Polymer Derived From Polycarboxylic Acid Or Anhydride And Polyhydroxy Compound Wherein At Least One Of The Reactants Contains Ethylenic Unsaturation Patents (Class 525/43)
  • Patent number: 4532297
    Abstract: This invention relates to low viscosity curable polyester resin compositions and a process for the preparation thereof, which compositions contain a mixture of (i) an unsaturated ester terminally modified with a reactive olefin such as dicyclopentadiene or other Diels-Alder adducts of cyclopentadiene with an olefinic or acetylenic hydrocarbon or alkylated derivative thereof and (ii) a polymerizable ethylenically unsaturated monomer which serves to crosslink the unsaturated ester to a thermoset product. Fiber reinforced thermoset articles can be produced from these low viscosity curable polyester resin compositions.
    Type: Grant
    Filed: June 29, 1984
    Date of Patent: July 30, 1985
    Assignee: Union Carbide Corporation
    Inventor: Hugh C. Gardner
  • Patent number: 4532296
    Abstract: This invention relates to a process for producing low viscosity curable polyester resin compositions, which compositions contain a mixture of (i) an unsaturated ester terminally modified with a reactive olefin such as dicyclopentadiene or other Diels-Alder adducts of cyclopentadiene with an olefinic or acetylenic hydrocarbon or alkylated derivative thereof and (ii) a polymerizable ethylenically unsaturated monomer which serves to crosslink the unsaturated ester to a thermoset product. Fiber reinforced thermoset articles can be produced from these curable polyester resin compositions.
    Type: Grant
    Filed: June 29, 1984
    Date of Patent: July 30, 1985
    Assignee: Union Carbide Corporation
    Inventor: Hugh C. Gardner
  • Patent number: 4522976
    Abstract: A low viscosity, stable graft polymer dispersion is prepared by polymerizing in the presence of a free radical initiator, from about 25 to about 70 weight percent based on the total weight of the dispersion, an ethylenically unsaturated monomer or mixture of monomers, in a polyol mixture comprising (1) from about 25 to about 99 weight percent of a polyol containing from 2 to 8 hydroxyl groups and having an equivalent weight from 30 to about 200, (2) from about 1 to about 75 weight percent of a macromer containing induced unsaturation, said macromer comprising the reaction product of a polyether polyol having an equivalent weight from 100 to 10,000 with a compound having both ethylenic unsaturation and a group selected from the group consisting of a hydroxyl, carboxyl, anhydride, isocyanate and epoxy or mixtures thereof. These graft polymer dispersions are useful for preparing polyurethane products.
    Type: Grant
    Filed: May 17, 1984
    Date of Patent: June 11, 1985
    Assignee: BASF Wyandotte Corporation
    Inventors: Oscar M. Grace, Steven E. Wujcik, Duane A. Heyman
  • Patent number: 4458038
    Abstract: White graft polymer dispersions in polyoxyalkylene polyether polyols are employed together with flame retardant compounds to prepare flame retardant polyurethane foams. The polymer dispersions employ less than 0.1 mole of induced unsaturation per mole of polyol mixture. Improved processes for the preparation of these polymer dispersions employ either maleate or fumarate derived polyetherester polyols or polyetherester polyols prepared by reacting a polyoxyalkylene polyether polyol with a compound selected from the group consisting of maleic acid, maleic anhydride and fumaric acid and an alkylene oxide in the presence of salts and oxides of divalent metals.
    Type: Grant
    Filed: March 3, 1983
    Date of Patent: July 3, 1984
    Assignee: BASF Wyandotte Corporation
    Inventors: Gerhard G. Ramlow, Duane A. Heyman, Oscar M. Grace
  • Patent number: 4454255
    Abstract: White graft polymer dispersions in polyoxyalkylene polyether polyols are employed together with flame retardant compounds to prepare flame retardant polyurethane foams. The polymer dispersions employ less than 0.1 mole of induced unsaturation per mole of polyol mixture. Improved processes for the reparation of these polymer dispersions employ either isomerized maleate containing polyetherester polyols or polyetherester polyols prepared by reacting a polyoxyalkylene polyether polyol, a polycarboxylic acid anhydride and an alkylene oxide in the presence of salts and oxides of divalent metals.
    Type: Grant
    Filed: April 1, 1982
    Date of Patent: June 12, 1984
    Assignee: BASF Wyandotte Corporation
    Inventors: Gerhard G. Ramlow, Duane A. Heyman, Oscar M. Grace, Curtis J. Reichel, Robert J. Hartman
  • Patent number: 4451638
    Abstract: Alkali metal polyester silicate resinous products are produced by mixing a polyhydroxy organic compound, an alkali metal silicate and a polycarboxylic acid, then heating the mixture to a temperature between the melting point of the polycarboxylic acid and the boiling temperature of the polyol while agitating until the reaction is complete.
