JP6795037B2 - チオール化合物で変性したジアリルフタレート樹脂、及び当該樹脂を含有する光硬化性樹脂組成物とその用途 - Google Patents
チオール化合物で変性したジアリルフタレート樹脂、及び当該樹脂を含有する光硬化性樹脂組成物とその用途 Download PDFInfo
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- JP6795037B2 JP6795037B2 JP2018538326A JP2018538326A JP6795037B2 JP 6795037 B2 JP6795037 B2 JP 6795037B2 JP 2018538326 A JP2018538326 A JP 2018538326A JP 2018538326 A JP2018538326 A JP 2018538326A JP 6795037 B2 JP6795037 B2 JP 6795037B2
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- JP
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- Prior art keywords
- thiol
- diallyl phthalate
- modified
- resin
- phthalate resin
- 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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- -1 thiol compound Chemical class 0.000 title claims description 123
- 239000011347 resin Substances 0.000 title claims description 115
- 229920005989 resin Polymers 0.000 title claims description 115
- 239000011342 resin composition Substances 0.000 title claims description 56
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 title description 6
- QUDWYFHPNIMBFC-UHFFFAOYSA-N bis(prop-2-enyl) benzene-1,2-dicarboxylate Chemical compound C=CCOC(=O)C1=CC=CC=C1C(=O)OCC=C QUDWYFHPNIMBFC-UHFFFAOYSA-N 0.000 claims description 88
- 239000004641 Diallyl-phthalate Substances 0.000 claims description 73
- 150000001875 compounds Chemical class 0.000 claims description 37
- 239000003999 initiator Substances 0.000 claims description 17
- 239000003973 paint Substances 0.000 claims description 15
- 239000000463 material Substances 0.000 claims description 13
- 239000002966 varnish Substances 0.000 claims description 7
- 239000011248 coating agent Substances 0.000 claims description 6
- 238000000576 coating method Methods 0.000 claims description 6
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Divinylene sulfide Natural products C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 30
- 238000005481 NMR spectroscopy Methods 0.000 description 24
- 238000004519 manufacturing process Methods 0.000 description 23
- 239000000976 ink Substances 0.000 description 22
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 16
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 15
- 239000004743 Polypropylene Substances 0.000 description 15
- 229920001155 polypropylene Polymers 0.000 description 15
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 14
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- 229920003023 plastic Polymers 0.000 description 12
- 239000004033 plastic Substances 0.000 description 12
- 150000003573 thiols Chemical class 0.000 description 12
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 10
- 239000000203 mixture Substances 0.000 description 9
