JP6460570B2 - ラジカル硬化性組成物 - Google Patents
ラジカル硬化性組成物 Download PDFInfo
- Publication number
- JP6460570B2 JP6460570B2 JP2014136927A JP2014136927A JP6460570B2 JP 6460570 B2 JP6460570 B2 JP 6460570B2 JP 2014136927 A JP2014136927 A JP 2014136927A JP 2014136927 A JP2014136927 A JP 2014136927A JP 6460570 B2 JP6460570 B2 JP 6460570B2
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- JP
- Japan
- Prior art keywords
- group
- naphthoquinone
- general formula
- hydroxy
- atom
- Prior art date
- 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.)
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- 239000000203 mixture Substances 0.000 title claims description 88
- 150000001875 compounds Chemical class 0.000 claims description 116
- -1 amine compound Chemical class 0.000 claims description 106
- 238000006116 polymerization reaction Methods 0.000 claims description 75
- 239000003112 inhibitor Substances 0.000 claims description 68
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 53
- 125000000217 alkyl group Chemical group 0.000 claims description 52
- 125000003118 aryl group Chemical group 0.000 claims description 49
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 48
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 42
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 42
- 125000003277 amino group Chemical group 0.000 claims description 36
- 125000005160 aryl oxy alkyl group Chemical group 0.000 claims description 36
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 claims description 35
- 125000003282 alkyl amino group Chemical group 0.000 claims description 34
- 239000003795 chemical substances by application Substances 0.000 claims description 26
- 229910052757 nitrogen Inorganic materials 0.000 claims description 21
- 125000002252 acyl group Chemical group 0.000 claims description 19
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 19
- 125000005843 halogen group Chemical group 0.000 claims description 17
- 229920006395 saturated elastomer Polymers 0.000 claims description 14
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 11
- 229910052799 carbon Inorganic materials 0.000 claims description 10
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 claims description 10
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 10
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- 125000005842 heteroatom Chemical group 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 125000004423 acyloxy group Chemical group 0.000 claims description 5
- 125000003368 amide group Chemical group 0.000 claims description 5
- 150000001869 cobalt compounds Chemical class 0.000 claims description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 5
- 238000002156 mixing Methods 0.000 claims description 5
- 125000004104 aryloxy group Chemical group 0.000 claims description 4
