JP6503736B2 - 二液型硬化性樹脂組成物 - Google Patents
二液型硬化性樹脂組成物 Download PDFInfo
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- JP6503736B2 JP6503736B2 JP2014551924A JP2014551924A JP6503736B2 JP 6503736 B2 JP6503736 B2 JP 6503736B2 JP 2014551924 A JP2014551924 A JP 2014551924A JP 2014551924 A JP2014551924 A JP 2014551924A JP 6503736 B2 JP6503736 B2 JP 6503736B2
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- 229940081974 saccharin Drugs 0.000 claims description 7
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- PSGCQDPCAWOCSH-BREBYQMCSA-N [(1r,3r,4r)-4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl] prop-2-enoate Chemical compound C1C[C@@]2(C)[C@H](OC(=O)C=C)C[C@@H]1C2(C)C PSGCQDPCAWOCSH-BREBYQMCSA-N 0.000 description 2
- JOBBTVPTPXRUBP-UHFFFAOYSA-N [3-(3-sulfanylpropanoyloxy)-2,2-bis(3-sulfanylpropanoyloxymethyl)propyl] 3-sulfanylpropanoate Chemical compound SCCC(=O)OCC(COC(=O)CCS)(COC(=O)CCS)COC(=O)CCS JOBBTVPTPXRUBP-UHFFFAOYSA-N 0.000 description 2
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- 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 2
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- 229910002013 Aerosil® 90 Inorganic materials 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
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- 239000004215 Carbon black (E152) Substances 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 229910021589 Copper(I) bromide Inorganic materials 0.000 description 1
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- PDQAZBWRQCGBEV-UHFFFAOYSA-N Ethylenethiourea Chemical compound S=C1NCCN1 PDQAZBWRQCGBEV-UHFFFAOYSA-N 0.000 description 1
- 101000720524 Gordonia sp. (strain TY-5) Acetone monooxygenase (methyl acetate-forming) Proteins 0.000 description 1
- 101001057956 Homo sapiens 55 kDa erythrocyte membrane protein Proteins 0.000 description 1
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- IPCRBOOJBPETMF-UHFFFAOYSA-N N-acetylthiourea Chemical compound CC(=O)NC(N)=S IPCRBOOJBPETMF-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- 235000004443 Ricinus communis Nutrition 0.000 description 1
- MNOILHPDHOHILI-UHFFFAOYSA-N Tetramethylthiourea Chemical compound CN(C)C(=S)N(C)C MNOILHPDHOHILI-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- RUDUCNPHDIMQCY-UHFFFAOYSA-N [3-(2-sulfanylacetyl)oxy-2,2-bis[(2-sulfanylacetyl)oxymethyl]propyl] 2-sulfanylacetate Chemical compound SCC(=O)OCC(COC(=O)CS)(COC(=O)CS)COC(=O)CS RUDUCNPHDIMQCY-UHFFFAOYSA-N 0.000 description 1
- AFSRWGCXJIBKFK-UHFFFAOYSA-I [V+5].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O Chemical compound [V+5].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O AFSRWGCXJIBKFK-UHFFFAOYSA-I 0.000 description 1
- FWKZJUMOSAVEBB-UHFFFAOYSA-I [V+5].[O-]C(=O)c1cccc2ccccc12.[O-]C(=O)c1cccc2ccccc12.[O-]C(=O)c1cccc2ccccc12.[O-]C(=O)c1cccc2ccccc12.[O-]C(=O)c1cccc2ccccc12 Chemical compound [V+5].[O-]C(=O)c1cccc2ccccc12.[O-]C(=O)c1cccc2ccccc12.[O-]C(=O)c1cccc2ccccc12.[O-]C(=O)c1cccc2ccccc12.[O-]C(=O)c1cccc2ccccc12 FWKZJUMOSAVEBB-UHFFFAOYSA-I 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 1
