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: 5232819Abstract: 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: August 3, 1993Assignee: OCG Microelectronic Materials, Inc.Inventors: Alfred T. Jeffries, III, Kenji Honda, Andrew J. Blakeney, Sobhy Tadros
-
Patent number: 5218038Abstract: The invention relates to the modification of a curable phenolic resin system by the incorporation of alkylphenol, alkoxyphenol, arylphenol or aryloxyphenol. The resulting resin has reduced water soluble leachates which, in turn, improves the break time when the resin is used to coat proppants for treating subterranean formations.Type: GrantFiled: November 14, 1991Date of Patent: June 8, 1993Assignee: Borden, Inc.Inventors: Calvin R. Johnson, Kwok-tuen Tse, Charles J. Korpics
-
Patent number: 5216111Abstract: 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: October 22, 1990Date of Patent: June 1, 1993Assignee: Shipley Company Inc.Inventor: Anthony Zampini
-
Patent number: 5206333Abstract: A copolycondensation of a phenol, a naphthol and formaldehyde proceeds smoothly in the presence of an acid and a metallic element selected from the group consisting of transition metallic elements and metallic elements of Group IIa, Group IIIa, Group IVa, Group Va and Group VIa of the Periodic Table, and a naphthol-modified phenolic resin which has a large molecular weight and does not gel is obtained.Type: GrantFiled: May 7, 1992Date of Patent: April 27, 1993Assignee: Hitachi Chemical Company, Ltd.Inventors: Haruaki Sue, Ken Nanaumi, Takuji Itou, Ken Madarame, Shinsuke Hagiwara
-
Patent number: 5202403Abstract: A modified resole resin and an adhesive composition containing the resin wherein the resin is prepared by first reacting formaldehyde and a phenol at a mole ratio of formaldehyde to phenol of less than about 1.0 in the presence of alkaline in an amount sufficient to provide a mole ratio of said alkaline material to phenol between about 0.04 and 0.08 to form a precursor resin; reacting the precursor resin with lignin to form a lignin-modified phenol-formaldehyde precursor resin, and then reacting the lignin-modified phenol-formaldehyde precursor with additional formaldehyde sufficient to provide a cumulative formaldehyde to phenol mole ratio of between about 2.0 and about 3.0. The adhesive composition is useful in bonding wood chips, veneers and sheets of plywood.Type: GrantFiled: January 15, 1992Date of Patent: April 13, 1993Assignee: Georgia-Pacific Resins, Inc.Inventor: Glen A. Doering
-
Patent number: 5196289Abstract: 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: June 4, 1991Date of Patent: March 23, 1993Assignee: OCG Microelectronic Materials, Inc.Inventors: Alfred T. Jeffries, III, Kenji Honda, Andrew J. Blakeney, Sobhy Tadros
-
Patent number: 5188921Abstract: A block copolymer novolak resin composition comprising at least one unit of the reaction product of an alkali-soluble phenolic moiety having at least two phenolic nuclei and at least two unsubstituted positions ortho and para to the hydroxyls in the moiety 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: June 4, 1991Date of Patent: February 23, 1993Assignee: OCG Microelectronic Materials, Inc.Inventors: Alfred T. Jeffries, III, Kenji Honda, Andrew J. Blakeney, Sobhy Tadros
-
Patent number: 5182184Abstract: Novolak resins are provided which are the condensation product of (a) a phenol, phenol derivative, or mixtures thereof, and (b) a mixture of formaldehyde or a formaldehyde precursor and (1) a monohydroxy aromatic aldehyde and wherein at least a portion of the hydroxyl groups thereof are esterified or (2) a mixture of at least one monohydroxy aromatic aldehyde and at least one non-hydroxylic aromatic aldehyde; the novolak resins having a hydroxyl number of from about 120 to about 180 grams of resin per equivalent of hydroxyl. The novolak resins are especially useful in positive photoresist formulations and have enhanced photospeed and film loss characteristics as well as improved thermal stability.Type: GrantFiled: February 5, 1990Date of Patent: January 26, 1993Assignee: Morton International, Inc.Inventors: Richard M. Lazarus, Randall Kautz, Sunit S. Dixit
-