- 125000004429 atom Chemical group 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims 3
- 206010037660 Pyrexia Diseases 0.000 claims 1
- 230000001548 androgenic effect Effects 0.000 claims 1
- 239000000463 material Substances 0.000 claims 1
- 125000005429 oxyalkyl group Chemical group 0.000 claims 1
- 230000000379 polymerizing effect Effects 0.000 claims 1
- 150000003254 radicals Chemical class 0.000 description 109
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 71
- 238000000034 method Methods 0.000 description 21
- 238000003860 storage Methods 0.000 description 20
- 239000000178 monomer Substances 0.000 description 19
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 18
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 16
- 125000001424 substituent group Chemical group 0.000 description 16
- 238000001879 gelation Methods 0.000 description 13
- HDPLHDGYGLENEI-UHFFFAOYSA-N 2-[1-(oxiran-2-ylmethoxy)propan-2-yloxymethyl]oxirane Chemical compound C1OC1COC(C)COCC1CO1 HDPLHDGYGLENEI-UHFFFAOYSA-N 0.000 description 12
- 229920001567 vinyl ester resin Polymers 0.000 description 12
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 11
- 229910052760 oxygen Inorganic materials 0.000 description 11
- 239000001301 oxygen Substances 0.000 description 11
- 229920006305 unsaturated polyester Polymers 0.000 description 11
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 10
- 125000001624 naphthyl group Chemical group 0.000 description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 10
- 239000002994 raw material Substances 0.000 description 10
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 9
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 9
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 9
- 230000000694 effects Effects 0.000 description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 9
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 9
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 9
- 238000004519 manufacturing process Methods 0.000 description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 9
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 9
- FRASJONUBLZVQX-UHFFFAOYSA-N naphthoquinone group Chemical group C1(C=CC(C2=CC=CC=C12)=O)=O FRASJONUBLZVQX-UHFFFAOYSA-N 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 9
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 8
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 8
- 238000000465 moulding Methods 0.000 description 8
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 8
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 8
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 8
- 150000005846 sugar alcohols Polymers 0.000 description 8
- 125000000391 vinyl group Chemical class [H]C([*])=C([H])[H] 0.000 description 8
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 7
