TWI703184B - 光硬化性樹脂組成物、油墨及塗料 - Google Patents
光硬化性樹脂組成物、油墨及塗料 Download PDFInfo
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- TWI703184B TWI703184B TW105102789A TW105102789A TWI703184B TW I703184 B TWI703184 B TW I703184B TW 105102789 A TW105102789 A TW 105102789A TW 105102789 A TW105102789 A TW 105102789A TW I703184 B TWI703184 B TW I703184B
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- Prior art keywords
- resin composition
- allyl
- photocurable resin
- polymer
- weight
- Prior art date
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- 239000000976 ink Substances 0.000 title description 22
- 239000003973 paint Substances 0.000 title description 8
- 229920000642 polymer Polymers 0.000 claims abstract description 53
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims abstract description 41
- 125000006841 cyclic skeleton Chemical group 0.000 claims abstract description 13
- 230000000379 polymerizing effect Effects 0.000 claims abstract description 10
- 125000001424 substituent group Chemical group 0.000 claims abstract description 5
- 229920006395 saturated elastomer Polymers 0.000 claims abstract description 4
- 150000001875 compounds Chemical class 0.000 claims description 28
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- 239000011248 coating agent Substances 0.000 claims description 6
- 125000004185 ester group Chemical group 0.000 claims description 5
- -1 allyl compound Chemical class 0.000 abstract description 44
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- 239000004641 Diallyl-phthalate Substances 0.000 description 12
- 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 12
- 239000000203 mixture Substances 0.000 description 11
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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 6
- 230000000052 comparative effect Effects 0.000 description 6