Patent number: 5177172Abstract: 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: February 13, 1991Date of Patent: January 5, 1993Assignee: OCG Microelectronic Materials, Inc.Inventor: Medhat A. Toukhy
-
Patent number: 5162156Abstract: An adhesion promoting composition for enhancing adhesion between an elastomeric substrate and a metal surface which, when applied at least in substantial contact with the metal surface, produces an elastomer-metal adhesive bond that withstands high temperature fluid and corrosive material environments and that can be applied without extensive pretreatment of the metal surface. The adhesion promoting composition comprises a phenolic resin derived from a first phenolic component, a second phenolic component, and a formaldehyde source, wherein the first phenolic component is a monohydroxy aromatic compound, a dihydroxy aromatic compound or a combination thereof, and the second phenolic component is a trihydroxy aromatic compound. A two-part adhesive composition containing a primer component and an overcoat component is also disclosed.Type: GrantFiled: September 21, 1990Date of Patent: November 10, 1992Assignee: Lord CorporationInventors: Ernest B. Troughton, Jr., Helmut W. Kucera
-
Patent number: 5155164Abstract: Products of the condensation of phenolmonosulfonic acids, dihydroxydiphenyl sulfones, urea and formaldehyde can be obtained by(A) preparing a homogeneous reaction mixture in sulfuric acid from the phenolmonosulfonic acid and dihydroxydiphenyl sulfone in the molar ratio of from 3:1 to 10:1, with the proviso that the water content of the mixture is not more than 10% of the total weight of the components, and the mixture contains from 0.3 to 1.5 moles of sulfuric acid per mole of dihydroxydiphenyl sulfone, at from 100.degree. to 180.degree. C.,(B) subsequently, at from 40.degree. to 90.degree. C., carrying out a precondensation with 1 to 2 moles of formaldehyde and 0.5 to 1.5 moles of urea per mole of phenol units present in aqueous medium,(C) partially neutralizing the reaction mixture,(D) adding to the partially neutralized reaction mixture 0 to 0.5 mole of phenol per mole of phenol units present and then 0.1 to 0.8 mole of formaldehyde per mole of phenol units then present,(E) further condensing at from 40.Type: GrantFiled: May 8, 1991Date of Patent: October 13, 1992Assignee: BASF AktiengesellschaftInventors: Hermann Graf, Adolf Stuebinger, Klaus Lorenz, Ortwin Schaffer, Karl Stork
-
Patent number: 5151339Abstract: Process for producing dimer-free phenolic polymers, particularly novolak polymers produced from cresol mixtures, and photoresist compositions containing such dimer-free novolak polymers. The process comprises reacting phenolic polymers containing phenolic dimers with a capping agent, such as a silylating agent, to cap all of the phenolic hydroxy groups. This reduces the distillation temperature of the capped dimers and renders the capped polymer stable at such distillation temperature. The capped dimers are distilled off, and finally the phenolic polymer is uncapped. Dimer-free novolaks produce scum-free developed photoresist images.Type: GrantFiled: May 15, 1991Date of Patent: September 29, 1992Assignee: OCG Microelectronic Materials, Inc.Inventor: Thomas R. Sarubbi
-
Patent number: 5132376Abstract: Process for producing dimer-free phenolic polymers, particularly novolak polymers produced from cresol mixtures, and photoresist compositions containing such dimer-free novolak polymers. The process comprises reacting phenolic polymers containing phenolic dimers with a capping agent, such as a silylating agent, to cap all of the phenolic hydroxy groups. This reduces the distillation temperature of the capped dimers and renders the capped polymer stable at such distillation temperature. The capped dimers are distilled off, and finally the phenolic polymer is uncapped. Dimer-free novolaks produce scum-free developed photoresist images.Type: GrantFiled: December 20, 1990Date of Patent: July 21, 1992Assignee: OCG Microelectronic Materials, Inc.Inventor: Thomas R. Sarubbi
-
