CA2122985C - Composition de resine, composition durcissable et composition de revetement - Google Patents

Composition de resine, composition durcissable et composition de revetement

Info

Publication number: CA2122985C
Authority: CA; Canada
Prior art keywords: compound; group; weight; fluorine; resin
Prior art date: 1989-03-03
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.): Expired - Fee Related

Application number

CA002122985A

Other languages

English (en)

Other versions

CA2122985A1 (fr

Inventor

Akimasa Nakahata

Nobushige Numa

Masahiro Yamane

Osamu Isozaki

Noboru Nakai

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.)

Kansai Paint Co Ltd

Original Assignee

Kansai Paint Co Ltd

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.)

1989-03-03

Filing date

1990-03-02

Publication date

1997-12-16

1989-03-03 Priority claimed from JP1052537A external-priority patent/JP2787326B2/ja

1990-03-02 Application filed by Kansai Paint Co Ltd filed Critical Kansai Paint Co Ltd

1990-09-04 Publication of CA2122985A1 publication Critical patent/CA2122985A1/fr

1997-12-16 Application granted granted Critical

1997-12-16 Publication of CA2122985C publication Critical patent/CA2122985C/fr

2010-03-02 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

Links

239000000203 mixture Substances 0.000 title claims abstract description 118
239000011342 resin composition Substances 0.000 title claims abstract description 66
239000008199 coating composition Substances 0.000 title claims abstract description 55
150000001875 compounds Chemical class 0.000 claims abstract description 303
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 127
229910052731 fluorine Inorganic materials 0.000 claims abstract description 72
229920005989 resin Polymers 0.000 claims abstract description 68
239000011347 resin Substances 0.000 claims abstract description 68
YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims abstract description 65
239000011737 fluorine Substances 0.000 claims abstract description 64
125000003700 epoxy group Chemical group 0.000 claims abstract description 56
239000013522 chelant Substances 0.000 claims abstract description 55
229910052751 metal Inorganic materials 0.000 claims abstract description 30
239000002184 metal Substances 0.000 claims abstract description 30
239000000049 pigment Substances 0.000 claims abstract description 22
239000000178 monomer Substances 0.000 claims description 147
125000005372 silanol group Chemical group 0.000 claims description 23
229910052782 aluminium Inorganic materials 0.000 claims description 22
125000000217 alkyl group Chemical group 0.000 claims description 20
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 20
XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 17
229910052710 silicon Inorganic materials 0.000 claims description 17
125000001153 fluoro group Chemical group F* 0.000 claims description 8
125000002723 alicyclic group Chemical group 0.000 claims description 5
125000003709 fluoroalkyl group Chemical group 0.000 claims description 5
125000001188 haloalkyl group Chemical group 0.000 claims description 5
229910052801 chlorine Inorganic materials 0.000 claims description 4
229910052739 hydrogen Inorganic materials 0.000 claims description 4
239000003446 ligand Substances 0.000 claims description 2
BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical group [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 abstract description 59
229910000077 silane Inorganic materials 0.000 abstract description 29
239000003054 catalyst Substances 0.000 abstract description 3
SNVLJLYUUXKWOJ-UHFFFAOYSA-N methylidenecarbene Chemical compound C=[C] SNVLJLYUUXKWOJ-UHFFFAOYSA-N 0.000 description 105
238000000576 coating method Methods 0.000 description 55
-1 diisocyanate compound Chemical class 0.000 description 53
229920001577 copolymer Polymers 0.000 description 48
239000011248 coating agent Substances 0.000 description 46
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 45
239000004593 Epoxy Substances 0.000 description 35
239000000047 product Substances 0.000 description 35
125000001261 isocyanato group Chemical group *N=C=O 0.000 description 28
238000002360 preparation method Methods 0.000 description 27
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 18
239000002253 acid Substances 0.000 description 18
238000006243 chemical reaction Methods 0.000 description 18
125000004435 hydrogen atom Chemical group [H]* 0.000 description 18
239000002904 solvent Substances 0.000 description 17
125000004432 carbon atom Chemical group C* 0.000 description 15
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 15
238000006748 scratching Methods 0.000 description 15
230000002393 scratching effect Effects 0.000 description 15
239000000758 substrate Substances 0.000 description 15
238000010186 staining Methods 0.000 description 14
239000007795 chemical reaction product Substances 0.000 description 13
238000000034 method Methods 0.000 description 13
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
229920001296 polysiloxane Polymers 0.000 description 12
239000000243 solution Substances 0.000 description 12
RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 11
239000007787 solid Substances 0.000 description 11
238000003860 storage Methods 0.000 description 11
239000008096 xylene Substances 0.000 description 11
