TWI808944B - 光硬化性樹脂組成物、墨水及塗料 - Google Patents
光硬化性樹脂組成物、墨水及塗料 Download PDFInfo
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- TWI808944B TWI808944B TW106127016A TW106127016A TWI808944B TW I808944 B TWI808944 B TW I808944B TW 106127016 A TW106127016 A TW 106127016A TW 106127016 A TW106127016 A TW 106127016A TW I808944 B TWI808944 B TW I808944B
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- 125000000217 alkyl group Chemical group 0.000 claims abstract description 5
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- PYGSKMBEVAICCR-UHFFFAOYSA-N hexa-1,5-diene Chemical group C=CCCC=C PYGSKMBEVAICCR-UHFFFAOYSA-N 0.000 description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
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- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 4
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- JQRRFDWXQOQICD-UHFFFAOYSA-N biphenylen-1-ylboronic acid Chemical compound C12=CC=CC=C2C2=C1C=CC=C2B(O)O JQRRFDWXQOQICD-UHFFFAOYSA-N 0.000 description 1
- INLLPKCGLOXCIV-UHFFFAOYSA-N bromoethene Chemical compound BrC=C INLLPKCGLOXCIV-UHFFFAOYSA-N 0.000 description 1
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- 239000003112 inhibitor Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
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- 150000005309 metal halides 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
- XJRBAMWJDBPFIM-UHFFFAOYSA-N methyl vinyl ether Chemical compound COC=C XJRBAMWJDBPFIM-UHFFFAOYSA-N 0.000 description 1
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- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
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- 239000004408 titanium dioxide Substances 0.000 description 1
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Classifications
-
- 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
- C08F26/00—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 single or double bond to nitrogen or by a heterocyclic ring containing nitrogen
- C08F26/06—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 single or double bond to nitrogen or by a heterocyclic ring containing nitrogen by a heterocyclic ring containing nitrogen
-
- 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
