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)
  • Patent number: 5859153
    Abstract: 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: Grant
    Filed: June 21, 1996
    Date of Patent: January 12, 1999
    Assignee: Minnesota Mining and Manufacturing Company
    Inventors: Alan R. Kirk, Allen L. Griggs
  • Patent number: 5847058
    Abstract: 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: Grant
    Filed: April 5, 1996
    Date of Patent: December 8, 1998
    Assignee: Masonite Corporation
    Inventor: Zygmunt Teodorczyk
  • Patent number: 5763558
    Abstract: 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: Grant
    Filed: June 11, 1996
    Date of Patent: June 9, 1998
    Assignee: Compagnie Generale Des Etablissements Michelin-Michelin & Cie
    Inventors: Brigitte Marie Chauvin, Olivier Durel
  • Patent number: 5756599
    Abstract: 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: Grant
    Filed: July 7, 1997
    Date of Patent: May 26, 1998
    Assignee: Masonite Corporation
    Inventor: Zygmunt Teodorczyk
  • Patent number: 5726257
    Abstract: 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: Grant
    Filed: August 28, 1995
    Date of Patent: March 10, 1998
    Assignee: Sumitomo Chemical Company, Ltd.
    Inventors: Youichi Ueda, Yasuhiro Endo, Mitsuhiro Shibata, Kaori Yamasaki
  • Patent number: 5688893
    Abstract: 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: Grant
    Filed: December 20, 1996
    Date of Patent: November 18, 1997
    Assignee: Hoechst Celanese Corporation
    Inventors: M. Dalil Rahman, Daniel P. Aubin, Dana L. Durham, Ralph R. Dammel
  • Patent number: 5684114
    Abstract: 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: Grant
    Filed: June 7, 1995
    Date of Patent: November 4, 1997
    Assignee: Borden Chemical, Inc.
    Inventors: Earl K. Phillips, William D. Detlefsen, Fred E. Carlson
  • Patent number: 5677414
    Abstract: 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: Grant
    Filed: April 25, 1996
    Date of Patent: October 14, 1997
    Assignee: Lord Corporation
    Inventors: Esther Spaltenstein, Ernest B. Troughton, Jr.
  • Patent number: 5674657
    Abstract: 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: Grant
    Filed: November 4, 1996
    Date of Patent: October 7, 1997
    Assignees: Olin Microelectronic Chemicals, Inc., Fuji Photo Film Co., Ltd.,
    Inventors: Shiro Tan, Yasumasa Kawabe, Kenji Honda
  • Patent number: 5652081
    Abstract: 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: Grant
    Filed: September 5, 1996
    Date of Patent: July 29, 1997
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Shiro Tan, Shinji Sakaguchi, Yasumasa Kawabe
  • Patent number: 5646219
    Abstract: 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: Grant
    Filed: June 7, 1995
    Date of Patent: July 8, 1997
    Assignee: Masonite Corporation
    Inventor: Zygmunt Teodorczyk
  • Patent number: 5639806
    Abstract: 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: Grant
    Filed: March 28, 1995
    Date of Patent: June 17, 1997
    Assignee: Borden Chemical, Inc.
    Inventors: Calvin K. Johnson, Kwok-tuen Tse
  • Patent number: 5637658
    Abstract: 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: Grant
    Filed: May 23, 1995
    Date of Patent: June 10, 1997
    Assignee: Masonite Corporation
    Inventor: Zygmunt Teodorczyk
  • Patent number: 5629083
    Abstract: 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: Grant
    Filed: June 7, 1995
    Date of Patent: May 13, 1997
    Assignee: Masonite Corporation
    Inventor: Zygmunt Teodorczyk
  • Patent number: 5578685
    Abstract: 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: Grant
    Filed: June 2, 1995
    Date of Patent: November 26, 1996
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Uwe Neumann, Claus Godau
  • Patent number: 5576108
    Abstract: 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: Grant
    Filed: September 9, 1994
    Date of Patent: November 19, 1996
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Uwe Neumann, Claus Godau
  • Patent number: 5571886
    Abstract: 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: Grant
    Filed: March 21, 1994
    Date of Patent: November 5, 1996
    Assignee: Shipley Company, Inc.
    Inventor: Anthony Zampini
  • Patent number: 5552509
    Abstract: 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: Grant
    Filed: August 31, 1993
    Date of Patent: September 3, 1996
    Assignee: Mitsui Toatsu Chemicals, Inc.
