WO2018199450A1 - Composition photo-durcissable pour revêtement et film de revêtement - Google Patents

Composition photo-durcissable pour revêtement et film de revêtement Download PDF

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Publication number
WO2018199450A1
WO2018199450A1 PCT/KR2018/002113 KR2018002113W WO2018199450A1 WO 2018199450 A1 WO2018199450 A1 WO 2018199450A1 KR 2018002113 W KR2018002113 W KR 2018002113W WO 2018199450 A1 WO2018199450 A1 WO 2018199450A1
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formula
compound
weight
coating composition
photocurable coating
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PCT/KR2018/002113
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English (en)
Korean (ko)
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김훈래
이지영
강하나
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(주) 개마텍
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Publication of WO2018199450A1 publication Critical patent/WO2018199450A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D183/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Coating compositions based on derivatives of such polymers
    • C09D183/04—Polysiloxanes
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • 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

Definitions

  • the present invention relates to a photocurable coating composition and a coating film
  • the photocurable coating composition may have a high transparency and at the same time can form a coating film excellent in flexibility, surface hardness and adhesion.
  • each layer, substrate material, and various electrode materials constituting the display especially AMOLED, must have durability in repeated bending, and especially the outermost cover material has high surface hardness. And flexibility at the same time.
  • the photopolymer which reacts by the mechanism which produces a polymerization difference according to the intensity of light is usually comprised from an acryl-type monomer, an epoxy-type monomer, an oligomer, an initiator, and a polymer binder.
  • a film made of an acrylic monomer has a high applicability, but has a serious problem of shrinkage after curing by light or heat, and a film made of an epoxy monomer has a problem of low shrinkage but low reactivity. Therefore, in order to improve this, it is necessary to develop a novel photopolymerizable monomer having high reactivity during curing and high polymerization efficiency and low shrinkage rate.
  • the present inventors have completed the present invention by developing a photocurable coating composition comprising a compound having a spiro structure and a compound having a siloxane structure capable of adjusting the curing shrinkage rate.
  • An object of the present invention is to provide a photocurable coating composition having high transparency and excellent flexibility, surface hardness and adhesion.
  • Another object of the present invention is to provide a coating film prepared from the photocurable coating composition.
  • the present invention is at least one spiro compound selected from the group consisting of Formula 1 to 5; And at least one siloxane compound selected from the group consisting of the following Chemical Formulas 6 to 8, a photocurable coating composition is provided.
  • X is oxygen or -CHR 1- ,
  • n 2 or 3
  • n 1 or 2
  • l is an integer from 1 to 20
  • R 1 to R 13 are each independently hydrogen, C 1-4 alkyl, C 2-5 alkenyl, C 1-4 alkyl substituted or unsubstituted acrylate, C 6-14 aryl, epoxy, Glycidyl, C 3-8 cycloalkyl, C 4-8 epoxycycloalkyl, alcohol substituted or unsubstituted with epoxy group, or C 1-10 alkoxy C 1- substituted or substituted with halogen or phenyl 4 is alkyl,
  • R 14 are each independently substituted or unsubstituted C 1-5 alkoxy C 1-4 alkyl, C 4-8 epoxycycloalkyl substituted C 1-4 alkyl, (meth) acrylate C 1-4 alkyl or C 2-5 alkenyl.
  • the present invention provides a coating film prepared using the photocurable coating composition.
  • the photocurable coating composition of the present invention may include a spiro compound and a siloxane compound to prepare a coating film having excellent surface hardness and flexibility through UV curing.
