CA1246785A - Melanges de composes renfermant un ether-oxyde vinylique cyclique et d'un compose organique a poly(hydrogene actif) - Google Patents

Melanges de composes renfermant un ether-oxyde vinylique cyclique et d'un compose organique a poly(hydrogene actif)

Info

Publication number: CA1246785A
Authority: CA; Canada
Prior art keywords: composition; vinyl ether; cycloaliphatic; polyol; monoepoxide
Prior art date: 1983-03-29
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

CA000450655A

Other languages

English (en)

Inventor

Joseph V. Koleske

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.)

1983-03-29

Filing date

1984-03-28

Publication date

1988-12-13

1984-03-28 Application filed by Union Carbide Corp filed Critical Union Carbide Corp

1988-12-13 Application granted granted Critical

1988-12-13 Publication of CA1246785A publication Critical patent/CA1246785A/fr

Status Expired legal-status Critical Current

Links

239000000203 mixture Substances 0.000 title claims abstract description 141
150000001875 compounds Chemical class 0.000 title claims abstract description 58
QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 title claims abstract description 46
239000001257 hydrogen Substances 0.000 title claims abstract description 32
229910052739 hydrogen Inorganic materials 0.000 title claims abstract description 32
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 title claims abstract description 28
125000004122 cyclic group Chemical group 0.000 title claims abstract description 23
150000002894 organic compounds Chemical class 0.000 title claims abstract description 20
238000000576 coating method Methods 0.000 claims abstract description 28
229920005862 polyol Polymers 0.000 claims description 134
150000003077 polyols Chemical class 0.000 claims description 116
-1 acrylic polyol Chemical class 0.000 claims description 80
229960000834 vinyl ether Drugs 0.000 claims description 45
229920001610 polycaprolactone Polymers 0.000 claims description 36
239000004632 polycaprolactone Substances 0.000 claims description 36
229920000642 polymer Polymers 0.000 claims description 34
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 28
125000002947 alkylene group Chemical group 0.000 claims description 25
125000004432 carbon atom Chemical group C* 0.000 claims description 25
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 21
229920002554 vinyl polymer Polymers 0.000 claims description 20
125000000217 alkyl group Chemical group 0.000 claims description 19
125000003118 aryl group Chemical group 0.000 claims description 16
239000011248 coating agent Substances 0.000 claims description 16
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 15
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 13
239000004721 Polyphenylene oxide Substances 0.000 claims description 11
229920000570 polyether Polymers 0.000 claims description 11
239000004593 Epoxy Substances 0.000 claims description 10
150000002148 esters Chemical class 0.000 claims description 10
229920005989 resin Polymers 0.000 claims description 9
239000011347 resin Substances 0.000 claims description 9
150000003839 salts Chemical class 0.000 claims description 9
229910052736 halogen Inorganic materials 0.000 claims description 8
150000002367 halogens Chemical class 0.000 claims description 8
125000001424 substituent group Chemical group 0.000 claims description 7
125000003545 alkoxy group Chemical group 0.000 claims description 6
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
239000007795 chemical reaction product Substances 0.000 claims description 6
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
229920003986 novolac Polymers 0.000 claims description 6
229910052760 oxygen Inorganic materials 0.000 claims description 6
239000001301 oxygen Substances 0.000 claims description 6
125000004430 oxygen atom Chemical group O* 0.000 claims description 6
229920000647 polyepoxide Polymers 0.000 claims description 6
238000006116 polymerization reaction Methods 0.000 claims description 6
230000005855 radiation Effects 0.000 claims description 6
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 5
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 5
150000001335 aliphatic alkanes Chemical class 0.000 claims description 5
229910052799 carbon Inorganic materials 0.000 claims description 5
