Material Contains A Group Iva Metal Atom (ge, Sn, Pb) Patents (Class 528/283)
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Patent number: 5407772Abstract: Unsaturated linear polymers have repeating units of a reaction product of a first monomer, a second monomer, a third monomer and optionally a fourth monomer. The linear polymers have a glass transition temperature ranging from about 52.degree. C. to about 61.degree. C. The first monomer should have a weight average molecular weight less than 200. The second monomer may be a dicarboxylic acid or diester which is different than the third monomer. A concentration of second residues of the polymer, derived from the second monomer, ranges from about 3 wt. % to about 15 wt. %, based on the total weight of the polymer. The third monomer is an aromatic dicarboxylic acid or an ester thereof. In the polymer, a concentration of third residues, derived from the third monomer, ranges from about 40 wt. % to about 55 wt. %, based on the total weight of the polymer. The fourth monomer is a diol having a higher molecular weight than the first monomer.Type: GrantFiled: November 30, 1993Date of Patent: April 18, 1995Assignee: Xerox CorporationInventors: Robert D. Bayley, Carol A. Fox, Thomas R. Hoffend, Hadi K. Mahabadi, Enno E. Agur, Guerino Sacripante, Michael S. Hawkins
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Patent number: 5397827Abstract: The thermoplastic polyester compositions of the present invention are characterized by containing special colloidal silica particles having a straight-chain or branched shape, so when formed into film, particularly film for magnetic tape, there are attained superior abrasion resistance, scratch resistance and sliding property.Type: GrantFiled: July 21, 1992Date of Patent: March 14, 1995Assignee: Toray Industries, Inc.Inventors: Masahiro Kimura, Tomoji Saeki, Masaru Suzuki, Minoru Yoshida, Toshihiro Sasaki
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Patent number: 5389719Abstract: Cyclic tin catalysts are employed for the preparation of branched polyesters from macrocyclic polyester oligomers.Type: GrantFiled: June 20, 1994Date of Patent: February 14, 1995Assignee: General Electric CompanyInventors: Tohru Takekoshi, Eric J. Pearce
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Patent number: 5387666Abstract: Cyclic tin catalysts are employed for the preparation of branched polyesters from macrocyclic polyester oligomers. They are less susceptible than previously known catalysts to the presence of acidic impurities in the oligomer compositions.Type: GrantFiled: June 20, 1994Date of Patent: February 7, 1995Assignee: General Electric CompanyInventors: Tohru Takekoshi, Eric J. Pearce
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Patent number: 5385773Abstract: Disclosed is a process for producing copolyesters having repeat units from a dicarboxylic acid component comprising at least 90 mol % terephthalic acid and a glycol component comprising about 10-95 mol % 1,4-cyclo-hexanedimethanol and from about 90-5 mol % ethylene glycol comprising reacting the dicarboxylic acid component and the glycol component at temperatures sufficient to effect esterification or transesterification and polycondensing the reaction product in the presence of a catalyst and inhibitor system consisting essentially of Mn, Zn, Ti, Ge and P, all parts by weight based on the weight of the copolyester.Type: GrantFiled: April 27, 1993Date of Patent: January 31, 1995Assignee: Eastman Chemical CompanyInventors: Cheuk C. Yau, Clinton Cherry
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Patent number: 5382651Abstract: A method for the production of polyester suitable to be molded into a film with excellent surface properties.The method comprises passing dispersion-in-water type silica sol with pH 8 to 11 including sodium oxide as a stabilizer and silica particles with average diameters 0.01 to 0.3 .mu.m through a column of cation exchange resin having the following formula 1 and the strong basic anion exchange having the following formula 2, in sequence to adjust the pH value to 2 to 4, adding an hydrogen bonding agent and ethylene glycol thereto, heating the resultant silica sol under a reduced pressure to remove water, so as to obtain dispersion-in-ethylene glycol type silica sol, and adding 0.01 to 5% by weight of the dispersion-in-ethylene glycol type silica sol, as based on the weight of polyester to be produced, at any step during the ester interchange reaction.Type: GrantFiled: August 17, 1993Date of Patent: January 17, 1995Assignee: Cheil Synthetics, Inc.Inventors: Kwang T. Kim, Tae H. Kim, Seung B. Jun
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Patent number: 5382474Abstract: Disclosed is a process for producing polyethylene terephthalate fibers with reduced flammability which comprises the following steps:(a) condensating terephthalic acid and ethylene glycol in a mole ratio of from 1:1.1-1.5 at a temperature of from 180.degree.to 240.degree. C. in the presence of a catalyst;(b) adding a polyalkylene glycol phosphate ester;(c) polycondensating at a temperature of from 265.degree.-280.degree. C. under a pressure decreasing from 760 torr to less than 2 torr to form the polyethylene terepthalate; and(d) melt spinning fibers.Type: GrantFiled: September 24, 1992Date of Patent: January 17, 1995Assignee: BASF CorporationInventors: Atish Adhya, Thomas F. Corbin, Robert L. Lilly