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 10
GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 9
150000002430 hydrocarbons Chemical group 0.000 description 9
239000005056 polyisocyanate Substances 0.000 description 9
229920001228 polyisocyanate Polymers 0.000 description 9
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 9
229920002554 vinyl polymer Polymers 0.000 description 9
SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 8
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 8
150000002148 esters Chemical class 0.000 description 8
238000010438 heat treatment Methods 0.000 description 8
239000007983 Tris buffer Substances 0.000 description 7
150000007513 acids Chemical class 0.000 description 7
NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 7
238000007259 addition reaction Methods 0.000 description 7
238000004040 coloring Methods 0.000 description 7
125000005442 diisocyanate group Chemical group 0.000 description 7
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
229920000642 polymer Polymers 0.000 description 7
239000000126 substance Substances 0.000 description 7
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 7
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 6
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
229910008326 Si-Y Inorganic materials 0.000 description 6
229910006773 Si—Y Inorganic materials 0.000 description 6
QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 6
125000006364 carbonyl oxy methylene group Chemical group [H]C([H])([*:2])OC([*:1])=O 0.000 description 6
230000000694 effects Effects 0.000 description 6
229920000548 poly(silane) polymer Polymers 0.000 description 6
238000003756 stirring Methods 0.000 description 6
229910052726 zirconium Inorganic materials 0.000 description 6
CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 5
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 5
238000005336 cracking Methods 0.000 description 5
238000004132 cross linking Methods 0.000 description 5
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 5
238000005227 gel permeation chromatography Methods 0.000 description 5
239000011521 glass Substances 0.000 description 5
230000001771 impaired effect Effects 0.000 description 5
239000000463 material Substances 0.000 description 5
229920001225 polyester resin Polymers 0.000 description 5
239000004645 polyester resin Substances 0.000 description 5
238000012360 testing method Methods 0.000 description 5
239000010936 titanium Substances 0.000 description 5
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical group CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
239000004215 Carbon black (E152) Substances 0.000 description 4
101150065749 Churc1 gene Proteins 0.000 description 4
229920000877 Melamine resin Polymers 0.000 description 4
238000010521 absorption reaction Methods 0.000 description 4
238000000862 absorption spectrum Methods 0.000 description 4
125000003710 aryl alkyl group Chemical group 0.000 description 4
230000015572 biosynthetic process Effects 0.000 description 4
239000006227 byproduct Substances 0.000 description 4
230000008034 disappearance Effects 0.000 description 4
230000032050 esterification Effects 0.000 description 4
238000005886 esterification reaction Methods 0.000 description 4
RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 4
229930195733 hydrocarbon Natural products 0.000 description 4
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
238000011056 performance test Methods 0.000 description 4
229910052814 silicon oxide Inorganic materials 0.000 description 4
229920002050 silicone resin Polymers 0.000 description 4
150000003384 small molecules Chemical class 0.000 description 4
229910052719 titanium Inorganic materials 0.000 description 4
OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 4
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 4
239000002966 varnish Substances 0.000 description 4
YOBOXHGSEJBUPB-MTOQALJVSA-N (z)-4-hydroxypent-3-en-2-one;zirconium Chemical compound [Zr].C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O YOBOXHGSEJBUPB-MTOQALJVSA-N 0.000 description 3
GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 3
QUVMSYUGOKEMPX-UHFFFAOYSA-N 2-methylpropan-1-olate;titanium(4+) Chemical compound [Ti+4].CC(C)C[O-].CC(C)C[O-].CC(C)C[O-].CC(C)C[O-] QUVMSYUGOKEMPX-UHFFFAOYSA-N 0.000 description 3
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
239000005057 Hexamethylene diisocyanate Substances 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
239000005058 Isophorone diisocyanate Substances 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
102100038239 Protein Churchill Human genes 0.000 description 3
229910018557 Si O Inorganic materials 0.000 description 3
229910000831 Steel Inorganic materials 0.000 description 3
125000003118 aryl group Chemical group 0.000 description 3
BSDOQSMQCZQLDV-UHFFFAOYSA-N butan-1-olate;zirconium(4+) Chemical compound [Zr+4].CCCC[O-].CCCC[O-].CCCC[O-].CCCC[O-] BSDOQSMQCZQLDV-UHFFFAOYSA-N 0.000 description 3
238000006482 condensation reaction Methods 0.000 description 3
XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 3
229940093858 ethyl acetoacetate Drugs 0.000 description 3
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 3
FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 3
