CN108957950B - UV (ultraviolet) photocuring composition containing fluorenylaminoketone photoinitiator - Google Patents
UV (ultraviolet) photocuring composition containing fluorenylaminoketone photoinitiator Download PDFInfo
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- CN108957950B CN108957950B CN201711472418.2A CN201711472418A CN108957950B CN 108957950 B CN108957950 B CN 108957950B CN 201711472418 A CN201711472418 A CN 201711472418A CN 108957950 B CN108957950 B CN 108957950B
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- 239000000203 mixture Substances 0.000 title claims abstract description 84
- 238000000016 photochemical curing Methods 0.000 title abstract description 11
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- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 49
- 125000000217 alkyl group Chemical group 0.000 claims description 26
- 239000000976 ink Substances 0.000 claims description 25
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 15
- 229910052757 nitrogen Inorganic materials 0.000 claims description 15
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- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 12
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- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 10
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- 125000003358 C2-C20 alkenyl group Chemical group 0.000 claims description 7
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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 claims description 5
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- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 3
- MZVQCMJNVPIDEA-UHFFFAOYSA-N [CH2]CN(CC)CC Chemical group [CH2]CN(CC)CC MZVQCMJNVPIDEA-UHFFFAOYSA-N 0.000 claims description 3
- 125000002947 alkylene group Chemical group 0.000 claims description 3
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Natural products C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
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- DZBUGLKDJFMEHC-UHFFFAOYSA-N benzoquinolinylidene Natural products C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 3
- 229930016911 cinnamic acid Natural products 0.000 claims description 3
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- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 3
- 238000006471 dimerization reaction Methods 0.000 claims description 3
- LDLDYFCCDKENPD-UHFFFAOYSA-N ethenylcyclohexane Chemical compound C=CC1CCCCC1 LDLDYFCCDKENPD-UHFFFAOYSA-N 0.000 claims description 3
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
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Classifications
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- 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
-
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- C09D167/00—Coating compositions based on polyesters obtained by reactions forming a carboxylic ester link in the main chain; Coating compositions based on derivatives of such polymers
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- 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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Abstract
The invention discloses a UV (ultraviolet) photocuring composition containing a fluorenylaminoketone photoinitiator. The UV light-curable composition includes: a dilute unsaturated photopolymerizable compound and a photoinitiator; wherein, the photoinitiator comprises a compound with a structure shown as a general formula (I) or a derivative compound thereof,
Description
Technical Field
The invention relates to the technical field of novel UV (ultraviolet) light radiation free radical polymerization materials, in particular to a UV light curing composition containing a fluorenylaminoketone photoinitiator.
Background
In 1988, patent EP284561 disclosed the use of α -aminoketones as photoinitiators, and finally 2-dimethylamino-2-benzyl-1- (4-morpholinophenyl) -1-butanone was chosen as a commercial product. However, the photoinitiators have the obvious disadvantages of low solubility, difficult formulation and poor low temperature stability of the formulated compositions, especially at concentrations above 5%. In 2001, patent document JP2001348412A discloses a liquid curable resin composition containing 2-methyl-1- [4- (methylthio) phenyl ] -2- (4-morpholinyl) -1-propanone (trade name Irgacure 907) as a photoinitiator component. However, since the aromatic ring system in the structure of the compound contains a methylthio group, there are inevitable problems such as generation of a bad smell after photocleavage and severe yellowing of the cured product, which are not applicable in the fields of food packaging, varnish coatings, white inks, and the like.
In view of the above drawbacks, in recent years, there have been reports on the research on Irgacure 907 photoinitiator substitutes, for example, patent application No. CN101724099 discloses a series of α -aminoketones of biphenyl derivatives, in which 1- ([1, 1-biphenyl ] -4-yl) -2-methyl-2-morpholinopropan-1-one is an effective substitute for Irgacure 907. The compound does not contain sulfur element, and shows excellent yellowing resistance when being applied to a UV free radical photopolymerization curing system, and no bad smell is generated after illumination decomposition. However, in practical application, the photoinitiator is found to be not a perfect substitute because of poor solubility, easy sublimation and pollution to production equipment and light sources.
These problems have attracted much attention in the industry, and the problems of odor, yellowing, toxicity and the like of the photoinitiator greatly limit the application of UV coatings and UV inks in various fields of furniture, electric appliances, automobile interiors, cigarettes, food, medicines, cosmetics and the like. Development of a photocurable composition that can effectively solve the above problems and is economically and environmentally competitive is one of the important issues facing the industrial field.
Disclosure of Invention
The invention aims to provide a UV photocuring composition containing a fluorenylaminoketone photoinitiator so as to improve the yellowing resistance of the UV photocuring composition.
