WO2005092826A1 - Nouveau compose de phenol et nouvelle resine epoxy derivable dudit compose de phenol - Google Patents

Nouveau compose de phenol et nouvelle resine epoxy derivable dudit compose de phenol Download PDF

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Publication number
WO2005092826A1
WO2005092826A1 PCT/JP2005/004625 JP2005004625W WO2005092826A1 WO 2005092826 A1 WO2005092826 A1 WO 2005092826A1 JP 2005004625 W JP2005004625 W JP 2005004625W WO 2005092826 A1 WO2005092826 A1 WO 2005092826A1
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WIPO (PCT)
Prior art keywords
epoxy resin
general formula
group
phenol compound
formula
Prior art date
Application number
PCT/JP2005/004625
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English (en)
Japanese (ja)
Inventor
Mitsuo Akutsu
Masaaki Shimizu
Yoshie Makabe
Naomi Sato
Original Assignee
Asahi Denka Co., Ltd.
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
Application filed by Asahi Denka Co., Ltd. filed Critical Asahi Denka Co., Ltd.
Priority to JP2006519423A priority Critical patent/JP4698586B2/ja
Publication of WO2005092826A1 publication Critical patent/WO2005092826A1/fr

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Classifications

    • 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
    • C08G59/20—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 epoxy compounds used
    • C08G59/22—Di-epoxy compounds
    • C08G59/24—Di-epoxy compounds carbocyclic
    • C08G59/245—Di-epoxy compounds carbocyclic aromatic
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
    • C07C39/12—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic with no unsaturation outside the aromatic rings
    • C07C39/17—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic with no unsaturation outside the aromatic rings containing other rings in addition to the six-membered aromatic rings, e.g. cyclohexylphenol
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
    • C07D303/02—Compounds containing oxirane rings
    • C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
    • C07D303/18—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by etherified hydroxyl radicals
    • C07D303/28—Ethers with hydroxy compounds containing oxirane rings

