims description 3
OHJMTUPIZMNBFR-UHFFFAOYSA-N biuret Chemical compound NC(=O)NC(N)=O OHJMTUPIZMNBFR-UHFFFAOYSA-N 0.000 claims description 3
230000000694 effects Effects 0.000 claims description 3
229930195733 hydrocarbon Natural products 0.000 claims description 3
239000004215 Carbon black (E152) Substances 0.000 claims description 2
239000000047 product Substances 0.000 abstract description 28
238000009472 formulation Methods 0.000 abstract description 14
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract description 5
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239000004814 polyurethane Substances 0.000 abstract description 5
229920002635 polyurethane Polymers 0.000 abstract description 4
239000011248 coating agent Substances 0.000 description 33
JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 24
150000001875 compounds Chemical class 0.000 description 16
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 12
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239000003999 initiator Substances 0.000 description 11
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RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
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125000003118 aryl group Chemical group 0.000 description 7
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125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
239000000126 substance Substances 0.000 description 7
KSBAEPSJVUENNK-UHFFFAOYSA-L tin(ii) 2-ethylhexanoate Chemical compound [Sn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O KSBAEPSJVUENNK-UHFFFAOYSA-L 0.000 description 7
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
230000000052 comparative effect Effects 0.000 description 6
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230000000704 physical effect Effects 0.000 description 6
238000012360 testing method Methods 0.000 description 6
239000004593 Epoxy Substances 0.000 description 5
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical class C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 5
ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical class [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 5
229910052799 carbon Inorganic materials 0.000 description 5
ZWAJLVLEBYIOTI-UHFFFAOYSA-N cyclohexene oxide Chemical compound C1CCCC2OC21 ZWAJLVLEBYIOTI-UHFFFAOYSA-N 0.000 description 5
239000003085 diluting agent Substances 0.000 description 5
239000000049 pigment Substances 0.000 description 5
229940113165 trimethylolpropane Drugs 0.000 description 5
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 4
241000219198 Brassica Species 0.000 description 4
235000003351 Brassica cretica Nutrition 0.000 description 4
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WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 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
229910052782 aluminium Inorganic materials 0.000 description 4
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 4
QKSKPIVNLNLAAV-UHFFFAOYSA-N bis(2-chloroethyl) sulfide Chemical compound ClCCSCCCl QKSKPIVNLNLAAV-UHFFFAOYSA-N 0.000 description 4
150000007942 carboxylates Chemical group 0.000 description 4
239000012975 dibutyltin dilaurate Substances 0.000 description 4
150000002148 esters Chemical class 0.000 description 4
229910052740 iodine Inorganic materials 0.000 description 4
239000011630 iodine Substances 0.000 description 4
235000010460 mustard Nutrition 0.000 description 4
229920001296 polysiloxane Polymers 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
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OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
239000002253 acid Substances 0.000 description 3
239000012948 isocyanate Substances 0.000 description 3
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239000007788 liquid Substances 0.000 description 3
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VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
125000000466 oxiranyl group Chemical group 0.000 description 3
238000002360 preparation method Methods 0.000 description 3
229920006395 saturated elastomer Polymers 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
239000008096 xylene Substances 0.000 description 3
ARXKVVRQIIOZGF-UHFFFAOYSA-N 1,2,4-butanetriol Chemical compound OCCC(O)CO ARXKVVRQIIOZGF-UHFFFAOYSA-N 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
238000005299 abrasion Methods 0.000 description 2
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
