JPH01254721A - ラジカル硬化型樹脂の硬化促進方法 - Google Patents

ラジカル硬化型樹脂の硬化促進方法

Info

Publication number: JPH01254721A
Authority: JP; Japan
Prior art keywords: curing; resin; curable resin; aromatic; acetoacetamide
Prior art date: 1988-04-01
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.): Granted

Application number

JP8147388A

Other languages

English (en)

Japanese (ja)

Other versions

JPH0588883B2 (2

Inventor

Eiichiro Takiyama

栄一郎滝山

Akira Yokoyama

横山　朗

Kiyoshi Ishihara

石原　清

Hiromitsu Abe

博光阿部

Yakichi Igarashi

五十嵐　彌吉

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.)

Nippon Nyukazai Co Ltd

Resonac Holdings Corp

Original Assignee

Nippon Nyukazai Co Ltd

Showa Highpolymer 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.)

1988-04-01

Filing date

1988-04-01

Publication date

1989-10-11

1988-04-01 Application filed by Nippon Nyukazai Co Ltd, Showa Highpolymer Co Ltd filed Critical Nippon Nyukazai Co Ltd

1988-04-01 Priority to JP8147388A priority Critical patent/JPH01254721A/ja

1989-10-11 Publication of JPH01254721A publication Critical patent/JPH01254721A/ja

1993-12-24 Publication of JPH0588883B2 publication Critical patent/JPH0588883B2/ja

