Polymer Mixed With Unsaturated Reactant Containing Two Or More Unsaturated Groups Patents (Class 525/44)
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Patent number: 4587293Abstract: A composition is described which thermosets when admixed with a free radical generating catalyst which composition comprises (A) an unsaturated polyester resin or vinyl ester resin, (B) a reactive monomer prepared by reacting (1) an aromatic material containing, per molecule, one polymerizable ethylenically unsaturated group and one group containing an ether linked epoxide group; and (2) a material containing at least one oxyalkylene group and is terminated in a group having at least one hydrogen atom which is reactive with an ether linked epoxide group, and (C) a polymerizable ethylenically unsaturated non-resinous monomer different from Component (B).Type: GrantFiled: January 23, 1985Date of Patent: May 6, 1986Assignee: The Dow Chemical CompanyInventor: Robert E. Hefner, Jr.
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Patent number: 4546129Abstract: New compositions of matter are disclosed which are allylated di and polycyclopentadiene diphenols. These new compositions are useful in thermoset resin compositions comprising styrene, a dicyclopentadiene-modified unsaturated polyesteramide and said allylated di and polycyclopentadiene diphenol(s).Type: GrantFiled: June 18, 1984Date of Patent: October 8, 1985Assignee: The Dow Chemical CompanyInventor: Robert E. Hefner, Jr.
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Patent number: 4540741Abstract: New unsaturated polyester resin alkyds are disclosed which have an acid number in the 30 to 60 range, viscous behavior at room temperature, a viscosity not exceeding 300,000 cps at 45.degree. C. and a viscosity not exceeding 500 cps at 25.degree. C. when diluted with styrene up to a content of 31% by weight referred to the total of alkyd plus styrene. The alkyds are obtained by reacting together compounds selected from classes including: (A) acids and unsaturated anhydrides in amounts ranging from 0.4 to 1.0 moles; (B) other dicarboxylic acids; (C) one or more polymeric glycols comprising molecules which contain more than 90% by weight of 1,2-propyleneoxide units at a rate of at least 50%, preferably 60%, moles out of the total of (C)+(D) glycols; and (D) other glycols at a rate of no more than 50% moles out of the total of C+D glycols, there being at all times present at least one component selected from class (A) and at least one component selected from class (C).Type: GrantFiled: May 23, 1984Date of Patent: September 10, 1985Inventor: Giovanni Corrado
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Patent number: 4499235Abstract: Powdery coating agent, suitable for application in the in-mould coating technique, comprising as the main component, besides a curing catalyst and if desired other additives, a crystalline unsaturated polyester with a melting point of at least 40.degree. C., a degree of unsaturation of between 1 and 5 moles unsaturation per 1000 g polyester and a viscosity in the melt at 120.degree. C. of at least 1 dPa.s.Type: GrantFiled: September 21, 1983Date of Patent: February 12, 1985Assignee: DSM Resins B.V.Inventors: Andreas N. J. Verwer, Johannes T. M. Evers
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Patent number: 4496688Abstract: Unsaturated polyester or polyesteramide compositions containing an unsaturated polyester/polyesteramide or mixture thereof, an ethylenically unsaturated monomer, and a dicyclopentadiene ester of an unsaturated polycarboxylic acid are prepared and used to cure resin compositions. The resin compositions have improved resistance to heat aging, reduced shrinkage upon curing, and improved corrosion resistance with excellent mechanical properties.Type: GrantFiled: March 21, 1983Date of Patent: January 29, 1985Assignee: The Dow Chemical CompanyInventor: Robert E. Hefner, Jr.