In order to achieve the above object, according to one aspect of the present invention, there is provided a UV light-curable composition containing a fluorenylaminoketone photoinitiator. The UV light-curable composition includes: a dilute unsaturated photopolymerizable compound and a photoinitiator; wherein, the photoinitiator comprises a compound with a structure shown as a general formula (I) or a derivative compound thereof,
wherein,
a represents hydrogen, halogen, nitro, C1-C20Straight or branched alkyl of (2), C3-C10Alkylcycloalkyl of (A), C4-C10An alkylcycloalkyl or cycloalkylalkyl group of,
-COR6or-CO-CR2R3R4Group, wherein, optionally, -CH2-by O, N, S or C (═ O);
R1represents hydrogen, halogen, C1-C20Straight or branched alkyl of (2), C4-C20Cycloalkylalkyl or C2-C20Alkenyl of (2), optionally, R1In (C-CH)2-substituted by O, N, S or C (═ O), R1Can form a ring;
R2and R3Each independently represents C1-C20Straight or branched alkyl of (2), C3-C20Cycloalkyl of, C4-C20Cycloalkylalkyl of (C)4-C20Alkylcycloalkyl of (A), C6-C20Aryl radical, C6-C20Wherein one or more hydrogens in these groups may be substituted independently of each other by alkyl, halogen, hydroxy, nitro, and optionally, R2And R3In (C-CH)2-is substituted by O, N, S or C (═ O),and R is2And R3Can form a ring with each other;
R4represents N-morpholinyl, N-piperidinyl, N-pyrrolyl or N-dialkyl, wherein one or more of the hydrogen atoms of these radicals may be substituted by halogen, hydroxy;
R5、R5' represents independently of one another C1-C20Linear or branched alkyl of (2), C4-C20Cycloalkyl of, C2-C20Alkenyl of (C)6-C20Aryl of (C)6-C20Wherein one or more hydrogens in these groups may be substituted independently of each other by alkyl, halogen, hydroxy, nitro, and optionally-CH in these groups2-may be substituted by-O-; or R5And R5' may be linked to each other or form a five-or six-membered ring through-O-, -S-, -NH-;
R6represents unsubstituted or substituted by one or more C1-C20Alkyl, halogen, cyano, SR7、OR8Substituted phenyl;
R7and R8Independently of one another, represents hydrogen, C1-C20Linear or branched alkyl.
Further, the amount of the rare unsaturated photopolymerizable compound is 5 to 95 parts by mass, and the amount of the photoinitiator is 0.05 to 15 parts by mass.
Further, the amount of the rare unsaturated photopolymerizable compound is 10 to 90 parts by mass, and the amount of the photoinitiator is 1 to 10 parts by mass.
Further, the photoinitiator having the structure represented by the general formula (I) is selected from the group consisting of
Further, the derivative compounds of the photoinitiators having the structure shown in formula (I) include derivative compounds obtained by substitution of their branches or linkage to each other while maintaining the main structure of the compounds of formula (I).
Further, the derivative compound has a compound represented by the general formula (II) or (III):
Further, the derivative compound is
Further, the photoinitiator having a structure represented by general formula (I) or a derivative compound thereof is a mixture of two or more compounds.
Further, the ethylenically unsaturated photopolymerizable compound is a monomeric compound or an oligomeric compound.
Further, the ethylenically unsaturated photopolymerizable compound is a compound containing one carbon-carbon double bond, preferably an acrylate compound or a methacrylate compound; or the rare unsaturated photopolymerizable compound is a compound containing two or more carbon-carbon double bonds, preferably an alkyl diol, an acrylate or methacrylate of a polyol, or an unsaturated polyester of a polyester polyol, a polyether polyol, an epoxy polyol, an acrylate of a polyurethane polyol, a vinyl ether, and an unsaturated dicarboxylic acid polyol.
Further, when the UV light-curable composition is used as a UV resist ink or a UV solder resist ink, at least one compound of the used rare unsaturated photopolymerizable compounds contains an alkali soluble group, preferably a carboxyl group-containing resin.
Further, the carboxyl group-containing resin is a (meth) acrylate, an ethylenically unsaturated carboxylic acid, or a (meth) acrylate-based polymer;
preferably, the (meth) acrylic acid ester is one or more selected from the group consisting of methyl (meth) acrylate, ethyl (meth) acrylate, butyl (meth) acrylate, cyclohexyl (meth) acrylate, benzyl (meth) acrylate, diethylaminoethyl (meth) acrylate, dimethylaminoethyl (meth) acrylate, hydroxyethyl (meth) acrylate, hydroxypropyl (meth) acrylate, furfuryl (meth) acrylate, glycidyl (meth) acrylate;
preferably, the ethylenically unsaturated carboxylic acid is one or more selected from the group consisting of acrylic acid, methacrylic acid, vinylbenzoic acid, maleic acid, alkyl maleate, fumaric acid, itaconic acid, crotonic acid, cinnamic acid, acrylic acid dimer, addition product of monomer having hydroxyl group and cyclic anhydride, ω -carboxy-polycaprolactone- (meth) acrylate, more preferably (meth) acrylic acid;
preferably, the (meth) acrylate-based polymer is one or more selected from the group consisting of (meth) acrylamide, n-butyl (meth) acrylate, styrene, vinyl naphthalene, (meth) acrylonitrile, vinyl acetate, and vinyl cyclohexane.
Further, the UV light curing composition further comprises other photo-initiators, preferably, the other photo-initiators are selected from one or more of the group consisting of benzophenone, benzildimethyl ketal, 2-hydroxy-2-methyl-1-phenyl-acetone, 1-hydroxy-cyclohexyl-phenyl-ketone, isopropylthioxanthene, (2,4, 6-trimethyl-benzoyl) diphenylphosphine oxide and bis (2,4, 6-trimethylbenzoyl) -phenylphosphine oxide.
Further, the UV light-curable composition further includes a sensitizer; preferably, the sensitizer is a pyrazoline compound, an acridine compound, an anthracene compound, a coumarin compound or a tertiary amine compound; more preferably, the amount of the sensitizer is 0 to 5 parts by mass, and still more preferably, the amount of the sensitizer is 0 to 2 parts by mass.
Further, the UV light-curing composition also comprises a coloring agent, wherein the coloring agent is an inorganic pigment or an organic pigment, and the amount of the coloring agent is 0-50 parts by mass, preferably 0-20 parts by mass.
Further, the UV light-curable composition further comprises additives including one or more of surfactants, wetting agents, dispersants, rheology modifiers, defoamers, or storage enhancers; preferably, the additive is used in an amount of 0 to 5 parts by mass, and more preferably, the additive is used in an amount of 0 to 3 parts by mass.