    Type: Grant
    Filed: February 19, 1980
    Date of Patent: May 29, 1984
    Inventor: David H. Blount
  • Patent number: 4420587
    Abstract: 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: Grant
    Filed: September 27, 1982
    Date of Patent: December 13, 1983
    Assignee: The Dow Chemical Company
    Inventor: Robert E. Hefner, Jr.
  • Patent number: 4394480
    Abstract: An unsaturated polyester resin composition comprising an unsaturated polyester resin, a polymerizable monomer and a mixture of block copolymers having acid groups prepared by first copolymerizing in a first copolymerization reaction a polymeric peroxide with a monomer A or B, or with an unsaturated acid together with monomer A or B, thereby obtaining a copolymer having peroxy bonds in the molecule thereof, which copolymer is further copolymerized in the second copolymerization reaction with each of monomers A or B or the unsaturated acid which were excluded in the first copolymerization reaction to give the block copolymer mixture, which composition shows no segregation of the low shrinkage agent on thickening by a thickener and the said composition gives cured moldings of reduced shrinkage which are excellent in many characteristics.
    Type: Grant
    Filed: March 24, 1982
    Date of Patent: July 19, 1983
    Assignee: Nippon Oil and Fats Co., Ltd.
    Inventors: Norihisa Ujikawa, Kyosuke Fukushi
  • Patent number: 4387171
    Abstract: An unsaturated halogenated or non-halogenated polyester resin composition for open lay-up moulding and containing styrene as an agent for cross-linking during curing additionally contains 0.1 to 5% by weight, based on the total weight of the composition, of at least one C.sub.18-40 .alpha.-olefine compound which is theoretically capable of taking part in the cross-linking reaction.When the composition contains a non-halogenated polyester resin, then the .alpha.-olefine compound itself serves to restrict styrene evaporation from the composition.For halogenated polyester resin compositions, the .alpha.-olefine, although not usually by itself providing such a marked restriction of styrene evaporation, does allow incorporation into the composition of a waxy compound in an amount sufficiently large to achieve the desired styrene evaporation restriction without deterioration of the adhesion properties of the composition during lay-up.
    Type: Grant
    Filed: August 21, 1981
    Date of Patent: June 7, 1983
    Assignee: Scott Baker Company Limited
    Inventor: Robert F. Russell
  • Patent number: 4376842
    Abstract: Novel peroxyketals having the general formula ##STR1## are provided, wherein R.sup.1 represents a tert. alkyl group having 4-12 carbon atoms and R.sup.2 represents a branched or a non-branched alkyl group having 1-12 carbon atoms or a substituted or unsubstituted cycloalkyl group having 5-12 carbon atoms. The peroxyketals can be used to advantage for initiating the copolymerization reaction of ethylenically unsaturated compounds such as unsaturated polyester resins containing both an unsaturated polyester and an ethylenically unsaturated monomer such as styrene.
    Type: Grant
    Filed: February 12, 1981
    Date of Patent: March 15, 1983
    Assignee: Akzona Incorporated
    Inventors: Wilhelmus M. Beyleveld, Lodewijk Roskott
  • Patent number: 4360540
    Abstract: There are disclosed radiation curable compositions containing (a) about 5-95% by weight of at least one cyanoalkoxyalkyl or cyanothiaalkylalkyl acrylate, (b) about 1-90% by weight of a photopolymerizable acrylated polymer or oil, and (c) from 0 to about 5% by weight of a photoinitiator. The compositions are useful as 100% solids coatings and adhesives compositions which are curable upon exposure to radiation, and which are useful in a variety of applications such as for coating textiles and fabrics, for producing pressure sensitive adhesives, and for producing laminating adhesives.
    Type: Grant
    Filed: December 30, 1980
    Date of Patent: November 23, 1982
    Assignee: Rohm and Haas Company
    Inventor: Joshua A. Chong
  • Patent number: 4355136
    Abstract: Disclosed are compositions comprising a polyester derived from 100 mole % of an acid component and 100 mole % of a glycol component, the acid component comprising about 30-90 mole % of at least one .alpha.,.beta.-ethylenically unsaturated dicarboxylic acid and about 70-10 mole % of a compound containing a cinnamic acid moiety, and the glycol component comprising at least one saturated aliphatic glycol containing from 2 to 10 carbon atoms. These compositions have improved resistance to attack by organic solvents.
    Type: Grant
    Filed: January 4, 1982
    Date of Patent: October 19, 1982
    Assignee: Eastman Kodak Company
    Inventors: John R. Dombroski, Fred W. Light, Jr.
