CN111868105B - 光聚合敏化剂组合物 - Google Patents
光聚合敏化剂组合物 Download PDFInfo
- Publication number
- CN111868105B CN111868105B CN201980020006.6A CN201980020006A CN111868105B CN 111868105 B CN111868105 B CN 111868105B CN 201980020006 A CN201980020006 A CN 201980020006A CN 111868105 B CN111868105 B CN 111868105B
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- CN
- China
- Prior art keywords
- furan
- alcohol
- amine
- sensitizer
- photopolymerizable
- Prior art date
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- 239000000203 mixture Substances 0.000 title claims abstract description 114
- 150000001875 compounds Chemical class 0.000 claims abstract description 101
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims abstract description 69
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 25
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 20
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 13
- -1 diethyl (2-cyanoethyl) amine Chemical class 0.000 claims description 97
- XPFVYQJUAUNWIW-UHFFFAOYSA-N furfuryl alcohol Chemical compound OCC1=CC=CO1 XPFVYQJUAUNWIW-UHFFFAOYSA-N 0.000 claims description 47
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 claims description 41
- 150000003254 radicals Chemical class 0.000 claims description 31
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 24
- 239000007870 radical polymerization initiator Substances 0.000 claims description 24
- 239000003963 antioxidant agent Substances 0.000 claims description 23
- 238000010526 radical polymerization reaction Methods 0.000 claims description 21
- 230000003078 antioxidant effect Effects 0.000 claims description 20
- 239000003999 initiator Substances 0.000 claims description 19
- VQKFNUFAXTZWDK-UHFFFAOYSA-N 2-Methylfuran Chemical compound CC1=CC=CO1 VQKFNUFAXTZWDK-UHFFFAOYSA-N 0.000 claims description 18
- SMNDYUVBFMFKNZ-UHFFFAOYSA-N 2-furoic acid Chemical compound OC(=O)C1=CC=CO1 SMNDYUVBFMFKNZ-UHFFFAOYSA-N 0.000 claims description 14
- 239000003505 polymerization initiator Substances 0.000 claims description 14
- 238000010538 cationic polymerization reaction Methods 0.000 claims description 13
- 150000001768 cations Chemical class 0.000 claims description 12
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 11
- PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 claims description 10
- DSSKLTAHHALFRW-UHFFFAOYSA-N N-cyclohexylpiperidine Chemical compound C1CCCCC1N1CCCCC1 DSSKLTAHHALFRW-UHFFFAOYSA-N 0.000 claims description 10
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 10
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical group CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 claims description 10
- NUCCVVARGOJARG-UHFFFAOYSA-N 2-(4-methylphenyl)furan Chemical compound C1=CC(C)=CC=C1C1=CC=CO1 NUCCVVARGOJARG-UHFFFAOYSA-N 0.000 claims description 7
- GANSPRKOWQQXPE-UHFFFAOYSA-N 2-(Methoxymethyl)furan Chemical compound COCC1=CC=CO1 GANSPRKOWQQXPE-UHFFFAOYSA-N 0.000 claims description 7
- QQBUHYQVKJQAOB-UHFFFAOYSA-N 2-ethenylfuran Chemical compound C=CC1=CC=CO1 QQBUHYQVKJQAOB-UHFFFAOYSA-N 0.000 claims description 7
- 239000002585 base Substances 0.000 claims description 6
- 230000001678 irradiating effect Effects 0.000 claims description 6
- NWHNXXMYEICZAT-UHFFFAOYSA-N 1,2,2,6,6-pentamethylpiperidin-4-ol Chemical compound CN1C(C)(C)CC(O)CC1(C)C NWHNXXMYEICZAT-UHFFFAOYSA-N 0.000 claims description 5
- VVOWZLWGURDTND-UHFFFAOYSA-N 1,3,4,5,6,7-hexakis-phenyl-2-benzofuran Chemical compound C1=CC=CC=C1C1=C2C(C=3C=CC=CC=3)=C(C=3C=CC=CC=3)C(C=3C=CC=CC=3)=C(C=3C=CC=CC=3)C2=C(C=2C=CC=CC=2)O1 VVOWZLWGURDTND-UHFFFAOYSA-N 0.000 claims description 5
- ZKSVYBRJSMBDMV-UHFFFAOYSA-N 1,3-diphenyl-2-benzofuran Chemical class C1=CC=CC=C1C1=C2C=CC=CC2=C(C=2C=CC=CC=2)O1 ZKSVYBRJSMBDMV-UHFFFAOYSA-N 0.000 claims description 5
- DGLIOWSKNOCHEX-UHFFFAOYSA-N 1-(furan-2-yl)-n-methylmethanamine Chemical compound CNCC1=CC=CO1 DGLIOWSKNOCHEX-UHFFFAOYSA-N 0.000 claims description 5
- AABTWRKUKUPMJG-UHFFFAOYSA-N 2,4-dimethylfuran Chemical compound CC1=COC(C)=C1 AABTWRKUKUPMJG-UHFFFAOYSA-N 0.000 claims description 5
- VUPDHIIPAKIKAB-UHFFFAOYSA-N 2,5-diphenylfuran Chemical compound C=1C=C(C=2C=CC=CC=2)OC=1C1=CC=CC=C1 VUPDHIIPAKIKAB-UHFFFAOYSA-N 0.000 claims description 5
- VKGLKWKQBWOENE-UHFFFAOYSA-N 2-(4-chlorophenyl)furan Chemical compound C1=CC(Cl)=CC=C1C1=CC=CO1 VKGLKWKQBWOENE-UHFFFAOYSA-N 0.000 claims description 5
- NDXFERKBHJWTMM-UHFFFAOYSA-N 2-(4-methoxyphenyl)furan Chemical compound C1=CC(OC)=CC=C1C1=CC=CO1 NDXFERKBHJWTMM-UHFFFAOYSA-N 0.000 claims description 5