- 125000003670 adamantan-2-yl group Chemical group [H]C1([H])C(C2([H])[H])([H])C([H])([H])C3([H])C([*])([H])C1([H])C([H])([H])C2([H])C3([H])[H] 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
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- IHUNBGSDBOWDMA-AQFIFDHZSA-N all-trans-acitretin Chemical compound COC1=CC(C)=C(\C=C\C(\C)=C\C=C\C(\C)=C\C(O)=O)C(C)=C1C IHUNBGSDBOWDMA-AQFIFDHZSA-N 0.000 description 1
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- 125000003118 aryl group Chemical group 0.000 description 1
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- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- HECGKCOICWUUJU-UHFFFAOYSA-N bis(diphenylphosphanylmethyl)-phenylphosphane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)CP(C=1C=CC=CC=1)CP(C=1C=CC=CC=1)C1=CC=CC=C1 HECGKCOICWUUJU-UHFFFAOYSA-N 0.000 description 1
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- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
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- 239000011248 coating agent Substances 0.000 description 1
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- 239000010949 copper Substances 0.000 description 1
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 1
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- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
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- UBCNJHBDCUBIPB-UHFFFAOYSA-N diethyl 2,5-dibromohexanedioate Chemical compound CCOC(=O)C(Br)CCC(Br)C(=O)OCC UBCNJHBDCUBIPB-UHFFFAOYSA-N 0.000 description 1
- VFHVQBAGLAREND-UHFFFAOYSA-N diphenylphosphoryl-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 VFHVQBAGLAREND-UHFFFAOYSA-N 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 125000003438 dodecyl group Chemical group [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])C([H])([H])C([H])([H])* 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- HOXINJBQVZWYGZ-UHFFFAOYSA-N fenbutatin oxide Chemical compound C=1C=CC=CC=1C(C)(C)C[Sn](O[Sn](CC(C)(C)C=1C=CC=CC=1)(CC(C)(C)C=1C=CC=CC=1)CC(C)(C)C=1C=CC=CC=1)(CC(C)(C)C=1C=CC=CC=1)CC(C)(C)C1=CC=CC=C1 HOXINJBQVZWYGZ-UHFFFAOYSA-N 0.000 description 1
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- 238000001914 filtration Methods 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
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- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002432 hydroperoxides Chemical class 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 239000011256 inorganic filler Substances 0.000 description 1
- 229910003475 inorganic filler Inorganic materials 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
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- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