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- 230000001070 adhesive effect Effects 0.000 description 5
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- 239000004386 Erythritol Substances 0.000 description 4
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- 238000003786 synthesis reaction Methods 0.000 description 4
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- 238000006243 chemical reaction Methods 0.000 description 3
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- YYVYAPXYZVYDHN-UHFFFAOYSA-N 9,10-phenanthroquinone Chemical compound C1=CC=C2C(=O)C(=O)C3=CC=CC=C3C2=C1 YYVYAPXYZVYDHN-UHFFFAOYSA-N 0.000 description 2
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- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
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- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 2
- ORILYTVJVMAKLC-UHFFFAOYSA-N adamantane Chemical compound C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 description 2
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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 2
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- 150000008366 benzophenones Chemical class 0.000 description 2
- JJSLFARHVQTZQN-UHFFFAOYSA-N bis(prop-2-enyl) cyclohex-4-ene-1,2-dicarboxylate Chemical compound C=CCOC(=O)C1CC=CCC1C(=O)OCC=C JJSLFARHVQTZQN-UHFFFAOYSA-N 0.000 description 2
- 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 2
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- 229910001507 metal halide Inorganic materials 0.000 description 2
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- 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 1
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- 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
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- 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 1
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Abstract
Description
本發明係關於一種含有烯丙基系聚合物(A)之光硬化性樹脂組成物、以及含有該樹脂組成物而成之油墨、塗料。更詳細而言,本發明係關於一種與塑膠基材之密接性優異之光硬化性樹脂組成物。
以往,藉由光(例如紫外線)而硬化之各種樹脂組成物被用於油墨、塗料、接著劑、光阻劑等。例如,紫外線硬化型印刷油墨於以下等方面獲得高評價,而得以擴大實用化:硬化速度快而可於短時間硬化,由於不使用溶劑故而適合環境,以及節省資源、節省能源。
於此種樹脂組成物中,含有自酞酸二烯丙酯(鄰酞酸二烯丙酯、異酞酸二烯丙酯、對酞酸二烯丙酯)衍生之酞酸二烯丙酯樹脂之樹脂組成物被用作紙用UV平版油墨(offset ink)。
然而,已知若於用作平版油墨時摻合酞酸二烯丙酯樹脂,則與塑膠基材之密接性不充分(例如專利文獻1)。又,於專利文獻2中,雖然記載有含有「於苯環具有烷基之氫化酞酸二烯丙酯預聚物」及「(甲基)丙烯酸甲酯等」之活性能量線硬化性樹脂組成物,但關於對塑膠基材之密接性未作任何提及。
近年來,市售有聚對酞酸乙二酯(PET)、聚丙烯(PP)等各種塑膠製品,謀求酞酸二烯丙酯樹脂之缺點即與塑膠基材之密接性之提昇。
[專利文獻1]日本特開昭52-4310號公報
[專利文獻2]日本特開平02-77414號公報
本發明之目的在於提供一種與塑膠基材之密接性優異之含有烯丙基系聚合物(A)之光硬化性樹脂組成物。
本發明人進行努力研究,結果發現含有使具有特定結構之烯丙基系化合物進行聚合而獲得之烯丙基系聚合物(A)的光硬化性樹脂組成物與塑膠基材之密接性優異,從而想到本發明。
即,本發明之光硬化性樹脂組成物之特徵在於:含有使下述通式(I)所表示之烯丙基系化合物進行聚合而獲得之烯丙基系聚合物(A)。
[R1及R2分別表示H或CH3,X表示a價基,其為不具有取代基之飽和或部分不飽和之4~8員環的
環狀骨架,a表示2或3]
若含有使上述通式(I)所表示之烯丙基系化合物進行聚合而獲得之烯丙基系聚合物(A),則成為對塑膠基材之密接性優異,乾燥性亦優異之光硬化性樹脂組成物。
又,該光硬化性樹脂組成物尤其對PP(聚丙烯)樹脂之密接性優異,故而適合作為「若採用使用了習知之酞酸二烯丙酯樹脂之組成物則難以提高密接性」之PP樹脂用油墨、塗料的成分。
於本發明之光硬化性樹脂組成物中,較佳上述通式(I)中之X具有下述任一環狀骨架。
本發明之光硬化性樹脂組成物較佳進一步含有乙烯性不飽和化合物(B)。
藉由使用乙烯性不飽和化合物,可提昇光硬化性樹脂組成物之乾燥性,調整為適合用於印刷之黏度,成為塗布作業性優異之組成物。
本發明之光硬化性樹脂組成物較佳進一步含有光聚合起始劑。
藉由含有光聚合起始劑,可順利進行藉由光照射之聚合,故而可於短時間獲得更高分子量之聚合物。
本發明之油墨之特徵在於含有本發明之光硬化性樹脂組成物。
該油墨適合作為用以印刷於塑膠基材之油墨,尤其適合作為用以印刷於PP樹脂製之片、膜等基材之油墨。
本發明之塗料之特徵在於含有本發明之光硬化性樹脂組成物。
該塗料適合作為用以描繪於塑膠基材之塗料,尤其適合作為用以描繪於PP樹脂製之片、膜等基材之塗料。
又,本發明之塗料較佳為套印清漆(overprint varnish)。
根據本發明,於用作油墨、塗料、接著劑及光阻劑之成分之情形時,可獲得對合成高分子之基材、尤其是塑膠基材之密接性優異之光硬化性樹脂組成物。
以下,詳細地說明本發明。
烯丙基系聚合物(A)
本發明之光硬化性樹脂組成物之特徵在於含有使下述通式(I)所表示之烯丙基系化合物進行聚合而獲得之烯丙基系聚合物(A)。
[R1及R2分別表示H或CH3,
X表示a價基,其為不具有取代基之飽和或部分不飽和之4~8員環的環狀骨架,a表示2或3]
作為上述通式(I)中之X之較佳之例,可例示以下之環狀骨架。
作為上述通式(I)中之X之更佳之例,可例示以下之環狀骨架。
作為上述通式(I)中之X之進一步較佳之例,可例示以下之環狀骨架。
X可為各種環狀骨架,亦可為上述以外之環狀骨架。於環狀骨架為部分不飽和之情形時,環狀骨架所具有之雙鍵之數量並不限定於1,亦可為2以上。其中,X並非芳香族之6員環骨架。
X亦可於分子內進行交聯,作為於分子內進行交聯之X之例,可列舉:金剛烷、降莰烯、降莰烷等。
X為a價基,a為2或3,故而X為二價或三價基。於X之環狀骨架鍵結有a個(2個或3個)通式(I)中所示之烯丙基酯基[-CO-O-CH2-CR2=CHR1]。