Definitions

  • the present invention relates to a novel phenolic compound and a novel epoxy resin derivable from the phenolic compound, and more particularly to a phenolic compound suitably used as a synthetic resin raw material and the like, a paint, an adhesive, a molded article, and the like.
  • the present invention relates to an epoxy resin which is useful as a useful material and can be derived from the phenol compound. Background art
  • Polyphenol compounds are used as raw materials for synthetic resins such as phenolic resins, epoxy resins, polycarbonate resins, and polyester resins, epoxy curing agents, color developers and discoloration inhibitors used for thermal recording, and raw materials for electronic materials. It is useful, and also useful as an additive such as an antioxidant, a bactericide, and a fungicide.
  • Epoxy resins are widely used as materials for coatings, adhesives, molded products, and the like because of their excellent adhesive properties, heat resistance, chemical resistance, electrical properties, mechanical properties, and the like. It is also widely used in the electrical and electronic fields such as IC sealing materials, laminate materials, and electrical insulating materials.
  • Patent Document 1 proposes a terpendiphenol phenol compound
  • Patent Document 2 discloses a 4-substituted cyclohexylidenebis. Although phenols have been proposed, these compounds have not yet been able to satisfy the above requirements.
  • Patent Document 3 proposes a recording material using a bisphenol compound such as 4_ [1,1 bis (4-hydroxyphenyl) ethyl] biphenyl as an electron-accepting compound.
  • Patent Document 4 discloses that biphenylalkylidene-4,4,1-bisphenol A polycarbonate-based copolymer derived from a compound has been proposed.
  • Patent Document 5 proposes a thermosensitive recording medium using methyl-phenylmethylidenebisphenol as a color developer.
  • Reference 6 proposes a heat-sensitive recording material using a cyclohexylmethylene 1,4,4,1-bisphenol compound or the like as an electron-accepting compound. These have not yet been able to satisfy the above requirements.
  • Patent Document 1 JP-A-8-198791
  • Patent Document 2 Japanese Patent Application Laid-Open No. 2003-146926
  • Patent Document 3 JP-A-62-122782
  • Patent Document 4 JP-A-63-43923
  • Patent Document 5 JP-A-63-247085
  • Patent Document 6 JP-A-5-42769
  • an object of the present invention is to provide a phenol compound suitably used as a synthetic resin raw material and the like, and to provide an epoxy resin useful as a material used for paints, adhesives, molded products, and the like. It is in.
  • the present invention provides a phenolic conjugate represented by the following general formula (I). [0011] [Formula 1]
  • Cy represents a cycloalkyl group having 3 to 10 carbon atoms
  • X represents a hydrogen atom, a phenyl group which can be substituted by an alkyl group having 1 to 10 carbon atoms, or a carbon atom having 3 to 10 carbon atoms.
  • the present invention provides an epoxy resin represented by the following general formula (II).
  • the cycloalkyl group having 3 to 10 carbon atoms represented by Cy includes cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclohexanol, cycloheptyl, cyclooctyl , Cyclononinole, cyclodecyl and the like.
  • Examples of the alkyl group having 1 to 10 carbon atoms represented by Y and Z include methynole, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, hexyl, heptyl, octyl, Isooctyl, tertiary octyl, 2-ethylhexyl, nonyl, isononyl, decyl, isodecyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, etc.
  • Linear, branched and cyclic alkyl groups are mentioned.
  • Examples of the cycloalkyl group having 3 to 10 carbon atoms represented by X include the same groups as those exemplified as Cy, and 1 to 10 carbon atoms capable of substituting the phenyl group represented by X.
  • As the ten alkyl groups the same as those exemplified as Y and Z can be mentioned.
  • Examples of the phenol compound of the present invention include the following compounds.
  • the method for producing the phenolic compound of the present invention is not particularly limited.
  • a mixture of a ketone compound (1) and a phenolic compound (2) may be used. It can be easily produced by reacting in the presence of an acidic catalyst.
  • Examples of the acidic catalyst used in the above reaction include methanesulfonic acid, benzenesulfonic acid, m-xylenesulfonic acid, p-toluenesulfonic acid, and hydroxymethylsulfonic acid.
  • Sulfonic acids such as 2-hydroxyethylsulfonic acid, hydroxypropylsulfonic acid, trifluoromethanesulfonic acid, sulfosalicylic acid, and sulfophthalic acid; sulfuric acid, sulfuric anhydride, fuming sulfuric acid, sulfuric acid, fluorosulfuric acid, hydrochloric acid, chloride
  • sulfuric acid sulfuric anhydride
  • fuming sulfuric acid sulfuric acid, fluorosulfuric acid, hydrochloric acid, chloride
  • Examples include hydrogen gas, oxalic acid, formic acid, phosphoric acid, trichloroacetic acid, trifluoroacetic acid, heterotungstic acid, phosphotungstic acid, etc., and strongly acidic ion exchange resins.
