CA2139379A1 - Monomeres et polymeres a fonction anhydre; compositions reactives preparees a partir de ces produits - Google Patents

Monomeres et polymeres a fonction anhydre; compositions reactives preparees a partir de ces produits

Info

Publication number: CA2139379A1
Authority: CA; Canada
Prior art keywords: anhydride; functional; monomer; curable composition; hydroxy
Prior art date: 1994-01-03
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 2139379

Other languages

English (en)

Inventor

Rodney M. Harris

Mohamad D. Shalati

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.)

Sherwin Williams Co

Original Assignee

Individual

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.)

1994-01-03

Filing date

1994-12-30

Publication date

1995-07-04

1994-12-30 Application filed by Individual filed Critical Individual

1995-07-04 Publication of CA2139379A1 publication Critical patent/CA2139379A1/fr

Status Abandoned legal-status Critical Current

Links

239000000178 monomer Substances 0.000 title claims abstract description 205
239000000203 mixture Substances 0.000 title claims abstract description 118
229920000642 polymer Polymers 0.000 title claims abstract description 49
229920001002 functional polymer Polymers 0.000 claims description 126
150000008064 anhydrides Chemical class 0.000 claims description 100
150000001875 compounds Chemical class 0.000 claims description 88
238000006243 chemical reaction Methods 0.000 claims description 68
-1 vinyl m-chlorobenzoate Chemical compound 0.000 claims description 57
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 45
239000002253 acid Chemical class 0.000 claims description 44
229920000647 polyepoxide Polymers 0.000 claims description 42
239000000758 substrate Substances 0.000 claims description 40
NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 36
125000003700 epoxy group Chemical group 0.000 claims description 34
239000003054 catalyst Substances 0.000 claims description 26
238000006116 polymerization reaction Methods 0.000 claims description 26
238000000034 method Methods 0.000 claims description 23
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 22
239000001257 hydrogen Substances 0.000 claims description 20
229910052739 hydrogen Inorganic materials 0.000 claims description 20
238000007342 radical addition reaction Methods 0.000 claims description 19
150000003254 radicals Chemical class 0.000 claims description 19
239000000047 product Substances 0.000 claims description 18
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 17
239000002954 polymerization reaction product Substances 0.000 claims description 17
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
229920001577 copolymer Polymers 0.000 claims description 13
FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims description 13
229940014800 succinic anhydride Drugs 0.000 claims description 13
CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 12
239000011541 reaction mixture Substances 0.000 claims description 11
238000012644 addition polymerization Methods 0.000 claims description 9
229920000768 polyamine Polymers 0.000 claims description 8
150000003839 salts Chemical class 0.000 claims description 8
229920002554 vinyl polymer Polymers 0.000 claims description 8
JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 claims description 7
PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 claims description 7
SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 6
ZLZNCYMZVRTFQU-UHFFFAOYSA-N 3-(3-bromopropyl)oxolane-2,5-dione Chemical group BrCCCC1CC(=O)OC1=O ZLZNCYMZVRTFQU-UHFFFAOYSA-N 0.000 claims description 6
BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 claims description 6
125000002843 carboxylic acid group Chemical group 0.000 claims description 6
238000007334 copolymerization reaction Methods 0.000 claims description 6
125000000524 functional group Chemical group 0.000 claims description 6
230000008569 process Effects 0.000 claims description 6
QYQMXYXBPWEJRN-UHFFFAOYSA-N 3-(2,5-dioxooxolan-3-yl)propyl 2-methylprop-2-enoate Chemical group CC(=C)C(=O)OCCCC1CC(=O)OC1=O QYQMXYXBPWEJRN-UHFFFAOYSA-N 0.000 claims description 5
VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims description 5
XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 claims description 5
CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 claims description 5
230000000379 polymerizing effect Effects 0.000 claims description 5
GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 claims description 4
HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 4
NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 4
BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 claims description 4
UIWXSTHGICQLQT-UHFFFAOYSA-N ethenyl propanoate Chemical compound CCC(=O)OC=C UIWXSTHGICQLQT-UHFFFAOYSA-N 0.000 claims description 4
SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 claims description 4
NHARPDSAXCBDDR-UHFFFAOYSA-N propyl 2-methylprop-2-enoate Chemical compound CCCOC(=O)C(C)=C NHARPDSAXCBDDR-UHFFFAOYSA-N 0.000 claims description 4
CFVWNXQPGQOHRJ-UHFFFAOYSA-N 2-methylpropyl prop-2-enoate Chemical compound CC(C)COC(=O)C=C CFVWNXQPGQOHRJ-UHFFFAOYSA-N 0.000 claims description 3
FIXKCCRANLATRP-UHFFFAOYSA-N 3,5,5-trimethylhexyl prop-2-enoate Chemical compound CC(C)(C)CC(C)CCOC(=O)C=C FIXKCCRANLATRP-UHFFFAOYSA-N 0.000 claims description 3
GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 claims description 3
IAXXETNIOYFMLW-COPLHBTASA-N [(1s,3s,4s)-4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl] 2-methylprop-2-enoate Chemical compound C1C[C@]2(C)[C@@H](OC(=O)C(=C)C)C[C@H]1C2(C)C IAXXETNIOYFMLW-COPLHBTASA-N 0.000 claims description 3
WNMORWGTPVWAIB-UHFFFAOYSA-N ethenyl 2-methylpropanoate Chemical compound CC(C)C(=O)OC=C WNMORWGTPVWAIB-UHFFFAOYSA-N 0.000 claims description 3
MEGHWIAOTJPCHQ-UHFFFAOYSA-N ethenyl butanoate Chemical compound CCCC(=O)OC=C MEGHWIAOTJPCHQ-UHFFFAOYSA-N 0.000 claims description 3
229940119545 isobornyl methacrylate Drugs 0.000 claims description 3
FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 claims description 3
238000002156 mixing Methods 0.000 claims description 3
ULDDEWDFUNBUCM-UHFFFAOYSA-N pentyl prop-2-enoate Chemical compound CCCCCOC(=O)C=C ULDDEWDFUNBUCM-UHFFFAOYSA-N 0.000 claims description 3
LYBIZMNPXTXVMV-UHFFFAOYSA-N propan-2-yl prop-2-enoate Chemical compound CC(C)OC(=O)C=C LYBIZMNPXTXVMV-UHFFFAOYSA-N 0.000 claims description 3
PNXMTCDJUBJHQJ-UHFFFAOYSA-N propyl prop-2-enoate Chemical compound CCCOC(=O)C=C PNXMTCDJUBJHQJ-UHFFFAOYSA-N 0.000 claims description 3
239000011253 protective coating Substances 0.000 claims description 3
238000010526 radical polymerization reaction Methods 0.000 claims description 3
239000004971 Cross linker Substances 0.000 claims description 2
KOZCZZVUFDCZGG-UHFFFAOYSA-N vinyl benzoate Chemical compound C=COC(=O)C1=CC=CC=C1 KOZCZZVUFDCZGG-UHFFFAOYSA-N 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 claims 1
YXFVVABEGXRONW-UHFFFAOYSA-N toluene Substances CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 64
238000000576 coating method Methods 0.000 description 26
229920005862 polyol Polymers 0.000 description 23
239000000463 material Substances 0.000 description 20
150000003077 polyols Chemical class 0.000 description 20
239000004593 Epoxy Substances 0.000 description 18
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
239000002904 solvent Substances 0.000 description 15
239000011248 coating agent Substances 0.000 description 14
150000007513 acids Chemical class 0.000 description 12
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 11
229920000728 polyester Polymers 0.000 description 10
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 9
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
150000001412 amines Chemical group 0.000 description 9
MCTWTZJPVLRJOU-UHFFFAOYSA-N 1-methyl-1H-imidazole Chemical compound CN1C=CN=C1 MCTWTZJPVLRJOU-UHFFFAOYSA-N 0.000 description 8
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
150000002118 epoxides Chemical class 0.000 description 8
239000000049 pigment Substances 0.000 description 8
230000009257 reactivity Effects 0.000 description 8
229920002732 Polyanhydride Polymers 0.000 description 7
125000001931 aliphatic group Chemical group 0.000 description 7
239000008199 coating composition Substances 0.000 description 7
150000002148 esters Chemical class 0.000 description 7
150000003335 secondary amines Chemical group 0.000 description 7
239000007787 solid Substances 0.000 description 7
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 7
NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 6
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
239000002585 base Substances 0.000 description 6
238000001035 drying Methods 0.000 description 6
239000003999 initiator Substances 0.000 description 6
239000003921 oil Substances 0.000 description 6
229920001228 polyisocyanate Polymers 0.000 description 6
239000005056 polyisocyanate Substances 0.000 description 6
