Material Contains A Heavy Metal Atom Containing Organic Compound Patents (Class 526/192)
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Patent number: 4429092Abstract: A composition for preparing polymeric articles comprising: (a) an acrylic polymerizable component such as monomeric and polymeric aliphatic acrylate and methacrylate esters having a Brookfield viscosity of about 0.1-400 poise and about 5-60% by weight of solids; (b) copper and tin polymerization promoters providing in the composition about 0.05-4 ppm of Cu.sup.+2 and about 10-300 ppm of Sn.sup.+2 ; (c) about 5.times.10.sup.-6 to 1.times.10.sup.-4 mole/gm of the composition of a primary mercaptan chain transfer agent; and (d) sufficient peroxyester initiator to provide about 0.02-0.3% by weight of active oxygen in the composition. The composition is highly efficient at room temperature and provides excellent optical quality polymers while permitting a wide choice of peroxyesters as the initiator.Type: GrantFiled: December 6, 1982Date of Patent: January 31, 1984Assignee: U.S. Peroxygen CompanyInventor: Gary P. Sterling
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Patent number: 4398014Abstract: 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: GrantFiled: October 23, 1981Date of Patent: August 9, 1983Assignee: Ciba-Geigy CorporationInventors: George E. Green, Edward Irving, Bernard P. Stark
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Patent number: 4394466Abstract: A binder composition which contains certain fulvenes and/or prepolymers thereof, and a metal salt catalyst.Type: GrantFiled: November 10, 1981Date of Patent: July 19, 1983Assignee: Ashland Oil, Inc.Inventors: Bruce A. Gruber, Heimo J. Langer, William R. Dunnavant
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Patent number: 4389514Abstract: A method of increasing the reaction rate of the polymerization and/or cross-linking of reactive polymerizable and/or cross-linkable acrylic monomeric materials initiated by dialkyl or diaralkyl peroxides as the free radical generator which comprises carrying out such a polymerization and/or cross-linking reaction in the presence of a member of the group consisting of stannous alkanoates, alkenoates, aralkanoates and aralkenoates, dialkyl tin dialkanoates, dialkenoates, diaralkanoates and diaralkenoates, or mixtures thereof in various proportions.Type: GrantFiled: December 7, 1981Date of Patent: June 21, 1983Assignee: Congoleum CorporationInventors: Claude J. Schmidle, Seevaram N. Varadhachary
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Patent number: 4382130Abstract: Certain aryloxyphosphonium salts have been found to be effective as curing agents for various cationically polymerizable organic materials, such as epoxy resins, when incorporated into such materials. The materials are found to be moisture curable coating compositions.Type: GrantFiled: October 14, 1981Date of Patent: May 3, 1983Assignee: General Electric CompanyInventors: Robert H. Ellison, Martin A. Byrne
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Patent number: 4339567Abstract: 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: GrantFiled: February 23, 1981Date of Patent: July 13, 1982Assignee: Ciba-Geigy CorporationInventors: George E. Green, Edward Irving
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Patent number: 4336366Abstract: 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: GrantFiled: February 20, 1981Date of Patent: June 22, 1982Assignee: Ciba-Geigy CorporationInventors: Godwin Berner, Rudolf Kirchmayr
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Patent number: 4336363Abstract: 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 certain aryl sulfonium 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: October 9, 1980Date of Patent: June 22, 1982Assignee: General Electric CompanyInventor: James V. Crivello
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Patent number: 4320218Abstract: A binder composition which contains certain fulvenes and/or prepolymers thereof, and a metal salt catalyst.Type: GrantFiled: August 4, 1980Date of Patent: March 16, 1982Assignee: Ashland Oil, Inc.Inventors: Bruce A. Gruber, Heimo J. Langer, William R. Dunnavant
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Patent number: 4316835Abstract: This invention involves a curable liquid mixture comprising (a) a polyester of the following formula: ##STR1## wherein n has an average value between about 1.Type: GrantFiled: April 16, 1980Date of Patent: February 23, 1982Assignee: Union Carbide CorporationInventor: Hugh C. Gardner
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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: 4296214Abstract: A methacrylic resin having a high solar radiant energy absorbing property wherein an organic compound (A) containing cupric ion and a compound (B) having at least one P-O-H bond in a molecule are contained into the methacrylic resin selected from poly(methyl methacrylate) or methacrylic polymers containing at least 50% by weight of a methyl methacrylate unit. A process for producing said methacrylic resin is also disclosed.Type: GrantFiled: April 11, 1980Date of Patent: October 20, 1981Assignee: Mitsubishi Rayon Co., Ltd.Inventors: Kazumasa Kamada, Yoshio Nakai, Kazunori Abe