    Inventors: Tomoko Takashima, Shigeru Iimuro, Takashi Kitamura
  • Patent number: 5521259
    Abstract: 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: Grant
    Filed: January 24, 1995
    Date of Patent: May 28, 1996
    Assignee: Kashima Oil Co., Ltd.
    Inventors: Masahiro Tsumura, Masao Tashima, Hiromi Miyasita
  • Patent number: 5510446
    Abstract: 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: Grant
    Filed: June 2, 1995
    Date of Patent: April 23, 1996
    Assignee: Hitachi Chemical Company, Ltd.
    Inventors: Haruaki Sue, Shinsuke Hagiwara, Hiroyuki Saitoh
  • Patent number: 5494785
    Abstract: 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: Grant
    Filed: January 17, 1995
    Date of Patent: February 27, 1996
    Assignee: OCG Microelectronic Materials, Inc.
    Inventors: Joseph J. Sizensky, Thomas R. Sarubbi, Medhat A. Toukhy
  • Patent number: 5494773
    Abstract: 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: Grant
    Filed: March 6, 1995
    Date of Patent: February 27, 1996
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Shiro Tan, Yasumasa Kawabe, Tadayoshi Kokubo
  • Patent number: 5478908
    Abstract: 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: Grant
    Filed: November 14, 1994
    Date of Patent: December 26, 1995
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Wolfgang Hesse, Klaus Rauhut
  • Patent number: 5473045
    Abstract: 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: Grant
    Filed: January 17, 1995
    Date of Patent: December 5, 1995
    Assignee: OCG Microelectronic Materials, Inc.
    Inventors: Joseph J. Sizensky, Thomas R. Sarubbi, Medhat A. Toukhy
  • Patent number: 5470924
    Abstract: 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 r
    Type: Grant
    Filed: November 24, 1993
    Date of Patent: November 28, 1995
    Inventor: Barry W. Ryan
  • Patent number: 5468590
    Abstract: 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: Grant
    Filed: November 29, 1994
    Date of Patent: November 21, 1995
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Kazuhiko Hashimoto, Haruyoshi Osaki, Chinehito Ebina, Kyoko Nagase, Hiroshi Moriuma, Yasunori Uetani
  • Patent number: 5460750
    Abstract: 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: Grant
    Filed: August 10, 1993
    Date of Patent: October 24, 1995
    Assignee: Nalco Chemical Company
    Inventor: Hernando Diaz-Arauzo
  • Patent number: 5459223
    Abstract: 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: Grant
    Filed: February 8, 1994
    Date of Patent: October 17, 1995
    Assignee: Hitachi Chemical Company
    Inventors: Haruaki Sue, Shinsuke Hagiwara, Hiroyuki Saitoh
  • Patent number: 5451484
    Abstract: 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: Grant
    Filed: May 27, 1993
    Date of Patent: September 19, 1995
    Assignee: Sumitomo Chemical Company, Ltd.
    Inventors: Kyoko Nagase, Haruyoshi Osaki, Hiroshi Moriuma
  • Patent number: 5429904
    Abstract: 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: Grant
    Filed: May 27, 1993
    Date of Patent: July 4, 1995
    Assignee: Sumitomo Chemical Company, Ltd.
    Inventors: Kyoko Nagase, Haruyoshi Osaki, Kazuhiko Hashimoto, Hiroshi Moriuma
  • Patent number: 5413894
    Abstract: 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: Grant
    Filed: May 7, 1993
    Date of Patent: May 9, 1995
    Assignee: OCG Microelectronic Materials, Inc.
    Inventors: Joseph J. Sizensky, Thomas R. Sarubbi, Medhat A. Toukhy
  • Patent number: 5395727
    Abstract: 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: Grant
    Filed: November 29, 1993
    Date of Patent: March 7, 1995
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Yasunori Uetani, Haruyoshi Osaki, Naoki Takeyama, Yuji Ueda, Hiromi Ueki, Takehiro Kusumoto
  • Patent number: 5380800
    Abstract: 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: Grant
    Filed: March 16, 1994
    Date of Patent: January 10, 1995
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Albert Bender, Wolfgang Dathe
  • Patent number: 5371169
    Abstract: 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: Grant
    Filed: September 28, 1992
    Date of Patent: December 6, 1994
    Assignee: Hoechst Celanese Corporation
    Inventors: Ping H. Lu, Anthony Canize, Dinesh N. Khanna, M. Dalil Rahman
  • Patent number: 5350827
    Abstract: 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: Grant
    Filed: February 9, 1994
    Date of Patent: September 27, 1994
    Assignee: OCG Microelectronic Materials, Inc.