- IEMMBWWQXVXBEU-UHFFFAOYSA-N 2-acetylfuran Chemical compound CC(=O)C1=CC=CO1 IEMMBWWQXVXBEU-UHFFFAOYSA-N 0.000 claims description 5
- UXGVMFHEKMGWMA-UHFFFAOYSA-N 2-benzofuran Chemical compound C1=CC=CC2=COC=C21 UXGVMFHEKMGWMA-UHFFFAOYSA-N 0.000 claims description 5
- BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical compound CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 claims description 5
- OXCGHDNCMSOEBZ-UHFFFAOYSA-N 2-methoxyfuran Chemical compound COC1=CC=CO1 OXCGHDNCMSOEBZ-UHFFFAOYSA-N 0.000 claims description 5
- GCXNJAXHHFZVIM-UHFFFAOYSA-N 2-phenylfuran Chemical compound C1=COC(C=2C=CC=CC=2)=C1 GCXNJAXHHFZVIM-UHFFFAOYSA-N 0.000 claims description 5
- DKCHIDPQVCTXIA-UHFFFAOYSA-N 3,4-diphenylfuran Chemical compound C=1OC=C(C=2C=CC=CC=2)C=1C1=CC=CC=C1 DKCHIDPQVCTXIA-UHFFFAOYSA-N 0.000 claims description 5
- SDKJDQLEFMMXET-UHFFFAOYSA-N 3-(4-bromophenyl)furan Chemical compound C1=CC(Br)=CC=C1C1=COC=C1 SDKJDQLEFMMXET-UHFFFAOYSA-N 0.000 claims description 5
- TZHXRUDIJAFUIY-UHFFFAOYSA-N 3-(4-fluorophenyl)furan Chemical compound C1=CC(F)=CC=C1C1=COC=C1 TZHXRUDIJAFUIY-UHFFFAOYSA-N 0.000 claims description 5
- HGSSTKBLPMJUDW-UHFFFAOYSA-N 3-(4-methoxyphenyl)furan Chemical compound C1=CC(OC)=CC=C1C1=COC=C1 HGSSTKBLPMJUDW-UHFFFAOYSA-N 0.000 claims description 5
- PCWCERNFIYTAIK-UHFFFAOYSA-N 3-(4-methylphenyl)furan Chemical compound C1=CC(C)=CC=C1C1=COC=C1 PCWCERNFIYTAIK-UHFFFAOYSA-N 0.000 claims description 5
- 125000006201 3-phenylpropyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 5
- LBASRTOKVSTSJC-UHFFFAOYSA-N 5,6-dimethyl-1,3-diphenyl-2-benzofuran Chemical compound C=12C=C(C)C(C)=CC2=C(C=2C=CC=CC=2)OC=1C1=CC=CC=C1 LBASRTOKVSTSJC-UHFFFAOYSA-N 0.000 claims description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 5
- DDRPCXLAQZKBJP-UHFFFAOYSA-N furfurylamine Chemical compound NCC1=CC=CO1 DDRPCXLAQZKBJP-UHFFFAOYSA-N 0.000 claims description 5
- PPXWSSUGLNOXLF-UHFFFAOYSA-N n,n-diethyl-2-methoxyethanamine Chemical compound CCN(CC)CCOC PPXWSSUGLNOXLF-UHFFFAOYSA-N 0.000 claims description 5
- SBYHFKPVCBCYGV-UHFFFAOYSA-N quinuclidine Chemical compound C1CC2CCN1CC2 SBYHFKPVCBCYGV-UHFFFAOYSA-N 0.000 claims description 5
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 claims description 5
- XHJGXOOOMKCJPP-UHFFFAOYSA-N 2-[tert-butyl(2-hydroxyethyl)amino]ethanol Chemical compound OCCN(C(C)(C)C)CCO XHJGXOOOMKCJPP-UHFFFAOYSA-N 0.000 claims description 4
- FWLFKBDHSBFSMW-UHFFFAOYSA-N 2,3,4,5-tetraphenylfuran Chemical compound C1=CC=CC=C1C1=C(C=2C=CC=CC=2)C(C=2C=CC=CC=2)=C(C=2C=CC=CC=2)O1 FWLFKBDHSBFSMW-UHFFFAOYSA-N 0.000 claims description 3
- 239000004065 semiconductor Substances 0.000 claims description 3
- 239000001003 triarylmethane dye Substances 0.000 claims description 3
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims 4
- YEQMNLGBLPBBNI-UHFFFAOYSA-N difurfuryl ether Chemical compound C=1C=COC=1COCC1=CC=CO1 YEQMNLGBLPBBNI-UHFFFAOYSA-N 0.000 claims 3
- XRDYDVNVKZSXRE-UHFFFAOYSA-N 1,3,4,7-tetraphenyl-2-benzofuran Chemical class C1=CC=CC=C1C1=C2C(C=3C=CC=CC=3)=CC=C(C=3C=CC=CC=3)C2=C(C=2C=CC=CC=2)O1 XRDYDVNVKZSXRE-UHFFFAOYSA-N 0.000 claims 2
- 230000000379 polymerizing effect Effects 0.000 abstract description 4
- 235000006708 antioxidants Nutrition 0.000 description 22
- 238000006116 polymerization reaction Methods 0.000 description 21
- 238000004040 coloring Methods 0.000 description 13
- KSMGAOMUPSQGTB-UHFFFAOYSA-N 9,10-dibutoxyanthracene Chemical compound C1=CC=C2C(OCCCC)=C(C=CC=C3)C3=C(OCCCC)C2=C1 KSMGAOMUPSQGTB-UHFFFAOYSA-N 0.000 description 11
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Natural products C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 11
- 238000000354 decomposition reaction Methods 0.000 description 10
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 9
- 239000004593 Epoxy Substances 0.000 description 8
- 229920000642 polymer Polymers 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 229910052717 sulfur Inorganic materials 0.000 description 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 7
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- 239000011248 coating agent Substances 0.000 description 6
