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WO1995016722A1 - Composition photodurcissable - Google Patents

Composition photodurcissable Download PDF

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Publication number
WO1995016722A1
WO1995016722A1 PCT/US1994/013638 US9413638W WO9516722A1 WO 1995016722 A1 WO1995016722 A1 WO 1995016722A1 US 9413638 W US9413638 W US 9413638W WO 9516722 A1 WO9516722 A1 WO 9516722A1
Authority
WO
WIPO (PCT)
Prior art keywords
photocurable composition
composition according
group
acrylate
meth
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/US1994/013638
Other languages
English (en)
Inventor
Fujio Hara
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
3M Co
Original Assignee
Minnesota Mining and Manufacturing Co
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority to US08/648,046 priority Critical patent/US5739174A/en
Application filed by Minnesota Mining and Manufacturing Co filed Critical Minnesota Mining and Manufacturing Co
Priority to EP95903615A priority patent/EP0734405A1/fr
Publication of WO1995016722A1 publication Critical patent/WO1995016722A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

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
    • 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
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/68—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the catalysts used
    • 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
    • G03F7/0045—Photosensitive materials with organic non-macromolecular light-sensitive compounds not otherwise provided for, e.g. dissolution inhibitors
    • 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
    • G03F7/029—Inorganic compounds; Onium compounds; Organic compounds having hetero atoms other than oxygen, nitrogen or sulfur
    • 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
    • G03F7/075—Silicon-containing compounds
    • G03F7/0755—Non-macromolecular compounds containing Si-O, Si-C or Si-N bonds