- 238000012986 modification Methods 0.000 description 9
- 230000004048 modification Effects 0.000 description 9
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 8
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 8
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 8
- PYGSKMBEVAICCR-UHFFFAOYSA-N hexa-1,5-diene Chemical group C=CCCC=C PYGSKMBEVAICCR-UHFFFAOYSA-N 0.000 description 8
- 229910052740 iodine Inorganic materials 0.000 description 8
- 239000011630 iodine Substances 0.000 description 8
- 238000001723 curing Methods 0.000 description 7
- 238000011156 evaluation Methods 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- 239000003505 polymerization initiator Substances 0.000 description 7
- QNODIIQQMGDSEF-UHFFFAOYSA-N (1-hydroxycyclohexyl)-phenylmethanone Chemical compound C=1C=CC=CC=1C(=O)C1(O)CCCCC1 QNODIIQQMGDSEF-UHFFFAOYSA-N 0.000 description 6
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- 238000001035 drying Methods 0.000 description 6
- 238000005227 gel permeation chromatography Methods 0.000 description 6
- 238000005259 measurement Methods 0.000 description 6
- 229920000139 polyethylene terephthalate Polymers 0.000 description 6
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- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 5
- 239000000654 additive Substances 0.000 description 5
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- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 description 5
- WMYINDVYGQKYMI-UHFFFAOYSA-N 2-[2,2-bis(hydroxymethyl)butoxymethyl]-2-ethylpropane-1,3-diol Chemical compound CCC(CO)(CO)COCC(CC)(CO)CO WMYINDVYGQKYMI-UHFFFAOYSA-N 0.000 description 4
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- 235000008411 Sumatra benzointree Nutrition 0.000 description 4
- 239000000853 adhesive Substances 0.000 description 4
- 230000001070 adhesive effect Effects 0.000 description 4
- 125000002947 alkylene group Chemical group 0.000 description 4
- 229960002130 benzoin Drugs 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 125000000524 functional group Chemical group 0.000 description 4
- 235000019382 gum benzoic Nutrition 0.000 description 4
- 239000000178 monomer Substances 0.000 description 4
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 4
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- 238000012719 thermal polymerization Methods 0.000 description 4
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- SUODCTNNAKSRHB-UHFFFAOYSA-N 2-ethylhexyl 3-sulfanylpropanoate Chemical compound CCCCC(CC)COC(=O)CCS SUODCTNNAKSRHB-UHFFFAOYSA-N 0.000 description 3
- 108700028369 Alleles Proteins 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- NQHAZTDQFIYTQD-UHFFFAOYSA-N SOS Chemical compound SOS NQHAZTDQFIYTQD-UHFFFAOYSA-N 0.000 description 3