- 238000000576 coating method Methods 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- VSAWBBYYMBQKIK-UHFFFAOYSA-N 4-[[3,5-bis[(3,5-ditert-butyl-4-hydroxyphenyl)methyl]-2,4,6-trimethylphenyl]methyl]-2,6-ditert-butylphenol Chemical compound CC1=C(CC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)C(C)=C(CC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)C(C)=C1CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 VSAWBBYYMBQKIK-UHFFFAOYSA-N 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- DAKWPKUUDNSNPN-UHFFFAOYSA-N Trimethylolpropane triacrylate Chemical compound C=CC(=O)OCC(CC)(COC(=O)C=C)COC(=O)C=C DAKWPKUUDNSNPN-UHFFFAOYSA-N 0.000 description 5
- 238000005259 measurement Methods 0.000 description 5
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- 229910052753 mercury Inorganic materials 0.000 description 5
- 239000003504 photosensitizing agent Substances 0.000 description 5
- 239000000049 pigment Substances 0.000 description 5
- 229920005989 resin Polymers 0.000 description 5
- 239000011347 resin Substances 0.000 description 5
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- BWSIKJKXQWLTLS-UHFFFAOYSA-N 1,2-dimethoxyanthracene Chemical compound C1=CC=CC2=CC3=C(OC)C(OC)=CC=C3C=C21 BWSIKJKXQWLTLS-UHFFFAOYSA-N 0.000 description 4
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 4
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Classifications
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- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F22/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides or nitriles thereof
- C08F22/10—Esters
- C08F22/1006—Esters of polyhydric alcohols or polyhydric phenols, e.g. ethylene glycol dimethacrylate
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/44—Polymerisation in the presence of compounding ingredients, e.g. plasticisers, dyestuffs, fillers
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
- C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
- C08F2/50—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
- C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
- C08F20/10—Esters
- C08F20/12—Esters of monohydric alcohols or phenols
- C08F20/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/68—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the catalysts used
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/17—Amines; Quaternary ammonium compounds
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K3/00—Materials not provided for elsewhere
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- G—PHYSICS
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- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
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- G—PHYSICS
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- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/0045—Photosensitive materials with organic non-macromolecular light-sensitive compounds not otherwise provided for, e.g. dissolution inhibitors
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
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- General Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Polymerisation Methods In General (AREA)
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Abstract
本发明的目的在于提供一种光聚合性组合物,其是对于包含波长为300nm至500nm波长范围的光具有活性的光聚合敏化剂,使包含该光聚合敏化剂的光聚合性组合物聚合得到的固化物的着色少。本发明涉及光聚合敏化剂组合物和含有该光聚合敏化剂组合物的光聚合性组合物,该光聚合敏化剂组合物的特征在于,其含有光聚合敏化剂和单重态氧猝灭剂,该光聚合敏化剂含有通式(1)所表示的烷氧基蒽化合物。通式(1)中,n表示1或2的整数,R表示碳原子数1~12的烷基,X表示氢原子或碳原子数1~8的烷基中的任一者。
Description
技术领域
本发明涉及光聚合敏化剂组合物,尤其是涉及含有烷氧基蒽化合物作为光聚合敏化剂的光聚合敏化剂组合物。
背景技术
光固化树脂目前被广泛用于涂布、油墨、电子材料等领域中。通过对光聚合性组合物照射例如紫外线、电子射线等光使其聚合、固化,由此可得到光固化树脂。该利用光进行固化的技术被用于例如木工用涂料、金属等的涂布材料、丝网印刷或胶版印刷用油墨、电子基板中使用的干膜抗蚀剂、以及全息图材料、密封剂、外涂层材料、光造型用树脂、粘接剂等各种用途中。
并且,该光聚合性组合物主要由光聚合性化合物、通过能量照射而引发光聚合性化合物的聚合的光聚合引发剂、以及多数情况下对光聚合引发剂进行活化的光聚合敏化剂构成。工业上多使用能够进行光阳离子聚合、光自由基聚合、或者将它们合用的光杂化聚合等的光聚合性组合物。
通常在仅利用光聚合引发剂时基于能量射线的聚合不充分的情况下、以及为了更高效地进行聚合时,使用在这些光聚合性组合物中使用的光聚合敏化剂。
在光聚合性组合物中包含色素、颜料、稳定剂等填充剂而使光聚合引发剂的吸收波长被屏蔽的情况下、光聚合引发剂的吸收波长与聚合中使用的能量射线(光线)的波长不匹配的情况下等,多使用光聚合敏化剂。特别是在光阳离子聚合中,光阳离子聚合引发剂的光吸收波长多数为365nm附近以下,例如在进行400nm左右的波长较长区域的光照射时,聚合不能充分进行。
另外,在自由基聚合引发剂中,即使是在不含磷原子或氮原子等的对环境友好的苄基甲基缩酮系、α-羟基烷基苯酮系自由基聚合引发剂的情况下,由于其吸收波长的关系,也主要使用高压水银灯作为光的照射源,具有不能利用包含更长波长的光的金属卤化物灯或镓掺杂灯充分进行聚合的问题。
这种情况下,通过使用在较长波长侧(这种情况下为400nm附近)具有光吸收的光聚合敏化剂,能够有效地进行聚合。作为这样的光聚合敏化剂,例如已知有二烷氧基蒽类、噻吨酮类等(专利文献1~4等)。另一方面,这些在400nm附近具有光吸收的光聚合敏化剂尽管显示出上述敏化效果,但往往观察到使固化物着色的现象,因此有时也难以用于特别是光学用途、显示屏用材料等中。作为能够降低这样的着色的光聚合敏化剂,例如提出了二酰基蒽类(专利文献5、6)、二酰氧基蒽类(专利文献7)等,但它们也存在有时灵敏度稍劣于二烷氧基蒽类的问题。
另一方面,本发明与烷氧基蒽化合物一起使用单重态氧猝灭剂,已知有使用二甲氧基蒽作为单重态氧猝灭剂的示例。例如,为了防止因电子照相感光体表面的活性氧(单重态氧)所致的劣化而添加活性氧猝灭剂(单重态氧猝灭剂)时,作为该单重态氧猝灭剂使用了镍络合物等,但二甲氧基蒽、9,10-双(4-甲氧基苯基)蒽、9,10-二苯基蒽等也可作为单重态氧猝灭剂使用(专利文献8)。另外,为了防止彩色滤光片的着色组合物的退色,使用了抗氧化剂或单重态氧猝灭剂,作为该单重态氧猝灭剂的一例,可以举出二甲氧基蒽、9,10-双(4-甲氧基苯基)蒽、9,10-二苯基蒽等(专利文献9)。