- 239000000835 fiber Substances 0.000 description 7
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 7
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 7
- 229920005862 polyol Polymers 0.000 description 7
- 150000003077 polyols Chemical class 0.000 description 7
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 6
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- 229920000728 polyester Polymers 0.000 description 6
- 229920001228 polyisocyanate Polymers 0.000 description 6
- 239000005056 polyisocyanate Substances 0.000 description 6
- 229920002554 vinyl polymer Polymers 0.000 description 6
- 125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 230000007613 environmental effect Effects 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- 239000000945 filler Substances 0.000 description 5
- 229940059574 pentaerithrityl Drugs 0.000 description 5
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 229910052717 sulfur Inorganic materials 0.000 description 5
- 239000011593 sulfur Substances 0.000 description 5
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
- 239000004412 Bulk moulding compound Substances 0.000 description 4
- 239000004593 Epoxy Substances 0.000 description 4
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
- MJVAVZPDRWSRRC-UHFFFAOYSA-N Menadione Chemical compound C1=CC=C2C(=O)C(C)=CC(=O)C2=C1 MJVAVZPDRWSRRC-UHFFFAOYSA-N 0.000 description 4
- 239000002202 Polyethylene glycol Substances 0.000 description 4
- 239000003677 Sheet moulding compound Substances 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 4
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical class C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 125000001309 chloro group Chemical group Cl* 0.000 description 4
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 4
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 description 4
- 229910052731 fluorine Inorganic materials 0.000 description 4
- 125000001153 fluoro group Chemical group F* 0.000 description 4
- 229910052740 iodine Inorganic materials 0.000 description 4
- CSFWPUWCSPOLJW-UHFFFAOYSA-N lawsone Chemical compound C1=CC=C2C(=O)C(O)=CC(=O)C2=C1 CSFWPUWCSPOLJW-UHFFFAOYSA-N 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 4
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 4
- 125000006606 n-butoxy group Chemical group 0.000 description 4
- 125000003506 n-propoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 4
- 229920001223 polyethylene glycol Polymers 0.000 description 4
- 229920001451 polypropylene glycol Polymers 0.000 description 4
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- CNHDIAIOKMXOLK-UHFFFAOYSA-N toluquinol Chemical compound CC1=CC(O)=CC=C1O CNHDIAIOKMXOLK-UHFFFAOYSA-N 0.000 description 4