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- YLHXLHGIAMFFBU-UHFFFAOYSA-N methyl phenylglyoxalate Chemical compound COC(=O)C(=O)C1=CC=CC=C1 YLHXLHGIAMFFBU-UHFFFAOYSA-N 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- LSHROXHEILXKHM-UHFFFAOYSA-N n'-[2-[2-[2-(2-aminoethylamino)ethylamino]ethylamino]ethyl]ethane-1,2-diamine Chemical compound NCCNCCNCCNCCNCCN LSHROXHEILXKHM-UHFFFAOYSA-N 0.000 description 1
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- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
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- ZWLPBLYKEWSWPD-UHFFFAOYSA-N o-toluic acid Chemical compound CC1=CC=CC=C1C(O)=O ZWLPBLYKEWSWPD-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl 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])[H] 0.000 description 1
- FPLYNRPOIZEADP-UHFFFAOYSA-N octylsilane Chemical compound CCCCCCCC[SiH3] FPLYNRPOIZEADP-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000012766 organic filler Substances 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- UKODFQOELJFMII-UHFFFAOYSA-N pentamethyldiethylenetriamine Chemical compound CN(C)CCN(C)CCN(C)C UKODFQOELJFMII-UHFFFAOYSA-N 0.000 description 1
- HPAFOABSQZMTHE-UHFFFAOYSA-N phenyl-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)C1=CC=CC=C1 HPAFOABSQZMTHE-UHFFFAOYSA-N 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 229920000728 polyester Chemical group 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 229920005644 polyethylene terephthalate glycol copolymer Polymers 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- KRIOVPPHQSLHCZ-UHFFFAOYSA-N propiophenone Chemical compound CCC(=O)C1=CC=CC=C1 KRIOVPPHQSLHCZ-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 125000004079 stearyl 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])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
- 238000003756 stirring Methods 0.000 description 1
- 239000002344 surface layer Substances 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical class OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 description 1
- 150000003585 thioureas Chemical class 0.000 description 1
- 125000005425 toluyl group Chemical group 0.000 description 1
- 230000026683 transduction Effects 0.000 description 1
- 238000010361 transduction Methods 0.000 description 1
- ZESXUEKAXSBANL-UHFFFAOYSA-N trifluoromethyl prop-2-enoate Chemical compound FC(F)(F)OC(=O)C=C ZESXUEKAXSBANL-UHFFFAOYSA-N 0.000 description 1
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J4/00—Adhesives based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; adhesives, based on monomers of macromolecular compounds of groups C09J183/00 - C09J183/16
-
- 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
- C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
- C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
- C08F290/04—Polymers provided for in subclasses C08C or C08F
- C08F290/046—Polymers of unsaturated carboxylic acids or derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D151/00—Coating compositions based on graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Coating compositions based on derivatives of such polymers