另外,在专利文献10中,在将着色固化性树脂组合物固化而成的彩色滤光片的合成中,为了提高着色固化组合物的稳定性,可以包含抗氧化剂,作为该抗氧化剂,可以举出例如自由基捕捉剂、过氧化物分解剂、紫外线吸收剂、单重态氧猝灭剂等。并且,作为该单重态氧猝灭剂的示例,可以一律并列地举出四甲基乙烯、环戊烯等烯键式化合物、二乙胺、三乙胺、1,4-二氮杂二环辛烷(DABCO)、N-乙基咪唑等胺类、具有或不具有取代基的萘、二甲基萘、二甲氧基蒽、蒽、二苯基蒽等稠合多环芳香族化合物;1,3-二苯基异苯并呋喃、1,2,3,4-四苯基-1,3-环戊二烯、五苯基环戊二烯等芳香族化合物。另外,该文献中记载了,本发明的着色固化性组合物可以进一步根据需要含有填充材料、紫外线吸收剂、防凝集剂、光敏剂、光稳定剂等各种添加剂,作为该光敏剂的示例,具体地说,并列罗列出了芘、苝、吖啶、噻吨酮、2-氯噻吨酮、苯并黄素、N-乙烯基咔唑、9,10-二丁氧基蒽、蒽醌、二苯甲酮、香豆素、香豆素酮、菲、樟脑醌、吩噻嗪衍生物等,其中还举出了9,10-二丁氧基蒽。但是,单重态氧猝灭剂和光敏剂均不过是可以根据需要添加的化合物,并未记载添加两者的具体例。另外,实施例中并未记载既添加单重态氧猝灭剂也添加光敏剂的示例。进而也没有关于光敏剂的着色问题的记载,也并未记载单重态氧猝灭剂对于抑制该着色是必要的内容。作为为了使作为彩色滤光片用着色剂的三芳基甲烷染料具有色彩特性的稳定性而使用的抗氧化剂的一种,可以使用单重态氧猝灭剂。另外,例如如专利文献11中所见,同样在使用有机色素等的情况下,为了防止其退色,具有使用单重态氧猝灭剂的示例。
现有技术文献
专利文献
专利文献1:日本特开平06-059380号公报
专利文献2:日本特开平11-279212号公报
专利文献3:日本特开平11-140110号公报
专利文献4:日本特开2001-106648号公报
专利文献5:日本特开2007-99637号公报
专利文献6:日本特开2007-204438号公报
专利文献7:日本特开2014-101442号公报
专利文献8:日本特开2006-234943号公报
专利文献9:日本特开2012-155243号公报
专利文献10:日本特开2016-40593号公报
专利文献11:日本特开2011-99047号公报
发明内容
发明所要解决的课题
作为光聚合敏化剂使用的烷氧基蒽化合物是利用长波长区域的光进行固化的情况下非常具有活性的光聚合敏化剂。即,通过所照射的光进行激发,该激发能量能够有效地传递至光聚合引发剂。但是,本发明人对蒽化合物的反应性进行了深入研究,结果发现,该激发状态的烷氧基蒽化合物还同时激发在体系内微量存在的氧分子,生成单重态氧。并且发现该生成的单重态氧与该烷氧基蒽化合物发生反应。即,发现了作为光聚合敏化剂使用的烷氧基蒽化合物发生着色的原因如下:该烷氧基蒽化合物通过光照射而被激发,该激发种将基态的氧转换成单重态氧,该单重态氧与烷氧基蒽化合物发生反应,由此经内过氧化物中间体而分解成着色物,作为防止该着色的策略,发现通过使单重态氧猝灭剂与烷氧基蒽化合物共存,可妨碍单重态氧与烷氧基蒽化合物发生反应,由此能够防止该烷氧基蒽化合物的分解着色,从而完成了本发明。即,本发明的目的在于提供一种光聚合性组合物,其是对于包含波长为300nm至500nm波长范围的光具有活性的光聚合敏化剂组合物,使包含该光聚合敏化剂组合物的光聚合性组合物聚合得到的固化物的着色少。
该基于单重态氧的烷氧基蒽化合物的分解反应并非光聚合敏化剂中通常产生的现象,而是使用烷氧基蒽化合物作为光聚合敏化剂时的特有现象。例如在噻吨酮、香豆素酮、二苯甲酮等中未观测到该现象。在光聚合敏化剂的情况下,需要吸收某一特定波长的紫外线来进行激发,通过将该激发能量传递至光聚合引发剂,引发剂发生分解、引发聚合。但是,一部分光聚合敏化剂会发生下述反应,通过该激发能量,激发基态的氧而生成单重态氧。例如噻吨酮、烷氧基蒽化合物具有该能力。但是,已知在烷氧基蒽化合物的情况下,其与自身生成的单重态氧发生反应,经内过氧化物中间体而分解成着色物。噻吨酮不会发生这样的反应。
用于解决课题的手段
为了实现上述目的,第1要点在于一种光聚合敏化剂组合物,其特征在于,其含有光聚合敏化剂和单重态氧猝灭剂,该光聚合敏化剂含有通式(1)所表示的烷氧基蒽化合物。
[化1]
通式(1)中,n表示1或2的整数,R表示碳原子数1~12的烷基,X表示氢原子或碳原子数1~8的烷基中的任一者。
第2要点在于一种光聚合敏化剂组合物,其特征在于,其含有自由基聚合敏化剂和单重态氧猝灭剂,该自由基聚合敏化剂含有通式(2)所表示的烷氧基蒽化合物。
[化2]
通式(2)中,R表示碳原子数1~12的烷基,X表示氢原子或碳原子数1~8的烷基中的任一者。
第3要点在于一种光聚合敏化剂组合物,其特征在于,其含有自由基聚合敏化剂和单重态氧猝灭剂,该自由基聚合敏化剂含有通式(3)所表示的烷氧基蒽化合物。
[化3]
通式(3)中,R表示碳原子数1~12的烷基,X表示氢原子或碳原子数1~8的烷基中的任一者。
第4要点在于第1要点~第3要点中任一要点所述的光聚合敏化剂组合物,其特征在于,在含有单重态氧猝灭剂的同时进一步含有抗氧化剂。
第5要点在于第1要点~第4要点中任一要点所述的光聚合敏化剂组合物,其特征在于,单重态氧猝灭剂为叔胺。
第6要点在于一种光聚合性组合物,其特征在于,其含有第1要点~第5要点中任一要点所述的光聚合敏化剂组合物、光聚合引发剂和聚合性化合物。
第7要点在于第6要点所述的光聚合性组合物,其特征在于,在光聚合性组合物中不含有三芳基甲烷染料。
第8要点在于第6要点或第7要点所述的光聚合性组合物,其中,聚合性化合物为自由基聚合性化合物,光聚合引发剂为光自由基聚合引发剂。
第9要点在于第6要点或第7要点所述的光聚合性组合物,其中,聚合性化合物为阳离子聚合性化合物,光聚合引发剂为光阳离子聚合引发剂。
第10要点在于第6要点或第7要点所述的光聚合性组合物,其中,聚合性化合物含有自由基聚合性化合物和阳离子聚合性化合物这两者,光聚合引发剂含有光自由基聚合引发剂和光阳离子聚合引发剂这两者。
第11要点在于一种光聚合方法,其中,通过对第6要点~第10要点中任一要点所述的光聚合性组合物照射包含波长为300nm至500nm波长范围的光的光而使其聚合。
第12要点在于第11要点所述的光聚合方法,其特征在于,包含波长为300nm至500nm波长范围的光的光的照射源是中心波长为365nm、375nm、385nm、395nm、405nm的紫外LED或405nm的半导体激光器。
发明效果
本发明的含有光聚合敏化剂(其含有通式(1)所表示的烷氧基蒽化合物)和单重态氧猝灭剂的光聚合敏化剂组合物作为感应包含波长为300nm至500nm波长范围的光而将自由基聚合引发剂活化的自由基聚合敏化剂组合物是有用的,此外,本发明的光聚合敏化剂组合物能够抑制因光照射所致的来自通式(1)所表示的烷氧基蒽化合物的着色分解物的生成,并且能够抑制使包含该光聚合敏化剂组合物的光聚合性组合物聚合而得到的固化物的着色。
通过下述的详细说明进一步明确本发明的目的、特征和优点。
具体实施方式
下面详细叙述本发明。
(烷氧基蒽化合物)
本发明涉及下述通式(1)所表示的烷氧基蒽化合物。
[化4]
通式(1)中,n表示1或2的整数,R表示碳原子数1~12的烷基,X表示氢原子或碳原子数1~8的烷基中的任一者。
通式(1)中,n=2的情况下,成为下述通式(2)所表示的9,10-二烷氧基蒽化合物。
[化5]
通式(2)中,R表示碳原子数1~12的烷基,X表示氢原子或碳原子数1~8的烷基中的任一者。
此外,通式(1)中,n=1的情况下,成为下述通式(3)所表示的9-烷氧基蒽化合物。
[化6]
通式(3)中,R表示碳原子数1~12的烷基,X表示氢原子或碳原子数1~8的烷基中的任一者。
通式(1)~通式(3)中,作为R所表示的烷基,可以举出甲基、乙基、正丙基、异丙基、正丁基、异丁基、戊基、己基、庚基、辛基、2-乙基己基、壬基、癸基或十二烷基等。
作为X所表示的烷基,可以为直链、也可以为支链,可以举出甲基、乙基、丙基、丁基、戊基、己基、2-乙基己基等。
作为通式(1)~通式(3)所表示的化合物的具体例,例如可以举出下述化合物。作为n=2、X为氢原子的化合物,可以举出9,10-二甲氧基蒽、9,10-二乙氧基蒽、9,10-二丙氧基蒽、9,10-二丁氧基蒽、9,10-双(正戊氧基)蒽、9,10-双(异戊氧基氧基)蒽(9,10-ビス(i-ペンチルオキシオキシ)アントラセン)、9,10-双(正己氧基)蒽、9,10-双(正庚氧基)蒽、9,10-双(正辛氧基)蒽、9,10-双(2-乙基己氧基)蒽等。
作为n=1、X为氢原子的化合物,可以举出9-甲氧基蒽、9-乙氧基蒽、9-丙氧基蒽、9-丁氧基蒽、9-(正戊氧基)蒽、9-(异戊氧基氧基)蒽、9-(正己氧基)蒽、9-(正庚氧基)蒽、9-(正辛氧基)蒽、9-(2-乙基己氧基)蒽等。
作为n=2、X为烷基的情况的具体例,可以举出2-甲基-9,10-二甲氧基蒽、2-甲基-9,10-二乙氧基蒽、2-甲基-9,10-二丙氧基蒽、2-甲基-9,10-二丁氧基蒽、2-甲基-9,10-双(正戊氧基)蒽、2-甲基-9,10-双(异戊氧基氧基)蒽、2-甲基-9,10-双(正己氧基)蒽、2-甲基-9,10-双(正庚氧基)蒽、2-甲基-9,10-双(正辛氧基)蒽、2-甲基-9,10-双(2-乙基己氧基)蒽、2-乙基-9,10-二甲氧基蒽、2-乙基-9,10-二乙氧基蒽、2-乙基-9,10-二丙氧基蒽、2-乙基-9,10-二丁氧基蒽、2-乙基-9,10-双(正戊氧基)蒽、2-乙基-9,10-双(异戊氧基氧基)蒽、2-乙基-9,10-双(正己氧基)蒽、2-乙基-9,10-双(正庚氧基)蒽、2-乙基-9,10-双(正辛氧基)蒽、2-乙基-9,10-双(2-乙基己氧基)蒽等。
作为n=1、X为烷基的情况的具体例,可以举出2-甲基-9-甲氧基蒽、2-甲基-9-乙氧基蒽、2-甲基-9-丙氧基蒽、2-甲基-9-丁氧基蒽、2-甲基-9-(正戊氧基)蒽、2-甲基-9-(异戊氧基氧基)蒽、2-甲基-9-(正己氧基)蒽、2-甲基-9-(正庚氧基)蒽、2-甲基-9-(正辛氧基)蒽、2-甲基-9-(2-乙基己氧基)蒽、2-乙基-9-甲氧基蒽、2-乙基-9-乙氧基蒽、2-乙基-9-丙氧基蒽、2-乙基-9-丁氧基蒽、2-乙基-9-(正戊氧基)蒽、2-乙基-9-(异戊氧基氧基)蒽、2-乙基-9-(正己氧基)蒽、2-乙基-9-(正庚氧基)蒽、2-乙基-9-(正辛氧基)蒽、2-乙基-9-(2-乙基己氧基)蒽等。
通式(1)所表示的烷氧基蒽化合物中,在X所表示的取代基为卤原子的情况下,也能够作为自由基聚合敏化剂使用。作为这种情况的卤原子,可以举出氟原子、氯原子、溴原子或碘原子等。