X之環上之烯丙基酯基[-CO-O-CH2-CR2=CHR1]之取代位置可為任一組合,烯丙基系化合物可為具有不同之取代位置之組合之物質的混合物。尤其於2個烯丙基酯基鍵結於6員環之X時,2個烯丙基酯基可為鄰位配向、間位配向或對位配向中之任一者,較佳為鄰位配向或對位配向。
作為上述通式(I)所表示之烯丙基系化合物之具體例,可例示:1,2-環己烷二羧酸二烯丙酯、1,3-環己烷二羧酸二烯丙酯、1,4-環己烷二羧酸二烯丙酯、4-環己烯-1,2-二羧酸二烯丙酯、2-環己烯-1,2-二羧酸二烯丙酯等。其中,較佳為1,2-環己烷二羧酸二烯丙酯、4-環己烯-1,2-二羧酸二烯丙酯、1,4-環己烷二羧酸二烯丙酯,更佳為1,2-環己烷二羧酸二烯丙酯。
可將「藉由使選自由上述烯丙基系化合物所組成之群中之至少1種以上進行聚合而獲得之烯丙基系聚合物(A)」用於光硬化性樹脂組成物。進一步,亦可將「使上述通式(I)所表示之烯丙基系化合物與其他
可聚合之化合物進行共聚合而成者」用於光硬化性樹脂組成物。
作為獲得作為上述通式(I)所表示之烯丙基系化合物之具體例所列舉之化合物之方法的例子,可列舉:使環己烷二羧酸或環己烷二羧酸酐與烯丙醇或氯化烯丙基進行酯化反應之方法;及使環己烯二羧酸或環己烯二羧酸酐與烯丙醇或氯化烯丙基進行酯化反應之方法。
又,亦可使用作為上述通式(I)所表示之烯丙基系化合物之具體例所列舉之化合物的市售品。
上述通式(I)所表示之烯丙基系化合物之聚合方法並無特別限定,可使用通常之聚合反應。於上述聚合反應中,視需要亦可適當添加聚合起始劑。藉由使用聚合起始劑,可於短時間獲得更高分子量之聚合物。
作為用於烯丙基系化合物之聚合反應之聚合起始劑,可列舉:偶氮雙異丁腈、2,2'-偶氮雙異丁酸二甲酯等偶氮起始劑;過氧化酮、過氧化縮酮、過氧化氫、過氧化二烷基、過氧化二醯基、過氧化二碳酸酯、過氧化酯、過氧化苯甲醯等過氧化物起始劑;2-甲基-1-[4-(甲硫基)苯基]-2-N-啉基丙烷-1-酮、1-羥基環己基苯基酮等苯乙酮系;安息香、安息香乙醚等安息香系;二苯甲酮等二苯甲酮系;醯基膦氧化物等磷系;9-氧硫等硫系;二苯基乙二酮、9,10-菲醌等二苯基乙二酮系光聚合起始劑。
聚合起始劑之量相對於通式(I)所表示之烯丙基系化合物之單體100重量份,較佳為5.0重量份以下,更佳為3.0重量份以下。又,尤佳為0.001~3.0重量份。
聚合時之反應溫度較佳為60~240℃、例如80~220℃。反應時間較佳為0.1~100小時、例如1~30小時。
藉由利用上述方法等使上述通式(I)所表示之烯丙基系化合物進行聚合,可製備具有基於上述通式(I)所表示之烯丙基系化合物之單體單元之烯丙基系聚合物(A)。
基於上述通式(I)所表示之烯丙基系化合物之單體單元之含量於烯丙基系聚合物(A)100重量%中,較佳為20重量%以上,更佳為50重量%以上,進一步較佳為80重量%以上,尤佳為98重量%以上,亦可為100重量%。
烯丙基系聚合物(A)之重量平均分子量較佳為300,000以下,更佳為200,000以下。又,進一步較佳為2,000~150,000,尤佳為5,000~140,000。
本發明之光硬化性樹脂組成物中之烯丙基系聚合物(A)之含量相對於光硬化性樹脂組成物總量,較佳為1~60重量%,更佳為1~55重量%,進一步較佳為1~50重量%。下限尤佳為20重量%。若烯丙基系聚合物(A)之含量超過60重量%,則有對乙烯性不飽和化合物(B)之溶解性變差,黏度亦變高,操作性變差之情況。若烯丙基系聚合物(A)之含量未達1重量%,則有所獲得之光硬化性樹脂組成物無法獲得充分之乾燥性之情況。
乙烯性不飽和化合物(B)
本發明之光硬化性樹脂組成物較佳含有可藉由光照射硬化之乙烯性不飽和化合物(B)。乙烯性不飽和化合物(B)較佳具有1~20個碳-碳雙鍵,
更佳具有1~10個,進一步較佳具有2~6個。作為乙烯性不飽和化合物(B),可列舉:(甲基)丙烯酸酯化合物、(甲基)烯丙基化合物及乙烯基化合物等。又,乙烯性不飽和化合物亦可使用2種以上之化合物之混合物。
