Phenolic Reactant Contains At Least Two Ring Moieties (includes Fused Or Bridged Ring System) Patents (Class 528/153)
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Patent number: 6207789Abstract: The present invention provides a resin containing in the backbone chain a structural unit represented by the following Formula (I) or (II), as a novel phenolic resin having a high Tg, a low moisture absorption, a low molding shrinkage, high adhesive properties and high flow properties. The present invention also provides a resin composition and a molding material each containing the above resin, and an electronic component device having a device element encapsulated with it.Type: GrantFiled: February 23, 2000Date of Patent: March 27, 2001Assignee: Hitachi Chemical Co., Ltd.Inventors: Haruaki Sue, Shinsuke Hagiwara, Fumio Furusawa, Seiichi Akagi, Kazuyoshi Tendo
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Patent number: 6194491Abstract: An epoxy resin composition comprises (A) a biphenyl epoxy resin, (B) a phenolic resin curing agent having a naphthalene structure, (C) a curing accelerator comprising an addition product of a triphenylphosphine and benzoquinone, and (D) an inorganic filler contained in an amount of 85 to 95% by weight based on the total amount of the composition, and a semiconductor device encapsulated by this resin composition.Type: GrantFiled: October 5, 1998Date of Patent: February 27, 2001Assignee: Hitachi Chemical Company, Ltd.Inventors: Masanobu Fujii, Haruaki Sue, Shinya Yamada
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Patent number: 6159405Abstract: A fire resistant phenolic resole-resorcinol novolac system for a pultrusion process, having a much improved pot life of the two part mixture, lower emissions during processing and a much better surface finish of the pultruded composite when compared to a similar existing system. A method of making a phenolic resole for pultrusion including, but not limited to, the use of modified phenols such as p-phenyl phenol and nonyl phenol.Type: GrantFiled: April 29, 1999Date of Patent: December 12, 2000Assignee: Borden Chemical, Inc.Inventor: John G. Taylor
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Patent number: 6080522Abstract: A radiation sensitive resist composition with high sensitivity, capable of forming a highly heat-resistant resist pattern. The radiation-sensitive resist composition contains, together with a resist material, a polymer which is obtained by reacting (a) a xylylene compound, (b) salicylic acid and (c) 9,9'-bis(hydroxyphenyl)fluorene derivatives or diol compounds of 3,3,3',3'-tetramethyl-2,3,2',3'-tetrahydro-(1,1')-spirobiindene, and which has a weight average molecular weight of 1,000 to 5,000 and Tg of 100 to 150.degree. C. Examples of (c) include 9,9'-bis(4-hydroxyphenyl)fluorene and 3,3,3',3'-tetramethyl-2,3,2',3'-tetrahydro-(1,1')-spirobiindene-6,6'-diol. As the resist material, any of positive- and negative-working resists may be used, with that comprising an alkali-soluble resin and a quinonediazide photo-sensitizer being preferably used.Type: GrantFiled: February 26, 1999Date of Patent: June 27, 2000Assignee: Clariant Internaitonal, Ltd.Inventors: Hiromi Ito, Hatsuyuki Tanaka
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Patent number: 5932389Abstract: This invention relates to alternating and block copolymer resins of uniform and controlled chain length and methods for preparing the same. The alternating copolymer resins are formed from the reaction of a bisoxymethylphenol, a reactive phenolic compound and a monooxymethylphenol. The alternating copolymer may then be further reacted with a second reactive compound in the presence of an aldehyde to form the substantially blocked copolymer. The resins of the invention are characterized by a low molecular weight distribution. The resins are useful for the formulation of high resolution photoresist materials.Type: GrantFiled: February 20, 1998Date of Patent: August 3, 1999Assignee: Shipley Company, L.L.C.Inventor: Anthony Zampini
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Patent number: 5919873Abstract: Disclosed are novel crosslinked polymers derived from methylol phenols and maleic acid species, and methods of synthesizing these macromolecules. Polyesters and chromandicarboxylic groups are the dominant linkages in the structure of general formula: ##STR1## R is H or a spacing group between aromatics, R.sub.1 is an aldehyde substituent, R.sub.2 a spacing group belonging to multihidric alcohols, a maleyl grouping, and n a whole number either 0 or 1.Type: GrantFiled: July 24, 1998Date of Patent: July 6, 1999Assignee: Rio Oeste, S.A.Inventor: Nicholas M. Irving