- C09D151/003—Coating compositions based on graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Coating compositions based on derivatives of such polymers grafted on to macromolecular compounds obtained by reactions only involving unsaturated carbon-to-carbon bonds
-
- 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
- C08F220/00—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
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/12—Esters of monohydric alcohols or phenols
- C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
- C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
- C08F220/1804—C4-(meth)acrylate, e.g. butyl (meth)acrylate, isobutyl (meth)acrylate or tert-butyl (meth)acrylate
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Polymerisation Methods In General (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Polymerization Catalysts (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Description
(A)成分:(メタ)アクリルモノマーを重合させた主骨格を有し、主骨格の末端に(メタ)アクリル基を有するオリゴマー
(B)成分:脂環骨格を有する(メタ)アクリルモノマー
(C)成分:ハイドロパーオキサイド
(D)成分:銅化合物および/またはバナジウム化合物
(E)成分:サッカリン
(F)成分:パラフィン
(A)成分:(メタ)アクリルモノマーを重合させた主骨格を有し、主骨格の末端に(メタ)アクリル基を有するオリゴマー
(B)成分:脂環骨格を有する(メタ)アクリルモノマー
(C)成分:ハイドロパーオキサイド
(D)成分:銅化合物および/またはバナジウム化合物
(E)成分:サッカリン
(F)成分:パラフィン
本発明の第二の実施態様は、融点が40〜55℃の(F)成分を含む第一の実施態様に記載の二液型硬化性樹脂組成物である。
鎖状脂肪族炭化水素基、環状脂肪族炭化水素基、または芳香族炭化水素基ならびにこれらの誘導体基における炭素数について特に制限はなく、好ましくは1〜50であり、より好ましくは1〜20であり、さらに好ましくは1〜12である。
主骨格が(メタ)アクリルモノマーの重合体からなり、分子内に少なくとも2の(メタ)アクリル基を有する化合物を以下の通り製造した。臭化第一銅を触媒、ペンタメチルジエチレントリアミンを配位子、ジエチル−2,5−ジブロモアジペートを開始剤として、アクリル酸n−ブチルを重合し、この重合体300gをN,N−ジメチルアセトアミド(300mL)に溶解させ、アクリル酸カリウム5.3gを加え、窒素雰囲気下、70℃で3時間加熱攪拌し、両末端にアクリル基を有するポリ(アクリル酸n−ブチル)(以下、重合体1という)の混合物を得た。この混合液中のN,N−ジメチルアセトアミドを減圧留去した後、残さにトルエンを加えて、不溶分をろ過により除去した。濾液のトルエンを減圧留去して、重合体1を精製した。精製後の重合体1の重量平均分子量は32308、分散度は1.36、平均末端アクリル基数は2.0(即ち、末端へのアクリル基の導入率は100%)であった。
二液型硬化性樹脂組成物を調製するために下記成分を準備した。(以下、二液型硬化性樹脂組成物を組成物と表記する。)
(A)成分:(メタ)アクリルモノマーを重合させた主骨格を有し、主骨格の末端に(メタ)アクリル基を有するオリゴマー
・重合体1(製造例1により合成されたオリゴマー)
(B)成分:脂環骨格を有する(メタ)アクリルモノマー
・イソボルニルアクリレート(共栄社化学株式会社製 ライトアクリレートIB−XA)
・ジシクロペンタニルアクリレート(日立化成工業株式会社製 ファンクリルFA−513AS)
(B')成分:(B)成分ではない(メタ)アクリルモノマー
・アクリルモルホリン(株式会社興人製 ACMO)
・イソデシルアクリレート(サートマー社製 SR395)
(C)成分: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(日油株式会社製 パークミルH−80)
(D)成分:銅化合物および/またはバナジウム化合物
・ナフテン酸銅(日本化学産業株式会社製 ナフテックス銅)
・五酸化バナジウム(東京化成工業株式会社製 試薬)
(E)成分:サッカリン
・サッカリン(大和化成株式会社製 試薬)
(F)成分:パラフィン
・融点が42〜44℃のパラフィン(関東化学株式会社製 試薬)以下、パラフィンAと呼ぶ。)
・融点が44〜46℃のパラフィン(関東化学株式会社製 試薬)以下、パラフィンBと呼ぶ。)
・融点が46〜48℃のパラフィン(関東化学株式会社製 試薬)以下、パラフィンCと呼ぶ。)
・融点が48〜50℃のパラフィン(関東化学株式会社製 試薬)以下、パラフィンDと呼ぶ。)
・融点が50〜52℃のパラフィン(関東化学株式会社製 試薬)以下、パラフィンEと呼ぶ。)
・融点が63℃のパラフィンワックス(日本精蝋株式会社製 SP−0145)
(F')成分:(F)成分以外の可塑剤
・融点が40℃のα−オレフィンポリマー(エルクリスタC−4100 出光興産株式会社製)
・融点が76℃の1,2−ヒドロキシステアリン酸(伊藤製油株式会社製 T−3973)
・脂肪酸アミド変性体(融点:115℃)(伊藤製油株式会社製 A−S−A T−1700)
・脂肪酸アミド変性体(融点125℃)(伊藤製油株式会社製 A−S−A T−1800)
・ヒマシ油の水素添加物(融点86℃)(伊藤製油株式会社製 ヒマシ硬化油 T−3972)