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Patent number: 4483963Abstract: Storage stable, polyester based compositions well adapted for hardening into molded shaped articles exhibiting virtually no shrinkage, are comprised of (i) an unsaturated polyester, (ii) a polymerizable, ethylenically unsaturated monomer copolymerizable therewith, (iii) an oligoester of the formula: ##STR1## and (iv) a condensate of such oligoester (I) with an unsaturated polyester.Type: GrantFiled: June 22, 1983Date of Patent: November 20, 1984Assignee: Chloe ChimieInventor: Jacques Meyer
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Patent number: 4461870Abstract: A high solid coating composition comprising(A) a film-forming polymer having functional group(s) capable of reacting with the crosslinking agent (D) hereinafter referred to,(B) a volatile organic liquid diluent in which the polymer (A) is carried,(C) polymer microparticles having an average diameter of from 0.02 to 40 microns, which are insoluble in the combination of the film-forming polymer (A) and the diluent (B) and are maintained in a stabilized state of dispersion therein, and(D) a crosslinking agent dissolved in the diluent (B),which is characterized in that the microparticles (C) are composed of crosslinked copolymer of .alpha.,.beta.-ethylenically unsaturated monomers carrying thereon a resinous portion having an amphoionic group of the formula: ##STR1## wherein R is a member selected from optionally substituted alkylene having 1 to 6 carbon atoms and phenylene group and Y is --COOH or --SO.sub.3 H.Type: GrantFiled: January 25, 1983Date of Patent: July 24, 1984Assignee: Nippon Paint Co., Ltd.Inventors: Kazunori Kanda, Keizou Ishii, Katsuaki Kida, Shinichi Ishikura, Ryuzo Mizuguchi
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Patent number: 4443580Abstract: The corrosion resistance of dicyclopentadiene (DCPD) modified unsaturated polyester or DCPD modified unsaturated polyesteramide resins can be improved by replacing a part of the styrene used as a reactant diluent in the resin with materials, such as divinylbenzene.Type: GrantFiled: August 25, 1982Date of Patent: April 17, 1984Assignee: The Dow Chemical CompanyInventor: Robert E. Hefner, Jr.
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Patent number: 4435530Abstract: Heat resistant resin compositions are prepared containing unsaturated polyester resins or polyesteramide resins terminated with a norbornene type group, an ethylenically unsaturated group, and a dicyclopentadiene ester of an unsaturated polycarboxylic acid.Type: GrantFiled: October 22, 1982Date of Patent: March 6, 1984Assignee: The Dow Chemical CompanyInventor: Robert E. Hefner, Jr.
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Patent number: 4430486Abstract: Ungelled reaction products of a urethane resin having acrylyl groups with an amino silane are formed. The products are capable of curing at a low temperature to form durable coatings. Polyols can optionally be blended with the ungelled reaction products to provide useful coating compositions.Type: GrantFiled: November 29, 1982Date of Patent: February 7, 1984Assignee: PPG Industries, Inc.Inventors: Wen-Hsuan Chang, Robert Piccirilli, Walter F. Kasper
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Patent number: 4420587Abstract: Phosphonopolyester oligomers are prepared from hydroxyalkylated 2,2',-bis(3-allylphenyl-4-hydroxy) alkanes and phosphonyl dihalides. The oligomers are useful in the preparation of polyester resins, epoxy resins, and polyurethanes.Type: GrantFiled: September 27, 1982Date of Patent: December 13, 1983Assignee: The Dow Chemical CompanyInventor: Robert E. Hefner, Jr.
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Patent number: 4419487Abstract: Unsaturated polyester resins are rendered less brittle without significantly deteriorating other physical properties by reacting therewith 0.1 to 25 parts of a carboxyl terminated reactive liquid polymer, preferably poly(butadiene-acrylonitrile), per 100 parts of the polyester resin.Type: GrantFiled: April 22, 1982Date of Patent: December 6, 1983Assignee: The B. F. Goodrich CompanyInventor: Eugene H. Rowe
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Patent number: 4389512Abstract: Cycloalphatic acrylate compositions and methods of making them are disclosed. The compositions are mixtures containing dicyclopentadiene (meth) acrylate and (meth) acrylates such as the mono and di (meth) acrylates of tri, and tetracyclopentadiene and a mixture of the copolymers of (meth) acrylic acid with adducts of cyclopentadiene with isoprene and/or piperylene and a mixture of poly (meth) acrylates having the repeating unit ##STR1## where R.sup.1 is hydrogen or ##STR2## R.sup.2 is CH.sub.2 .dbd.CZ--C(O)--O-- Z is H, or methyln is 0, 1 or 2 andm is 0 or 1 and when m is 0 there isa double bond present.The compositions are useful to make crosslinkable blends with unsaturated resins or monomers and to make laminates.Type: GrantFiled: May 29, 1981Date of Patent: June 21, 1983Assignee: The Dow Chemical Co.Inventors: Hans R. Friedli, Donald L. Nelson, John L. Massingill, Jr.
