Material Contains A Sulfur Atom Patents (Class 528/143)
  • 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: 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: 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: 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: 5013814
    Abstract: Sulfonium salts of the formulae I to IV ##STR1## in which A is C.sub.1 -C.sub.12 alkyl, C.sub.3 -C.sub.8 cycloalkyl, C.sub.4 -C.sub.10 cycloalkylalkyl, phenyl which is unsubstituted or mono- or polysubstituted by C.sub.1 -C.sub.8 alkyl, C.sub.1 -C.sub.4 alkoxy, halogen, nitro, phenyl, phenoxy, alkoxycarbonyl having 1-4 C atoms in the alkoxy radical or acyl having 1-12 C atoms, Ar, Ar.sup.1 and Ar.sup.2, independently of one another, are each unsubstituted or mono- or polysubstituted phenyl, or naphthyl which is unsubstituted or mono- or polysubstituted each arylene is an unsubstituted or mono- or polysubstituted phenylene or unsubstituted or mono- or polysubstituted naphthylene and Q.sup..crclbar. is SbF.sub.6 --, AsF.sub.6 -- or SbF.sub.5 OH-- are valuable curing agents and curing accelerators in the heat-curing of cationically polymerizable compounds, preferably epoxy resins.
    Type: Grant
    Filed: January 9, 1990
    Date of Patent: May 7, 1991
    Assignee: Ciba-Geigy Corporation
    Inventors: Martin Roth, Beat Muller
  • Patent number: 4942217
    Abstract: A heat-hardenable binder comprising (a) a phenolic resin of a phenolic compound and formaldehyde in a molar ratio of 1:1 to 1:2 and (b) an effective amount of a hardener mixture of hexamethylenetetramine and an acidic latent hardening agent with reduced emission problems and curing rapidly.
    Type: Grant
    Filed: October 26, 1988
    Date of Patent: July 17, 1990
    Assignee: Rutgerswerke AG
    Inventors: Arno Gardziella, Alois Kwasniok
  • Patent number: 4904516
    Abstract: A process for preparing a water soluble phenol-formaldehyde resole resin having improved storage stability employs a calcium compound to catalyze the condensation reaction which occurs under basic conditions. Sulfamic acid is used to neutralize the resole solution, yielding a soluble calcium salt which will not settle out of the solution or clog transfer lines or spray nozzles as may a calcium salt precipitated during the neutralization. Glass fiber insulation produced using a binder prepared with the aqueous resole solution shows enhanced thickness recovery and lower odor potential.
    Type: Grant
    Filed: January 12, 1988
    Date of Patent: February 27, 1990
    Inventor: Albert W. Creamer
  • Patent number: 4904753
    Abstract: Disclosed is a catalyst system which improves the cure time of acid-catalyzable resole resins while providing extended shelf life thereof. Broadly, the present invention includes a method for formulating an acid-catalyzed, non-aqueous resole resin composition and to the composition itself. The catalyst system comprises an acid catalyst and an oxidizing agent in an amount adequate for cure in at least about the same time that occurs by use of at least twice the amount of said acid catalyst alone. The shelf life of the catalyzed resole resin is greater with the inventive catalyst system than with an equivalent resole resin containing only the acid catalyst in twice the amount.
    Type: Grant
    Filed: March 23, 1988
    Date of Patent: February 27, 1990
    Assignee: Ashland Oil, Inc.
    Inventors: Golden F. Watts, Warren L. Robbins
  • Patent number: 4757108
    Abstract: A water soluble phenolic resole-urea composition useful as a binder which remains infinitely water-dilutable and free of sediment after one month of storage at 0.degree. C. and is made by the reaction of urea with the free formaldehyde in a phenolic resole under acid conditions, followed by the further addition of urea at neutral or slightly basic conditions.
    Type: Grant
    Filed: June 18, 1986
    Date of Patent: July 12, 1988
    Assignee: Borden, Inc.
    Inventor: Wayne R. Walisser
  • Patent number: 4698401
    Abstract: A polyfunctional reaction product having functional phenolic OH groups is made available by reacting a phenol and an alkoxylated amino-aldehyde condensation product in the presence of a solvent and of an acid catalyst. This method makes it possible to prepare a polyfunctional phenolic reaction product which is soluble in organic solvents at a low ratio of phenolic OH groups to alkoxy groups without gelling. The reaction product is particularly useful as a curing agent for epoxy resins.
