Two Distinct Phenolic Reactants Or Two Or More Hydroxy Groups Or Phenate Groups Bonded To Nuclear Carbon Atoms Of The Same Benzene Ring Patents (Class 528/155)
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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: 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: 5763558Abstract: A process for hardening a composition and a hardenable composition, in wh there are used:at least one novolac resin;at least one hardener of the resin, selected from the group consisting of substituted melamines;at least one compound comprising at least one ##STR1## group, this compound being without methylol group and ether group corresponding to methylol, and/or at least one reagent capable of giving such a compound under the conditions of the hardening.The hardening of the resin is caused by the action of heat.Type: GrantFiled: June 11, 1996Date of Patent: June 9, 1998Assignee: Compagnie Generale Des Etablissements Michelin-Michelin & CieInventors: Brigitte Marie Chauvin, Olivier Durel
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Patent number: 5756599Abstract: A process for producing a phenol-aldehyde (e.g., cresol-aldehyde) resin that is modified with a dihydroxybenzene compound. The resin may form a binder system when combined with a curing agent which includes an additional source of an aldehyde. The resin and adhesive are useful in the production of wood composite articles by a steam injection process.Type: GrantFiled: July 7, 1997Date of Patent: May 26, 1998Assignee: Masonite CorporationInventor: Zygmunt Teodorczyk
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Patent number: 5726257Abstract: An aryl ester compound composed of a polyhydric phenol in which at least one OH group has been esterified with an organic acid or its derivatives having 1 to 20 carbon atoms, said polyhydric phenol being the condensation product of a phenolic compound represented by the general formula: ##STR1## with a carbonyl compound represented by the general formula: ##STR2## which aryl ester compound can give, when used as a curing agent for an epoxy resin, a cured product having a low dielectric constant and a low dielectric loss tangent; an epoxy resin composition comprising as the essential components an epoxy resin, said aryl ester compound and a cure accelerator; and a copper-clad laminate using the epoxy resin composition. The copper-clad laminate has a low dielectric constant and a low dielectric loss tangent and is excellent in adhesiveness as compared with conventional ones, and hence, is suitable for multilayer printed wiring board for high speed operation, especially at high-frequency region.Type: GrantFiled: August 28, 1995Date of Patent: March 10, 1998Assignee: Sumitomo Chemical Company, Ltd.Inventors: Youichi Ueda, Yasuhiro Endo, Mitsuhiro Shibata, Kaori Yamasaki
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Patent number: 5688893Abstract: The present invention provides methods for producing water insoluble, aqueous alkali soluble novolak resins having a precise and consistent molecular weight, by adjusting the concentration of Lewis base. A method is also provided for producing photoresist composition from such novolak resins and for producing semiconductor devices using such photoresist compositions.Type: GrantFiled: December 20, 1996Date of Patent: November 18, 1997Assignee: Hoechst Celanese CorporationInventors: M. Dalil Rahman, Daniel P. Aubin, Dana L. Durham, Ralph R. Dammel
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Patent number: 5684114Abstract: A two-part adhesive is provided wherein the first part comprises a stable aqueous alkaline monohydroxylic phenolic resole resin solution containing a methylene donor such as oxazolidine or a methylolurea and the second part comprises a stable resorcinolic resin precondensate having a shortage of formaldehyde and optionally containing a catalyst such as an ester functional compound for the resole resin. The resin in each part exhibits viscosity stability of an unmodified resin until mixed with the other part wherein the methylene donor, of the first part catalyzes the resorcinolic resin of the second part and the catalyst, when used, of the second part catalyzes the monohydroxylic phenolic resole resin of the first part. The adhesive finds utility in the production of structural lignocellulosic panels.Type: GrantFiled: June 7, 1995Date of Patent: November 4, 1997Assignee: Borden Chemical, Inc.Inventors: Earl K. Phillips, William D. Detlefsen, Fred E. Carlson
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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: 5674657Abstract: The invention is directed to an alkali-soluble novolak binder resin composition made by addition condensation reaction of a phenolic mixture with at least one aldehyde source, the feedstock of said phenolic mixture for the reaction comprising about 33 to about 83 mole percent of meta-cresol; about 1 to about 4 mole percent of para-cresol; about 10 to about 60 mole percent of a phenolic monomer selected from the group consisting of 2,3-xylenol, 3,4-xylenol, 3,5-xylenol and mixtures thereof; and about 5 to about 55 mole percent of a methoxy phenol monomer, the amount of aldehyde source being from about 40 to about 200 percent of the stoichiometric amount needed to react with all of the phenolic moieties in said phenolic mixture, and the alkali-soluble novolak binder resin having a weight average molecular weight (M.sub.w) of about 3,000 to about 20,000 with a molecular weight polydispersity (M.sub.w /M.sub.n) of 1.5-4.0. The invention is also directed to a positive working photoresist made from the composition.Type: GrantFiled: November 4, 1996Date of Patent: October 7, 1997Assignees: Olin Microelectronic Chemicals, Inc., Fuji Photo Film Co., Ltd.,Inventors: Shiro Tan, Yasumasa Kawabe, Kenji Honda