- 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
-
- 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
- C08F271/00—Macromolecular compounds obtained by polymerising monomers on to polymers of nitrogen-containing monomers as defined in group C08F26/00
- C08F271/02—Macromolecular compounds obtained by polymerising monomers on to polymers of nitrogen-containing monomers as defined in group C08F26/00 on to polymers of monomers containing heterocyclic nitrogen
-
- 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
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Abstract
本發明提供一種與塑膠基材之密合性優異之含有聚合物(A)之光硬化性樹脂組成物。
本發明係關於一種光硬化性樹脂組成物,其特徵在於含有使通式[I]所表示之化合物聚合而獲得之聚合物(A)(式中,R1表示[-CH2-CR3=CHR2]基、縮水甘油基、碳數1~5之烷基或氫原子,各個R1可不同,亦可相同,其中之至少1個為[-CH2-CR3=CHR2]基,[-CH2-CR3=CHR2]基中之R2及R3分別表示H或CH3)。
Description
本發明係關於一種含有使通式[I]所表示之化合物聚合而獲得之聚合物(A)之光硬化性樹脂組成物、以及含有該樹脂組成物而成之墨水、塗料。更詳細而言,本發明係關於一種與塑膠基材之密合性優異之光硬化性樹脂組成物。
習知,藉由光(例如紫外線)而硬化之各種樹脂組成物被用於墨水、塗料、接著劑、光阻劑等。例如,紫外線硬化型之印刷墨水其硬化速度快而可於短時間內硬化;由於未使用溶劑而適合環境;及節省資源、節能等方面上評價較高而被廣泛實用化。
此種樹脂組成物之中,含有自苯二甲酸二烯丙酯(鄰苯二甲酸二烯丙酯、間苯二甲酸二烯丙酯、對苯二甲酸二烯丙酯)衍生之苯二甲酸二烯丙酯樹脂之樹脂組成物被採用作紙用之UV膠版墨水。
然而,已知於用作膠版墨水時若摻合苯二甲酸二烯丙酯樹脂,則與塑膠基材之密合性不足(例如,專利文獻1)。又,記載有含有顏料、紫外線硬化性樹脂、及光聚合起始劑之非吸收材料用紫外線硬化型噴墨墨水組成物,且紫外線硬化性樹脂中為具有三環之3官能以上之烯丙
基、丙烯酸聚酯及(甲基)丙烯酸酯者(專利文獻2)。然而,上述非吸收材料用紫外線硬化型噴墨墨水組成物係噴墨用之組成物,於對塑膠基材之密合性或乾燥性之方面上並不充分。
近年來,市售有聚對苯二甲酸乙二酯(PET)、聚丙烯(PP)等各種各樣之塑膠製品,而要求提高苯二甲酸二烯丙酯樹脂之作為缺點之與塑膠基材之密合性。
專利文獻1:日本特開昭52-4310號公報
專利文獻2:日本特開2005-68255號公報
本發明之目的在於提供一種與塑膠基材之密合性優異之含有聚合物(A)之光硬化性樹脂組成物。
本發明者進行了努力研究,結果發現,含有使具有特定結構之化合物聚合而獲得之聚合物(A)之光硬化性樹脂組成物與塑膠基材之密合性優異,從而思及本發明。
即,本發明之光硬化性樹脂組成物其特徵在於:
含有使下述通式[I]所表示之化合物聚合而獲得之聚合物(A)。
(式中,R1表示[-CH2-CR3=CHR2]基、縮水甘油基、碳數1~5之烷基或氫原子,各個R1可不同,亦可相同,其中之至少1個為[-CH2-CR3=CHR2]基,[-CH2-CR3=CHR2]基中之R2及R3分別表示H或CH3)。
若含有使上述通式[I]所表示之化合物聚合而獲得之聚合物(A),則成為對塑膠基材之密合性優異且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對PP(聚丙烯)樹脂之密合性尤其優異,故而作為習知之使用苯二甲酸二烯丙酯樹脂之組成物難以提高密合性之PP樹脂用之墨水、塗料之成分適合。
本發明之光硬化性樹脂組成物較佳為進而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,光硬化性樹脂組成物之乾燥性提高,而可調整為適合用於印刷之黏度,而成為塗佈作業性優異之組成物。
本發明之光硬化性樹脂組成物較佳為進而含有光聚合起始劑。藉由含有光聚合起始劑,藉由光照射而進行之聚合順利地進行,故而可於短時間內獲得硬化物。
本發明之墨水其特徵在於含有本發明之光硬化性樹脂組成物。
該墨水適合作為用以印刷於塑膠基材之墨水,尤其是適合作為用以印刷於PP樹脂製之片材、膜等基材之墨水。
本發明之塗料其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繪製於塑膠基材之塗料,尤其是適合作為用以繪製於PP樹脂製之片材、膜等基材之塗料。
又,本發明之塗料較佳為套印(overprinting)清漆。