239000000460 chlorine Chemical group 0.000 description 2
FWFSEYBSWVRWGL-UHFFFAOYSA-N cyclohexene oxide Natural products O=C1CCCC=C1 FWFSEYBSWVRWGL-UHFFFAOYSA-N 0.000 description 2
150000001991 dicarboxylic acids Chemical class 0.000 description 2
125000005442 diisocyanate group Chemical group 0.000 description 2
238000001035 drying Methods 0.000 description 2
150000002118 epoxides Chemical class 0.000 description 2
239000004744 fabric Substances 0.000 description 2
239000011521 glass Substances 0.000 description 2
238000000227 grinding Methods 0.000 description 2
150000002431 hydrogen Chemical class 0.000 description 2
238000007654 immersion Methods 0.000 description 2
150000002500 ions Chemical class 0.000 description 2
150000002576 ketones Chemical class 0.000 description 2
239000010985 leather Substances 0.000 description 2
239000003921 oil Substances 0.000 description 2
235000019198 oils Nutrition 0.000 description 2
XNLICIUVMPYHGG-UHFFFAOYSA-N pentan-2-one Chemical compound CCCC(C)=O XNLICIUVMPYHGG-UHFFFAOYSA-N 0.000 description 2
229920000768 polyamine Polymers 0.000 description 2
229920005906 polyester polyol Polymers 0.000 description 2
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150000003839 salts Chemical class 0.000 description 2
238000010561 standard procedure Methods 0.000 description 2
239000004408 titanium dioxide Substances 0.000 description 2
IAYSVYVUTWSJLY-UHFFFAOYSA-N (5-methyl-7-oxabicyclo[4.1.0]heptan-3-yl)methyl 5-methyl-7-oxabicyclo[4.1.0]heptane-3-carboxylate Chemical compound C1C2OC2C(C)CC1C(=O)OCC1CC(C)C2OC2C1 IAYSVYVUTWSJLY-UHFFFAOYSA-N 0.000 description 1
ZEMGLXWBJVLTKT-UHFFFAOYSA-N (6-methyl-7-oxabicyclo[4.1.0]heptan-4-yl)methyl 6-methyl-7-oxabicyclo[4.1.0]heptane-4-carboxylate Chemical compound C1CC2OC2(C)CC1C(=O)OCC1CC(C)(O2)C2CC1 ZEMGLXWBJVLTKT-UHFFFAOYSA-N 0.000 description 1
QKOWXXDOHMJOMQ-UHFFFAOYSA-N 1,3,5-tris(6-isocyanatohexyl)biuret Chemical compound O=C=NCCCCCCNC(=O)N(CCCCCCN=C=O)C(=O)NCCCCCCN=C=O QKOWXXDOHMJOMQ-UHFFFAOYSA-N 0.000 description 1
229940008841 1,6-hexamethylene diisocyanate Drugs 0.000 description 1
DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
VXQILLTWRZPRQF-UHFFFAOYSA-N 2,4-diisocyanato-1-propan-2-ylbenzene Chemical compound CC(C)C1=CC=C(N=C=O)C=C1N=C=O VXQILLTWRZPRQF-UHFFFAOYSA-N 0.000 description 1
OBETXYAYXDNJHR-UHFFFAOYSA-N 2-Ethylhexanoic acid Chemical compound CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 1
SYEWHONLFGZGLK-UHFFFAOYSA-N 2-[1,3-bis(oxiran-2-ylmethoxy)propan-2-yloxymethyl]oxirane Chemical compound C1OC1COCC(OCC1OC1)COCC1CO1 SYEWHONLFGZGLK-UHFFFAOYSA-N 0.000 description 1
SHKUUQIDMUMQQK-UHFFFAOYSA-N 2-[4-(oxiran-2-ylmethoxy)butoxymethyl]oxirane Chemical compound C1OC1COCCCCOCC1CO1 SHKUUQIDMUMQQK-UHFFFAOYSA-N 0.000 description 1
ZJRAAAWYHORFHN-UHFFFAOYSA-N 2-[[2,6-dibromo-4-[2-[3,5-dibromo-4-(oxiran-2-ylmethoxy)phenyl]propan-2-yl]phenoxy]methyl]oxirane Chemical compound C=1C(Br)=C(OCC2OC2)C(Br)=CC=1C(C)(C)C(C=C1Br)=CC(Br)=C1OCC1CO1 ZJRAAAWYHORFHN-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
GZPRASLJQIBVDP-UHFFFAOYSA-N 2-[[4-[2-[4-(oxiran-2-ylmethoxy)cyclohexyl]propan-2-yl]cyclohexyl]oxymethyl]oxirane Chemical compound C1CC(OCC2OC2)CCC1C(C)(C)C(CC1)CCC1OCC1CO1 GZPRASLJQIBVDP-UHFFFAOYSA-N 0.000 description 1
GRWFFFOEIHGUBG-UHFFFAOYSA-N 3,4-Epoxy-6-methylcyclohexylmethyl-3,4-epoxy-6-methylcyclo-hexanecarboxylate Chemical compound C1C2OC2CC(C)C1C(=O)OCC1CC2OC2CC1C GRWFFFOEIHGUBG-UHFFFAOYSA-N 0.000 description 1
UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 1
RRXFVFZYPPCDAW-UHFFFAOYSA-N 4-(7-oxabicyclo[4.1.0]heptan-4-ylmethoxymethyl)-7-oxabicyclo[4.1.0]heptane Chemical compound C1CC2OC2CC1COCC1CC2OC2CC1 RRXFVFZYPPCDAW-UHFFFAOYSA-N 0.000 description 1
HVMHLMJYHBAOPL-UHFFFAOYSA-N 4-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)propan-2-yl]-7-oxabicyclo[4.1.0]heptane Chemical compound C1CC2OC2CC1C(C)(C)C1CC2OC2CC1 HVMHLMJYHBAOPL-UHFFFAOYSA-N 0.000 description 1
OECTYKWYRCHAKR-UHFFFAOYSA-N 4-vinylcyclohexene dioxide Chemical compound C1OC1C1CC2OC2CC1 OECTYKWYRCHAKR-UHFFFAOYSA-N 0.000 description 1
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ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 description 1
229920003270 Cymel® Polymers 0.000 description 1
WPYCRFCQABTEKC-UHFFFAOYSA-N Diglycidyl resorcinol ether Chemical compound C1OC1COC(C=1)=CC=CC=1OCC1CO1 WPYCRFCQABTEKC-UHFFFAOYSA-N 0.000 description 1
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