125000005395 methacrylic acid group Chemical class 0.000 description 3
239000003960 organic solvent Substances 0.000 description 3
150000007519 polyprotic acids Polymers 0.000 description 3
239000000843 powder Substances 0.000 description 3
XPGAWFIWCWKDDL-UHFFFAOYSA-N propan-1-olate;zirconium(4+) Chemical compound [Zr+4].CCC[O-].CCC[O-].CCC[O-].CCC[O-] XPGAWFIWCWKDDL-UHFFFAOYSA-N 0.000 description 3
BCWYYHBWCZYDNB-UHFFFAOYSA-N propan-2-ol;zirconium Chemical compound [Zr].CC(C)O.CC(C)O.CC(C)O.CC(C)O BCWYYHBWCZYDNB-UHFFFAOYSA-N 0.000 description 3
150000004756 silanes Chemical class 0.000 description 3
LIVNPJMFVYWSIS-UHFFFAOYSA-N silicon monoxide Inorganic materials [Si-]#[O+] LIVNPJMFVYWSIS-UHFFFAOYSA-N 0.000 description 3
239000010959 steel Substances 0.000 description 3
150000005846 sugar alcohols Polymers 0.000 description 3
235000010215 titanium dioxide Nutrition 0.000 description 3
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 3
FKTHNVSLHLHISI-UHFFFAOYSA-N 1,2-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC=C1CN=C=O FKTHNVSLHLHISI-UHFFFAOYSA-N 0.000 description 2
LZDKZFUFMNSQCJ-UHFFFAOYSA-N 1,2-diethoxyethane Chemical compound CCOCCOCC LZDKZFUFMNSQCJ-UHFFFAOYSA-N 0.000 description 2
RTTZISZSHSCFRH-UHFFFAOYSA-N 1,3-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC(CN=C=O)=C1 RTTZISZSHSCFRH-UHFFFAOYSA-N 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
UZKWTJUDCOPSNM-UHFFFAOYSA-N 1-ethenoxybutane Chemical compound CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 2
UUFQTNFCRMXOAE-UHFFFAOYSA-N 1-methylmethylene Chemical compound C[CH] UUFQTNFCRMXOAE-UHFFFAOYSA-N 0.000 description 2
FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
101100167062 Caenorhabditis elegans chch-3 gene Proteins 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
235000005956 Cosmos caudatus Nutrition 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
239000004640 Melamine resin Substances 0.000 description 2
BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 2
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-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
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
229910006360 Si—O—N Inorganic materials 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 2
QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 2
150000004720 acetoacetic acids Chemical class 0.000 description 2
YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 2
WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
239000005456 alcohol based solvent Substances 0.000 description 2
125000003342 alkenyl group Chemical group 0.000 description 2
125000003545 alkoxy group Chemical group 0.000 description 2
SMZOGRDCAXLAAR-UHFFFAOYSA-N aluminium isopropoxide Chemical compound [Al+3].CC(C)[O-].CC(C)[O-].CC(C)[O-] SMZOGRDCAXLAAR-UHFFFAOYSA-N 0.000 description 2
TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 2
CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 2
239000007859 condensation product Substances 0.000 description 2
238000007796 conventional method Methods 0.000 description 2
238000007334 copolymerization reaction Methods 0.000 description 2
SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 2
239000000539 dimer Substances 0.000 description 2
WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 description 2
SXWUUUJQQVXKKY-UHFFFAOYSA-N disilanyl-hydroxy-phenylsilane Chemical compound [SiH3][SiH2][SiH](O)C1=CC=CC=C1 SXWUUUJQQVXKKY-UHFFFAOYSA-N 0.000 description 2
239000006185 dispersion Substances 0.000 description 2
238000001035 drying Methods 0.000 description 2
239000000428 dust Substances 0.000 description 2
239000003759 ester based solvent Substances 0.000 description 2
FJKIXWOMBXYWOQ-UHFFFAOYSA-N ethenoxyethane Chemical compound CCOC=C FJKIXWOMBXYWOQ-UHFFFAOYSA-N 0.000 description 2
239000004210 ether based solvent Substances 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
125000000524 functional group Chemical group 0.000 description 2
FUZZWVXGSFPDMH-UHFFFAOYSA-M hexanoate Chemical compound CCCCCC([O-])=O FUZZWVXGSFPDMH-UHFFFAOYSA-M 0.000 description 2
230000007062 hydrolysis Effects 0.000 description 2
238000006460 hydrolysis reaction Methods 0.000 description 2
125000002768 hydroxyalkyl group Chemical group 0.000 description 2
239000001023 inorganic pigment Substances 0.000 description 2
QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
150000002576 ketones Chemical class 0.000 description 2
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
239000011976 maleic acid Substances 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
OSWPMRLSEDHDFF-UHFFFAOYSA-N methyl salicylate Chemical compound COC(=O)C1=CC=CC=C1O OSWPMRLSEDHDFF-UHFFFAOYSA-N 0.000 description 2
238000002156 mixing Methods 0.000 description 2
BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
239000012860 organic pigment Substances 0.000 description 2
NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 2
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MDDPTCUZZASZIQ-UHFFFAOYSA-N tris[(2-methylpropan-2-yl)oxy]alumane Chemical compound [Al+3].CC(C)(C)[O-].CC(C)(C)[O-].CC(C)(C)[O-] MDDPTCUZZASZIQ-UHFFFAOYSA-N 0.000 description 1
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125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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Landscapes