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Patent number: 5859153Abstract: A composition useful as a powder coating comprises an epoxy resin and a novolak compound or resin having a structure obtained from the reaction of a substituted phenol such as cresol and an aldehyde to form a substituted bis(hydroxymethyl) phenol intermediate which is then reacted with a polyhydroxyphenol containing adjacent hydroxyl groups such as catechol to yield a polyhydroxyphenol-endcapped novolak compound or resin.Type: GrantFiled: June 21, 1996Date of Patent: January 12, 1999Assignee: Minnesota Mining and Manufacturing CompanyInventors: Alan R. Kirk, Allen L. Griggs
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Patent number: 5849808Abstract: A polymer which is insoluble in aqueous-alkaline developer solutions, and comprises structural units of the formula (I): ##STR1## in which R.sub.2 is hydrogen, C.sub.1 -C.sub.18 alkyl, C.sub.5 -C.sub.10 cycloalkyl, C.sub.5 -C.sub.14 aryl, C.sub.6 -C.sub.30 aralkyl, R.sub.3 is C.sub.1 -C.sub.18 alkyl, C.sub.5 -C.sub.10 cycloalkyl, C.sub.5 -C.sub.14 aryl, or C.sub.6 -C.sub.30 aralkyl, it being possible for the alkyl, cycloalkyl, aryl, or aralkyl groups to be substituted if desired by one or more hydroxyl groups or nitro groups or by one or more halogen atoms, and X is a k+1 valent organic radical, k being a number from 1 to 5, and 1 is a number from 0 to 4, in a quantity such that the cleavage products obtained by reaction with an acid are soluble in aqueous-alkaline developer solutions, is suitable as a binder for DUV photoresists of high processing stability, high contrast, and good resolution.Type: GrantFiled: April 19, 1996Date of Patent: December 15, 1998Assignee: Olin Microelectronic Chemicals, Inc.Inventors: Hans-Thomas Schacht, Norbert Muenzel
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Patent number: 5847058Abstract: A process for the production of a storage-stable, modified phenol-aldehyde resol resin includes the use of an alkylresorcinol modifier and preferably a readily-available mixture of alkylresorcinols. A binder system includes the modified phenol-aldehyde resin combined with a curing agent that includes an additional source of an aldehyde, e.g., a phenol-formaldehyde resin. The resin and binder system are useful in the production of a wood composite (such as plywood, oriented strandboard, or fiberboard).Type: GrantFiled: April 5, 1996Date of Patent: December 8, 1998Assignee: Masonite CorporationInventor: Zygmunt Teodorczyk
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Patent number: 5786055Abstract: An adhesive for semiconductor device, comprising (a) a polyamide resin having an amine value of 20 to 60 and a weight average molecular weight of 1,000 to 5,000 and (b) a phenolic compound having a weight average molecular weight of 2,000 or less and having a skeleton containing at least 2 methylol groups.Type: GrantFiled: February 1, 1995Date of Patent: July 28, 1998Assignee: Tomoegawa Paper Co., Ltd.Inventors: Akinori Sei, Yoshikazu Tsukamoto, Takashi Shiozawa, Shouji Aoki, Tadahiro Oishi, Hitoshi Narushima
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Patent number: 5780571Abstract: This invention provides resins and resin compositions which afford cured products with high heat resistance, low water absorption and high adhesion which are useful as electric and electronic materials. Resins obtained by condensation reaction between 4,4'-di(.omega.-substituted methyl)biphenyl or the like and naphthols; epoxy resins obtained by glycidyleterifying said resins; epoxy resin compositions containing these resins; and cured products thereof are disclosed.Type: GrantFiled: June 19, 1997Date of Patent: July 14, 1998Assignee: Nippon Kayaku Kabushiki KaishaInventors: Hiroaki Ohno, Hiromi Morita, Shigeru Moteki, Yasumasa Akatsuka
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Patent number: 5677414Abstract: Cyclic acetal derivative of a resole includes the reaction product of an ortho resole compound with a carbonyl compound or a carbonyl compound derivative. The cyclic acetal derivatives of phenolic resole compounds exhibit enhanced storage stability and can be readily activated at elevated temperatures to prepare phenolic based adhesives and coatings.Type: GrantFiled: April 25, 1996Date of Patent: October 14, 1997Assignee: Lord CorporationInventors: Esther Spaltenstein, Ernest B. Troughton, Jr.
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Patent number: 5663246Abstract: Cyclic acetal derivative of a resole includes the reaction product of an ortho resole compound with a carbonyl compound or a carbonyl compound derivative. The cyclic acetal derivatives of phenolic resole compounds exhibit enhanced storage stability and can be readily activated at elevated temperatures to prepare phenolic based adhesives and coatings.Type: GrantFiled: October 26, 1994Date of Patent: September 2, 1997Assignee: Lord CorporationInventors: Esther Spaltenstein, Ernest B. Troughton, Jr.