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Patent number: 4293675Abstract: The complex formed between a tri-or pentavalent antimony halide and an organic phosphate ester has been found to be an effective catalyst for cationic polymerization reactions.Type: GrantFiled: February 26, 1980Date of Patent: October 6, 1981Assignee: Minnesota Mining and Manufacturing CompanyInventors: Robert J. Blachunis, Stephen W. Bany
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Patent number: 4292419Abstract: A radiation-shielding plastic material having an excellent transparency and superior mechanical properties, is produced by polymerizing, in the presence of a lead compound, a mixture of a vinyl monomer component (A) consisting of at least one member selected from alkyl methacrylates and acrylates, hydroxyalkyl methacrylates and acrylates and styrene and an organic acid component (B) containing, as an indispensable ingredient, at least one member selected from the compounds of the formulae (I) through (IV): ##STR1## wherein R.sub.1 =C.sub.1-10 hydrocarbon radical, R.sub.2 =C.sub.1-7 hydrocarbon radical, R.sub.3 and R.sub.4 =H or CH.sub.3, R.sub.5 =C.sub.2-7 hydrocarbon radical, R.sub.6 =C.sub.1-3 hydrocarbon radical and n=0.about.4.Type: GrantFiled: April 24, 1980Date of Patent: September 29, 1981Assignee: Mitsubishi Rayon Co., Ltd.Inventors: Kazumasa Kamada, Kazuya Okada
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Patent number: 4291145Abstract: The complex formed between a pentavalent antimony halide and an organic phosphate ester has been found to be an effective catalyst for cationic polymerization reactions.Type: GrantFiled: February 26, 1980Date of Patent: September 22, 1981Assignee: Minnesota Mining and Manufacturing CompanyInventors: Robert J. Balchunis, Stephen W. Bany
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Patent number: 4269957Abstract: A process for the bulk or suspension polymerization of vinyl monomers, particularly vinyl chloride, in the presence of a redox catalyst system consisting of a peroxyester or diacyl peroxide and a stannous or antimony (III) carboxylate.Type: GrantFiled: December 21, 1979Date of Patent: May 26, 1981Assignee: Dart Industries Inc.Inventors: Norman G. Gaylord, Meshulam Nagler, Marvin M. Fein
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Patent number: 4269958Abstract: A process for the suspension polymerization of vinyl chloride, in the presence of a redox catalyst system consisting of a peroxyester or diacyl peroxide and stannous chloride.Type: GrantFiled: December 21, 1979Date of Patent: May 26, 1981Assignee: Dart Industries Inc.Inventor: N. Grant Gaylord
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Patent number: 4269956Abstract: A process for the bulk or suspension polymerization of vinyl chloride, in the presence of a redox catalyst system consisting of a peroxyester or diacyl peroxide, a stannous or antimony (III) carboxylate and a complexing agent.Type: GrantFiled: December 21, 1979Date of Patent: May 26, 1981Assignee: Dart Industries Inc.Inventors: Norman G. Gaylord, Meshulam Nagler
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Patent number: 4242482Abstract: A process for the bulk or suspension polymerization of vinyl chloride or vinylidene chloride, in the presence of a redox catalyst system consisting of a peroxyester or a diacyl peroxide and a stannous or antimony (III) mercaptide.Type: GrantFiled: December 21, 1979Date of Patent: December 30, 1980Assignee: Dart Industries Inc.Inventors: Norman G. Gaylord, Meshulam Nagler, Marvin M. Fein
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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: 4238587Abstract: 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. Among the cocatalysts which have been found to be effective are, for example, copper chelates and mixtures of such copper chelates with various reducing agents such as ascorbic acid, tin.sup.+2 salts, etc.Type: GrantFiled: November 28, 1979Date of Patent: December 9, 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: 4229559Abstract: This invention is directed to a half ester characterized by the following empirical formula: ##STR1## wherein n is a number having an average value of 1.7 to 2, and m is equal to 2-n. Also described herein is a composition comprising said half ester, maleic anhydride and an ethylenically unsaturated monomer, wherein at least 75 mole percent of the half ester is in the maleate form.Type: GrantFiled: May 1, 1979Date of Patent: October 21, 1980Assignee: Union Carbide CorporationInventors: Robert J. Cotter, Hugh C. Gardner