作為(甲基)丙烯酸酯化合物,可例示:新戊四醇、二新戊四醇、三羥甲基丙烷、二-三羥甲基丙烷、新戊二醇、1,6-己二醇、甘油、聚乙二醇、聚丙二醇等醇類之(甲基)丙烯酸酯化合物、及對該等加成環氧乙烷、環氧丙烷等環氧烷(alkylene oxide)而成之(甲基)丙烯酸酯化合物;對雙酚A、雙酚F等雙酚類加成環氧乙烷、環氧丙烷等環氧烷而成者之(甲基)丙烯酸酯化合物;環氧(甲基)丙烯酸酯、(甲基)丙烯酸胺酯(urethane(meth)acrylate)、醇酸(甲基)丙烯酸酯等(甲基)丙烯酸酯化合物;環氧化大豆油丙烯酸酯等(甲基)丙烯酸酯化合物;較佳為新戊四醇、二新戊四醇、三羥甲基丙烷、二-三羥甲基丙烷、新戊二醇、1,6-己二醇、甘油、聚乙二醇、聚丙二醇等醇類之(甲基)丙烯酸酯化合物、及對該等加成環氧乙烷、環氧丙烷等環氧烷而成之(甲基)丙烯酸酯化合物,更佳為新戊四醇、二新戊四醇、三羥甲基丙烷、二-三羥甲基丙烷等醇類之(甲基)丙烯酸酯化合物、及對該等加成環氧乙烷、環氧丙烷等環氧烷而成之(甲基)丙烯酸酯化合物。
作為(甲基)烯丙基化合物,可例示:酞酸二(甲基)烯丙酯、三聚異氰酸三(甲基)烯丙酯等。
作為乙烯基化合物,可例示:苯乙烯、二乙烯苯、N-乙烯基吡咯啶酮、乙酸乙烯酯等。
其中,就與烯丙基系聚合物(A)之相溶性、光硬化時之硬
化性之方面而言,較佳為二-三羥甲基丙烷四丙烯酸酯、三羥甲基丙烷三丙烯酸酯,更佳為二-三羥甲基丙烷四丙烯酸酯。
本發明之光硬化性樹脂組成物中所含有之乙烯性不飽和化合物(B)之含量相對於光硬化性樹脂組成物中之烯丙基系聚合物(A)100重量份,較佳為50~400重量份,更佳為50~300重量份,進一步較佳為50~250重量份。
又,本發明之光硬化性樹脂組成物中之烯丙基系聚合物(A)與乙烯性不飽和化合物(B)之比率(烯丙基系聚合物:乙烯性不飽和化合物)以重量比計為10:90~90:10之範圍即可,較佳為20:80~80:20之範圍,更佳為30:70~50:50之範圍。若為上述範圍內,則容易獲得對塑膠基材之充分之密接性。
其他添加物
本發明之光硬化性樹脂組成物亦可含有聚合起始劑,尤佳含有光聚合起始劑。作為光硬化性樹脂組成物中所含有之光聚合起始劑,可列舉:2-甲基-1-[4-(甲硫基)苯基]-2-N-啉基丙烷-1-酮、1-羥基環己基苯基酮等苯乙酮系;安息香、安息香乙醚等安息香系;二苯甲酮等二苯甲酮系;醯基膦氧化物等磷系;9-氧硫等硫系;二苯基乙二酮、9,10-菲醌等二苯基乙二酮系。
光硬化性樹脂組成物中所含有之光聚合起始劑之量相對於光硬化性樹脂組成物整體,較佳為0.1~15重量%之範圍,更佳為0.5~12重量%之範圍,進一步較佳為1~10重量%之範圍。
於光硬化性樹脂組成物中亦可併用光起始助劑(例如三乙醇
胺等胺系光起始助劑)。
光起始助劑之量相對於光硬化性樹脂組成物整體,較佳為0.1~5重量%之範圍,更佳為0.5~3重量%之範圍。
本發明之光硬化性樹脂組成物亦可含有密接賦予樹脂。作為光硬化性樹脂組成物中所含有之密接賦予樹脂,例如可例示:不飽和聚酯樹脂、聚醯胺樹脂、環氧樹脂、酚樹脂、氯乙烯樹脂、乙酸乙烯酯樹脂、胺酯(urethane)樹脂、ABS樹脂、AS樹脂、AAS樹脂、乙烯-氯乙烯共聚物樹脂、丁醛樹脂、乙烯-乙酸乙烯酯共聚物樹脂、聚醯亞胺樹脂、聚縮醛樹脂、聚乙烯樹脂、聚碳酸酯樹脂、苯乙烯樹脂、苯乙烯-順丁烯二酸樹脂、聚碸樹脂、三聚氰胺樹脂、脲樹脂、二甲苯樹脂、薰草哢樹脂、酮樹脂、順丁烯二酸樹脂、聚乙烯醇、聚乙烯醚、聚萜烯樹脂、萜酚樹脂及丙烯酸樹脂等。
於該等中,就提高對聚丙烯等烯烴系樹脂膜之密接性之觀點而言,較佳為極性低之樹脂,更佳為作為表示極性之尺度之SP值為7.0~10.0之樹脂,進一步較佳為SP值為8.0~10.0之樹脂,尤佳為SP值為9.0~10.0之樹脂。
作為此種樹脂,可列舉:聚乙烯樹脂(SP值8.1)、苯乙烯樹脂(SP值9.1)、乙酸乙烯酯樹脂(SP值9.4)、氯乙烯樹脂(SP值9.6)、聚碳酸酯樹脂(SP值9.8)、苯乙烯-順丁烯二酸樹脂(SP值9.85)等。
SP值可藉由Fedors之方法(記載於Polymer Engineering and Science,14,(2),147(1974))而算出。
又,就提高對聚丙烯等烯烴系樹脂膜之密接性之觀點、及添
加於光硬化性樹脂組成物中時之與烯丙基系聚合物(A)及乙烯性不飽和化合物(B)之相溶性之方面而言,較佳為含有苯環之樹脂,更佳為具有基於苯乙烯之單體單元之苯乙烯系樹脂。作為苯乙烯系樹脂,可列舉:AS樹脂、ABS樹脂、苯乙烯樹脂、苯乙烯-順丁烯二酸樹脂等,尤佳為苯乙烯樹脂及苯乙烯-順丁烯二酸樹脂。
光硬化性樹脂組成物中所含有之密接賦予樹脂之含量相對於光硬化性樹脂組成物之烯丙基系聚合物(A)100重量份,較佳為50~1000重量份,更佳為100~900重量份,尤佳為200~800重量份。若為上述範圍內,則可獲得與塑膠基材之充分之密接性,且保持烯丙基系聚合物(A)與密接賦予樹脂充分地溶解之狀態,成為相溶性優異之組成物。進一步,即便添加乙烯性不飽和化合物(B),亦可保持充分地溶解之狀態。