・1,2−ヒドロキシステアリン酸(融点:130℃)(伊藤製油株式会社製 セバシン酸TA)
(G)成分:チオール基を有する化合物
・トリス−[(3−メルカプトプロピオニルオキシ)−エチル]−イソシアヌレート(堺化学工業株式会社製 TEMPIC)
その他
・2,2−ビス[4−(メタアクリロキシエトキシ)フェニル]プロパン(新中村化学工業株式会社製 NKエステル BPE−80N)
・ジメチルジクロロシランで疎水処理したヒュームドシリカ(日本アエロジル株式会社製 アエロジルR972)
・N,N−ジメチル−p−トルイジン(株式会社三星科学研究所製 試薬)
[A剤の調整方法]
(A)〜(C)成分および(F)成分(比較例の場合は、(B')成分と(F')成分を使用する。)を秤量し、30分間撹拌した。次にその他成分を秤量してさらに30分間撹拌した。詳細な調製量は表1と表2に従い、数値は全て質量部で表記する。
A剤とB剤をそれぞれ調整した後、所定の混合比率(A剤:B剤=1:1(質量比))になる様にA剤とB剤を同じ容器に秤量して素早く撹拌する。
直径50mm×厚さ5mmの円筒状の硬化物を作成するため、型に組成物を流し込んで25℃雰囲気下で24時間放置する。表面硬化状態の確認は、以下の四段階で硬化物表面の指触により行う。「◎」、「○」または「△」である事が好ましく、より好ましくは「◎」または「○」である。その結果を表3にまとめた。
○:べとべと感が無い
△:少しべとべとする
×:触ると糸を引く
[モノマー溶解性の確認]
(B)成分(または(B')成分)と(F)成分(または(F')成分)のみの混合物を別途作成し、(F)成分の(B)成分に対する溶解性を確認した。混合比率は表1と表2の(B)成分と(F)成分に従う。確認は以下の三段階で目視により確認を行う。本発明においては「○」または「△」であることが好ましく、より好ましくは「○」である。「×」の場合は組成物を保存する際に析出する恐れがある。その結果を表3にまとめた。ただし、比較例1は(F)成分(または(F')成分)を添加していないので「−」で示す。
△:完全に溶解するが24時間放置すると析出する
×:完全に溶解するが数時間で析出する、または全く溶解しない
組成物の厚さが2mmとなるように設定した治具へ、A剤とB剤を混合後直ちに流し込み、組成物の厚さが均一になるように離型フィルムを貼り合わせた後、25℃で24時間放置してシート状の硬化物を作成する。シート状硬化物を6mm以上となるように重ね、A型デュロメータ(硬度計)の加圧面をシート状硬化物に対して平行に保ちながら、衝撃を伴うことなく速やかに10Nの力で押しつけ、加圧面と試料とを密着させる。測定時に最大値を読み取り、最大値を「硬度(単位無し)」とし、硬化物そのものの柔らかさの指標とする。詳細はJIS K 6253−3:2012に従う。硬度としては、40以上が好ましい。
組成物の厚さが2mmとなるように設定した治具へ、A剤とB剤を混合後直ちに流し込み、組成物の厚さが均一になるように離型フィルムを貼り合わせた後、25℃で24時間放置して、シート状の硬化物を作成する。3号ダンベルで打ち抜いてテストピースを作製する。テストピースの長軸とチャックの中心が一直線になる様に、テストピースの両端をチャックに固定する。引張速度50mm/minでテストピースを引張り、最大荷重を測定する。当該最大荷重時の強度を「引張強さ(MPa)」とし、硬化物そのものの強さを数値化する。詳細はJIS K 6850:1999に従う。引張強さとしては、2.0MPa以上有することが好ましい。
組成物の厚さが2mmとなるように設定した治具へ、A剤とB剤を混合後直ちに流し込み、嫌気状態にて25℃で24時間放置して、シート状の硬化物を作成する。3号ダンベルで打ち抜いてテストピースを作製し、25mm間隔の標線をテストピースに記入する。引張剪断強さの測定と同じ容量でチャックに固定して、引張速度500mm/minによって試験片の切断に至るまで引っ張る。測定時にテストピースが伸びて標線の間隔の広がるため、テストピースが切断されるまでノギスにより標線の間隔を計測する。初期の標線間隔を基準として、伸びた割合を「伸び率(%)」とし、硬化物そのものの可撓性の指標とする。膨張収縮に追従するためには伸び率が100%以上有することが好ましい。
被着体を鉄(SPCC,SD)同士にした時の剪断接着強さを剪断接着強さ1とし、被着体をステンレス(SUS−304)同士にした時の剪断接着強さを剪断接着強さ2とする。それぞれの被着体は幅25mm×長さ100mm×厚さ2mmのものを用いて、接着面積を25mm×10mmとしてテストピースを作成し、25℃で24時間放置する。万能試験機により最大荷重時の強度を「剪断接着強さ(MPa)」とし、被着体に対する接着力の指標とする。詳細は、JIS K 6850:1999に従う。剪断接着強さとしては、5.0MPa以上有することが好ましい。
組成物の厚さが2mmとなるように設定した治具へ、A剤とB剤を混合後直ちに流し込み、組成物の厚さが均一になるように離型フィルムを貼り合わせた後、25℃で24時間放置して、シート状の硬化物を作成する。幅10mmの短冊状に打ち抜き、テストピースを作製する。DMA(動的粘弾性測定)装置に取り付け、貯蔵弾性率、損失弾性率、tanδを測定する。損失弾性率の極大値における温度を「ガラス転移点(℃)」とする。
Claims (6)
- (A)〜(G)成分を含む二液型硬化性樹脂組成物。
(A)成分:(メタ)アクリルモノマーを重合させた主骨格を有し、主骨格の末端に(メタ)アクリル基を有するオリゴマー
(B)成分:脂環骨格を有する(メタ)アクリルモノマー
(C)成分:ハイドロパーオキサイド
(D)成分:銅化合物およびバナジウム化合物の少なくとも一種
(E)成分:サッカリン
(F)成分:パラフィン
(G)成分:分子中に2〜6のチオール基を有する化合物 - 融点が40〜55℃の(F)成分を含む請求項1に記載の二液型硬化性樹脂組成物。
- 組成物全体に対して、前記(F)成分を0.7〜6.0質量%含む請求項1または2のいずれかに記載の二液型硬化性樹脂組成物。
- 前記(A)成分100質量部に対して、前記(G)成分を0.001〜5.0質量部含む請求項1〜3のいずれか1項に記載の二液型硬化性樹脂組成物。
- 前記(A)成分100質量部に対して、前記(G)成分を0.001〜2.0質量部含む請求項1〜4のいずれか1項に記載の二液型硬化性樹脂組成物。
- 一部の前記(A)成分、一部の前記(B)成分および前記(C)成分を含む製剤と、残りの前記(A)成分、残りの前記(B)成分、前記(D)〜(E)成分および前記(G)成分を含む製剤とからなり、前記(F)成分はいずれかまたは両方の製剤に含まれる、請求項1〜5のいずれかに記載の二液型硬化性樹脂組成物。
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