JPWO2017170388A1 - 光硬化性樹脂組成物、インキ及び塗料 - Google Patents
光硬化性樹脂組成物、インキ及び塗料 Download PDFInfo
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- JPWO2017170388A1 JPWO2017170388A1 JP2018507982A JP2018507982A JPWO2017170388A1 JP WO2017170388 A1 JPWO2017170388 A1 JP WO2017170388A1 JP 2018507982 A JP2018507982 A JP 2018507982A JP 2018507982 A JP2018507982 A JP 2018507982A JP WO2017170388 A1 JPWO2017170388 A1 JP WO2017170388A1
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- Prior art keywords
- resin composition
- photocurable resin
- allyl
- weight
- ink
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- 239000011342 resin composition Substances 0.000 title claims abstract description 63
- 239000003973 paint Substances 0.000 title claims description 18
- 239000000976 ink Substances 0.000 title description 39
- -1 allyl compound Chemical class 0.000 claims abstract description 52
- 229920000642 polymer Polymers 0.000 claims abstract description 40
- 239000003349 gelling agent Substances 0.000 claims abstract description 33
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims abstract description 31
- 125000006841 cyclic skeleton Chemical group 0.000 claims abstract description 14
- 230000000379 polymerizing effect Effects 0.000 claims abstract description 10
- 229920006395 saturated elastomer Polymers 0.000 claims abstract description 4
- 125000001424 substituent group Chemical group 0.000 claims abstract description 4
- 150000001875 compounds Chemical class 0.000 claims description 34
- 239000002966 varnish Substances 0.000 claims description 22
- 239000011248 coating agent Substances 0.000 claims description 4
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- 239000000463 material Substances 0.000 claims description 4
- 239000000203 mixture Substances 0.000 abstract description 12
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- 229920005989 resin Polymers 0.000 abstract description 11
- 239000000126 substance Substances 0.000 abstract description 3
- 238000003860 storage Methods 0.000 description 17
- 229910052782 aluminium Inorganic materials 0.000 description 15
- 238000007639 printing Methods 0.000 description 13
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 12
- 239000003999 initiator Substances 0.000 description 11
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- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 8
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 8
- 238000000034 method Methods 0.000 description 8
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- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical class C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 7
- 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 description 7
- 238000005259 measurement Methods 0.000 description 7
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- XRMBQHTWUBGQDN-UHFFFAOYSA-N [2-[2,2-bis(prop-2-enoyloxymethyl)butoxymethyl]-2-(prop-2-enoyloxymethyl)butyl] prop-2-enoate Chemical compound C=CC(=O)OCC(COC(=O)C=C)(CC)COCC(CC)(COC(=O)C=C)COC(=O)C=C XRMBQHTWUBGQDN-UHFFFAOYSA-N 0.000 description 6
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- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 description 3
- 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 3
- 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 3
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 3
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- 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
