CN110724111A - 液态光引发化合物及其应用 - Google Patents
液态光引发化合物及其应用 Download PDFInfo
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- CN110724111A CN110724111A CN201910136549.6A CN201910136549A CN110724111A CN 110724111 A CN110724111 A CN 110724111A CN 201910136549 A CN201910136549 A CN 201910136549A CN 110724111 A CN110724111 A CN 110724111A
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- Prior art keywords
- photoinitiator
- compound
- formula
- photopolymerizable composition
- photopolymerizable
- Prior art date
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- Granted
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 39
- 239000007788 liquid Substances 0.000 title claims abstract description 34
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 7
- 239000000203 mixture Substances 0.000 claims description 42
- 239000000049 pigment Substances 0.000 claims description 15
- 239000000178 monomer Substances 0.000 claims description 12
- 239000002904 solvent Substances 0.000 claims description 9
- 239000012958 Amine synergist Substances 0.000 claims description 7
- NIXOWILDQLNWCW-UHFFFAOYSA-M acrylate group Chemical group C(C=C)(=O)[O-] NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 6
- 239000003504 photosensitizing agent Substances 0.000 claims description 6
- 150000004056 anthraquinones Chemical class 0.000 claims description 5
- 239000012965 benzophenone Substances 0.000 claims description 5
- 150000008366 benzophenones Chemical class 0.000 claims description 5
- 239000000654 additive Substances 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims description 4
- 241000234282 Allium Species 0.000 claims description 3
- 235000002732 Allium cepa var. cepa Nutrition 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
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- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 8
- 230000000694 effects Effects 0.000 description 7
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
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- OXQHJIGWZNIQDS-UHFFFAOYSA-N 2,2-dimethoxybutane Chemical compound CCC(C)(OC)OC OXQHJIGWZNIQDS-UHFFFAOYSA-N 0.000 description 2
- HEWZVZIVELJPQZ-UHFFFAOYSA-N 2,2-dimethoxypropane Chemical compound COC(C)(C)OC HEWZVZIVELJPQZ-UHFFFAOYSA-N 0.000 description 2
