Polymer Mixed With Unsaturated Reactant Containing Carboxylic Acid, Ester, Salt Or Anhydride Group Patents (Class 525/39)
-
Patent number: 4370447Abstract: An unsaturated polyester was obtained by reacting a polyhydric alcohol with a mixture of an unsaturated polybasic acid and a specific saturated dibasic acid represented by the formula: ##STR1## or the formula: ##STR2## wherein, R.sub.1 to R.sub.10 are each hydrogen or alkyl, R' to R"" are the same or different and each represent hydrogen or ester-exchangeable alkyl, m is 1 or 2, and n is zero or 1. The compositions comprising this polyester and an aromatic vinyl monomer, when hardened in the presence of a catalyst, exhibit a lower shrinkage during the hardening and give molded products with improved resistance to alkalis and to boiling water.Type: GrantFiled: March 11, 1981Date of Patent: January 25, 1983Assignee: Japan Synthetic Rubber Co., Ltd.Inventors: Katuhiro Ishikawa, Ryotaro Ohno, Masatoshi Arakawa
-
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.
-
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
-
Patent number: 4343932Abstract: The invention provides unsaturated polyester compositions which can be cured to form flexible objects, which compositions comprise terminal 1,2-alkene dicarboxylic acid in an amount of 1-25, preferably 3-15 mol-percent, calculated on the total amount of dicarboxylic acid, and 1-8, preferably 2.5-6 mol-percent of the dicarboxylic acids in the chain of the polyester consists of trans-1,2-alkene dicarboxylic acid.Type: GrantFiled: December 10, 1980Date of Patent: August 10, 1982Assignee: Internationale Octrooi Maatschappij "Octropa" BVInventors: Jacob J. Prooi, Waltherus J. Sep, Wilhelmina Westerhof
-
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
-
Patent number: 4322504Abstract: An unsaturated polyester suitable as a binder which comprises a reaction product of(A) an acid component comprising one or a mixture of .alpha.,.beta.-mono-olefinically unsaturated dicarboxylic acids or polycarboxylic acids free from polymerizable carbon-carbon multiple bonds or functional derivatives thereof,(B) a polyhydric alcohol,(C) a polycyclic compound containing a norbornane ring system and having one or more identical substituents selected from carboxyl, hydroxy and amino groups, and(D) an acrylic compound which is capable of condensing with at least one of components (A) to (C), i.e. a hydroxyalkyl ester of acrylic or methacrylic acid having up to 3 carbon atoms in the hydroxyalkyl groups, or -alkylol-acryl- or methacrylamides containing up to 4 carbon atoms in the alkylol group or mixtures thereof and a process of their preparation.Type: GrantFiled: September 11, 1980Date of Patent: March 30, 1982Assignee: Hoechst AktiengesellschaftInventors: Reinhard Wagner, Gerhard Werner, Gunther Hencken, Christoph Just
-
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.
-
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
-
Patent number: 4307002Abstract: An unsaturated polyester suitable as a binder which comprises a reaction product of(A) an acid component comprising one or a mixture of .alpha.,.beta.-mono-olefinically unsaturated dicarboxylic acids or polycarboxylic acids free from polymerizable carbon-carbon multiple bonds or functional derivatives thereof,(B) a polyhydric alcohol,(C) a polycyclic compound containing a norbornane ring system and having one or more identical substituents selected from carboxyl, hydroxy and amino groups, and(D) an acrylic compound which is capable of condensing with at least one of components (A) to (C) and a process of their preparation.Type: GrantFiled: November 13, 1978Date of Patent: December 22, 1981Assignee: Hoechst AktiengesellschaftInventors: Reinhard Wagner, Gerhard Werner, Gunther Hencken
-
Patent number: 4304878Abstract: A method is disclosed for treating polyester resin systems to suppress gel-time drift for the useable storage life of the resin system. The method comprises contacting a solution containing a polyester binder with an organic acid either between formulation stages or after formulation of the resin system. Typically useful organic acids include aromatic dicarboxylic acids such as phthalic acid and unsaturated aliphatic dicarboxylic acids such as fumaric acid. Comparative data for gel times of polyester resin system samples treated according to the disclosed method show suppression of gel-time drift to as low as 6 percent of the gel-time drift of counterpart untreated resin system samples.Type: GrantFiled: July 27, 1979Date of Patent: December 8, 1981Assignee: Koppers Company, Inc.Inventor: Hilda Howell
-