  • a mercaptan catalyst can be used to promote the reaction.
  • the mercaptan catalyst include methyl mercaptan, ethyl mercaptan, propyl mercaptan, butyl mercaptan, octyl mercaptan, Alkyl mercaptans such as dodecyl mercaptan and 1,6-hexanedithiol; aromatic mercaptans such as thiophenol and thiotalesol; mercaptoacetic acid (thiodalicholate), 3-mercaptopropionic acid, mercaptunedecanoic acid, thiobenzoic acid and the like Organic acids; heterocyclic mercaptans such as 2-mercaptobenzothiazole; hydrogen sulfide and the like.
  • the phenolic compound (2) is preferably used in an amount of 1 mol or more, particularly 2 to 10 mol, per 1 mol of the ketone compound (1).
  • the preferred mercapto catalyst is particularly suitable for 1 mole of ketone compound (1). It is preferable to use 0.001 to 1.0 mole.
  • a general-purpose solvent can be used.
  • the solvent include aromatic hydrocarbon solvents such as toluene, xylene, and cumene; turpentine, D-limonene, and vinylene. Terpene hydrocarbon oils; mineral spirits, SUZOL # 310 (Cosmo Matsuyama Petroleum Co., Ltd.), Solvesso # 100 (Exon Chemical Co., Ltd.), etc .; paraffinic solvents; methanol, ethanol, etc.
  • Solvents Ethyl acetate and other ester solvents; Dichloroethane, carbon tetrachloride, chlorohonolem, trichloroethylene, methylene chloride, halogenated solvents such as chlorobenzene; cyclic ether solvents such as tetrahydrofuran and dioxane; aniline, triethylenamine, pyridine and dioxane Acetic acid, acetonitrile, carbon disulfide and the like.
  • This reaction is preferably carried out at a temperature in the range of 0 to 200 ° C, particularly 10 to 100 ° C. If the temperature is lower than 0 ° C, the reaction becomes slow and a long reaction time is required.If the temperature exceeds 200 ° C, many side reactions occur. Not preferred. When the reaction temperature is 0 to 200 ° C, the reaction time is usually selected from a range of several minutes to several tens of hours.
  • the phenolic compound of the present invention includes a phenolic resin, an epoxy resin, a polycarbonate resin, a polyester resin, a polysulfone resin, a polyimide resin, a polyamideimide resin, a polyesterimide resin, a polybismaleimide resin, a polyarylate resin, a polyacetal resin, and the like.
  • Examples of the epoxy resin of the present invention represented by the general formula (II) include the following compounds.
  • the method for producing the epoxy resin of the present invention is not particularly limited.
  • the epoxy resin in which n in the above general formula (II) is 0 is as shown in the following [Chemical Formula 20].
  • the compound can be easily produced by reacting the phenolic conjugate (I) of the present invention with epichlorohydrin (3) in the presence of an alkali and a Lewis acid or a phase transfer catalyst.
  • alkali used in the above reaction examples include sodium hydroxide, potassium hydroxide, calcium hydroxide and the like.
  • the Lewis acid may be an acid as exemplified above. Catalyst, tin tetrachloride, boron trifluoride, titanium tetrachloride, activated clay, aluminum chloride, magnesium chloride, potassium permanganate, potassium chromate and the like.
  • phase transfer catalyst examples include, for example, tetramethylammonium chloride, tetrabutylammonium chloride, methyltrioctylammonium chloride, methyltridecylammonium chloride, benzyltriethylammonium chloride, and benzyltriethylammonium chloride.
  • epichronorehydrin is a hydroxyl group of the phenol compound (I) of the present invention.
  • 1 - 5 preferably fixture interlayer transfer catalyst to moles, compared 1 equivalent of hydroxyl group of the phenol compound of the present invention (I), 0. 01- 10 mole 0/0, especially 0.5 2 5 mole 0 / 0, preferably used.
  • the epoxy resin of the above general formula (II) where n is 110 can also be produced according to the above reaction when n is 0, and in this case, the amount of epichlorohydrin used May be appropriately selected.
  • the epoxy resin having n of 110 in the general formula (II) is reacted with the epoxy resin having n force S 0 in the general formula (II) and the phenol compound of the present invention represented by the general formula (II). Alternatively, it can be manufactured.
  • the solvents exemplified as the solvents that can be used for producing the phenolic compound (I) of the present invention can be used.
  • Epicronorehydrin of supercharged IJ can also be used as a solvent.
  • This reaction is preferably carried out at a temperature in the range of 20 to 100 ° C, particularly 30 to 60 ° C. If the temperature is lower than 20 ° C, the reaction slows down and a long reaction time is required.If the temperature exceeds 100 ° C, many side reactions occur. Is not preferred.
  • the reaction time is usually selected from the range of several minutes to several tens of hours when the reaction temperature is 20-100 ° C.
  • the epoxy resin of the present invention is usually used in combination with a curing agent for an epoxy resin, and examples of the curing agent include polyalkylene such as diethylenetriamine, triethylenetriamine, and tetraethylenepentamine.
  • polyalkylene such as diethylenetriamine, triethylenetriamine, and tetraethylenepentamine.