    Type: Grant
    Filed: September 9, 1985
    Date of Patent: October 6, 1987
    Assignee: The Dow Chemical Company
    Inventors: Dieter H. Klein, Raymond Koenig
  • Patent number: 4663418
    Abstract: An improved moisture-stable phenolic resin binder with calcium ions from the catalyst complexed with the phenolic resin and a process for its preparation and laminate boards with the said binder as the binding agent.
    Type: Grant
    Filed: December 31, 1985
    Date of Patent: May 5, 1987
    Assignee: Rutgerswerke Aktiengesellschaft
    Inventors: Karl Jellinek, Rolf Muller, Gerhard Wisomirski
  • 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: 4603162
    Abstract: A resin having a monomer unit structure represented by the formula: ##STR1## can be cured by an actinic irradiation such as electron beam, ultraviolet ray or infrared ray to give a heat-resistant, moisture-resistant, acid- and alkali-resistant and solvent-resistant film which is especially suitable for a paint vehicle resin for use in resistor element or magnetic recording medium. A composition comprising said resin modified by incorporating at least of one monomer or oligomer containing at least one acryl, methacryl or allyl group therein for facilitating the control of the characteristics of a resistor element obtained by using said composition is also disclosed.
    Type: Grant
    Filed: June 12, 1984
    Date of Patent: July 29, 1986
    Assignee: Matsushita Electric Industrial Co., Ltd.
    Inventors: Yo Hasegawa, Satoshi Murakawa, Yukihiro Shimazaki
  • Patent number: 4593052
    Abstract: Polymerizable compositions contain (A) a cationically polymerizable material, such as an epoxide resin, a phenoplast or a cyclic vinyl ether, (B) a hydroxy compound such as styreneallyl alcohol copolymer, and (c) an aromatic iodosyl salt of formula ##STR1## where R.sup.3 and R.sup.4, which may be the same or different, each represent a monovalent aromatic radical having from 4 to 25 carbon atoms, x denotes 1, 2 or 3, and Z.sup.x- denotes an x-valent anion of a protic acid.Suitable salts of formula II include diphenyliodosyl hexafluorophosphate and tetrafluoroborate. The compositions may be photopolymerized or they may be thermally polymerized in the presence, as catalyst for the iodosyl salt, of a salt or complex of a d-block transition metal, a stannous salt, an organic peroxide or an activated .alpha.-hydroxy compound.The compositions may be used as surface coatings and adhesives, and in the preparation of printing plates, printed circuits and reinforced composites.
    Type: Grant
    Filed: November 19, 1984
    Date of Patent: June 3, 1986
    Assignee: Ciba-Geigy Corporation
    Inventor: Edward Irving
  • Patent number: 4587291
    Abstract: Binders are described based on acid curing phenol resins and acid curing agents which, after mixing, have an extended processability time but nevertheless exhibit a rapid curing time at relatively low temperatures. They are obtained by using, as the resin, aqueous phenol resols and, as the curing agent, either copper, aluminum, or iron(III) salts of aromatic sulfonic acids or addition products of hydroxy-containing, water-compatible polyols with aromatic sulfonic acids or mixtures of these salts and the polyol addition products. The binders are used for impregnation of fabrics, for production of abrasives and for fiber reinforced plastics.
    Type: Grant
    Filed: April 25, 1985
    Date of Patent: May 6, 1986
    Assignee: Rutgerswerke Aktiengesellschaft
    Inventors: Arno Gardziella, Karl-Heinz Schwieger, Peter Adolphs, Gerhard Grossmann
  • Patent number: 4579892
    Abstract: A low cost method of binding lignocellulosic materials utilizing a novel ammonium based spent sulphite liquor, with phenol and formaldehyde or phenol-formaldehyde thermosetting resin as the binder is disclosed. Phenol-formaldehyde which normally reacts with ammonium lignosulfonate under acidic conditions and is unstable under these conditions, can be dispersed or otherwise held in suspension and can be mixed direct with the material by spraying. The constituants of the novel binder can also be mechanically dispersed when in dry powder form. The binder has improved adhesion characteristics and a shorter cure time over existing binders using a spent sulphite liquor base when in combination with phenol-formaldehyde.
    Type: Grant
    Filed: May 29, 1984
    Date of Patent: April 1, 1986
    Assignee: Forintek Canada Corp.