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NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
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MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
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ISKQADXMHQSTHK-UHFFFAOYSA-N [4-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=C(CN)C=C1 ISKQADXMHQSTHK-UHFFFAOYSA-N 0.000 description 1
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JRPRCOLKIYRSNH-UHFFFAOYSA-N bis(oxiran-2-ylmethyl) benzene-1,2-dicarboxylate Chemical compound C=1C=CC=C(C(=O)OCC2OC2)C=1C(=O)OCC1CO1 JRPRCOLKIYRSNH-UHFFFAOYSA-N 0.000 description 1
GNUXSHVHSXKHPO-UHFFFAOYSA-N bis[(3-methyl-7-oxabicyclo[4.1.0]heptan-4-yl)methyl] butanedioate Chemical compound C1C2OC2CC(C)C1COC(=O)CCC(=O)OCC1CC2OC2CC1C GNUXSHVHSXKHPO-UHFFFAOYSA-N 0.000 description 1
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JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
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238000007598 dipping method Methods 0.000 description 1
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150000002170 ethers Chemical class 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
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238000010438 heat treatment Methods 0.000 description 1
RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
GFMIDCCZJUXASS-UHFFFAOYSA-N hexane-1,1,6-triol Chemical compound OCCCCCC(O)O GFMIDCCZJUXASS-UHFFFAOYSA-N 0.000 description 1
FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
238000010348 incorporation Methods 0.000 description 1
239000003701 inert diluent Substances 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
125000001261 isocyanato group Chemical group *N=C=O 0.000 description 1
NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000004922 lacquer Substances 0.000 description 1
229940070765 laurate Drugs 0.000 description 1
VQPKAMAVKYTPLB-UHFFFAOYSA-N lead;octanoic acid Chemical compound [Pb].CCCCCCCC(O)=O VQPKAMAVKYTPLB-UHFFFAOYSA-N 0.000 description 1
JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 1
150000002739 metals Chemical class 0.000 description 1
239000011707 mineral Substances 0.000 description 1
238000006386 neutralization reaction Methods 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
229940049964 oleate Drugs 0.000 description 1
ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
239000011368 organic material Substances 0.000 description 1
WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 1
125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
230000000737 periodic effect Effects 0.000 description 1
239000003209 petroleum derivative Substances 0.000 description 1
WLJVNTCWHIRURA-UHFFFAOYSA-M pimelate(1-) Chemical compound OC(=O)CCCCCC([O-])=O WLJVNTCWHIRURA-UHFFFAOYSA-M 0.000 description 1
239000004033 plastic Substances 0.000 description 1
229920003023 plastic Polymers 0.000 description 1
239000004014 plasticizer Substances 0.000 description 1
229920001610 polycaprolactone Polymers 0.000 description 1
239000004632 polycaprolactone Substances 0.000 description 1
229920000728 polyester Polymers 0.000 description 1
230000001737 promoting effect Effects 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
238000005070 sampling Methods 0.000 description 1
239000007787 solid Substances 0.000 description 1
235000012424 soybean oil Nutrition 0.000 description 1
239000003549 soybean oil Substances 0.000 description 1
241000894007 species Species 0.000 description 1
235000015096 spirit Nutrition 0.000 description 1
238000005507 spraying Methods 0.000 description 1
150000005846 sugar alcohols Polymers 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
238000010998 test method Methods 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
239000012974 tin catalyst Substances 0.000 description 1
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 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
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
OBPKPFFFOAVXNB-UHFFFAOYSA-N tricyclo[5.2.1.02,6]deca-1,6,8-triene Chemical compound C1C2=CC=C1C1=C2CCC1 OBPKPFFFOAVXNB-UHFFFAOYSA-N 0.000 description 1
QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
150000004072 triols Chemical class 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1
239000011345 viscous material Substances 0.000 description 1
230000000007 visual effect Effects 0.000 description 1
239000002023 wood Substances 0.000 description 1