- CDPUNDLWVGKZHS-UHFFFAOYSA-N 2-benzyl-2-(dimethylamino)-1-[4-[2-hydroxyethyl(methyl)amino]phenyl]butan-1-one Chemical compound C=1C=C(N(C)CCO)C=CC=1C(=O)C(CC)(N(C)C)CC1=CC=CC=C1 CDPUNDLWVGKZHS-UHFFFAOYSA-N 0.000 description 2
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- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
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- 238000011056 performance test Methods 0.000 description 2
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- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 230000007696 reproductive toxicity Effects 0.000 description 2
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- 239000011347 resin Substances 0.000 description 2
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- ORZQDTYXWJPWES-UHFFFAOYSA-N 1,3-oxazolidine Chemical class C1COCN1.C1COCN1 ORZQDTYXWJPWES-UHFFFAOYSA-N 0.000 description 1
- ILBBNQMSDGAAPF-UHFFFAOYSA-N 1-(6-hydroxy-6-methylcyclohexa-2,4-dien-1-yl)propan-1-one Chemical compound CCC(=O)C1C=CC=CC1(C)O ILBBNQMSDGAAPF-UHFFFAOYSA-N 0.000 description 1
- BTJPUDCSZVCXFQ-UHFFFAOYSA-N 2,4-diethylthioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(CC)=CC(CC)=C3SC2=C1 BTJPUDCSZVCXFQ-UHFFFAOYSA-N 0.000 description 1
- IWSZDQRGNFLMJS-UHFFFAOYSA-N 2-(dibutylamino)ethanol Chemical compound CCCCN(CCO)CCCC IWSZDQRGNFLMJS-UHFFFAOYSA-N 0.000 description 1
- PTTPXKJBFFKCEK-UHFFFAOYSA-N 2-Methyl-4-heptanone Chemical compound CC(C)CC(=O)CC(C)C PTTPXKJBFFKCEK-UHFFFAOYSA-N 0.000 description 1
- UHFFVFAKEGKNAQ-UHFFFAOYSA-N 2-benzyl-2-(dimethylamino)-1-(4-morpholin-4-ylphenyl)butan-1-one Chemical compound C=1C=C(N2CCOCC2)C=CC=1C(=O)C(CC)(N(C)C)CC1=CC=CC=C1 UHFFVFAKEGKNAQ-UHFFFAOYSA-N 0.000 description 1
- GDALETGZDYOOGB-UHFFFAOYSA-N Acridone Natural products C1=C(O)C=C2N(C)C3=CC=CC=C3C(=O)C2=C1O GDALETGZDYOOGB-UHFFFAOYSA-N 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- XOBKSJJDNFUZPF-UHFFFAOYSA-N Methoxyethane Chemical compound CCOC XOBKSJJDNFUZPF-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- 238000010546 Norrish type I reaction Methods 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 206010058667 Oral toxicity Diseases 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 1
- AUNAPVYQLLNFOI-UHFFFAOYSA-L [Pb++].[Pb++].[Pb++].[O-]S([O-])(=O)=O.[O-][Cr]([O-])(=O)=O.[O-][Mo]([O-])(=O)=O Chemical compound [Pb++].[Pb++].[Pb++].[O-]S([O-])(=O)=O.[O-][Cr]([O-])(=O)=O.[O-][Mo]([O-])(=O)=O AUNAPVYQLLNFOI-UHFFFAOYSA-L 0.000 description 1