- WYZRFRHDHZZWIH-UHFFFAOYSA-N 1,2,4-trimethoxynaphthalene Chemical compound C1=CC=CC2=C(OC)C(OC)=CC(OC)=C21 WYZRFRHDHZZWIH-UHFFFAOYSA-N 0.000 description 3
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 3
- CSGAUKGQUCHWDP-UHFFFAOYSA-N 1-hydroxy-2,2,6,6-tetramethylpiperidin-4-ol Chemical compound CC1(C)CC(O)CC(C)(C)N1O CSGAUKGQUCHWDP-UHFFFAOYSA-N 0.000 description 3
- KMEUSKGEUADGET-UHFFFAOYSA-N 1-hydroxy-2,2,6,6-tetramethylpiperidin-4-one Chemical compound CC1(C)CC(=O)CC(C)(C)N1O KMEUSKGEUADGET-UHFFFAOYSA-N 0.000 description 3
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical group C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
- BATAHUJPPGPXIN-UHFFFAOYSA-N 2-butoxynaphthalene-1,4-dione Chemical compound C1=CC=C2C(=O)C(OCCCC)=CC(=O)C2=C1 BATAHUJPPGPXIN-UHFFFAOYSA-N 0.000 description 3
- 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 3
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 3
- 239000004721 Polyphenylene oxide Substances 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 3
- 150000008064 anhydrides Chemical class 0.000 description 3
- 150000001735 carboxylic acids Chemical class 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- 125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 3
- 239000003365 glass fiber Substances 0.000 description 3
- 150000004820 halides Chemical class 0.000 description 3
- NWVVVBRKAWDGAB-UHFFFAOYSA-N hydroquinone methyl ether Natural products COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 3
- 230000006872 improvement Effects 0.000 description 3
- 150000004702 methyl esters Chemical class 0.000 description 3
- 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 3
- 125000004998 naphthylethyl group Chemical group C1(=CC=CC2=CC=CC=C12)CC* 0.000 description 3
- 125000004923 naphthylmethyl group Chemical group C1(=CC=CC2=CC=CC=C12)C* 0.000 description 3
- 125000004344 phenylpropyl group Chemical group 0.000 description 3
- 229920000570 polyether Polymers 0.000 description 3
- 239000001294 propane Substances 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- 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
- LJSLYKNKVQMIJY-UHFFFAOYSA-N 1,4-diethoxynaphthalene Chemical compound C1=CC=C2C(OCC)=CC=C(OCC)C2=C1 LJSLYKNKVQMIJY-UHFFFAOYSA-N 0.000 description 2
- ZVALGBPJYGUWIS-UHFFFAOYSA-N 1,4-dihydroanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1CC=CC2 ZVALGBPJYGUWIS-UHFFFAOYSA-N 0.000 description 2
- HUPXYLXDKXHZKU-UHFFFAOYSA-N 1,4-dimethoxynaphthalen-2-ol Chemical compound C1=CC=C2C(OC)=CC(O)=C(OC)C2=C1 HUPXYLXDKXHZKU-UHFFFAOYSA-N 0.000 description 2
- CQGDBBBZCJYDRY-UHFFFAOYSA-N 1-methoxyanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2OC CQGDBBBZCJYDRY-UHFFFAOYSA-N 0.000 description 2
- NQMUGNMMFTYOHK-UHFFFAOYSA-N 1-methoxynaphthalene Chemical compound C1=CC=C2C(OC)=CC=CC2=C1 NQMUGNMMFTYOHK-UHFFFAOYSA-N 0.000 description 2