- 238000006243 chemical reaction Methods 0.000 description 3
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- 239000000178 monomer Substances 0.000 description 3
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 3
- 238000003756 stirring Methods 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
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-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
- 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
- HHCHLHOEAKKCAB-UHFFFAOYSA-N 2-oxaspiro[3.5]nonane-1,3-dione Chemical compound O=C1OC(=O)C11CCCCC1 HHCHLHOEAKKCAB-UHFFFAOYSA-N 0.000 description 2
- HFSHGXIPMHQUFT-UHFFFAOYSA-N 3,8-dihydroxy-2-(hydroxymethyl)-7-methylnon-1-en-4-one Chemical compound CC(O)C(C)CCC(=O)C(O)C(=C)CO HFSHGXIPMHQUFT-UHFFFAOYSA-N 0.000 description 2
- OSDWBNJEKMUWAV-UHFFFAOYSA-N Allyl chloride Chemical compound ClCC=C OSDWBNJEKMUWAV-UHFFFAOYSA-N 0.000 description 2
- 239000004342 Benzoyl peroxide Substances 0.000 description 2
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-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
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
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- 125000005396 acrylic acid ester group Chemical group 0.000 description 2
- ORILYTVJVMAKLC-UHFFFAOYSA-N adamantane Chemical compound C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
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- 235000019400 benzoyl peroxide Nutrition 0.000 description 2
- ZXTPJLLIHIDBKQ-UHFFFAOYSA-N bis(prop-2-enyl) cyclohexane-1,4-dicarboxylate Chemical compound C=CCOC(=O)C1CCC(C(=O)OCC=C)CC1 ZXTPJLLIHIDBKQ-UHFFFAOYSA-N 0.000 description 2
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 2
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- BFQYHVSLZNFHTP-UHFFFAOYSA-N butan-1-olate pentane-2,4-dione zirconium(4+) Chemical compound [Zr+4].CCCC[O-].CCCC[O-].CCCC[O-].CCCC[O-].CC(=O)CC(C)=O BFQYHVSLZNFHTP-UHFFFAOYSA-N 0.000 description 2
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- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 2
- SSDSCDGVMJFTEQ-UHFFFAOYSA-N octadecyl 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)CCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 SSDSCDGVMJFTEQ-UHFFFAOYSA-N 0.000 description 2
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- 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 1
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- RDASHQZXQNLNMG-UHFFFAOYSA-N butan-2-olate;di(propan-2-yloxy)alumanylium Chemical compound CCC(C)O[Al](OC(C)C)OC(C)C RDASHQZXQNLNMG-UHFFFAOYSA-N 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
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- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000008094 contradictory effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 description 1
- OVHKECRARPYFQS-UHFFFAOYSA-N cyclohex-2-ene-1,1-dicarboxylic acid Chemical compound OC(=O)C1(C(O)=O)CCCC=C1 OVHKECRARPYFQS-UHFFFAOYSA-N 0.000 description 1
- QYQADNCHXSEGJT-UHFFFAOYSA-N cyclohexane-1,1-dicarboxylate;hydron Chemical compound OC(=O)C1(C(O)=O)CCCCC1 QYQADNCHXSEGJT-UHFFFAOYSA-N 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 239000012933 diacyl peroxide Substances 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- BEGAGPQQLCVASI-UHFFFAOYSA-N ethyl 2-hydroxypropanoate;titanium Chemical compound [Ti].CCOC(=O)C(C)O BEGAGPQQLCVASI-UHFFFAOYSA-N 0.000 description 1