根據本發明,於用作墨水、塗料、接著劑及光阻劑之成分之情形時,獲得對合成高分子之基材、尤其是塑膠基材之密合性優異之光硬化性樹脂組成物。
以下,對本發明詳細地進行說明。
聚合物(A)
本發明之光硬化性樹脂組成物其特徵在於含有使下述通式[I]所表示之化合物聚合而獲得之聚合物(A)。
於本發明中,關於藉由含有聚合物(A)而對合成高分子之基材、尤其是塑膠基材之密合性優異之原因,雖未確定,但推測如下。
推測原因在於:於使下述通式[I]所表示之化合物聚合而獲得之聚合物
(A)中,基於異氰尿酸酯環之結構(下述通式[I]中之環結構(異氰酸酯之三聚物))連續地存在,藉由連續存在之基於異氰尿酸酯環之結構而對合成高分子之基材、尤其是塑膠基材之密合性優異。
(式中,R1表示[-CH2-CR3=CHR2]基、縮水甘油基、碳數1~5(較佳為碳數1~3)之烷基或氫原子,各個R1可不同,亦可相同,其中之至少1個(尤佳為2個,更佳為3個)為[-CH2-CR3=CHR2]基,[-CH2-CR3=CHR2]基中之R2及R3分別表示H或CH3)。
如上所述,R1為至少1個為[-CH2-CR3=CHR2]基,較佳為2個為[-CH2-CR3=CHR2]基,更佳為3個為[-CH2-CR3=CHR2]基。[-CH2-CR3=CHR2]基之數量越多,反應性越是提高,而越容易獲得更高分子量之聚合物。
R2及R3較佳為H(氫原子),更佳為均為H(氫原子)。
通式[I]中,於R1為烷基之情形時,可列舉:甲基、乙基、丙基、異丙基、丁基、異丁基、第二丁基、第三丁基、戊基等,其中,較佳為甲基、乙基、丙基、異丙基,更佳為甲基、乙基。
作為具有通式[I]所表示之結構之化合物之具體例,可列舉:異氰尿酸三烯丙酯、異氰尿酸二烯丙基單縮水甘油酯、異氰尿酸二烯丙基單甲酯、異氰尿酸二烯丙基單乙酯、異氰尿酸二烯丙基單丙酯、異氰尿酸
三甲基烯丙酯、異氰尿酸二烯丙酯、異氰尿酸單烯丙基二甲酯、異氰尿酸單烯丙基二乙酯、異氰尿酸單烯丙基二丙酯、異氰尿酸單烯丙基二縮水甘油酯、異氰尿酸單烯丙基單乙基單甲酯、異氰尿酸單烯丙酯、異氰尿酸單烯丙基二甲基烯丙酯、異氰尿酸單烯丙基單甲基烯丙基單甲酯等。其等之中,較佳為異氰尿酸三烯丙酯、異氰尿酸二烯丙基單縮水甘油酯、異氰尿酸二烯丙基單甲酯、異氰尿酸二烯丙酯,更佳為異氰尿酸三烯丙酯、異氰尿酸二烯丙基單甲酯、異氰尿酸二烯丙酯,尤佳為異氰尿酸三烯丙酯。
可將藉由使上述式[I]所表示之化合物聚合而獲得之聚合物(A)用於光硬化性樹脂組成物。進而,亦可將使上述通式[I]所表示之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。作為可共聚合之化合物,可列舉:丙烯酸甲酯、丙烯酸丁酯等丙烯酸酯類;乙酸乙烯酯、月桂酸乙烯酯、苯甲酸乙烯酯等各種脂肪族及芳香族羧酸乙烯酯類;氯乙烯、溴乙烯等乙烯類;偏二氯乙烯、偏溴二乙烯等二乙烯類;甲基乙烯醚、丁基乙烯醚等乙烯基烷基醚類;三羥甲基丙烷二烯丙醚、新戊四醇三烯丙醚等烯丙醚類;乙酸烯丙酯、苯甲酸烯丙酯等各種脂肪族及芳香族羧酸烯丙酯類;對苯二甲酸二烯丙酯、檸檬酸三烯丙酯等多元酸烯丙酯類等。聚合物(A)中之共聚合成分之摻合比率只要為2~50重量%即可,較佳為2~20重量%。
作為獲得作為上述通式[I]所表示之化合物之具體例所列舉之化合物的方法之例,可藉由通常已知之聚合方法進行合成,亦可使用市售品。
上述通式[I]所表示之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,亦可視需要適當添加聚合起始劑。藉由使用聚合起始劑,而可於短時間內獲得更高分子量之聚合物(A)。
作為用於通式[I]所表示之化合物之聚合反應之聚合起始劑,可列舉:偶氮二異丁腈、2,2'-偶氮二異丁酸二甲酯等偶氮起始劑;過氧化酮、過氧縮酮、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-嗎福林基丙烷-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;醯基氧化膦等磷系;9-氧硫等硫系;及苯偶醯、9,10-菲醌等苯偶醯系之光聚合起始劑。
聚合起始劑之量相對於通式[I]所表示之化合物之單體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。
藉由上述方法等使上述通式[I]所表示之化合物進行聚合,藉此可製備具有基於上述通式[I]所表示之化合物之單體單元之聚合物(A)。
基於上述通式[I]所表示之化合物之單體單元之含量於聚合物(A)100重量%中,較佳為20重量%以上,更佳為50重量%以上,進而較佳為80重量%以上,尤佳為98重量%以上,且亦可為100重量%。
聚合物(A)之重量平均分子量(Mw)較佳為250,000以下,更佳為200,000以下。又,聚合物(A)之重量平均分子量較佳為2,000以上,
更佳為5,000以上。又,聚合物(A)之重量平均分子量進而較佳為10,000~150,000,尤佳為20,000~140,000。
聚合物(A)之分子量分佈(重量平均分子量(Mw)/數量平均分子量(Mn))較佳為1.5~10.0,更佳為3.0~7.5。於本說明書中,聚合物(A)之重量平均分子量(Mw)、數量平均分子量(Mn)係藉由實施例所記載之方法所測得之值。