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Patent number: 5646219Abstract: A process for the production of a modified phenol-aldehyde resin which may form a binder system when combined with a curing agent which includes an additional source of an aldehyde, e.g., a phenol-formaldehyde resin. The inventive phenol-aldehyde resin may be modified with compounds from one of the following classes: (1) dihydroxybenzenes, (2) aminophenols, and (3) phenylenediamines. The resin and adhesive are useful in the production of a wood composite (such as plywood, oriented strandboard, or fiberboard).Type: GrantFiled: June 7, 1995Date of Patent: July 8, 1997Assignee: Masonite CorporationInventor: Zygmunt Teodorczyk
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Patent number: 5644006Abstract: The present invention provides novel thermoset copolymers, and methods for preparing same, having both the strength and the thermo-oxidative stability required for high performance, high temperature applications. The copolymers comprise (a) a thermoplastic resin having unreacted phenolic OH groups, and (b) bis-oxazoline monomers which have been modified to have at least one substituent on the oxazoline ring selected from the group consisting of a methyl group, a group having at least a substituent capable of undergoing addition polymerization, and a cyclic group capable of undergoing ring opening polymerization.Type: GrantFiled: July 13, 1995Date of Patent: July 1, 1997Assignee: Southwest Research InstituteInventors: Marvin L. Deviney, Joel J. Kampa
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Patent number: 5621052Abstract: Novel aminoplast anchored UV stabilizers are provided. Compared to unanchored stabilizers, the anchored stabilizers disclosed herein have increased compatibility with coating resins and have reduced volatility due to higher molecular weights resulting from anchoring. A process for preparing the anchored stabilizers by the reaction of unanchored stabilizers with alkoxymethylated aminoplasts in a sulfuric acid medium is also provided. The unanchored stabilizers include 2-(2-hydroxyaryl)benzotriazoles, 2-hydroxybenzophenones, 2-(2-hydroxyaryl)-4,6-diaryl-1,3,5-triazines, salicylic acid derivatives, 2-hydroxyoxanilides, and blocked derivatives thereof as well as mixtures of two or more stabilizers. The aminoplasts include alkoxymethylated derivatives of glycolurils, melamines, and benzoguanamines.Type: GrantFiled: December 29, 1992Date of Patent: April 15, 1997Assignee: Cytec Technology Corp.Inventors: Jeno G. Szita, Paul S. Waterman
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Patent number: 5605986Abstract: Novel aminoplast anchored UV stabilizers are provided. Compared to unanchored stabilizers, the anchored stabilizers disclosed herein have increased compatibility with coating resins and have reduced volatility due to higher molecular weights resulting from anchoring. A process for preparing the anchored stabilizers by the reaction of unanchored stabilizers with alkoxymethylated aminoplasts in a sulfuric acid medium is also provided. The unanchored stabilizers include 2-(2-hydroxyaryl)benzotriazoles, 2-hydroxybenzophenones, 2-(2-hydroxyaryl)-4,6-diaryl-1,3,5-triazines, salicylic acid derivatives, 2-hydroxyoxanilides, and blocked derivatives thereof as well as mixtures of two or more stabilizers. The aminoplasts include alkoxymethylated derivatives of glycolurils, melamines, and benzoguanamines.Type: GrantFiled: May 23, 1995Date of Patent: February 25, 1997Assignee: Cytec Technology Corp.Inventors: Jeno G. Szita, Paul S. Waterman
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Patent number: 5591810Abstract: Curable furan resins modified with phenolic resins for use as binders for cements and coating compositions having improved thermal stability, processes for their preparation and their use.Preparation of curable furan resins modified with phenolic resins based on condensation products of alkylidenepolyphenols of the novolak type with furfuryl alcohol or mixtures thereof with other reactive furan derivatives, furthermore curable solutions thereof in reactive organic solvents, processes for their preparation and their use as binders having improved thermal stability for preparing self-curing, chemically resistant and high-temperature-resistant cements and coating compositions.Type: GrantFiled: April 11, 1995Date of Patent: January 7, 1997Assignee: Hoechst AktiengesselschaftInventors: Wolfgang Hesse, Klaus Rauhut
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Patent number: 5571886Abstract: An essentially aromatic alkali soluble novolak resin comprising the product resulting from the acid condensation of an aromatic aldehyde and a phenol where the resin has a molecular weight in excess of 1500 and a glass transition temperature in excess of 125.degree. C. If desired, the aromatic novolak resin may be blended with a conventional novolak resin to regulate the glass transition temperature of the resin. The aromatic novolak resin and blends formed therefrom are especially suitable as coating resins and are useful for the formation of photoresist coating compositions.Type: GrantFiled: March 21, 1994Date of Patent: November 5, 1996Assignee: Shipley Company, Inc.Inventor: Anthony Zampini
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Patent number: 5560968Abstract: A process for encapsulating a semiconductor device involves the step(s) of encapsulating the device with an epoxy resin composites represented by the formula (2) ##STR1## in which R.sub.1 to R.sub.4 independently represent hydrogen, an alkyl or cycloalkyl group having 1 to 9 carbon atoms, or halogen, and X represents hydrogen, an alkyl group having 1 to 9 carbon atoms, or an aryl and n represents an average number of repeating units of 0.1 to 1.6; and a curing agent.Type: GrantFiled: June 5, 1995Date of Patent: October 1, 1996Assignee: Sumitomo Chemical Company, LimitedInventors: Noriaki Saito, Takashi Morimoto, Kazuo Takebe, Yutaka Shiomi, Shigeki Naitoh, Shuichi Kanagawa