According to another aspect of the present invention, there is provided a use of any one of the above UV light-curable compositions in UV coatings and UV inks.
Further, the UV ink includes UV resist ink, flexo ink, offset ink, and the like. The UV photocuring composition containing the fluorenylaminoketone photoinitiator has high sensitivity, no residue after development, good pattern integrity, no odor or low odor of a coating after curing, and excellent yellowing resistance.
Detailed Description
It should be noted that the embodiments and features of the embodiments in the present application may be combined with each other without conflict. The present invention will be described in detail with reference to examples.
According to a typical embodiment of the present invention, there is provided a UV light-curable composition containing a fluorenylaminoketone photoinitiator. The UV light-curable composition includes: a dilute unsaturated photopolymerizable compound and a photoinitiator; wherein, the photoinitiator comprises a compound with a structure shown as a general formula (I) or a derivative compound thereof,
wherein,
a represents hydrogen, halogen, nitro, C1-C20Straight or branched alkyl of (2), C3-C10Alkylcycloalkyl of (A), C4-C10An alkylcycloalkyl or cycloalkylalkyl group of,
-COR6or-CO-CR2R3R4Group, wherein, optionally, -CH2-by O, N, S or C (═ O);
R1represents hydrogen, halogen, C1-C20Straight or branched alkyl of (2), C4-C20Cycloalkylalkyl or C2-C20Alkenyl of (2), optionally, R1In (C-CH)2-substituted by O, N, S or C (═ O), R1Can form a ring;
R2and R3Each independently represents C1-C20Straight or branched alkyl of (2), C3-C20Cycloalkyl of, C4-C20Cycloalkylalkyl or C4-C20Alkylcycloalkyl of (A), C6-C20Aryl radical, C6-C20Wherein one or more hydrogens in these groups may be substituted independently of each other by alkyl, halogen, hydroxy, nitro, and optionally, R2And R3In (C-CH)2-is substituted by O, N, S or C (═ O), and R2And R3Can form a ring with each other;
R4represents N-morpholinyl, N-piperidinyl, N-pyrrolyl or N-dialkyl, wherein one or more of the hydrogen atoms of these radicals may be substituted by halogen, hydroxy;
R5、R5' represents independently of one another C1-C20Linear or branched alkyl of (2), C4-C20Cycloalkyl of, C2-C20Alkenyl of (C)6-C20Aryl of (C)6-C20Wherein one or more hydrogens in these groups may be substituted independently of each other by alkyl, halogen, hydroxy, nitro, and optionally-CH in these groups2-may be substituted by-O-; or R5And R5' may be linked to each other or form a five-or six-membered ring through-O-, -S-, -NH-;
R6represents unsubstituted or substituted by one or more C1-C20Alkyl, halogen, cyano, SR7、OR8Substituted phenyl;
R7and R8Independently of one another, represents hydrogen, C1-C20Linear or branched alkyl. The UV photocuring composition containing the fluorenylaminoketone photoinitiator has high sensitivity, no residue after development, good pattern integrity, no odor or low odor of a cured coating, and excellent yellowing resistance.
The UV light curing composition is simple in preparation process, and according to a typical embodiment of the invention, the components are stirred and mixed uniformly in a dark room or a yellow lamp environment.
According to a typical embodiment of the present invention, the UV photocurable composition further comprises other photoinitiators, preferably, the other photoinitiators are selected from one or more of the group consisting of benzophenone, benzildimethyl ketal, 2-hydroxy-2-methyl-1-phenyl-propanone, 1-hydroxy-cyclohexyl-phenyl-ketone, isopropylthioxanthene, (2,4, 6-trimethyl-benzoyl) diphenylphosphine oxide and bis (2,4, 6-trimethylbenzoyl) -phenylphosphine oxide.
According to a typical embodiment of the present invention, the UV light curable composition further includes a colorant, which is an inorganic pigment or an organic pigment, and the colorant is used in an amount of 0 to 50 parts by mass, and preferably, the colorant is used in an amount of 0 to 20 parts by mass.
According to a typical embodiment of the present invention, the UV light-curable composition further comprises additives including one or more of surfactants, wetting agents, dispersants, rheology modifiers, defoamers, or storage enhancers.
The components of the UV light-curable composition of the present invention will be described in more detail below.
1) Dilute unsaturated photopolymerizable compounds
Dilute unsaturated photopolymerizable compounds: the compound having a radically polymerizable rare metal unsaturated bond may be a monomer compound (low molecular weight) or an oligomer (higher molecular weight).
Compounds containing one carbon-carbon double bond, preferably acrylate compounds, methacrylate compounds, for example: acrylate or methacrylate esters of monohydric alcohols: methyl acrylate, butyl acrylate, 2-ethylhexyl acrylate, cyclohexyl acrylate, isobornyl acrylate, hydroxyethyl acrylate, methyl methacrylate, and acrylonitrile, N-dialkylacrylamide, N-vinylpyrrolidone, vinylbenzene, vinyl acetate, vinyl ether.
A compound containing two or more carbon-carbon double bonds, comprising: alkyl diols, acrylates or methacrylates of polyols or polyester polyols, polyether polyols, epoxy polyols, acrylates of polyurethane polyols, vinyl ethers and unsaturated polyesters of unsaturated dicarboxylic acid polyols, for example polyethylene glycol diacrylate, neopentyl glycol diacrylate, trimethylolpropane triacrylate, polyethoxylated trimethylolpropane triacrylate, pentaerythritol tetraacrylate, dipentaerythritol hexaacrylate, polyester oligomer acrylates, polyurethane oligomer acrylates, aromatic epoxy acrylates, ethylene glycol maleate polyesters.