作为n=2、X为卤原子的情况的具体例,可以举出2-氯-9,10-二甲氧基蒽、2-氯-9,10-二乙氧基蒽、2-氯-9,10-二丙氧基蒽、2-氯-9,10-二丁氧基蒽、2-氯-9,10-双(正戊氧基)蒽、2-氯-9,10-双(异戊氧基氧基)蒽、2-氯-9,10-双(正己氧基)蒽、2-氯-9,10-双(正庚氧基)蒽、2-氯-9,10-双(正辛氧基)蒽、2-氯-9,10-双(2-乙基己氧基)蒽、2-溴-9,10-二甲氧基蒽、2-溴-9,10-二乙氧基蒽、2-溴-9,10-二丙氧基蒽、2-溴-9,10-二丁氧基蒽、2-溴-9,10-双(正戊氧基)蒽、2-溴-9,10-双(异戊氧基氧基)蒽、2-溴-9,10-双(正己氧基)蒽、2-溴-9,10-双(正庚氧基)蒽、2-溴-9,10-双(正辛氧基)蒽、2-溴-9,10-双(2-乙基己氧基)蒽等。
作为n=1、X为卤原子的情况的具体例,可以举出2-氯-9-甲氧基蒽、2-氯-9-乙氧基蒽、2-氯-9-丙氧基蒽、2-氯-9-丁氧基蒽、2-氯-9-(正戊氧基)蒽、2-氯-9-(异戊氧基氧基)蒽、2-氯-9-(正己氧基)蒽、2-氯-9-(正庚氧基)蒽、2-氯-9-(正辛氧基)蒽、2-氯-9-(2-乙基己氧基)蒽、2-溴-9-甲氧基蒽、2-溴-9-乙氧基蒽、2-溴-9-丙氧基蒽、2-溴-9-丁氧基蒽、2-溴-9-(正戊氧基)蒽、2-乙基-9-(异戊氧基氧基)蒽、2-溴-9-(正己氧基)蒽、2-溴-9-(正庚氧基)蒽、2-溴-9-(正辛氧基)蒽、2-溴-9-(2-乙基己氧基)蒽等。
这些例示的化合物中,从制造的容易性和性能的高度的方面出发,特别优选X为氢原子、n为2、R为碳原子数2~8的化合物,特别优选9,10-二乙氧基蒽、9,10-二丙氧基蒽、9,10-二丁氧基蒽。
(单重态氧猝灭剂)
作为本发明的单重态氧猝灭剂,是可通过来自单重态状态的氧的能量移动而使单重态氧失活的化合物,例如可以举出顺式-1,2-二乙氧基乙烯、2-甲基-2-戊烯、反式-3-甲基-2-戊烯、3,5-二氧杂环戊烯、1-甲基环戊烯、1,2-二甲基环己烯、环戊二烯、1,3-环己二烯、α-萜品烯、全反式视黄醇、八叠球菌六氢番茄红素(サルシナフトフルエン)、C-30胡萝卜素类、C-35胡萝卜素类、β-阿朴-8’-胡萝卜素醛、叶黄素、异玉米黄素、β-胡萝卜素、角黄素、番茄红素等不饱和烃;丁胺、苄基胺等伯胺类;二乙胺、二丙胺、二异丙胺、四氢吡咯、哌啶、2,6-二甲基哌啶、二(2-羟基乙基)甲基胺、N,N-二甲基异丁烯基胺等仲胺类;三甲胺、三乙胺、二乙基(2-羟基乙基)胺、二乙基(2-甲氧基乙基)胺、二乙基(2-氰基乙基)胺、二乙基(7-氨基庚基)胺、三丁胺、二(2-羟基乙基)-叔丁胺、碱、1-甲基哌啶、4-羟基-1,2,2,6,6-五甲基哌啶、1-环己基哌啶、奎宁环、哌嗪、1,4-二氮杂双环[2.2.2]辛烷等叔胺类;苯胺、2-氨基萘、N-甲基苯胺、二苯基苯胺、4,4’-叔辛基二苯基胺、N,N-二甲基苯胺、间氯-N,N-二甲基苯胺、对溴-N,N-二甲基苯胺、对甲基-N,N-二甲基苯胺、对氰基-N,N-二甲基苯胺、对(N,N-二甲氨基)苯甲醛、间甲氧基-N,N-二甲基苯胺、对甲氧基-N,N-二甲基苯胺、邻苯二胺、4,4’-二氨基联苯、1-异丙基氨基-4-苯基氨基苯、1-环己基氨基-4-苯基氨基苯、1-环己基氨基-4-苯基氨基苯盐酸盐、N,N’,N”,N”’-四甲基苯二胺、鲁米诺等芳香族胺类;呋喃、2-甲基呋喃、糠基胺、2-甲氧基呋喃、糠醇、糠基甲醚、2-呋喃甲酸、2-乙烯基呋喃、α-甲基糠醇、α-苄基糠醇、α-苯基乙基糠醇、α-(3-苯基丙基)糠醇、α-二苯甲基糠醇、α,α-二苯基糠醇、2-乙酰基呋喃、N-甲基糠基胺、2-苯基呋喃、3-苯基呋喃、3-(4’-氟苯基)呋喃、2-(4’-氯苯基)呋喃、3-(4’-溴苯基)呋喃、2-(4’-甲基苯基)呋喃、3-(4’-甲基苯基)呋喃、2-(4’-甲氧基苯基)呋喃、3-(4’-甲氧基苯基)呋喃、2,4-二甲基呋喃、2,5-二甲基呋喃、2,5-二苯基呋喃、3,4-二苯基呋喃、2,3,4,5,-四苯基呋喃、2,2(2,5)二氧三环十四碳四烯(Furanophane)、异苯并呋喃、1,3-二苯基异苯并呋喃、1,3-二苯基-5,6-二甲基异苯并呋喃、1,3,4,7-四苯基异苯并呋喃、1,3,4,5,6,7-六苯基异苯并呋喃等呋喃化合物;萘、二甲基萘、二甲氧基蒽、蒽、二苯基蒽、菲、芘、苝、蒄、并四苯、并五苯、红荧烯、3,4-苯并荧蒽(3,4-べンゾフルオランスしン)、2,3-苯并芴、1,12-苯并苝、3,4-苯并芘、4,5-苯并芘、9,10-双(4-甲氧基苯基)蒽、9,10-二苯基蒽、1-氯-9,10-二苯基蒽、9-苯基蒽、4,5-亚甲基菲、十环烯、1,2,3,4-二苯并蒽、1,2,5,6-二苯并蒽、二茚并苝(ヘ°リフランスしン)、4,7-二苯基-1,10-二氮菲、荧蒽、3-甲基胆蒽、三亚苯、苯并[ghi]苝、4H-环五[def]菲以及它们的C1~C20烷基取代体、烷氧基取代体等稠合多环芳香族化合物;以及Harry H.wasserman,"Singlet Oxygen(单重态氧)",第5章,Academic Press(1979)、Nicholas J.Turro,"ModernMolecular Photochemistry",第14章,The Benjamin/Cummings Publishing Co.,Inc.(1978)和CMC公司发行彩色照片感光材料用高功能化学(カラー写真感光材料用高機能ケミカルス),第7章(2002)中作为单重态氧猝灭剂例示出的化合物。进而,作为单重态氧猝灭剂,还可以举出以具有硫原子的化合物作为配位体的金属络合物。作为这样的单重态氧猝灭剂,例如可以举出以双二硫代-α-二酮、双苯基二硫醇以及硫化双酚作为配位体的镍络合物、钴络合物、铜络合物、锰络合物、铂络合物等过渡金属螯合化合物。
这些例示出的化合物中,从活性高的方面出发,适当的单重态氧猝灭剂优选三甲胺、三乙胺、二乙基(2-羟基乙基)胺、二乙基(2-甲氧基乙基)胺、二乙基(2-氰基乙基)胺、二乙基(7-氨基庚基)胺、三丁胺、二(2-羟基乙基)-叔丁胺、碱、1-甲基哌啶、4-羟基-1,2,2,6,6-五甲基哌啶、1-环己基哌啶、奎宁环、哌嗪、1,4-二氮杂双环[2.2.2]辛烷等叔胺类;呋喃、2-甲基呋喃、糠基胺、2-甲氧基呋喃、糠醇、糠基甲醚、2-呋喃甲酸、2-乙烯基呋喃、α-甲基糠醇、α-苄基糠醇、α-苯基乙基糠醇、α-(3-苯基丙基)糠醇、α-二苯甲基糠醇、α,α-二苯基糠醇、2-乙酰基呋喃、N-甲基糠基胺、2-苯基呋喃、3-苯基呋喃、3-(4’-氟苯基)呋喃、2-(4’-氯苯基)呋喃、3-(4’-溴苯基)呋喃、2-(4’-甲基苯基)呋喃、3-(4’-甲基苯基)呋喃、2-(4’-甲氧基苯基)呋喃、3-(4’-甲氧基苯基)呋喃、2,4-二甲基呋喃、2,5-二甲基呋喃、2,5-二苯基呋喃、3,4-二苯基呋喃、2,3,4,5,-四苯基呋喃、2,2(2,5)二氧三环十四碳四烯、异苯并呋喃、1,3-二苯基异苯并呋喃、1,3-二苯基-5,6-二甲基异苯并呋喃、1,3,4,7-四苯基异苯并呋喃、1,3,4,5,6,7-六苯基异苯并呋喃等呋喃化合物,其中更优选叔胺类,特别优选三乙二胺。
作为本发明的光聚合敏化剂的烷氧基蒽也与单重态氧反应而发生分解,从这一意味来说,其也是单重态氧淬灭剂,因此与烷氧基蒽化合物相比,对于单重态氧更具有活性的化合物能够通过少量添加得到效果,因而是优选的,优选单重态氧的淬灭剂的速度常数k比烷氧基蒽化合物更大的化合物。
(光聚合敏化剂组合物)
通过在上述通式(1)所表示的烷氧基蒽化合物中添加单重态氧猝灭剂,能够制成光聚合敏化剂组合物。
单重态氧猝灭剂相对于本发明的烷氧基蒽化合物的添加量也取决于单重态氧猝灭剂,使用0.1~10重量倍、更优选使用0.5~5重量倍。
本发明的光聚合敏化剂组合物中优选进一步含有抗氧化剂。作为抗氧化剂,可以举出酚系抗氧化剂、胺系抗氧化剂、磷系抗氧化剂、硫系抗氧化剂等。
作为酚系抗氧化剂,例如可以举出丁基羟基甲苯、2,6-叔丁基-4-甲基苯酚、正十八烷基-3-(3’5’-二叔丁基4’-羟基苯基)丙酸酯、α-生育酚、芥子醇、维生素E、羟基苯基丙酸酯系化合物、羟基苄基系化合物、苯硫酚系化合物、烷烃二基酚系化合物等。
作为羟基苯基丙酸酯系化合物的具体例,可以举出3,9-双[2-[3-(3-叔丁基-4-羟基-5-甲基苯基)丙酰氧基]-1,1-二甲基乙氧基]-2,4,8,10-四氧杂螺[5.5]十一烷、季戊四醇四[3-(3,5-二叔丁基-4-羟基苯基)丙酸酯]、三乙二醇-双[3-(3-叔丁基-5-甲基-4-羟基苯基)丙酸酯]、1,6-己二醇-双[3-(3,5-二叔丁基-4-羟基苯基)丙酸酯]、2,2-硫代-二乙撑双[3-(3,5-二叔丁基-4-羟基苯基)丙酸酯]、十八烷基-[3-(3,5-二叔丁基-4-羟基苯基)丙酸酯]、四[亚甲基-3-(3,5'-二叔丁基-4'-羟基苯基丙酸酯)]甲烷等。
作为羟基苄基系化合物的具体例,可以举出1,3,5,-三甲基-2,4,6,-三(3',5'-二叔丁基-4-羟基苄基)苯、1,3,5-三(4-羟基苄基)苯、三-(3,5-二叔丁基-4-羟基苄基)-异氰脲酸酯、1,3,5-三(4-叔丁基-3-羟基-2,6-二甲基苄基)-异氰脲酸酯等。
作为苯硫酚系化合物的具体例,可以举出4,4'-硫代双(6-叔丁基-3-甲基苯酚),作为硫基甲基酚系化合物的具体例,可以举出2,4-双[(辛硫基)甲基]-邻甲酚等。
作为烷烃二基酚系化合物的具体例,可以举出N,N'-六亚甲基双(3,5-二叔丁基-4-羟基-氢化肉桂酰胺)、2,2'-亚甲基双(4-甲基-6-叔丁基苯酚)、4,4'-亚丁基-双(3-甲基-6-叔丁基苯酚)、1,1,3-三(2-甲基-4-羟基-5-叔丁基苯基)丁烷等。
作为具有酚醛结构的抗氧化剂的市售品,例如可以举出ADKSTAB AO-20、ADKSTABAO-30、ADKSTAB AO-40、ADKSTAB AO-50、ADKSTAB AO-60、ADKSTAB AO-70、ADKSTAB AO-80、ADKSTAB AO-330(以上来自ADEKA公司)、Sumilizer GM、Sumilizer GS、Sumilizer MDP-S、Sumilizer BBM-S、Sumilizer WX-R、Sumilizer GA-80(以上来自住友化学公司)、IRGANOX1010、IRGANOX 1035、IRGANOX 1076、IRGANOX 1098、IRGANOX 1135、IRGANOX 1330、IRGANOX1726、IRGANOX 1425WL、IRGANOX 1520L、IRGANOX 245、IRGANOX 259、IRGANOX 3114、IRGANOX 565、IRGAMOD 295(以上来自BASF公司)、YOSHINOX BHT、YOSHINOX BB、YOSHINOX2246G、YOSHINOX 425、YOSHINOX 250、YOSHINOX 930、YOSHINOX SS、YOSHINOX TT、YOSHINOX917、YOSHINOX 314(以上来自Api Corporation公司)等。