Status Granted legal-status Critical Current

Links

229920005989 resin Polymers 0.000 title claims abstract description 31
239000011347 resin Substances 0.000 title claims abstract description 31
229920001567 vinyl ester resin Polymers 0.000 claims abstract description 11
GCPWJFKTWGFEHH-UHFFFAOYSA-N acetoacetamide Chemical compound CC(=O)CC(N)=O GCPWJFKTWGFEHH-UHFFFAOYSA-N 0.000 claims abstract description 10
125000003118 aryl group Chemical group 0.000 claims abstract description 8
229920006337 unsaturated polyester resin Polymers 0.000 claims abstract description 7
CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims abstract description 5
239000003822 epoxy resin Substances 0.000 claims abstract description 5
IQYZGBSHBFRNED-UHFFFAOYSA-N n-methyl-3-oxo-n-phenylbutanamide Chemical compound CC(=O)CC(=O)N(C)C1=CC=CC=C1 IQYZGBSHBFRNED-UHFFFAOYSA-N 0.000 claims abstract description 5
229920000647 polyepoxide Polymers 0.000 claims abstract description 5
HCFLZCNIGIOSHP-UHFFFAOYSA-N 2-[n-(3-oxobutanoyl)anilino]ethyl 3-oxobutanoate Chemical compound CC(=O)CC(=O)OCCN(C(=O)CC(C)=O)C1=CC=CC=C1 HCFLZCNIGIOSHP-UHFFFAOYSA-N 0.000 claims abstract 2
238000000034 method Methods 0.000 claims description 8
229910017052 cobalt Inorganic materials 0.000 abstract description 5
239000010941 cobalt Substances 0.000 abstract description 5
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 abstract description 5
238000004383 yellowing Methods 0.000 abstract description 4
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 abstract description 3
229910052802 copper Inorganic materials 0.000 abstract description 3
239000010949 copper Substances 0.000 abstract description 3
150000001451 organic peroxides Chemical class 0.000 abstract description 3
238000006243 chemical reaction Methods 0.000 abstract description 2
229910052720 vanadium Inorganic materials 0.000 abstract description 2
LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 abstract description 2
230000001737 promoting effect Effects 0.000 abstract 2
238000000576 coating method Methods 0.000 abstract 1
238000010526 radical polymerization reaction Methods 0.000 abstract 1
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 10
150000003254 radicals Chemical class 0.000 description 9
-1 organic acid salts Chemical class 0.000 description 8
WASQWSOJHCZDFK-UHFFFAOYSA-N diketene Chemical compound C=C1CC(=O)O1 WASQWSOJHCZDFK-UHFFFAOYSA-N 0.000 description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methylaniline Chemical compound CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 4
230000015572 biosynthetic process Effects 0.000 description 4
229910052757 nitrogen Inorganic materials 0.000 description 4
239000003973 paint Substances 0.000 description 4
238000003786 synthesis reaction Methods 0.000 description 4
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
125000000217 alkyl group Chemical group 0.000 description 3
238000005266 casting Methods 0.000 description 3
230000006866 deterioration Effects 0.000 description 3
230000000694 effects Effects 0.000 description 3
230000000704 physical effect Effects 0.000 description 3
229920000728 polyester Polymers 0.000 description 3
150000007519 polyprotic acids Polymers 0.000 description 3
229920006395 saturated elastomer Polymers 0.000 description 3
150000005846 sugar alcohols Polymers 0.000 description 3
NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 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
230000001133 acceleration Effects 0.000 description 2
YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 2
239000002253 acid Substances 0.000 description 2
229920000180 alkyd Polymers 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
125000004432 carbon atom Chemical group C* 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
229910001873 dinitrogen Inorganic materials 0.000 description 2
230000032050 esterification Effects 0.000 description 2
238000005886 esterification reaction Methods 0.000 description 2
UHESRSKEBRADOO-UHFFFAOYSA-N ethyl carbamate;prop-2-enoic acid Chemical compound OC(=O)C=C.CCOC(N)=O UHESRSKEBRADOO-UHFFFAOYSA-N 0.000 description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
229910052751 metal Inorganic materials 0.000 description 2
239000002184 metal Substances 0.000 description 2
239000000203 mixture Substances 0.000 description 2
239000000178 monomer Substances 0.000 description 2
GEMHFKXPOCTAIP-UHFFFAOYSA-N n,n-dimethyl-n'-phenylcarbamimidoyl chloride Chemical compound CN(C)C(Cl)=NC1=CC=CC=C1 GEMHFKXPOCTAIP-UHFFFAOYSA-N 0.000 description 2
125000004433 nitrogen atom Chemical group N* 0.000 description 2
150000003839 salts Chemical class 0.000 description 2
KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
WFUGQJXVXHBTEM-UHFFFAOYSA-N 2-hydroperoxy-2-(2-hydroperoxybutan-2-ylperoxy)butane Chemical compound CCC(C)(OO)OOC(C)(CC)OO WFUGQJXVXHBTEM-UHFFFAOYSA-N 0.000 description 1
HNNQYHFROJDYHQ-UHFFFAOYSA-N 3-(4-ethylcyclohexyl)propanoic acid 3-(3-ethylcyclopentyl)propanoic acid Chemical compound CCC1CCC(CCC(O)=O)C1.CCC1CCC(CCC(O)=O)CC1 HNNQYHFROJDYHQ-UHFFFAOYSA-N 0.000 description 1
OGIQUQKNJJTLSZ-UHFFFAOYSA-N 4-butylaniline Chemical compound CCCCC1=CC=C(N)C=C1 OGIQUQKNJJTLSZ-UHFFFAOYSA-N 0.000 description 1
OJGMBLNIHDZDGS-UHFFFAOYSA-N N-Ethylaniline Chemical compound CCNC1=CC=CC=C1 OJGMBLNIHDZDGS-UHFFFAOYSA-N 0.000 description 1
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
239000004721 Polyphenylene oxide Substances 0.000 description 1
ACIAHEMYLLBZOI-ZZXKWVIFSA-N Unsaturated alcohol Chemical compound CC\C(CO)=C/C ACIAHEMYLLBZOI-ZZXKWVIFSA-N 0.000 description 1
DYRDKSSFIWVSNM-UHFFFAOYSA-N acetoacetanilide Chemical compound CC(=O)CC(=O)NC1=CC=CC=C1 DYRDKSSFIWVSNM-UHFFFAOYSA-N 0.000 description 1
125000002339 acetoacetyl group Chemical group O=C([*])C([H])([H])C(=O)C([H])([H])[H] 0.000 description 1
150000008065 acid anhydrides Chemical class 0.000 description 1
125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
KXHPPCXNWTUNSB-UHFFFAOYSA-M benzyl(trimethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)(C)CC1=CC=CC=C1 KXHPPCXNWTUNSB-UHFFFAOYSA-M 0.000 description 1
150000001868 cobalt Chemical class 0.000 description 1
239000003086 colorant Substances 0.000 description 1
229940120693 copper naphthenate Drugs 0.000 description 1
SEVNKWFHTNVOLD-UHFFFAOYSA-L copper;3-(4-ethylcyclohexyl)propanoate;3-(3-ethylcyclopentyl)propanoate Chemical compound [Cu+2].CCC1CCC(CCC([O-])=O)C1.CCC1CCC(CCC([O-])=O)CC1 SEVNKWFHTNVOLD-UHFFFAOYSA-L 0.000 description 1
230000007797 corrosion Effects 0.000 description 1
238000005260 corrosion Methods 0.000 description 1
239000013078 crystal Substances 0.000 description 1
125000005442 diisocyanate group Chemical group 0.000 description 1
238000002845 discoloration Methods 0.000 description 1
239000000945 filler Substances 0.000 description 1
238000005194 fractionation Methods 0.000 description 1
239000007789 gas Substances 0.000 description 1
239000003365 glass fiber Substances 0.000 description 1
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 description 1
125000002768 hydroxyalkyl group Chemical group 0.000 description 1
FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
150000002739 metals Chemical class 0.000 description 1
239000006082 mold release agent Substances 0.000 description 1
GTWJETSWSUWSEJ-UHFFFAOYSA-N n-benzylaniline Chemical compound C=1C=CC=CC=1CNC1=CC=CC=C1 GTWJETSWSUWSEJ-UHFFFAOYSA-N 0.000 description 1
AKEYUWUEAXIBTF-UHFFFAOYSA-N n-methylnaphthalen-1-amine Chemical class C1=CC=C2C(NC)=CC=CC2=C1 AKEYUWUEAXIBTF-UHFFFAOYSA-N 0.000 description 1
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
229920003986 novolac Polymers 0.000 description 1
MLPVBIWIRCKMJV-UHFFFAOYSA-N o-aminoethylbenzene Natural products CCC1=CC=CC=C1N MLPVBIWIRCKMJV-UHFFFAOYSA-N 0.000 description 1
WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 1
150000002978 peroxides Chemical class 0.000 description 1
229920001225 polyester resin Polymers 0.000 description 1
239000004645 polyester resin Substances 0.000 description 1
229920000570 polyether Polymers 0.000 description 1
239000004848 polyfunctional curative Substances 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
239000002994 raw material Substances 0.000 description 1
238000010992 reflux Methods 0.000 description 1
239000002990 reinforced plastic Substances 0.000 description 1
230000002787 reinforcement Effects 0.000 description 1
239000012779 reinforcing material Substances 0.000 description 1
230000000630 rising effect Effects 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000004575 stone Substances 0.000 description 1
239000001384 succinic acid Substances 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