    Inventors: Thomas R. Sarubbi, Joseph J. Sizensky
  • Patent number: 5346799
    Abstract: 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: Grant
    Filed: December 7, 1992
    Date of Patent: September 13, 1994
    Assignee: OCG Microelectronic Materials, Inc.
    Inventors: Alfred T. Jeffries, III, David J. Brzozowy
  • Patent number: 5326665
    Abstract: 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: Grant
    Filed: March 1, 1993
    Date of Patent: July 5, 1994
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Haruyoshi Osaki, Hiroshi Moriuma, Yasunori Uetani
  • Patent number: 5322757
    Abstract: 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: Grant
    Filed: March 24, 1993
    Date of Patent: June 21, 1994
    Assignee: OCG Microelectronic Materials, Inc.
    Inventor: Charles E. Ebersole
  • Patent number: 5302687
    Abstract: 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: Grant
    Filed: March 29, 1993
    Date of Patent: April 12, 1994
    Assignee: Ashland Oil, Inc.
    Inventors: Billy M. Culbertson, Omar Tiba, Gilbert M. Gynn
  • Patent number: 5302688
    Abstract: 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: Grant
    Filed: December 3, 1992
    Date of Patent: April 12, 1994
    Assignee: OCG Microelectronic Materials, Inc.
    Inventors: Alfred T. Jeffries, III, Kenji Honda, Andrew J. Blakeney, Sobhy Tadros
  • Patent number: 5276126
    Abstract: 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: Grant
    Filed: February 8, 1993
    Date of Patent: January 4, 1994
    Assignee: OCG Microelectronic Materials, Inc.
    Inventor: Robert F. Rogler
  • Patent number: 5268444
    Abstract: 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: Grant
    Filed: April 2, 1993
    Date of Patent: December 7, 1993
    Assignee: The United States of America as represented by the Administrator of the National Aeronautics and Space Administration
    Inventors: Brian J. Jensen, Robert G. Bryant, Paul M. Hergenrother
  • Patent number: 5260405
    Abstract: 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: Grant
    Filed: October 26, 1992
    Date of Patent: November 9, 1993
    Assignee: Rutgerswerke Aktiengesellschaft AG
    Inventors: Arno Gardziella, Achim Hansen, Stephan Schroter, Josef Suren
  • Patent number: 5254440
    Abstract: 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: Grant
    Filed: September 30, 1992
    Date of Patent: October 19, 1993
    Assignee: OCG Microelectronic Materials, Inc.
    Inventor: Medhat A. Toukhy
  • Patent number: 5254639
    Abstract: 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: Grant
    Filed: October 26, 1992
    Date of Patent: October 19, 1993
    Assignee: Rutgerswerke Aktiengesellschaft AG
    Inventors: Arno Gardziella, Achim Hansen, Stephan Schroter, Josef Suren
  • Patent number: 5250653
    Abstract: 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: Grant
    Filed: February 22, 1993
    Date of Patent: October 5, 1993
    Assignee: OCG Microelectronic Materials, Inc.
    Inventor: Medhat A. Toukhy
  • Patent number: 5237037
    Abstract: 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: Grant
    Filed: June 12, 1991
    Date of Patent: August 17, 1993
    Assignee: OCG Microelectronic Materials, Inc.
    Inventor: Charles E. Ebersole
  • Patent number: 5235022
    Abstract: 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: Grant
    Filed: November 23, 1992
    Date of Patent: August 10, 1993
    Assignee: OCG Microelectronic Materials, Inc.
    Inventors: Alfred T. Jeffries, III, Kenji Honda, Andrew J. Blakeney, Sobhy Tadros
  • Patent number: 5234795
    Abstract: 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: Grant
    Filed: November 23, 1992
    Date of Patent: August 10, 1993
    Assignee: OCG Microelectronic Materials, Inc.
    Inventors: Alfred T. Jeffries, III, Kenji Honda, Andrew J. Blakeney, Sobhy Tadros
  • Patent number: 5233012
    Abstract: 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: Grant
    Filed: June 8, 1992
    Date of Patent: August 3, 1993
    Assignee: Sanyo-Kokusaku Pulp Co., Ltd.
    Inventors: Masanobu Kawamura, Shinji Hamada, Takashi Date, Toshihiro Sugiwaki, Nobuhiro Hanada