When the UV photocurable composition is used as a UV resist ink or a UV resist ink, at least one compound of the used thinly unsaturated photopolymerizable compounds contains an alkali soluble group, and such a compound is required to be capable of being initiated a crosslinking polymerization and to be soluble to a developer (a commonly used alkali developer) used in a developing treatment process at the time of forming an image pattern, and is preferably a carboxyl group-containing resin. In particular, a (meth) acrylate polymer obtained by copolymerizing a (meth) acrylate, an ethylenically unsaturated carboxylic acid, and another copolymerizable monomer. The (meth) acrylic acid ester may be methyl (meth) acrylate, ethyl (meth) acrylate, butyl (meth) acrylate, cyclohexyl (meth) acrylate, benzyl (meth) acrylate, diethylaminoethyl (meth) acrylate, dimethylaminoethyl (meth) acrylate, hydroxyethyl (meth) acrylate, hydroxypropyl (meth) acrylate, furfuryl (meth) acrylate, or glycidyl (meth) acrylate, and these (meth) acrylic acid esters may be used alone or in combination of two or more kinds. The ethylenically unsaturated carboxylic acid is preferably acrylic acid, methacrylic acid, vinylbenzoic acid, maleic acid, alkyl maleate, fumaric acid, itaconic acid, crotonic acid, cinnamic acid, acrylic acid dimer, an addition product of a monomer having a hydroxyl group (e.g., 2-hydroxyethyl (meth) acrylate, etc.) and a cyclic acid anhydride (e.g., maleic anhydride or phthalic anhydride, cyclohexane dicarboxylic anhydride), omega-carboxy-polycaprolactone- (meth) acrylate, or the like. Among them, (meth) acrylic acid is particularly preferable from the viewpoint of copolymerizability, cost, solubility, and the like. These ethylenically unsaturated carboxylic acids may be used alone or in combination of two or more. The other copolymerizable monomer is preferably (meth) acrylamide, n-butyl (meth) acrylate, styrene, vinylnaphthalene, (meth) acrylonitrile, vinyl acetate, or vinylcyclohexane, and these monomers may be used alone or in combination of two or more.
These carbon-carbon double bond compounds may be used alone, or two or more of them may be mixed and used, or a mixture may be subjected to a pre-copolymerization to form an oligomer for use in preparing a composition. The radical polymerizable resin is present in the photocurable composition in an amount of 5 to 95 parts by mass, preferably about 10 to 90 parts by mass.
2) Photoinitiator with structure shown as general formula (I)
The photoinitiator used in the photocurable composition of the present invention at least comprises a compound having a fluorene compound represented by general formula (I) as a main structure or one of its derivative compounds:
wherein,
a represents hydrogen, halogen, nitro, C1-C20Straight or branched alkyl of (2), C3-C10Alkylcycloalkyl of (A), C4-C10An alkylcycloalkyl or cycloalkylalkyl group of,
-COR6or-CO-CR2R3R4Group, wherein, optionally, -CH2-by O, N, S or C (═ O);
R1represents hydrogen, halogen, C1-C20Straight or branched alkyl of (2), C4-C20Cycloalkylalkyl or C2-C20Alkenyl of (2), optionally, R1In (C-CH)2-substituted by O, N, S or C (═ O), R1Can form a ring;
R2and R3Each independently represents C1-C20Straight or branched alkyl of (2), C3-C20Cycloalkyl of, C4-C20Cycloalkylalkyl of (C)4-C20Alkylcycloalkyl of (A), C6-C20Aryl radical, C6-C20Wherein one or more hydrogens in these groups may be substituted independently of each other by alkyl, halogen, hydroxy, nitro, and optionally, R2And R3In (C-CH)2-is substituted by O, N, S or C (═ O), and R2And R3Can mutually formA ring;
R4represents N-morpholinyl, N-piperidinyl, N-pyrrolyl or N-dialkyl, wherein one or more of the hydrogen atoms of these radicals may be substituted by halogen, hydroxy;
R5、R5' represents independently of one another C1-C20Linear or branched alkyl of (2), C4-C20Cycloalkyl of, C2-C20Alkenyl of (C)6-C20Aryl of (C)6-C20Wherein one or more hydrogens in these groups may be substituted independently of each other by alkyl, halogen, hydroxy, nitro, and optionally-CH in these groups2-may be substituted by-O-; or R5And R5' may be linked to each other or form a five-or six-membered ring through-O-, -S-, -NH-;
R6represents unsubstituted or substituted by one or more C1-C20Alkyl, halogen, cyano, SR7、OR8Substituted phenyl;
R7and R8Independently of one another, represents hydrogen, C1-C20Linear or branched alkyl.
Preferably, the fluorenylaminoketones represented by formula (I) include compounds represented by the following structures:
the derivative compound having the compound represented by the formula (I) as a main structure is a derivative obtained by substitution of branches or linkage of the compounds with each other while maintaining the main structure of the compound represented by the formula (I). When the derivative compound is used as a photoinitiator in the invention, the derivative compound with the main structure of the compound shown in the formula (I) is a compound shown in the following formulas (II) and (III):
the dimers of formula (II) and (III) are of formula (I), M represents a linking group formed by dimerization, which may be a bond, C1-C10Linear or branched alkylene of (C)6-C12Arylene or heteroarylene of (A), of-CH in M2-optionally substituted by sulfur, oxygen, NH or carbonyl, the hydrogen atom being optionally substituted by OH or NO2And (4) substituting.
Illustratively, the derivative compound may be a compound of the following structure:
in certain cases, it is advantageous to use mixtures of two or more of the above-mentioned initiators.