    Inventors: Louis R. Calve, Gilles G. Brunette
  • Patent number: 4403076
    Abstract: A fast curing shell molding composition having the tensile strength of a conventional novolac resin when cured contains a fast curing novolac resin comprising a methylene chained polyphenylol wherein a major portion of the methylene linkages are coupled to adjacent phenylol groups at the o-o' and p-p' position, wherein at least about 19% of the methylene linkages are coupled to adjacent phenylol groups at the o-o' portions, and wherein at least about 3% of the total number of methylene linkages are coupled to adjacent phenylol groups at the p-p' positions. The shell molding composition is produced from the fast curing novolac resin by uniformly coating refractory granules with the fast curing resin. The fast curing novolac resin can be prepared by blending a conventional novolac resin with a novolac resin having a large proportion of methylene linkages coupled to adjacent phenylol groups at the o-o' position.
    Type: Grant
    Filed: March 5, 1982
    Date of Patent: September 6, 1983
    Assignee: Pacific Resins & Chemicals, Inc.
    Inventor: Roderick A. McDonald
  • Patent number: 4400492
    Abstract: Disclosed is a color-developer for pressure-sensitive recording sheets, comprising a co-condensate of a reaction intermediate of a p-substituted phenol and a trifunctional or higher phenol, or a polyvalent metal salt of said co-condensate, said reaction intermediate being obtained by the reaction of said p-substituted phenol under acidic conditions with formaldehyde or a substance capable of generating formaldehyde.
    Type: Grant
    Filed: March 24, 1981
    Date of Patent: August 23, 1983
    Assignee: Mitsui Toatsu Chemicals, Inc.
    Inventors: Makoto Asano, Saburo Kawashima, Yoshimitu Tanabe, Hisamichi Murakami
  • Patent number: 4398014
    Abstract: New aromatic sulfonylsulfoxonium salts are of formula ##STR1## where q is 1 to 4,R denotes an aliphatic, cycloaliphatic, or aromatic group,R.sup.6 denotes H, an alkyl or aralkyl group, or a group --COR.sup.9, --CO--NH--(CO).sub.r --R.sup.10, or --SO.sub.2 --R.sup.11, where r is zero or 1,one, but not both, of R and R.sup.6 denoting an aromatic group,R.sup.7 denotes an alkyl, alkenyl, cycloalkyl, cycloalkylalkyl, or aralkyl group,R.sup.8 has the same meaning as R.sup.7 but may alternatively represent a dialkylamino group or, if R.sup.7 denotes alkyl, it may alternatively represent an arylamino group,R.sup.9, R.sup.10, and R.sup.11 each denote an alkyl, aryl, or aralkyl radical of 1 to 25 carbon atoms,t is 1, 2, or 3, andZ.sup.- denotes a t-valent anion of a protic acid.The salts, e.g., dimethyl-p-toluenesulfonylmethylsufoxonium hexafluorophosphate, are useful as catalysts for the polymerization of cationically polymerizable materials by means of actinic radiation and/or heat.
    Type: Grant
    Filed: October 23, 1981
    Date of Patent: August 9, 1983
    Assignee: Ciba-Geigy Corporation
    Inventors: George E. Green, Edward Irving, Bernard P. Stark
  • Patent number: 4395535
    Abstract: A process for the manufacture of condensation products of phenols and isobutyraldehyde by reacting the phenols and isobutyraldehyde at elevated temperature in a mole ratio of 0.5:1 to 1.5:1 in the presence of acid or compounds hydrolyzable to acids as catalysts, subsequent neutralization and removal of the resultant reaction water by distillation wherein the reaction products obtained in this manner are also subjected to a water-vapor distillation.
    Type: Grant
    Filed: October 6, 1981
    Date of Patent: July 26, 1983
    Assignee: BASF Aktiengesellschaft
    Inventors: Juergen Nieberle, Karl-Clemens Peters, Wolfgang Reuther, Heinz-Hilmar Bankowsky
  • Patent number: 4384027
    Abstract: A composite comprising a steel cords-covering rubber composition and a rubber composition which is contiguous thereto and contains a thiazole type vulcanization accelerator, at least one of these rubber compositions containing a m-cresol resin whereby they can be cured without decreasing the resulting strength of bond therebetween even after they have been left uncured in contact with each other for a considerable time.
    Type: Grant
    Filed: April 20, 1982
    Date of Patent: May 17, 1983
    Assignee: The Yokohama Rubber Co., Ltd.
    Inventors: Shinji Kawakami, Yasuhiro Ishikawa
  • Patent number: 4383098
    Abstract: A catalyst material is described, particularly useful in making core sand from which resin bound sand shapes are made. The preferred catalyst is a material comprising at least one salt made from a weak base and an acid from the group comprising lower aliphatic and aromatic hydrocarbon sulfonic acids. The curable resin binder is preferably a furfuryl alcohol polymer or other furan-based material. The resin is preferably present in an amount of about 0.5% to about 5% based on the weight of sand, while the catalyst is present in an amount of about 5% to 40% by weight of the resin material. The catalyzed composition provides an excellent combination of working or bench life, rapid curing on a delayed action basis and favorable shape-imparting and holding properties in the formed sand shapes. Specifically preferred compositions include aluminum and copper phenol and toluene sulfonic acid salts.