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 3
- 239000007983 Tris buffer Substances 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 125000005396 acrylic acid ester group Chemical group 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 125000005233 alkylalcohol group Chemical group 0.000 description 3
- 239000012965 benzophenone Substances 0.000 description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
- UENWRTRMUIOCKN-UHFFFAOYSA-N benzyl thiol Chemical compound SCC1=CC=CC=C1 UENWRTRMUIOCKN-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- ZDNFTNPFYCKVTB-UHFFFAOYSA-N bis(prop-2-enyl) benzene-1,4-dicarboxylate Chemical compound C=CCOC(=O)C1=CC=C(C(=O)OCC=C)C=C1 ZDNFTNPFYCKVTB-UHFFFAOYSA-N 0.000 description 3
- MQDJYUACMFCOFT-UHFFFAOYSA-N bis[2-(1-hydroxycyclohexyl)phenyl]methanone Chemical compound C=1C=CC=C(C(=O)C=2C(=CC=CC=2)C2(O)CCCCC2)C=1C1(O)CCCCC1 MQDJYUACMFCOFT-UHFFFAOYSA-N 0.000 description 3
- WQAQPCDUOCURKW-UHFFFAOYSA-N butanethiol Chemical compound CCCCS WQAQPCDUOCURKW-UHFFFAOYSA-N 0.000 description 3
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 3
- HDFRDWFLWVCOGP-UHFFFAOYSA-N carbonothioic O,S-acid Chemical compound OC(S)=O HDFRDWFLWVCOGP-UHFFFAOYSA-N 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 3
- WNAHIZMDSQCWRP-UHFFFAOYSA-N dodecane-1-thiol Chemical compound CCCCCCCCCCCCS WNAHIZMDSQCWRP-UHFFFAOYSA-N 0.000 description 3
- 235000011187 glycerol Nutrition 0.000 description 3
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 3
- 229910052753 mercury Inorganic materials 0.000 description 3
- 150000002978 peroxides Chemical class 0.000 description 3
- 229920002120 photoresistant polymer Polymers 0.000 description 3
- 229920006295 polythiol Polymers 0.000 description 3
- SUVIGLJNEAMWEG-UHFFFAOYSA-N propane-1-thiol Chemical compound CCCS SUVIGLJNEAMWEG-UHFFFAOYSA-N 0.000 description 3
- 239000003381 stabilizer Substances 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 3
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical compound C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 description 2
- YAJYJWXEWKRTPO-UHFFFAOYSA-N 2,3,3,4,4,5-hexamethylhexane-2-thiol Chemical compound CC(C)C(C)(C)C(C)(C)C(C)(C)S YAJYJWXEWKRTPO-UHFFFAOYSA-N 0.000 description 2
- UCJMHYXRQZYNNL-UHFFFAOYSA-N 2-Ethyl-1-hexanethiol Chemical compound CCCCC(CC)CS UCJMHYXRQZYNNL-UHFFFAOYSA-N 0.000 description 2
- KMNCBSZOIQAUFX-UHFFFAOYSA-N 2-ethoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OCC)C(=O)C1=CC=CC=C1 KMNCBSZOIQAUFX-UHFFFAOYSA-N 0.000 description 2
- PMNLUUOXGOOLSP-UHFFFAOYSA-N 2-mercaptopropanoic acid Chemical compound CC(S)C(O)=O PMNLUUOXGOOLSP-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