Patent number: 5130409Abstract: Novolak resins are provided which are the condensation product of (a) a phenol, phenol derivative, or mixtures thereof, and (b) a mixture of formaldehyde or a formaldehyde precursor and an aromatic aldehyde. When the aromatic aldehyde is a monohydroxy aromatic aldehyde, the novolak resin is especially useful in positive photoresist formulations.Type: GrantFiled: November 16, 1990Date of Patent: July 14, 1992Assignee: Morton International, Inc.Inventors: Richard M. Lazarus, Randall Kautz, Sunit S. Dixit
-
Patent number: 5096996Abstract: Modified novolaks based on phenols which are trifunctional with respect to formaldehyde and contain, as modifying components, terpenes and unsaturated carboxylic acids or derivatives of these compounds, the weight ratio between the terpenes and the unsaturated carboxylic acids or derivatives thereof being in the range from 98.5:2.5 to 2.5:98.5 and the weight ratio between the phenolic component and the sum of the modified components being in the range from 95:5 to 5:95 and the modified novolaks having a melting point greater than 45.degree. C.Process for the preparation of the modified novolaks by admixing the modifying components indicated with non-modified novolaks in the necessary amounts at temperatures between 80.degree. and 300.degree. C.Use of the modified novolaks as reinforcing resins for rubber and elastomers, as tackifying agents for rubber, as binders for friction linings, curable molding compositions, impregnants, coatings, paints and binders for finely divided inorganic substrates.Type: GrantFiled: October 2, 1989Date of Patent: March 17, 1992Assignee: Hoechst AktiengesellschaftInventors: Wolfgang Hesse, Erhard Leicht, Richard Sattelmeyer
-
Patent number: 5089589Abstract: The preparation of novolaks from phenols or mixtures of different phenols, and oxo compounds or mixtures of oxo compounds by condensation of the reactants in a medium having a low water content in homogeneous phase at temperature of .gtoreq.110.degree. C., preferably between 115.degree. and 200.degree. C. and preferably at normal pressure, in the presence of water-immiscible and/or only partially water-miscible inert organic solvents and of acids as catalysts with removal of water by distillation, the medium having a low water content being prepared or maintained by distilling off water from the reaction mixture, preferably by azeotropic distillation. Particular advantages are obtained when readily volatile oxo compounds, in particular aqueous formaldehyde solutions, are used.Type: GrantFiled: January 22, 1990Date of Patent: February 18, 1992Assignee: Hoechst AktiengesellschaftInventors: Wolfgang Hesse, Klaus Hofmann, Erhard Leicht
-
Patent number: 5075413Abstract: A fire resistant resin for use as a binder in reinforced plastics and a resultant reinforced plastic includes the reaction product of (a) at least one resorcinol component selected from the group consisting of resorcinol and resorcinol formaldehyde novolak resin, and (b) a phenolic resole resin. The reaction may be achieved in the presence of an alkaline catalyst.A method of making a fire resistant resin binder for reinforced plastics and the method of making such reinforced plastics including, (a) at least one resorcinol component selected from the group consisting of resorcinol and resorcinol formaldehyde novolak resin, and (b) a phenolic resole resin. The reaction may be achieved in the presence of an alkaline catalyst.Type: GrantFiled: September 4, 1990Date of Patent: December 24, 1991Assignee: Indspec Chemical CorporationInventor: Theodore H. Dailey, Jr.
-
Patent number: 5075414Abstract: A fire resistant resin for use as a binder in reinforced plastics and a resultant reinforced plastic includes the reaction product of (a) at least one resorcinol component selected from the group consisting of resorcinol and resorcinol formaldehyde novolak resin, and (b) a phenolic resole resin. The reaction may be achieved in the presence of an alkaline catalyst.A method of making a fire resistant resin binder for reinforced plastics and the method of making such reinforced plastics including, (a) at least one resorcinol component selected from the group consisting of resorcinol and resorcinol formaldehyde novolak resin, and (b) a phenolic resole resin. The reaction may be achieved in the presence of an alkaline catalyst.Type: GrantFiled: September 4, 1990Date of Patent: December 24, 1991Assignee: Indspec Chemical CorporationInventor: Theodore H. Dailey, Jr.