Definitions

  • the present invention relates to a photocurable composition, and in particular, to a photocurable composition preferably employed for a luster agent for coating an automobile body and the like, including, for example, a coated surface of an automobile, a plastic bumper, and a tire.
  • a wax such as carnuba wax, polyethylene wax, a silicone such as dimethyl polysiloxane, and a variety of modified silicones, and the like, have been employed as a luster agent for use on the exterior of an automobile.
  • these luster agents do not impart sufficient gloss, water repellency and stain resistance, and have poor durability.
  • Japanese Patent Kokai Publication No. S51-134794 disclose a visible light curable composition comprising an epoxy resin, an aryl halonium salt and an organic dye.
  • the epoxy resin disclosed in the reference may be obtained from a reaction of bisphenol A with epichlorohydrin.
  • the epoxy resin itself shows no gloss nor stain resistance, and it hardly be used as a luster agent.
  • a UV curable silicone releasing composition having epoxy and/or acrylic functionality which is disclosed in Japanese Patent Kokai Publication S58-213024, cannot be employed as a luster agent, since the resin is designed to function as a releasing agent.
  • a UV curable organopolysiloxane composition disclosed in Japanese Patent Kokai Publication H4-33960 comprises a organopolysiloxane having both acrylic and epoxy functionality, and a specific sulfonate photoinitiator. Even though the composition is photocured in the presence of air as a luster agent, oxygen contained in the air affects and makes the surface of the coating tacky, and the resulting coating lacks durability. Further, another problem is presented in that a UV (i.e., ultraviolet light) irradiation apparatus is needed for the composition.
  • the present invention overcomes the above described prior art problems while providing a specific photocurable composition which is curable by using a visible as well as UV light.
  • the photocurable composition shows remarkably good properties when it is employed as a luster agent.
  • the present invention relates to a photocurable composition
  • a photocurable composition comprising: (a) a photopolymerizable monomer or oligomer; (b) a photoinitiator; and (c) a photosensitizer, wherein the photosensitizer comprises at least one material selected from the group consisting of sulfolene, sulfolene derivatives, isatin, and isatin derivatives.
  • a photopolymerizable monomer or oligomer employed in the present invention includes a monomeric or oligomeric compound having any one or both of an epoxy group and a vinyl group.
  • Preferred photopolymerizable monomers or oligomers include organopolysiloxanes having an epoxy group or a vinyl group.
  • the organopolysiloxane may be prepared by hydrosilyl-addition of an epoxy compound to an organopolysiloxane having a n-SiH bond.
  • the organopolysiloxane may be prepared by hydrosilyl- addition of an ⁇ -haloolefin to an organopolysiloxane having a n-SiH bond, and then, replacing the halogen with an acrylate in the presence of a base, according to a procedure disclosed in Japanese Patent Kokai Publication No. S58-213024.
  • an organopolysiloxane having an epoxy group is preferred as the photopolymerizable compound, because it is not affected by oxygen.
  • suitable organopolysiloxanes having an epoxy group are those represented by the following general formulae I, II, and III.
  • the group R is a divalent linking group.
  • group R can be a substituted or unsubstituted alkylene group having 1 to 10 carbon atoms.
  • the R group is preferably aliphatic. Examples of such alkylene groups for group R include ethylene, ethylene, propylene and butylene, and so forth.
  • the compounds of formulae I, II and III can be used solely or in combinations thereof without' limitation.
  • the compounds of formulae I, II and III contemplated for the present invention preferably have a viscosity of 10°-10 5 cps at 25°C and an epoxy equivalent of 10 2 -10 4 .
  • An alicyclic epoxy-modified organopolysiloxane, such as represented by formulae I, II, and III, is very useful due to its high reactivity.
  • suitable compounds include an alkyl ( eth)acrylate such as methyl (meth)acrylate, ethyl (meth)acrylate, propyl (meth)acrylate, 2- ethylhexyl (meth)acrylate, n-butyl (meth)acrylate and the like; and another vinyl compound such as styrene, ⁇ -methyl styrene, N-methyl carbazole, isobutyl vinyl ether, vinyl acetate and vinyl pyrrolidone; and the like.
  • alkyl ( eth)acrylate such as methyl (meth)acrylate, ethyl (meth)acrylate, propyl (meth)acrylate, 2- ethylhexyl (meth)acrylate, n-butyl (meth)acrylate and the like
  • another vinyl compound such as styrene, ⁇ -methyl styrene, N-methyl carbazole, isobutyl vinyl ether
  • the photoinitiator employed in the present invention is not particularly limited as long as it is a photoinitiator which initiates a polymerization of the above-described epoxy group or vinyl group upon exposure to light.
  • a preferred photoinitiator employed in the present invention includes an onium salt, since a cation polymerization can be carried out by using the onium salt. In general, any onium salt conventionally used as a photoinitiator can be employed.
  • onium salt examples include triphenylsulfonium hexafluoroantimonate, bis(dodecylphenyl)iodoniu hexafluoroantimonate, diphenyliodonium hexafluorophosphate, di-4,4-dimethylphenyliodonium hexafluoroacetate and the like.
  • a particularly preferred onium salt employed in the present invention is triphenylsulfonium hexafluoroantimonate because of its high reactivity.
  • the photoinitiator of the present invention is employed in an amount 0.1 to 50 parts, preferably 0.5 to 10 parts, by weight, based on 100 parts by weight of the photopolymerizable monomer or oligomer. if an amount of the photoinitiator is less than 0.1 parts by weight, a durable luster coating may not be provided due to an insufficient initiation of polymerization. If an amount of the photoinitiator is more than 50 parts by weight, a film strength of the resulting cured coating may become poor.
  • a photosensitizer employed in the present invention is at least one material selected from the group consisting of sulfolene, sulfolene derivatives, isatin, and isatin derivatives.
  • Sulfolene is a compound of the general formula:
  • the sulfolene derivatives include a sulfonene compound having at least one of the hydrogen atoms substituted to provide a substituent bonded to the cyclic moiety of the sulfolene.
  • substituents include an alkyl group of 1-5 carbon atoms, an alkoxy group of 1-5 carbon atoms, halogen, cyano group, an amino group, a phenyl group, and the like.
  • Isatin is a compound of the general formula:
  • the isatin derivatives include an isatin compound having at least one of the hydrogen atoms substituted to provide a substituent bonded to the cyclic moiety of the isatin.
  • substituents include an alkyl group of 1-5 carbon atoms, an alkoxy group of 1-5 carbon atoms, halogen, a cyano group, an amino group, a phenyl group, and the like.
  • the photosensitizer of the present invention such as sulfolene and isatin and derivatives thereof may be employed alone or in combination with each other and/or in combination with additional photosensitizers, such as anthraquinone.
  • the photosensitizer of the present invention is employed in an amount 1 to 200, preferably 10 to 50 parts by weight based on 100 parts by weight of a photoinitiator. If an amount of the photosensitizer is less than 1 part by weight, a sensitizing function may become insufficient. If an amount of the photosensitizer is more than 200 parts by weight, latency of the photosensitizer may become poor, a breakage during storage may occur, and a cost of the composition way become high.
  • a composition of the present invention itself is a photocurable composition for use in a variety of applications, and exhibits superior curability to visible light irradiation.
  • a photocurable composition of the present invention may be formulated as an emulsion by using an emulsifier, however it is most preferable that a photocurable composition of the present invention is used as a luster agent for use in an automobile.
  • An emulsifier employed includes a negative ionic, positive ionic, nonionic and amphoteric emulsifiers such as a salt of fatty acid, an ester of fatty acid, and fluorine or silicone class emulsifier.
  • An * emulsifier of the present invention is employed in an amount of 1 to 100, preferably 5 to 50 parts by weight based on 100 parts by weight of a photopolymerizable monomer or oligomer.
  • An aqueous medium may be employed in combination with an emulsifier.
  • a water miscible organic solvent and/or water were generally used as an aqueous medium.
  • the aqueous medium include an alcohol such as methanol, ethanol, isopropyl alcohol, glycerol and ethylene glycol, an ether such as dimethyl ether, diethyl ether, methyl cellosolve and ethyl cellosolve, a ketone such as acetone, methyl ethyl ketone, methyl isobutyl ketone, and the like.
  • An amount of the aqueous medium employed is not limited, but may be used in an amount of 0.1 to 50 parts by weight based on 100 parts by weight of water.
  • a luster agent comprising a photocurable composition of the present invention exhibits remarkably good lustering ability, gloss, water repellency and stain resistance and durability, when it is applied in a thickness of 0.01 to 5 ⁇ m on an automobile body or exterior part as the substrate.
  • Solvent based photocurable compositions were prepared by blending components indicated in Table 1. The resulting compositions were coated on test-pieces in thickness of 1 ⁇ m by using a buff made of sponge. The test piece was a cold rolled steel panel on which an acrylic urethane paint (Nax BESTA available from Nippon Paint Co., Ltd.) was coated.
  • the resulting coatings were photocured by using a halogen lamp of 300 watts in power at a distance of 20 cm for Examples 1 and 2 and Comparative Examples 1 and 2, or with direct sunlight for Example 3 and 4 and Comparative Examples 3 and 4.
  • the time to cure for each sample was indicated in Table 1.
  • a stain resistance was then evaluated by the following procedure. A sample for evaluating stain resistance was aged outdoor for two weeks at first; the sample was then wiped with a clean cloth; and thereafter a residue of a mud stain was determined.
  • organopolysiloxane 1 was an alicyclic epoxy silicone having a viscosity of 8000 cps and an epoxy equivalent of 4000 available from Toray Dow Corning Silicone K.K. under the tradename "BY16-839”
  • organopolysiloxane 2 was an alicyclic epoxy silicone having a viscosity of 30 cps and an epoxy equivalent of 600-700 obtained from Shinetsu Chemical Co., Ltd. under the tradename "X-22-169AS”.
  • Table 1 Table 1
  • organopolysiloxane 1 100 100 - 50 100 100 100 100 100 organopolysiloxane 2 - - 100 50 - - - -
  • camphorquinone - - - - 1 - 0.5 - anthraquinone - - - - - 0.5 0.5 - acridine orange - - - - - - - 1