本發明之光硬化性樹脂組成物可根據目的含有各種添加劑,若進行例示,則有穩定劑(例如對苯二酚、對甲氧基苯酚等聚合抑制劑)、顏料(例如青藍、雙偶氮黃(disazo yellow)、胭脂紅6b、色澱紅C、碳黑、鈦白)等著色劑、填充劑、黏度調整劑等。光硬化性樹脂組成物中所含有之穩定劑之量相對於光硬化性樹脂組成物整體,較佳為0.01~2重量%之範圍,更佳為0.1~1重量%之範圍。
著色劑之量相對於光硬化性樹脂組成物整體,較佳為1~50重量%之範圍,更佳為1~45重量%之範圍。
本發明之光硬化性樹脂組成物可藉由「於烯丙基系聚合物(A)中視需要混合乙烯性不飽和化合物(B),進一步混合光聚合起始劑、光起始助劑、密接賦予樹脂、添加劑(例如穩定劑、顏料)」而製造。本發
明之光硬化性樹脂組成物係藉由照射光而硬化。用於硬化之光一般為紫外線。
用於光硬化性樹脂組成物之硬化反應之硬化裝置及硬化條件並無特別限定,只要為用於通常之光硬化反應之方法即可。
本發明之光硬化性樹脂組成物之用途並無特別限定。可用於油墨(例如光硬化性平版用印刷油墨、絲網印刷油墨、凹版油墨等印刷油墨)、塗料(例如紙用、塑膠用、金屬用、木工用等之塗料,若進行例示,則有套印清漆)、接著劑、光阻劑等技術領域。
含有本發明之光硬化性樹脂組成物之油墨為本發明之油墨,含有本發明之光硬化性樹脂組成物之塗料為本發明之塗料。又,本發明之塗料較佳為套印清漆。
例如,油墨之一般製作方法如下所述。於60℃~100℃之溫度一面攪拌一面使烯丙基系聚合物(A)及穩定劑等溶解於乙烯性不飽和化合物(B),而製作清漆。於該清漆中,藉由蝶形混合機攪拌混合顏料、光聚合起始劑、其他添加劑後,藉由三輥研磨機等進行研磨,藉此獲得油墨。
又,套印清漆之製作不使用顏料,除此以外,可藉由與油墨相同之順序進行。
(實施例)
以下,列舉實施例,更具體地說明本發明,但本發明並不限定於該等實施例。
烯丙基系聚合物之重量平均分子量(Mw)、分子量分布(Mw/Mn)之測定
重量平均分子量(Mw)、分子量分布(Mw/Mn)係使用GPC進行測定。Mw、Mn為標準聚苯乙烯換算之重量平均分子量、數量平均分子量之值。
管柱:將Shodex KF-806L、KF-804、KF-803、KF-802、KF-801串聯連接
流速:1.0mL/min
溫度:40℃
檢測:RID-6A
試樣:使試樣20mg溶解於四氫呋喃10mL,作為測定用樣品。
製造例1 1,2-環己烷二羧酸二烯丙酯聚合物之合成
1,2-環己烷二羧酸二烯丙酯係藉由使環己烷二羧酸酐與烯丙醇進行酯化反應而製造。
於3L之可分離式燒瓶中加入1,2-環己烷二羧酸二烯丙酯2400g,並加入60g之過氧化苯甲醯,於80℃進行加熱攪拌。使之反應2.5小時後,冷卻至30℃。冷卻後,於燒瓶中加入甲醇,使聚合物沈澱。將所獲得之聚合物於40℃減壓乾燥16小時(產量:408g,產率:17%,Mw=32,000,Mw/Mn=2.8)。將所獲得之聚合物作為聚合物1,用於實施例1。
製造例2~4 1,2-環己烷二羧酸二烯丙酯聚合物之合成
藉由與製造例1相同之聚合條件,改變聚合時間,藉此進行1,2-環己烷二羧酸二烯丙酯聚合物之合成。再者,將製造例2中所獲得之聚合物(產量:612g,產率:25.5%,Mw=63,000,Mw/Mn=4.7)作為聚合物2,用於實施例2及5。將製造例3中所獲得之聚合物(產量:672g,產率:28%,
Mw=89,000,Mw/Mn=6.9)作為聚合物3,用於實施例3。將製造例4中所獲得之聚合物(產量:720g,產率:30%,Mw=140,000,Mw/Mn=5.4)作為聚合物4,用於實施例4。
製造例5 3或4-甲基-六氫酞酸1,2-順式-二烯丙酯聚合物之合成
基於日本特開2012-116868號公報中記載之合成方法,合成3或4-甲基-六氫酞酸1,2-順式-二烯丙酯聚合物(產量:624g,產率:26%,Mw=50,000,Mw/Mn=3.8)。將所獲得之聚合物作為聚合物5,用於比較例2及3。
實施例1~5、比較例1~3
製備下述表1中記載之各組成之光硬化性樹脂組成物,評價光硬化性樹脂組成物之特性。
1)光硬化性樹脂組成物之溶解性之評價
以下述表1中記載之各組成量添加製造例1~5中所獲得之聚合物1~5或DAP樹脂、乙烯性化合物及聚合起始劑,加熱至100℃並進行混合而製備光硬化性樹脂組成物。根據冷卻至室溫後經過一晚後者之外觀是否為透明而確認溶解性。將冷卻後外觀亦為透明者設為○,將白濁者設為×。將結果示於表2。