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Patent number: 5552509Abstract: A phenolic resin composition herein disclosed comprises, as essential components, (i) at least one phenol resin A selected from the group consisting of residues formed through purification of bisphenol A, residues obtained by cleaving the bisphenol A-purification residue, condensates of the bisphenol A-purification residue obtained by reacting the bisphenol A-purification residue with formaldehyde and condensates of the cleavage residue obtained by reacting the cleavage residue with formaldehyde, and (ii) at least one phenolic resin B selected from the group consisting of high-boiling fraction obtained through production of bisphenol F and condensates of the high-boiling fraction obtained by reacting the high-boiling fraction with formaldehyde.Type: GrantFiled: August 31, 1993Date of Patent: September 3, 1996Assignee: Mitsui Toatsu Chemicals, Inc.Inventors: Tomoko Takashima, Shigeru Iimuro, Takashi Kitamura
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Patent number: 5512641Abstract: What is disclosed an aromatic oligoimine having a recurring unit composed of an aromatic dialdehyde having a phenolic hydroxyl group and an aromatic diamine and a number-average degree of polymerization of 2 to 20 and a process for preparing the same, and an aromatic polyimine made by thermally dehydrating the aromatic oligoimine and a process for preparing the same.Type: GrantFiled: March 24, 1995Date of Patent: April 30, 1996Assignee: Arakawa Kagaku Kogyo Kabushiki KaishaInventor: Yoichiro Ezaki
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Patent number: 5510446Abstract: A naphthol-modified phenolic resin having low softening point and good flowability is obtained by allowing a naphthol and a phenol to react with an aldehyde in the presence of an acid catalyst at 60 to 110.degree. C. to obtain a primary reaction mixture, heating the primary reaction mixture in the presence of a strong acid, a super acid or a mixture thereof under ambient pressure at 120 to 180.degree. C. for 1 to 12 hours to obtain a secondary reaction mixture, and subjecting the secondary reaction mixture to vacuum concentration or steam distillation, and the naphthol-modified phenolic resin is suited to use as a curing agent in epoxy resin molding materials for sealing electronic parts.Type: GrantFiled: June 2, 1995Date of Patent: April 23, 1996Assignee: Hitachi Chemical Company, Ltd.Inventors: Haruaki Sue, Shinsuke Hagiwara, Hiroyuki Saitoh
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Patent number: 5508361Abstract: The polymer scale preventive agent comprises an alkaline solution containing (A) an condensation product of (A-1) a hydroxybiphenyl compound with (A-2) an aldehyde compound, (B) a reaction stopper, and (C) an inorganic colloid and is used for polymerization of a monomer having an ethylenically unsaturated double bond. The process of producing the polymer comprises polymerizing the monomer in a polymerization vessel having a coating film on its inner wall surfaces, whereby polymer scale is prevented from being deposited, wherein said coating film is formed by applying, on said inner wall surfaces, said alkaline solution, followed by drying. According to the invention, deposition of polymer scale can be effectively prevented not only on the areas in the liquid phase but also at and in the vicinity of the interface between the gas and liquid phases in a polymerization vessel.Type: GrantFiled: April 19, 1995Date of Patent: April 16, 1996Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Toshihide Shimizu, Mikio Watanabe
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Positive photoresist composition comprising a novolak resin having a cycloalkylidene-bisphenol group
Patent number: 5494773Abstract: A positive photoresist composition comprising an alkali-soluble novolak resin and a 1,2-quinonediazide compound is described, wherein the alkali-soluble novolak resin contains a novolak resin to be obtained by condensing a mixture of (a) at least one phenol represented by the following formula (1) and at least one compound represented by the following formula (2) and (b) at least one aldehyde: ##STR1## wherein R.sub.1, R.sub.2 and R.sub.3 are the same or different and each represents a hydrogen atom, a hydroxyl group, a halogen atom, an alkyl group, an alkoxy group, an alkenyl group, an aryl group, an aralkyl group, an alkoxycarbonyl group or an arylcarbonyl group; R.sub.4, R.sub.5, R.sub.6 and R.sub.7 are the same or different and each represents a hydrogen atom, a hydroxyl group, a halogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, an alkenyl group, an aryl group or an aralkyl group; and n represents an integer of from 4 to 7.Type: GrantFiled: March 6, 1995Date of Patent: February 27, 1996Assignee: Fuji Photo Film Co., Ltd.Inventors: Shiro Tan, Yasumasa Kawabe, Tadayoshi Kokubo -
Patent number: 5486580Abstract: The present invention discloses novolacs and thermosets thereof containing mesogenic moieties. Certain of said novolacs and thermosets thereof exhibit nonlinear optical properties upon orientation.Type: GrantFiled: November 2, 1994Date of Patent: January 23, 1996Assignee: The Dow Chemical CompanyInventors: Mark D. Newsham, Jimmy D. Earls, Robert E. Hefner, Jr.