HGCIXCUEYOPUTN-UHFFFAOYSA-N cis-cyclohexene Natural products C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 claims description 5
125000005043 dihydropyranyl group Chemical group O1C(CCC=C1)* 0.000 claims description 5
125000003700 epoxy group Chemical group 0.000 claims description 5
125000001183 hydrocarbyl group Chemical group 0.000 claims description 5
WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 claims description 5
239000004215 Carbon black (E152) Substances 0.000 claims description 4
125000001931 aliphatic group Chemical group 0.000 claims description 4
125000003609 aryl vinyl group Chemical group 0.000 claims description 4
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 4
125000005708 carbonyloxy group Chemical group [*:2]OC([*:1])=O 0.000 claims description 4
239000003822 epoxy resin Substances 0.000 claims 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 claims description 4
229930195733 hydrocarbon Natural products 0.000 claims description 4
229920005906 polyester polyol Polymers 0.000 claims description 4
ORGHESHFQPYLAO-UHFFFAOYSA-N vinyl radical Chemical compound C=[CH] ORGHESHFQPYLAO-UHFFFAOYSA-N 0.000 claims description 4
XMICBFRKICBBKD-UHFFFAOYSA-N 3,4-dihydro-2h-pyran-2-ylmethanol Chemical compound OCC1CCC=CO1 XMICBFRKICBBKD-UHFFFAOYSA-N 0.000 claims description 3
FQYUMYWMJTYZTK-UHFFFAOYSA-N Phenyl glycidyl ether Chemical compound C1OC1COC1=CC=CC=C1 FQYUMYWMJTYZTK-UHFFFAOYSA-N 0.000 claims description 3
125000002877 alkyl aryl group Chemical group 0.000 claims description 3
125000003710 aryl alkyl group Chemical group 0.000 claims description 3
150000007942 carboxylates Chemical class 0.000 claims description 3
150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 3
125000000753 cycloalkyl group Chemical group 0.000 claims description 3
125000005442 diisocyanate group Chemical group 0.000 claims description 3
125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 claims description 3
WJRBRSLFGCUECM-UHFFFAOYSA-N hydantoin Chemical compound O=C1CNC(=O)N1 WJRBRSLFGCUECM-UHFFFAOYSA-N 0.000 claims description 3
229940091173 hydantoin Drugs 0.000 claims description 3
QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 claims description 2
229930003836 cresol Natural products 0.000 claims description 2
125000000623 heterocyclic group Chemical group 0.000 claims description 2
150000002431 hydrogen Chemical group 0.000 claims description 2
AFEQENGXSMURHA-UHFFFAOYSA-N oxiran-2-ylmethanamine Chemical compound NCC1CO1 AFEQENGXSMURHA-UHFFFAOYSA-N 0.000 claims description 2
229920002635 polyurethane Polymers 0.000 claims description 2
229930195734 saturated hydrocarbon Natural products 0.000 claims description 2
150000002924 oxiranes Chemical class 0.000 claims 15
DJUWPHRCMMMSCV-UHFFFAOYSA-N bis(7-oxabicyclo[4.1.0]heptan-4-ylmethyl) hexanedioate Chemical group C1CC2OC2CC1COC(=O)CCCCC(=O)OCC1CC2OC2CC1 DJUWPHRCMMMSCV-UHFFFAOYSA-N 0.000 claims 3
125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 claims 3
239000012954 diazonium Substances 0.000 claims 3
150000001989 diazonium salts Chemical group 0.000 claims 3
YXALYBMHAYZKAP-UHFFFAOYSA-N 7-oxabicyclo[4.1.0]heptan-4-ylmethyl 7-oxabicyclo[4.1.0]heptane-4-carboxylate Chemical group C1CC2OC2CC1C(=O)OCC1CC2OC2CC1 YXALYBMHAYZKAP-UHFFFAOYSA-N 0.000 claims 2
OTLWUWJIIXAOEO-UHFFFAOYSA-N 3,4-dihydro-2h-pyran-2-carboxylic acid Chemical class OC(=O)C1CCC=CO1 OTLWUWJIIXAOEO-UHFFFAOYSA-N 0.000 claims 1
DNWBGZGLCKETOT-UHFFFAOYSA-N cyclohexane;1,3-dioxane Chemical compound C1CCCCC1.C1COCOC1 DNWBGZGLCKETOT-UHFFFAOYSA-N 0.000 claims 1
125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 1
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 34
LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 34
150000002118 epoxides Chemical class 0.000 description 25
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 24
239000000178 monomer Substances 0.000 description 16
239000002253 acid Substances 0.000 description 15
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 11
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 11
HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 10
239000004615 ingredient Substances 0.000 description 10
PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 10
239000008199 coating composition Substances 0.000 description 9
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 8
239000004094 surface-active agent Substances 0.000 description 8
150000007513 acids Chemical class 0.000 description 7