表1所示之聚合物1~5以外之成分如下所述。
又,表1所示之組成量係以重量份計之記載。
DAP樹脂:大阪曹達股份有限公司製造之酞酸二烯丙酯樹脂
DTMPA:沙多瑪股份有限公司製造之SR355二-三羥甲基丙烷四丙烯酸酯
DPHA:東亞合成股份有限公司製造之Aronix M-404二新戊四醇六丙烯酸酯
3EO-TMPTA:新中村化學工業股份有限公司製造之NK ester A-TMPT-3EO環氧乙烷改質三羥甲基丙烷三丙烯酸酯
Irganox 1076:BASF Japan股份有限公司製造之3-(3,5-二-三級丁基-4-羥基苯基)丙酸十八酯
2)黏度
針對所製備之光硬化性樹脂組成物,使用BROOKFIELD VISCOMETER
DV-II+Pro,測定30℃之黏度。將評價結果示於表2。
3)乾燥性
針對所製備之光硬化性樹脂組成物,藉由不黏著輸送帶速度(tack free conveyor speed)(m/min)評價乾燥性。將評價結果示於表2。
該值越大則乾燥性越優異。
4)密接性試驗
使用No.2棒式塗布機將所製備之各光硬化性樹脂組成物分別塗敷於2種塑膠基材(聚丙烯基材:龍田化學股份有限公司製造之非延伸高透明PP片商品名:High P Crystal ST-500厚度0.3mm;及聚丙烯基材:出光統一科技股份有限公司製造之非延伸高透明PP片商品名:Superpurelay SG-140TC厚度0.3mm),使用輸出60W/cm之金屬鹵化物燈(照射距離10cm),以塗膜變得不黏著之輸送帶速度使之硬化。再者,UV硬化裝置使用愛古拉飛克斯股份有限公司製造之輸送帶型紫外線硬化裝置。將米其邦製造之寬度18mm之Sellotape(註冊商標)(編號:LP-18,黏著力:4.01N/10mm)貼附於所獲得之塗膜,以拇指強烈摩擦30秒以上後,將Sellotape(註冊商標)慢慢撕離,自中途急遽撕離而評價塗膜之剝離之程度。評價基準如下所述。將評價結果示於表2。
5:即便急遽撕離亦未剝離者
4:即便慢慢撕離亦未完全剝離,但若急遽撕離則稍微剝離者
3:若急遽撕離則發生剝離,但慢慢撕離亦未完全剝離者
2:即便慢慢撕離亦剝離50%左右者
1:即便慢慢撕離亦剝離者
5)硬化性試驗
將所製備之各光硬化性樹脂組成物塗敷於載玻片(松浪硝子工業股份有限公司製造之S9213標準大型水研磨t1.3),使用輸出60W/cm之金屬鹵化物燈(照射距離10cm)進行硬化,藉由安田精機製作所股份有限公司之手推鉛筆刮痕硬度試驗機,利用依據JIS K5600之方法測定鉛筆硬度。將評價結果示於表2。
如實施例1~5所示,使用聚合物1~4(為使通式(I)所表示之烯丙基系化合物進行聚合而獲得之烯丙基系聚合物(A))所製備之光硬化性樹脂組成物具有與「如比較例1所示之使用酞酸二烯丙酯樹脂所製備之光硬化性樹脂組成物」同等的乾燥性。而且,對「若採用使用酞酸二烯丙酯樹脂所製備之比較例1之光硬化性樹脂組成物則難以密接」之聚丙烯片之密接性亦優異。
又,關於使用使「相當於通式(I)中X具有取代基(甲基)之化合物之烯丙基系化合物」進行聚合而獲得之聚合物5所製備的比較例3之光硬化性樹脂組成物,乾燥性差,對聚丙烯片(膜)之密接性亦不充分。
又,併用酞酸二烯丙酯樹脂及聚合物5所製備之比較例2之光硬化性樹脂組成物無法塗布於聚丙烯片。
本發明之光硬化性樹脂組成物可用於塑膠基材用油墨(例如平版油墨)、塗料、接著劑、光阻劑等。
Claims (6)
- 如申請專利範圍第1項之光硬化性樹脂組成物,其進一步含有乙烯性不飽和化合物(B)。
- 如申請專利範圍第1或2項之光硬化性樹脂組成物,其進一步含有光聚合起始劑。
- 一種油墨,含有申請專利範圍第1至3項中任一項之光硬化性樹脂組成物。
- 一種塗料,含有申請專利範圍第1至3項中任一項之光硬化性樹脂組成物。
- 如申請專利範圍第5項之塗料,其為套印清漆(overprint varnish)。
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WO2017169661A1 (ja) | 2016-03-31 | 2017-10-05 | 株式会社大阪ソーダ | 光硬化性樹脂組成物、及びその硬化物 |
JP2018154724A (ja) * | 2017-03-17 | 2018-10-04 | 株式会社大阪ソーダ | 白色インキ用組成物 |