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Patent number: 4225691Abstract: Low temperature curable organic resin compositions, for example, epoxy resins are provided, which can be either exothermically cured or cured in several minutes or less at relatively low temperatures. Certain diaryliodonium salts have been found to spontaneously release strong protonic acids when used in combination with a copper salt and a reducing agent.Type: GrantFiled: July 17, 1979Date of Patent: September 30, 1980Assignee: General Electric CompanyInventor: James V. Crivello
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Patent number: 4197215Abstract: In the use of certain metal salts of the hemi-perester of maleic acid as catalysts for the polymerization and curing of ethylenically unsaturated monomers and of methyl methacrylate-containing syrups the addition of an activator such as sodium bisulfite provides a substantial reduction in the curing time. The process is relatively insensitive to the amount of filler used.The salts of maleic hemi-peresters, in combination with the activators, are also useful for polymerizing ethylenically unsaturated monomers.Type: GrantFiled: May 25, 1978Date of Patent: April 8, 1980Assignee: E. I. Du Pont de Nemours and CompanyInventor: Ronald S. Dudinyak
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Patent number: 4182821Abstract: A method for producing a lead containing monomer composition comprising reacting a mixture comprising (1) at least one monomer selected from the group consisting of alkyl methacrylate having 1-4 carbon atoms in an alkyl group, hydroxyalkyl acrylate, hydroxyalkyl methacrylate and styrene, (2) acrylic or methacrylic acid, (3) an organic acid having the general formula: R.sub.1 COOH, wherein R.sub.1 is hydrocarbon residue having 5-20 carbon atoms and optionally (4) an organic acid having the general formula: R.sub.2 COOH, wherein R.sub.2 is hydrocarbon residue having 2-4 carbon atoms with lead monoxide. The composition is polymerized to obtain a radiation shielding polymer.Type: GrantFiled: November 14, 1977Date of Patent: January 8, 1980Assignee: Kyowa Gas Chemical Industry Co., Ltd.Inventors: Haruo Nagai, Hiroshi Uehara, Kunikazu Nunokawa
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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: 4161571Abstract: A process for production of the maleic anhydride adduct of a liquid polymer having a maleic anhydride addition amount of 2 to 70% by weight, which comprises reacting a liquid polymer having a molecular weight of 150 to 5,000 and a viscosity of 2 to 50,000 cp at 30.degree. C. in the presence of at least one compound, as a gelation inhibitor, selected from the group consisting of imidazoles, thiazoles, metallic salts of mercaptothiazoles, urea derivatives, naphthylamines, nitrosamines, iron, iron compounds and specific halogen compounds, said liquid polymer being selected from the group consisting of liquid polybutadienes, liquid polyisoprenes and liquid copolymers comprising units of butadiene or isoprene and units of at least one compound selected from the group consisting of other diolefins, olefins and aromatic vinyl compounds.Type: GrantFiled: October 18, 1977Date of Patent: July 17, 1979Assignee: Sumitomo Chemical Company, LimitedInventors: Seimei Yasui, Takao Oshima
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Patent number: 4129524Abstract: A radiation shielding material of a composition containing a polymer comprising (A) at least one essential monomer selected from the group consisting of alkyl methacrylate having 1 - 4 carbon atoms in an alkyl group, hydroxyalkyl acrylate, hydroxyalkyl methacrylate and styrene and (B) lead acrylate or lead methacrylate, and a lead carboxylate represented by the general formula: (RCOO).sub.a Pb, a being an integer equal to the valency of lead and R representing a saturated or unsaturated hydrocarbon residue having 5 - 20 carbon atoms, wherein the ratio x (% by weight) of the lead acrylate or lead methacrylate to the total constituent monomer in the polymer and the compounding ratio y (parts by weight) of the lead carboxylate to 100 parts by weight of said total monomer in said composition satisfy any one of the following three formulas I, II and III:200.gtoreq.y.gtoreq.2, where 9.ltoreq.x.ltoreq.30 (I)200.gtoreq.y.gtoreq.2/5(x - 30)+ 2, where 30.ltoreq.x.ltoreq.75(II) and200.gtoreq.y.gtoreq.Type: GrantFiled: July 13, 1977Date of Patent: December 12, 1978Assignee: Kyowa Gas Chemical Industry Co., Ltd.Inventors: Haruo Nagai, Hiroshi Uehara, Kunikazu Nunokawa
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Patent number: 4115318Abstract: An olefin polymerization catalyst is prepared by depositing a poly (di-.mu.-dihydrocarbylphosphinatohydroxyaquochromium (III)) compound or the corresponding anhydrous compound upon an inorganic support material and calcining the impregnated support material in a non-reducing atmosphere above 300.degree. C. up to the decomposition temperature of the support material to provide an activated catalyst. The catalyst exhibits high productivity and produces polymers having high melt indices.Type: GrantFiled: June 9, 1977Date of Patent: September 19, 1978Assignee: National Petro Chemicals CorporationInventor: Anthony N. Speca