Of course, the photoinitiators having the formula (I) can also be used in a mixture with other known photoinitiators.
3) Other photoinitiators
For example: camphorquinone, Benzophenone (BP), benzophenone derivatives, such as 2,4, 6-trimethylbenzophenone, 2-methylbenzophenone, 3-methylbenzophenone, 4-methylbenzophenone, 2-methylcarbonylbenzophenone, 4 '-bis (chloromethyl) benzophenone, 4-chlorobenzophenone, 4-phenylbenzophenone, 3' -dimethyl-4-methoxy-benzophenone, [4- (4-methylphenylsulfanyl) phenyl ] -benzophenone, methyl 2-benzoylbenzoate, 3-methyl-4 '-phenylbenzophenone, 2,4, 6-trimethyl-4' -phenylbenzophenone, 4 '-bis (dimethylamino) benzophenone, benzophenone derivatives such as 2,4, 6-trimethylbenzophenone, 2-methylbenzophenone, 3-methylbenzophenone, 4' -dimethylbenzophenone, 4-methylbenzophenone, benzophenone derivatives such as methyl-4-methyl-4, 4 '-trimethylbenzophenone, 2-methylbenzophenone, 4' -methyl-4 '-methyl-benzophenone, 4' -methyl-4 '-methyl-4' -benzophenone, and mixtures thereof, 4, 4' -bis (diethylamino) benzophenone, ketal compounds such as benzildimethylketal (651); acetophenone, acetophenone derivatives, such as α -hydroxycycloalkylphenones, such as 2-hydroxy-2-methyl-1-phenyl-acetone (1173), 1-hydroxy-cyclohexyl-phenyl-ketone (184); 1- [4- (2-hydroxyethoxy) -phenyl ] -2-hydroxy-2-methyl-1-propan-1-one (2959); 2-hydroxy-1- {4- [4- (2-hydroxy-2-methyl-propionyl) -benzyl ] -phenyl } -2-methyl-propan-1-one (127); 2-hydroxy-1- {4- [4- (2-hydroxy-2-methyl-propionyl) -phenoxy ] -yl } -2-methyl-propan-1-one; dialkoxyacetophenones, α -hydroxy-or α -aminoacetophenones, for example (4-methylthiobenzoyl) -1-methyl-1-morpholinoethane (907), (4-morpholinobenzoyl) -1-benzyl-1-dimethylaminopropane (369), (4-morpholinobenzoyl) -1- (4-methylbenzyl) -1-dimethylaminopropane (379), (4- (2-hydroxyethyl) aminobenzoyl) -1-benzyl-1-dimethylaminopropane), 2-benzyl-2-dimethylamino-1- (3, 4-dimethoxyphenyl) -1-butanone; thioxanthone and derivatives thereof, such as Isopropylthioxanthone (ITX), 2-Chlorothioxanthone (CTX), 1-chloro-4-propoxythioxanthone (CPTX), 2, 4-Diethylthioxanthone (DETX); benzoin alkyl ethers and benzil ketals, phenylglyoxylates and derivatives thereof, such as oxo-phenyl-acetic acid 2- (2-hydroxy-ethoxy) -ethyl ester, dimeric phenylglyoxylates, such as oxo-phenyl-acetic acid 1-methyl-2- [2- (2-oxo-phenylacetyloxy) -propoxy ] -ethyl ester (754); other oxime esters, such as 1, 2-octanedione-1- [4- (phenylthio) phenyl ] -2- (4-benzoyloxime) (OXE01), ethanone 1- [ 9-ethyl-6- (2-methylbenzoyl) -9H-carbazol-3-yl ] -1- (4-acetyloxime) (OXE02), 9H-thioxanthene-2-carbaldehyde 9-oxo-2- (O-acetyloxime); monoacylphosphine oxides, such as (2,4, 6-trimethyl-benzoyl) diphenylphosphine oxide (TPO); bisacylphosphine oxides, such as bis- (2, 6-dimethoxy-benzoyl) - (2,4, 4-trimethyl-pentyl) phosphine oxide, bis (2,4, 6-trimethylbenzoyl) -phenylphosphine oxide (819), bis (2,4, 6-trimethylbenzoyl) -2, 4-dipentyloxyphenyl-phosphine oxide; hexaarylbisimidazole/coinitiator systems, such as o-chlorohexaphenyl-bisimidazole in combination with 2-mercaptobenzothiazole, and the like.
It is of interest that photoinitiators having a structure according to formula (I) are particularly suitable for use in combination with one or more of BP, 651, 1173, 184, ITX, TPO and 819, in addition to compounds of formula (I), formula (II) and formula (III). The photoinitiator, i.e., the photoinitiator having a structure represented by the general formula (I) and the other photoinitiator, is used in the photocurable composition in an amount of 0.05 to 15 parts by mass, preferably 1 to 10 parts by mass.
4) Sensitizer
The photocurable composition of the present invention may further contain a sensitizer for higher sensitivity or for matching with an LED light source.
The sensitizer may be pyrazoline compound, acridine compound, anthracene compound, coumarin compound, tertiary amine compound, etc. Specifically, there may be exemplified: 1-phenyl-3- (4-tert-butylstyryl) -5- (4-tert-butylphenyl) pyrazoline, 1-phenyl-3-biphenyl-5- (4-tert-butylphenyl) pyrazoline; 9-phenylacridine, 9-p-methylphenylacridine, 9-m-methylphenylacridine, 9-o-chlorophenylacridine; 2-ethylanthracene-9, 10-bis (methyl 4-chlorobutyrate), 1,2, 3-trimethylanthracene-9, 10-dioctylester, 2-ethylanthracene-9, 10-diethylester, 2-ethylanthracene-9, 10-bis (3-cyclohexylpropionate); 3,3 '-carbonylbis (7-diethylaminocoumarin), 3-benzoyl-7-diethylaminocoumarin, 3' -carbonylbis (7-methoxycoumarin), 7- (diethylamino) -4-methylcoumarin; n, N-bis- [4- (2-styryl-1-yl) -phenyl ] -N, N-bis (2-ethyl-6-methylphenyl) -1, 1-bisphenyl-4, 4-diamine, N-bis- [4- (2-styryl-1-yl) -4' -methylphenyl ] -N, N-bis (2-ethyl-6-methylphenyl) -1, 1-bisphenyl-4, 4-diamine, and the like.