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Patent number: 5378796Abstract: The present invention relates to a process for preparing copolyesters which involves two steps. The first step is a diol interchange step, and the second step is a polycondensation step. More specifically, the process involves (I) reacting in the presence of a polycondensation catalyst a dihydroxy terephthalate-containing compound having the formula: ##STR1## wherein n is 1 to 10 and at least 99% of the endgroups are ethylene glycol moieties; and 0.01 to 10 moles, based on moles of the dihydroxy terephthalate-containing compound, of a diol, and (II) polycondensing the reaction product of Step (I) to form a copolyester while excess diol is removed until desired molecular weight is obtained. This process does not include a transesterification of a dialkyl ester reaction or an esterification reaction which are usually used to produce copolyesters. Moreover, this process allows for polyethylene terephthalate and copolyesters prepared therefrom to be produced on an integrated production line.Type: GrantFiled: February 9, 1994Date of Patent: January 3, 1995Assignee: Eastman Chemical CompanyInventors: Scott E. George, Douglas C. Hoffman
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Patent number: 5378797Abstract: Aliphatic polyesters are produced by the acylative ether cleavage of aliphatic monomers having at least one arylmethoxy group and at least one hydrocarbyl group. Alternatively, monomeric systems of aliphatic compounds having at least two arylmethoxy groups together with aromatic or aliphatic compounds having at least two halocarbonyl groups are used. Lewis acids are used to catalyze the reaction.Type: GrantFiled: October 4, 1993Date of Patent: January 3, 1995Assignee: Shell Oil CompanyInventors: Jan H. H. Meurs, Feike De Jong
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Patent number: 5374707Abstract: New compounds including bis-.beta.-hydroxy ethyl bibenzoate containing less than 2.5%, and preferably less than 1%, diethylene glycol and a process for the production of the bis-.beta.-hydroxy ethyl bibenzoate by the condensation of 4,4'-biphenyl dicarboxylic acid and ethylene glycol at low temperature and pressure in the presence of a catalyst are disclosed. Use of the compounds to produce polyesters is also disclosed.Type: GrantFiled: February 18, 1993Date of Patent: December 20, 1994Assignee: Monsanto CompanyInventors: Jawed Asrar, David J. Weinkauff, A. Hameed Bhombal
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Patent number: 5350829Abstract: There is disclosed a method for producing a polyethylene naphthalate from a naphthalenedicarboxylic acid represented by the following formula (I) and a glycol, in the presence of one or more compounds of glycol-soluble magnesium compounds, glycol-soluble manganese compounds, and glycol-soluble zinc compounds; a nitrogen-containing basic compound; and a phosphorous compound; which method comprises adding a glycol-soluble germanium compound of a limited amount, as a polymerization catalyst, at a limited relationship between amounts of said metal compound, the said nitrogen-containing basic compound, and the said phosphorous compound.Type: GrantFiled: July 13, 1993Date of Patent: September 27, 1994Assignee: Fuji Photo Film Co., Ltd.Inventor: Fumio Kawamoto
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Patent number: 5348985Abstract: A process for making thermoplastic polyester foams comprises the steps of subjecting macrocyclic polyester oligomer precursors to initiators and blowing agents at a constant operating temperature in order to produce foams which unexpectedly display low foam densities.Type: GrantFiled: January 18, 1994Date of Patent: September 20, 1994Assignee: General Electric CompanyInventors: Eric J. Pearce, John W. Carbone
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Patent number: 5342902Abstract: The present invention relates to poly(ester-ether) compositions and to a process for their preparation. In particular, the invention relates to poly(ester-ether) compositions obtained by reacting a polyester which is prepared from a dicarboxylic acid and an aliphatic diol with a dihydroxy aromatic compound in the presence of a metal catalyst. Incorporation of the dihydroxy aromatic compound into the polyester chain causes an increase in the Tg value and increases the thermal stability of the polyester. These poly(ester-ether) compositions are useful in molded articles of all types.Type: GrantFiled: September 7, 1993Date of Patent: August 30, 1994Assignee: Eastman Chemical CompanyInventors: W. Ronald Darnell, W. J. Jackson, Jr.