本發明之光硬化性樹脂組成物中之聚合物(A)之含量相對於光硬化性樹脂組成物總量,較佳為1~50重量%,更佳為1~40重量%,進而較佳為1~30重量%。下限尤佳為1重量%,且亦可為5重量%。若聚合物(A)之含量超過50重量%,則存在對於乙烯性不飽和化合物(B)之溶解性變差,黏度亦變高而處理性變差之情況。若聚合物(A)之含量未達1重量%,則存在所獲得之光硬化性樹脂組成物無法獲得充分之乾燥性或密合性之情況。
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為含有可藉由光照射而進行硬化之乙烯性不飽和化合物(B)。乙烯性不飽和化合物(B)較佳為具有1~20個碳-碳雙鍵,更佳為具有1~10個,進而較佳為具有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系化合物(vinyl compound)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、及對其等加成環氧乙烷、環氧丙烷等環氧烷而成之(甲基)丙烯酸酯化合物;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之(甲基)丙烯酸酯化合物;(甲基)丙烯酸環氧酯、(甲基)丙烯酸胺酯、醇酸(甲基)丙烯酸酯等(甲基)丙烯酸酯化合物;及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其等加成環氧乙烷、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其等加成環氧乙烷、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,可例示苯二甲酸二(甲基)烯丙酯等。
作為乙烯系化合物,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,就與聚合物(A)之相容性、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、及對其等加成環氧乙烷、環氧丙烷等環氧烷而成者。
本發明之光硬化性樹脂組成物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聚合物(A)100重量份,較佳為50~1200重量份,更佳為50~1000重量份,進而較佳為100~900重量份。
又,本發明之光硬化性樹脂組成物中之聚合物(A)與乙烯性不飽和化合物(B)之比率(聚合物:乙烯性不飽和化合物)只要以重量比計為5:95~95:5之範圍即可,較佳為10:90~90:10之範圍,更佳為10:90~70:30之範圍,進而較佳為10:90~50:50之範圍。只要為上述範圍內,則容易獲得對塑膠基材之充分之密合性。
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,尤佳為含有光聚合起始劑。作為光硬化性樹脂組成物所含有之光聚合起始劑,可列舉:2-甲基-1-[4-(甲硫基)苯基]-2-嗎福林基丙烷-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;醯基氧化膦等磷系;9-氧硫等硫系;苯偶醯、9,10-菲醌等苯偶醯系。
光硬化性樹脂組成物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,進而較佳為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可視目的而含有各種添加劑,若進行例示,則可含有穩定劑(例如對苯二酚、對甲氧基苯酚、甲基對苯二酚等聚合抑制劑)、顏料(例如花青藍、雙偶氮黃、胭脂紅6b、色澱
紅C、碳黑、鈦白)等著色劑、填充劑、黏度調整劑等各種添加劑。光硬化性樹脂組成物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聚合物(A)中視需要混合乙烯性不飽和化合物(B),進而混合光聚合起始劑、光起始助劑、添加劑(例如穩定劑、顏料)而進行製造。本發明之光硬化性樹脂組成物藉由照射光而硬化。硬化所使用之光通常為紫外線。
光硬化性樹脂組成物之硬化反應所使用之硬化裝置、及硬化條件並無特別限定,只要為通常之光硬化反應所使用之方法即可。
本發明之光硬化性樹脂組成物之用途並無特別限定。可於墨水(例如光硬化性平版用印刷墨水、絲網印刷墨水、凹版墨水等印刷墨水)、塗料(例如紙用、塑膠用、金屬用、木工用等之塗料,若進行例示,則為套印清漆)、接著劑、光阻劑等技術領域中使用。
含有本發明之光硬化性樹脂組成物之墨水為本發明之墨水,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,墨水之一般之製作方法如下所述。一面將聚合物(A)及穩定劑等於60℃~100℃之溫度下攪拌,一面使其等溶解於乙烯性不飽和化合物(B)中而製作清漆。利用蝶形混合機將顏料、光聚合起始劑、及添加劑攪拌混合於該清漆中後,利用三輥研磨機等進行軋墨,藉此獲得墨水。
又,套印清漆之製作除不使用顏料以外,可以與墨水相同之程序進行。
以下,列舉實施例,對本發明更具體地進行說明,但本發明並不限定於該等實施例。