  • Patent number: 4351919
    Abstract: 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: Grant
    Filed: October 13, 1981
    Date of Patent: September 28, 1982
    Inventor: David H. Blount
  • 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: 4309519
    Abstract: Flyback transformers having good adhesiveness, crack resistance, arc resistance, without producing corona discharge can be produced by insulation treating flyback transformers with a low-shrinkage resin composition comprising (a) an unsaturated polyester produced by reacting partially esterified dicyclopentadiene carboxylic acid, which has been obtained by reacting dicyclopentadiene or hydroxylated dicyclopentadiene, and maleic acid or anhydride, with one or more polyhydric alcohols, (b) a monomer having a vinyl group and (c) a low-shrinkage agent.
    Type: Grant
    Filed: July 9, 1980
    Date of Patent: January 5, 1982
    Assignee: Hitachi Chemical Company, Ltd.
    Inventors: Mitsuo Obara, Akira Kageyama, Isao Uchigasaki
  • 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: 4284547
    Abstract: A water-in-resin emulsion for producing a porous plastic is comprised of a mixture of water dispersed in discrete droplets uniformly throughout a continuous phase of a resinous copolymerizable composition which includes a copolymerizable mixture containing a liquid unsaturated polyester of a polyhydric alcohol and saturated and ethylenically unsaturated dicarboxylic acids and a compound having a polymerizable CH.sub.2 .dbd.C< group, wherein the copolymerizable mixture has a molecular weight in the range of from about 2500 to about 3500; a cobalt salt promoter in an amount within the range of from about 0.25 to about 0.5% based on the weight of the copolymerizable mixture; a tertiary aromatic amine accelerator in an amount within the range of from about 0.75 to about 1.75% based on the weight of the copolymerizable mixture; and, a lithium salt emulsifier in an amount within the range of from about 0.5 to about 1.5% based on the weight of the copolymerizable mixture.
    Type: Grant
    Filed: June 26, 1980
    Date of Patent: August 18, 1981
    Inventor: Richard C. Sulick
  • Patent number: 4278575
    Abstract: PCT No. PCT/JP78/00013 Sec. 371 Date June 28, 1979 Sec. 102(e) Date June 19, 1979 PCT Filed Oct. 26, 1978 PCT Pub. No. W079/00240 PCT Pub. Date May 3, 1979It has previously been known that the poor pigment dispersibility of an acrylic paint is its defect. The present invention provides a modified acrylic copolymer having superior pigment dispersibility and being suitable as a vehicle for acrylic paints. The copolymer is obtained by polymerizing specified proportions of a polyester containing an unsaturated double bond, a dialkylaminoalkyl (meth)acrylate, methyl methacrylate and another polymerizable monomer, and has a weight average molecular weight/number average molecular weight ratio within the range of 3 to 20.
    Type: Grant
    Filed: October 26, 1978
    Date of Patent: July 14, 1981
    Assignee: Dainippon Ink & Chemicals, Inc.
    Inventors: Hidehisa Nakamura, Ryoichi Hori, Emiko Isomoto, Yoichi Murakami
  • Patent number: 4274992
    Abstract: 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: Grant
    Filed: December 11, 1979
    Date of Patent: June 23, 1981
    Assignee: PPG Industries, Inc.
    Inventors: Peter R. Buechler, Earl E. Parker, Kenneth L. Mollohan
  • Patent number: 4263413
    Abstract: The invention comprises a homogeneous liquid mixture of (a) a half ester of an organic polyol characterized by the following empirical formula: ##STR1## wherein n is a number having an average value of about 1.8 to less than about 4, m is equal to the free valence of R less the average value of n, R is the hydroxyl-free residue of an organic polyol which contained from 2 to 4, inclusive, hydroxyl groups, OH, in formula (I), (b) maleic anhydride, (c) an ethylenically unsaturated monomer which forms a liquid homogeneous mixture with and is copolymerizable with the half ester and maleic anhydride, and (d) a basic compound.
    Type: Grant
    Filed: March 27, 1980
    Date of Patent: April 21, 1981
    Assignee: Union Carbide Corporation
    Inventors: Hugh C. Gardner, Robert J. Cotter
  • Patent number: 4252704
    Abstract: Graft polymers comprising at least one monomer selected from vinyl aromatic monomers and acrylic monomers polymerized in the presence of a cross-linked, aliphatic polyester elastomer.
    Type: Grant
    Filed: June 4, 1979
    Date of Patent: February 24, 1981
    Assignee: Borg-Warner Corporation
    Inventor: John C. Falk
  • Patent number: 4247659
    Abstract: Water soluble epoxy ester copolymers adapted for sanitary can use comprise an hydroxy functional epoxy ester of a polyepoxide having an average molecular weight of about 300 to about 1100 and a 1,2-epoxy equivalency of about 1.4 to about 2.0, esterified with an at least approximately stoichiometric proportion, based on epoxide functionality, of monocarboxylic acid selected from benzoic acid, C.sub.1 -C.sub.8 alkyl substituted benzoic acid, and C.sub.6 -C.sub.10 alkanoic acid, the esterification reaction being continued to provide an acid number of less than 20, this hydroxy functional epoxy ester is polyesterified with from 1.