Patent number: 4294751Abstract: This invention involves a curable molding composition comprising a mixture of (a) a polyester of the following formula: ##STR1## wherein n has an average value between about 1.Type: GrantFiled: April 14, 1980Date of Patent: October 13, 1981Assignee: Union Carbide CorporationInventor: Hugh C. Gardner
-
Patent number: 4293686Abstract: This invention comprises a polymerizable composition of a liquid mixture of (a) an unsaturated polyester, (b) a half ester characterized by the following empirical formula: ##STR1## wherein n is a number having an average value of about 1.5 to less than about 4, m is equal to the free valence of A less the average value of n, A is the hydroxyl-free residue of an organic polyol which contained from 2 to 4, inclusive, hydroxyl groups, OH, in formula (I), (c) maleic anhydride and (d) an ethylenically unsaturated monomer. This composition is suitable for use in the manufacture of fiber reinforced plastic compositions.Type: GrantFiled: April 18, 1980Date of Patent: October 6, 1981Assignee: Union Carbide CorporationInventor: Hugh C. Gardner
-
Patent number: 4290938Abstract: A thermosetting injection molding compound comprising a specific crystalline unsaturated polyester comprising (A) a crystalline unsaturated polyester of terephthalic acid/fumaric acid=5/5-1/9 by mol (acid component) and 1,4-butanediol/other glycol=7/3-10/0 (glycol component) and (B) a styrene type monomer and/or allyl type monomer, and having specific ranges of a viscosity, a melting point and an acid value, said crystalline unsaturated polyester resin being admixed with (C) a glass fiber and (D) other additives in a specific ratio.Type: GrantFiled: January 4, 1980Date of Patent: September 22, 1981Assignee: Toyo Boseki Kabushiki Kaisha Co., Ltd.Inventors: Hideo Miyake, Junichi Sakamoto, Masakazu Sawaki, Mamoru Hara
-
Patent number: 4285845Abstract: To allow the use of stearyl stearate or paraffin in amounts to restrict styrene evaporation from an unsaturated polyester resin during curing, there is present in the resin a small amount (0.1 to 5% by weight) of a long-chain vinyl compound of the formula ##STR1## wherein R is straight- or branched-chain substituted or unsubstituted aliphatic C.sub.6 -C.sub.24 hydrocarbon,Y=H or CH.sub.3,n=zero or 1, ##STR2## Preferred such compounds are lauryl and stearyl methacrylate. The resins are made by admixture of the selected compound(s) with the conventional other components of the resin.Type: GrantFiled: August 3, 1979Date of Patent: August 25, 1981Assignee: Scott Bader Company LimitedInventor: Robert F. Russell
-
Patent number: 4280979Abstract: Novel polyester diols are described containing aliphatically saturated divalent diacyl moieties and olefinically unsaturated divalent diacyl moieties in a mole ratio of 0.25:1 to 3:1; and divalent dioxy moieties which are linear and/or branched, preferably divalent branched dioxy moieties and divalent linear dioxy moieties in a mole ratio of 0.3:1 to 3:1, the diacyl moieties being bonded through ester linkage to the dioxy moieties in a mole ratio of at least 1.75 dioxy moieties per diacyl moiety, wherein the polyester diol is end-blocked essentially only by alcoholic hydroxyl groups and has an acid number of less than 3. The novel polyester diols are highly useful in the production of polyurethane/vinyl polymer copolymers by reaction with polyisocyanates and polymerizable ethylenically unsaturated monomers.Type: GrantFiled: September 18, 1979Date of Patent: July 28, 1981Assignee: Union Carbide CorporationInventors: Raymond A. Dunleavy, William A. Gill
-
Patent number: 4281074Abstract: In the first stage a mixture of a crude diene adduct of 2-naphthol with maleic anhydride is polycondensed at a temperature within the range from 180.degree. to 200.degree. C. with excess glycol or with a dihydric aromatic alcohol, from 0.1 to 3 moles of the alcohol being used per 1 mole of the adduct. In the second stage, the thus obtained product is condensed at a temperature within the range from 160.degree. to 210.degree. C. with an unsaturated acid or the anhydride thereof and with the addition of an equimolar quantity (with respect to the acid or its anhydride) of glycol and/or a dihydric aromatic alcohol. The resulting product is then dissolved in styrene and copolymerized to obtain a cured polyester resin. Propylene glycol, diethylene glycol, dipropylene glycol or butylene glycol may be used as the glycol. The C.sub.2 or C.sub.Type: GrantFiled: February 26, 1980Date of Patent: July 28, 1981Assignee: Polska Akademia Nauk, Zaklad PolimerowInventors: Zbigniew Jedlinski, Antoni Kotas, Boleslaw Ryndak, Stanislaw Mazur, Jan Czarnecki, Mieczyslaw Walkowicz, Stanislaw Jedlinski