The amount of the sensitizer used in the photocurable composition is 0 to 5 parts by mass, preferably 0 to 2 parts by mass.
5) Coloring agent
One or more pigments may be included in the UV light curable composition as a colorant. The pigment can be any color including, but not limited to, black, blue, brown, cyan, green, white, violet, magenta, red, orange, and yellow, as well as spot colors of mixtures thereof. The pigment may be an inorganic pigment or an organic pigment.
The organic pigment present in the UV photocurable composition may be perylene, phthalocyanine fuel (e.g. phthalocyanine green, phthalocyanine blue), cyanine pigment (Cy3, Cy5 and Cy7), naphthalocyanine pigment, nitroso pigment, azo pigment, diazo condensation pigment, basic dye pigment, basic blue pigment, indigo pigment, phloxine pigment, quinacridone pigment, isoindolinone pigment, dioxazine pigment, carbazole dioxazine violet pigment, alizarin lake pigment, phthalic amide pigment, carmine lake pigment, tetrachloroisoindolinone pigment, perinone pigment, anthraquinone pigment and quinophthalone pigment, and a mixture of two or more of the above or a derivative thereof.
Inorganic pigments in the photocurable composition include, for example, metal oxides (e.g., titanium dioxide, conductive titanium dioxide), iron oxides (e.g., red iron oxide, yellow iron oxide, black iron oxide, and transparent iron oxide), aluminum oxides, silicon oxides, carbon black pigments, metal sulfides, metal chlorides, and mixtures of two or more thereof.
The amount of the colorant used in the photocurable composition is 0 to 50 parts by mass, preferably 0 to 20 parts by mass.
6) Additive agent
Other components or additives may optionally be present in the photocurable composition to improve the properties and performance of the coating or ink, depending on the requirements of different applications. Additives include, but are not limited to, one or more of surfactants, wetting agents, dispersants, rheology modifiers, defoamers, or storage enhancers.
The amount of the additive to be used in the photocurable composition is 0 to 5 parts by mass, preferably 0 to 3 parts by mass.
The photocurable composition of the present invention can be polymerized by applying energy generated by an electron beam or the like such as ultraviolet light, visible light, near infrared light, or the like during polymerization reaction, thereby obtaining a desired polymer. As the energy-imparting light source, a light source having a dominant wavelength that emits light in a wavelength region of 250nm to 450nm is preferable. Examples of the light source having a dominant wavelength that emits light in a wavelength region of 250 to 450nm include various light sources such as an ultra-high pressure mercury lamp, a medium pressure mercury lamp, a mercury xenon lamp, a metal halide lamp, a high power metal halide lamp, a xenon lamp, a pulse light-emitting xenon lamp, a deuterium lamp, a Led lamp, a fluorescent lamp, an Nd-YAG3 double wave laser, a He-Cd laser, a nitrogen laser, a Xe-Cl excimer laser, a Xe-F excimer laser, and a semiconductor excited solid state laser.
The following examples are provided to further illustrate the application of the UV curable composition containing fluorenylaminoketone photoinitiator, and the evaluation methods and criteria are as follows:
firstly, the developability is observed by a Scanning Electron Microscope (SEM) on a pattern on a substrate, no residue is observed in an unexposed part (O), a small amount of residue is observed in the unexposed part, but the residual quantity is acceptable (excellent), a remarkable residue is observed in the unexposed part (●), and the integrity of the pattern has no defect according to the observed pattern, no defect (delta), a small part of defect (□) and serious defect (tangle-solidup);
secondly, evaluating the residual odor of the cured film by smelling the cured film through a nose, and grading the test results into three grades of 1 (no odor), 2 (odor) and 3 (pungent odor);
performing full transmission scanning on the yellowing property by using a Color difference instrument (American Alice X-Rite Color i7), wherein the scanning wavelength is 400-700nm, the yellowing property is evaluated by reading a value delta b, the smaller the delta b is, the more the yellowing is less obvious, and otherwise, the more the yellowing is serious;
and fourthly, evaluating the adhesive force by a grid-marking experimental method according to GB9286-88 grid-marking test of paint films of colored paint and varnish. The grade is 0-5 (6 grades in total) according to the damage degree, wherein the grade is 0, and no small lattice falls off from the film surface; grade 5 was very poor and severe flaking occurred on the membrane surface.
In the following discussion, UV light-curable compositions are formulated with the components being metered in weight percent, and Irgacure 907 and APi-307 being used as reference compounds under equivalent conditions.