    Type: Grant
    Filed: July 13, 1981
    Date of Patent: May 10, 1983
    Assignee: The Quaker Oats Company
    Inventor: James E. Menting
  • Patent number: 4383025
    Abstract: Substances (I) capable of being converted into higher-molecular weight materials under the influence of a cationic catalyst, such as 1,2-epoxides, aminoplasts, vinyl monomers and prepolymers, or phenoplasts, are so converted by exposure to actinic radiation in the presence of an aryl- or aroyl- carbamoylsulfoxonium salt (II) of formula ##STR1## where p is zero or 1,q is 1 to 4,Ar denotes an aromatic group,R.sup.6 denotes --H or group --COR.sup.9 or --CONH(CO).sub.r R.sup.10,R.sup.7 denotes an alkyl, alkenyl, cycloalkyl, cycloalkylalkyl, aryl, or aralkyl group,R.sup.8 has the same meaning as R.sup.7 but may alternatively represent a dialkylamino group or, if R.sup.7 denotes alkyl, it may alternatively represent an arylamino group,R.sup.9 and R.sup.10 each denote a saturated or ethylenically unsaturated radical,r is zero or 1,t is 1, 2, or 3, andZ.sup.t- denotes a t-valent anion of a protic acid.
    Type: Grant
    Filed: June 29, 1981
    Date of Patent: May 10, 1983
    Assignee: Ciba-Geigy Corporation
    Inventors: George E. Green, Edward Irving
  • Patent number: 4378453
    Abstract: An adhesive consisting comprising an alkoxyphenol derivative/resorcin derivative/formaldehyde cocondensate has a high adhesive strength and can bond firmly polyester fibrous material with rubber.
    Type: Grant
    Filed: April 6, 1982
    Date of Patent: March 29, 1983
    Assignee: Bridgestone Tire Co., Ltd.
    Inventors: Toshihiro Yotsumoto, Kazuo Koyama
  • Patent number: 4376854
    Abstract: A process for preparing a resorcinol copolymer, comprising at least one specific phenol with formaldehyde at a certain mole ratio to obtain a resol-type precondensate containing 1 to 30% of residual unreacted formaldehyde and then adding said resol-type precondensate to a mixture of an acid catalyst and at least one resorcinol to effect co-condensation. The obtained copolymer is useful for an adhesive for polyester fiber and rubber.
    Type: Grant
    Filed: April 5, 1982
    Date of Patent: March 15, 1983
    Assignee: Hodogaya Chemical Co., Ltd.
    Inventors: Toyohiko Yamaguchi, Koichi Kashima, Nobuo Kaifu
  • Patent number: 4374962
    Abstract: An adhesive comprising a cocondensate of formaldehyde with m-alkylphenol or its derivative and alkylresorcin is excellent in the adhesion, heat resistance and flexibility and can bond firmly polyester fibrous material with rubber.
    Type: Grant
    Filed: April 6, 1982
    Date of Patent: February 22, 1983
    Assignee: Bridgestone Tire Company Limited
    Inventors: Toshihiro Yotsumoto, Kazuo Koyama
  • Patent number: 4350800
    Abstract: A process for the preparation of synthetic resins based on resorcinol compounds which comprises reacting a resorcinol pitch which is obtained in the manufacture of resorcinol from benzenedisulfonic acid in at least one step with an oxo-compound selected from aldehydes, ketones and compounds based on or splitting off at least one of these substances, and the use of the products as binders for abrasive articles.
    Type: Grant
    Filed: September 14, 1981
    Date of Patent: September 21, 1982
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Wolfgang Hesse, Franz Landauer, Klaus Schmiedel
  • Patent number: 4340700
    Abstract: A process for preparing a resin containing phenolic groups, in which an aralkylene ether of formula ROCH.sub.2.Ar. CH.sub.2 OR, wherein Ar represents a phenylene group and R is an alkyl group of 1-4 carbon atoms, is reacted with a phenol containing 1-3 hydroxyl groups and at least 2 hydrogen atoms in the aromatic phenolic nucleus, wherein (1) an ether composition which comprises at least 50 molar % e.g. 50-100% of said ether and the remainder of said composition, if any i.e. up to 50% (such as 0.1-50%) is selected from aromatic compounds each with an Ar nucleus having two substituents selected from CH.sub.3, CH.sub.2 OR, CHO, CH(OR).sub.2, said phenol and (2) an added compound of formula R'CHO or R'CH (OR.sup.2).sub.2, wherein R' is monovalent phenyl group or substituted phenyl group, in which each substituent is an alkyl group of 1-4 carbon atoms or a chlorine atom, and R.sup.