  • the coating film formed from the composition of the present invention has a high transparency and excellent surface hardness, adhesion, flexibility, etc. can effectively prevent cracks or interfacial film removal due to shrinkage during curing, and thus flexible display, liquid crystal display device It can be applied to various fields using photocuring systems such as OLED displays, molded products, coatings, dental materials, and the like.
  • the photocurable coating composition of the present invention is at least one spiro compound selected from the group consisting of Formula 1 to 5; And at least one siloxane compound selected from the group consisting of:
  • X is oxygen or -CHR 1- ,
  • n 2 or 3
  • n 1 or 2
  • l is an integer from 1 to 20
  • R 1 to R 13 are each independently hydrogen, C 1-4 alkyl, C 2-5 alkenyl, C 1-4 alkyl substituted or unsubstituted acrylate, C 6-14 aryl, epoxy, Glycidyl, C 3-8 cycloalkyl, C 4-8 epoxycycloalkyl, alcohol substituted or unsubstituted with epoxy group, or C 1-10 alkoxy C 1- substituted or substituted with halogen or phenyl 4 is alkyl,
  • R 14 are each independently substituted or unsubstituted C 1-5 alkoxy C 1-4 alkyl, C 4-8 epoxycycloalkyl substituted C 1-4 alkyl, (meth) acrylate C 1-4 alkyl or C 2-5 alkenyl.
  • the spiro compound is at least one selected from the group consisting of Chemical Formulas 1 to 5.
  • X is oxygen or —CHR 1 —
  • n is 2 or 3
  • m is 1 or 2
  • R 1 to R 13 are each independently hydrogen, alkyl of C 1-4 , C 2-5 al Kenyl, acrylate substituted or unsubstituted with C 1-4 alkyl, C 6-14 aryl, epoxy, glycidyl, C 3-8 cycloalkyl, C 4-8 epoxycycloalkyl, epoxy group substituted Or unsubstituted alcohol or alkyl of C 1-10 alkoxy C 1-4 unsubstituted or substituted with halogen or phenyl.
  • the spiro compound has the structure of Formula 4 or 5, X is oxygen, m is 1, and R 9 to R 13 are each independently hydrogen, methyl, phenyl, naphthyl, epoxy Glycidyl, acrylate, methacrylate, or Can be. More specifically, the spiro compound may be at least one selected from the group consisting of Formulas 9 to 14:
  • the spiro compound has the structure of Formula 1, X is oxygen or -CH 2- , n is 3, and R 2 and R 3 are each independently hydrogen, methyl, propoxymethyl, Phenylepoxymethyl or Can be.
  • the spiro compound may be at least one selected from the group consisting of Formulas 15 to 18:
  • the spiro compound is known in the art, for example, Chul-bae kim, et al. , Applied Chemistry . It can synthesize
  • the spiro compound synthesized as described above or prepared by a conventional method can be confirmed whether synthesized through GC-MS, 1 H-NMR and 13 C-NMR, especially the central carbon characteristic of SOC compounds It appears around 155 ppm in 13 C-NMR.
  • the siloxane compound is at least one selected from the group consisting of Chemical Formulas 6 to 8.
  • l is an integer of 1 to 20
  • R 14 is each independently substituted with an epoxy group or substituted with C 1-5 alkoxy C 1-4 alkyl, C 4-8 epoxycycloalkyl substituted with C 1 Alkyl of -4 , alkyl of (meth) acrylate C 1-4 or alkenyl of C 2-5 .
  • R 14 may be each independently glycidyl etherpropyl, epoxycyclohexylethyl, methacrylate ethyl or ethenyl. More specifically, each R 14 may be independently one selected from the group consisting of Formulas 19 to 22:
  • the siloxane compound may have a weight average molecular weight of 1,000 to 50,000 g / mol.
  • the siloxane compound can be confirmed whether the synthesis through IR, 1 H-NMR, 29 Si-NMR.
  • the IR analysis confirmed the Si-OH content in the vicinity of 3,000 to 3,400 cm -1 , and the Si-O in the vicinity of 1,000 to 1,100 cm -1 and the Si-O-Si peak observed at 1,100 to 1,200 cm -1 . You can check the location.
  • the photocurable coating composition may include a spiro compound and a siloxane compound in a weight ratio of 1: 0.3 to 1:19, or 1: 0.5 to 1: 9 by weight.
  • the coating composition may further include additives such as an initiator, a solvent, a leveling agent, and the like, which may typically be included in the photocurable coating composition.
  • the coating composition may further include one or more additives selected from the group consisting of an initiator, a solvent and a leveling agent.
  • It may include 30 to 80% by weight of the solvent based on the total weight of the coating composition.
  • based on 100 parts by weight of the coating composition may include 1 to 10 parts by weight of the initiator and 0.05 to 5 parts by weight of the leveling agent.