238000002360 preparation method Methods 0.000 description 6
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 5
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 5
239000004322 Butylated hydroxytoluene Substances 0.000 description 5
NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 5
235000010354 butylated hydroxytoluene Nutrition 0.000 description 5
229940095259 butylated hydroxytoluene Drugs 0.000 description 5
239000003795 chemical substances by application Substances 0.000 description 5
238000004132 cross linking Methods 0.000 description 5
229910000042 hydrogen bromide Inorganic materials 0.000 description 5
LLLCSBYSPJHDJX-UHFFFAOYSA-M potassium;2-methylprop-2-enoate Chemical compound [K+].CC(=C)C([O-])=O LLLCSBYSPJHDJX-UHFFFAOYSA-M 0.000 description 5
239000000126 substance Substances 0.000 description 5
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 5
229940086542 triethylamine Drugs 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 4
OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 4
SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 4
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 4
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
229940048053 acrylate Drugs 0.000 description 4
239000000654 additive Substances 0.000 description 4
WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 4
125000003342 alkenyl group Chemical group 0.000 description 4
HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 description 4
WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 4
150000001735 carboxylic acids Chemical class 0.000 description 4
239000003431 cross linking reagent Substances 0.000 description 4
239000012442 inert solvent Substances 0.000 description 4
239000007788 liquid Substances 0.000 description 4
229910052943 magnesium sulfate Inorganic materials 0.000 description 4
235000019341 magnesium sulphate Nutrition 0.000 description 4
229940102838 methylmethacrylate Drugs 0.000 description 4
DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 4
229910052757 nitrogen Inorganic materials 0.000 description 4
BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 4
150000002978 peroxides Chemical class 0.000 description 4
XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 4
150000003141 primary amines Chemical class 0.000 description 4
239000011780 sodium chloride Substances 0.000 description 4
150000003512 tertiary amines Chemical class 0.000 description 4
239000003039 volatile agent Substances 0.000 description 4
YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 3
FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 3
WUMMIJWEUDHZCL-UHFFFAOYSA-N 3-prop-2-enyloxolane-2,5-dione Chemical compound C=CCC1CC(=O)OC1=O WUMMIJWEUDHZCL-UHFFFAOYSA-N 0.000 description 3
OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 3
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 3
UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 3
229920006397 acrylic thermoplastic Polymers 0.000 description 3
150000008044 alkali metal hydroxides Chemical class 0.000 description 3
125000003277 amino group Chemical group 0.000 description 3
125000003118 aryl group Chemical group 0.000 description 3
235000019400 benzoyl peroxide Nutrition 0.000 description 3
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
239000003085 diluting agent Substances 0.000 description 3
150000002009 diols Chemical class 0.000 description 3
238000005886 esterification reaction Methods 0.000 description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 3
239000007789 gas Substances 0.000 description 3
238000010438 heat treatment Methods 0.000 description 3
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 3
239000011976 maleic acid Substances 0.000 description 3
238000004519 manufacturing process Methods 0.000 description 3
239000012299 nitrogen atmosphere Substances 0.000 description 3
RPQRDASANLAFCM-UHFFFAOYSA-N oxiran-2-ylmethyl prop-2-enoate Chemical compound C=CC(=O)OCC1CO1 RPQRDASANLAFCM-UHFFFAOYSA-N 0.000 description 3
229920003229 poly(methyl methacrylate) Polymers 0.000 description 3
229920000058 polyacrylate Polymers 0.000 description 3
239000007921 spray Substances 0.000 description 3
150000005846 sugar alcohols Polymers 0.000 description 3
ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 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
VHSHLMUCYSAUQU-UHFFFAOYSA-N 2-hydroxypropyl methacrylate Chemical compound CC(O)COC(=O)C(C)=C VHSHLMUCYSAUQU-UHFFFAOYSA-N 0.000 description 2