-
Patent number: 5051454Abstract: The present invention relates to phenolic resin compositions and methods for making cured phenolic resin compositions. The phenolic resin compositions of this invention comprise an esterified phenolic compound and a base and optionally an unesterified phenolic resole resin. The composition cures in the presence of water or other polar solvent. The esterified phenolic compound contains at least one phenolic hydroxyl group or an esterified phenolic hydroxyl group and further contains at least one esterified methylol group positioned ortho or para to a phenolic hydroxyl group or an esterified phenolic group.The compounds find particular use in bonding refractory materials, such as sand, in the production of foundry moulds and cores and in treating subterranean formations. These composition have the advantage that cure can be obtained at room temperature without the use of strong alkali. The use of this system also prevents the release of alcohols during the saponification stage of the ester cure process.Type: GrantFiled: December 15, 1989Date of Patent: September 24, 1991Assignee: Borden, Inc.Inventors: Peter H. R. B. Lemon, James G. King, Graham Murray, Henry Leoni, Arthur H. Gerber
-
Patent number: 5049629Abstract: A color developer for pressure-sensitive copying paper is disclosed, containing a polyvalent metal-modification product of a p-substituted phenolformaldehyde condensate substantially terminated with an o-substituted phenol nucleus, with a content of a condensate component in which each of both terminal phenol nuclei thereof has a hydrogen atom at the o-position being not more than 20% by weight based on the total condensate. The color developer exhibits excellent color developability, undergoes no yellowing, and provides a color image having excellent water resistance.Type: GrantFiled: November 3, 1989Date of Patent: September 17, 1991Assignee: Mitsubishi Petrochemical Co., Ltd.Inventors: Kazuhide Hayama, Yukio Saitoh
-
Patent number: 5049641Abstract: A rubber compounding resin which is low fuming, nonhygroscopic and low in free resorcinol. It is made by first reacting resorcinol or other phenolic compound and styrene or other vinyl compound in a molar ratio of 1.0 mole of resorcinol to 0.25 to 1.0 mole of styrene after which formaldehyde or other aldehyde is added in the amount of 0.5 to 0.7 moles. Alternatively, the resorcinol can first be reacted with the formaldehyde after which the styrene is added. The composition resulting from the above procedure has been identified as having the structure ##STR1## wherein X is hydroxyl, hydrogen or an alkyl group having 1 to 4 carbon atoms. An intermediate in making the above compound has been identified as having the structure.Type: GrantFiled: July 1, 1988Date of Patent: September 17, 1991Assignee: Indspec Chemical CorporationInventors: Richard T. Hood, Robert M. Lamars
-
Patent number: 5043412Abstract: A raw batch composition for use in making a shaped article such as a foundry shape or refractory article is disclosed. The composition comprises a mixture of an aggregate material; a phenol formaldehyde novolak resin; a phenol formaldehyde resole resin; and an ester functional curing agent. A shaped article prepared from the composition and processes for making a refractory body or foundry article are also disclosed.Type: GrantFiled: September 1, 1989Date of Patent: August 27, 1991Assignee: Borden, Inc.Inventors: Pitchaiya Chandramouli, Raja Iyer, Calvin Johnson
-
Patent number: 5039777Abstract: An aniline-resorcin-formaldehyde copolycondensation product having a particular mol ratio of aniline to resorcin is used in an adhesive composition for well adhering fibrous material to rubber.Type: GrantFiled: January 23, 1991Date of Patent: August 13, 1991Assignee: Bridgestone CorporationInventors: Toshihiro Yotsumoto, Koichi Morita, Takeshi Kinoshita
-
Patent number: 5023311Abstract: Disclosed is a novel, organic solvent-soluble novolak resin having a high molecular weight and an inherent viscosity of at least 0.1. This high-molecular-weight novolak resin can be prepared with a good reproducibility by reacting an aldehyde with a polyfunctional phenol at an aldehyde/polyfunctional phenol molar ratio of from 0.85 to 1.20 in the presence of an acid catalyst in a solution state. This high-molecular-weight novolak resin is valuable as the resin component of a radiation-sensitive resist.Type: GrantFiled: November 30, 1988Date of Patent: June 11, 1991Assignee: Toray Industries, Inc.Inventor: Takashi Kubota