  • the initiator may be used by selecting any one of commercially available initiators. Specifically, the initiator may use any one selected from the group consisting of a thermal initiator, a cationic initiator, a radical initiator and a photoinitiator according to the curing system, and in the case of a dual curing system, the mixed use of the thermal initiator and the photoinitiator may be used. It is possible.
  • the photoinitiator examples include benzoin methyl ether, benzoin isopropyl ether, anisoin methyl ether, benzoin, benzyl ketal, and the like.
  • the cation initiator is, for example, hexafluoroantimonate, diphenyl (4-phenylthio) phenylsulfonium hexafluorophosphate, (phenyl) [4- (2-methylpropyl) phenyl]-iodonium Hexafluorophosphate, (thiodi-4,1-phenylene) bis (diphenylsulfonium) dihexafluoroantimonate, triphenylsulfonium triflate or (thiodi-4,1-phenylene) bis ( Diphenylsulfonium) dihexafluorophosphate, and the like.
  • the thermal initiator may include, for example, a peroxide system including benzoyl peroxid
  • the solvents include monohydric alcohols, polyhydric alcohols, alkyl ethers of polyhydric alcohols, alkyl ether acetates of polyhydric alcohols, ethers, cyclic ethers, alkanes, alkoxyalkanes, aromatic hydrocarbons, ketones, esters, and the like. Solvents selected from the group consisting of water may be used alone or in combination of two or more thereof.
  • Examples of the monohydric alcohols include 1-butyl alcohol, 2-butyl alcohol, isobutyl alcohol, tert-butyl alcohol, 1-pentanol, 2-pentanol, 3-pentanol, tert-amyl alcohol, Neopentyl alcohol, 2-methyl-1-butanol, 3-methyl-1-butanol, 3-methyl-3-pentanol, cyclopentanol, 1-hexanol, 2-hexanol, 3-hexanol, 2, 3-dimethyl-2-butanol, 3,3-dimethyl-1-butanol, 3,3-dimethyl-2-butanol, 2-diethyl-1-butanol, 2-methyl-1-pentanol, 2-methyl- 2-pentanol, 2-methyl-3-pentanol, 3-methyl-1-pentanol, 3-methyl-2-pentanol, 3-methyl-3-pentanol, 4-methyl-1-pentanol, 4-methyl-2
  • polyhydric alcohols examples include ethylene glycol, propylene glycol, 4-hydroxy-4-methyl-2-pentanol, 2-ethyl-1,3-hexanediol, 1,3-butanediol, 1,2 -Propanediol, 1,3-propanediol, 1,2-heptanediol, and the like, and may be a divalent alcohol having 4 to 8 carbon atoms.
  • the alkyl ethers of the polyhydric alcohols are, for example, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol ethylmethyl ether, propylene glycol monomethyl Ether, propylene glycol monoethyl ether, and the like.
  • the alkyl ether acetates of the polyhydric alcohols may be, for example, ethylene glycol ethyl ether acetate, diethylene glycol ethyl ether acetate, propylene glycol ethyl ether acetate, propylene glycol monomethyl ether acetate, or the like.
  • the ethers may be, for example, diethyl ether, dipropyl ether, diisopropyl ether, butyl methyl ether, butyl ethyl ether, butyl propyl ether, dibutyl ether, diisobutyl ether, tert-butyl-methyl ether, tert-butylethyl ether, tert-butylpropyl ether, di-tert-butyl ether, dipentyl ether, diisoamyl ether, cyclopentylmethyl ether, cyclohexylmethyl ether, cyclopentylethyl ether, cyclohexylethyl ether, cyclopentyl Propyl ether, cyclopentyl-2-propyl ether, cyclohexylpropyl ether, cyclohexyl-2-propyl ether, cyclopentyl butyl ether,
  • the cyclic ethers may be, for example, tetrahydrofuran, dioxane or the like.
  • the alkanes may be, for example, decane, dodecane, undecane, or the like.
  • the alkoxy alkanes may be dialkoxyalkanes, trialkoxyalkanes or tetraalkoxyalkanes having 3 to 16 carbon atoms.
  • the alkoxy alkanes are, for example, dimethoxymethane, diethoxymethane, dibutoxymethane, trimethoxymethane, triethoxymethane, tripropoxymethane, 1,1-dimethoxyethane and 1,2-dimethane.
  • aromatic hydrocarbons examples include benzene, toluene and xylene
  • ketones include acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone and 4-hydroxy-4.
  • esters examples include ethyl acetate (ethyl acetate), butyl acetate, ethyl 2-hydroxypropionate, methyl 2-hydroxy-2-methylpropionate, ethyl 2-hydroxy-2-methylpropionate and ethoxy Ethyl acetate, ethyl hydroxyacetate, methyl 2-hydroxy-3-methylbutyrate, methyl 3-methoxypropionate, ethyl 3-methoxypropionate, ethyl 3-ethoxypropionate, methyl 3-ethoxypropionate, butyl Lactone, caprolactone and the like.