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Patent number: 4091197Abstract: Micro-suspension polymerization of vinyl chloride monomers and comonomers with a seed in the form of a previously prepared dispersion of the polymer or copolymer containing all of the organo-soluble initiator required for the polymerization, in which the initiator is activated during the polymerization by the addition of an organo-metallic complex of a water-soluble metal salt reacted with a complexing agent.Type: GrantFiled: December 5, 1975Date of Patent: May 23, 1978Inventors: Nicolas Fischer, Jacques Boissel, Thomas Kemp, Henri Eyer
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Patent number: 4080493Abstract: A process for production of the maleic anhydride adduct of a liquid polymer having a maleic anhydride addition amount of 2 to 70% by weight, which comprises reacting a liquid polymer having a molecular weight of 150 to 5,000 and a viscosity of 2 to 50,000 cp at 30.degree. C in the presence of at least one compound, as a gelation inhibitor, selected from the group consisting of imidazoles, thiazoles, metallic salts of mercaptothiazoles, urea derivatives, naphthylamines, nitrosamines, iron, iron compounds and specific halogen compounds, said liquid polymer being selected from the group consisting of liquid polybutadienes, liquid polyisoprenes and liquid copolymers comprising units of butadiene or isoprene and units of at least one compound selected from the group consisting of other diolefins, olefins and aromatic vinyl compounds.Type: GrantFiled: October 19, 1976Date of Patent: March 21, 1978Assignee: Sumitomo Chemical Company, LimitedInventors: Seimei Yasui, Takao Oshima
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Patent number: 4031036Abstract: Bis(fluoroaliphaticsulfonyl)imides, in active or latent form, are used as catalysts for the polymerization of cationic sensitive monomers, e.g., epoxy resins.Type: GrantFiled: June 9, 1975Date of Patent: June 21, 1977Assignee: Minnesota Mining and Manufacturing CompanyInventor: Robert J. Koshar
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Patent number: 3997707Abstract: A method of suspension polymerization, which is effective to prevent the adhesion of scale-form polymer to the inside wall of polymerization vessel, is provided by adding oxalic acid or its salt to the polymerization system consisting of vinyl chloride suspended in aqueous medium.Type: GrantFiled: April 25, 1975Date of Patent: December 14, 1976Assignee: Chisso CorporationInventors: Shiro Aruga, Kazuaki Nakano, Seigo Ishibashi
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Patent number: 3985718Abstract: Four component polymerization initiators for olefinic monomers comprise (1) an oxidizing agent such as hydrogen peroxide, a persulphate, a permanganate, a chlorate, a perchlorate, a bichromate, a bromate, a ceric salt, an oxazirane, an organic peroxide or an organic hydroperoxide, (2) a chelate compound of a metal such as titanium, iron, vanadium, aluminum, tin, manganese, chromium, cobalt, copper, zinc or bismuth in which the metal is not fully coordinated, (3) an electron donor in amount at most equal to that required to complex completely the said metal of the chelate compound, the said electron donor being for example an amine, a monoalcohol, an ether, an aldehyde, a ketone, an imine, an oxime, an amide, a sulphonamide, or a phosphonamide, and (4) a chelate complex or salt which is different from the chelate compound (2) and in which the metal may be for example, copper, iron, magnesium, manganese, chromium, vanadium or tin, the degree of coordination of the said metal being different from that of the metType: GrantFiled: August 5, 1974Date of Patent: October 12, 1976Assignee: Rhone-Poulenc S.A.Inventors: Henri Chabert, Robert Chapurlat, Claude Gigou, Michel Ruaud
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Patent number: 3970612Abstract: Vinyl halide homopolymers, copolymers and graft polymers of substantially lower molecular weight are obtained when polymerization is carried out in the presence of an organotin mercaptide ester and an organic azo initiator. The products are faster fusing and have lower melt viscosities than corresponding polymers of the same molecular weight prepared by high temperature molecular weight reduction methods. The low molecular weight and excellent fusion characteristics of the products render these polymers particularly useful in molding, extrusion, and coating applications.Type: GrantFiled: December 30, 1974Date of Patent: July 20, 1976Assignee: Hooker Chemicals & Plastics CorporationInventor: Gilbert Witschard
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Patent number: 3966573Abstract: A photopolymerization co-initiator system comprises (a) about 1-30 parts of at least one carbonyl-containing compound, (b) about 1-30 parts of an organic compound containing nitrogen, phoshorus, arsenic, bismuth, or antimony, and (c) about 1-30 parts of at least one halogenated hydrocarbon.Type: GrantFiled: July 23, 1975Date of Patent: June 29, 1976Assignee: Sun Chemical CorporationInventor: Anthony J. Bean