- YRMWCMBQRGFNIZ-UHFFFAOYSA-N ethyl 3-oxobutanoate;zirconium Chemical compound [Zr].CCOC(=O)CC(C)=O YRMWCMBQRGFNIZ-UHFFFAOYSA-N 0.000 description 1
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 1
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- 150000002739 metals Chemical class 0.000 description 1
- ZQMHJBXHRFJKOT-UHFFFAOYSA-N methyl 2-[(1-methoxy-2-methyl-1-oxopropan-2-yl)diazenyl]-2-methylpropanoate Chemical compound COC(=O)C(C)(C)N=NC(C)(C)C(=O)OC ZQMHJBXHRFJKOT-UHFFFAOYSA-N 0.000 description 1
- MAQCMFOLVVSLLK-UHFFFAOYSA-N methyl 4-(bromomethyl)pyridine-2-carboxylate Chemical compound COC(=O)C1=CC(CBr)=CC=N1 MAQCMFOLVVSLLK-UHFFFAOYSA-N 0.000 description 1
- UMRZSTCPUPJPOJ-KNVOCYPGSA-N norbornane Chemical compound C1C[C@H]2CC[C@@H]1C2 UMRZSTCPUPJPOJ-KNVOCYPGSA-N 0.000 description 1
- JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical compound C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 description 1
- 238000007645 offset printing Methods 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
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- 229910052698 phosphorus Inorganic materials 0.000 description 1
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- 238000000016 photochemical curing Methods 0.000 description 1
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- XPGAWFIWCWKDDL-UHFFFAOYSA-N propan-1-olate;zirconium(4+) Chemical compound [Zr+4].CCC[O-].CCC[O-].CCC[O-].CCC[O-] XPGAWFIWCWKDDL-UHFFFAOYSA-N 0.000 description 1
- RLJWTAURUFQFJP-UHFFFAOYSA-N propan-2-ol;titanium Chemical compound [Ti].CC(C)O.CC(C)O.CC(C)O.CC(C)O RLJWTAURUFQFJP-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
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- 239000002904 solvent Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 150000003463 sulfur Chemical class 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- VXUYXOFXAQZZMF-UHFFFAOYSA-N tetraisopropyl titanate Substances CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 235000010215 titanium dioxide Nutrition 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000004034 viscosity adjusting agent Substances 0.000 description 1
- IPCAPQRVQMIMAN-UHFFFAOYSA-L zirconyl chloride Chemical compound Cl[Zr](Cl)=O IPCAPQRVQMIMAN-UHFFFAOYSA-L 0.000 description 1
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Abstract
本発明は、下記一般式(I)で表されるアリル系化合物を重合して得られるアリル系重合体(A)と、ゲル化剤(B)とを含有することを特徴とする光硬化性樹脂組成物に関する[一般式(I)中、R1およびR2は、それぞれ、HまたはCH3を表し、Xは置換基を有しない飽和または一部不飽和の4〜8員環の環状骨格であってa価の基を表し、aは2または3を表す。]。
[化1]
Description
すなわち、本発明の光硬化性樹脂組成物は、
下記一般式(I)で表されるアリル系化合物を重合して得られるアリル系重合体(A)と、ゲル化剤(B)とを含有することを特徴とする。
Xは置換基を有しない飽和または一部不飽和の4〜8員環の環状骨格であってa価の基を表し、aは2または3を表す。]
エチレン性不飽和化合物(C)を含有することにより、光硬化性樹脂組成物の乾燥性、得られる硬化物の皮膜強度が向上する、また、印刷に用いるのに適切な粘度に調整することができ、塗布作業性に優れた組成物が得られる。
このインキは、印刷適性に優れる。
また、本発明の塗料はオーバープリントワニスであることが好ましい。
このように、本発明では、アリル系重合体(A)と、ゲル化剤(B)とを併用することにより、良好な流動性及び/又は印刷応答性を得ることができ、印刷適性に優れ、インキ、塗料として好適に使用できる。
また、一般的に、流動性と印刷応答性は二律背反性能であるが、アリル系重合体(A)と、ゲル化剤(B)とを併用し、更にゲル化剤(B)としてアルミニウム錯体化合物を使用することにより、流動性と印刷応答性を両立でき、印刷適性により優れ、インキ、塗料としてより好適に使用できる。
なお、アリル系重合体(A)と、ゲル化剤(B)とを併用することにより、低周波数領域(0.01〜0.1Hz付近)での貯蔵弾性率を低減できることは驚くべき知見である。
本発明の光硬化性樹脂組成物は、下記一般式(I)で表されるアリル系化合物を重合して得られるアリル系重合体(A)を含有する。
Xは置換基を有しない飽和または一部不飽和の4〜8員環の環状骨格であってa価の基を表し、aは2または3を表す。]
また、上記一般式(I)で表されるアリル系化合物の具体例として挙げた化合物の市販品を用いてもよい。