- FZEYVTFCMJSGMP-UHFFFAOYSA-N acridone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3NC2=C1 FZEYVTFCMJSGMP-UHFFFAOYSA-N 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 238000011047 acute toxicity test Methods 0.000 description 1
- 239000005456 alcohol based solvent Substances 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 229910052793 cadmium Inorganic materials 0.000 description 1
- BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 description 1
- CJOBVZJTOIVNNF-UHFFFAOYSA-N cadmium sulfide Chemical compound [Cd]=S CJOBVZJTOIVNNF-UHFFFAOYSA-N 0.000 description 1
- 229950005499 carbon tetrachloride Drugs 0.000 description 1
- 229960001701 chloroform Drugs 0.000 description 1
- 229910000423 chromium oxide Inorganic materials 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- NNSIWZRTNZEWMS-UHFFFAOYSA-N cobalt titanium Chemical compound [Ti].[Co] NNSIWZRTNZEWMS-UHFFFAOYSA-N 0.000 description 1
- 150000004696 coordination complex Chemical class 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 125000006575 electron-withdrawing group Chemical group 0.000 description 1
- 239000003759 ester based solvent Substances 0.000 description 1
- 239000004210 ether based solvent Substances 0.000 description 1
- 230000005281 excited state Effects 0.000 description 1
- 229930003935 flavonoid Natural products 0.000 description 1
- 150000002215 flavonoids Chemical class 0.000 description 1
- 235000017173 flavonoids Nutrition 0.000 description 1
- 230000004927 fusion Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 239000005453 ketone based solvent Substances 0.000 description 1
- MOUPNEIJQCETIW-UHFFFAOYSA-N lead chromate Chemical compound [Pb+2].[O-][Cr]([O-])(=O)=O MOUPNEIJQCETIW-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- CRVGTESFCCXCTH-UHFFFAOYSA-N methyl diethanolamine Chemical compound OCCN(C)CCO CRVGTESFCCXCTH-UHFFFAOYSA-N 0.000 description 1
- 238000003801 milling Methods 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 231100000418 oral toxicity Toxicity 0.000 description 1
- 230000008520 organization Effects 0.000 description 1
- 125000000160 oxazolidinyl group Chemical group 0.000 description 1
- 238000005498 polishing Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