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Patent number: 4387182Abstract: Cycloalphatic acrylate compositions and methods of making them are disclosed. The compositions are mixtures containing dicyclopentadiene (meth) acrylate and (meth) acrylates such as the mono and di (meth) acrylates of tri, and tetracyclopentadiene and a mixture of the copolymers of (meth) acrylic acid with adducts of cyclopentadiene with isoprene and/or piperylene and a mixture of poly (meth) acrylates having the repeating unit ##STR1## where R.sup.1 is hydrogen or ##STR2## R.sup.2 is CH.sub.2 .dbd.CZ--C(O)--O-- Z is H, or methyln is 0, 1 or 2 andm is 0 or 1 and when m is 0 there is a double bond present.The compositions are useful to make cross-linkable blends with unsaturated resins or monomers and to make laminates.Type: GrantFiled: May 29, 1981Date of Patent: June 7, 1983Assignee: The Dow Chemical Co.Inventors: Hans R. Friedli, Donald L. Nelson, John L. Massingill, Jr.
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Patent number: 4385154Abstract: Novel thermosetting compositions, including a polyimide/N-vinylpyrrolidone prepolymer, optionally comprising an unsaturated polyester, and an epoxy resin, are well adapted for the molding of a variety of useful shaped articles.Type: GrantFiled: October 15, 1981Date of Patent: May 24, 1983Assignee: Rhone-Poulenc IndustriesInventors: Robert Cassat, Gerard Guillot
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Patent number: 4379039Abstract: An ultraviolet curable resin composition comprising(I) a saturated copolyester having a molecular weight of 2,000 to 15,000 which is soluble in a polymerizable compound (II), 20% by mole or more of saturated polycarboxylic acid components of the saturated copolyester being an aromatic dicarboxylic acid,(II) a polymerizable compound, at least a part of which is a compound having two or more polymerizable double bonds in the molecule thereof, and(III) a photosensitizer.The ultraviolet curable resin composition has excellent flexibility, adhesion and processability and is useful as an ink composition for screen printing and a transfer paper for decorating potteries and further as an adhesive for the preparation of laminated products.Type: GrantFiled: December 24, 1980Date of Patent: April 5, 1983Assignee: Toyo Boseki Kabushiki KaishInventors: Hiroshi Fujimoto, Hideo Miyake
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Patent number: 4367308Abstract: A cross linked graft polyester comprising the reaction product of a mixture of a polyunsaturated vinyl monomer with an acidic monovinyl monomer having at least one carboxyl group with an unsaturated polyester.Type: GrantFiled: December 5, 1980Date of Patent: January 4, 1983Assignee: BASF Wyandotte CorporationInventor: Robert B. Login
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Patent number: 4362848Abstract: Cycloalphatic acrylate compositions and methods of making them are disclosed. The compositions are mixtures containing dicyclopentadiene (meth) acrylate and (meth) acrylates such as the mono and di (meth) acrylates of tri, and tetracyclopentadiene and a mixture of the copolymers of (meth) acrylic acid with adducts of cyclopentadiene with isoprene and/or piperylene and a mixture of poly (meth) acrylates having the repeating unit ##STR1## Where R.sup.1 is hydrogen or ##STR2## R.sup.2 is CH.sub.2 .dbd.CZ--C(O)--O-- Z is H, or methyln is 0, 1 or 2 andm is 0 or 1 and when m is 0 there isa double bond present.The compositions are useful to make cross-linkable blends with unsaturated resins or monomers and to make laminates.Type: GrantFiled: May 29, 1981Date of Patent: December 7, 1982Assignee: The Dow Chemical Co.Inventors: Hans R. Friedli, Donald L. Nelson, John L. Massingill, Jr.
