Material Contains A Sulfur Atom Patents (Class 528/90)
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Patent number: 4306953Abstract: Photopolymerizable compositions using sulfonium salt photoinitiators to effect polymerization of cationically polymerizable monomers additionally include a stable free radical to reduce or eliminate the sulfur odor generated upon photodecomposition of the sulfonium salt photoinitiator. The stable free radicals are soluble in the polymerizable material and are stable in the composition at ambient temperatures. Especially useful is 2,2-diphenyl-1-picrylhydrazyl.Type: GrantFiled: November 5, 1979Date of Patent: December 22, 1981Assignee: American Can CompanyInventor: Sheldon I. Schlesinger
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Patent number: 4307208Abstract: Thermosetting compositions comprising a film forming component bearing or capable of generating hydroxyl functionality, amine-aldehyde crosslinking agent, and a latent reactive catalyst comprising the reaction product of (i) a copolymer bearing pendent epoxy functionality, and (ii) a sulfonic acid having the formula ##STR1## wherein R is selected from linear or branched alkyl groups and aryl groups.Preferred compositions within the scope of the invention include high solids, thermosetting coating compositions suitable for automotive applications.Type: GrantFiled: January 4, 1980Date of Patent: December 22, 1981Assignee: Ford Motor CompanyInventor: Mohinder S. Chattha
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Patent number: 4302573Abstract: Novel carboxylic acid metal salt/amine complexes are prepared by reacting 1 mol of a carboxylic acid metal salt of the formula(A.sup..crclbar.).sub.2 ME.sup.2+in which A.sup..crclbar. is the anion of a carboxylic acid which contains polar substituents or radicals and in particular contains an amide or imide grouping, such as a halogenoacetic acid, nitrilo-, cyano- or ureido-acetic acid, monoamidosuccinic acid, succinimidyl- or maleimidyl-alkanecarboxylic acid, benzenesulphonic acid or pyrrolidone-5-carboxylic acid, and Me.sup.2+ is a divalent metal cation, with 1 mol of a diamine of the formulaR.sub.1 --NH--R--NH--R.sub.2in which R is an aliphatic radical having not more than 7 C atoms or is a cycloaliphatic radical and R.sub.1 and R.sub.2 are hydrogen, alkyl having 1 to 4 C atoms, cyclohexyl, benzyl, 2-aminoethyl or 3-aminopropyl, in a polar organic solvent and in the temperature range from 25.degree. to 200.degree. C., to give complex compounds.Type: GrantFiled: May 7, 1980Date of Patent: November 24, 1981Assignee: Ciba-Geigy CorporationInventors: Friedrich Stockinger, Sameer H. Eldin, Friedrich Lohse
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Patent number: 4299938Abstract: 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: GrantFiled: June 9, 1980Date of Patent: November 10, 1981Assignee: Ciba-Geigy CorporationInventors: George E. Green, Edward Irving
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Patent number: 4289595Abstract: Photopolymerizable epoxide compositions are provided which contain photoinitiators decomposable upon exposure to electromagnetic radiation to produce a Lewis acid and polymerizable epoxide compounds including an epoxide ether compound having the following general structural formula: ##STR1## wherein n equals 1-3 and wherein R is an aliphatic or cycloaliphatic group having 5-12 carbon atoms. Other epoxide compounds may be used in combination therewith to provide compositions which cure rapidly to a tack-free condition at ambient temperatures. Specific epoxide ethers disclosed are those in which n=1 and R is a group selected from the class of 2,2-dimethylpropane, 2-ethyl-1,3-hexane, 1,4-dimethylcyclohexane and 1,10-decane.Type: GrantFiled: November 26, 1979Date of Patent: September 15, 1981Assignee: American Can CompanyInventor: Anthony J. Tortorello
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Patent number: 4283312Abstract: Aromatic onium salts, such as diaryliodonium salts, have been found to be effective thermal initiators for the polymerization of epoxy resins having a viscosity of up to about 100,000 centipoises at 25.degree. C. when used in combination with copper salts. The processable epoxy resin composition can be used in filament winding and pultrusion applications.Type: GrantFiled: August 16, 1979Date of Patent: August 11, 1981Assignee: General Electric CompanyInventor: James V. Crivello