- G03F7/028—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with photosensitivity-increasing substances, e.g. photoinitiators
- G03F7/031—Organic compounds not covered by group G03F7/029
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/04—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/04—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D263/06—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hydrocarbon radicals, substituted by oxygen atoms, attached to ring carbon atoms
-
- 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
-
- 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
- C08F2/50—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
-
- 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
- C08F20/00—Homopolymers and 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
- C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
- C08F20/10—Esters
- C08F20/12—Esters of monohydric alcohols or phenols
- C08F20/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
- C08F20/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/06—Ethers; Acetals; Ketals; Ortho-esters
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/07—Aldehydes; Ketones
- C08K5/08—Quinones
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/35—Heterocyclic compounds having nitrogen in the ring having also oxygen in the ring
- C08K5/353—Five-membered rings
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/49—Phosphorus-containing compounds
- C08K5/51—Phosphorus bound to oxygen
- C08K5/53—Phosphorus bound to oxygen bound to oxygen and to carbon only
- C08K5/5397—Phosphine oxides
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- General Physics & Mathematics (AREA)
- Polymerisation Methods In General (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Abstract
Description
技术领域
本发明是关于一种液态光引发化合物及其于可光聚合的组合物的应用。
背景技术
光引发剂(photoinitiator)为一种可吸收例如可见光或紫外光能量而达激发态,并发生罗氏一型(Norrish Type I)光反应,分裂出自由基,从而引发单体或寡聚体交联聚合,达固化效果的物质。
Ciba公司于1990年研发出第一支适用于深色UV油墨的固态引发剂产品“369”(相关专利:US 5,077,402),其化学结构显示如下,属于罗氏一型(Norrish Type I)光引发剂,会分裂出自由基,以引发单体或寡聚体交联聚合,达固化效果。
[369]
369的光引发性能优异,本身及照光后均不产生气味,但是于一般UV油墨中的溶解度不佳,必须通过研磨及升温等工序来促进溶解。369在用量多于4重量%时,即存在有析出的风险,尤其在低温使用环境如寒带地区时,析出现象更为明显。最近369被欧盟列为具有最高级生殖毒性的物质,此议题持续被探讨并受市场关注,使其存在被禁用的风险。
Ciba公司继369后,推出具如下结构的固态光引发剂产品“379”(相关专利:US 7,247,659B2)。379虽然在一些单体及树脂内的溶解度有所改善,但仍属固态光引发剂,还是必须经过加热及研磨工序才能应用至油墨配方中,使用上仍不方便。此外,379也存在生殖毒性的问题。
[379]