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Patent number: 4360634Abstract: Polyester resins are prepared by reacting unsaturated dicarboxylic acid anhydrides with water, a diene oligomer, and a polyol or and an alkylene oxide. The polyester resins can be blended with unsaturated monomers and various fiber to give cured laminates. The advantage of this invention is that the substitution of the diene oligomers gives lower cost resins with about the same properties.Type: GrantFiled: September 8, 1981Date of Patent: November 23, 1982Assignee: The Dow Chemical CompanyInventor: Donald L. Nelson
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Patent number: 4351919Abstract: Polyester silicate resinous products are produced by chemically reacting an organosol containing organic polyhydroxy compounds with an organic polycarboxylic acid and/or polycarboxylic acid anhydride. An excess of oxidated silicon compound may be used in this process. The unsaturated polyester silicate resinous products may be used to produce building panels, boats, furniture, etc.Type: GrantFiled: October 13, 1981Date of Patent: September 28, 1982Inventor: David H. Blount
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Patent number: 4345048Abstract: Brominated cycloaliphatic (meth) acrylate compositions are prepared by the reaction of bromine at a temperature in the range from -30.degree. C. to 50.degree. C. with compositions made by reacting (meth) acrylic acid with dicyclopentadiene compositions in the presence of a Friedel-Crafts catalyst such as BF.sub.3.The brominated compositions are useful to make copolymers which find use as metal coatings, laminates, ultraviolet light curable coatings and the like.Type: GrantFiled: January 21, 1980Date of Patent: August 17, 1982Assignee: The Dow Chemical CompanyInventors: Hans R. Friedli, Clinton J. Boriack
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Patent number: 4336349Abstract: Chlorinated cycloaliphatic (meth) acrylate compositions are prepared by the reaction of chlorine at a temperature in the range from -30.degree. C. to 50.degree. C. with compositions made by reacting (meth) acrylic acid with crude dicyclopentadiene in the presence of a Friedel-Crafts catalyst such as BF.sub.3. The chlorinated compositions have a pleasant fruity odor and are useful to make homopolymers or copolymers which find use as metal coatings, inks, ultraviolet light curable coatings and the like.Type: GrantFiled: December 22, 1980Date of Patent: June 22, 1982Assignee: The Dow Chemical CompanyInventors: Hans R. Friedli, Clinton J. Boriack
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Patent number: 4336344Abstract: The stability to phase separate solutions of unsaturated polyesters, vinyl ester resins or mixtures thereof and an elastomeric additive is improved by the use of a compatibilizing agent which is the ester of a carboxyl terminated diene polymer and a polyoxyalkylene.Type: GrantFiled: August 24, 1981Date of Patent: June 22, 1982Assignee: The Dow Chemical CompanyInventor: Laurence J. Craigie
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Patent number: 4324934Abstract: The 1:1-adduct of 1.3-butadiene and dicyclopentadiene is an excellent reactive thinner for air-drying lacquers.Type: GrantFiled: January 9, 1981Date of Patent: April 13, 1982Assignee: Bayer AktiengesellschaftInventors: Erich Eimers, Rolf Dhein
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Patent number: 4322505Abstract: A reactive polyester resin composition comprising a polyester resin having ethylenically unsaturated terminal groups, and a reactive, aliphatic plasticizer compatible with the resin and having ethylenically unsaturated terminal groups. By virtue of the terminal ethylenic unsaturation, the composition can be cross-linked with, e.g., styrene to form a tough, flexibilized, corrosion resistant polymer. The high level of corrosion resistance is maintained notwithstanding the impressive degree of flexibility imparted to the composition.Type: GrantFiled: October 20, 1980Date of Patent: March 30, 1982Assignee: Phillips Petroleum CompanyInventor: Eugene F. Jacobs
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Patent number: 4319009Abstract: Cycloalphatic acrylate compositions and methods of making them are disclosed. The compositions are mixtures containing dicyclopentadiene (meth) acrylate and (meth) acrylates such as the mono and di (meth) acrylates of tri, and tetracyclopentadiene and a mixture of the copolymers of (meth) acrylic acid with adducts of cyclopentadiene with isoprene and/or piperylene and a mixture of poly (meth) acrylates having the repeating unit ##STR1## where R.sup.1 is hydrogen or ##STR2## R.sup.2 is CH.sub.2 .dbd.CZ-C(O)--O-- Z is H, or methyln is 0, 1 or 2 andm is 0 or 1 and when m is 0 there isa double bond present.The compositions are useful to make crosslinkable blends with unsaturated resins or monomers and to make laminates.Type: GrantFiled: October 13, 1978Date of Patent: March 9, 1982Assignee: The Dow Chemical CompanyInventors: Hans R. Friedli, Donald L. Nelson, John L. Massingill, Jr.