- HAFSWNKUQBWUOF-UHFFFAOYSA-N 10-(2-methoxyethoxy)anthracen-9-ol Chemical compound OC=1C2=CC=CC=C2C(=C2C=CC=CC=12)OCCOC HAFSWNKUQBWUOF-UHFFFAOYSA-N 0.000 description 2
- JQLWTTWSQLIARL-UHFFFAOYSA-N 10-butoxyanthracen-9-ol Chemical compound OC=1C2=CC=CC=C2C(=C2C=CC=CC=12)OCCCC JQLWTTWSQLIARL-UHFFFAOYSA-N 0.000 description 2
- GURLVDBTIQCBSX-UHFFFAOYSA-N 10-ethoxyanthracen-9-ol Chemical compound OC=1C2=CC=CC=C2C(=C2C=CC=CC=12)OCC GURLVDBTIQCBSX-UHFFFAOYSA-N 0.000 description 2
- KFPVBOBUYDIZGD-UHFFFAOYSA-N 10-methoxy-1,2,3,4-tetrahydroanthracen-9-ol Chemical compound C1=CC=C2C(OC)=C(CCCC3)C3=C(O)C2=C1 KFPVBOBUYDIZGD-UHFFFAOYSA-N 0.000 description 2
- HEEPFNCXCOLFGE-UHFFFAOYSA-N 10-methoxyanthracen-9-ol Chemical compound C1=CC=C2C(OC)=C(C=CC=C3)C3=C(O)C2=C1 HEEPFNCXCOLFGE-UHFFFAOYSA-N 0.000 description 2
- VUZNLSBZRVZGIK-UHFFFAOYSA-N 2,2,6,6-Tetramethyl-1-piperidinol Chemical compound CC1(C)CCCC(C)(C)N1O VUZNLSBZRVZGIK-UHFFFAOYSA-N 0.000 description 2
- LWWOWQZGAGVVEU-UHFFFAOYSA-N 2,3,6-trimethylnaphthalene-1,4-dione Chemical compound CC1=CC=C2C(=O)C(C)=C(C)C(=O)C2=C1 LWWOWQZGAGVVEU-UHFFFAOYSA-N 0.000 description 2
- ZEGDFCCYTFPECB-UHFFFAOYSA-N 2,3-dimethoxynaphthalene-1,4-dione Chemical compound C1=CC=C2C(=O)C(OC)=C(OC)C(=O)C2=C1 ZEGDFCCYTFPECB-UHFFFAOYSA-N 0.000 description 2
- 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 2
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 2
- BAYPRHOLHCTNNC-UHFFFAOYSA-N 2-butylnaphthalene-1,4-dione Chemical compound C1=CC=C2C(=O)C(CCCC)=CC(=O)C2=C1 BAYPRHOLHCTNNC-UHFFFAOYSA-N 0.000 description 2
- LBXMBBATNWKPGI-UHFFFAOYSA-N 2-cyclohexylnaphthalene-1,4-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C=C1C1CCCCC1 LBXMBBATNWKPGI-UHFFFAOYSA-N 0.000 description 2
- QBHSRQVIJSKBPX-UHFFFAOYSA-N 2-ethylnaphthalene-1,4-dione Chemical compound C1=CC=C2C(=O)C(CC)=CC(=O)C2=C1 QBHSRQVIJSKBPX-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 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 2
- OBGBGHKYJAOXRR-UHFFFAOYSA-N 2-methoxy-1,4-naphthoquinone Chemical compound C1=CC=C2C(=O)C(OC)=CC(=O)C2=C1 OBGBGHKYJAOXRR-UHFFFAOYSA-N 0.000 description 2
- NJWGQARXZDRHCD-UHFFFAOYSA-N 2-methylanthraquinone Chemical compound C1=CC=C2C(=O)C3=CC(C)=CC=C3C(=O)C2=C1 NJWGQARXZDRHCD-UHFFFAOYSA-N 0.000 description 2
- VTWDKFNVVLAELH-UHFFFAOYSA-N 2-methylcyclohexa-2,5-diene-1,4-dione Chemical compound CC1=CC(=O)C=CC1=O VTWDKFNVVLAELH-UHFFFAOYSA-N 0.000 description 2
- GGFFBRRZAKLGFX-UHFFFAOYSA-N 2-methylsulfanylnaphthalene-1,4-dione Chemical compound C1=CC=C2C(=O)C(SC)=CC(=O)C2=C1 GGFFBRRZAKLGFX-UHFFFAOYSA-N 0.000 description 2
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- VVFNUTJHHYMHOA-UHFFFAOYSA-N 2-propylnaphthalene-1,4-dione Chemical compound C1=CC=C2C(=O)C(CCC)=CC(=O)C2=C1 VVFNUTJHHYMHOA-UHFFFAOYSA-N 0.000 description 2