作为胺系抗氧化剂的具体例,可以举出4-苯甲酰基氧基-2,2,6,6-四甲基哌啶、双(2,2,6,6-四甲基-4-哌啶基)癸二酸酯、双(N-甲基-2,2,6,6-四甲基-4-哌啶基)癸二酸酯等。作为市售品,可以举出ADKSTAB(注册商标)LA-77、LA-57、LA-52、LA-62、LA-63、LA-67、LA-68(株式会社ADEKA制)等。另外还可以举出TINUVIN(注册商标)123、TINUVIN 144、TINUVIN 622、TINUVIN 765、TINUVIN 944(BASF公司制造)等。
作为磷系抗氧化剂的具体例,可以举出亚磷酸三苯酯、三壬基苯基亚磷酸酯、三(2,4-二叔丁基苯基)亚磷酸酯、磷酸三甲酯、磷酸三乙酯、磷酸三丁酯、磷酸三辛酯、磷酸三苯酯、磷酸三甲苯酚酯、三(壬基苯基)磷酸酯、2-乙基苯基二苯基磷酸酯、3,9-双(2,6-二叔丁基-4-甲基苯氧基)-2,4,8,10-四氧杂-3,9-二磷杂螺[5.5]十一烷、二异癸基季戊四醇二亚磷酸酯、双(2,4-二叔丁基苯基)季戊四醇二亚磷酸酯、2,2'-亚甲基双(4,6-二叔丁基-1-苯基氧基)(2-乙基己氧基)磷、6-[3-(3-叔丁基-4-羟基-5-甲基苯基)丙氧基]-2,4,8,10-四叔丁基二苯并[d,f][1,3,2]二氧磷杂七环、亚磷酸三苯酯、二苯基异癸基亚磷酸酯、苯基二异癸基亚磷酸酯、4,4'-亚丁基-双(3-甲基-6-叔丁基苯基双十三烷基)亚磷酸酯、十八烷基亚磷酸酯、三(壬基苯基)亚磷酸酯、9,10-二氢-9-氧杂-10-磷杂菲-10-氧化物、10-(3,5-二叔丁基-4-羟基苄基)-9,10-二氢-9-氧杂-10-磷杂菲-10-氧化物、10-癸氧基-9,10-二氢-9-氧杂-10-磷杂菲-10-氧化物、三(2,4-二叔丁基苯基)亚磷酸酯、环状新戊烷四基双(2,4-二叔丁基苯基)亚磷酸酯、环状新戊烷四基双(2,6-二叔丁基苯基)亚磷酸酯、2,2-亚甲基双(4,6-二叔丁基苯基)辛基亚磷酸酯、四(2,4-二叔丁基苯基)[1,1-联苯]-4,4'-二基双亚膦酸酯、双[2,4-双(1,1-二甲基乙基)-6-甲基苯基]乙酯、膦酸等。
作为硫系抗氧化剂,例如可以举出硫代丙酸酯系化合物、巯基苯并咪唑系化合物。作为硫代丙酸酯系化合物的具体例,可以举出2,2-双({[3-(十二烷基硫代)丙酰基]氧基}甲基)-1,3-丙烷二基-双[3-(十二烷基硫代)丙酸酯]、二月桂基-3,3'-硫代二丙酸酯、二肉豆蔻基-3,3'-硫代二丙酸酯、二硬脂基-3,3'-硫代二丙酸酯、季戊四醇四(3-月桂基硫代丙酸酯)等。作为巯基苯并咪唑系化合物的具体例,可以举出2-巯基苯并咪唑等。
这些例示的化合物中,从活性高的方面出发,优选酚系抗氧化剂。
抗氧化剂相对于本发明的烷氧基蒽化合物的添加量也取决于抗氧化剂,使用0.01~5重量倍、更优选使用0.02~3重量倍。
本发明的光聚合敏化剂组合物中,只要无损于本发明的效果,也可以进一步添加光稳定剂。还可以进一步添加通式(1)所表示的烷氧基蒽化合物以外的光聚合敏化剂。另外,也可以添加溶剂制成浆料或溶液状态。
(光聚合性组合物)
本发明的光聚合敏化剂组合物在光自由基聚合、光阳离子聚合中均具有活性,因此光聚合性组合物可以为光自由基聚合组合物、也可以为光阳离子组合物。另外,还可以为进行光自由基聚合和光阳离子聚合这两者的杂化组合物。
(光自由基聚合性组合物)
本发明的光聚合敏化剂组合物在自由基聚合反应中起到光自由基聚合敏化剂的作用。通过将该光自由基聚合敏化剂组合物与光自由基聚合引发剂和自由基聚合性化合物混合,能够制成光自由基聚合性组合物。该光自由基聚合性组合物通过照射300nm至500nm波长范围的光能够容易地进行光聚合,能够抑制其固化物的着色。
作为本发明中使用的自由基聚合引发剂,可以举出苄基甲基缩酮系、α-羟基烷基苯酮系聚合引发剂、α-氨基烷基苯酮系等自由基聚合引发剂等。关于具体的化合物,作为苄基甲基缩酮系自由基聚合引发剂,可以举出2,2-二甲氧基-1,2-二苯基乙烷-1-酮(商品名“Irgacure 651”、BASF公司制造)。作为α-羟基烷基苯酮系的自由基聚合引发剂,可以举出1-羟基环己基苯基甲酮(商品名“Irgacure 184”、BASF公司制造)、2-羟基-2-甲基-1-苯基丙烷-1-酮(商品名“Darocure 1173”、BASF公司制造)、1-[4-(2-羟基乙氧基)-苯基]-2-羟基-2-甲基-1-丙烷-1-酮(商品名“Irgacure 2959”、BASF公司制造)、2-羟基-1-{4-[4-(2-羟基-2-甲基丙酰基)-苄基]苯基}-2-甲基-1-酮(商品名“Irgacure 127”、BASF公司制造)等。作为α-氨基烷基苯酮系的自由基聚合引发剂,可以举出2-甲基-1-(4-甲硫基苯基)-2-吗啉基-1-丙酮(商品名“Irgacure 907”、BASF公司制造)、2-苄基-2-二甲氨基-1-(4-吗啉代苯基)-1-丁酮(商品名“Irgacure 369”、BASF公司制造)等。作为苯乙酮系的自由基聚合引发剂,可以举出苯乙酮、2-羟基-2-苯基苯乙酮、2-乙氧基-2-苯基苯乙酮、2-甲氧基-2-苯基苯乙酮、2-异丙氧基-2-苯基苯乙酮、2-异丁氧基-2-苯基苯乙酮等。作为苯偶酰系自由基聚合引发剂,可以举出苯偶酰、4,4’-二甲氧基苯偶酰等,作为蒽醌系自由基聚合引发剂,可以举出2-乙基蒽醌、2-叔丁基蒽醌、氨基烷基苯酮系等。
本发明的自由基聚合敏化剂组合物相对于自由基聚合引发剂的添加量为0.01重量倍以上且小于10重量倍、更优选为0.05重量倍以上且小于1.0重量倍。该添加量小于0.01重量倍时,缺乏敏化剂的效果,另外,即使添加10重量倍以上,性能也不会提高至其以上,因此没有添加的意义。
本发明的自由基聚合敏化剂的作用机理不明确,据认为是由于,其吸收紫外区域的光而激发烷氧基蒽化合物,该激发种对自由基聚合引发剂赋予能量,通过自由基聚合引发剂的裂解而促进自由基种的产生。
作为本发明中使用的自由基聚合性化合物,例如可以举出苯乙烯、对羟基苯乙烯、醋酸乙烯酯、丙烯酸、甲基丙烯酸、丙烯腈、甲基丙烯腈、丙烯酰胺、丙烯酸酯、甲基丙烯酸酯等或它们的低聚物等。
自由基聚合性化合物中,优选丙烯酸酯、甲基丙烯酸酯,特别优选二官能丙烯酸酯、三官能丙烯酸酯等多官能丙烯酸酯。
作为丙烯酸酯,可以举出下述具体例。首先,作为二官能丙烯酸酯,可以举出乙氧基化双酚A二丙烯酸酯、9,9-双[4-(2-丙烯酰氧基乙氧基)苯基]芴、三环癸烷二甲醇二丙烯酸酯、1,10-癸二醇二丙烯酸酯、1,9-壬二醇二丙烯酸酯、二丙二醇二丙烯酸酯、三丙二醇二丙烯酸酯、1,3-丁二醇二丙烯酸酯、1,4-丁二醇二丙烯酸酯、二乙二醇二丙烯酸酯、1,6-己二醇二丙烯酸酯、四乙二醇二丙烯酸酯、三乙二醇二丙烯酸酯、三丙二醇二丙烯酸酯、乙氧基化(3)双酚A二丙烯酸酯、烷氧基化新戊二醇二丙烯酸酯等。
作为二官能以上的多官能丙烯酸酯,可以举出乙氧基化异氰脲酸三丙烯酸酯、ε-己内酯改性三-(2-丙烯酰氧基乙基)异氰脲酸酯、季戊四醇三丙烯酸酯、三羟甲基丙烷三丙烯酸酯、双三羟甲基丙烷四丙烯酸酯、乙氧基化季戊四醇四丙烯酸酯、季戊四醇四丙烯酸酯、二季戊四醇六丙烯酸酯、三(2-羟基乙基)异氰脲酸酯三丙烯酸酯、乙氧基化三羟甲基丙烷三丙烯酸酯、季戊四醇三丙烯酸酯、季戊四醇四丙烯酸酯、双三羟甲基丙烷四丙烯酸酯、二季戊四醇五丙烯酸酯等。另外,还可以使用环氧丙烯酸酯、聚氨酯丙烯酸酯、聚酯丙烯酸酯、聚丁二烯丙烯酸酯、多元醇丙烯酸酯、聚醚丙烯酸酯、有机硅树脂丙烯酸酯、酰亚胺丙烯酸酯等。
同样地,关于甲基丙烯酸酯化合物,作为二官能甲基丙烯酸酯,可以举出乙二醇二甲基丙烯酸酯、二乙二醇二甲基丙烯酸酯、三乙二醇二甲基丙烯酸酯、乙氧基化双酚A二甲基丙烯酸酯、三环癸烷二甲醇二甲基丙烯酸酯、1,6-己二醇二甲基丙烯酸酯、1,9-壬二醇二甲基丙烯酸酯、新戊二醇二甲基丙烯酸酯、甘油二甲基丙烯酸酯、四乙二醇二甲基丙烯酸酯、聚乙二醇二甲基丙烯酸酯、1,4-丁二醇二甲基丙烯酸酯、二乙二醇二甲基丙烯酸酯、1,3-丁烯二醇二甲基丙烯酸酯、乙氧基化双酚A二甲基丙烯酸酯等。作为二官能以上的多官能甲基丙烯酸酯,可以举出三羟甲基丙烷三甲基丙烯酸酯等。
这些自由基聚合性化合物可以单独使用,也可以将两种以上组合使用。
相对于自由基聚合性化合物,本发明的光自由基聚合引发剂和光自由基聚合敏化剂组合物的合计添加量为0.01重量%以上且小于3.0重量%、优选为0.05重量%以上且小于1.0重量%。光自由基聚合引发剂和光自由基聚合敏化剂组合物的合计添加量小于0.01重量%时,则光聚合速度可能变慢,另一方面,光自由基聚合引发剂和光自由基聚合敏化剂组合物的合计添加量为3.0重量%以上时,光聚合物的物性可能会劣化,因而不优选。
(光阳离子聚合性组合物)
本发明的光聚合敏化剂组合物在阳离子聚合反应中起到光阳离子聚合敏化剂的作用。通过将该光阳离子聚合敏化剂组合物与光阳离子聚合引发剂和阳离子聚合性化合物混合,能够制成光阳离子聚合性组合物。该光阳离子聚合性组合物通过照射300nm至500nm波长范围的光能够容易地进行光聚合,能够抑制其固化物的着色。
(光阳离子聚合引发剂)
本发明中使用的光阳离子聚合引发剂使用通过光照射而产生对于光阳离子聚合性化合物的聚合引发种的聚合引发剂。特别是适当地使用通过光照射而产生布朗斯台德酸或路易斯酸等的光产酸剂。
作为这样的光阳离子聚合引发剂,可以举出磺酸酯、酰亚胺磺酸酯、二烷基-4-羟基锍盐、芳基磺酸-对硝基苄基酯、硅烷醇-铝络合物、(η6-苯)(η5-环戊二烯)铁(II)等,更具体地说,可以举出苯偶姻甲苯磺酸酯、2,5-二硝基苄基甲苯磺酸酯、N-甲苯磺酰基邻苯二甲酰亚胺等。