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Patent number: 5478908Abstract: Resols which are suitable for use as binders for cements, laminates, impregnations and abrasives having low after-shrinkage have a free phenol content of less than 5% by weight and are in the form of mixed condensates of trifunctional phenols with respect to formaldehyde and alkylidenepolyphenols in a molar ratio of phenolic hydroxyl groups in the trifunctional phenols to hydroxyl groups in the alkylidenepolyphenols of 9:1 to 3:7 with formaldehyde in a molar ratio of the sum of phenolic hydroxyl groups to formaldehyde of 1:1.2 to 1:2.0.Type: GrantFiled: November 14, 1994Date of Patent: December 26, 1995Assignee: Hoechst AktiengesellschaftInventors: Wolfgang Hesse, Klaus Rauhut
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Patent number: 5468590Abstract: A positive resist composition containing a quinone diazide compound and an alkali-soluble resin which contains a resin (A) obtained by a condensation reaction of an aldehyde compound, at least one phenol compound of the formula: ##STR1## wherein R.sub.1, R.sub.2 and R.sub.3 are independently a hydrogen atom, or a C.sub.1 -C.sub.4 alkyl or alkoxy group, and j is 1 or 2, and at least one compound of the formula: ##STR2## wherein R'.sub.1, R'.sub.2, R'.sub.3, R'.sub.4, R'.sub.5 and R'.sub.6 are independently a hydrogen atom, or a C.sub.1 -C.sub.4 alkyl or alkoxy group, R'.sub.7 is a hydrogen, a C.sub.1 -C.sub.4 alkyl group or an aryl group, and k, m and n are independently 0, 1 or 2 provided that a sum of k, m and n is larger than 2, which composition is excellent in balance among various properties such as a profile, a sensitivity, heat resistance and a depth of focus.Type: GrantFiled: November 29, 1994Date of Patent: November 21, 1995Assignee: Sumitomo Chemical Company, LimitedInventors: Kazuhiko Hashimoto, Haruyoshi Osaki, Chinehito Ebina, Kyoko Nagase, Hiroshi Moriuma, Yasunori Uetani
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Patent number: 5462997Abstract: An epoxy resin composition contains (a) an epoxy resin represented by the general formula (2) ##STR1## wherein R.sub.1 to R.sub.4 independently represent hydrogen, an alkyl or cycloalkyl group having 1 to 9 carbon atoms, or halogen, and X represents hydrogen, an alkyl group having 1 to 9 carbon atoms, or an aryl and n represents an average number of repeating units of 0.1 to 1.6; and a curing agent.Type: GrantFiled: October 27, 1994Date of Patent: October 31, 1995Assignee: Sumitomo Chemical Co., Ltd.Inventors: Noriaki Saito, Takashi Morimoto, Kazuo Takebe, Yutaka Shiomi, Shigeki Naitoh, Shuichi Kanagawa
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Patent number: 5459223Abstract: A naphthol-modified phenolic resin having low softening point and good flowability is obtained by allowing a naphthol and a phenol to react with an aldehyde in the presence of an acid catalyst at 60.degree. to 110.degree. C. to obtain a primary reaction mixture, heating the primary reaction mixture in the presence of a strong acid, a super acid or a mixture thereof under ambient pressure at 120.degree. to 180.degree. C. for 1 to 12 hours to obtain a secondary reaction mixture, and subjecting the secondary reaction mixture to vacuum concentration or steam distillation, and the naphthol-modified phenolic resin is suited to use as a curing agent in epoxy resin molding materials for sealing electronic parts.Type: GrantFiled: February 8, 1994Date of Patent: October 17, 1995Assignee: Hitachi Chemical CompanyInventors: Haruaki Sue, Shinsuke Hagiwara, Hiroyuki Saitoh
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Patent number: 5451484Abstract: A positive resist composition comprising a quinonediazide compound and an alkali-soluble resin containing resin (A) obtainable through a condensation reaction of at least one compound represented by the general formula (I): ##STR1## wherein R.sub.1, R.sub.2 and R.sub.3 independently of one another each represent a hydrogen atom or an alkyl or alkoxy group having 1-4 carbon atoms and k represents 1 or 2, at least one polyphenol compound represented by the general formula (II): ##STR2## wherein R.sub.4 ' to R.sub.6 ' each represent a hydrogen atom or an alkyl or alkoxy group and n represents 1 or 2, with an aldehyde compound. This positive resist composition is excellent in properties such as profile, resolution, heat resistance, etc.Type: GrantFiled: May 27, 1993Date of Patent: September 19, 1995Assignee: Sumitomo Chemical Company, Ltd.Inventors: Kyoko Nagase, Haruyoshi Osaki, Hiroshi Moriuma