FRIBMENBGGCKPD-UHFFFAOYSA-N 3-(2,3-dimethoxyphenyl)prop-2-enal Chemical compound COC1=CC=CC(C=CC=O)=C1OC FRIBMENBGGCKPD-UHFFFAOYSA-N 0.000 description 2
YXALYBMHAYZKAP-UHFFFAOYSA-N 7-oxabicyclo[4.1.0]heptan-4-ylmethyl 7-oxabicyclo[4.1.0]heptane-4-carboxylate Chemical compound C1CC2OC2CC1C(=O)OCC1CC2OC2CC1 YXALYBMHAYZKAP-UHFFFAOYSA-N 0.000 description 2
KNDQHSIWLOJIGP-UHFFFAOYSA-N 826-62-0 Chemical compound C1C2C3C(=O)OC(=O)C3C1C=C2 KNDQHSIWLOJIGP-UHFFFAOYSA-N 0.000 description 2
KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 2
UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
ALQSHHUCVQOPAS-UHFFFAOYSA-N Pentane-1,5-diol Chemical compound OCCCCCO ALQSHHUCVQOPAS-UHFFFAOYSA-N 0.000 description 2
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 2
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
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239000002244 precipitate Substances 0.000 description 1
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FBCQUCJYYPMKRO-UHFFFAOYSA-N prop-2-enyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC=C FBCQUCJYYPMKRO-UHFFFAOYSA-N 0.000 description 1
HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
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AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 1
150000003242 quaternary ammonium salts Chemical class 0.000 description 1
230000005855 radiation Effects 0.000 description 1
239000000376 reactant Substances 0.000 description 1
229920005989 resin Polymers 0.000 description 1
239000011347 resin Substances 0.000 description 1
239000006254 rheological additive Substances 0.000 description 1
239000002455 scale inhibitor Substances 0.000 description 1
229940116351 sebacate Drugs 0.000 description 1
CXMXRPHRNRROMY-UHFFFAOYSA-L sebacate(2-) Chemical compound [O-]C(=O)CCCCCCCCC([O-])=O CXMXRPHRNRROMY-UHFFFAOYSA-L 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
238000004513 sizing Methods 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
230000006641 stabilisation Effects 0.000 description 1
238000011105 stabilization Methods 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
238000003860 storage Methods 0.000 description 1
239000001384 succinic acid Substances 0.000 description 1
RINCXYDBBGOEEQ-UHFFFAOYSA-N succinic anhydride Chemical group O=C1CCC(=O)O1 RINCXYDBBGOEEQ-UHFFFAOYSA-N 0.000 description 1
239000000725 suspension Substances 0.000 description 1
239000012209 synthetic fiber Substances 0.000 description 1
229920002994 synthetic fiber Polymers 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
SJMYWORNLPSJQO-UHFFFAOYSA-N tert-butyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(C)(C)C SJMYWORNLPSJQO-UHFFFAOYSA-N 0.000 description 1
GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 description 1
AUHHYELHRWCWEZ-UHFFFAOYSA-N tetrachlorophthalic anhydride Chemical compound ClC1=C(Cl)C(Cl)=C2C(=O)OC(=O)C2=C1Cl AUHHYELHRWCWEZ-UHFFFAOYSA-N 0.000 description 1
FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 1
DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
229920001169 thermoplastic Polymers 0.000 description 1
229920001187 thermosetting polymer Polymers 0.000 description 1
239000004416 thermosoftening plastic Substances 0.000 description 1
UIERETOOQGIECD-ONEGZZNKSA-N tiglic acid group Chemical group C(\C(\C)=C\C)(=O)O UIERETOOQGIECD-ONEGZZNKSA-N 0.000 description 1
150000003606 tin compounds Chemical class 0.000 description 1
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 1
239000004408 titanium dioxide Substances 0.000 description 1
DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical class CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
ZFDIRQKJPRINOQ-UHFFFAOYSA-N transbutenic acid ethyl ester Natural products CCOC(=O)C=CC ZFDIRQKJPRINOQ-UHFFFAOYSA-N 0.000 description 1
238000012546 transfer Methods 0.000 description 1
ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
239000013638 trimer Substances 0.000 description 1
QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
229960004418 trolamine Drugs 0.000 description 1
AVWRKZWQTYIKIY-UHFFFAOYSA-N urea-1-carboxylic acid Chemical compound NC(=O)NC(O)=O AVWRKZWQTYIKIY-UHFFFAOYSA-N 0.000 description 1
150000003673 urethanes Chemical class 0.000 description 1
238000005292 vacuum distillation Methods 0.000 description 1
229920006163 vinyl copolymer Polymers 0.000 description 1
229920001567 vinyl ester resin Polymers 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000001993 wax Substances 0.000 description 1
239000011787 zinc oxide Substances 0.000 description 1