  • Polyamines such as 1,2-diaminocyclohexane, 1,4-diamino-3,6-diethylcyclohexane, isophoronediamine; m-xylylenediamine, diaminodiphenylmethane, diamino And polyamines such as aromatic polyamines such as diphenylsulfone.
  • these polyamines and various epoxy resins such as glycidyl ethers such as phenylglycidyl ether, butyldaricidyl ether, bisphenol A-diglycidyl ether, and bisphenol F-diglycidyl ether; Polyepoxy modified product produced by reacting the polyamine with a conventional method; produced by reacting these polyamines with carboxylic acids such as phthalic acid, isophthalic acid and dimer acid by a conventional method.
  • glycidyl ethers such as phenylglycidyl ether, butyldaricidyl ether, bisphenol A-diglycidyl ether, and bisphenol F-diglycidyl ether
  • Polyepoxy modified product produced by reacting the polyamine with a conventional method
  • carboxylic acids such as phthalic acid, isophthalic acid and dimer acid by a conventional method.
  • Amidation-modified product These polyamines are combined with aldehydes such as formaldehyde and phenols having at least one aldehyde-reactive site in the nucleus such as phenol, cresol, xylenol, tert-butylphenol, resorcin, etc. in a conventional manner.
  • aldehydes such as formaldehyde and phenols having at least one aldehyde-reactive site in the nucleus such as phenol, cresol, xylenol, tert-butylphenol, resorcin, etc.
  • a latent curing agent such as disiandiamide, acid anhydride and imidazoles can be used.
  • a curing catalyst When using the epoxy resin of the present invention, if necessary, a curing catalyst; a reactive or non-reactive material such as monodalicydyl ethers, octyl phthalate, dibutyl phthalate, benzyl alcohol, coal tar, etc.
  • Diluent plasticizer
  • glass fiber carbon fiber, cellulose, ky sand, cement, kaolin, clay, aluminum hydroxide, bentonite, talc, silica, finely divided silica, titanium dioxide, carbon black, graphite, oxidized Fillers or pigments such as iron and bituminous substances; ⁇ -aminopropyltriethoxysilane, ⁇ - / 3- (aminoethyl) -1- ⁇ - aminopropyltriethoxysilane, N-j3- (aminoethynole) -1- ⁇ , -1 / 3— (aminoethyl) _ ⁇ —aminopropyltriethoxysilane , ⁇ —anilinopropyltriethoxysilane , ⁇ -glycidoxypropyltriethoxysilane, j3_ (3,4-epoxycyclohexyl) ethyltrieth
  • the epoxy resin of the present invention can be used as a raw material for various modified products such as urethane-modified, silica-modified, phosphoric-acid-modified, amine-modified, and (meth) acrylic-acid-modified.
  • the epoxy resin of the present invention or a modified product thereof is, for example, a paint or an adhesive for concrete, cement mortar, various metals, leather, glass, rubber, plastic, wood, cloth, paper, etc .; Adhesive labels, frozen food labels, removable labels, POS labels, adhesive wallpaper, adhesive for floor coverings; Art paper, lightweight coated paper, cast coated paper, coated paperboard, carbonless copier, impregnated paper, etc .; Sizing agents such as natural fibers, synthetic fibers, glass fibers, carbon fibers, and metal fibers; fiber treatment agents such as anti-fray agents and processing agents; building materials such as sealing materials, cement admixtures, and waterproofing materials; It can be used for a wide range of applications such as sealing agents for plastics.
  • the organic layer obtained by oil-water separation was washed with 3 kg of dilute hydrochloric acid, and further washed three times with 3 kg of water. Remove with anhydrous sodium sulfate After water, the solvent was distilled off and recrystallized from hexane to obtain 563.5 g (yield 75%) of white crystals.
  • the obtained white crystals were analyzed by ⁇ -NMR and IR.
  • the product showed a 1 H-NMR chemical shift and IR absorption, and was confirmed to be the desired ketone compound K-11.
  • the melting point of the white crystal was 86.9 ° C (differential heat peak top).
  • the yellow solid epoxy resin was analyzed by 1 NMR and IR, it showed the following 1 H-NMR chemical shift and IR absorption, and was confirmed to be the intended compound E-1. Was. Further, the yellow solid epoxy resin had a melting point of 64.2 ° C (differential heat peak top).
  • the glass transition temperature (Tg) of the cured product was 155 ° C.
  • Epicoat 834 manufactured by Japan Epoxy Resin; Bisphenol A type epoxy resin
  • Adekano donor EH-3326 64.4 g
  • Adekano donor EH-3326 64.4 g
  • triphenylinolephosphine 1 ⁇ 66 g
  • the glass transition temperature (Tg) of the cured product was 130 ° C.
  • the obtained orange solid epoxy resin was analyzed by ⁇ -NMR and IR. As a result, it showed the following chemical shift of 1 H-NMR and absorption of IR, and was confirmed to be the intended compound HE-2. Was done.
  • the phenolic conjugate according to the present invention is useful as a raw material for epoxy resins and the like. Further, the epoxy resin derivable from the phenolic conjugate can provide a cured product having excellent cured properties and water resistance.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Epoxy Resins (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Epoxy Compounds (AREA)