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Patent number: 5429904Abstract: A positive resist composition comprising a quinonediazide compound and an alkali-soluble resin containing resin (A) obtainable through a condensation reaction of at least one compound represented by the general formula (I): ##STR1## wherein R.sub.1, R.sub.2 and R.sub.3 independently of one another each represent a hydrogen atom or an alkyl or alkoxy group having 1-4 carbon atoms and k represents 1 or 2, at least one polyphenol compound represented by the general formula ( II ): ##STR2## wherein R.sub.4 ' to R.sub.6 ' each represent a hydrogen atom or an alkyl or alkoxy group and n represents 1 or 2, with an aldehyde compound. This positive resist composition is excellent in properties such as profile, resolution, heat resistance, etc.Type: GrantFiled: May 27, 1993Date of Patent: July 4, 1995Assignee: Sumitomo Chemical Company, Ltd.Inventors: Kyoko Nagase, Haruyoshi Osaki, Kazuhiko Hashimoto, Hiroshi Moriuma
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Patent number: 5395912Abstract: There is provided an epoxy resin composition represented by the general formula: ##STR1## wherein R.sub.1 represents an alkyl or cycloalkyl group having 1 to 9 carbon atoms, or halogen, R.sub.2 to R.sub.4 independently represent hydrogen, an alkyl or cycloalkyl group having 1 to 9 carbon atoms, or halogen, and X represents hydrogen, an alkyl group having 1 to 9 carbon atoms, or an aryl group, and n represents an average number of repeating units of 0.1 to 1.6. Cured products prepared from the epoxy resin have a lower hygroscopicity and a balance between thermal resistance and curing performance.Type: GrantFiled: November 22, 1993Date of Patent: March 7, 1995Assignee: Sumitomo Chemical Company, LimitedInventors: Noriaki Saito, Takashi Morimoto, Kazuo Takebe, Yutaka Shiomi, Shigeki Naitoh, Shuichi Kanagawa
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Patent number: 5395727Abstract: A novolak resin made from a carbonyl compound and a specific phenol compound, which resin has good properties, in particular, as a base resin of a photoresist.Type: GrantFiled: November 29, 1993Date of Patent: March 7, 1995Assignee: Sumitomo Chemical Company, LimitedInventors: Yasunori Uetani, Haruyoshi Osaki, Naoki Takeyama, Yuji Ueda, Hiromi Ueki, Takehiro Kusumoto
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Patent number: 5350827Abstract: A novolak resin composition comprising at least one unit of the reaction product of a para-, para-bonded bisphenol having formula (A): ##STR1## wherein R.sub.1 =hydrogen, lower alkyl group having 1-4 carbon atoms, halogen, or lower alkoxy group having 1-4 carbon atoms;wherein R.sub.2 =hydrogen or lower alkyl group having 1-4 carbon atoms; andwherein X is selected from the group consisting of: CH.sub.2, CH(CH.sub.3), C(CH.sub.3).sub.2, O, and S;with a bismethylol monomer selected from a difunctional ortho-, ortho-phenolic bismethylol of Formula (B), a difunctional ortho-, para-phenolic bismethylol of Formula (C): ##STR2## wherein R.sub.3 is selected from CH.sub.3, CH.sub.2 CH.sub.3, Cl, and Br; andwherein R.sub.4 is selected from H and CH.sub.3.Type: GrantFiled: February 9, 1994Date of Patent: September 27, 1994Assignee: OCG Microelectronic Materials, Inc.Inventors: Thomas R. Sarubbi, Joseph J. Sizensky
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Patent number: 5349038Abstract: Oligomeric condensation products including repeat units of the formula: ##STR1## wherein M.sup.+ is a monovalent metal cation; and wherein a=1 or 2 and R is C(R.sub.f).sub.3, or wherein a=O, 1 or 2 and R is ##STR2## wherein each R.sub.f group is independently selected from the group consisting of Fluorine (F) or a perfluoroalkyl group;and b=0, 1 or 2; anda+b=0, 1 or 2; with the proviso thata+b=1 or 2 for at least about half ofsaid repeat units.The products are useful as stainblockers in nylon carpets.Type: GrantFiled: October 15, 1993Date of Patent: September 20, 1994Assignee: Monsanto CompanyInventors: Le Moyne W. Plischke, Rupert J. Snooks, Jr.