进而可以举出芳香族碘鎓盐、芳香族锍盐、芳香族重氮盐、芳香族鏻盐、三嗪化合物、铁-芳烃络合物等。具体地说,可以举出二苯基碘鎓、二甲苯基碘鎓、双(对叔丁基苯基)碘鎓、双(对氯苯基)碘鎓等碘鎓的氯化物、溴化物、氟硼酸盐、六氟磷酸盐、六氟锑酸盐、三氟甲磺酸盐、对甲苯磺酸盐等碘鎓盐、三苯基锍、二苯基(4-甲氧基苯基)锍、(4-苯氧基苯基)二苯基锍、二苯基(4-苯硫基苯基)锍、三(4-叔丁基苯基)锍、三(4-甲基苯基)锍、三芳基锍、S,S-二烷基-S-苯甲酰甲基锍等锍的氯化物、溴化物、氟硼酸盐、六氟磷酸盐、六氟锑酸盐、三氟甲磺酸盐、全氟-1-丁烷磺酸盐等锍盐、5-芳基噻蒽鎓盐的氯化物、溴化物、氟硼酸盐、六氟磷酸盐、六氟锑酸盐、三氟甲磺酸盐、全氟-1-丁烷磺酸盐等噻蒽鎓盐、2,4,6-三(三氯甲基)-1,3,5-三嗪、2-苯基-4,6-双(三氯甲基)-1,3,5-三嗪、2-甲基-4,6-双(三氯甲基)-1,3,5-三嗪等的2,4,6-取代-1,3,5-三嗪化合物,但并不限于这些。
这些罗列出的光阳离子聚合引发剂中,芳香族锍盐和芳香族碘鎓盐的效率高且容易获得,因而优选。
例如,作为芳香族锍盐,可以举出S,S,S’,S’-四苯基-S,S’-(4,4’-硫代二苯基)二锍双六氟磷酸盐、二苯基-4-苯硫基苯基锍六氟磷酸盐、三苯基锍六氟磷酸盐等,例如可以使用陶氏化学制造、商品名:UVI6992;San-Apro公司制造、商品名:CPI-100P、CPI-101A、CPI-200K、CPI-210S等;BASF公司制造、商品名:Irgacure 270等(“Irgacure”是BASF公司的注册商标)。作为芳香族碘鎓盐,可以举出4-异丁基苯基-4’-甲基苯基碘鎓六氟磷酸盐、双(十二烷基苯基)碘鎓六氟锑酸盐、4-异丙基苯基-4’-甲基苯基碘鎓四(五氟苯基)硼酸盐等,例如可以举出BASF公司制造、商品名:Irgacure 250;Rhodia公司制造、商品名:Rhodorsil 2074(“Rhodorsil”是Rhodia公司的注册商标)等。
这些光阳离子聚合引发剂的用量没有特别限定,通常相对于光聚合性组合物中的光阳离子聚合性化合物,可以以0.001重量%~20重量%的范围使用,进一步优选可以以0.01重量%~10重量%的范围使用。
本发明中使用的光阳离子聚合性化合物可以为通过布朗斯台德酸或路易斯酸等酸进行阳离子聚合的化合物。例如可以举出包含环氧环、氧杂环丁烷环、四氢呋喃环、四氢吡喃环、二氧戊环、二噻烷环、三噻烷环、二噻茂烷环等的环状醚类或环状硫醚类、硫醚类、乙烯基醚类、内酯等。
作为上述光阳离子聚合性化合物,例如可以举出二甘油二醚、苯基缩水甘油醚、对叔丁基苯基缩水甘油醚、丁基缩水甘油醚、2-乙基己基缩水甘油醚、烯丙基缩水甘油醚、1,2-环氧丁烷、1,3-丁二烯单氧化物、1,2-环氧癸烷、环氧氯丙烷、1,2-环氧癸烷、氧化苯乙烯、环氧环己烷、3-甲基丙烯酰氧基甲基环氧环己烷、3-丙烯酰氧基甲基环氧环己烷、3-乙烯基环氧环己烷、(甲基)丙烯酸缩水甘油酯、乙烯基环氧环己烷、4-乙烯基环氧环己烷、环氧六氢邻苯二甲酸二辛酯、环氧六氢邻苯二甲酸二-2-乙基己酯等在分子内具有1个环氧环的化合物;双酚A二缩水甘油醚、双酚F二缩水甘油醚、双酚S二缩水甘油醚、溴化双酚A二缩水甘油醚、溴化双酚F二缩水甘油醚、溴化双酚S二缩水甘油醚、环氧酚醛清漆树脂、氢化双酚A二缩水甘油醚、氢化双酚F二缩水甘油醚、氢化双酚S二缩水甘油醚、3’,4’-环氧环己基甲基-3,4-环氧环己基羧酸酯(例如DOW公司制造UVR6105、UVR6110;Daicel公司制造Celloxide 2021P、“Celloxide”为株式会社Daicel的注册商标;等等)、1,2-环氧-4-乙烯基环己烷(例如Daicel公司制造Celloxide 2000)、2-(3,4-环氧环己基-5,5-螺环-3,4-环氧)环己烷-间二氧六环、双(3,4-环氧环己基甲基)己二酸酯、双(3,4-环氧-6-甲基环己基甲基)己二酸酯、3,4-环氧-6-甲基环己基-3’,4’-环氧-6’-甲基环己烷羧酸酯、亚甲基双(3,4-环氧环己烷)、二氧化双环戊二烯、乙二醇的二(3,4-环氧环己基甲基)醚、乙撑双(3,4-环氧环己基羧酸酯)、1,4-丁二醇二缩水甘油醚、1,6-己二醇二缩水甘油醚、甘油三缩水甘油醚、三羟甲基丙烷三缩水甘油醚、聚乙二醇二缩水甘油醚、聚丙二醇二缩水甘油醚类、1,1,3-十四烷二烯二氧化物、苧烯二氧化物、1,2,7,8-二环氧辛烷、1,2,5,6-二环氧环辛烷等在分子中具有2个以上环氧环的化合物;3-乙基-3-羟基甲基氧杂环丁烷(氧杂环丁烷醇)、2-乙基己基氧杂环丁烷、亚二甲苯基双氧杂环丁烷、3-乙基-3{[(3-乙基氧杂环丁烷-3-基)甲氧基]甲基}氧杂环丁烷等具有氧杂环丁烷环的化合物;甲基乙烯基醚、乙基乙烯基醚、正丙基乙烯基醚、正丁基乙烯基醚、环己基乙烯基醚、异丁基乙烯基醚、2-乙基己基乙烯基醚、2-羟基乙基乙烯基醚、4-羟基丁基乙烯基醚、环己烷甲醇单乙烯基醚、二乙二醇单乙烯基醚、1,4-丁二醇二乙烯基醚、环己烷二甲醇二乙烯基醚、二乙二醇二乙烯基醚、三乙二醇二乙烯基醚、烯丙基乙烯基醚等乙烯基醚类;等等。
这些光阳离子聚合性化合物可以使用1种,也可以使用2种以上。这些光阳离子聚合性化合物中,从阳离子聚合性的高度、获得容易性的方面等出发,优选具有环氧环、氧杂环丁烷环的化合物、乙烯基醚类。特别优选3’,4’-环氧环己基甲基-3,4-环氧环己基羧酸酯等脂环式环氧化合物。
相对于阳离子聚合性化合物,本发明的光阳离子聚合引发剂和光阳离子聚合敏化剂组合物的合计添加量为0.01重量%以上且小于3.0重量%、优选为0.05重量%以上且小于1.0重量%。光阳离子聚合引发剂和光阳离子聚合敏化剂组合物的合计添加量小于0.01重量%时,光聚合速度可能变慢,另一方面,光阳离子聚合引发剂和光阳离子聚合敏化剂组合物的合计添加量为3.0重量%以上时,光聚合物的物性可能会劣化,因而不优选。
(杂化组合物)
本发明的光聚合敏化剂组合物起到光自由基聚合敏化剂组合物的作用、也起到光阳离子聚合性组合物的作用,因此也可以用于含有自由基聚合性化合物和阳离子聚合性化合物这两者的杂化组合物。
(其他添加物)
本发明的光聚合性组合物中可以在不损害本发明效果的范围内进一步以常规使用范围混配颜料、染料等着色剂、有机或无机填充剂、流平剂、表面活性剂、消泡剂、增稠剂、阻燃剂、抗氧化剂、稳定剂、润滑剂、增塑剂、防水剂等各种树脂添加剂。
作为着色剂,可以举出黑色颜料、黄色颜料、红色颜料、蓝色颜料、白色颜料等。作为黑色颜料,例如可以举出炭黑、乙炔黑、灯黑、苯胺黑等。作为黄色颜料,例如可以举出铬黄、锌黄、镉黄、氧化铁黄、矿物坚牢黄、钛镍黄、脐橙黄、萘酚黄S、汉撒黄G、汉撒黄10G、联苯胺黄G、联苯胺黄GR、喹啉黄色淀、永固黄NCG、柠檬黄色淀等。作为红色颜料,例如可以举出氧化铁红、镉红、铅丹、硫化镉汞、永固红4R、立索红、色淀红D、亮胭脂6B、曙红色淀、若丹明色淀B、茜素色淀、亮胭脂3B等。作为蓝色颜料,例如可以举出普鲁士蓝、钴蓝、碱蓝色淀、维多利亚蓝色淀、酞菁蓝、无金属酞菁蓝、酞菁蓝部分氯化物、坚牢天蓝、阴丹士林蓝BC等。作为白色颜料,例如可以举出锌白、氧化钛、锑白、硫化锌等。作为其他颜料,例如可以举出重晶石粉、碳酸钡、粘土、二氧化硅、白炭黑、滑石、矾土白等。其中,三芳基胺系染料中的三芳基胺本身为单重态氧猝灭剂,因此本发明的效果弱,由此被排除。
(聚合方法)
本发明的光聚合性组合物的聚合可以以膜状进行,也可以以块状聚合。以膜状进行聚合的情况下,将该光聚合性组合物制成液态,例如在聚酯膜或粘性膜等基材上使用例如刮条涂布机等涂布光聚合性组合物,照射包含波长为300nm至500nm的光的光使其固化,由此进行聚合。
(涂布)
作为以膜状聚合的情况下所使用的基材,主要使用膜、纸、铝箔、金属等,没有特别限定。关于作为基材的膜使用的材料,使用聚酯、三乙酰纤维素(TAC)、聚乙烯醇(PVA)等。该基材膜的膜厚通常使用小于100μm的膜厚。为了调整涂布光聚合性组合物而得到的涂膜的膜厚,所使用的刮条涂布机没有特别限定,使用能够将膜厚调整为1μm以上且小于100μm的刮条涂布机。另一方面,也可以通过旋转涂布法或丝网印刷法形成更薄的膜厚或更厚的膜厚来进行涂布。
(照射源)
向由这样制备的光聚合性组合物构成的涂膜上以1~2000mW/cm2的程度的强度照射包含波长为300nm至500nm范围的光的光,由此可以得到光聚合物。作为所使用的照射源,只要为在波长300nm至500nm之间具有发光光谱的灯即能够使用,还能够使用Fusion公司制造的D型灯泡、V型灯泡等无电极灯、氙灯、黑光灯、超高压水银灯、金属卤化物灯、镓掺杂灯、紫外LED、激光器等。另外,即使利用太阳光也能够使其固化。特别是出于本发明的光聚合敏化剂组合物有效的原因,优选包含370nm至420nm范围的光的光,在实际使用中特别优选以405nm的光作为中心波长的紫外LED、以395nm的光作为中心波长的紫外LED、以385nm光作为中心波长的紫外LED和以375nm的光作为中心波长的紫外LED、405nm的半导体激光器。
实施例
下面基于实施例详细地说明本发明,但这些实施例是用于例示而举出的。即,以下的实施例并非旨在概括性说明或者直接将本发明限制在所记载的方式。因此,只要不超出其宗旨,本发明并不限于以下的记载例。另外,只要没有特殊声明,则全部的份和百分数为重量基准。
<UV光谱的测定>
将测定试样按照浓度为10ppm的方式添加至乙腈(和光纯药)中,使其完全溶解,由此制备测定试样溶液。将该试样溶液按照不产生气泡的方式装入光程长1cm的石英池中至达到约80%的高度为止,置于UV2600(岛津制作所制)中,测定UV光谱。
(实施例1)烷氧基蒽的分解抑制实验
将9,10-二丁氧基蒽(DBA)以1wt%添加至1-甲基-2-吡咯烷酮(东京化成公司制造)中,添加5wt%作为单重态氧猝灭剂的三乙二胺。将该溶液装入不锈钢杯中,用PET膜和石英玻璃盖上。将其投入耐光性试验机(Atlas Suntest CPS+、东洋精机公司制造)中,照射4小时光。其后利用高效液相色谱法对于光照射前后的9,10-二丁氧基蒽(DBA)的量进行定量,计算出4小时后的9,10-二丁氧基蒽(DBA)的残存比例。将其结果示于表2。
(实施例2、3、比较例1)
作为单重态氧猝灭剂,以表1中的量添加表1中的化合物来代替三乙二胺,除此以外,利用与实施例1相同的方法进行光照射,计算出9,10-二丁氧基蒽(DBA)的残存比例。将其结果示于表2。
(实施例4)
除了单重态氧猝灭剂以外,进一步添加5wt%作为抗氧化剂的ADKSTAB AO-40(ADEKA公司制造、ADKSTAB为ADEKA公司的注册商标),除此以外,利用与实施例1相同的方法进行光照射,计算出9,10-二丁氧基蒽(DBA)的残存比例。将其结果示于表2。
[表1]
TEDA:三乙二胺
DMF:2,5-二甲基呋喃
FFA:糠醇
AO-40:ADKSTAB AO-40(酚性抗氧化剂)
[表2]
