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: 5232819
    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: August 3, 1993
    Assignee: OCG Microelectronic Materials, Inc.
    Inventors: Alfred T. Jeffries, III, Kenji Honda, Andrew J. Blakeney, Sobhy Tadros
  • Patent number: 5218038
    Abstract: 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: Grant
    Filed: November 14, 1991
    Date of Patent: June 8, 1993
    Assignee: Borden, Inc.
    Inventors: Calvin R. Johnson, Kwok-tuen Tse, Charles J. Korpics
  • Patent number: 5216111
    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: October 22, 1990
    Date of Patent: June 1, 1993
    Assignee: Shipley Company Inc.
    Inventor: Anthony Zampini
  • Patent number: 5206333
    Abstract: 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: Grant
    Filed: May 7, 1992
    Date of Patent: April 27, 1993
    Assignee: Hitachi Chemical Company, Ltd.
    Inventors: Haruaki Sue, Ken Nanaumi, Takuji Itou, Ken Madarame, Shinsuke Hagiwara
  • Patent number: 5202403
    Abstract: 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: Grant
    Filed: January 15, 1992
    Date of Patent: April 13, 1993
    Assignee: Georgia-Pacific Resins, Inc.
    Inventor: Glen A. Doering
  • Patent number: 5196289
    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: June 4, 1991
    Date of Patent: March 23, 1993
    Assignee: OCG Microelectronic Materials, Inc.
    Inventors: Alfred T. Jeffries, III, Kenji Honda, Andrew J. Blakeney, Sobhy Tadros
  • Patent number: 5188921
    Abstract: 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: Grant
    Filed: June 4, 1991
    Date of Patent: February 23, 1993
    Assignee: OCG Microelectronic Materials, Inc.
    Inventors: Alfred T. Jeffries, III, Kenji Honda, Andrew J. Blakeney, Sobhy Tadros
  • Patent number: 5182184
    Abstract: 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: Grant
    Filed: February 5, 1990
    Date of Patent: January 26, 1993
    Assignee: Morton International, Inc.
    Inventors: Richard M. Lazarus, Randall Kautz, Sunit S. Dixit
  • Patent number: 5177172
    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: February 13, 1991
    Date of Patent: January 5, 1993
    Assignee: OCG Microelectronic Materials, Inc.
    Inventor: Medhat A. Toukhy
  • Patent number: 5162156
    Abstract: 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: Grant
    Filed: September 21, 1990
    Date of Patent: November 10, 1992
    Assignee: Lord Corporation
    Inventors: Ernest B. Troughton, Jr., Helmut W. Kucera
  • Patent number: 5155164
    Abstract: 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: Grant
    Filed: May 8, 1991
    Date of Patent: October 13, 1992
    Assignee: BASF Aktiengesellschaft
    Inventors: Hermann Graf, Adolf Stuebinger, Klaus Lorenz, Ortwin Schaffer, Karl Stork
  • Patent number: 5151339
    Abstract: 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: Grant
    Filed: May 15, 1991
    Date of Patent: September 29, 1992
    Assignee: OCG Microelectronic Materials, Inc.
    Inventor: Thomas R. Sarubbi
  • Patent number: 5132376
    Abstract: 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: Grant
    Filed: December 20, 1990
    Date of Patent: July 21, 1992
    Assignee: OCG Microelectronic Materials, Inc.
    Inventor: Thomas R. Sarubbi
  • Patent number: 5130409
    Abstract: 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: Grant
    Filed: November 16, 1990
    Date of Patent: July 14, 1992
    Assignee: Morton International, Inc.
    Inventors: Richard M. Lazarus, Randall Kautz, Sunit S. Dixit
  • Patent number: 5096996
    Abstract: 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: Grant
    Filed: October 2, 1989
    Date of Patent: March 17, 1992
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Wolfgang Hesse, Erhard Leicht, Richard Sattelmeyer
  • Patent number: 5089589
    Abstract: 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: Grant
    Filed: January 22, 1990
    Date of Patent: February 18, 1992
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Wolfgang Hesse, Klaus Hofmann, Erhard Leicht
  • Patent number: 5075413
    Abstract: 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: Grant
    Filed: September 4, 1990
    Date of Patent: December 24, 1991
    Assignee: Indspec Chemical Corporation
    Inventor: Theodore H. Dailey, Jr.