    Type: Grant
    Filed: August 19, 1981
    Date of Patent: July 20, 1982
    Assignee: Albright & Wilson Limited
    Inventor: Alfred G. Edwards
  • Patent number: 4339567
    Abstract: Substances (I) capable of being converted into higher-molecular weight materials under the influence of a cationic catalyst, such as 1,2-epoxides, aminoplasts, vinyl monomers or prepolymers, or phenoplasts, are so converted by exposure to actinic radiation in the presence of a sulphoxonium salt (II) of formula ##STR1## where P denotes zero or 1,R.sup.6 denotes an arylene or aralkylene group,R.sup.7 denotes --H or a group of formula ##STR2## R.sup.8 denotes an alkyl, alkenyl, cycloalkyl, cycloalkylalkyl, aryl, or aralkyl group,R.sup.9 has the same meaning as R.sup.8 but may alternatively represent a dialkylamino group or, if R.sup.8 represents an alkyl group, R.sup.9 may represent an arylamino group,R.sup.10 and R.sup.11 each independently have the same meaning as R.sup.8 but may also each denote --H,r represents 1, 2, or 3,Z.sup.r- denotes an r-valent anion of a protic acid, and q denotes zero when p denotes zero, or zero or 1 when p denotes 1.
    Type: Grant
    Filed: February 23, 1981
    Date of Patent: July 13, 1982
    Assignee: Ciba-Geigy Corporation
    Inventors: George E. Green, Edward Irving
  • Patent number: 4337334
    Abstract: A process for producing a phenolic resin comprising condensing a phenol component and an aldehyde component, characterized in that the phenol component comprises (high-molecular-weight phenolic compounds which are left after bisphenol A-containing by-products formed in the production of bisphenol A by condensing acetone and phenol in the presence of an acid catalyst are treated at a high temperature of at least 150.degree. C. in the presence of an alkaline catalyst to remove low-boiling components therefrom.
    Type: Grant
    Filed: February 10, 1981
    Date of Patent: June 29, 1982
    Assignee: Mitsui Toatsu Chemicals Inc.
    Inventors: Yoshiro Shimizu, Toshio Itakura, Mitsuhiro Iwasa, Kunio Hanauye
  • Patent number: 4336366
    Abstract: Cationically polymerizable compounds, for example cyclic ethers, can be thermally polymerised if an aromatic iodonium salt of the formula I[(Ar.sup.1)(Ar.sup.2)I].sup.+ [MX.sub.n ].sup.- (I)in which Ar.sup.1 Ar.sup.2, M, X and n are as defined in claim 1, is used as the catalyst and an agent which forms free radicals on heating and has the formula III or IV ##STR1## in which R.sup.2, R.sup.3, R.sup.5, R.sup.6, R.sup.8 and m are as defined in claim 1, for example a benzpinacol silyl ether, is used as the co-catalyst. The process is of particular importance for heat-curing epoxide resins as a one-component system.
    Type: Grant
    Filed: February 20, 1981
    Date of Patent: June 22, 1982
    Assignee: Ciba-Geigy Corporation
    Inventors: Godwin Berner, Rudolf Kirchmayr
  • Patent number: 4320043
    Abstract: Binders for foundry core sands and the like comprising furfuryl alcohol and an aromatic dialdehyde and optionally an aromatic alcohol.
    Type: Grant
    Filed: January 12, 1981
    Date of Patent: March 16, 1982
    Assignee: The Quaker Oats Company
    Inventor: Hugh C. Anderson
  • Patent number: 4310653
    Abstract: A method of producing essentially monomeric etherified formaldehyde condensates with a bisphenol having a plurality of formaldehyde-reactive sites is disclosed in which the bisphenol is reacted with at least about 2 moles of formaldehyde per mole of bisphenol in solution in etherifying alcohol in the presence of an insoluble strong acid cation exchange resin. The reaction is carried out at a reaction temperature of from about 30.degree. C. to about 100.degree. C. to simultaneously provide the desired methylolation and etherification without introducing soluble ionic contaminants.
    Type: Grant
    Filed: October 8, 1980
    Date of Patent: January 12, 1982
    Assignee: DeSoto, Inc.