近年来,由于数位印刷(digital printing)、凹版印刷(gravure printing)、柔版印刷(flexographic printing)等印刷技术的蓬勃发展,低黏度油墨的需求日渐增加。由于低黏度油墨通常无法提供足够的剪切力来进行固态光引发剂所需要的研磨分散程序,因此低黏度油墨偏好使用更容易分散且溶解度较佳的液态光引发剂。
液态光引发剂的实例包括记载于US 5,077,402中的如下化合物93、95、96及100,但这些化合物在黑色油墨系统的光速度慢,而且使用后还有气味,因此从未被商品化。
[US 5,077,402]
[TW I277834实施例3]
[化合物I]
[TW I564276的化合物IIa]
因此,目前可用于深色及黑色油墨的液态光引发剂均不完美,各有其缺点。
发明内容
鉴于现有光引发剂的不足,本发明提供一种恶唑烷类(Oxazolidine)衍生物的光引发剂,其具有(1)于50℃的低温下即呈液态、(2)光速度近似369、(3)本身及照光后不产生气味、及(4)无口服急毒性等四大优点,一举解决之前用于黑色油墨系统的液态光引发剂所有问题。除此之外,其还有初始颜色浅、纯度高等优点,可充分满足业界对于液态光引发剂要求。因此,本发明至少涉及以下将描述的发明目的。
于此须说明,虽然US 5,077,402及US 7,732,504B2公开的光引发剂涵盖具有恶唑烷结构的光引发剂,但并未教示本发明的光引发剂,且本发明所属技术领域普通技术人员基于US 5,077,402及US 7,732,504B2的广泛教示并无从预期本发明光引发剂的优异功效,包括于50℃的低温下即呈液态、光速度佳、不具气味及毒性等,尤其无法预期本发明光引发剂不具口服急毒性的结果。
本发明的一目的在于提供一种液态光引发化合物,其具有下式I的结构:
[式I]
于式I中,R1与R2各自独立为H或C1-C3烷基,且R3为H或甲基。该C1-C3烷基包括甲基、乙基、正丙基及异丙基。
于部分实施方案中,前述化合物具有下式Ia的结构:
[式Ia]
本发明的另一目的是关于一种前述化合物作为光引发剂的用途。
本发明的又一目的在于提供一种可光聚合的组合物,包含:
第一光引发剂,其是前述的化合物;
一可光聚合成分;以及视需要的溶剂。
于部分实施方案中,可光聚合成分是含烯键的不饱和单体、含烯键的不饱和寡聚体或其组合。该含烯键的不饱和单体的实例包括丙烯酸酯系单体,该含烯键的不饱和寡聚体的实例包括丙烯酸酯系寡聚体。
于本发明的部分实施方案中,可光聚合的组合物还包含选自以下群组的光敏剂:二苯甲酮类(benzophenones)、氧硫类(thioxanthones)、米其勒酮类(Michler’sketones)、蒽醌(anthraquinone)及其组合。
于部分实施方案中,可光聚合的组合物还包含选自以下群组的添加剂:颜料、胺综效剂(amine synergist)及其组合。
于部分实施方案中,以可光聚合的组合物的总重量计,第一光引发剂的含量为0.1重量%至15重量%。
为使本发明的上述目的、技术特征及优点明显易懂,下文以部分具体实施方案进行详细说明。
具体实施方式
以下将具体地描述根据本发明的部分具体实施方案;但是,在不背离本发明的精神下,本发明还可以多种不同形式的方案来实践,不应将本发明保护范围解释为限于说明书所陈述的具体实施方案。
除非另有说明,于本说明书中(尤其是在后述专利申请范围中)所使用的「一」、「该」及类似用语应理解为包含单数及复数形式。
除非另有说明,于本说明书中(尤其是在权利要求书中),所使用的“第一”、“第二”及类似用语仅用区隔所描述的元件或成分,本身并无特殊涵义,且非意欲指代先后顺序。
除非另有说明,于本说明书中(尤其是在权利要求书中),所述烷基是包含具有直链、支链、环状或其组合的结构的各种烷基。
液态光引发化合物
本发明的液态光引发化合物具有下式I的结构:
[式I]
于式I中,R1及R2各自独立为H或C1-C3烷基,以及R3为H或甲基。于本发明的部分实施方案中,R1及R2各自独立为甲基、乙基、正丙基或异丙基,且R3为H。于后附实施例中,该第一光引发剂具有下式Ia的结构:
[式Ia]
本发明液态光引发化合物的合成方式将于后附实施例中提供具体例示说明,于此不另赘述。
液态光引发化合物的应用
本发明的液态光引发化合物,于50℃的低温下即呈液态,可作为液态光引发剂,引发可光聚合的单体或寡聚体发生交联聚合反应而固化,且本发明的液态光引发化合物所具备的特殊结构出乎意料地使得该化合物展现出迥异于现有光引发剂的特性而具有诸多优点。具体而言,本发明的液态光引发化合物具有优异光速度性能(photo speedperformance),且具有于50℃的低温下即呈液态、溶解性优异、色度低等特点,添加于可光聚合系统时对系统黏度的影响甚微,具长时间储存稳定性,因此尤其可应用于低黏度UV油墨(例如黏度低于1000厘泊(cps)的油墨)、浅色UV油墨、彩色光阻(Color resist)、黑色矩阵(Black matrix)及阻焊(Solder mask)。此外,本发明的液态光引发化合物的制造纯度高,可符合各国化学物质法规注册规范。
因此,本发明也提供一种可光聚合的组合物,包含第一光引发剂、可光聚合成分以及视需要的溶剂,其中第一光引发剂是具式I的化合物。
该可光聚合成分的种类并无特殊限制,可为任何在光引发剂存在下可光聚合的物质,包括常用于可光聚合系统如UV油墨的可光聚合成分。于本发明的部分实施方案中,该可光聚合成分是含烯键的不饱和单体、含烯键的不饱和寡聚体或其组合。含烯键的不饱和单体的实例包括但不限于丙烯酸酯系单体,且含烯键的不饱和寡聚体的实例包括但不限于丙烯酸酯系寡聚体。