Landscapes

Polyurethanes Or Polyureas (AREA)

CA292,318A 1973-11-14 1977-12-02 Polyols de polyepoxide et de caprolactone comme produits de revetement Expired CA1042134A (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US415791A US3896303A (en)	1973-11-14	1973-11-14	Polyepoxide-caprolactone polyols and coatings based thereon
CA211,875A CA1042457A (fr)	1973-11-14	1974-10-21	Polyols de polyepoxide-caprolactone et produits de revetement que l'on peut en tirer

Publications (1)

Publication Number	Publication Date
CA1042134A true CA1042134A (fr)	1978-11-07

Family

ID=25667727

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA292,318A Expired CA1042134A (fr)	1973-11-14	1977-12-02	Polyols de polyepoxide et de caprolactone comme produits de revetement

Country Status (1)

Country	Link
CA (1)	CA1042134A (fr)

1977
- 1977-12-02 CA CA292,318A patent/CA1042134A/fr not_active Expired

Publication	Publication Date	Title
US4582888A (en)	1986-04-15	Process for production of isocyanurate ring-containing polyisocyanate and resin composition for urethane paints comprising said polyisocyanate and acrylic polyol
US3896303A (en)	1975-07-22	Polyepoxide-caprolactone polyols and coatings based thereon
US3989676A (en)	1976-11-02	Polyurethane coating formulations based on polyepoxide-caprolactone polyols and polyisocyanates
US4929667A (en)	1990-05-29	Urethane prepolymer composition and a polyurethane coating composition system
KR940008986B1 (ko)	1994-09-28	폴리이소시아네이트-이소시아누레이트 및 그의 제조방법, 이들의 용도
US4296230A (en)	1981-10-20	Polyurethane coatings produced from (1) a polyisocyanate mixture of polyisocyanates from the diphenol methane series and a polyhydroxy polyether containing at least one tertiary amine nitrogen with (2) a polyol in a two component coating system
US4045474A (en)	1977-08-30	Low viscosity poly(epoxide-caprolactone) polyols
CA2387783A1 (fr)	2001-05-10	Composes a base d'isocyanate sequence et compositions contenant ceux-ci
US3830785A (en)	1974-08-20	Thermosetting polyurethane coatings based on blocked cyclo-aliphatic diisocyanates
CA1298025C (fr)	1992-03-24	Compositions de resine thermodurcissable contenues dans un seul contenant
US5756634A (en)	1998-05-26	Liquid one component PU stoving enamels
JPH02163146A (ja)	1990-06-22	塩化ビニル樹脂組成物
US5705593A (en)	1998-01-06	Diphenylmethane diisocyanate based polyisocyanates containing allophanate groups and having blocked isocyanate groups
US3808160A (en)	1974-04-30	Cross-linkable coating composition of a hydroxyl containing polyester and a blocked polyisocyanate
US6441087B1 (en)	2002-08-27	High gloss acrylic coatings with improved impact resistance
JPS5878737A (ja)	1983-05-12	硬化性被覆物及び被覆方法
US20200339835A1 (en)	2020-10-29	Polyurethane coating with a high biosourced monomer content, comprising isosorbide and pentamethylene diisocyanate
KR0176256B1 (ko)	1999-04-01	스토빙래커 결합제 조성물 및 이로부터 피복물을 제조하는 방법
EP0880550B1 (fr)	2000-05-17	Composition de revetement
US3554951A (en)	1971-01-12	Polyester polyurethane lacquers from mixed phthalic acids
US6096835A (en)	2000-08-01	Film forming binder for coating compositions and coating compositions comprising same
CA1299316C (fr)	1992-04-21	Compositions de resine thermodurcissable et metal preenduit de ladite composition
CA1042134A (fr)	1978-11-07	Polyols de polyepoxide et de caprolactone comme produits de revetement
US7071286B2 (en)	2006-07-04	Coating compositions with high solids content for vehicle coating
US4879356A (en)	1989-11-07	Method of manufacturing single-component polyurethane baking enamels