JP6597688B2 (ja) * | 2017-03-23 | 2019-10-30 | 東洋インキScホールディングス株式会社 | 活性エネルギー線硬化型樹脂組成物、インキおよび印刷物 |
JP6997942B2 (ja) * | 2017-07-26 | 2022-02-10 | 株式会社大阪ソーダ | 光硬化性樹脂組成物、インキ及び塗料 |
EP3674329A4 (en) * | 2017-08-24 | 2021-05-05 | Osaka Soda Co., Ltd. | LIGHT CURABLE RESIN COMPOSITION, INK AND VARNISH |
JP6725079B2 (ja) * | 2017-08-24 | 2020-07-15 | 株式会社大阪ソーダ | 不飽和ポリエステル樹脂組成物 |
JP2020050735A (ja) * | 2018-09-26 | 2020-04-02 | 岡本化学工業株式会社 | 光学的立体造形用組成物、並びに立体造形物、及びその製造方法 |
WO2021044729A1 (ja) | 2019-09-02 | 2021-03-11 | 株式会社大阪ソーダ | 光硬化性樹脂組成物、インキ及び塗料 |
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JP2023121316A (ja) * | 2022-02-21 | 2023-08-31 | サカタインクス株式会社 | 活性エネルギー線硬化型インキ組成物 |
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US3551311A (en) * | 1967-11-24 | 1970-12-29 | Sun Chemical Corp | Radiation-curable compositions |
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JPS58103519A (ja) * | 1981-12-15 | 1983-06-20 | Teijin Ltd | 硬化性樹脂組成物 |
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JP2007056187A (ja) | 2005-08-26 | 2007-03-08 | Toyo Ink Mfg Co Ltd | 硬化性組成物、それを使用した活性エネルギー線硬化性印刷インキ及びその印刷物 |
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US20120123014A1 (en) * | 2010-11-17 | 2012-05-17 | Xerox Corporation | Overprint varnish formulations |
JP2013124218A (ja) | 2011-12-13 | 2013-06-24 | Daiso Co Ltd | 新規アリルエステル化合物およびその製法 |
CN105121513B (zh) | 2013-06-17 | 2017-05-10 | 昭和电工株式会社 | 烯硫醇系固化性组合物及其固化物 |
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EP3199562B1 (en) | 2024-04-03 |
EP3199562A4 (en) | 2018-04-11 |
EP3199562A1 (en) | 2017-08-02 |
TW201629139A (zh) | 2016-08-16 |
CN106715498B (zh) | 2020-09-11 |
JP6690554B2 (ja) | 2020-04-28 |
US11084891B2 (en) | 2021-08-10 |
US20190135955A1 (en) | 2019-05-09 |
JPWO2016125661A1 (ja) | 2017-11-09 |
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US20170313795A1 (en) | 2017-11-02 |
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