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Patent number: 5346799Abstract: An alkali-soluble novolak binder resin made by the condensation reaction of a mixture of phenolic monomers with at least one aldehyde source, said phenolic monomers consisting of:(1) about 2-18% by weight of said mixture being 2,6-dimethylphenol;(2) about 55-75% by weight of said mixture being 2,3-dimethylphenol;(3) about 16-40% by weight of said mixture being a para-substituted lower alkyl phenol selected from the group consisting of 3,4-dimethylphenol, para-cresol, and para-cresol dimer;and the amount of said aldehyde source being at least a stoichiometric amount to react with all of said phenolic moieties. These novolak binder resins may be used in radiation-sensitive compositions useful as positive-working photoresists.Type: GrantFiled: December 7, 1992Date of Patent: September 13, 1994Assignee: OCG Microelectronic Materials, Inc.Inventors: Alfred T. Jeffries, III, David J. Brzozowy
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Patent number: 5334674Abstract: Copolycondensation of a hydroxyl group-containing naphthalene and xylene with an aldehyde compound gives a polyhydroxy aromatic compound. The hydroxyl group-containing naphthalene comprises at least one of naphthols and dihydroxynaphthalenes. In the polyhydroxy aromatic compound, the proportions of the naphthalene unit and xylene unit are 95 to 50:5 to 50 (mole percent), and each molecule contains 2 to 20 naphthalene units. The polyhydroxy aromatic compound is useful as an epoxy resin curing agent. Reaction of the polyhydroxy aromatic compound with an epihalohydrin gives an epoxy resin. An epoxy resin composition can be prepared from the epoxy resin and a curing agent.Type: GrantFiled: June 18, 1992Date of Patent: August 2, 1994Assignees: Dai-Ichi Kogyo Seiyaku Co., Ltd., Nitto Denko CorporationInventors: Akihiro Naka, Shuichi Ito, Shinya Akizuki, Kiyoshi Saito
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Patent number: 5334692Abstract: New, highly branched polyphosphonates which have a greatly improved flame retardant action compared with known polyphosphonates which are suitable as additives for plastics. In addition the new polyphosphonates may be incorporated in plastics as stabilizers with excellent migration properties.Type: GrantFiled: November 24, 1993Date of Patent: August 2, 1994Assignee: Bayer AktiengesellschaftInventors: Bernhard Hess, Wolfgang Schulz-Schlitte, Jurgen Kirsch, Dieter Freitag, Uwe Arndt, Hans-Georg Gehrke, Klaus Zander
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Patent number: 5326665Abstract: A positive type resist composition comprising an alkali-soluble resin and a quinonediazide compound, wherein the alkali-soluble resin containing resin (A) is obtainable through a condensation reaction with at least one phenol compound represented by the following general formula (I): ##STR1## wherein R.sub.1 to R.sub.3 independently of one another each represent a hydrogen atom or an alkyl or alkoxy group having 1-4 carbon atoms and k represents 1 or 2, at least one compound represented by the following general formula (II): ##STR2## wherein R.sub.4 represents a hydrogen atom, an alkyl group having 1-4 carbon atoms or a phenyl group, R.sub.5 to R.sub.7 independently of one another each represent a hydrogen atom or an alkyl or alkoxy group having 1-4 carbon atoms and n represents 1 or 2, and an aldehyde compound. This composition is excellent in the balance between performances such as sensitivity, heat resistance and profile, and is free from scum.Type: GrantFiled: March 1, 1993Date of Patent: July 5, 1994Assignee: Sumitomo Chemical Company, LimitedInventors: Haruyoshi Osaki, Hiroshi Moriuma, Yasunori Uetani
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Patent number: 5306748Abstract: Fluorine-modified thermosetting reins are available as phenolic or epoxy resins having trifluoromethyl groups and a naphthalene skeleton in a molecule. They are useful as components of resin compositions or resin modifiers and cure to products having low water pickup, low coefficient of thermal expansion, and adhesion as well as heat resistance and mechanical strength. Thermosetting resin compositions having such a thermosetting resin blended therein are useful in semiconductor element packaging.Type: GrantFiled: July 29, 1992Date of Patent: April 26, 1994Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Toshio Shiobara, Hisashi Shimizu, Manabu Narumi
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Patent number: 5304456Abstract: A negative photoresist composition containing an alkali-soluble resin which is obtainable through a condensation reaction of an aldehyde with a phenol compound containing a compound of the general formula: ##STR1## wherein R.sup.1 to R.sup.9 are independently a hydrogen atom, an alkyl group, an alkenyl group, an alkylcarbonyl group, a halogen atom or a hydroxyl group, provided that at least one of R.sup.1 to R.sup.9 is a hydroxyl group and, at the ortho- or para-position to the hydroxyl group, at least two hydrogen atoms are present; a cross linking agent; and a photo-acid generator, and a negative photoresist composition comprising an alkali-soluble resin, a cross linking agent and a photo-acid generator having a trifluoromethanesulfonic acid ester group, which can increase resolution and contrast of a photoresist pattern.Type: GrantFiled: January 29, 1992Date of Patent: April 19, 1994Assignee: Sumitomo Chemical Company, LimitedInventors: Yuji Ueda, Hiromi Ueki, Naoki Takeyama, Takehiro Kusumoto