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  • Chemical & Material Sciences (AREA)
  • Physics & Mathematics (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • General Physics & Mathematics (AREA)
  • Paints Or Removers (AREA)
  • Epoxy Resins (AREA)

Abstract

Composition photodurcissable comprenant: (a) un monomère ou un oligomère photopolymérisable; (b) un photoinitiateur; et (c) un photosensibilisant qui est lui-même constitué d'au moins une matière sélectionnée dans le groupe formé par sulfolène, dérivés de sulfolène, isatine et dérivés d'isatine.
PCT/US1994/013638 1993-12-15 1994-11-28 Composition photodurcissable Ceased WO1995016722A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
US08/648,046 US5739174A (en) 1993-12-15 1994-11-21 Epoxysilicone photocurable composition comprising a sulfolene or isatin photosensitizer
EP95903615A EP0734405A1 (fr) 1993-12-15 1994-11-28 Composition photodurcissable

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP31473493A JPH07207188A (ja) 1993-12-15 1993-12-15 光硬化性組成物
JP5/314734 1993-12-15

Publications (1)

Publication Number Publication Date
WO1995016722A1 true WO1995016722A1 (fr) 1995-06-22

Family

ID=18056940

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US1994/013638 Ceased WO1995016722A1 (fr) 1993-12-15 1994-11-28 Composition photodurcissable

Country Status (4)

Country Link
EP (1) EP0734405A1 (fr)
JP (1) JPH07207188A (fr)
CA (1) CA2177700A1 (fr)
WO (1) WO1995016722A1 (fr)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR100557553B1 (ko) * 2001-06-29 2006-03-03 주식회사 하이닉스반도체 포토레지스트 단량체, 그의 중합체 및 이를 함유하는포토레지스트 조성물
US7989426B2 (en) 2002-02-15 2011-08-02 Johns Hopkins University School Of Medicine Selective induction of apoptosis to treat ocular disease by expression of PEDF
US20230183391A1 (en) * 2020-05-18 2023-06-15 Bowling Green State University Biomass derived diketones as efficient visible light photoinitiators