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Patent number: 5340909Abstract: A process for producing poly(1,3-propylene terephthalate) from the reaction of either terephthalic acid or a lower dialkyl ester of terephthalic acid and 1,3-propanediol and polymerization of the monomer produced therefrom using a novel catalyst system. The novel catalyst composition includes employing an effective catalytic amount tin in the polycondensation reaction. Using the catalyst system and Hostaperm.RTM. pigments allows for the production of poly(1,3-propylene terephthalate) having yellowness of less than 4 and an IV of at least 0.80 dl/g.Type: GrantFiled: December 18, 1991Date of Patent: August 23, 1994Assignee: Hoechst Celanese CorporationInventors: Marvin L. Doerr, Joseph J. Hammer, J. R. Dees
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Patent number: 5340908Abstract: This invention relates to a process for the preparation of aromatic polyester(s) having an intrinsic viscosity greater than 0.4 dL/g in chloroform at 30.degree. C. which comprises (a) reacting diarylesters of tere and isophthalic acid(s) and dihydric phenol(s) in the melt phase in an inert atmosphere in the presence of a catalyst selected from alkoxides of Group IV B metals and derivatives of Group IV A metals and in the presence of an organic solvent at a temperature in the range of 100.degree.-300.degree. C. to form a prepolymer having intrinsic viscosity in the range of 0.1 to 0.3 dL/g in chloroform at 30.degree. C. (b) purifying the prepolymer using conventional solvent extraction methods and (c) Polycondensing the purified prepolymer at a temperature in the range of 300.degree.-350.degree. C. in presence of a catalyst selected from alkoxides of Group IVB metals and derivatives of Group IVA metals under reduced pressure.Type: GrantFiled: April 1, 1993Date of Patent: August 23, 1994Assignee: Council of Scientific & Industrial ResearchInventors: Bhaskar B. Idage, Nayaku N. Chavan, Sudhakar S. Mahajan, Swaminathan Sivaram
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Patent number: 5321117Abstract: Macrocyclic poly(alkylene dicarboxylate) oligomers are prepared by the reaction of a dicarboxylic acid chloride such as terephthaloyl chloride with at least one bis(hydroxyalkyl) ester such as bis(4-hydroxybutyl) terephthalate, in the presence of a Lewis acid as catalyst. Illustrative Lewis acids are ferric chloride, zinc chloride, zinc bromide, stannous bromide and antimony pentachloride.Type: GrantFiled: November 19, 1992Date of Patent: June 14, 1994Assignee: General Electric CompanyInventor: Daniel J. Brunelle
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Patent number: 5310848Abstract: a resin composition for a powder coating comprising a polyester A, which does not substantially set to gel and has a hydroxyl value of at least 1,200 g eq/10.sup.6 g, a polyester B, which does not substantially set to gel and has a hydroxyl value of from 200 to 1,000 g eq/10.sup.6 g, and an inner blocked isocyanate hardener, wherein the weight ratio of polyester A to polyester B is from 70:30 to 10:90 and the difference (absolute value) in gel time between these polyesters A and B is at least 3 minutes.Type: GrantFiled: January 29, 1993Date of Patent: May 10, 1994Assignee: Nippon Ester Co., Ltd.Inventors: Tokuzo Nozaki, Katsuyoshi Atsumi, Makiko Sakai
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Patent number: 5302686Abstract: A hollow article or sheet of a copolyester which comprises, as main components, terephthalic acid as a dicarboxylic acid component and ethylene glycol as a diol component and which is characterized by:(1) isophthalic acid as a dicarboxylic acid component being from 0.5 to 3.0 mol %,(2) diethylene glycol as a diol component being from 1.0 to 2.5 mol %,(3) the intrinsic viscosity being from 0.60 to 1.50 dl/g,(4) the concentration of terminal carboxyl groups being at most 18 eq/ton, and(5) the content of a cyclic trimer being at most 0.40% by weight.Type: GrantFiled: July 15, 1993Date of Patent: April 12, 1994Assignee: Mitsubishi Kasei CorporationInventors: Katsuji Tanaka, Hitoshi Matsumoto, Takuji Hirahara, Osamu Kishiro
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Patent number: 5298593Abstract: A thermotropic liquid crystalline polyester is produced by carrying out polycondensation of ester monomer [I-2], an aromatic dicarboxylic acid [II] and an aromatic carboxylic acid [III-2]. The amounts of the compounds [I-2] and [II] are substantially equivalent and the amount of the compound [III-2] is not more than 20 times that of [I-2] by mole. A thermotropic liquid crystalline polyester having good heat resistance, fluidity and uniformity can be produced.Type: GrantFiled: June 24, 1992Date of Patent: March 29, 1994Assignee: Mitsubishi Petrochemical Company, Ltd.Inventors: Eisuke Fujiwara, Haruyo Kozaki