该视需要的溶剂可为任何可溶解或分散组合物各成分,但不与之反应的溶剂,包括常用于可光聚合系统如UV油墨的溶剂。溶剂的实例包括但不限于:水;脂肪烃系溶剂,例如二氯甲烷、三氯甲烷、四氯甲烷、正己烷及环己烷;芳香烃系溶剂,例如甲苯、苯及二甲苯;酮系溶剂,例如丙酮、甲基乙基酮、异丁酮及环己酮;酯系溶剂,例如乙酸乙酯及乙酸丁酯;醇系溶剂,例如甲醇、乙醇、正丙醇及异丙醇;及醚系溶剂,例如二甲醚、二乙醚及甲基乙基醚。
于本发明的可光聚合的组合物中,第一光引发剂的含量并无特殊限制,可由本领域普通技术人员视需要进行调配。一般而言,为获致所欲的光聚合固化效果,该可光聚合的组合物的总重量计,第一光引发剂的含量可为但不限于0.1重量%至15重量%,例如1重量%、2重量%、3重量%、4重量%、5重量%、6重量%、7重量%、8重量%或9重量%。
除第一光引发剂外,本发明的可光聚合的组合物也可视需要包含其他有助于光引发效果的成分,例如光敏成分或其他光引发成分。因此,于本发明的部分实施方案中,可光聚合的组合物进一步包含第二光引发剂、光敏剂或其组合。
第二光引发剂可为除第一光引发剂外的任何光引发成分,其实例包括但不限于酰基膦氧化物、9,10-二烷氧基葱、或其组合。光敏剂的种类也无特殊限制,其实例包括但不限于二苯甲酮类、氧硫 类、米其勒酮类、蒽醌或其组合。于后附实施例中,可光聚合的组合物中使用2,4-二乙基氧硫(产品名:DETX)作为光敏剂。第二光引发剂与光敏剂的含量并无特殊限制,可由本领域普通技术人员视需要进行调配。
本发明的可光聚合的组合物中可视需要进一步包含一种或多种添加剂,以使得组合物固化后所得的产物可具备所欲的特性。举例言之,可添加颜料以赋予产物颜色或可添加胺综效剂,以提升固化表现,例如提高组合物的表面固化速度及干燥后的镜面效果。颜料的实例包括但不限于二氧化钛、碳黑、镉红、钼红、铬黄、镉黄、钛黄、氧化铬、钛钴绿、青蓝、钴蓝、偶氮系颜料、酞青颜料(phthalocyanine pigments)、煃吖啶酮系颜料(quinacridonebased pigments)、异吲哚啉酮系颜料(isoindolinone based pigments)、苝系颜料(perylene based pigments)、硫靛系颜料(thio indigo based pigments)及金属错合物颜料。于本说明书中,胺综效剂是本发明所属技术领域普通技术人员所熟知的添加剂,泛指可促进光引发反应的反应型胺,例如低分子量三级胺。胺综效剂的实例包括不限于甲基二乙醇胺、二丁基乙醇胺、三乙基胺、三乙醇胺,其商购可得的产品包括可购自奇钛科技股份有限公司的115、EPD、OPD等。
现以下列具体实施方案进一步例示说明本发明。
实施例
实施例1:具式Ia结构的液态光引发化合物的制备
取250毫升三颈圆底瓶,于室温下依序加入34公克2-(二甲基胺基)-1-[4-[(2-羟乙基)甲基胺基]苯基]-2-(苯基甲基)-1-丁酮(CAS862589-48-8;合成方式可参照TWI277834)、13.0公克2,2-二甲氧基丁烷(CAS 3453-99-4)、0.17公克PTSA(对甲苯磺酸)以及100毫升甲苯(toluene)以进行如下反应,反应过程中蒸发除去所产生的甲醇。
以高效能液相层析仪(High Performance Liquid Chromatography,HPLC)确认反应完成后,以17克纯水萃取三次,收集有机层并在真空下进行浓缩,获得具式Ia结构的液态光引发化合物(下称『光引发化合物Ia』)的淡黄色黏稠状液体,产率为95%。
对光引发化合物Ia进行核磁共振分析,结果如下:
核磁共振分析:1H NMR(500MHz,CDCl3):0.70(t,J=7.5Hz,3H),0.82(t,J=7.5Hz,3H),1.85-1.89(m,1H),1.94-1.99(m,1H),2.04-2.09(m,1H),2.13-2.18(m,1H),2.36(s,6H),3.16-3.23(m,2H),3.18(d,J=14.0Hz,1H),3.22(d,J=14.0Hz,1H),4.06-4.10(m,1H),4.12-4.26(m,1H),6.60(d,J=9.0Hz,2H),7.16-7.28(m,6H),8.34(d,J=9.0Hz,2H)
13C NMR(500MHz,CDCl3):7.7,9.8,23.8,27.8,31.0,35.5,39.1,48.4,63.2,73.8,96.2,111.5,125.8,125.9,127.9,131.3,132.2,139.6,147.1,201.6
实施例2:具式Ib结构的液态光引发化合物的制备
取250毫升三颈圆底瓶,于室温下依序加入34克2-(二甲基胺基)-1-[4-[(2-羟乙基)甲基胺基]苯基]-2-(苯基甲基)-1-丁酮、12.0克2,2-二甲氧基丙烷(CAS 77-76-9)、0.17克PTSA(对甲苯磺酸)以及100毫升甲苯(toluene)以进行如下反应,反应过程中蒸发除去所产生的甲醇。
以高效能液相层析仪(HPLC)确认反应完成后,以17克纯水萃取三次,收集有机层并在真空下进行浓缩,获得具式Ib结构的液态光引发化合物(下称『光引发化合物Ib』)的淡黄色黏稠状液体,产率为93%。
对光引发化合物Ib进行核磁共振分析,结果如下:
核磁共振分析:1H NMR(500MHz,CDCl3):0.69(t,J=7.5Hz,3H),1.64(s,6H),1.83-1.90(m,1H),2.02-2.17(m,1H),2.36(s,6H),3.17(d,J=14.0Hz,1H),3.22(d,J=14.0Hz,1H),3.53(t,J=6.5Hz,2H),4.11(t,J=6.5Hz,2H),6.60(d,J=9.0Hz,2H),7.15-7.28(m,6H),8.35(d,J=9.0Hz,2H)
13C NMR(500MHz,CDCl3):9.8,25.4,27.8,35.5,39.1,47.8,62.9,73.9,93.9,111.8,125.8,125.9,127.9,131.3,132.2,139.6,147.0,201.6
实施例3:溶解性测试
以如下比例配制混合物I至III。接着于混合物I至III中分别添加6重量份的光引发剂369(购自Ciba公司)、光引发剂919(购自奇钛科技股份有限公司)及光引发化合物Ia,并将所得混合物于室温下超音波震荡1小时,观察其溶解情形,并将结果记录于下表1。
表1:于室温下超音波震荡1小时后的溶解情形
实施例4:黏度变化测试
表2:暴露于0℃环境下七天前后所测得的黏度(厘泊)
如表2所示,光引发化合物Ia对于混合物的黏度影响最低。此外,在暴露于0℃环境下七天后,添加光引发化合物Ia的混合物其黏度变化情形大致与未添加光引发剂的一致,且无析出问题。此显示光引发化合物Ia的溶解度与树脂相容性优于369,实用性佳。
实施例5:光速度性能测试
将黑色柔版印刷油墨配方(black flexo formulation;含Oligomer6325-100、EM2411及碳黑;黏度:1750厘泊)与光引发剂混合,以进行光速度性能测试。具体言之,混合100重量份的黑色柔版印刷油墨配方和2重量份DETX(光引发剂;奇钛科技股份有限公司),并于所得混合物中分别添加6重量份的光引发剂369、光引发剂998(购自奇钛科技股份有限公司)、光引发剂919及光引发化合物Ia,以完成黑色柔版印刷油墨配方。接着将所得混合物涂布于可印刷的珠光膜上(湿膜膜厚:25.15微米),并暴露在UV灯(Fusion F300;D-bulb;300瓦/英寸)下进行固化,观察其光速度性能。结果记录于下表3。
表3:光引发剂的光速度性能
实施例6:光引发剂用量测试
将不含光引发剂的市售成品黑色柔版印刷油墨(由东周化学工业股份有限公司提供)与光引发剂混合,以进行光速度性能测试,并比较光引发化合物Ia添加量对光速度性能的影响。具体言之,混合100重量份的黑色柔版印刷油墨配方和2重量份DETX(光引发剂;奇钛科技股份有限公司),并于所得混合物中分别以不同用量添加光引发剂369及光引发化合物Ia,如下表4所示,以完成黑色柔版印刷油墨配方。接着将所得混合物涂布于经附着力处理(primer)的PET上(干膜膜厚:5微米),并暴露在LED UV灯(波长365奈米;4瓦/英寸)下进行固化,观察其光速度性能。结果记录于下表4。
表4:光引发剂在不同添加量下的光速度性能
固化状况描述:
如表4所表示,测试的黑色柔版印刷油墨是一种难以进行光固化的油墨系统,但可通过增加光引发剂的添加量以达到更好的光固化效率。然而,添加8重量份的光引发剂369时,如同先前溶解度实验的结果,光引发剂并无法完全溶解于测试油墨系统中,故无法进行后续光速度测试。相较之下,光引发化合物Ia在增加添加量时,即使增加到12重量份也无溶解度问题,且随着添加量由4重量份增加至8重量份时,光固化速度大幅改善,并在添加量为12重量份时,照光一次即完成充分固化。
实施例7:口服急毒性
根据经济合作与发展组织(OECD)准则423口服急毒性测试方法进行光引发剂369、998、919及光引发化合物Ia的半致死剂量(LD50;Median lethal dose)测试,结果记录如下表5。
表5:光引发剂的口服急毒半致死剂量LD50
实施例1至7的结果显示,本发明的液态光引发化合物具有优异光速度性能,且具有于50℃的低温下即呈液态、溶解性优异、色度低、无口服急毒性等特点,添加于可光聚合系统时对系统黏度的影响甚微,具长时间储存稳定性,尤其可应用于低黏度UV油墨、浅色UV油墨、彩色光阻、黑色矩阵及阻焊。
上述实施例仅为例示性说明本发明的原理及其功效,并阐述本发明的技术特征,而非用于限制本发明的保护范畴。任何本领域技术人员在不违背本发明的技术原理及精神下,可轻易完成的改变或安排,均属本发明所主张的范围。因此,本发明的权利保护范围如权利要求书所列。
Claims (11)
2.如权利要求1所述的化合物,其特征在于,其中R1及R2各自独立为甲基、乙基、正丙基或异丙基。
3.如权利要求2所述的化合物,其特征在于,其具有下式Ia的结构:
[式Ia]
4.一种如权利要求1至3中任一项所述的化合物,其特征在于,该化合物作为光引发剂使用。
5.一种可光聚合的组合物,其特征在于,包含:
第一光引发剂,其是如权利要求1至3中任一项所述的化合物;
一可光聚合成分;以及
视需要的溶剂。
6.如权利要求5所述的可光聚合的组合物,其特征在于,其中该可光聚合成分是含烯键的不饱和单体、含烯键的不饱和寡聚体或其组合。
7.如权利要求6所述的可光聚合的组合物,其特征在于,其中该可光聚合成分是丙烯酸酯系单体、丙烯酸酯系寡聚体或其组合。
10.如权利要求5所述的可光聚合的组合物,其特征在于,还包含选自以下群组的添加剂:颜料、胺综效剂(amine synergist)及其组合。
11.如权利要求5所述的可光聚合的组合物,其特征在于,其中以该可光聚合的组合物的总重量计,第一光引发剂的含量为0.1重量%至15重量%。
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