Citations (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3428590A (en) * 1965-01-22 1969-02-18 Yawata Chem Ind Co Ltd Process for the production of trioxane copolymers
US3756827A (en) * 1972-01-25 1973-09-04 Du Pont L compounds and selected sensitizerss photopolymerizable compositions containing cyclic cis-alpha-dicarbony
US3915824A (en) * 1973-03-30 1975-10-28 Scm Corp Uv and laser curing of the polymerizable binder
US4172157A (en) * 1978-09-19 1979-10-23 Celanese Corporation Aminoplast/alkyd coating composition
JPS58149042A (ja) * 1982-03-02 1983-09-05 Tokyo Ohka Kogyo Co Ltd ポジ型感光性組成物
EP0143315A1 (fr) * 1983-10-27 1985-06-05 General Electric Company Composition de polissage durable à base d'émulsion de silicone
US4600436A (en) * 1982-09-27 1986-07-15 General Electric Company Durable silicone emulsion polish
EP0330406A2 (fr) * 1988-02-22 1989-08-30 Japan Synthetic Rubber Co., Ltd. Composition de résine sensible au rayonnement
EP0501055A1 (fr) * 1988-06-20 1992-09-02 Armstrong World Industries, Inc. Composition de revêtement
EP0524524A1 (fr) * 1991-07-26 1993-01-27 Bayer Ag Procédé de revêtement d'articles en polycarbonate

Patent Citations (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3428590A (en) * 1965-01-22 1969-02-18 Yawata Chem Ind Co Ltd Process for the production of trioxane copolymers
US3756827A (en) * 1972-01-25 1973-09-04 Du Pont L compounds and selected sensitizerss photopolymerizable compositions containing cyclic cis-alpha-dicarbony
US3915824A (en) * 1973-03-30 1975-10-28 Scm Corp Uv and laser curing of the polymerizable binder
US4172157A (en) * 1978-09-19 1979-10-23 Celanese Corporation Aminoplast/alkyd coating composition
JPS58149042A (ja) * 1982-03-02 1983-09-05 Tokyo Ohka Kogyo Co Ltd ポジ型感光性組成物
US4600436A (en) * 1982-09-27 1986-07-15 General Electric Company Durable silicone emulsion polish
EP0143315A1 (fr) * 1983-10-27 1985-06-05 General Electric Company Composition de polissage durable à base d'émulsion de silicone
EP0330406A2 (fr) * 1988-02-22 1989-08-30 Japan Synthetic Rubber Co., Ltd. Composition de résine sensible au rayonnement
EP0501055A1 (fr) * 1988-06-20 1992-09-02 Armstrong World Industries, Inc. Composition de revêtement
EP0524524A1 (fr) * 1991-07-26 1993-01-27 Bayer Ag Procédé de revêtement d'articles en polycarbonate

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
CHEMICAL ABSTRACTS, vol. 119, no. 10, 6 September 1993, Columbus, Ohio, US; abstract no. 96239, "Polymerization of methyl methacrylate using isatin and benzoyl peroxide combination as photoinitiator" *
PATENT ABSTRACTS OF JAPAN vol. 7, no. 270 (P - 240) 2 December 1983 (1983-12-02) *
SOM PRAB KUMAR, EUR. POLYM. J., no. 29, 1993, pages 889 - 892 *

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR100557553B1 (ko) * 2001-06-29 2006-03-03 주식회사 하이닉스반도체 포토레지스트 단량체, 그의 중합체 및 이를 함유하는포토레지스트 조성물
US7989426B2 (en) 2002-02-15 2011-08-02 Johns Hopkins University School Of Medicine Selective induction of apoptosis to treat ocular disease by expression of PEDF
US20230183391A1 (en) * 2020-05-18 2023-06-15 Bowling Green State University Biomass derived diketones as efficient visible light photoinitiators
EP4153171A4 (fr) * 2020-05-18 2024-06-26 Bowling Green State University Dicétones dérivées de biomasse utilisées en tant que photo-initiateurs de lumière visible efficaces

Also Published As

Publication number Publication date
CA2177700A1 (fr) 1995-06-22
JPH07207188A (ja) 1995-08-08
EP0734405A1 (fr) 1996-10-02

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