-
Patent number: 5021522Abstract: An improved vulcanizable rubber composition of the type comprising (I) a rubber component selected from natural rubber, synthetic rubber or combinations thereof, and (II) a methylene donor compound which generates formaldehyde upon heating, and (III) a phenolic novolak resin type methylene acceptor compound is disclosed. The improvement comprises having at least ten mole percent of the phenolic groups of the phenolic novolak resin aralkylated with one or more compounds selected from the group consisting of styrene, alpha methyl styrene, beta methyl styrene, p-methyl styrene, alpha chloro styrene and vinyl naphthalenes.Type: GrantFiled: February 21, 1990Date of Patent: June 4, 1991Assignee: Indspec Chemical CorporationInventors: Bojayan Durairaj, Alex Peterson, Jr., Robert M. Lamars, Richard T. Hood
-
Patent number: 4859563Abstract: Disclosed herein is a positive photoresist composition containing (a) a photosensitizer of 1,2-napthtoquinone diazides photosensitive-material comprising an ester of 2,3,4,4'-tetrahydroxybenzophenone in which on the average, not less than two hydroxyl groups of 2,3,4,4'-tetrahydroxybenzophenone have been esterified by 1,2-naphthoquinonediazide-5-sulfonic acid and (b) a novolak resin obtained by condensing a mixture of m-cresol, p-cresol and 2,5-xylenol with formaldehyde.Type: GrantFiled: March 9, 1987Date of Patent: August 22, 1989Assignee: Mitsubishi Chemical Industries LimitedInventors: Konoe Miura, Tameichi Ochiai, Yasuhiro Kameyama
-
Patent number: 4841002Abstract: Compositions have melting points below 100.degree. C. which are useful in the formation of resins by reaction with polyphenolic compounds consisting of a mixture of more than two compounds having the formula ##STR1## wherein A represents a cyclic or acyclic aliphatic or substituted cyclic or acyclic aliphatic moiety having from 1 to 20 carbon atoms or an aromatic mono- or multi-nuclear or aliphatic substituted aryl residue having from 6 to 20 carbon atoms,R independently represents H, CH.sub.3, CH.sub.2 CH.sub.3 or C.sub.6 H.sub.5,R.sup.1 independently represents H or CH.sub.3,R.sup.2 independently represents H or CH.sub.3, andx represents an integer from 0 to 2are described.Type: GrantFiled: November 8, 1988Date of Patent: June 20, 1989Assignee: Ashland Oil, IncInventors: Billy M. Culbertson, Omar Tiba
-
Patent number: 4839446Abstract: A polymerizable thermosetting composition which is a flowable liquid at moderate temperatures which comprises a mixture of:(A) from about 75% to about 95% by weight of a mixture of:(1) from about 80% to about 20% by weight of a bisoxazoline and(2) from about 20% to about 80% by weight of a polyphenolic compound and(B) from about 5% to about 25% by weight of at least one member selected from the group consisting of a monooxazoline and a monooxazine,a method for forming thermoset products therefrom and the novel thermoset products resulting from said method are described.Type: GrantFiled: August 8, 1988Date of Patent: June 13, 1989Assignee: Ashland Oil, Inc.Inventors: Billy M. Culbertson, Omar Tiba
-
Patent number: 4839457Abstract: A developing composition and a sheet for a pressure-sensitive copy paper comprising a phenolic resin as a main component which is obtained by condensating with formaldehyde using a p-substituted phenol with a 2,4-di-substituted and/or 2,6-di-substituted phenol, and zinc oxide which may be added thereto, as occasion demands.Type: GrantFiled: March 18, 1988Date of Patent: June 13, 1989Assignee: Mitsubishi Petrochemical Co., Ltd.Inventors: Kazuhide Hayama, Yukio Saitoh
-
Patent number: 4835240Abstract: An epoxy resin composition comprising a trifunctional epoxy resin derived from a trisphenol having the structure represented by the following general formula ##STR1## wherein R represents a hydrogen atom, an alkyl group or a halogen atom, and a novolak-type phenolic resin. This epoxy resin composition gives a cured product having excellent pliability and a high glass transition temperature. It is especially useful as a semiconductor encapsulating material.Type: GrantFiled: May 31, 1988Date of Patent: May 30, 1989Assignee: Mitsui Petrochemical Industries, Ltd.Inventors: Eiki Togashi, Toshimasa Takata
-