  • Patent number: 5075414
    Abstract: 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: Grant
    Filed: September 4, 1990
    Date of Patent: December 24, 1991
    Assignee: Indspec Chemical Corporation
    Inventor: Theodore H. Dailey, Jr.
  • Patent number: 5051454
    Abstract: 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: Grant
    Filed: December 15, 1989
    Date of Patent: September 24, 1991
    Assignee: Borden, Inc.
    Inventors: Peter H. R. B. Lemon, James G. King, Graham Murray, Henry Leoni, Arthur H. Gerber
  • Patent number: 5049629
    Abstract: 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: Grant
    Filed: November 3, 1989
    Date of Patent: September 17, 1991
    Assignee: Mitsubishi Petrochemical Co., Ltd.
    Inventors: Kazuhide Hayama, Yukio Saitoh
  • Patent number: 5049641
    Abstract: 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: Grant
    Filed: July 1, 1988
    Date of Patent: September 17, 1991
    Assignee: Indspec Chemical Corporation
    Inventors: Richard T. Hood, Robert M. Lamars
  • Patent number: 5043412
    Abstract: 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: Grant
    Filed: September 1, 1989
    Date of Patent: August 27, 1991
    Assignee: Borden, Inc.
    Inventors: Pitchaiya Chandramouli, Raja Iyer, Calvin Johnson
  • Patent number: 5039777
    Abstract: 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: Grant
    Filed: January 23, 1991
    Date of Patent: August 13, 1991
    Assignee: Bridgestone Corporation
    Inventors: Toshihiro Yotsumoto, Koichi Morita, Takeshi Kinoshita
  • Patent number: 5023311
    Abstract: 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: Grant
    Filed: November 30, 1988
    Date of Patent: June 11, 1991
    Assignee: Toray Industries, Inc.
    Inventor: Takashi Kubota
  • Patent number: 5021522
    Abstract: 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: Grant
    Filed: February 21, 1990
    Date of Patent: June 4, 1991
    Assignee: Indspec Chemical Corporation
    Inventors: Bojayan Durairaj, Alex Peterson, Jr., Robert M. Lamars, Richard T. Hood
  • Patent number: 4859563
    Abstract: 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: Grant
    Filed: March 9, 1987
    Date of Patent: August 22, 1989
    Assignee: Mitsubishi Chemical Industries Limited
    Inventors: Konoe Miura, Tameichi Ochiai, Yasuhiro Kameyama
  • Patent number: 4841002
    Abstract: 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: Grant
    Filed: November 8, 1988
    Date of Patent: June 20, 1989
    Assignee: Ashland Oil, Inc
    Inventors: Billy M. Culbertson, Omar Tiba
  • Patent number: 4839446
    Abstract: 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: Grant
    Filed: August 8, 1988
    Date of Patent: June 13, 1989
    Assignee: Ashland Oil, Inc.
    Inventors: Billy M. Culbertson, Omar Tiba
  • Patent number: 4839457
    Abstract: 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: Grant
    Filed: March 18, 1988
    Date of Patent: June 13, 1989
    Assignee: Mitsubishi Petrochemical Co., Ltd.
    Inventors: Kazuhide Hayama, Yukio Saitoh
  • Patent number: 4835240
    Abstract: 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: Grant
    Filed: May 31, 1988
    Date of Patent: May 30, 1989
    Assignee: Mitsui Petrochemical Industries, Ltd.
    Inventors: Eiki Togashi, Toshimasa Takata
  • Patent number: 4820576
    Abstract: 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: Grant
    Filed: February 18, 1988
    Date of Patent: April 11, 1989
    Assignee: Fiber Materials, Inc.
    Inventor: Harold E. Duryea
  • Patent number: 4812551
    Abstract: 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: Grant
    Filed: November 9, 1987
    Date of Patent: March 14, 1989
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Fumio Oi, Haruyoshi Osaki, Akihiro Furuta, Yukikazu Uemura, Takao Ninomiya, Yasunori Uetani, Makoto Hanabata
  • Patent number: 4806267
    Abstract: 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: Grant
    Filed: January 15, 1988
    Date of Patent: February 21, 1989
    Assignee: Ashland Oil, Inc.