- ZMRFRBHYXOQLDK-UHFFFAOYSA-N 2-phenylethanethiol Chemical compound SCCC1=CC=CC=C1 ZMRFRBHYXOQLDK-UHFFFAOYSA-N 0.000 description 2
- 229920000298 Cellophane Polymers 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- VPIAKHNXCOTPAY-UHFFFAOYSA-N Heptane-1-thiol Chemical compound CCCCCCCS VPIAKHNXCOTPAY-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
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- 239000004793 Polystyrene Substances 0.000 description 2
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- 238000003848 UV Light-Curing Methods 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
- 150000008062 acetophenones Chemical class 0.000 description 2
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- 229910052736 halogen Inorganic materials 0.000 description 2
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- YNSNJGRCQCDRDM-UHFFFAOYSA-N 1-chlorothioxanthen-9-one Chemical class S1C2=CC=CC=C2C(=O)C2=C1C=CC=C2Cl YNSNJGRCQCDRDM-UHFFFAOYSA-N 0.000 description 1
- OBNIRVVPHSLTEP-UHFFFAOYSA-N 1-ethoxy-2-(2-hydroxyethoxy)ethanol;prop-2-enoic acid Chemical compound OC(=O)C=C.CCOC(O)COCCO OBNIRVVPHSLTEP-UHFFFAOYSA-N 0.000 description 1
- NUGJYPZRNLPNDM-UHFFFAOYSA-N 16-methylheptadecane-1-thiol Chemical compound CC(C)CCCCCCCCCCCCCCCS NUGJYPZRNLPNDM-UHFFFAOYSA-N 0.000 description 1
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- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F18/00—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 an acyloxy radical of a saturated carboxylic acid, of carbonic acid or of a haloformic acid
- C08F18/14—Esters of polycarboxylic acids
- C08F18/16—Esters of polycarboxylic acids with alcohols containing three or more carbon atoms
- C08F18/18—Diallyl phthalate
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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
- C08L31/00—Compositions of homopolymers or 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 an acyloxy radical of a saturated carboxylic acid, of carbonic acid or of a haloformic acid; Compositions of derivatives of such polymers
- C08L31/06—Homopolymers or copolymers of esters of polycarboxylic acids
- C08L31/08—Homopolymers or copolymers of esters of polycarboxylic acids of phthalic acid
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- C09D11/00—Inks
- C09D11/02—Printing inks
- C09D11/10—Printing inks based on artificial resins
- C09D11/101—Inks specially adapted for printing processes involving curing by wave energy or particle radiation, e.g. with UV-curing following the printing