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Patent number: 4282345Abstract: A method for preparing a resinous condensation product of an allylated phenol and an ethoxyline resin comprising reacting an allylated phenol with an ethoxyline resin in the presence of an acid catalyst and a compound selected from certain ketones and esters.Type: GrantFiled: April 16, 1980Date of Patent: August 4, 1981Assignee: General Electric CompanyInventor: John D. Nelson
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Patent number: 4281075Abstract: Thermosetting compositions comprising a film forming component bearing or capable of generating hydroxyl functionality, amine-aldehyde crosslinking agent, and a latent reactive catalyst having the formula: ##STR1## wherein R is selected from alkyl or aryl groups and X is selected from 2-hydroxycycloalkyl and aryl substituted 2-hydroxycycloalkyl groups.Preferred compositions within the scope of the invention include high solids, thermosetting coating compositions suitable for automotive applications.Type: GrantFiled: January 4, 1980Date of Patent: July 28, 1981Assignee: Ford Motor CompanyInventor: Mohinder S. Chattha
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Patent number: 4276406Abstract: Catalysts for reacting vicinal epoxides with an aromatic hydroxyl-containing material result from the treatment of a solid substrate containing a plurality of ion-exchangeable cations with a polymer containing a multiplicity of quaternary onium cations in association with a reactive anion such that after treatment, there remains a sufficient quantity of the quaternary onium cations in association with the reactive anion to catalyze the reaction. These catalysts reduce the quantity of side reactions.Type: GrantFiled: April 10, 1980Date of Patent: June 30, 1981Assignee: The Dow Chemical CompanyInventors: Georgia A. Monnerat, George E. Ham, Thomas J. Hairston, Melvin J. Hatch
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Patent number: 4267087Abstract: This invention describes new perfluoroalkyl substituted esters, diesters and polyesters which contain at least one cyclic 5-membered anhydride group or two carboxy groups, as well as half amides and half esters thereof; their synthesis and their use as surface-active reactants in polycondensate resin systems.The anhydrides are synthesized by reaction of perfluoroalkyl substituted alcohols or diols with dianhydrides or an anhydrides-acid chloride and have the general structure ##STR1## wherein: Q is the tetra-radical rest of a tri- or tetra-carboxylic acid, which contains at least one 1,2-dicarboxy grouping,X is hydrogen or COOH,R.sub.f is a perfluoroalkyl or perfluoroalkoxy-perfluoroalkyl group of 4 to 18 carbon atoms,a is 1 or 2,A is hydrogen or ##STR2## wherein: m is an integer from 0 to 5, andR.sup.3 is the residue of a R.sub.f substituted alcohol or diol.Type: GrantFiled: February 16, 1979Date of Patent: May 12, 1981Assignee: Ciba-Geigy CorporationInventor: Karl F. Mueller
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Patent number: 4259454Abstract: 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: GrantFiled: June 9, 1980Date of Patent: March 31, 1981Assignee: General Electric CompanyInventor: James V. Crivello
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Patent number: 4245029Abstract: Photocurable compositions are provided based on the use of particular triarylsulfonium salts as photoinitiators for certain oxirane containing aliphatically unsaturated organic resins, such as acrylics, or mixtures of vinyl aromatic and unsaturated polyesters. A simultaneous free-radical cure and cationic cure of the aforesaid organic resins are achieved, which provides improved results, such as metal coatings having improved solvent resistance.Type: GrantFiled: August 20, 1979Date of Patent: January 13, 1981Assignee: General Electric CompanyInventor: James V. Crivello
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Patent number: 4241204Abstract: Curable organic resin compositions, such as epoxy resins, are provided, based on the use of dialkyl hydroxy arylsulfonium salts in combination with certain organic 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: GrantFiled: February 12, 1979Date of Patent: December 23, 1980Assignee: General Electric CompanyInventor: James V. Crivello