  • the solvent may be at least one selected from the group consisting of monohydric alcohols, ethers, cyclic ethers, alkyl ethers of polyhydric alcohols, alkyl ether acetates of polyhydric alcohols, ketones, aromatic hydrocarbons and esters. have. More specifically, the solvent includes monohydric alcohols having 9 to 11 carbon atoms, alkyl ethers of polyhydric alcohols having 4 to 10 carbon atoms, ketones having 2 to 6 carbon atoms, aromatic hydrocarbons having 6 to 10 carbon atoms, and esters having 3 to 7 carbon atoms. It may be one or more selected from the group consisting of.
  • leveling agents include BYK-Chemie's BYK 371, BYK 377, BYK 353, BYK 356, BYK 359, BYK 361, BYK 067 and BYK 141, Tego Chemie's Tego Rad 2200, Tego Rad 2500, Tego Glide 410, Tego Glide 435 and Tego Glide 453, and TS 100 and OK 607 available from Daeguusa.
  • the present invention provides a coating film prepared using the photocurable coating composition as described above.
  • the coating film may be prepared by coating and curing the photocurable coating composition.
  • the coating is spin coating, wet coating, spray coating, dip coating, roll coating, slow-die coating the composition for the photocurable coating of the present invention on an object to be coated, for example, a silicon wafer, a glass substrate, a plastic film, etc. It may be carried out by coating, bar coating or the like.
  • the curing method can be used without any particular limitation as long as it can be used for photocuring, for example, can be cured with a metal halide lamp, a high pressure mercury lamp, a mercury short arc lamp, an ultraviolet lamp.
  • the coating film has high transparency and excellent surface hardness, adhesiveness, and flexibility, so that the coating film can be used in various applications such as flexible displays, liquid crystal displays, OLED displays, molded products, coatings, dental materials, and the like. Can be.
  • Triethylamine (223 g) and toluene (2,000 mL) were then added to the intermediate (328 g). After cooling to 5 ° C. in argon atmosphere, distilled methacryloyl chloride (209 g) and toluene (700 mL) were added dropwise. After stirring for 18 hours at room temperature and filtered to remove the amine hydrochloride precipitate (amine hydrochloride precipitate). Thereafter, the solvent was removed under reduced pressure to obtain a spiro compound of Formula 13.
  • Vinyltrimethoxysilane (204.5 g) was dissolved in 32.79 mL of toluene and 32.79 mL of isopropanol, water (72 g) and sodium bicarbonate (12.1 g) were added and stirred at room temperature for 12 hours. Thereafter, the reaction product was distilled under reduced pressure to obtain a siloxane compound represented by Chemical Formula 6, in which R 14 was Chemical Formula 22.
  • the weight average molecular weight and molecular formula of the spiro compound prepared in Synthesis Examples 1 to 9 and the siloxane compound prepared in Synthesis Examples 10 to 12 were determined using a GC-MS spectrometer (Waters), and the nuclear magnetic resonance spectrum (NMR ) (manufacturer: Varian) and FT-IR (Manufacturer: PerkinElmer) for use in the synthesis examples 1 to 9 of the spy to obtain the 1 H-NMR and 13 C-NMR spectrum of the compound. Furthermore, 1 H-NMR and 29 Si-NMR spectra of the siloxane compounds of Synthesis Examples 10 to 12 were obtained.
  • a photocurable coating composition was prepared in the same manner as in Example 1, except that the spiro compound (Compound 10) of Synthesis Example 2 was used instead of the spiro compound of Synthesis Example 1.
  • a photocurable coating composition was prepared in the same manner as in Example 1, except that the spiro compound (Compound 14) of Synthesis Example 6 was used instead of the spiro compound of Synthesis Example 1.
  • a photocurable coating composition was prepared in the same manner as in Example 4, except that the spiro compound (Compound Formula 13) of Synthesis Example 5 was used instead of the spiro compound of Synthesis Example 4.
  • a photocurable coating composition was prepared in the same manner as in Example 4, except that the spiro compound (Compound 16) of Synthesis Example 8 was used instead of the spiro compound of Synthesis Example 4.
  • a photocurable coating composition was prepared in the same manner as in Example 4, except that the spiro compound (Compound 17) of Synthesis Example 9 was used instead of the spiro compound of Synthesis Example 4.
  • a photocurable coating composition was prepared in the same manner as in Example 8, except that the spiro compound (Compound 12) of Synthesis Example 4 was used instead of the spiro compound of Synthesis Example 3.