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Patent number: 4296020Abstract: Ethylenically unsaturated monomer solutions of ethylenically unsaturated polyester, polyester urethane and polyisocyanurate resins are quickly converted to moldable gels by the homogeneous formation therein of polyurea resins by the interaction of polyamines and polyisocyanates. Tack-free handleable moldable gels are formed within minutes which can be stored under normal conditions for long periods of time until molded. Fully cured intractable articles are formed by the polymerization of the ethylenically unsaturated ingredients.Type: GrantFiled: October 29, 1979Date of Patent: October 20, 1981Assignee: ICI Americas Inc.Inventor: Juan J. Magrans, Jr.
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Patent number: 4287313Abstract: A thermosettable composition comprising (1) an unsaturated polyester, (2) a block copolymer of a lactone, a conjugated diene and, optionally, a monovinylarene, and (3) a vinyl monomer is provided which shows improved compatibility and stability over a composition in which the block copolymer does not contain a polylactone block.Type: GrantFiled: April 4, 1979Date of Patent: September 1, 1981Assignee: Phillips Petroleum Co.Inventors: Raymond F. Uber, Clifford W. Childers, Floyd E. Naylor
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Patent number: 4287310Abstract: A thermosetting powder based on a homogeneous mixture containing 50 to 92% by weight of an unsaturated polyester resin having a softening temperature of at least 50.degree. C. 50 to 30% bij weight of a prepolymer of a diallylester of an aromatic dicarboxylic acid, 3 to 20% by weight of a high boiling, crosslinking monomer and 0.1 to 5% by weight of hardening catalyst, all weight percentages relating to the overall quantity of the polymerizable components.A process for the preparation of the thermosetting powder by melting and mixing the polyester resin and at least the greater part of the other polymerizable components except the catalyst subsequently the catalyst and the remaining portion of the polymerizable components is rapidly admixed to the melt at a temperature that is at least 20.degree. lower than the temperature corresponding to a half life time of 1 minute in which operation the time during which the catalyst is exposed to the higher temperature is max. 30 sec.Type: GrantFiled: April 24, 1980Date of Patent: September 1, 1981Assignee: Stamicarbon, B.V.Inventor: Rene L. E. van Gasse
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Patent number: 4274994Abstract: Terminally unsaturated liquid epihalohydrin polymers are produced by polymerizing at least one epihalohydrin using acrylic acid or methacrylic acid as a modifier. The polymerization is conducted in the presence of a catalytic amount of a trialkyl oxonium salt of an HMF.sub.6 acid wherein M is an element selected from the group consisting of phosphorus, arsenic and antimony. The polymers are useful as tougheners for unsaturated polyester resin systems.Type: GrantFiled: June 13, 1980Date of Patent: June 23, 1981Assignee: The B. F. Goodrich CompanyInventor: Changkiu K. Riew
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Patent number: 4274992Abstract: Polyester resins are formed by the reaction of alcohols having a hydroxyl functionality of at least one and an allyloxy functionality of at least one, provided the total hydroxyl and allyloxy functionalities are at least three, with saturated dicarboxylic acids or anhydrides. The polyester resins are combined with vinyl monomers to form low temperature cure coating compositions.Type: GrantFiled: December 11, 1979Date of Patent: June 23, 1981Assignee: PPG Industries, Inc.Inventors: Peter R. Buechler, Earl E. Parker, Kenneth L. Mollohan