Landscapes

Macromonomer-Based Addition Polymer (AREA)
Processes Of Treating Macromolecular Substances (AREA)
Compositions Of Macromolecular Compounds (AREA)
Polymerization Catalysts (AREA)

JP8147388A 1988-04-01 1988-04-01 ラジカル硬化型樹脂の硬化促進方法 Granted JPH01254721A (ja)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
JP8147388A JPH01254721A (ja)	1988-04-01	1988-04-01	ラジカル硬化型樹脂の硬化促進方法

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP8147388A JPH01254721A (ja)	1988-04-01	1988-04-01	ラジカル硬化型樹脂の硬化促進方法

Publications (2)

Publication Number	Publication Date
JPH01254721A true JPH01254721A (ja)	1989-10-11
JPH0588883B2 JPH0588883B2 (2)	1993-12-24

Family

ID=13747371

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP8147388A Granted JPH01254721A (ja)	1988-04-01	1988-04-01	ラジカル硬化型樹脂の硬化促進方法

Country Status (1)

Country	Link
JP (1)	JPH01254721A (2)

1988
- 1988-04-01 JP JP8147388A patent/JPH01254721A/ja active Granted

Also Published As

Publication number	Publication date
JPH0588883B2 (2)	1993-12-24

Publication	Publication Date	Title
US4414367A (en)	1983-11-08	Curable molding compositions
EP0019740B1 (en)	1983-05-11	Compositions containing hydroxyneopentyl-hydroxypivalate-bis-halfesters and use of the compositions
JPH01254721A (ja)	1989-10-11	ラジカル硬化型樹脂の硬化促進方法
JPH01254722A (ja)	1989-10-11	ラジカル硬化型樹脂の硬化促進方法
JPS60110725A (ja)	1985-06-17	常温で硬化可能な組成物
JPH01254720A (ja)	1989-10-11	ラジカル硬化型樹脂の硬化促進方法
JPS60108430A (ja)	1985-06-13	常温で硬化可能な組成物
US4579890A (en)	1986-04-01	Curable molding compositions containing a polyester resin
JP2004156005A (ja)	2004-06-03	常温硬化可能な樹脂組成物、該樹脂組成物の硬化方法及び該樹脂組成物の硬化物
JPH01254723A (ja)	1989-10-11	ラジカル硬化型樹脂の硬化促進方法
JPH02191633A (ja)	1990-07-27	硬化促進作用を有する組成物
JPS5887109A (ja)	1983-05-24	樹脂組成物
JPH08151438A (ja)	1996-06-11	不飽和ポリエステル樹脂の製造方法
JP2004035703A (ja)	2004-02-05	貯蔵安定性に優れた人造大理石用ビニルエステル樹脂組成物
US5198529A (en)	1993-03-30	High molecular unsaturated polyester
JP2604069B2 (ja)	1997-04-23	高分子量不飽和ポリエステル樹脂の製造方法
JPS63305177A (ja)	1988-12-13	硬化性樹脂組成物
JPS5840569B2 (ja)	1983-09-06	ネツコウカセイジユシソセイブツノコウカホウホウ
JP2000239364A (ja)	2000-09-05	不飽和ポリエステル、その製造方法及び不飽和ポリエステル樹脂
JPH0491109A (ja)	1992-03-24	ビニルエステル系硬化樹脂の製造法及びそれに用いる硬化性組成物
JPH0212248B2 (2)	1990-03-19
JPS6031558A (ja)	1985-02-18	不飽和ポリエステル樹脂組成物
JPH0337214A (ja)	1991-02-18	低収縮性ラジカル重合性熱硬化樹脂組成物
JPS5978224A (ja)	1984-05-07	Ｆｒｐ成形用樹脂組成物
JP2527504B2 (ja)	1996-08-28	不飽和ポリエステルの製造方法