Abstract

Il est prévu un composé de phénol représenté par la formule générale (I) ci-dessous que l’on utilise de préférence comme matière première pour résines synthétiques et autres. Il est également prévu une résine époxy représentée par la formule générale (II) ci-dessous, servant de matériau pour compositions de revêtement, adhésifs, moulages et autres. (I) (Dans la formule, Cy représente un groupe cycloalkyle ayant 3 à 10 atomes de carbone ; X représente un atome d’hydrogène, un groupe phényle que l’on peut substituer par un groupe alkyle ayant 1 à 10 atomes de carbone, ou un groupe cycloalkyle ayant 3 à 10 atomes de carbone ; Y et Z représentent indépendamment un groupe alkyle ayant 1 à 10 atomes de carbone ; p représente un nombre de 0 à 5 ; et r représente un nombre de 0 à 4.) (I) (Dans la formule, Cy, X, Y, Z, p et r sont tels que définis ci-dessus pour la formule (I) ; et n représente un nombre de 0 à 10.)
PCT/JP2005/004625 2004-03-25 2005-03-16 Nouveau compose de phenol et nouvelle resine epoxy derivable dudit compose de phenol WO2005092826A1 (fr)

Priority Applications (1)

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JP2006519423A JP4698586B2 (ja) 2004-03-25 2005-03-16 新規フェノール化合物及び該フェノール化合物から誘導し得る新規エポキシ樹脂

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JP2004-090129 2004-03-25
JP2004090129 2004-03-25

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CN (1) CN100386298C (fr)
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Cited By (14)