    Inventors: John J. Krajewski, Edward J. Murphy
  • Patent number: 4299938
    Abstract: Substances (I) capable of being converted into higher-molecular weight materials under the influence of a cationic catalyst, such as 1,2-epoxides, aminoplasts, vinyl monomers or prepolymers, or phenoplasts, are so converted by exposure to actinic irradiation or by heating in the presence of an aryloxysulfoxonium salt of formula ##STR1## where either R.sup.6 and R.sup.7 separately denote lower alkyl (optionally substituted by halogen and interrupted in the chain by --O-- or --SO.sub.2 --), or an aryl or aryloxy group, or R.sup.6 and R.sup.7 together denote a divalent group forming with the S atom a heterocyclic radical; R.sup.8 denotes an aryl group; M denotes an atom of a metal or metalloid; X denotes a halogen atom; and n is 4, 5, or 6, for instance,p-chlorophenoxy-p-tolyl-p-phenoxysulfoxonium hexafluorophosphate and 1-phenoxy-1-oxidotetrahydrothiophenium tetrafluorborate.
    Type: Grant
    Filed: June 9, 1980
    Date of Patent: November 10, 1981
    Assignee: Ciba-Geigy Corporation
    Inventors: George E. Green, Edward Irving
  • Patent number: 4281098
    Abstract: Phenol/aldehyde condensation reactions are short-stopped by the addition of an aqueous solution of a salt of a weak acid and a metal of Groups III to VIII of the Periodic Table.
    Type: Grant
    Filed: October 24, 1979
    Date of Patent: July 28, 1981
    Assignee: BP Chemicals Limited
    Inventor: Bryan H. McCormick
  • Patent number: 4268657
    Abstract: Improved friction elements suited for use for example in an automotive or similar brake or in a clutch are provided by employing therein as a binder the reaction product of phenol, formaldehyde, and monoalkylphenol having from 4 to about 20 carbon atoms in the alkyl group. The mole ratio range of phenol:alkylphenol:formaldehyde is about 2:1-5:1-7 and the number of moles of phenol and alkylphenol combined exceeds the number of moles of formaldehyde. An improved method of making friction elements is also provided which uses such binder.
    Type: Grant
    Filed: December 10, 1979
    Date of Patent: May 19, 1981
    Assignee: Minnesota Mining and Manufacturing Company
    Inventor: Anthony P. Manzara
  • Patent number: 4259454
    Abstract: Curable organic resin compositions, such as epoxy resins, are provided, based on the use of dialkyl hydroxy arylsulfonium salts in combination with certain orgainc oxidants such as iodosoaromatic esters, or the use of certain amines or transition metals in combination with organic peroxides. The curable compositions can provide flexible or rigid organic resin foam when used with a volatile organic solvent as a result of exothermic heat of cure.
    Type: Grant
    Filed: June 9, 1980
    Date of Patent: March 31, 1981
    Assignee: General Electric Company
    Inventor: James V. Crivello
  • Patent number: 4259473
    Abstract: Self-curing or curable materials are obtained from the distillation residues of coal hydrogenation by condensing a residue of this type having a softening point of 30.degree. to 54.degree. C. in a first stage with a mono- or dihydroxybenzene and/or a methylhydroxybenzene and/or an ethylene substituted benzene. These reactants are used at a ratio of residue to benzene derivative between 1:1 and 2:1 and the reaction is carried out in the presence of acid at a pH of 1 to 2 and at a temperature of 90.degree. to 100.degree. C. In a second stage the thus obtained reaction product is then further reacted at about the same temperature with an aldehyde. As a result a novolak-type resin is obtained. The invention permits the making of inexpensive self-curing or curable materials with properties similar to those of phenolic acids. Besides, the invention also provides an outlet for the high boiling residue of the extractive coal hydrogenation which otherwise had little use.
    Type: Grant
    Filed: January 15, 1980
    Date of Patent: March 31, 1981
    Assignee: Bergwerksverband GmbH
    Inventors: Ingo Romey, Menachem El-Roy
  • Patent number: 4241201
    Abstract: Phenolic novolak resins are described which are structurally characterized as having from about 55% to about 90% of the available theoretical paraphenyl linkages in the resin chain bridged to a phenyl group. The resin compositions of this invention provide extended resin stability at relatively low temperatures without significant adverse affect on the cure speed at the molding temperature. The resins are especially suited for use in runnerless injection or cold manifold molding processes, but can also be used in transfer, compression and injection molding processes.
    Type: Grant
    Filed: April 13, 1979
    Date of Patent: December 23, 1980
    Assignee: Hooker Chemicals & Plastics Corp.