  • a photocurable coating composition was prepared in the same manner as in Example 11, except that the spiro compound (Compound 14) of Synthesis Example 6 was used instead of the spiro compound of Synthesis Example 7.
  • a photocurable coating composition was prepared in the same manner as in Example 11, except that the spiro compound (Compound Formula 16) of Synthesis Example 8 was used instead of the spiro compound of Synthesis Example 7.
  • a photocurable coating composition was prepared in the same manner as in Example 14, except that the spiro compound (Compound 10) of Synthesis Example 2 was used instead of the spiro compound of Synthesis Example 7.
  • a photocurable coating composition was prepared in the same manner as in Example 16, except that the spiro compound (Compound 12) of Synthesis Example 4 was used instead of the spiro compound of Synthesis Example 3.
  • a photocurable coating composition was prepared in the same manner as in Example 16, except that the spiro compound (Compound Formula 13) of Synthesis Example 5 was used instead of the spiro compound of Synthesis Example 3.
  • a photocurable coating composition was prepared in the same manner as in Example 11, except that the compound having the structure of Chemical Formula 18 (obtained from Chemtik) was used instead of the spiro compound of Synthesis Example 7.
  • a photocurable coating composition was prepared in the same manner as in Example 19, except that the siloxane compound of Synthesis Example 11 was used instead of the siloxane compound of Synthesis Example 10.
  • a coating composition was prepared in the same manner as in Comparative Example 1, except that the spiro compound of Synthesis Example 5 was used instead of the spiro compound of Synthesis Example 3.
  • a photocurable coating composition was prepared in the same manner as in Example 17, except that ENTIS Corporation UP118 was used instead of the siloxane compound.
  • a photocurable coating composition was prepared in the same manner as in Example 18, except that U15HA from Kyoeisha Chemical was used instead of the siloxane compound.
  • a photocurable coating composition was prepared in the same manner as in Example 15, except that DGEBA (diglycidyl ether of bisphenol-A, manufacturer: Kukdo Chemical, product name: YD128) was used instead of the siloxane compound.
  • DGEBA diglycidyl ether of bisphenol-A, manufacturer: Kukdo Chemical, product name: YD1278
  • a photocurable coating composition was prepared in the same manner as in Example 14, except that DGEBA (diglycidyl ether of bisphenol-A, manufacturer: Kukdo Chemical, product name: YD128) was used instead of a spiro compound.
  • DGEBA diglycidyl ether of bisphenol-A, manufacturer: Kukdo Chemical, product name: YD1278
  • Polyethylene terephthalate (thickness 250 ⁇ m) was used as the base of the coating.
  • the surface of the substrate was washed with isopropyl alcohol, followed by spin coating the compositions of Examples 1-20 and Comparative Examples 1-7. At this time, the temperature was maintained at 25 °C, humidity 50%.
  • the coated substrate was dried at 60 ° C. for 3 minutes using a dryer, and the coating film was prepared by irradiating the light amount of the ultraviolet lamp with 1,000 mJ / cm 2.
  • the coating films prepared from the compositions of Examples 1 to 20 and Comparative Examples 1 to 7 were evaluated for the following items.
  • the test specimen was cut into 100 mm x 100 mm (width x length), and the evaluation results are shown in Tables 1 and 2 below.
  • the coating film prepared from the photocurable coating composition comprising the spiro compound and the siloxane compound of the present invention is excellent in surface hardness, adhesion.
  • the coating film prepared from the composition of the embodiment has a high transparency and at the same time excellent in surface hardness, adhesion, flexibility, etc. can effectively prevent cracks or interfacial film removal due to shrinkage during curing, such as a flexible display, a liquid crystal display, Various applications include photocuring systems such as OLED displays, molded articles, coatings, dental materials, and the like.
  • the coating film prepared from the composition for the photocurable coating of Comparative Examples 1 to 7 has a surface hardness of B or less, or a lot of shrinkage after coating is insufficient flexibility, it was not suitable as a flexible display film.