Wherein 907 and 307 are represented by the following structural formulas:
the first embodiment is as follows: UV coating
Coating conditions: preprocessing a base material tinplate paster according to GB/T9271-2008 color paint and varnish standard test plate, coating a formula which is uniformly stirred in a dark room on the tinplate paster by a 25# wire rod, wherein the coating thickness is about 25 mu m, and exposing conditions are as follows: RW-UV 70201 crawler-type exposure machine, radiation wavelength of 250-450nm, aging conditions: after exposure, the film was placed in an oven at 80 ℃ and baked for 24 hours, and the test results are shown in the following table 1:
TABLE 1
Example two: UV resist ink
Printing conditions: 100T silk screen, 8-10 μm of dry film thickness, baking condition: baking at 75 ℃ for 20 minutes, and exposing under the following conditions: RW-UV 70201 crawler-type exposure machine, radiation wavelength of 250-450nm, developing conditions: 1% sodium carbonate solution, developed at 30. + -. 2 ℃ for 40s, and the test results are shown in Table 2 below:
TABLE 2
Example three: UV solder resist ink
A. The component B is evenly mixed according to the ratio of 3:1 and is placed for half an hour. Printing conditions: 36-43T silk screen printing, the thickness of a dry film is 12-15 mu m, and the pre-baking condition is as follows: the first side at 75 ℃ for 20 minutes and the second side for 25 minutes; exposure conditions: RW-UV 70201 crawler-type exposure machine with radiation wavelength of 250-450 nm; developing conditions: 0.5% NaOH solution, 30. + -. 2 ℃ for 60s, the results of the test are shown in Table 3 below:
TABLE 3
Example four: UV flexo printing ink
The raw materials are uniformly mixed in a dark room, coated on a white paperboard with the thickness of 5 mu m, and exposed under the following conditions: RW-UV 70201 crawler exposure machine, radiation wavelength of 250-450nm, test results are shown in Table 4 below:
TABLE 4
Example five: UV offset printing ink
The raw materials are uniformly mixed in a dark room, coated on a plastic substrate with the thickness of 2 mu m, and exposed under the following conditions: RW-UV 70201 crawler exposure machine, radiation wavelength of 250-450nm, and test results shown in Table 5 below:
TABLE 5
As can be seen from the experimental results of examples 1-5, the photocuring composition containing the fluorenylaminoketone photoinitiator has the advantages of good photocuring performance, good yellowing resistance, no odor residue after curing and excellent comprehensive performance when being applied to photocuring coatings and inks.
The above description is only a preferred embodiment of the present invention and is not intended to limit the present invention, and various modifications and changes may be made by those skilled in the art. Any modification, equivalent replacement, or improvement made within the spirit and principle of the present invention should be included in the protection scope of the present invention.
Claims (30)
1. A UV light-curable composition containing a fluorenylaminoketone photoinitiator, comprising: a dilute unsaturated photopolymerizable compound and a photoinitiator; wherein the photoinitiator comprises a compound with a structure shown as a general formula (I) or a derivative compound thereof,
wherein,
a represents hydrogen, halogen, nitro, C1-C20Straight or branched alkyl of (2), C3-C10Alkylcycloalkyl of (C)4-C10Cycloalkylalkyl, cycloalkyl,
-COR6or-CO-CR2R3R4Group, wherein, optionally, -CH2-by O, N, S or C (═ O);
R1represents hydrogen, halogen, C1-C20Straight or branched alkyl of (2), C4-C20Cycloalkylalkyl or C2-C20Alkenyl of (2), optionally, R1In (C-CH)2-substituted by O, N, S or C (═ O), R1Can form a ring;
R2and R3Each independently represents C1-C20Straight or branched alkyl of (2), C3-C20Cycloalkyl of, C4-C20Cycloalkylalkyl of (C)4-C20And optionally, R2And R3In (C-CH)2-is substituted by O, N, S or C (═ O), and R2And R3Can form a ring with each other;
R4represents N-morpholinyl, N-piperidinyl or N-pyrrolyl;
R5、R5' represents independently of one another C1-C20Linear or branched alkyl of (2), C4-C20Cycloalkyl of, C2-C20And optionally-CH in these groups2-may be substituted by-O-; or R5And R5' may be linked to each other or form a five-or six-membered ring through-O-, -S-, -NH-;
R6represents unsubstituted or substituted by one or more C1-C20Alkyl, halogen, cyano, SR7、OR8Substituted phenyl;
R7and R8Independently of one another, represents hydrogen, C1-C20Linear or branched alkyl of (a);
the derivative compound has a compound represented by general formula (II) or (III):
wherein M represents a linking group formed by dimerization, which may be a bond, C1-C10Linear or branched alkylene of (C)6-C12Optionally, -CH in M2By sulfur, oxygen, NH, or carbonyl groups, optionally hydrogen atoms by OH or NO2And (4) substituting.
2. The UV curable composition according to claim 1, wherein said ethylenically unsaturated photopolymerizable compound is used in an amount of 5 to 95 parts by mass, and said photoinitiator is used in an amount of 0.05 to 15 parts by mass.
3. The UV curable composition according to claim 2, wherein the ethylenically unsaturated photopolymerizable compound is used in an amount of 10 to 90 parts by mass, and the photoinitiator is used in an amount of 1 to 10 parts by mass.
4. The UV-curable composition according to claim 1, wherein the photoinitiator having the structure of formula (I) is selected from the group consisting of
5. The UV-curable composition according to claim 1, wherein the derivative compound is
6. The UV curable composition according to claim 1, wherein the photoinitiator having a structure represented by formula (I) or a derivative compound thereof is a mixture of two or more compounds.
7. The UV light-curable composition according to claim 1, wherein the ethylenically unsaturated photopolymerizable compound is a monomeric compound or an oligomeric compound.
8. The UV-curable composition according to claim 1, wherein the ethylenically unsaturated photopolymerizable compound is a compound containing one carbon-carbon double bond.
9. The UV curable composition of claim 8, wherein the ethylenically unsaturated photopolymerizable compound is an acrylate compound or a methacrylate compound.
10. The UV light-curable composition according to claim 1, wherein the ethylenically unsaturated photopolymerizable compound is a compound containing two or more carbon-carbon double bonds.