    Inventor: Myron C. Annis
  • Patent number: 4239869
    Abstract: Phenolic novolak resins are described which provide extended resin stability at relatively low temperatures without significant adverse affect on the cure speed at the molding temperature. The resins are especially suited for use in runnerless injection or cold manifold molding processes, but can also be used in transfer, compression and injection molding processes.
    Type: Grant
    Filed: April 13, 1979
    Date of Patent: December 16, 1980
    Assignee: Hooker Chemicals & Plastics Corp.
    Inventor: Myron C. Annis
  • Patent number: 4218366
    Abstract: A fixing agent for improving the fastness properties of dyeings on polyamide fibers being a new condensation product of 4,4'-dihydroxydiphenylsulfone, 4,4'-dihydroxydiphenylsulfonesulfonic acid and a lower aliphatic aldehyde, which has a mean molecular weight of about 5,000 to about 30,000 and a ratio of carbon atom content and sulfur atom content of 3.0:1 to 4.8:1, or its metal salt, and when polyamide fibers are treated with the condensation product or its metal salt, or the condensation product in the presence of a salt of metal, at a temperature of 95.degree. to 120.degree. C., the fastness properties, especially wet-fastness properties of dyeings on polyamide fibers are remarkably improved.
    Type: Grant
    Filed: February 21, 1975
    Date of Patent: August 19, 1980
    Assignee: Dainippon Pharmaceutical Co., Ltd.
    Inventors: Akio Kobayashi, Yoshiyuki Shimohiro, Kisaburou Shimizu, Yoshiaki Murakami
  • Patent number: 4205135
    Abstract: A process for producing a closed cell phenolic-resin foam material comprising a phenolic-resin polymer and a surfactant which is branched, non-ionic, with a hydroxyl value less than 50 achieved by capping excess hydroxyl groups; the material, and a structural laminate employing the material. The material has a thermal conductivity which is low initially and remains low for a long period of time.
    Type: Grant
    Filed: March 18, 1976
    Date of Patent: May 27, 1980
    Assignee: The Celotex Corporation
    Inventors: John H. Beale, Ernest K. Moss
  • Patent number: 4188473
    Abstract: Polymeric materials and their thermoset, resinous products prepared by the polymerization of a mixture containing at least two different monomeric structures selected from the group having the general formula ##STR1## wherein each A represents a chalcogen independently selected from the group oxygen and sulfur; R.sub.1 represents a member selected from the group hydrogen, --CH.sub.2 (OCH.sub.2).sub.y OCH.sub.2 --R.sub.3 ; each R.sub.2 represents a member independently selected from the group consisting of R.sub.1, halogen and an alkyl group of 1 to 10 carbon atoms; R.sub.3 represents a member selected from the group consisting of H, methyl, ethyl and propyl; each m represents an independently selected integer from 1 to 2; n represents an integer from 0 to 60 and y represents an integer from 0 to 3 in the presence of an acid catalyst at a temperature of from between about 140.degree. and about 165.degree. C. for from several minutes to several hours.
    Type: Grant
    Filed: January 13, 1978
    Date of Patent: February 12, 1980
    Assignee: The Dow Chemical Company
    Inventor: Donald L. Nelson
  • Patent number: 4176216
    Abstract: The present invention provides particular phenol/formaldehyde resoles which are especially useful as foamable resins, and further provides cellular phenolic products having physical properties which are especially attractive for end-use application as construction foam. The resoles are characterized by a particular relationship between their viscosity and water content, expressed as the area bounded by certain points on a plot of resole viscosity on a logarithmic scale, as a function of water content of the resole, the particular area depending upon the mole ratio of formaldehyde-to-phenol at which the resole has been condensed. It has been found that phenol-formaldehyde resoles having the defined viscosity/water relationship are capable of providing phenolic foam having acceptable foam processability, a foam density from about 1.90 to about 3.
    Type: Grant
    Filed: September 29, 1978
    Date of Patent: November 27, 1979
    Assignee: Union Carbide Corporation
    Inventors: Wallace G. Reid, Rakesh Saini, Kenneth E. Atkins
  • Patent number: 4173551
    Abstract: Aromatic onium salts, such as diaryliodonium salts, have been found to be effective thermal initiators for the polymerization of a variety of cationically polymerizable materials including epoxides, cyclic ethers, phenol formaldehyde resins, etc., when used in combination with various cocatalysts such as organic acids and copper salts.