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- C09D147/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds; Coating compositions based on derivatives of such polymers
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- 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
- C09D4/00—Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16
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Description
また、この光硬化性樹脂組成物は、特にPP(ポリプロピレン)樹脂に対する密着性に優れる。
これは、ジアリルフタレート樹脂のペンダントアリル基をチオール化合物で変性させることによって、ジアリルフタレート樹脂の極性が低下し、PP樹脂の極性に近づくことで、PP樹脂に対しての密着性の観点で好ましい組み合わせとなっているためと考えられる。
そのため、従来のジアリルフタレート樹脂を用いた組成物では、密着性を高くすることが困難であったPP樹脂用のインキ、塗料の成分として適している。
また、チオール化合物で変性したジアリルフタレート樹脂は、従来のジアリルフタレート樹脂が相溶しない極性の低いエチレン性不飽和化合物との相溶性が良い組成物を構成することができる。
本発明におけるチオール化合物で変性したジアリルフタレート樹脂は、ジアリルフタレート樹脂のペンダントアリル基とチオール化合物をエンチオール反応させることによって、変性させたものであれば、特に制限なく用いることができる。
変性(エンチオール反応)に用いるチオール化合物は、ジアリルフタレート樹脂のペンダントアリル基と反応できるものであれば特に問題なく、用いることができる。例えば、脂肪族チオール化合物、芳香族チオール化合物、脂肪族ポリチオール化合物、メルカプトカルボン酸エステル化合物、メルカプトカルボン酸、メルカプトエーテルを例示することができる。
エンチオール反応は、不飽和化合物(アリル化合物やジアリルフタレート樹脂等)とチオール化合物とを接触させることにより進行するが、通常、アリル化合物及びチオール化合物を含む反応系に、活性エネルギー(又は活性エネルギー線)を付与することにより反応(エンチオール反応)させてもよい。活性エネルギーの付与により、容易にエンチオール反応を進行させることができる。
本明細書において、チオール化合物で変性したジアリルフタレート樹脂の重量平均分子量(Mw)、数平均分子量(Mn)は実施例に記載の方法により測定される値である。
本発明の光硬化性樹脂組成物は、硬化前の樹脂組成物であり、少なくとも上述したチオール化合物で変性したジアリルフタレート樹脂を含有する組成物である。
本発明の光硬化性樹脂組成物は、光照射により硬化可能であるエチレン性不飽和化合物を含有することが好ましい。エチレン性不飽和化合物は、炭素−炭素二重結合を1〜20個有することが好ましく、1〜10個有することがより好ましく、1〜6個有することがさらに好ましい。エチレン性不飽和化合物としては、(メタ)アクリル酸エステル化合物、(メタ)アリル化合物及びビニル化合物等が挙げられる。また、エチレン性不飽和化合物は2種以上の化合物の混合物を用いることも可能である。
ビニル化合物としては、スチレン、ジビニルベンゼン、N-ビニルピロリドン、酢酸ビニル等を例示することができる。
本発明の光硬化性樹脂組成物は、重合開始剤を含んでいてもよく、特に光重合開始剤を含有することが好ましい。光硬化性樹脂組成物に含有される光重合開始剤としては、2−メチル−1−[4−(メチルチオ)フェニル]−2−モルホリノプロパン−1、1−ヒドロキシシクロヘキシルフェニルケトン等のアセトフェノン系、ベンゾイン、ベンゾインエチルエーテル等のベンゾイン系、ベンゾフェノン等のベンゾフェノン系、アシルフォスフィンオキサイド等のリン系、チオキサントン等のイオウ系、ベンジル、9,10−フェナンスレンキノン等のジベンジル系が挙げられる。
光開始助剤の量は、光硬化性樹脂組成物全体に対して、0.1〜5重量%の範囲であることが好ましく、0.5〜3重量%の範囲がより好ましい。
また、オーバープリントワニスの作成は、顔料を使用しない以外は、インキと同様の手順により行える。
以下、実施例を挙げて、本発明をより具体的に説明するが、本発明はこれらの実施例に限定されるものではない。
後述するチオール化合物で変性したジアリルフタレート樹脂、製造に用いたジアリルフタレート樹脂の分析は、下記に記載の方法を用いて行った。
重量平均分子量(Mw)、分子量分布(Mw/Mn)はGPCを用いて測定した。標準ポリスチレン換算の重量平均分子量、数平均分子量の値である。
カラム:2つのShodexLF−804を直列に接続
流速:1.0mL/min
温度:40℃
検出器:RID−20A
試料:試料50mgをテトラヒドロフラン5mLに溶解させ測定用のサンプルとした。
製造に用いたジアリルフタレート樹脂、光重合開始剤、チオール化合物、得られたチオール変性ジアリルフタレート樹脂の各NMR測定は、1H NMR(500MHz,CDCl3中)で測定した。測定した各NMRスペクトルを図1〜3に示す。
製造に用いたジアリルフタレート樹脂のヨウ素価は、JIS K6235に定める方法に従って測定した。