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Landscapes
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Description
本発明のラジカル硬化性組成物に用いられるラジカル硬化性化合物(A)としては、分子中に1個以上の重合性基を有するものであれば特に限定されず、例えば、ラジカル硬化性オリゴマーやラジカル硬化性モノマーが挙げられる。これらのラジカル硬化性化合物は、2種類以上を用いてもよい。
本発明の重合禁止剤(C)は、N−オキシル化合物(C1)と縮合多環芳香族骨格を有する化合物(C2)、(C3)又は(C4)の混合物が用いられる。
本発明のラジカル硬化性組成物に用いられる促進剤(D)は低温での硬化性を向上させるためや、SMC(シートモールディングコンパウンド)、BMC(バルクモールディングコンパウンド)のようなラジカル硬化性組成物を半硬化の状態にするために用いる。このような促進剤としては、ナフテン酸コバルト、ナフテン酸マンガン、ナフテン酸銅、ナフテン酸カリウム、ナフテン酸カルシウム、オクチル酸コバルト、オクチル酸マンガン等の金属石鹸、コバルトアセチルアセトナート、バナジウムアセチルアセトナート等の金属キレート化合物、ジメチルアニリン、N,N’−ジメチルアニリン、N,N−ジメチルトルイジン、N,N−ジエチルアニリン、N,N−ジ(ヒドロキシ)−4−メチルアニリン等のアミン化合物、アセチルアセトン、アセト酢酸エチル等のアシル基含有ラクトン化合物、アセトアセトアミド化合物、β−ジケトン、β−ケトエステル、β−ケトアミド類等が挙げられ、いずれも溶剤を含んだ形態のものであってもよい。これらの促進剤は2種類以上を用いてもよい。これら例示した促進剤の中でもナフテン酸コバルト、オクチル酸コバルト等のコバルト系化合物及びアミン系化合物が好ましい。
本発明のラジカル硬化性組成物に用いられる硬化剤(B)としては、例えば、t−ブチルハイドロパーオキサイド、クメンハイドロパーオキサイド、ジイソプロピルベンゼンハイドロパーオキサイド、p−メンタンハイドロパーオキサイド、1,1,3,3−テトラメチルブチルハイドロパーオキサイド等のハイドロパーオキサイド、メチルエチルケトンパーオキサイド、アセチルアセトンパーオキサイド等のケトンパーオキサイド、ベンゾイルパーオキサイド等のジアシルパーオキサイド、ジクミルパーオキサイド、t−ブチルクミルパーオキサイド等のジアルキルパーオキサイド、1,1,3,3−テトラメチルブチルパーオキシ−2−エチルヘキサノエート、t−ブチルパーオキシ−2−エチルヘキサノエート、t−ブチルパーオキシベンゾエート等のアルキルパーエステル、ビス(4−t−ブチルシクロヘキシル)パーオキシジカーボネート等の過酸化物;2,2′−アゾビスイソブチロニトリル、2,2’−アゾビス−2−メチルブチロニトリル等のアゾ化合物等が挙げられる。これらの硬化剤は2種類以上を用いてもよい。
本発明のラジカル硬化性組成物において、性能を損なわない範囲内で、繊維補強剤、充填材、揺変性付与剤、揺変性付与助剤、カップリング剤、着色剤、紫外線吸収剤、酸価防止剤、増粘剤、減粘剤、内部離型剤、低収縮剤、消泡剤、ワックス、可塑剤、柄剤等の各種添加剤を適宜配合してもよい。
本発明のラジカル硬化性組成物は、その成分が異なる以外は公知のラジカル硬化性組成物と同様の製造方法で製造することができる。例えば、ラジカル硬化性化合物(A)、硬化剤(B)、重合禁止剤(C)、促進剤(D)を配合したのち、均一になるまで十分攪拌混合することにより製造することができる。硬化剤(B)を後で添加することも可能である。
以下のラジカル硬化性組成物のモデル液を調製し、試験に用いた。即ち、窒素ボックス中で20gのSMを100ccの試験管に入れ、表4に記載の重合禁止剤(C)をそれぞれ表中に記載の添加量加えた。次に窒素を20ml/分で通気しながら油浴にて110℃に加熱した。経時で粘度の変化を振動式粘度計で確認し、粘度の上昇が認められるまでの時間を表4に示した。なお、表中の重合禁止剤の添加量は、ラジカル硬化性化合物(A)100万重量部に対する重量部(ppm)である。
以下のラジカル硬化性組成物のモデル液を調製し、試験に用いた。即ち、窒素ボックス中にて表5の記載のようにSMとBMAを単独又は重量比1/1で混合したもの10gを30mlのサンプル管に入れ、表4に記載の重合禁止剤(C)と促進剤(D)をそれぞれ表中に記載の添加量加えた。次に窒素を20ml/分で3分間通気することで脱気した後に密栓し、酸素濃度を1%以下に制御した60℃のイナートオーブンに保管した。経時で粘度の変化をサンプル瓶を振ることで確認し、粘度の上昇が認められるまでの日数を表5に併せて示した。なお、表中の促進剤の添加量は、ラジカル硬化性化合物(A)100重量部に対する重量部(%)であり、重合禁止剤の添加量は、ラジカル硬化性化合物(A)100万重量部に対する重量部(ppm)である。
ラジカル硬化性化合物(A)としてビニルエステルを含む市販のラジカル硬化性組成物(日本ユピカ株式会社製 ネオポール8250L)100重量部と促進剤(D)として上記のナフテン酸コバルト・ミネラルスピリット溶液(6%)0.5重量部と、硬化剤(B)として市販のメチルエチルケトンパーオキサイド(日油株式会社製 パーメックN 「パーメック」は日油株式会社の登録商標)1.0重量部を用いて、JISK6901(2008)「液状不飽和ポリエステル樹脂試験方法」に記載の常温硬化特性(発熱法)による硬化特性試験を実施した。このような市販のビニルエステルには予め何らかの重合禁止剤が添加されているが、本試験では表6に記載の各重合禁止剤(C)をさらに加えて試験を実施し、ゲル化に要する時間、硬化に要する時間を測定し、結果を表6に併せて示した。なお、表中の重合禁止剤の添加量は、ラジカル硬化性化合物(A)100万重量部に対する重量部(ppm)である。
Claims (6)
- ラジカル硬化性化合物(A)、重合禁止剤(C)及び促進剤(D)を含有するラジカル硬化性組成物において、重合禁止剤(C)として、下記一般式(1-1)、一般式(1-2)又は一般式(1-3)で示されるN−オキシル化合物(C1)と一般式(2)で示される縮合多環芳香族骨格を有する化合物(C2)を用い、促進剤(D)として、コバルト系化合物又はアミン系化合物を用いることを特徴とするラジカル硬化性組成物。