Patent number: 4820576Abstract: A flame-retardant polymer is created by forming a first resin typically by reacting resorcinol with furfural in a ratio of one mole of the former to less than a mole of the latter in the presence of an alkaline catalyst. A resole is then formed by reacting typically phenol with formaldehyde in a ratio of one mole of phenol to more than a mole of the aldehyde in the presence of an alkaline catalyst. The first resin and resole are mixed together with a powered oxyborate compound such as zinc borate and allowed to polymerize to form the polymer.Type: GrantFiled: February 18, 1988Date of Patent: April 11, 1989Assignee: Fiber Materials, Inc.Inventor: Harold E. Duryea
-
Patent number: 4812551Abstract: A novolak resin for a positive photoresist is provided herein, which resin is produced by the addition condensation reaction of a phenol with formaldehyde. This novolak resin has improved heat resistant and sensitivity properties and the thickness retention of the novolak resins are very high.Type: GrantFiled: November 9, 1987Date of Patent: March 14, 1989Assignee: Sumitomo Chemical Company, LimitedInventors: Fumio Oi, Haruyoshi Osaki, Akihiro Furuta, Yukikazu Uemura, Takao Ninomiya, Yasunori Uetani, Makoto Hanabata
-
Patent number: 4806267Abstract: Compositions having melting points below 100.degree. C. which are useful in the formation of resins by reaction with polyphenolic compounds consisting of a mixture of more than two compounds having the formula ##STR1## wherein A represents a cyclic or acyclic aliphatic or substituted cyclic or acyclic aliphatic moiety having from 1 to 20 carbon atoms or an aromatic mono- or multi-nuclear or aliphatic substituted aryl residue having from 6 to 20 carbon atoms,R independently represents H, CH.sub.3, CH.sub.2 CH.sub.3 or C.sub.6 H.sub.5,R.sup.1 independently represents H or CH.sub.3,R.sup.2 independently represents H or CH.sub.3, andx represents an integer from 0 to 2as described.Type: GrantFiled: January 15, 1988Date of Patent: February 21, 1989Assignee: Ashland Oil, Inc.Inventors: Billy M. Culbertson, Omar Tiba
-
Patent number: 4800118Abstract: A light stabile composition for imparting stain resistance to polyamide fiber-containing textile articles (e.g. nylon, wool or silk carpets) comprises a halogenated (e.g. brominated or chlorinated) aryl group-containing product of the condensation polymerization of a hydroxyaryl sulfonic acid (e.g., para-hydroxyphenyl sulfonic acid), a dihydroxydiaryl sulfone (e.g., dihydroxydiphenyl sulfone) and an aldehyde (e.g., formaldehyde). The polyamide fiber-containing textile articles are converted to a stain resistant product by containing the fibers with an acidified aqueous solution of the aforesaid composition.Type: GrantFiled: November 4, 1987Date of Patent: January 24, 1989Assignee: West Point PepperellInventors: John W. Reed, Richard D. Smith
-
Patent number: 4656239Abstract: The process described herein involves the gradual addition of aqueous formaldehyde, containing 35-60 percent by weight of formaldehyde, to a phenol maintained at a temperature of 60.degree.-100.degree. C., preferably 70.degree.-90.degree. C., and at a reduced pressure of 11-26 inches of mercury in the presence of an alkaline catalyst. The rate of formaldehyde addition is such that the exothermic reaction aids in maintaining the stated temperature range and thereby simultaneously distills approximately all the water added with the formaldehyde and that formed by the condensation so that the volume of the reaction mass is maintained approximately constant. This constant volume allows efficient use of the equipment.Type: GrantFiled: March 27, 1986Date of Patent: April 7, 1987Assignee: Plastics Engineering CompanyInventors: Phillip A. Waitkus, Bohumir Lepeska
-
Patent number: 4652620Abstract: The disclosure is directed to thermoset resinous compositions having utility in the area of surface coating and molding applications, the latter including the preparation of high performance composites and the use in reaction injection molding processes. The contemplated compositions are obtained by polymerizing a reaction mixture comprising a polyfunctional 2-oxazoline compound, a compound or oligomer containing a plurality of aromatic hydroxyl groups and a polyfunctional epoxide.Type: GrantFiled: October 4, 1985Date of Patent: March 24, 1987Assignee: Ashland Oil, Inc.Inventors: Timothy A. Tufts, Billy M. Culbertson
-