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 7
239000003999 initiator Substances 0.000 description 7
238000000034 method Methods 0.000 description 7
210000004940 nucleus Anatomy 0.000 description 7
150000004072 triols Chemical class 0.000 description 7
OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 6
238000006243 chemical reaction Methods 0.000 description 6
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
150000002596 lactones Chemical class 0.000 description 6
YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 6
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 5
WNLRTRBMVRJNCN-UHFFFAOYSA-L adipate(2-) Chemical compound [O-]C(=O)CCCCC([O-])=O WNLRTRBMVRJNCN-UHFFFAOYSA-L 0.000 description 5
239000000539 dimer Chemical class 0.000 description 5
150000004000 hexols Chemical class 0.000 description 5
229910052751 metal Inorganic materials 0.000 description 5
239000002184 metal Substances 0.000 description 5
OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Substances OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 5
238000002156 mixing Methods 0.000 description 5
229920001228 polyisocyanate Polymers 0.000 description 5
239000005056 polyisocyanate Substances 0.000 description 5
238000002360 preparation method Methods 0.000 description 5
230000002441 reversible effect Effects 0.000 description 5
NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 4
239000002202 Polyethylene glycol Substances 0.000 description 4
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 4
239000003054 catalyst Substances 0.000 description 4
229920001577 copolymer Polymers 0.000 description 4
229940052303 ethers for general anesthesia Drugs 0.000 description 4
238000004519 manufacturing process Methods 0.000 description 4
239000000463 material Substances 0.000 description 4
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
229910052698 phosphorus Inorganic materials 0.000 description 4
229920001223 polyethylene glycol Polymers 0.000 description 4
150000008442 polyphenolic compounds Chemical class 0.000 description 4
235000013824 polyphenols Nutrition 0.000 description 4
229920001451 polypropylene glycol Polymers 0.000 description 4
239000000047 product Substances 0.000 description 4
239000000376 reactant Substances 0.000 description 4
239000007787 solid Substances 0.000 description 4
239000002904 solvent Substances 0.000 description 4
239000000126 substance Substances 0.000 description 4
235000000346 sugar Nutrition 0.000 description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 3
ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 3
GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 3
ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 3
150000001299 aldehydes Chemical class 0.000 description 3
WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 3
150000001721 carbon Chemical group 0.000 description 3
239000001913 cellulose Substances 0.000 description 3
229920002678 cellulose Polymers 0.000 description 3
150000002009 diols Chemical class 0.000 description 3
230000000694 effects Effects 0.000 description 3
150000002334 glycols Chemical class 0.000 description 3
150000002430 hydrocarbons Chemical group 0.000 description 3
239000012948 isocyanate Substances 0.000 description 3
150000002513 isocyanates Chemical class 0.000 description 3
238000005065 mining Methods 0.000 description 3
239000003921 oil Substances 0.000 description 3
239000011574 phosphorus Substances 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
150000003254 radicals Chemical class 0.000 description 3
238000012360 testing method Methods 0.000 description 3
PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
ARXKVVRQIIOZGF-UHFFFAOYSA-N 1,2,4-butanetriol Chemical compound OCCC(O)CO ARXKVVRQIIOZGF-UHFFFAOYSA-N 0.000 description 2
ZWVMLYRJXORSEP-UHFFFAOYSA-N 1,2,6-Hexanetriol Chemical compound OCCCCC(O)CO ZWVMLYRJXORSEP-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
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical group C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
241000518994 Conta Species 0.000 description 2
239000004386 Erythritol Substances 0.000 description 2
UNXHWFMMPAWVPI-UHFFFAOYSA-N Erythritol Natural products OCC(O)C(O)CO UNXHWFMMPAWVPI-UHFFFAOYSA-N 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
AMIMRNSIRUDHCM-UHFFFAOYSA-N Isopropylaldehyde Chemical compound CC(C)C=O AMIMRNSIRUDHCM-UHFFFAOYSA-N 0.000 description 2
