Polymer Mixed With Unsaturated Reactant Containing Carboxylic Acid, Ester, Salt Or Anhydride Group Patents (Class 525/39)
  • Patent number: 4370447
    Abstract: 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: Grant
    Filed: March 11, 1981
    Date of Patent: January 25, 1983
    Assignee: Japan Synthetic Rubber Co., Ltd.
    Inventors: Katuhiro Ishikawa, Ryotaro Ohno, Masatoshi Arakawa
  • Patent number: 4362848
    Abstract: 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: Grant
    Filed: May 29, 1981
    Date of Patent: December 7, 1982
    Assignee: The Dow Chemical Co.
    Inventors: Hans R. Friedli, Donald L. Nelson, John L. Massingill, Jr.
  • Patent number: 4345048
    Abstract: 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: Grant
    Filed: January 21, 1980
    Date of Patent: August 17, 1982
    Assignee: The Dow Chemical Company
    Inventors: Hans R. Friedli, Clinton J. Boriack
  • Patent number: 4343932
    Abstract: 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: Grant
    Filed: December 10, 1980
    Date of Patent: August 10, 1982
    Assignee: Internationale Octrooi Maatschappij "Octropa" BV
    Inventors: Jacob J. Prooi, Waltherus J. Sep, Wilhelmina Westerhof
  • Patent number: 4336349
    Abstract: 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: Grant
    Filed: December 22, 1980
    Date of Patent: June 22, 1982
    Assignee: The Dow Chemical Company
    Inventors: Hans R. Friedli, Clinton J. Boriack
  • Patent number: 4322504
    Abstract: 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: Grant
    Filed: September 11, 1980
    Date of Patent: March 30, 1982
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Reinhard Wagner, Gerhard Werner, Gunther Hencken, Christoph Just
  • Patent number: 4319009
    Abstract: 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: Grant
    Filed: October 13, 1978
    Date of Patent: March 9, 1982
    Assignee: The Dow Chemical Company
    Inventors: Hans R. Friedli, Donald L. Nelson, John L. Massingill, Jr.
  • Patent number: 4316835
    Abstract: 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: Grant
    Filed: April 16, 1980
    Date of Patent: February 23, 1982
    Assignee: Union Carbide Corporation
    Inventor: Hugh C. Gardner
  • Patent number: 4307002
    Abstract: 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: Grant
    Filed: November 13, 1978
    Date of Patent: December 22, 1981
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Reinhard Wagner, Gerhard Werner, Gunther Hencken
  • Patent number: 4304878
    Abstract: 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: Grant
    Filed: July 27, 1979
    Date of Patent: December 8, 1981
    Assignee: Koppers Company, Inc.
    Inventor: Hilda Howell
  • Patent number: 4294751
    Abstract: 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: Grant
    Filed: April 14, 1980
    Date of Patent: October 13, 1981
    Assignee: Union Carbide Corporation
    Inventor: Hugh C. Gardner
  • Patent number: 4293686
    Abstract: 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: Grant
    Filed: April 18, 1980
    Date of Patent: October 6, 1981
    Assignee: Union Carbide Corporation
    Inventor: Hugh C. Gardner
  • Patent number: 4290938
    Abstract: 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: Grant
    Filed: January 4, 1980
    Date of Patent: September 22, 1981
    Assignee: Toyo Boseki Kabushiki Kaisha Co., Ltd.
    Inventors: Hideo Miyake, Junichi Sakamoto, Masakazu Sawaki, Mamoru Hara
  • Patent number: 4285845
    Abstract: 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: Grant
    Filed: August 3, 1979
    Date of Patent: August 25, 1981
    Assignee: Scott Bader Company Limited
    Inventor: Robert F. Russell
  • Patent number: 4280979
    Abstract: 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: Grant
    Filed: September 18, 1979
    Date of Patent: July 28, 1981
    Assignee: Union Carbide Corporation
    Inventors: Raymond A. Dunleavy, William A. Gill
  • Patent number: 4281074
    Abstract: 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: Grant
    Filed: February 26, 1980
    Date of Patent: July 28, 1981
    Assignee: Polska Akademia Nauk, Zaklad Polimerow
    Inventors: Zbigniew Jedlinski, Antoni Kotas, Boleslaw Ryndak, Stanislaw Mazur, Jan Czarnecki, Mieczyslaw Walkowicz, Stanislaw Jedlinski
  • Patent number: 4275176
    Abstract: 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: Grant
    Filed: February 15, 1980
    Date of Patent: June 23, 1981
    Assignee: BASF Wyandotte Corporation
    Inventor: Robert B. Login
  • Patent number: 4274994
    Abstract: 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: Grant
    Filed: June 13, 1980
    Date of Patent: June 23, 1981
    Assignee: The B. F. Goodrich Company
    Inventor: Changkiu K. Riew
  • Patent number: 4273888
    Abstract: 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: Grant
    Filed: December 7, 1979
    Date of Patent: June 16, 1981
    Assignee: Imperial Chemical Industries Limited
    Inventor: Clive W. Graetz
  • Patent number: 4259457
    Abstract: 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: Grant
    Filed: July 23, 1979
    Date of Patent: March 31, 1981
    Assignee: BASF Wyandotte Corporation
    Inventor: Robert B. Login
  • Patent number: 4259224
    Abstract: 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: Grant
    Filed: May 25, 1977
    Date of Patent: March 31, 1981
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Horst Dalibor, Hans-Joachim Kiessling, Peter Quednau
  • Patent number: 4237244
    Abstract: 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: Grant
    Filed: January 3, 1979
    Date of Patent: December 2, 1980
    Assignee: Bayer Aktiengesellschaft
    Inventors: Hannes von Harpe, Ludwig Bottenbruch, Bernd Peltzer, Hansjochen Schulz-Walz
  • Patent number: 4161471
    Abstract: 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: Grant
    Filed: April 13, 1978
    Date of Patent: July 17, 1979
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Robert J. Kassal