本発明において、アリル系重合体(A)を含む光硬化性樹脂組成物に使用されるゲル化剤(B)としては、アリル系重合体(A)と共に使用することにより、擬似的に架橋鎖を形成できるものであれば特に限定されない。ゲル化剤(B)としては、例えば、アルミニウム錯体化合物を挙げる事ができ、環状アルミニウム化合物類、例えば環状アルミニウムオキサイドオクテート(川研ファインケミカル社製アルゴマー800)、環状アルミニウムオキサイドステアレート(川研ファインケミカル社製アルゴマー1000S)等、アルミニウムアルコキシド類としてアルミニウムエトキシド、アルミニウムイソプロポキシド(川研ファインケミカル社製AIPD) 、アルミニウム−sec−ブトキシド(川研ファインケミカル社製ASPD) 、アルミニウムジイソプロポキシドモノsec−ブトキシド(川研ファインケミカル社製AMD) 、アルミニウムアルキルアセテート類、例えばアルミニウム−ジ−n−ブトキシド−エチルアセトアセテート(ホープ製薬社製Chelope−Al−EB2)、アルミニウム−ジ−iso−ブトキシド−メチルアセトアセテート(ホープ製薬社製Chelope−Al−MB12)、アルミニウム−ジ−iso−ブトキシド−エチルアセトアセテート(ホープ製薬社製Chelope−Al−EB102)、アルミニウム−ジ−iso−ブトキシド−エチルアセトアセテート(ホープ製薬社製Chelope−Al−EB2)、アルミニウム−ジ−iso−プロポキシド−エチルアセトアセテート(ホープ製薬社製Chelope−Al−EP12、川研ファインケミカル社製ALCH)、アルミニウム−トリス(アセチルアセトナート)(川研ファインケミカル社製ALCH−TR) 、アルミニウム−トリス(アセチルアセトナート)(川研ファインケミカル社製アルミキレート−A) 、アルミニウム−ビス(エチルアセチルアセトナート)−モノアセチルアセトナート(川研ファインケミカル社製アルミキレートD) 、アルミキレートM(川研ファインケミカル社製)、アルミキレートNB−15(ホープ製薬社製)、ケロープS(ホープ製薬社製)ケロープACS−2(ホープ製薬社製、液状オリープAOO(ホープ製薬社製) 、液状オリープAOS( ホープ製薬社製) が例示される。アルミニウム石鹸としてアルミニウムステアレート(日油(株)製)、アルミニウムオレート、アルミニウムナフトネート、アルミニウムウレート、アルミニウムアセチルアセトネート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、光照射により硬化可能であるエチレン性不飽和化合物(C)を含有することが好ましい。エチレン性不飽和化合物(C)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、2〜6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(C)としては、(メタ)アクリル酸エステル化合物、(メタ)アリル化合物およ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−オン、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。
着色剤の量は、光硬化性樹脂組成物全体に対して、1〜50重量%の範囲であることが好ましく、1〜45重量%の範囲がより好ましい。
また、本発明の光硬化性樹脂組成物は、ゲル化剤(B)未配合の光硬化性樹脂組成物に比べて、ゲル化剤(B)を配合することにより、10Hz(高周波数領域)での貯蔵弾性率が、好ましくは120%以上、より好ましくは150%以上となることが好ましい。これにより、より良好な印刷応答性が得られる。
ここで、貯蔵弾性率は、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を含むインキは本発明のインキであり、本発明の光硬化性樹脂組成物を含む塗料は本発明の塗料である。また、本発明の塗料はオーバープリントワニスであることが好ましい。
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。
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の値である。
カラム:ShodexKF−806L、KF−804、KF−803、KF−802、KF−801を直列に接続
流速:1.0mL/min
温度:40℃
検出:RID−6A
試料:試料20mgをテトラヒドロフラン10mLに溶解させ測定用のサンプルとした。
1,2−シクロヘキサンジカルボン酸ジアリルは、シクロヘキサンジカルボン酸無水物とアリルアルコールをエステル化反応させることによって製造した。
3Lのセパラブルフラスコに1,2−シクロヘキサンジカルボン酸ジアリル2400gを加え、60gのベンゾイルパーオキサイドを加えて80℃で加熱撹拌した。2.5時間反応させた後、30℃まで冷却した。冷却後、フラスコにメタノールを加え、重合体を沈殿させた。得られた重合体を40℃で16時間減圧乾燥した(収量:408g、収率:17%、Mw=32,000、Mw/Mn=2.8)。得られた重合体を重合体1とした。
(1)ワニスの調製
樹脂(上記重合体1)35重量部、DTMPTA(SR−355NS:Sartomer社製のジトリメチロールプロパンテトラアクリレート)65重量部、重合禁止剤(IRGANOX1076:BASFジャパン(株)製のオクタデシル−3−(3,5−ジ−t−ブチル−4−ヒドロキシフェニル)プロピオネート)0.3重量部の比率で仕込み、100℃で熱溶解させて微淡黄色透明のワニスを調製した。
(1)で調製したワニス100重量部に対して、ゲル化剤(ALCH:川研ファインケミカル社製のアルミニウム−ジ−iso−プロポキシド−エチルアセトアセテート(アルミニウム錯体化合物))0.6重量部(実施例1)、ゲル化剤(オルガチックス ZC−150:松本ファインケミカル社製のジルコニウムテトラアセチルアセトネート(有機ジルコニウム))1.0重量部(実施例2)、を添加し、110℃で1時間撹拌して透明のゲルワニスを調製した。
光硬化性インキの調製方法
上記(2)で調製したゲルワニス62.6重量部、ジトリメチロールプロパンテトラアクリレート(DTMPTA)10.4重量部、ポリエチレンワックス2重量部、光重合開始剤(Irgacure907:BASFジャパン(株)製、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−オン)5重量部、顔料(フタロシアニンブルー)20重量部を3本ロールで練肉してインキを調製した。
ゲルワニス(上記(2)で調製したゲルワニス)の代わりに、(1)で調製したワニスを用いた点以外は、実施例1、2と同様の方法により、インキを調製した。
調製した実施例1、2及び比較例1のインキを用い、動的粘弾性測定を行い、貯蔵弾性率を測定した。なお、水が混入した場合を想定した「乳化後の」試験については、インキ100重量部に対して水を100重量部添加した後、ディスパーにて3分間撹拌混合し、乳化後のインキを調製し、乳化後のインキを用いて粘弾性試験を行った。
(動的粘弾性測定の条件)
HAAKE MARS III粘弾性測定装置(Thermo Scientific社製)にて、直径35mm、コーン角度2度のコーンプレートを使用して、25℃で周波数掃引測定を行った。
測定した貯蔵弾性率は、比較例1の結果を100として指数表示し、評価結果を表1に示した。指数が大きいほど、貯蔵弾性率が大きいことを示す。
調製したゲルワニス、ワニスにつき、BROOKFIELD VISCOMETER DV−II+Proを用いて25℃での粘度(Pa・s)を測定した。評価結果を表1に示した。
Claims (7)
- 更に、エチレン性不飽和化合物(C)を含有する請求項1又は2に記載の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1〜3のいずれかに記載の光硬化性樹脂組成物。
- 請求項1〜4のいずれかに記載の光硬化性樹脂組成物を含むことを特徴とするインキ。
- 請求項1〜4のいずれかに記載の光硬化性樹脂組成物を含むことを特徴とする塗料。
- オーバープリントワニスである請求項6に記載の塗料。
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