Patent number: 4642264Abstract: The object of the present invention are new thermoset resins having quickened curing, a process for their preparation, and their applications. The resins according to the invention consist, at least in part, of the products resulting from the polycondensation of one or more pyridine derivatives containing at least two methyl groups in the 2, 4 or 6 positions, with one or more aromatic dialdehydes, and the addition of one or more additives consisting of phenol compounds. These resins are used to the fabrication of composite materials.Type: GrantFiled: August 23, 1984Date of Patent: February 10, 1987Assignees: Societe Nationale des Poudres et Explosifs, Office National d'Etudes et de Recherches AerospatialesInventors: Marcel Ropars, Bertrand Bloch
-
Patent number: 4639496Abstract: Method for the manufacture of a polymer with triaromatic methane units as basic building blocks, the electric conductivity of which is obtained through the formation of charge transfer complexes. Electron donors and/or electron acceptors are added to the synthetic polymer during or after its preparation, for forming charge transfer complexes.Type: GrantFiled: August 29, 1985Date of Patent: January 27, 1987Assignee: Brown, Boveri & Cie AGInventors: Gerd Weddigen, Robert Huber, Birgit Schmidt, Hartmut Schneider
-
Patent number: 4639505Abstract: The process for preparing novel polymers containing ether-amide groups by reaction of a bis- or poly-bicyclic amide acetal with a bis-phenolic or poly-phenolic material at a temperature of from about 80.degree. C. to 200.degree. C. is described.Type: GrantFiled: August 7, 1985Date of Patent: January 27, 1987Assignee: Ashland Oil, Inc.Inventor: Anil B. Goel
-
Patent number: 4613662Abstract: A process comprising copolymerizing an oxazoline with a bis-or poly-phenolic compound in the presence of a catalyst which is a cationic complex of an alkali or an alkaline earth metal at a temperature in the range of from about 100.degree. to 200.degree. C. is described.Type: GrantFiled: August 7, 1985Date of Patent: September 23, 1986Assignee: Ashland Oil, Inc.Inventor: Anil B. Goel
-
Patent number: 4608408Abstract: A phenol-resorcinol-formaldehyde resin and a method for making the same. In this method phenol and formaldehyde at an initial pH of 8.5 to 9.2 are reacted in the presence of a sodium sulfite catalyst. The reaction mixture is heated and refluxed until it has a viscosity of u-v on the Gardner bubble test. Additional resorcinol is added to the mixture and refluxing is continued until it has a viscosity of 30 to 100 Garner sections. The reaction mixture is diluted with a water miscible solvent to obtain a resin solution having a solids content of about 40 to 60 percent by weight and a viscosity of 2.0 to 3.5 poise. An alkali metal carbonate material in the amount of 4 to 8 percent by weight of the resin is added to make adhesives including this resin fast curing. Fumed silica is also added to the resin solution by means of high shear apparatus to make the solution thixotropic.Type: GrantFiled: April 24, 1985Date of Patent: August 26, 1986Assignee: Koppers Company, Inc.Inventors: Richard T. Hood, Raymond L. Bender
-
Patent number: 4578448Abstract: Disclosed are high-ortho phenol-formaldehyde resoles having stable hemiformal groups. These resoles are of low viscosity, are essentially free of unbound water and volatile organic compounds. They are curable to phenolic formaldehyde resinous solids and are particularly suitable for use in liquid injection molding processes to form composites.Type: GrantFiled: December 14, 1983Date of Patent: March 25, 1986Assignee: Union Carbide CorporationInventors: George L. Brode, Sui-Wu Chow
-
Patent number: 4564466Abstract: Method for the manufacture of a polymer with triaromatic methane units as basic building blocks, the electric conductivity of which is obtained through the formation of charge transfer complexes. Electron donors and/or electron acceptors are added to the synthetic polymer during or after its preparation, for forming charge transfer complexes.Type: GrantFiled: December 21, 1983Date of Patent: January 14, 1986Assignee: Brown, Boveri & Cie AGInventors: Gerd Weddigen, Robert Huber, Birgit Schmidt, Hartmut Schneider
-
Patent number: 4542204Abstract: A method for a condensate of an aldehyde compound and a phenol compound, said method comprising dispersing a viscous condensate obtained by the reaction of an aldehyde compound with a phenol compound into cold water or hot water by the aid of a dispersing agent, and then solidifying said condensate.Type: GrantFiled: October 28, 1983Date of Patent: September 17, 1985Assignee: Kanegafuchi Kagaku Kogyo Kabushiki KaishaInventors: Hiroshi Shibahara, Hiromitsu Tachibana