-
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
-
Patent number: 4275176Abstract: The graft polyester compositions of the invention are especially useful as size compositions since they can be applied to the yarn from a solventless mixture and require only at least one of the application of heat or irradiation to graft polymerize the size in situ on the yarn. The graft polyester of the invention comprises the reaction product of (1) an unsaturated polyester which is the reaction product of at least one polycarboxylic acid reactant, preferably a dicarboxylic acid reactant and at least one polyhydric alcohol reactant, preferably a diol, wherein a minor effective proportion of at least one of said reactants is .alpha.,.beta.-ethylenically unsaturated with (2) at least one monovinyl monomer reactant comprising at least one acidic monovinyl monomer containing at least one carboxyl group or a mixture of said vinyl monomer with any monovinyl monomer.Type: GrantFiled: February 15, 1980Date of Patent: June 23, 1981Assignee: BASF Wyandotte CorporationInventor: Robert B. Login
-
Patent number: 4273888Abstract: Macromonomers are obtained by successively reacting an oligomer or polymer containing at least one hydroxyl group with a cyclic carboxylic anhydride in an amount of at least one mole of the anhydride per hydroxyl group, and reacting the product with a compound containing a single epoxide group and a single polymerizable double bond, in such proportions as to esterify all carboxyl groups in that product. Graft copolymers which are useful as steric stabilizers for dispersions of polymer particles can be made by copolymerizing the macromonomers with other polymerizable monomers.Type: GrantFiled: December 7, 1979Date of Patent: June 16, 1981Assignee: Imperial Chemical Industries LimitedInventor: Clive W. Graetz
-
Patent number: 4259224Abstract: The present invention relates to a special copolymer solution of acrylic resin, containing 65 to 75% by weight of copolymer solids and 25 to 35% by weight of solvent. The invention also relates to a process for the manufacture of the copolymers which are contained in the copolymer solution; and, furthermore, the invention relates to the use of copolymer solutions for the manufacture of coating compositions for lacquer systems which are low in solvents and contain polyisocyanates and in which the copolymer manufactured according to the invention is contained as the resin component which carries hydroxyl groups.Type: GrantFiled: May 25, 1977Date of Patent: March 31, 1981Assignee: Hoechst AktiengesellschaftInventors: Horst Dalibor, Hans-Joachim Kiessling, Peter Quednau
-
Patent number: 4259457Abstract: There are disclosed graft polyesters useful as adhesives and coatings and especially useful in processes for sizing spun and continuous filament synthetic organic and inorganic fibrous yarn. One embodiment of the invention is a textile size composition having free carboxyl groups which is prepared in situ on a textile yarn by the application of heat or radiation to a mixture of an unsaturated polyester reactant and a monovinyl monomer reactant comprising an acidic monovinyl monomer having at least one carboxyl group or mixtures thereof with any monovinyl monomer. Desizing can be accomplished by partial neutralization of the size to a pH of at least 6 by reacting the size with a base to render the graft polyester water-dispersible or water-soluble.Type: GrantFiled: July 23, 1979Date of Patent: March 31, 1981Assignee: BASF Wyandotte CorporationInventor: Robert B. Login
-
Patent number: 4237244Abstract: Molding compositions comprising terminally unsaturated polyesters, vinyl or vinylidene compounds copolymerizable therewith and elastomeric polymers have an excellent impact strength and a good heat distortion temperature, strength and rigidity.Type: GrantFiled: January 3, 1979Date of Patent: December 2, 1980Assignee: Bayer AktiengesellschaftInventors: Hannes von Harpe, Ludwig Bottenbruch, Bernd Peltzer, Hansjochen Schulz-Walz
-
Patent number: 4161471Abstract: Filled unsaturated ester bulk molding, sheet molding, premix or mat molding compositions are modified with elastomer to give finished products with both improved impact strength and improved surface characteristics. The elastomeric modifier is selected from the group consisting of chloroprene polymers and hydrocarbon polymers such as ethylene/propylene di-, ter-, or tetrapolymers.Type: GrantFiled: April 13, 1978Date of Patent: July 17, 1979Assignee: E. I. Du Pont de Nemours and CompanyInventor: Robert J. Kassal