Paints Or Removers (AREA)

CA002122985A 1989-03-03 1990-03-02 Composition de resine, composition durcissable et composition de revetement Expired - Fee Related CA2122985C (fr)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
JP1052537A JP2787326B2 (ja)	1989-03-03	1989-03-03	硬化性組成物
JP52537/1989		1989-03-03
CA002011357A CA2011357C (fr)	1989-03-03	1990-03-02	Compose de resine, compose durcissable et compose de protection

Related Parent Applications (1)

Application Number	Title	Priority Date	Filing Date
CA002011357A Division CA2011357C (fr)	1989-03-03	1990-03-02	Compose de resine, compose durcissable et compose de protection

Publications (2)

Publication Number	Publication Date
CA2122985A1 CA2122985A1 (fr)	1990-09-04
CA2122985C true CA2122985C (fr)	1997-12-16

Family

ID=25673990

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA002122985A Expired - Fee Related CA2122985C (fr)	1989-03-03	1990-03-02	Composition de resine, composition durcissable et composition de revetement

Country Status (1)

Country	Link
CA (1)	CA2122985C (fr)

1990
- 1990-03-02 CA CA002122985A patent/CA2122985C/fr not_active Expired - Fee Related

Also Published As

Publication number	Publication date
CA2122985A1 (fr)	1990-09-04

Legal Events

Date	Code	Title	Description
1994-06-04	EEER	Examination request
2001-03-02	MKLA	Lapsed

Publication	Publication Date	Title
CA2011357C (fr)	1997-12-09	Compose de resine, compose durcissable et compose de protection
EP0358153B1 (fr)	1994-01-12	Composition de revêtement pour automobiles
CA2011358C (fr)	1997-12-23	Compose de resine de type a dispersion, compose durcissable et compose de protection
US5525673A (en)	1996-06-11	Hydroxyl and epoxy polymer, hydrolyzable silicone polymer, either containing flourine monomer
EP0687712A2 (fr)	1995-12-20	Composition de résines et procédé pour les durcir
US5498666A (en)	1996-03-12	Curable composition suitable as top coat
GB2234691A (en)	1991-02-13	Coating method
JPS6234910A (ja)	1987-02-14	シリコン含有付加共重合体
WO1994021737A1 (fr)	1994-09-29	Composition de resine a faible teneur en solvant, composition de revetement a faible teneur en solvant et procede de revetement utilisant ces compositions
CA2011356C (fr)	1997-11-11	Compose de resine de type a fluorine, compose durcissable et compose de protection
JP2948638B2 (ja)	1999-09-13	硬化性樹脂組成物
JPH02232251A (ja)	1990-09-14	樹脂組成物、硬化性組成物及び塗料組成物
CA2011801A1 (fr)	1990-09-15	Composition durcissable
JPH03277646A (ja)	1991-12-09	硬化性組成物およびそれを塗布してなる塗装物
EP1013730A1 (fr)	2000-06-28	Compositions durcissables pour des revêtements, des objets revêtus et des résines pour la préparation des-dits revêtements
JPWO1994021737A1 (ja)	1995-05-11	低溶剤型樹脂組成物，低溶剤型塗料組成物，及びその塗装方法
JPH02232250A (ja)	1990-09-14	樹脂組成物、硬化性組成物及び塗料組成物
CA2050034A1 (fr)	1992-03-01	Composition de resine polymerisable et methode de traitement
JP2721907B2 (ja)	1998-03-04	樹脂組成物、硬化性組成物及び塗料組成物
JPH0397734A (ja)	1991-04-23	ポリシロキサン系オリゴマー、ポリシロキサン系樹脂組成物及び硬化性樹脂組成物
JPH02251274A (ja)	1990-10-09	塗膜形成法
JPH023472A (ja)	1990-01-09	塗料組成物
JPH02228320A (ja)	1990-09-11	樹脂組成物、硬化性組成物及び塗料組成物
JPH02228350A (ja)	1990-09-11	樹脂組成物、硬化性組成物及び塗料組成物
JPH02251521A (ja)	1990-10-09	硬化性組成物