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Patent number: 5652081Abstract: Provided is a positive working photoresist composition which comprises an alkali-soluble resin and a 1,2-quinonediazide compound, with the resin being a novolak resin obtained by the condensation reaction of monomers comprising specified phenol compounds with formaldehyde.Type: GrantFiled: September 5, 1996Date of Patent: July 29, 1997Assignee: Fuji Photo Film Co., Ltd.Inventors: Shiro Tan, Shinji Sakaguchi, Yasumasa Kawabe
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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: 5639806Abstract: Proppants comprising a particle coated with a composition comprising bisphenol-aldehyde novolak resin, a bisphenol homopolymer or mixtures including such polymers are disclosed. Foundry sands comprising a particle coated with a composition comprising bisphenol-aldehyde novolak resin, a bisphenol homopolymer or mixtures including such polymers are disclosed. Methods of making and using these proppant particles in subterranean formations or making and using these foundry sands in foundries are also disclosed.Type: GrantFiled: March 28, 1995Date of Patent: June 17, 1997Assignee: Borden Chemical, Inc.Inventors: Calvin K. Johnson, Kwok-tuen Tse
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Patent number: 5637658Abstract: 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) arninophenols, 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: May 23, 1995Date of Patent: June 10, 1997Assignee: Masonite CorporationInventor: Zygmunt Teodorczyk
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Patent number: 5629083Abstract: A process for the production of modified phenol-aldehyde resins includes the use of a modifier selected from melamine, urea, and other suitable nonvolatile organic compounds. The phenolic component of the resins preferably includes a difunctional phenolic compound. The inventive resins resist precuring and are particularly useful in blowline blending procedures.Type: GrantFiled: June 7, 1995Date of Patent: May 13, 1997Assignee: Masonite CorporationInventor: Zygmunt Teodorczyk
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Patent number: 5578685Abstract: Curing components containing amino groups for curing epoxy resins are obtained by the reaction of alkylated polyhydroxy aromatics (A) with polyamines (B) and aldehydes (C) by the mechanism of the Mannich reaction. The preparation of curable mixtures and varnish formulations is also disclosed. The curing components and curable mixtures can also be employed at a low temperature.Type: GrantFiled: June 2, 1995Date of Patent: November 26, 1996Assignee: Hoechst AktiengesellschaftInventors: Uwe Neumann, Claus Godau
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Patent number: 5576108Abstract: Curing components containing amino groups for curing epoxy resins are obtained by the reaction of alkylated polyhydroxy aromatics (A) with polyamines (B) and aldehydes (C) by the mechanism of the Mannich reaction. The preparation of curable mixtures and varnish formulations is also disclosed. The curing components and curable mixtures can also be employed at a low temperature.Type: GrantFiled: September 9, 1994Date of Patent: November 19, 1996Assignee: Hoechst AktiengesellschaftInventors: Uwe Neumann, Claus Godau
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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: 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: 5521259Abstract: A process for producing a highly reactive modified phenolic resin, comprising the steps of polycondensing a petroleum heavy oil or pitch, a formaldehyde polymer and a phenol in the presence of an acid catalyst to thereby prepare a modified phenolic resin; and reacting the resultant modified phenolic resin with a phenol in the presence of an acid catalyst but in the absence of a crosslinking agent such as a formaldehyde polymer to thereby lower the molecular weight of the modified phenolic resin. This highly reactive modified phenolic resin has a low number average molecular weight and a high phenol content, so that its resin melt viscosity is low and that it exhibits a markedly improved reactivity with an epoxy resin.Type: GrantFiled: January 24, 1995Date of Patent: May 28, 1996Assignee: Kashima Oil Co., Ltd.Inventors: Masahiro Tsumura, Masao Tashima, Hiromi Miyasita