聚合物(A)之重量平均分子量(Mw)、分子量分佈(Mw/Mn)之測定重量平均分子量(Mw)、分子量分佈(Mw/Mn)係使用GPC而測得。Mw、Mn係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ShodexLF-804×2根串聯連接
流速:1.0mL/min
溫度:40℃
檢測:RID-20A
試樣:使試樣30mg溶解於四氫呋喃3mL中而製成測定用之樣品。
製造例1 異氰尿酸三烯丙酯聚合物1之合成
於3L之可分離式燒瓶中添加異氰尿酸三烯丙酯600g,添加15g之過氧化苯甲醯並於80℃加熱攪拌。反應1小時後,冷卻至室溫(25℃)。冷卻後,於燒瓶中添加甲醇而使聚合物沈澱。將所獲得之聚合物於40℃減壓乾燥16小時(產量:73g,產率:12%,Mw=53,000,Mw/Mn=3.3)。將所獲得之聚合物設為聚合物1,並用於實施例1、4~6。
製造例2 異氰尿酸三烯丙酯聚合物2之合成
將製造例1之反應時間設為1.25小時,除此以外,利用相同之方法進行合成。(產量:84g,產率:14%,Mw=94,000,Mw/Mn=5.3)。將所獲
得之聚合物設為聚合物2,並用於實施例2。
製造例3 異氰尿酸三烯丙酯聚合物3之合成
將製造例1之反應時間設為1.5小時,除此以外,利用相同之方法進行合成。(產量:94g,產率:16%,Mw=126,000,Mw/Mn=6.9)。將所獲得之聚合物設為聚合物3,並用於實施例3。
實施例1~6、比較例1、2
製備下述表1所記載之各組成之光硬化性樹脂組成物,並對光硬化性樹脂組成物之特性進行評價。
表1所示之聚合物1~3以外之成分係如下所述。
又,表1所示之組成量係以重量份計之記法。
DAP樹脂:大阪曹達(股)製造DAISO DAP-A(苯二甲酸二烯丙酯樹脂)
異氰尿酸三烯丙酯(單體)
DTMPTA:Sartomer(股)製造SR355二-三羥甲基丙烷四丙烯酸酯
Irgacure907:BASF JAPAN(股)製造2-甲基-1-[4-(甲硫基)苯基]
-2-嗎福林基丙烷-1-酮
Irganox1076:BASF JAPAN(股)製造3-(3,5-二-第三丁基-4-羥基苯基)丙酸十八烷基酯
1)光硬化性樹脂組成物之溶解性之評價
將各製造例中所獲得之各聚合物1~3、DAP樹脂、異氰尿酸三烯丙酯(單體)、乙烯性化合物及聚合起始劑以表1所記載之各組成量進行添加,進行加熱混合而製備光硬化性樹脂組成物。將各組成物冷卻至室溫(25℃)後,用經過一夜者之外觀是否透明來確認溶解性。將冷卻後外觀亦透明者設為○,將白濁者設為×。將結果示於表2。
2)乾燥性試驗
使用RI測試機將所製備之光硬化性樹脂組成物塗佈於塑膠膜(聚丙烯基材:龍田化學股份有限公司製造無延伸高透明PP片材品名:High P crystal ST-500厚度0.3mm),利用輸出120W/cm之金屬鹵素燈(燈距離11cm,輸送帶速度50m/min)使之硬化。再者,UV硬化裝置係使用EYE GRAPHICS股份有限公司製造之輸送帶型紫外線硬化裝置。通過該輸送帶型紫外線硬化裝置多次直至成為如下狀態,即用手指觸碰塗膜,表面不會附有指紋(不黏著);以該次數來評價乾燥性。將評價結果示於表2。
3)密合性試驗
利用與乾燥性試驗相同之方法將所製備之光硬化性樹脂組成物塗佈於塑膠膜,並使之硬化。將Nichiban公司製造之18mm寬之Sellotape(註冊商標、零件編號:LP-18,黏著力:4.01N/10mm)貼附於所獲得之塗膜,利用大拇指用力擦拭10次後,將Sellotape(註冊商標)朝正上方緩慢剝離。
將完全未剝離者設為○,將完全剝離者設為×。將評價結果示於表2。
如實施例1~6所示,使用使通式[I]所表示之化合物聚合而獲得之聚合物1~3而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DAP樹脂而製備之光硬化性樹脂組成物同等的乾燥性。並且,使用DAP樹脂而製備之比較例1或使用異氰尿酸三烯丙酯(單體)而製備之比較例2之光硬化性樹脂組成物對不易密合之聚丙烯片材的密合性差。
本發明之光硬化性樹脂組成物可用於塑膠基材用之墨水(例如膠版墨水)、塗料、接著劑、光阻劑等。
Claims (4)
- 一種墨水,其含有申請專利範圍第1項之光硬化性樹脂組成物。
- 一種塗料,其含有申請專利範圍第1項之光硬化性樹脂組成物。
- 如申請專利範圍第3項之塗料,其係套印(overprinting)清漆。
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US11149157B2 (en) | 2021-10-19 |
EP3502150A1 (en) | 2019-06-26 |
JP7081486B2 (ja) | 2022-06-07 |
TW201809171A (zh) | 2018-03-16 |
CN109641985B (zh) | 2022-04-22 |
CN109641985A (zh) | 2019-04-16 |
EP3502150A4 (en) | 2020-01-22 |
JPWO2018037912A1 (ja) | 2019-06-20 |
US20190203061A1 (en) | 2019-07-04 |
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