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Patent number: 4268431Abstract: A colorant-thickener dispersion for unsaturated polyester resin compositions comprises(a) 20% to 50% by weight of a thickener comprising a Group II-A metal oxide or hydroxide,(b) 5% to 20% by weight of a pigment component, and(c) 30% to 75% by weight of an unsaturated polyester vehicle that comprises(1) 50% to 100% by weight of at least one unsaturated polyester that is the product of the reaction of a dicarboxylic acid component containing 80 to 90 mole % of at least one unsaturated aliphatic dicarboxylic acid having 4 to 8 carbon atoms and 10 to 20 mole % of at least one saturated aromatic dicarboxylic acid with an alcohol component containing 40 to 60 mole % of at least one glycol having 2 to 6 carbon atoms and 40 to 60 mole % of at least one monohydric alcohol having 6 to 12 carbon atoms, in the amount of 0.4 mole to 0.Type: GrantFiled: June 1, 1979Date of Patent: May 19, 1981Assignee: Tenneco Chemicals, Inc.Inventors: Martin L. Feldman, James T. De Groff
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Patent number: 4263198Abstract: A thickening agent for unsaturated polyester resin compositions comprises(a) 25% to 70% by weight of a Group II-A metal oxide or hydroxide and(b) 30% to 75% by weight of an unsaturated polyester vehicle comprising(1) 50% to 100% by weight of an unsaturated polyester that is the product of the reaction of a dicarboxylic acid component that contains at least one unsaturated aliphatic dicarboxylic acid and at least one saturated aromatic dicarboxylic acid with an alcohol component that contains at least one glycol and at least one monohydric alcohol and(2) 0-50% by weight of an unsaturated monomer capable of reacting with the unsaturated polymer to form cross-linkages.Type: GrantFiled: June 1, 1979Date of Patent: April 21, 1981Assignee: Tenneco Chemicals, Inc.Inventors: Martin L. Feldman, James T. De Groff
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Patent number: 4216134Abstract: Single component, shelf stable, anaerobic curing, adhesive compositions displaying high strength and resistance to water, heat and radiation are produced using triallylcyanurate or triallylisocyanurate as a reaction component.Type: GrantFiled: October 12, 1977Date of Patent: August 5, 1980Inventor: Walter Brenner
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Patent number: 4213889Abstract: Diallyl maleate in combination with alkyl phosphates, including mixed alkyl aryl phosphates, when added to styrene-unsaturated polyester resin systems and cured with a free-radical forming initiator provides a high level of flame resistance.Type: GrantFiled: February 13, 1979Date of Patent: July 22, 1980Assignee: FMC CorporationInventor: Harry H. Beacham
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Patent number: 4205139Abstract: Curable coating compositions of olefinically unsaturated compounds A and an N-vinyl compound B. The N-vinyl compounds carry at least 2 N-vinyl groups and at least one carbonyl group bonded to the nitrogen of the N-vinyl group. The coating compositions can be used for the manufacture of paints, printing inks, printing plates and photoresist materials.Type: GrantFiled: July 28, 1977Date of Patent: May 27, 1980Assignee: BASF AktiengesellschaftInventors: Helmut Barzynski, Heinrich Hartmann, Dieter Lautenbach, Rolf Osterloh, Lutz Goethlich, Guenter Heil
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Patent number: T101903Abstract: Free radical promoters for use in curing resin compositions comprising an unsaturated polyester and an ethylenically unsaturated copolymerizable monomer are disclosed for use with conventional initiators. The free radical promoters comprise ferrocene or ferrocene substituted on one or both cyclopentadienyl rings with an alkyl, alkoxy, hydroxyl, carboxyl, carboxaldehyde, hydroxyalkyl, amino, halo, cycloalkyl, or aryl radical.Type: GrantFiled: April 24, 1981Date of Patent: June 1, 1982Inventor: John R. Dombroski
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Patent number: RE31577Abstract: Terminally unsaturated liquid epihalohydrin polymers are produced by polymerizing at least one epihalohydrin using acrylic acid or methacrylic acid as a modifier. The polymerization is conducted in the presence of a catalytic amount of a trialkyl oxonium salt of an HMF.sub.6 acid wherein M is an element selected from the group consisting of phosphorus, arsenic and antimony. The polymers are useful as tougheners for unsaturated polyester resin systems.Type: GrantFiled: June 21, 1983Date of Patent: May 1, 1984Assignee: The B. F. Goodrich CompanyInventor: Changkiu K. Riew