STNJBCKSHOAVAJ-UHFFFAOYSA-N Methacrolein Chemical compound CC(=C)C=O STNJBCKSHOAVAJ-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
239000000654 additive Substances 0.000 description 2
125000000732 arylene group Chemical group 0.000 description 2
WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
229910052794 bromium Inorganic materials 0.000 description 2
239000004359 castor oil Substances 0.000 description 2
235000019438 castor oil Nutrition 0.000 description 2
230000003197 catalytic effect Effects 0.000 description 2
125000002091 cationic group Chemical group 0.000 description 2
238000010538 cationic polymerization reaction Methods 0.000 description 2
239000000460 chlorine Substances 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
239000007859 condensation product Substances 0.000 description 2
238000007796 conventional method Methods 0.000 description 2
125000002993 cycloalkylene group Chemical group 0.000 description 2
QSAWQNUELGIYBC-UHFFFAOYSA-N cyclohexane-1,2-dicarboxylic acid Chemical class OC(=O)C1CCCCC1C(O)=O QSAWQNUELGIYBC-UHFFFAOYSA-N 0.000 description 2
230000002939 deleterious effect Effects 0.000 description 2
238000011161 development Methods 0.000 description 2
150000001991 dicarboxylic acids Chemical class 0.000 description 2
SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 2
229920001971 elastomer Polymers 0.000 description 2
238000010894 electron beam technology Methods 0.000 description 2
UNXHWFMMPAWVPI-ZXZARUISSA-N erythritol Chemical compound OC[C@H](O)[C@H](O)CO UNXHWFMMPAWVPI-ZXZARUISSA-N 0.000 description 2
235000019414 erythritol Nutrition 0.000 description 2
229940009714 erythritol Drugs 0.000 description 2
150000002170 ethers Chemical class 0.000 description 2
239000007888 film coating Substances 0.000 description 2
238000009501 film coating Methods 0.000 description 2
235000019256 formaldehyde Nutrition 0.000 description 2
239000011521 glass Substances 0.000 description 2
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229930182470 glycoside Natural products 0.000 description 2
LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical compound O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 description 2
230000005484 gravity Effects 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
ZHQLTKAVLJKSKR-UHFFFAOYSA-N homophthalic acid Chemical compound OC(=O)CC1=CC=CC=C1C(O)=O ZHQLTKAVLJKSKR-UHFFFAOYSA-N 0.000 description 2
150000002500 ions Chemical class 0.000 description 2
125000001261 isocyanato group Chemical group *N=C=O 0.000 description 2
239000007788 liquid Substances 0.000 description 2
HEBKCHPVOIAQTA-UHFFFAOYSA-N meso ribitol Natural products OCC(O)C(O)C(O)CO HEBKCHPVOIAQTA-UHFFFAOYSA-N 0.000 description 2
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125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
125000001477 organic nitrogen group Chemical group 0.000 description 2
150000002989 phenols Chemical class 0.000 description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
150000003022 phthalic acids Chemical class 0.000 description 2
229920000768 polyamine Polymers 0.000 description 2
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235000013849 propane Nutrition 0.000 description 2
125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 2
239000005060 rubber Substances 0.000 description 2
NDVLTYZPCACLMA-UHFFFAOYSA-N silver oxide Chemical compound [O-2].[Ag+].[Ag+] NDVLTYZPCACLMA-UHFFFAOYSA-N 0.000 description 2
239000000758 substrate Substances 0.000 description 2
150000008163 sugars Chemical class 0.000 description 2
RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical class CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 description 2
238000005809 transesterification reaction Methods 0.000 description 2
ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 2
DJKGDNKYTKCJKD-BPOCMEKLSA-N (1s,4r,5s,6r)-1,2,3,4,7,7-hexachlorobicyclo[2.2.1]hept-2-ene-5,6-dicarboxylic acid Chemical compound ClC1=C(Cl)[C@]2(Cl)[C@H](C(=O)O)[C@H](C(O)=O)[C@@]1(Cl)C2(Cl)Cl DJKGDNKYTKCJKD-BPOCMEKLSA-N 0.000 description 1
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JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
MTZUIIAIAKMWLI-UHFFFAOYSA-N 1,2-diisocyanatobenzene Chemical class O=C=NC1=CC=CC=C1N=C=O MTZUIIAIAKMWLI-UHFFFAOYSA-N 0.000 description 1
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Landscapes