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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: 5494785Abstract: A phenolic novolak composition prepared by a process comprising the steps of:(1) reacting a first phenolic monomer comprising a major portion of at least one trifunctional phenolic monomer with a first aldehyde source in the absence of a catalyst at a reaction temperature from about 100.degree. C. to about 200.degree. C. and at a reaction pressure of about 2 to about 15 atmospheres to form a phenolic oligomer having a weight average molecular weight from about 500 to about 2,000, having ortho-ortho bonding of about 55% to about 75% of the methylene bonds between the phenolic moieties; and having a time to clear of less than 125 seconds per micron; wherein the mole ratio of said first aldehyde source to said first phenolic monomer is from about 0.3:1.0 to about 0.55:1.0; and(2) then reacting said oligomer with an optional second phenolic source and a second aldehyde source at a temperature from about 80.degree. C. to about 150.degree. C.Type: GrantFiled: January 17, 1995Date of Patent: February 27, 1996Assignee: OCG Microelectronic Materials, Inc.Inventors: Joseph J. Sizensky, Thomas R. Sarubbi, Medhat A. Toukhy
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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: 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: 5473045Abstract: A phenolic novolak composition prepared by a process comprising the steps of:(1) reacting a first phenolic monomer comprising a major portion of at least one trifunctional phenolic monomer with a first aldehyde source in the absence of a catalyst at a reaction temperature from about 100.degree. C. to about 200.degree. C. and at a reaction pressure of about 2 to about 15 atmospheres to form a phenolic oligomer having a weight average molecular weight from about 500 to about 2,000, having ortho--ortho bonding of about 55% to about 75% of the methylene bonds between the phenolic moieties; and having a time to clear of less than 125 seconds per micron; wherein the mole ratio of said first aldehyde source to said first phenolic monomer is from about 0.3:1.0 to about 0.55:1.0; and(2) then reacting said oligomer with an optional second phenolic source and a second aldehyde source at a temperature from about 80.degree. C. to about 150.degree. C.Type: GrantFiled: January 17, 1995Date of Patent: December 5, 1995Assignee: OCG Microelectronic Materials, Inc.Inventors: Joseph J. Sizensky, Thomas R. Sarubbi, Medhat A. Toukhy
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Patent number: 5470924Abstract: A process for forming a phenol formaldehyde resin including the steps of: (i) forming a first additive including a glycol and an aromatic dicaborxylic acid; (ii) adding said first additive as well as an alpha hydroxy acid to a first resin component comprising resin precursors including phenol, formaldehyde, an acid catalyst or a base catalyst after said precursors have reacted for 40-55 minutes and/or when water has separated from said precursors; (iii) isolating or storing said first resin component which is maintained in a non cured state by the addition of said first additive; (iv) forming a second additive including zinc chloride, an alpha hydroxy acid, para toluene sulphonic acid, sulphuric or hydrochloric acid and a non aqueous solvent; (v) adding said second additive to a second resin component which includes resin precursors phenol, formaldehyde, methanol and an aliphatic dicarboxylic acid after said precursors have reacted for 20-30 minutes; (vi) combining said first resin component and said second rType: GrantFiled: November 24, 1993Date of Patent: November 28, 1995Inventor: Barry W. Ryan
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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: 5460750Abstract: A composition and method for breaking crude oil emulsions is disclosed. This composition is a branched, high-molecular weight condensation product of cardanol, an alkylphenol, and an aldehyde, which may be ethoxylated or otherwise derivatized using methods standard in the art. These compositions show good emulsion-breaking performance, especially when used in blends with other compositions.Type: GrantFiled: August 10, 1993Date of Patent: October 24, 1995Assignee: Nalco Chemical CompanyInventor: Hernando Diaz-Arauzo
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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: 5413894Abstract: A phenolic novolak composition prepared by a process comprising the steps of:(1) reacting a first phenolic monomer comprising a major portion of at least one trifunctional phenolic monomer with a first aldehyde source in the absence of a catalyst at a reaction temperature from about 100.degree. C. to about 200.degree. C. and at a reaction pressure of about 2 to about 15 atmospheres to form a phenolic oligomer having a weight average molecular weight from about 500 to about 2,000, having ortho-ortho bonding of about 55% to about 75% of the methylene bonds between the phenolic moieties; and having a time to clear of less than 125 seconds per micron; wherein the mole ratio of said first aldehyde source to said first phenolic monomer is from about 0.3:1.0 to about 0.55:1.0; and(2) then reacting said oligomer with an optional second phenolic source and a second aldehyde source at a temperature from about 80.degree. C. to about 150.degree. C.Type: GrantFiled: May 7, 1993Date of Patent: May 9, 1995Assignee: OCG Microelectronic Materials, Inc.Inventors: Joseph J. Sizensky, Thomas R. Sarubbi, Medhat A. Toukhy
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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: 5380800Abstract: Process for the preparation of modified phenolic resins in which the starting components used for preparation of these modified phenolic resins are subjected to a condensation reaction under pressure and in the presence of an inert organic solvent which forms an azeotrope with water, and in which the water is removed from the reaction mixture continuously by azeotropic distillation. An improved space/time yield is achieved by this pressure distillation.Type: GrantFiled: March 16, 1994Date of Patent: January 10, 1995Assignee: Hoechst AktiengesellschaftInventors: Albert Bender, Wolfgang Dathe