撹拌子を入れた200mLのセパラブルフラスコにメチルエチルケトン20gを加え、撹拌しながらジアリルフタレート樹脂((株)大阪ソーダ製;ダイソーイソダップ:MW4.1万)4gを添加し、25℃、60分攪拌し溶解させた。ここに、3−メルカプトプロピオン酸2‐エチルヘキシル(和光純薬工業社製)2.8g、光重合開始剤(Irgacure 184)118mgを加え、10分撹拌し溶解した。25℃で撹拌しながら、光照射装置(LIGHTNINGCURE LC6 モデルL8858−01 浜松ホトニクス製、ランプ種類:水銀キセノンランプ 中心波長365nm 放射波長:300nm〜450nm)を用いて、60秒間照射してエンチオール反応を行った。なお、積算光量測定は、アイ紫外線積算照度計:UVPF−A1 受光器:PD−365(アイグラフィックス製)を用いて行った。測定値は、60秒で、6100mJ/cm2であった。ロータリーエバポレーターを用いて反応後の溶液を2倍濃縮した。得られた反応溶液を撹拌下のメタノール400mLに添加し、樹脂を沈殿させた。沈殿した固体を、40℃で真空乾燥を6時間行い、チオール化合物で変性したジアリルフタレート樹脂(樹脂1)を得た。得られたチオール変性ジアリルフタレート樹脂のNMR測定、GPC測定を行った(収量:5.1g,Mw=6.5万,Mw/Mn=4.1)。チオール変性ジアリルフタレート樹脂のペンダントアリル基のチオール変性率はアリル基を示す5.9ppmのNMRピーク積分値(反応前のジアリルフタレート樹脂のNMRピーク積分値(41.1545)−反応後のチオール変性ジアリルフタレート樹脂のNMRピーク積分値(1.7548))÷反応前のジアリルフタレート樹脂のNMRピーク積分値(41.1545)より算出し、95.7%のアリル基が変性されていた。NMRを図1に示す。
製造例1のチオール化合物を1−ドデカンチオール(2.7g)に変更した以外は同様の方法で行い、チオール化合物で変性したジアリルフタレート樹脂(樹脂2)を得た。得られたチオール変性ジアリルフタレート樹脂のNMR測定、GPC測定を行った(収量:4.1g,Mw=4.4万,Mw/Mn=4.8)。チオール変性ジアリルフタレート樹脂のペンダントアリル基のチオール変性率はアリル基を示す5.9ppmのNMRピーク積分値(反応前のジアリルフタレート樹脂のNMRピーク積分値(42.6445)−反応後のチオール変性ジアリルフタレート樹脂のNMRピーク積分値(3.7247))÷反応前のジアリルフタレート樹脂のNMRピーク積分値(42.6445)より算出し、90.9%のアリル基が変性されていた。NMRを図2に示す。
製造例1のチオール化合物を2−エチルヘキサンチオール(1.8g)に変更した以外は同様の方法で行い、チオール化合物で変性したジアリルフタレート樹脂(樹脂3)を得た。得られたチオール変性ジアリルフタレート樹脂のNMR測定、GPC測定を行った(収量:4.9g,Mw=3.9万,Mw/Mn=3.6)。チオール変性ジアリルフタレート樹脂のペンダントアリル基のチオール変性率はアリル基を示す5.9ppmのNMRピーク積分値(反応前のジアリルフタレート樹脂のNMRピーク積分値(53.1886)−反応後のチオール変性ジアリルフタレート樹脂のNMRピーク積分値(6.7295))÷反応前のジアリルフタレート樹脂のNMRピーク積分値(53.1886)より算出し、87.3%のアリル基が変性されていた。NMRを図3に示す。
下記表1に記載の各組成の光硬化性樹脂組成物を調製し、光硬化性樹脂組成物の特性を評価した。
また、表1に示す組成量は重量部である。
樹脂1;製造例1で得られた変性ジアリルフタレート樹脂
樹脂2;製造例2で得られた変性ジアリルフタレート樹脂
樹脂3;製造例3で得られた変性ジアリルフタレート樹脂
DAP樹脂;(株)大阪ソーダ製 ダイソーイソダップ(ジアリルイソフタレート樹脂;Mw=4.1万、Mw/Mn=4.1、ヨウ素価=80)
DPGDA;ジプロピレングリコールジアクリレート(新中村化学工業(株)製)
Irgacure184(BASFジャパン(株)製の1−ヒドロキシシクロヘキシルフェニルケトン)
樹脂とエチレン性化合物(2−エチルヘキシルアクリレート)=30:70となるように添加し、100℃に加熱混合して光硬化性樹脂組成物を調製した。室温に冷却後、1日経過したものの外観が透明であるかで溶解性を確認した。冷却後も外観が透明であったものを〇、白濁したものを×とした。結果は表2に示す。
調製した各光硬化性樹脂組成物100重量部に対して光重合開始剤としてIrgacure184(BASFジャパン(株)製)を10重量部添加し、加熱混合することで速乾性の評価に用いるサンプルを調製した。
プラスチック基材(ポリプロピレン基材:東洋紡株式会社製 二軸延伸フィルム 品名:パイレンフィルム-OT P2161 厚み50μm)に、密着性試験に用いるために調製した上記サンプルをワイヤーバー(コーティングロッド)を用いてコートし、出力160W/cmのメタルハライドランプ(ランプ距離14cm、光量約200mW/cm2で塗膜がタックフリーになるまでの時間光照射)で硬化させた。なお、UV硬化装置はウシオ電機製ボックス型紫外線硬化装置を用いた。得られた塗膜を指触することで速乾性を確認した。積算光量4456mJ/cm2未満で硬化したものを○、積算光量4456mJ/cm2以上で硬化したものを×とした。評価結果を表2に示す。
調製した光硬化性樹脂組成物を、速乾性試験と同様の方法でプラスチックフィルムにコートし、硬化させた。得られた塗膜に、ニチバン社製24mm幅のセロテープ(登録商標)(品番:CT−24、粘着力:4.01N/10mm)を貼り付け、親指で5回強く擦った後、セロテープ(登録商標)を引き離した。評価基準は下記の通りとした。評価結果を表2に示す。
5:素早くテープを剥離した場合に、硬化膜が剥離しない。
4:素早くテープを剥離した場合に、硬化膜が50%剥離する。
3:ゆっくりテープを剥離した場合に、硬化膜が剥離しない。
2:ゆっくりテープを剥離した場合に、硬化膜が50%剥離する。
1:ゆっくりテープを剥離した場合に、硬化膜が完全に剥離する。
調製した光硬化性樹脂組成物を使用し、速乾性試験と同様の方法でサンプル調整した。Thermo Fisher SCIENTIFC HAAKE MARS3を用いて30℃での粘度を測定した。評価結果を表2に示す。
Claims (5)
- 脂肪族チオール化合物、メルカプトカルボン酸エステル化合物、のいずれかのチオール化合物で変性したことを特徴とするジアリルフタレート樹脂と、
エチレン性不飽和化合物とを含有し、
前記チオール化合物が、モノチオール化合物である光硬化性樹脂組成物。 - 更に、光重合開始剤を含有する請求項1に記載の光硬化性樹脂組成物。
- 請求項1又は2に記載の光硬化性樹脂組成物を含有するインキ。
- 請求項1又は2に記載の光硬化性樹脂組成物を含有する塗料。
- オーバープリントワニスである請求項4に記載の塗料。
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