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  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
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  • Chemical Kinetics & Catalysis (AREA)
  • Paints Or Removers (AREA)
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Abstract

La présente invention concerne une composition photo-durcissable pour le revêtement et un film de revêtement, la composition photo-durcissable pour le revêtement pouvant former un film de revêtement présentant une transparence élevée et d'excellentes souplesse, dureté de surface, et adhésion. De plus, le film de revêtement peut être appliqué de diverses manières, dû à ses excellentes propriétés physiques, dans plusieurs domaines en utilisant un système de photo-durcissement, tel qu'un afficheur souple, un afficheur à cristaux liquides, un afficheur DELO, un produit moulé, un revêtement, et un matériau dentaire.
PCT/KR2018/002113 2017-04-28 2018-02-21 Composition photo-durcissable pour revêtement et film de revêtement WO2018199450A1 (fr)

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KR10-2017-0055478 2017-04-28

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Citations (6)

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Publication number Priority date Publication date Assignee Title
WO1993007230A1 (fr) * 1991-10-09 1993-04-15 The Procter & Gamble Company Composition dentaire resineuse a base de polysiloxanes polymerisables
JPH09202873A (ja) * 1996-01-29 1997-08-05 Toyo Ink Mfg Co Ltd 感エネルギー線酸発生剤、感エネルギー線酸発生剤組成物、硬化性組成物およびその硬化物
CN103703029A (zh) * 2011-07-11 2014-04-02 株式会社德山 光致变色固化性组合物
KR20140050296A (ko) * 2012-10-19 2014-04-29 (주) 개마텍 실세스퀴옥산을 포함하는 조성물과 그 제조 방법, 및 이를 이용한 하드 코팅막과 그 제조 방법
KR20160056188A (ko) * 2014-11-11 2016-05-19 에스케이이노베이션 주식회사 광경화성 하드코팅층 형성용 조성물
KR20170052245A (ko) * 2015-11-04 2017-05-12 (주) 개마텍 광경화 코팅용 조성물 및 코팅막

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6458865B2 (en) 1999-01-15 2002-10-01 Curators Of The University Of Missouri Photopolymerizable vinyl ether based monomeric formulations and polymerizable compositions which may include certain novel spiroorthocarbonates
JP2010510975A (ja) 2006-11-28 2010-04-08 ピュラック バイオケム ビー．ブイ． 安定なラクチド粒子

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1993007230A1 (fr) * 1991-10-09 1993-04-15 The Procter & Gamble Company Composition dentaire resineuse a base de polysiloxanes polymerisables
JPH09202873A (ja) * 1996-01-29 1997-08-05 Toyo Ink Mfg Co Ltd 感エネルギー線酸発生剤、感エネルギー線酸発生剤組成物、硬化性組成物およびその硬化物
CN103703029A (zh) * 2011-07-11 2014-04-02 株式会社德山 光致变色固化性组合物
KR20140050296A (ko) * 2012-10-19 2014-04-29 (주) 개마텍 실세스퀴옥산을 포함하는 조성물과 그 제조 방법, 및 이를 이용한 하드 코팅막과 그 제조 방법
KR20160056188A (ko) * 2014-11-11 2016-05-19 에스케이이노베이션 주식회사 광경화성 하드코팅층 형성용 조성물
KR20170052245A (ko) * 2015-11-04 2017-05-12 (주) 개마텍 광경화 코팅용 조성물 및 코팅막

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