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Patent number: 5371169Abstract: The present invention provides mixture of at least two novolak resins with a molecular weight distribution overlap of at least 50% and having dissolution rates which differ by a factor of at least 2.0. A method is also provided for producing such novolak resin mixtures.Type: GrantFiled: September 28, 1992Date of Patent: December 6, 1994Assignee: Hoechst Celanese CorporationInventors: Ping H. Lu, Anthony Canize, Dinesh N. Khanna, M. Dalil Rahman
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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: 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: 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: 5322757Abstract: Improved photoresist compositions having high resolution and high thermal resistance, produced from certain novolak polymers and diazoquinone photosensitizers. The useful novolak polymers are formed from phenolic mixtures including 2,3,5-trimethyl phenol and/or 2,3-dimethyl phenol, and optional amounts of 2,6-dimethyl phenol, o-cresol and p-cresol.Type: GrantFiled: March 24, 1993Date of Patent: June 21, 1994Assignee: OCG Microelectronic Materials, Inc.Inventor: Charles E. Ebersole
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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: 5302688Abstract: Block phenolic oligomers of the formula (I): ##STR1## These may be reacted alone or 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##Type: GrantFiled: December 3, 1992Date of Patent: April 12, 1994Assignee: OCG Microelectronic Materials, Inc.Inventors: Alfred T. Jeffries, III, Kenji Honda, Andrew J. Blakeney, Sobhy Tadros
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Patent number: 5276126Abstract: A method of planarizing topographical features on a substrate for subsequent coating of a radiation sensitive composition thereon comprising:(1) applying thereover a coating of a planarizing coating layer comprising a planarization layer of novolak resin made by the condensation reaction of an aldehyde source with a phenolic monomeric source comprising at least 25 mole percent of ortho-secondary butyl phenol and a suitable solvent; and(2) heating said coated substrate to remove essentially all of said solvent therefrom and cause said coating to reflow, thereby planarizing the topographical features.Type: GrantFiled: February 8, 1993Date of Patent: January 4, 1994Assignee: OCG Microelectronic Materials, Inc.Inventor: Robert F. Rogler
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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: 5260405Abstract: A binding agent for molding compositions and molded bodies produced by reacting a low molecular weight lignin from the Organosolv process with phenol in a weight ratio of 1:20 to 3:1 at 100.degree. to 180.degree. C., adjusting the pH to an acidic value and condensing the mixture with 0.2 to 0.9 moles of formaldehyde per mole of phenol at 60.degree. to 120.degree. C. to form the binding agent useful for producing curable molding compositions, high-temperature molding compositions, refractory products, textile fleeces and friction coatings as well as carbon materials.Type: GrantFiled: October 26, 1992Date of Patent: November 9, 1993Assignee: Rutgerswerke Aktiengesellschaft AGInventors: Arno Gardziella, Achim Hansen, Stephan Schroter, Josef Suren
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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: 5254639Abstract: A binding agent for molded bodies and molding compositions produced by prereacting a mixture of 5 to 60% by weight of lignin or a lignin fraction produced by the Organosolv process and 40 to 95% by weight of a phenol novolac resin and subjecting the latter to high shear forces in a kneader or extruder and optionally mixing the same with a curing agent useful in molding compositions and high temperature-stable molded products such as refractory products, friction coatings, textile fleeces and carbon or graphite materials.Type: GrantFiled: October 26, 1992Date of Patent: October 19, 1993Assignee: Rutgerswerke Aktiengesellschaft AGInventors: Arno Gardziella, Achim Hansen, Stephan Schroter, Josef Suren
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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
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Patent number: 5234795Abstract: 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
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Patent number: 5233012Abstract: Novel condensates comprising bisphenols and aromatic aminosulfonic acids, in particular, novel 4-aminobenzenesulfonic acid-2,2-bis (hydroxyphenyl)propaneformaldehyde condensates, and methods for their production are disclosed. The novel condensates are useful as a dispersant for disperse dyes, an additive for carbonaceous fine powder-water slurries and as a water reducing agent for cement.Type: GrantFiled: June 8, 1992Date of Patent: August 3, 1993Assignee: Sanyo-Kokusaku Pulp Co., Ltd.Inventors: Masanobu Kawamura, Shinji Hamada, Takashi Date, Toshihiro Sugiwaki, Nobuhiro Hanada