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Publication number Priority date Publication date Assignee Title
WO2006030630A1 (fr) * 2004-09-17 2006-03-23 Asahi Denka Co., Ltd. Composition de résine développable dans un milieu alcalin
WO2006030631A1 (fr) * 2004-09-17 2006-03-23 Toppan Printing Co., Ltd. Composition de résine photosensible développable alcaline colorée, et filtre de couleur utilisant ladite composition de résine photosensible développable alcaline colorée
WO2006137257A1 (fr) * 2005-06-20 2006-12-28 Toppan Printing Co., Ltd. Composition de résine photosensible colorée développable par un alcali et filtres colorés fabriqués en utilisant celle-ci
JP2007034279A (ja) * 2005-06-20 2007-02-08 Adeka Corp アルカリ現像性感光性樹脂組成物
JP2007183495A (ja) * 2006-01-10 2007-07-19 Toppan Printing Co Ltd アルカリ現像型感光性樹脂組成物を用いて形成した液晶分割配向制御用突起付き基板、及び液晶表示装置
JP2007204596A (ja) * 2006-02-01 2007-08-16 Adeka Corp エポキシ樹脂、アルカリ現像性樹脂組成物及びアルカリ現像性感光性樹脂組成物
JP2007206351A (ja) * 2006-02-01 2007-08-16 Adeka Corp アルカリ現像性感光性樹脂組成物
JP2007246638A (ja) * 2006-03-15 2007-09-27 Adeka Corp エポキシ樹脂、アルカリ現像性樹脂組成物及びアルカリ現像性感光性樹脂組成物
WO2008078445A1 (fr) * 2006-12-26 2008-07-03 Adeka Corporation Composés polymérisables et compositions polymérisables
JP2008208312A (ja) * 2007-02-28 2008-09-11 Adeka Corp フェノール樹脂、エポキシ樹脂、アルカリ現像性樹脂組成物及びアルカリ現像性感光性樹脂組成物
WO2011068643A3 (fr) * 2009-12-02 2011-08-18 Dow Global Technologies Llc Compositions de composites
US8937145B2 (en) 2009-12-02 2015-01-20 Dow Global Technologies Llc Epoxy resin compositions
US8937114B2 (en) 2009-12-02 2015-01-20 Dow Global Technologies Llc Coating compositions
JP7465673B2 (ja) 2020-02-25 2024-04-11 株式会社Adeka 重合体、成形体及び光学材料

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Cited By (25)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2006030631A1 (fr) * 2004-09-17 2006-03-23 Toppan Printing Co., Ltd. Composition de résine photosensible développable alcaline colorée, et filtre de couleur utilisant ladite composition de résine photosensible développable alcaline colorée
WO2006030630A1 (fr) * 2004-09-17 2006-03-23 Asahi Denka Co., Ltd. Composition de résine développable dans un milieu alcalin
US7846622B2 (en) 2004-09-17 2010-12-07 Toppan Printing Co., Ltd. Alkali-developable, colored photosensitive resin composition and color filter using the alkali-developable, colored photosensitive resin composition
JPWO2006137257A1 (ja) * 2005-06-20 2009-01-08 凸版印刷株式会社 着色アルカリ現像型感光性樹脂組成物、及び該着色アルカリ現像型感光性樹脂組成物を用いたカラーフィルタ
WO2006137257A1 (fr) * 2005-06-20 2006-12-28 Toppan Printing Co., Ltd. Composition de résine photosensible colorée développable par un alcali et filtres colorés fabriqués en utilisant celle-ci
JP2007034279A (ja) * 2005-06-20 2007-02-08 Adeka Corp アルカリ現像性感光性樹脂組成物
JP4684293B2 (ja) * 2005-06-20 2011-05-18 凸版印刷株式会社 着色アルカリ現像型感光性樹脂組成物、及び該着色アルカリ現像型感光性樹脂組成物を用いたカラーフィルタ
US7875407B2 (en) 2005-06-20 2011-01-25 Toppan Printing Co., Ltd. Colored alkali-developable photosensitive resin composition and color filter using the same
JP2007183495A (ja) * 2006-01-10 2007-07-19 Toppan Printing Co Ltd アルカリ現像型感光性樹脂組成物を用いて形成した液晶分割配向制御用突起付き基板、及び液晶表示装置
JP2007206351A (ja) * 2006-02-01 2007-08-16 Adeka Corp アルカリ現像性感光性樹脂組成物
JP4667261B2 (ja) * 2006-02-01 2011-04-06 株式会社Ａｄｅｋａ アルカリ現像性感光性樹脂組成物
JP2007204596A (ja) * 2006-02-01 2007-08-16 Adeka Corp エポキシ樹脂、アルカリ現像性樹脂組成物及びアルカリ現像性感光性樹脂組成物
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TWI367204B (fr) 2012-07-01
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TW200609207A (en) 2006-03-16
CN100386298C (zh) 2008-05-07
CN1771219A (zh) 2006-05-10

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