观察表2可知,在比较例1的未添加单重态氧猝灭剂的情况下,4小时后的DBA的残存率为3.7%,大部分DBA发生分解;与之相对,在添加了作为单重态氧猝灭剂的三乙二胺(TEDA)的实施例1的情况下,DBA的残存率非常高,进而由实施例4可知,通过将作为抗氧化剂的ADKSTAB AO-40与单重态猝灭剂三乙二胺(TEDA)合用,残存率进一步增高。可知在实施例2和3的添加了作为单重态氧猝灭剂的呋喃化合物的情况下,也具有一定的DBA分解抑制效果。由该结果可知,通过捕捉单重态氧,能够抑制烷氧基蒽化合物的分解。
<聚合物的制作和YI值的测定>
自由基聚合物的制作方法如下所述来进行制作。首先将作为间隔物的聚对苯二甲酸乙二醇酯(PET)膜(长18mm×宽1mm×厚0.1mm)载置于罩玻璃(长18mm×宽18mm×厚0.16mm)上的两端。将自由基聚合性组合物适量地滴落在该罩玻璃上的PET膜之间,覆盖另1张罩玻璃。由此以夹在2张罩玻璃之间的状态得到被调整为PET膜的厚度的自由基聚合性组合物。使用高压水银灯的光照射机(Eyegraphics公司制造Eye Cure Light1.5kW、从13.2cm的高度照射)对其照射5分钟紫外线(365nm光为55.2mW/cm2),得到聚合物。
对于该得到的聚合物立即利用紫外-可视分光光度计(岛津制作所公司制造UV-2600)测定190~800nm的透过率,使用色彩测定软件计算出YI值。
(实施例5)固化物的着色抑制实验
相对于作为自由基聚合性化合物的三羟甲基丙烷三丙烯酸酯(TMPTA)(东京化成公司制造)100重量份,添加作为光自由基聚合引发剂的Irgacure 184(1-羟基环己基苯基甲酮、BASF公司制造、Irgacure为BASF的注册商标)3.0重量份,添加作为光自由基聚合敏化剂的9,10-二丁氧基蒽(DBA)0.5重量份,进一步添加作为单重态氧猝灭剂的三乙二胺1.0重量份,制备光自由基聚合性组合物。利用高压水银灯对该光自由基聚合性组合物照射5分钟紫外线,制作自由基聚合物。立即测定透过率,计算出YI值。其结果,YI值为14.02(记载于表3)。
(实施例6)
除了将三乙二胺的添加量变更为5.0重量份以外,与实施例5同样地实施。其结果,YI值为11.18(记载于表3)。
(比较例2)
除了不添加三乙二胺以外,与实施例5同样地实施。其结果,YI值为16.13(记载于表3)。
(实施例7)
相对于作为自由基聚合性化合物的三羟甲基丙烷三丙烯酸酯(TMPTA)(东京化成公司制造)100重量份,添加作为光自由基聚合引发剂的Irgacure 250(4-异丁基苯基-4’-甲基苯基碘鎓六氟磷酸盐、BASF公司制造、Irgacure为BASF的注册商标)4.0重量份、作为光自由基聚合敏化剂的9,10-二丁氧基蒽(DBA)0.5重量份,进一步添加作为单重态氧猝灭剂的三乙二胺1.0重量份,制备光自由基聚合性组合物。利用高压水银灯对该光自由基聚合性组合物照射5分钟紫外线,制作自由基聚合物。立即测定透过率,计算出YI值。其结果YI值为15.25(记载于表3)。
(比较例3)
除了不添加三乙二胺以外,与实施例3同样地实施。其结果,YI值为17.02(记载于表3)。
[表3]
对于实施例5与比较例2以及实施例7与比较例3进行比较可知,对于含有蒽系光自由基敏化剂的光自由基聚合性组合物添加单重态氧猝灭剂时,能够抑制自由基聚合物的着色。这是由于,蒽系敏化剂使溶解氧或光自由基组合物表层的氧变化为单重态氧(激发状态的氧),该单重态氧促进蒽系敏化剂的分解,生成着色分解物,但通过在光自由基聚合性组合物中添加单重态氧猝灭剂,可抑制蒽系敏化剂的分解反应,防止来自DBA的着色分解物的生成。此外,对实施例5与实施例6进行比较可知,通过大量添加单重态氧猝灭剂,可更高效地捕捉单重态氧,进一步抑制蒽系敏化剂的分解,抑制固化物的着色。
工业实用性
本发明的含有包含通式(1)所表示的烷氧基蒽化合物的光聚合敏化剂和单重态氧猝灭剂的光聚合敏化剂组合物作为感应包含波长为300nm至500nm波长范围的光而将自由基聚合引发剂活化的自由基聚合敏化剂组合物是有用的,此外,本发明的光聚合敏化剂组合物能够抑制因光照射所引起的来自通式(1)所表示的烷氧基蒽化合物的着色分解物的生成,并且能够抑制使包含该光聚合敏化剂组合物的光聚合性组合物聚合而得到的固化物的着色,是在产业上非常有用的光聚合敏化剂组合物。
Claims (12)
1.一种光聚合敏化剂组合物,其含有光聚合敏化剂和单重态氧猝灭剂,该光聚合敏化剂含有通式(1)所表示的烷氧基蒽化合物,其特征在于,
该单重态氧猝灭剂为三甲胺、三乙胺、二乙基(2-羟基乙基)胺、二乙基(2-甲氧基乙基)胺、二乙基(2-氰基乙基)胺、二乙基(7-氨基庚基)胺、三丁胺、二(2-羟基乙基)-叔丁胺、碱、1-甲基哌啶、4-羟基-1,2,2,6,6-五甲基哌啶、1-环己基哌啶、奎宁环、哌嗪、1,4-二氮杂双环[2.2.2]辛烷(别称:三乙二胺)、呋喃、2-甲基呋喃、糠基胺、2-甲氧基呋喃、糠醇、糠基甲醚、2-呋喃甲酸、2-乙烯基呋喃、α-甲基糠醇、α-苄基糠醇、α-苯基乙基糠醇、α-(3-苯基丙基)糠醇、α-二苯甲基糠醇、α,α-二苯基糠醇、2-乙酰基呋喃、N-甲基糠基胺、2-苯基呋喃、3-苯基呋喃、3-(4’-氟苯基)呋喃、2-(4’-氯苯基)呋喃、3-(4’-溴苯基)呋喃、2-(4’-甲基苯基)呋喃、3-(4’-甲基苯基)呋喃、2-(4’-甲氧基苯基)呋喃、3-(4’-甲氧基苯基)呋喃、2,4-二甲基呋喃、2,5-二甲基呋喃、2,5-二苯基呋喃、3,4-二苯基呋喃、2,3,4,5,-四苯基呋喃、2,2(2,5)二氧三环十四碳四烯、异苯并呋喃、1,3-二苯基异苯并呋喃、1,3-二苯基-5,6-二甲基异苯并呋喃、1,3,4,7-四苯基异苯并呋喃或1,3,4,5,6,7-六苯基异苯并呋喃,
[化1]
通式(1)中,n表示1或2的整数,R表示碳原子数1~12的烷基,X表示氢原子或碳原子数1~8的烷基中的任一者。
2.一种光聚合敏化剂组合物,其含有自由基聚合敏化剂和单重态氧猝灭剂,该自由基聚合敏化剂含有通式(2)所表示的烷氧基蒽化合物,其特征在于,
该单重态氧猝灭剂为三甲胺、三乙胺、二乙基(2-羟基乙基)胺、二乙基(2-甲氧基乙基)胺、二乙基(2-氰基乙基)胺、二乙基(7-氨基庚基)胺、三丁胺、二(2-羟基乙基)-叔丁胺、碱、1-甲基哌啶、4-羟基-1,2,2,6,6-五甲基哌啶、1-环己基哌啶、奎宁环、哌嗪、1,4-二氮杂双环[2.2.2]辛烷(别称:三乙二胺)、呋喃、2-甲基呋喃、糠基胺、2-甲氧基呋喃、糠醇、糠基甲醚、2-呋喃甲酸、2-乙烯基呋喃、α-甲基糠醇、α-苄基糠醇、α-苯基乙基糠醇、α-(3-苯基丙基)糠醇、α-二苯甲基糠醇、α,α-二苯基糠醇、2-乙酰基呋喃、N-甲基糠基胺、2-苯基呋喃、3-苯基呋喃、3-(4’-氟苯基)呋喃、2-(4’-氯苯基)呋喃、3-(4’-溴苯基)呋喃、2-(4’-甲基苯基)呋喃、3-(4’-甲基苯基)呋喃、2-(4’-甲氧基苯基)呋喃、3-(4’-甲氧基苯基)呋喃、2,4-二甲基呋喃、2,5-二甲基呋喃、2,5-二苯基呋喃、3,4-二苯基呋喃、2,3,4,5,-四苯基呋喃、2,2(2,5)二氧三环十四碳四烯、异苯并呋喃、1,3-二苯基异苯并呋喃、1,3-二苯基-5,6-二甲基异苯并呋喃、1,3,4,7-四苯基异苯并呋喃或1,3,4,5,6,7-六苯基异苯并呋喃,
[化2]
通式(2)中,R表示碳原子数1~12的烷基,X表示氢原子或碳原子数1~8的烷基中的任一者。
3.一种光聚合敏化剂组合物,其含有自由基聚合敏化剂和单重态氧猝灭剂,该自由基聚合敏化剂含有通式(3)所表示的烷氧基蒽化合物,其特征在于,
该单重态氧猝灭剂为三甲胺、三乙胺、二乙基(2-羟基乙基)胺、二乙基(2-甲氧基乙基)胺、二乙基(2-氰基乙基)胺、二乙基(7-氨基庚基)胺、三丁胺、二(2-羟基乙基)-叔丁胺、碱、1-甲基哌啶、4-羟基-1,2,2,6,6-五甲基哌啶、1-环己基哌啶、奎宁环、哌嗪、1,4-二氮杂双环[2.2.2]辛烷(别称:三乙二胺)、呋喃、2-甲基呋喃、糠基胺、2-甲氧基呋喃、糠醇、糠基甲醚、2-呋喃甲酸、2-乙烯基呋喃、α-甲基糠醇、α-苄基糠醇、α-苯基乙基糠醇、α-(3-苯基丙基)糠醇、α-二苯甲基糠醇、α,α-二苯基糠醇、2-乙酰基呋喃、N-甲基糠基胺、2-苯基呋喃、3-苯基呋喃、3-(4’-氟苯基)呋喃、2-(4’-氯苯基)呋喃、3-(4’-溴苯基)呋喃、2-(4’-甲基苯基)呋喃、3-(4’-甲基苯基)呋喃、2-(4’-甲氧基苯基)呋喃、3-(4’-甲氧基苯基)呋喃、2,4-二甲基呋喃、2,5-二甲基呋喃、2,5-二苯基呋喃、3,4-二苯基呋喃、2,3,4,5,-四苯基呋喃、2,2(2,5)二氧三环十四碳四烯、异苯并呋喃、1,3-二苯基异苯并呋喃、1,3-二苯基-5,6-二甲基异苯并呋喃、1,3,4,7-四苯基异苯并呋喃或1,3,4,5,6,7-六苯基异苯并呋喃,
[化3]
通式(3)中,R表示碳原子数1~12的烷基,X表示氢原子或碳原子数1~8的烷基中的任一者。
4.如权利要求1~3中任一项所述的光聚合敏化剂组合物,其特征在于,在含有单重态氧猝灭剂的同时进一步含有抗氧化剂。
5.如权利要求1~4中任一项所述的光聚合敏化剂组合物,其特征在于,单重态氧猝灭剂为1,4-二氮杂双环[2.2.2]辛烷(别称:三乙二胺)。
6.一种光聚合性组合物,其特征在于,其含有权利要求1~5中任一项所述的光聚合敏化剂组合物以及光聚合引发剂和聚合性化合物。
7.如权利要求6所述的光聚合性组合物,其特征在于,在光聚合性组合物中不含有三芳基甲烷染料。
8.如权利要求6或7所述的光聚合性组合物,其中,聚合性化合物为自由基聚合性化合物,光聚合引发剂为光自由基聚合引发剂。
9.如权利要求6或7所述的光聚合性组合物,其中,聚合性化合物为阳离子聚合性化合物,光聚合引发剂为光阳离子聚合引发剂。
10.如权利要求6或7所述的光聚合性组合物,其中,聚合性化合物含有自由基聚合性化合物和阳离子聚合性化合物这两者,光聚合引发剂含有光自由基聚合引发剂和光阳离子聚合引发剂这两者。
11.一种光聚合方法,其中,通过对权利要求6~10中任一项所述的光聚合性组合物照射包含波长为300nm至500nm波长范围的光的光而使其聚合。
12.如权利要求11所述的光聚合方法,其特征在于,包含波长为300nm至500nm波长范围的光的光的照射源是中心波长为375nm、385nm、395nm、405nm的紫外LED或405nm的半导体激光器。
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