Landscapes

Epoxy Resins (AREA)
Paints Or Removers (AREA)
Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

CA 2139379 1994-01-03 1994-12-30 Monomeres et polymeres a fonction anhydre; compositions reactives preparees a partir de ces produits Abandoned CA2139379A1 (fr)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date
US17605094A	1994-01-03	1994-01-03
US08/176,050		1994-01-03
US29352994A	1994-08-19	1994-08-19
US08/293,529		1994-08-19

Publications (1)

Publication Number	Publication Date
CA2139379A1 true CA2139379A1 (fr)	1995-07-04

Family

ID=26871820

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA 2139379 Abandoned CA2139379A1 (fr)	1994-01-03	1994-12-30	Monomeres et polymeres a fonction anhydre; compositions reactives preparees a partir de ces produits

Country Status (1)

Country	Link
CA (1)	CA2139379A1 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JP2005298393A (ja) *	2004-04-09	2005-10-27	Osaka Organic Chem Ind Ltd	（メタ）アクリル酸エステルの製造法
JP2010265282A (ja) *	2010-06-25	2010-11-25	Osaka Organic Chem Ind Ltd	（メタ）アクリル酸エステルの製造法

1994
- 1994-12-30 CA CA 2139379 patent/CA2139379A1/fr not_active Abandoned

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JP2005298393A (ja) *	2004-04-09	2005-10-27	Osaka Organic Chem Ind Ltd	（メタ）アクリル酸エステルの製造法
JP2010265282A (ja) *	2010-06-25	2010-11-25	Osaka Organic Chem Ind Ltd	（メタ）アクリル酸エステルの製造法

Legal Events

Date	Code	Title	Description
2001-12-31	FZDE	Dead

Publication	Publication Date	Title
EP0316873B1 (fr)	1993-10-06	Revêtements réactifs contenant un composé acide, un composé anhydride, un composé époxyde et un composé hydroxy
US4859758A (en)	1989-08-22	Acid-functional polymers derived from cellulose ester-unsaturated alcohol copolymers, which are reacted with cyclic anhydrides
US6235846B1 (en)	2001-05-22	Anhydride-functional addition polymer, epoxy compound and polyhydroxy compound
US5550195A (en)	1996-08-27	Graft copolymers having anhydride functionality
US5609963A (en)	1997-03-11	Anhydride-functional monomers and polymers and reactive compositions prepared from same
US5043220A (en)	1991-08-27	Substrate coated with a basecoat and/or a clearcoat of an acid-functional compound, an anhydride-functional compound, an epoxy-functional compound and a hydroxy-functional compound
EP0532899B1 (fr)	1994-07-20	Procédé de prolongation de la vie en pot de mélanges de polyol-polyisocyanate
US4605719A (en)	1986-08-12	Liquid, curable coating composition based on a hydroxyl groups-containing addition polymer as binder
EP0316874B1 (fr)	1994-02-16	Revêtements réactifs
US5444139A (en)	1995-08-22	Anhydride-functional polymers derived from alkenyl succinic anhydride
US5086144A (en)	1992-02-04	Acid-functional polymers derived from cellulose acetate butyrate unsaturated alcohol copolymers and coatings prepared from same
US4946744A (en)	1990-08-07	Substrate coated with a clearcoat/basecoat composition comprising an anhydride-functional compound and an hydroxy-functional compound
US5863998A (en)	1999-01-26	Dicarboxylic acid-functional monomers and polymers prepared from same
US5516846A (en)	1996-05-14	Reactive coatings comprising an acid-functional component, an anhydride-functional component and a monoepoxy functional compound
US5418307A (en)	1995-05-23	Hydrogenated polymers having acid functionality
US5480951A (en)	1996-01-02	Curable compositions incorporating anhydride-functional polymers derived from alkenyl succinic anhydride
CA2139379A1 (fr)	1995-07-04	Monomeres et polymeres a fonction anhydre; compositions reactives preparees a partir de ces produits
US5633091A (en)	1997-05-27	Graft copolymers having anhydride functionality
US5418306A (en)	1995-05-23	Acid-functional polymers derived from anhydride-functional polymers comprising ene reaction products of unsaturated anhydrides and polyolefins and curable compositions prepared from same
US5510440A (en)	1996-04-23	Styrene-based dicarboxylic acid-functional monomers and polymers prepared from same
US5405973A (en)	1995-04-11	Vinylbenzyl group-containing succinic anhydride
US5679742A (en)	1997-10-21	Hydrogenated polymers having anhydride functionality
CA1334462C (fr)	1995-02-14	Liant resinique reticulable et dilue dans l'eau
US5391818A (en)	1995-02-21	Tricarboxylic acid-functional monomers and polymers prepared from same
US4912160A (en)	1990-03-27	Acid-functional polymers from hydroxy polymers and cyclic anhydrides

CA2139379A1 - Monomeres et polymeres a fonction anhydre; compositions reactives preparees a partir de ces produits - Google Patents

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