    Type: Grant
    Filed: March 9, 1979
    Date of Patent: January 27, 1981
    Assignee: DeSoto, Inc.
    Inventors: Kazys Sekmakas, Raj Shah
  • Patent number: 4246367
    Abstract: The invention disclosed is for a method of preparing unsaturated polyester resins containing high amounts of dicyclopentadiene. These polyester resins are useful in curable liquid compositions containing them together with a monomeric copolymerizable component. Such compositions may be used at ambient or elevated temperature, in casting, laminating or molding techniques known to the polyester resin art.
    Type: Grant
    Filed: September 24, 1979
    Date of Patent: January 20, 1981
    Assignee: United States Steel Corporation
    Inventor: Omer E. Curtis, Jr.
  • Patent number: 4233413
    Abstract: A resin composition comprising (A) 25 to 45 parts by weight of an unsaturated polyester having special structure, (B) 40 to 60 parts by weight of polymerizable monomer such as styrene, and (C) 4.5 to 15 parts by weight of a polystyrene, has low shrink properties and excellent electrical properties when molded, particularly by casting.
    Type: Grant
    Filed: November 28, 1978
    Date of Patent: November 11, 1980
    Assignee: Hitachi Chemical Company, Ltd.
    Inventors: Noboru Monma, Iwao Maekawa, Tutomu Sarudate, Hidetaka Sato, Isao Uchigasaki
  • Patent number: 4229559
    Abstract: 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: Grant
    Filed: May 1, 1979
    Date of Patent: October 21, 1980
    Assignee: Union Carbide Corporation
    Inventors: Robert J. Cotter, Hugh C. Gardner
  • Patent number: 4228251
    Abstract: A resin composition which comprises (A) 50 to 90 parts by weight of an unsaturated ester oligomer produced by reacting a glycol, hydroxylated dicyclopentadiene, and at least one unsaturated dibasic acid or anhydride thereof until an acid value of less than 40, (B) 50 to 10 parts by weight of one or more polymerizable monomers, and (C) 3 to 15 parts by weight of polystyrene based on 100 parts by weight of the total of the components (A) and (B), can give molded articles having low shrink properties and improved color shading, cracks, etc.
    Type: Grant
    Filed: November 30, 1978
    Date of Patent: October 14, 1980
    Assignee: Hitachi Chemical Company, Ltd.
    Inventors: Iwao Maekawa, Isao Uchigasaki, Noboru Monma
  • Patent number: 4195014
    Abstract: Unsaturated polyester resins having improved fire retardant properties comprise a halogen-containing unsaturated polyester of a polycarboxylic compound and a polyhydric alcohol together with an additive mixture comprising iron or a compound of iron, copper or a compound of copper, and a compound of molybdenum. The unsaturated polyester resin may be copolymerized with an unsaturated monomer to prepare castings, laminated products, reinforced articles and the like having low burning rates, low smoke generations, and beneficial char formation in the presence of a flame.
    Type: Grant
    Filed: January 21, 1977
    Date of Patent: March 25, 1980
    Assignee: Hooker Chemicals & Plastics Corp.
    Inventors: Edwin Dorfman, Raymond R. Hindersinn, Willis T. Schwartz, Jr.
  • Patent number: 4172060
    Abstract: A reactive lacquer composition comprising hydroxyl containing polymers, a polyisocyanate, a solvent having no active hydrogen atoms, wherein the binder of the lacquer composition contains(A) 60 to 80 percent of a copolymer of(a) unsaturated polyesters having acid number of 10 to 20 and hydroxyl numbers of 100 to 250, which polyesters are prepared from saturated dicarboxylic acids or anhydrides thereof and diols having 2 to 15 carbon atoms, it being possible to replace up to 20 percent of the saturated dicarboxylic acids with saturated dimeric fatty acids which have 36 carbon atoms and contain two carboxyl groups, and(b) a mixture of monomers, consisting of (b.sub.1) styrene or methyl methacrylate, and (b.sub.2) at least one of hydroxylethyl acrylate, hydroxyethyl methacrylate, hydroxypropyl acrylate, and hydroxy-n-butyl acrylate, and(B) 20 to 40 percent of an organic polyisocyanate.
    Type: Grant
    Filed: May 25, 1977
    Date of Patent: October 23, 1979
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Horst Dalibor, Hans-Joachim Kiessling, Peter Quednau
  • Patent number: T101903
    Abstract: 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: Grant
    Filed: April 24, 1981
    Date of Patent: June 1, 1982
    Inventor: John R. Dombroski