11. The UV light-curable composition according to claim 10, wherein the ethylenically unsaturated photopolymerizable compound is an acrylate ester of an alkyl polyol or a methacrylate ester of an alkyl polyol or an unsaturated polyester of a polyester polyol, a polyether polyol, an epoxy polyol, an acrylate ester of a polyurethane polyol, a vinyl ether, and an unsaturated dicarboxylic acid polyol.
12. The UV curable composition according to claim 1, wherein at least one compound of the dilute unsaturated photopolymerizable compounds used contains an alkali soluble group when the UV curable composition is used as a UV resist ink or a UV solder resist ink.
13. The UV photocurable composition according to claim 12, wherein the ethylenically unsaturated photopolymerizable compound is a carboxyl group-containing resin, (meth) acrylate, ethylenically unsaturated carboxylic acid, or (meth) acrylate-based polymer.
14. The UV photocurable composition according to claim 13, wherein the (meth) acrylate is selected from one or more of the group consisting of methyl (meth) acrylate, ethyl (meth) acrylate, butyl (meth) acrylate, cyclohexyl (meth) acrylate, benzyl (meth) acrylate, diethylaminoethyl (meth) acrylate, ω -carboxy-polycaprolactone- (meth) acrylate, hydroxyethyl (meth) acrylate, hydroxypropyl (meth) acrylate, furfuryl (meth) acrylate, glycidyl (meth) acrylate.
15. The UV curable composition according to claim 13, wherein the ethylenically unsaturated carboxylic acid is one or more selected from the group consisting of acrylic acid, methacrylic acid, vinylbenzoic acid, maleic acid, fumaric acid, itaconic acid, crotonic acid, cinnamic acid and acrylic acid dimer.
16. The UV curable composition according to claim 15, wherein the ethylenically unsaturated carboxylic acid is (meth) acrylic acid.
17. The UV photocurable composition according to claim 13 wherein the ethylenically unsaturated photopolymerizable compound is selected from one or more of the group consisting of alkyl maleates, (meth) acrylamides, n-butyl (meth) acrylate, styrene, vinyl naphthalene, (meth) acrylonitrile, vinyl acetate, vinyl cyclohexane.
18. The UV curable composition according to claim 1, further comprising an additional photoinitiator.
19. The UV photocurable composition according to claim 18 wherein the additional photoinitiator is selected from one or more of the group consisting of benzophenone, benzildimethyl ketal, 2-hydroxy-2-methyl-1-phenyl-acetone, 1-hydroxy-cyclohexyl-phenyl-ketone, isopropylthioxanthene, (2,4, 6-trimethyl-benzoyl) diphenylphosphine oxide and bis (2,4, 6-trimethylbenzoyl) -phenylphosphine oxide.
20. The UV curable composition according to claim 1, further comprising a sensitizer.
21. The UV curable composition according to claim 20, wherein the sensitizer is a pyrazoline compound, an acridine compound, an anthracene compound, a coumarin compound, or a tertiary amine compound.
22. The UV curable composition according to claim 21, wherein the sensitizer is used in an amount of 0 to 5 parts by mass.
23. The UV curable composition according to claim 22, wherein the sensitizer is used in an amount of 0 to 2 parts by mass.
24. The UV curable composition according to claim 1, further comprising a colorant, wherein the colorant is an inorganic pigment or an organic pigment, and the colorant is used in an amount of 0 to 50 parts by mass.
25. The UV light-curable composition according to claim 24, wherein the colorant is used in an amount of 0 to 20 parts by mass.
26. The UV light-curable composition according to claim 1, further comprising an additive comprising one or more of a surfactant, a wetting agent, a dispersant, a rheology modifier, a defoamer, or a storage enhancer.
27. The UV curable composition according to claim 26, wherein the additive is used in an amount of 0 to 5 parts by mass.
28. The UV curable composition according to claim 27, wherein the additive is used in an amount of 0 to 3 parts by mass.
29. Use of a UV light curable composition according to any one of claims 1 to 28 in UV coatings and UV inks.
30. Use according to claim 29, wherein the UV ink comprises UV resist ink, UV solder resist ink, flexo ink and offset ink.
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| CN110819224B (en) * | 2018-08-09 | 2021-06-25 | 江苏百赛飞生物科技有限公司 | Coating composition, protective coating based on coating composition and coated product |
| CN112010997B (en) * | 2019-05-30 | 2021-10-08 | 常州强力先端电子材料有限公司 | Fluorene photoinitiator, preparation method thereof, photocuring composition containing fluorene photoinitiator and application of fluorene photoinitiator in photocuring field |
| CN113004739B (en) * | 2019-12-20 | 2021-12-28 | 常州强力电子新材料股份有限公司 | Photo-curing composition, photo-curing ink containing photo-curing composition and application of photo-curing ink |
| WO2020238862A1 (en) * | 2019-05-30 | 2020-12-03 | 常州强力先端电子材料有限公司 | Fluorene initiator, photocurable composition comprising same, and application thereof |
| CN114442425A (en) * | 2020-10-30 | 2022-05-06 | 常州正洁智造科技有限公司 | Curable resin composition, solder resist film formed from the same, interlayer insulating material, and printed wiring board |
| CN114591241B (en) * | 2022-03-14 | 2024-02-13 | 内蒙古扬帆新材料有限公司 | Intramolecular sensitized macromolecular photoinitiator containing pyrazoline and alpha-amino ketone and preparation method and application thereof |
| CN115894399B (en) * | 2022-12-06 | 2024-05-28 | 天津久日新材料股份有限公司 | Fluorene derivative photoinitiator and preparation method and application thereof |
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