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Patent number: 4230814Abstract: Heat curable compositions are provided comprising cationically polymerizable organic materials such as epoxy resins, vinyl ethers or phenol formaldehyde resins and thermal curing agents, based on the use of dialkyl hydroxyarylsulfonium salts with an organic oxidant, such as an organic peroxide, azonitriles, etc. The heat curable compositions can be used as injection molding compounds or as a coating composition.Type: GrantFiled: February 12, 1979Date of Patent: October 28, 1980Assignee: General Electric CompanyInventor: James V. Crivello
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Patent number: 4216288Abstract: Heat curable cationically polymerizable organic materials, such as epoxy resins, are described based on the use of an aromatic onium salt initiator which can be used in combination with a reducing agent. The heat curable compositions can be used in a variety of applications, such as coating compounds, photoresists, etc.Type: GrantFiled: September 8, 1978Date of Patent: August 5, 1980Assignee: General Electric CompanyInventor: James V. Crivello
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Patent number: 4215210Abstract: A novel resin composition which is composed of molecules having an epi-bis type main skeleton of the formula ##STR1## X.sub.1 -X.sub.4 : H, Cl or Br R: H, or CH.sub.3and has a Gardner-Holdt viscosity of C to Z.sub.8 determined at 25.degree. C. for a solution in butyl carbitol in a concentration of 40% by weight.At least 40% of the entire terminal groups of the molecules of the novel composition consists of .alpha.-glycol groups of the formula ##STR2## wherein R represents hydrogen or methyl. The composition is more rapidly curable at lower temperatures than known epoxy resins having an epi-bis type main chain skeleton, and is useful as a paint or adhesive and also as an adhesion improver for other resins.Type: GrantFiled: June 9, 1978Date of Patent: July 29, 1980Assignee: Mitsubishi Petrochemical Company LimitedInventors: Kiyoaki Okayama, Yojiro Yamamoto
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Patent number: 4189544Abstract: Novel cellular and non-cellular polymers are provided in which the major recurring polymer unit is isocyanurate which polymer comprises the reaction product obtained by bringing together an aromatic polyisocyanate, a trimerization catalyst, and a minor amount of a carbamate modifier.The use of the carbamate modifier allows for the presence of high catalyst levels without shortening the reaction initiation period. At the same time, the resulting cure is very rapid and the extent of cure much deeper than has heretofore been attainable.Type: GrantFiled: February 21, 1979Date of Patent: February 19, 1980Assignee: The Upjohn CompanyInventor: Edward J. Thompson
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Patent number: 4177173Abstract: More rapid curing of polyepoxide resins is achieved by use of a curing system composed of at least one polymercaptan, at least one catalyst which is a poly[(N,N-dimethylamino)alkyl]ether and/or organic non-quaternized salts thereof derived from organic compounds having at least one acidic group and having a pKa greater than about 3.5 and, optionally, organic sulfide, tertiary phosphine or a tertiary amine having no bridged atoms, having no ether oxygen and having at least one tertiary amine group.Type: GrantFiled: December 20, 1978Date of Patent: December 4, 1979Assignee: Diamond Shamrock CorporationInventor: Brian J. Carr
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Patent number: 4173476Abstract: A triarylsulfonium complex salt is described which has particular utility as a photoinitiator for the polymerization of epoxide monomers in thick films or coatings. Photopolymerizable compositions are also described.Type: GrantFiled: February 8, 1978Date of Patent: November 6, 1979Assignee: Minnesota Mining and Manufacturing CompanyInventors: George H. Smith, Peter M. Olofson
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Patent number: 4173551Abstract: 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: GrantFiled: December 16, 1977Date of Patent: November 6, 1979Assignee: General Electric CompanyInventor: James V. Crivello