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Patent number: 5302673Abstract: Copolycondensation of .alpha.-naphthol and .beta.-naphthol with an aldehyde compound gives a poly-hydroxynaphthalene compound having an average molecular weight of 300 to 2,000. This compound is useful as a curing agent for epoxy resins and as a precursor of epoxy resins. Epoxy resin compositions include (1) compositions comprising an epoxy resin and the poly-hydroxynaphthalene compound as a curing agent and (2) compositions comprising an epoxy resin obtained by reacting the poly-hydroxynaphthalene compound with an epihalohydrin and a curing agent. The epoxy resin compositions of the invention are characterized in that the cured resins have a high glass transition temperature and high heat stability and high moisture resistance, scarcely allowing package cracking even in soldering treatment. Therefore the compositions are suited for use in encapsulating semiconductors.Type: GrantFiled: June 18, 1992Date of Patent: April 12, 1994Assignees: Dai-Ichi Kogyo Seiyaku Co., Ltd., Nitto Denko CorporationInventors: Akihiro Naka, Shuichi Ito, Shinya Akizuki, Kiyoshi Saito
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Patent number: 5302687Abstract: A process for preparing a polymeric composition comprising reacting a mixture of at least one phenolic compound and at least one oxazoline compound in the presence of a catalytic amount of at least one ammonium salt and a tetracarbyl phosphonium salt, and optionally also in the presence of an alkyl halide is described.Type: GrantFiled: March 29, 1993Date of Patent: April 12, 1994Assignee: Ashland Oil, Inc.Inventors: Billy M. Culbertson, Omar Tiba, Gilbert M. Gynn
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Patent number: 5268444Abstract: Phenylethynyl-terminated poly(arylene ethers) are prepared in a wide range of molecular weights by adjusting monomer ratio and adding an appropriate amount of 4-fluoro-4'-phenylethynylbenzophenone during polymer synthesis. The resulting phenylethynyl-terminated poly(arylene ethers) react and crosslink upon curing for one hour at 350.degree. C. to provide materials with improved solvent resistance, higher modulus and better high temperature properties than the linear, uncrosslinked polymers.Type: GrantFiled: April 2, 1993Date of Patent: December 7, 1993Assignee: The United States of America as represented by the Administrator of the National Aeronautics and Space AdministrationInventors: Brian J. Jensen, Robert G. Bryant, Paul M. Hergenrother
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Patent number: 5254664Abstract: A reaction of the compound (A) having at least two 2-oxazoline groups with the compound (B) having at least two functional groups of one or a plural kind selected from the group consisting of an aromatic hydroxyl group, an amino group and a thiol group proceeds in a short period of time to produce a cured resin with superior mechanical strength, heat resistance and adhesion properties.Type: GrantFiled: December 31, 1991Date of Patent: October 19, 1993Assignee: Nippon Shokubai Co., Ltd.Inventors: Subhash C. Narang, Asutosh Nigam, Apparao Satyam, Susanna C. Ventura, Yoshihiro Arita
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Patent number: 5254440Abstract: A methylol-substituted trihydroxybenzophenone of the formula (I): ##STR1## This methylol-substituted trihydroxybenzophenone may be reacted with selected phenolic monomers during or after the formation of a phenolic novolak resin thereby said resin having at least one unit of formula (II): ##STR2## wherein R and R.sub.1 are individually selected from hydrogen, a lower alkyl group having 1 to 4 carbon atoms or a lower alkoxy group having 1 to 4 carbon atoms.Type: GrantFiled: September 30, 1992Date of Patent: October 19, 1993Assignee: OCG Microelectronic Materials, Inc.Inventor: Medhat A. Toukhy
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Patent number: 5250653Abstract: A phenolic novolak resin composition comprising a condensation product of at least one aldehyde source with a phenolic source comprising 5-indanol. Said phenolic novolak resins are used in radiation-sensitive compositions, especially those useful as positive-working photoresists.Type: GrantFiled: February 22, 1993Date of Patent: October 5, 1993Assignee: OCG Microelectronic Materials, Inc.Inventor: Medhat A. Toukhy
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Patent number: 5237037Abstract: A radiation-sensitive composition dissolved in a solvent comprising:(A) a photoactive compound;(B) an alkali-soluble novolak binder resin made by the condensation reaction of a mixture of phenolic monomers and phenolic dimers with an aldehyde source, said mixture of phenolic monomers and phenolic dimers comprising:(1) 2-25% by weight of said mixture being at least one monofunctional phenolic monomer;(2) about 98-75% by weight of said mixture comprising a mixture of difunctional phenolic monomers or dimers comprising:(a) about 0.Type: GrantFiled: June 12, 1991Date of Patent: August 17, 1993Assignee: OCG Microelectronic Materials, Inc.Inventor: Charles E. Ebersole
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Patent number: 5235022Abstract: A block copolymer novolak resin composition comprising at least one unit of the reaction product of an alkali-soluble phenolic polymer and a reactive ortho, ortho bonded oligomer having the formula: ##STR1## wherein x is from 2 to 7; wherein R is selected from hydrogen a lower alkyl group or lower alkoxy group having 1-4 carbon atoms and a halogen group; and Y.sub.1 is either a hydroxyl group; an alkoxy group or a halogen group; and Y.sub.2 is hydrogen, alkyl, alkoxy, halogen, hydroxyl, --CH.sub.2 OH, --CH.sub.2 -- halogen, or --CH.sub.2 -alkoxy group.Type: GrantFiled: November 23, 1992Date of Patent: August 10, 1993Assignee: OCG Microelectronic Materials, Inc.Inventors: Alfred T. Jeffries, III, Kenji Honda, Andrew J. Blakeney, Sobhy Tadros