-
Patent number: 4529682Abstract: Cresol-formaldehyde novolak resins made from a mixture containing meta- and paracresol or ortho-, meta- and paracresol in a ratio selected from a given range for use in fast positive photoresist compositions together with one or more sensitizing compounds. When dissolved in a mixture of organic solvents, the photoresist compositions are suitable for application as a thin coating to a substrate. After the coating has been dried, the coated substrate can be exposed to image-wise modulated actinic radiation and developed in alkaline solution, yielding a relief pattern of resist on substrate useful for a number of applications.Type: GrantFiled: August 2, 1982Date of Patent: July 16, 1985Assignee: Philip A. Hunt Chemical CorporationInventor: Medhat A. Toukhy
-
Patent number: 4529751Abstract: A phenolic resin for application in foundry shell molding operations having improved properties is disclosed. The phenolic resin is prepared by reacting aldehydes and a mixture of bisphenol A and bisphenol F to prepare a phenolic resin for coating foundry aggregates or sand to prepare shell molds having low thermal expansion and improved shake out properties.Type: GrantFiled: October 17, 1983Date of Patent: July 16, 1985Assignee: Sumitomo Durez Company, Ltd.Inventor: Yukio Saeki
-
Patent number: 4485194Abstract: Polyoxyalkylene foam stabilizing surfactants can be prepared by reacting a polyoxyalkylene adduct, a cyclic nitrogenous vinyl monomer and an esterified unsaturated dibasic acid under free radical polymerization conditions in the presence of a free radical initiator, and by subjecting the reaction product obtained to a solvent extraction. The isolated components can be utilized as surfactants in producing cellular foams.Type: GrantFiled: October 17, 1983Date of Patent: November 27, 1984Assignee: The Celotex CorporationInventors: Richard L. Frentzel, Ernest K. Moss
-
Patent number: 4476191Abstract: A method of preparing a thermoplastic, water-soluble, phenolic aldehyde resin and the composition are provided to enhance the flexibility and resistance to compression fatigue breakage of glass fibers to which the resin has been applied. The method involves two steps. In the first step, the phenolic compound and the aldehyde are reacted to less than 100 percent completion in an amount so that the aldehyde to phenolic compound ratio is in the range of about 0.6 to about 1.5 and at an acidic pH and for a period of time equivalent to about 3 hours to about 10 hours when the temperature is in the range of about 55.degree. F. (13.degree. C.) to about 90.degree. F. (32.degree. C.) to produce a resinous mixture. In the second stage the pH of the reaction is adjusted within the range above about 7.0 to about 7.Type: GrantFiled: September 29, 1982Date of Patent: October 9, 1984Assignee: PPG Industries, Inc.Inventor: Mikhail M. Girgis
-
Patent number: 4468507Abstract: Large-scale preparation of branched novolacs by the acid catalyzed, exothermic condensation of methylol-reactive phenols with polymethylol diphenols is made practical by first carrying out the reaction on a scale which permits temperature control simply by cooling and then separately adding more of the premixed reactants and the catalyst at rates such that the temperature of the reaction mixture can readily be controlled.Type: GrantFiled: November 21, 1983Date of Patent: August 28, 1984Assignee: The Dow Chemical CompanyInventor: Theodore L. Parker
-
Patent number: 4461859Abstract: A method of preparing a thermoplastic, water-soluble, phenolic aldehyde resin and the composition are provided to enhance the flexibility and resistance to compression fatigue breakage of glass fibers to which the resin has been applied. The method involves two steps. In the first step, the phenolic compound and the aldehyde are reacted to less than 100 percent completion in an amount so that the aldehyde to phenolic compound ratio is in the range of about 0.6 to about 1.5 and at an acidic pH and for a period of time equivalent to about 3 hours to about 10 hours when the temperature is in the range of about 55.degree. F. (13.degree. C.) to about 90.degree. F. (32.degree. C.) to produce a resinous mixture. In the second stage the pH of the reaction is adjusted within the range above about 7.0 to about 7.Type: GrantFiled: September 29, 1982Date of Patent: July 24, 1984Assignee: PPG Industries, Inc.Inventor: Mikhail M. Girgis