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Patent number: 4161575Abstract: This invention relates to a catalyst system comprising a triethylene diamine salt of thiocyanic acid for epoxy powder coatings, the epoxy compound having a lower softening point of not less than 40.degree. C. The catalysts for these coatings have latent activity in that they remain substantially inactive during mixing and extruding, but are highly effective at the cure temperatures.Type: GrantFiled: October 12, 1978Date of Patent: July 17, 1979Assignee: Air Products and Chemicals, Inc.Inventors: John P. Seymour, Rocco L. Mascioli, Burton D. Beitchman, Philip J. Zaluska
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Patent number: 4154872Abstract: This invention relates to a process for preparing a catalytic solution of a sulfonium salt of a complex anion, capable of yielding a Lewis Acid when irradiated by UV or high energy ionizing radiation comprising reacting a sulfonium halide with an alkali metal salt of the complex anion in a solvent mixture containing a polyol having at least two hydroxy groups and a lactone.Type: GrantFiled: May 9, 1978Date of Patent: May 15, 1979Assignee: W. R. Grace & Co.Inventors: Jung-Hsien Tsao, Arthur D. Ketley
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Patent number: 4153590Abstract: This invention describes new perfluoroalkyl substituted esters, diesters and polyesters which contain at least one cyclic 5-membered anhydride group or two carboxy groups, as well as half amides and half esters thereof; their synthesis and their use as surface-active reactants in polycondensate resin systems.The anhydrides are synthesized by reaction of perfluoroalkyl substituted alcohols or diols with dianhydrides or an anhydrides-acid chloride and have the general structure ##STR1## wherein: Q is the tetra-radical rest of a tri- or tetracarboxylic acid, which contains at least one 1,2-dicarboxy grouping,X is hydrogen or COOH,R.sub.f is a perfluoroalkyl or perfluoroalkoxyperfluoroalkyl group of 4 to 18 carbon atoms,A is 1 or 2,A is hydrogen or ##STR2## wherein: M IS AN INTEGER FROM 0 TO 5, ANDR.sup.3 is the residue of a R.sub.f substituted alcohol or diol.Type: GrantFiled: August 29, 1977Date of Patent: May 8, 1979Assignee: Ciba-Geigy CorporationInventor: Karl F. Mueller
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Patent number: 4115295Abstract: Two-part polymerizable compositions are described which contain (a) organic material having epoxide functionality, (b) organic material having hydroxyl functionality, and (c) a catalyst comprising highly fluorinated aliphatic sulfonyl protonic acid or a compound capable of liberating such acid. The compositions polymerize essentially completely at room temperature (or at slightly elevated temperatures). The polymerized compositions have desirable dielectric properties and are therefore especially useful for potting electrical components.Type: GrantFiled: April 26, 1976Date of Patent: September 19, 1978Assignee: Minnesota Mining and Manufacturing CompanyInventors: Janis Robins, James E. Kropp, Chung I. Young
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Patent number: 4110313Abstract: Epoxy resins, particularly those of the polyglycidyl ether of a polyhydric phenol type, are cured by incorporating therein a polyoxyalkylenepolyamine usually with an accelerator such as a combination of piperazine and an alkanolamine. Rapidity of curing is further improved by substituting from about 50 wt% to 100 wt% of the dithiocarbamate salt of the polyoxyalkylenepolymine for the polyoxyalkylenepolyamine. The epoxy resin products are useful in protective coatings, adhesives, seamless and terrazzo flooring, castings, laminates, and in grouting, potting, encapsulating, caulking and sealing compositions.Type: GrantFiled: July 5, 1977Date of Patent: August 29, 1978Assignee: Texaco Development CorporationInventors: Heinz Schulze, Harold G. Waddill
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Patent number: 4105667Abstract: The disclosed curing agents or initiators have the formula ML.sub.n (O--SO.sub.2 --R.sub.f).sub.m wherein L is an imidazole, M is a metal, n is a coordination number of M, R.sub.f is a fluorinated alkyl group, and m is the valence of M. These curing agents are useful in latent curable epoxy systems. Upon heating to the cure temperature (e.g. 100.degree. - 250.degree. C.), such systems cure efficiently and with a low exotherm.Type: GrantFiled: July 17, 1970Date of Patent: August 8, 1978Assignee: Minnesota Mining and Manufacturing CompanyInventor: Karl F. Thom