    Type: Grant
    Filed: December 16, 1977
    Date of Patent: November 6, 1979
    Assignee: General Electric Company
    Inventor: James V. Crivello
  • Patent number: 4168365
    Abstract: A flame-retardant phenolic resin which comprises the product obtained on(a) reacting at least one halogenated compound represented by the general formula (I) ##STR1## wherein A is --CH.dbd.CH.sub.2 or --O--CH.sub.2 --CH.dbd.CH.sub.2, X is a chlorine atom or a bromine atom, and n is an integer of 1, 2 or 3, with at least one phenol in the presence of an acidic catalyst; and(b) reacting the resulting reaction product with at least one phosphoric acid ester compound containing a phenolic OH group represented by the general formula (II), (III) or (IV). ##STR2## wherein R.sub.1, R.sub.2, R.sub.3 and R.sub.4 each represents an unsubstituted or substituted hydrocarbyl group, where R.sub.1 and R.sub.2 may be the same or different, and n is 1, 2 or 3, and at least one aldehyde or a precursor thereof in the presence of an acidic or alkali catalyst; and a process for producing the flame-retardant phenolic resin.
    Type: Grant
    Filed: November 30, 1977
    Date of Patent: September 18, 1979
    Assignee: Matsushita Electric Works, Ltd.
    Inventors: Hidekazu Takano, Toshiharu Mikawa, Kazuhiko Nemoto
  • Patent number: 4140845
    Abstract: Water-immiscible thermosetting phenol-formaldehyde resins in which a large proportion of the linkages between the benzene rings are benzyl ether linkages located ortho to the phenolic hydroxyl groups are produced by reaction of at least 1 mole of formaldehyde with 1 mole of phenol in an aqueous reaction medium in the presence of a metal carboxylate catalyst, such as, zinc acetate, in two stages, in which, in the first stage exothermic addition of formaldehyde to phenol occurs and, in the second stage, methylol phenol is polymerized to form the resin. Methods for control of the rate of polymerization, methods of separation of product resin from aqueous phase, methods of molecular weight distribution control, a semi-continuous operation and an alternative polymerization procedure are described.
    Type: Grant
    Filed: March 21, 1977
    Date of Patent: February 20, 1979
    Assignee: Cor Tech Research Ltd.
    Inventor: Ramesh C. Vasishth
  • Patent number: 4115365
    Abstract: A method for the preparation of soluble, fusible, aminomethyl diaryl compound resins in the absence of halomethylation or halomethylated materials, which method comprises (a) refluxing a mixture of diaryl compound, an aldehyde, a saturated monocarboxylic acid, and a small amount of a strong acid catalyst to form an aldehyde-diaryl resin, (b) stripping off excess monocarboxylic acid under vacuum, and then (c) adding at least about 1 mole of a primary or secondary amine containing at least one additional nontertiary amino group per reactive group on the aldehyde-diaryl resin.
    Type: Grant
    Filed: December 1, 1977
    Date of Patent: September 19, 1978
    Assignee: The Dow Chemical Company
    Inventor: Harry A. Smith
  • Patent number: 4113700
    Abstract: The invention relates to an improved process for preparing high ortho novolac resins, said process including reacting phenol and formaldehyde in the presence of a divalent electropositive metal oxide, hydroxide or organic salt wherein the improvement comprises conducting said reaction with said catalysts in combination with a divalent electropositive metal salt selected from the group consisting of sulfonates and fluoroborates or acids selected from the group consisting of sulfonic and fluoroboric or mixtures thereof.
    Type: Grant
    Filed: January 10, 1977
    Date of Patent: September 12, 1978
    Assignee: Monsanto Company
    Inventor: Harry M. Culbertson
  • Patent number: 4112160
    Abstract: Rubber cement compositions which consist of rubbers and multi- (three and more) functional phenol-aldehyde modified bifunctional phenol resins, which are made by first obtaining the bifunctional phenolic resin by condensing 1 mole of bifunctional phenol with 0.5 to 3.0 moles of aldehydes in the presence of an alkaline catalyst, and then co-condensing 0.05 to 2.5 moles of multifunctional (three and more) phenols against 1 mol of the bifunctional phenols in the above-mentioned resin in the presence of an acidic catalyst, said co-condensed resin having a number average molecular weight of 700 - 1900, a resin melting point of 80.degree. - 160.degree. C, being curable and also being soluble in aromatic hydrocarbon solvents.
    Type: Grant
    Filed: December 15, 1976
    Date of Patent: September 5, 1978
    Assignee: Sumitomo Durez Company, Ltd.
    Inventors: Yuji Kako, Toyoji Kikuga, Akira Toko