Paints Or Removers (AREA)

CA000450655A 1983-03-29 1984-03-28 Melanges de composes renfermant un ether-oxyde vinylique cyclique et d'un compose organique a poly(hydrogene actif) Expired CA1246785A (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US48008183A	1983-03-29	1983-03-29
US480,081		1983-03-29

Publications (1)

Publication Number	Publication Date
CA1246785A true CA1246785A (fr)	1988-12-13

Family

ID=23906603

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000450655A Expired CA1246785A (fr)	1983-03-29	1984-03-28	Melanges de composes renfermant un ether-oxyde vinylique cyclique et d'un compose organique a poly(hydrogene actif)

Country Status (1)

Country	Link
CA (1)	CA1246785A (fr)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2676061A1 (fr) *	1991-05-01	1992-11-06	Allied Signal Inc	Stereolithographie utilisant des polymeres ethers vinyliques-epoxydes.
EP0481476A3 (en) *	1990-10-18	1993-07-28	Union Carbide Chemicals And Plastics Company, Inc.	Trifunctional unsaturated compounds and derivatives thereof
US5510226A (en) *	1991-05-01	1996-04-23	Alliedsignal Inc.	Stereolithography using vinyl ether-epoxide polymers

1984
- 1984-03-28 CA CA000450655A patent/CA1246785A/fr not_active Expired

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0481476A3 (en) *	1990-10-18	1993-07-28	Union Carbide Chemicals And Plastics Company, Inc.	Trifunctional unsaturated compounds and derivatives thereof
FR2676061A1 (fr) *	1991-05-01	1992-11-06	Allied Signal Inc	Stereolithographie utilisant des polymeres ethers vinyliques-epoxydes.
WO1992020014A1 (fr) *	1991-05-01	1992-11-12	Allied-Signal Inc.	Stereolithographie a l'aide de polymeres epoxyde-ether de vinyle
BE1005001A4 (fr) *	1991-05-01	1993-03-16	Allied Signal Inc	Stereolithographie utilisant les polymeres epoxyde-ether vinylique.
GB2273297A (en) *	1991-05-01	1994-06-15	Allied Signal Inc	Stereolithography using vinyl ether-epoxide polymers
US5437964A (en) *	1991-05-01	1995-08-01	Alliedsignal Inc.	Stereolithography using vinyl ether-epoxide polymers
GB2273297B (en) *	1991-05-01	1995-11-22	Allied Signal Inc	Stereolithography using vinyl ether-epoxide polymers
US5510226A (en) *	1991-05-01	1996-04-23	Alliedsignal Inc.	Stereolithography using vinyl ether-epoxide polymers

Legal Events

Date	Code	Title	Description
2005-12-13	MKEX	Expiry

Publication	Publication Date	Title
CA1305823C (fr)	1992-07-28	Melanges photodurcissables d'ethers cycliques et d'epoxydes cycloaliphatiques
US4874798A (en)	1989-10-17	Photocopolymerizable compositions based on epoxy and hydroxyl-containing organic materials and substituted cycloaliphatic monoepoxide reactive diluents
CA1243147A (fr)	1988-10-11	Compositions photocopolymerisables a base de substances organiques epoxydes et hydroxyles, et de derives de substitution de mono-epoxyde cycloaliphatique comme diluants reactifs
US4599401A (en)	1986-07-08	Low viscosity adducts of poly(active hydrogen) organic compounds and a polyepoxide
US4593051A (en)	1986-06-03	Photocopolymerizable compositons based on epoxy and polymer/hydroxyl-containing organic materials
US4707535A (en)	1987-11-17	Low viscosity adducts of a poly(active hydrogen) organic compound and polyepoxide
GB1583413A (en)	1981-01-28	Curable coating compositions based on olefinically unsaturated compounds containing urethane groups
US4622349A (en)	1986-11-11	Blends of epoxides and monoepoxides
CA1246786A (fr)	1988-12-13	Melanges d'epoxydes et de composes renfermant un ether vinylique cyclique
CA1266345A (fr)	1990-02-27	Melanges de composes a base d'oxydes vinyliques cycliques et d'acrylates d'urethane
US4812488A (en)	1989-03-14	Photocopolymerizable compositions based on hydroxyl-containing organic materials and substituted cycloaliphatic monoepoxide reactive diluents
US4818776A (en)	1989-04-04	Photocopolymerizable compositions based on epoxy and hydroxyl-containing organic materials having primary hydroxyl content
US6417243B1 (en)	2002-07-09	Monomers, oligomers and polymers comprising terminal oxirane groups, their process of preparation and their cationic polymerization under irradiation
JPH05306326A (ja)	1993-11-19	硬化性塗料組成物
CA1246785A (fr)	1988-12-13	Melanges de composes renfermant un ether-oxyde vinylique cyclique et d'un compose organique a poly(hydrogene actif)
EP0118044B1 (fr)	1989-11-23	Compositions photo-copolymérisables à base de matériaux organiques contenant de l'époxy et de l'hydroxyle, à contenu d'hydroxyle primaire
CA1243146A (fr)	1988-10-11	Compositions photocopolymerisables a base de substances organiques hydroxyles et de derives de substitution de mono-epoxyde cycloaliphatique comme diluants reactifs
US4814361A (en)	1989-03-21	Blends of epoxides and monoepoxides
US4786705A (en)	1988-11-22	Low viscosity adducts of a poly(active hydrogen) organic compound and a polyepoxide
US4840978A (en)	1989-06-20	Blends, of cyclic vinyl ether containing compounds and epoxides
KR20060133482A (ko)	2006-12-26	알칼리 현상성 감광성 수지조성물
CA1246292A (fr)	1988-12-06	Melanges a base d'ethers-oxydes vinyliques lineaires et de composes renfermant des ethers- oxydes vinyliques cycliques
JPS5840570B2 (ja)	1983-09-06	コウカセイジユシソセイブツ
JP4059407B2 (ja)	2008-03-12	光重合性組成物
JPH0931292A (ja)	1997-02-04	硬化性樹脂組成物