    Inventors: Billy M. Culbertson, Omar Tiba
  • Patent number: 4800118
    Abstract: 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: Grant
    Filed: November 4, 1987
    Date of Patent: January 24, 1989
    Assignee: West Point Pepperell
    Inventors: John W. Reed, Richard D. Smith
  • Patent number: 4656239
    Abstract: 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: Grant
    Filed: March 27, 1986
    Date of Patent: April 7, 1987
    Assignee: Plastics Engineering Company
    Inventors: Phillip A. Waitkus, Bohumir Lepeska
  • Patent number: 4652620
    Abstract: 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: Grant
    Filed: October 4, 1985
    Date of Patent: March 24, 1987
    Assignee: Ashland Oil, Inc.
    Inventors: Timothy A. Tufts, Billy M. Culbertson
  • Patent number: 4642264
    Abstract: 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: Grant
    Filed: August 23, 1984
    Date of Patent: February 10, 1987
    Assignees: Societe Nationale des Poudres et Explosifs, Office National d'Etudes et de Recherches Aerospatiales
    Inventors: Marcel Ropars, Bertrand Bloch
  • Patent number: 4639496
    Abstract: 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: Grant
    Filed: August 29, 1985
    Date of Patent: January 27, 1987
    Assignee: Brown, Boveri & Cie AG
    Inventors: Gerd Weddigen, Robert Huber, Birgit Schmidt, Hartmut Schneider
  • Patent number: 4639505
    Abstract: 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: Grant
    Filed: August 7, 1985
    Date of Patent: January 27, 1987
    Assignee: Ashland Oil, Inc.
    Inventor: Anil B. Goel
  • Patent number: 4613662
    Abstract: 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: Grant
    Filed: August 7, 1985
    Date of Patent: September 23, 1986
    Assignee: Ashland Oil, Inc.
    Inventor: Anil B. Goel
  • Patent number: 4608408
    Abstract: 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: Grant
    Filed: April 24, 1985
    Date of Patent: August 26, 1986
    Assignee: Koppers Company, Inc.
    Inventors: Richard T. Hood, Raymond L. Bender
  • Patent number: 4578448
    Abstract: 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: Grant
    Filed: December 14, 1983
    Date of Patent: March 25, 1986
    Assignee: Union Carbide Corporation
    Inventors: George L. Brode, Sui-Wu Chow
  • Patent number: 4564466
    Abstract: 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: Grant
    Filed: December 21, 1983
    Date of Patent: January 14, 1986
    Assignee: Brown, Boveri & Cie AG
    Inventors: Gerd Weddigen, Robert Huber, Birgit Schmidt, Hartmut Schneider
  • Patent number: 4542204
    Abstract: 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: Grant
    Filed: October 28, 1983
    Date of Patent: September 17, 1985
    Assignee: Kanegafuchi Kagaku Kogyo Kabushiki Kaisha
    Inventors: Hiroshi Shibahara, Hiromitsu Tachibana
  • Patent number: 4529682
    Abstract: 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: Grant
    Filed: August 2, 1982
    Date of Patent: July 16, 1985
    Assignee: Philip A. Hunt Chemical Corporation
    Inventor: Medhat A. Toukhy
  • Patent number: 4529751
    Abstract: 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: Grant
    Filed: October 17, 1983
    Date of Patent: July 16, 1985
    Assignee: Sumitomo Durez Company, Ltd.
    Inventor: Yukio Saeki
  • Patent number: 4485194
    Abstract: 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: Grant
    Filed: October 17, 1983
    Date of Patent: November 27, 1984
    Assignee: The Celotex Corporation
    Inventors: Richard L. Frentzel, Ernest K. Moss
  • Patent number: 4476191
    Abstract: 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: Grant
    Filed: September 29, 1982
    Date of Patent: October 9, 1984
    Assignee: PPG Industries, Inc.
    Inventor: Mikhail M. Girgis
  • Patent number: 4468507
    Abstract: 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: Grant
    Filed: November 21, 1983
    Date of Patent: August 28, 1984
    Assignee: The Dow Chemical Company
    Inventor: Theodore L. Parker
  • Patent number: 4461859
    Abstract: 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: Grant
    Filed: September 29, 1982
    Date of Patent: July 24, 1984
    Assignee: PPG Industries, Inc.
    Inventor: Mikhail M. Girgis