(上記一般式(1-1)中、R1〜R4は水素原子、アルキル基、アリール基、アラルキル基、アルコキシアルキル基、アミノ基、アルキルアミノ基、グリシジル基、ヒドロキシアルキル基又はアリールオキシアルキル基を表し、それぞれ同一であっても、異なっていてもよい。X1及びY1は、同一であっても、異なっていてもよく、各々、水素原子、ヒドロキシル基、ハロゲン原子、アシル基、アルキル基、アリール基、アラルキル基、アルコキシアルキル基、アミノ基、アルキルアミノ基、グリシジル基、ヒドロキシアルキル基又はアリールオキシアルキル基のいずれかを表す。)
(上記一般式(1-2)中、R1〜R4は水素原子、アルキル基、アリール基、アラルキル基、アルコキシアルキル基、アミノ基、アルキルアミノ基、グリシジル基、ヒドロキシアルキル基又はアリールオキシアルキル基を表し、それぞれ同一であっても、異なっていてもよい。X3は、水素原子、酸素原子、ヒドロキシル基、アルキル基、ヒドロキシアルキル基、アルコキシ基、アシルオキシ基、アミノ基、アルキルアミノ基、アミド基のいずれかを表し、Aは、メチン基、窒素原子を表す。また、nは、0から2の整数であり、nが0の時は形成される環が5員環となる。但し、X3が酸素原子である時は、Aは炭素原子であり、X3とAの結合は二重結合となる。)
(上記一般式(1-3)中、R1〜R4は水素原子、アルキル基、アリール基、アラルキル基、アルコキシアルキル基、アミノ基、アルキルアミノ基、グリシジル基、ヒドロキシアルキル基又はアリールオキシアルキル基を表し、それぞれ同一であっても、異なっていてもよい。Aは、メチン基、窒素原子を表し、Bは、エステル結合、エーテル結合、アミド結合を表す。また、nは、0から2の整数であり、nが0の時は形成される環が5員環となる。)
(上記一般式(2)中、nは1から4の整数を表し、Rはアルキル基、アリール基、アラルキル基、アルコキシアルキル基、グリシジル基、ヒドロキシアルキル基又はアリールオキシアルキル基のいずれかを表し、OR基が複数ある場合のRは、それぞれ同一であっても、異なっていてもよい。X2、Y2及びZ2は、同一であっても、異なっていてもよく、各々、水素原子、ハロゲン原子、アシル基、アルキル基、アリール基、アラルキル基、アルコキシアルキル基、アミノ基、アルキルアミノ基、グリシジル基、ヒドロキシアルキル基又はアリールオキシアルキル基のいずれかを表し、このうち、X2及びY2は互いに結合して飽和又は不飽和の環を形成してもよく、ヘテロ原子を挟んで環を形成してもよい。)
- ラジカル硬化性化合物(A)、重合禁止剤(C)及び促進剤(D)を含有するラジカル硬化性組成物において、重合禁止剤(C)として、下記一般式(1-1)、一般式(1-2)又は一般式(1-3)で示されるN−オキシル化合物(C1)及び下記一般式(3)で示される縮合多環芳香族骨格を有する化合物(C3)を用い、促進剤(D)として、コバルト系化合物又はアミン系化合物を用いることを特徴とするラジカル硬化性組成物。
(上記一般式(1-1)中、R1〜R4は水素原子、アルキル基、アリール基、アラルキル基、アルコキシアルキル基、アミノ基、アルキルアミノ基、グリシジル基、ヒドロキシアルキル基又はアリールオキシアルキル基を表し、それぞれ同一であっても、異なっていてもよい。X1及びY1は、同一であっても、異なっていてもよく、各々、水素原子、ヒドロキシル基、ハロゲン原子、アシル基、アルキル基、アリール基、アラルキル基、アルコキシアルキル基、アミノ基、アルキルアミノ基、グリシジル基、ヒドロキシアルキル基又はアリールオキシアルキル基のいずれかを表す。)
(上記一般式(1-2)中、R1〜R4は水素原子、アルキル基、アリール基、アラルキル基、アルコキシアルキル基、アミノ基、アルキルアミノ基、グリシジル基、ヒドロキシアルキル基又はアリールオキシアルキル基を表し、それぞれ同一であっても、異なっていてもよい。X3は、水素原子、酸素原子、ヒドロキシル基、アルキル基、ヒドロキシアルキル基、アルコキシ基、アシルオキシ基、アミノ基、アルキルアミノ基、アミド基のいずれかを表し、Aは、メチン基、窒素原子を表す。また、nは、0から2の整数であり、nが0の時は形成される環が5員環となる。但し、X3が酸素原子である時は、Aは炭素原子であり、X3とAの結合は二重結合となる。)
(上記一般式(1-3)中、R1〜R4は水素原子、アルキル基、アリール基、アラルキル基、アルコキシアルキル基、アミノ基、アルキルアミノ基、グリシジル基、ヒドロキシアルキル基又はアリールオキシアルキル基を表し、それぞれ同一であっても、異なっていてもよい。Aは、メチン基、窒素原子を表し、Bは、エステル結合、エーテル結合、アミド結合を表す。また、nは、0から2の整数であり、nが0の時は形成される環が5員環となる。)
(上記一般式(3)中、R5、R6は、同一であっても、異なっていてもよく、アルキル基、アリール基、アラルキル基、アルコキシアルキル基、グリシジル基、ヒドロキシアルキル基又はアリールオキシアルキル基のいずれかを表し、X2、Y2及びZ2は、同一であっても、異なっていてもよく、各々、水素原子、ハロゲン原子、アシル基、アルキル基、アリール基、アラルキル基、アルコキシアルキル基、アミノ基、アルキルアミノ基、グリシジル基、ヒドロキシアルキル基又はアリールオキシアルキル基のいずれかを表し、このうち、X2及びY2は互いに結合して飽和又は不飽和の環を形成してもよく、ヘテロ原子を挟んで環を形成してもよい。)
- ラジカル硬化性化合物(A)、重合禁止剤(C)及び促進剤(D)を含有するラジカル硬化性組成物において、重合禁止剤(C)として、下記一般式(1-1)、一般式(1-2)又は一般式(1-3)で示されるN−オキシル化合物(C1)及び下記一般式(4)で示される縮合多環芳香族骨格を有する化合物(C4)を用い、促進剤(D)として、コバルト系化合物又はアミン系化合物を用いることを特徴とするラジカル硬化性組成物。
- ラジカル硬化性化合物(A)を100重量部とした場合において、促進剤(D)の添加量が0.05重量部以上、10重量部未満であることを特徴とする請求項1乃至3のいずれか一項に記載のラジカル硬化性組成物。
- ラジカル硬化性化合物(A)を100重量部とした場合において、さらに0.01重量部以上、10重量部未満の硬化剤(B)を混合することを特徴とする請求項1乃至請求項4のいずれか一項に記載のラジカル硬化性組成物。
- 請求項1乃至請求項5のいずれか一項に記載のラジカル硬化性組成物を活性エネルギー線及び/又は熱によりラジカル重合させることにより硬化させた硬化物。
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