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Patent number: 5296587Abstract: The present invention relates to a process for copolymerizing a dicarboxylic acid, a dialkyl ester, and a diol in the presence of a transesterification catalyst. The process involves heating a mixture containing carboxylic acids and esters in excess diol at elevated temperatures in the presence of a transesterification catalyst and returning any vaporized diol to the reaction vessel until the theoretical amount of alcohol and/or water have been evolved. The alcohol and/or water of reaction is not allowed to return to the vessel. When the theoretical weight of alcohol and/or water is collected, the excess diol is removed and the polymerization is allowed to proceed.Type: GrantFiled: March 22, 1993Date of Patent: March 22, 1994Assignee: Eastman Chemical CompanyInventors: Charles E. Sumner, Jr., Gary D. Boone
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Patent number: 5294695Abstract: The present invention relates to a process for preparing a polyethylene naphthalate possessed with high viscosity, characterized by sloving of various problems of the prior art by controlling the rate of the polycondensation reaction.Particularly, the present invention provides a process for preparing polyethylene naphthalate from an esterification reaction product of naphtalene dicarboxylic acid or an alkyl ester thereof and a diol, which comprises polycondensing the esterification reaction product in the presence of a polycondensation catalyst in two steps wherein the first step is carried out at a pressure ranging from 500 to 30 torr and the second step is carried out at a pressure ranging from 10 to 0.1 torr with controlling the reaction rate such that the differential increase of the intrinsic viscosity of the resultant polymer can satisfy the following equations:IV(t.sub.1)-IV(t.sub.0)<0.4 dl/g (1)IV(t.sub.2)-IV(t.sub.0)>0.3 dl/g (2)wherein: IV(t.sub.Type: GrantFiled: March 15, 1993Date of Patent: March 15, 1994Assignee: SKC LimitedInventors: Kwan-Kyung Lee, Byeong-Ho Cho, Yong-Won Kim
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Patent number: 5292855Abstract: Provided are water-dissipatable, sulfo-containing polyesters and polyester-amides having copolymerized therein thermally stable near infrared flourophoric compounds. The polymers are useful in coating or ink compositions, which are in turn useful for marking articles for identification/authentication purposes. Also provided is a method for invisibly marking such articles and a method for detecting and sorting articles by utilizing the near infrared flourophoric ink or coating compositions.Type: GrantFiled: February 18, 1993Date of Patent: March 8, 1994Assignee: Eastman Kodak CompanyInventors: James J. Krutak, Michael R. Cushman, William W. Parham, Clarence A. Coates, Max A. Weaver, Gabor Patonay
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Patent number: 5290631Abstract: Hydrosoluble/hydrodispersible polyester copolycondensates, well suited for the sizing of textile threads, comprise terephthalate, isophthalate, sulfoaryl dicarboxylate, ethylene glycol and polyoxyethylene glycol recurring structural units, have a glass transition temperature ranging from 15.degree. to 40.degree. C. at 85% relative humidity and the turbidity of aqueous formulations thereof are storage-stable over time; such polyester copolycondensates are conveniently prepared by (i) transesterifying admixture of dimethyl terephthalate, dimethyl sulfoaryl dicarboxylate and ethylene glycol, (ii) introducing isophthalic acid and an additional amount of ethylene glycol into the medium of transesterification and therein directly esterifying same, and (iii) polycondensing the resulting product of transesterification/direct esterification.Type: GrantFiled: October 29, 1992Date of Patent: March 1, 1994Assignee: Rhone-Poulenc ChimieInventors: Etienne Fleury, Yvette Girardeau
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Patent number: 5264477Abstract: In situ formation of a melt processable liquid crystalline polyester composition capable of forming an anisotropic melt phase at a temperature of below approximately 400.degree. C. having an improved heat distortion temperature under a load, the composition being formed in the presence of from approximately 0.05 to approximately 1.0 weight percent of a divalent metal salt of terephthalic acid as a nucleating agent. Films, fibers and molded articles produced from the composition exhibit improved thermal properties.Type: GrantFiled: July 28, 1992Date of Patent: November 23, 1993Assignee: Hoechst Celanese Corp.Inventors: Kurt F. Wissbrun, James P. Shepherd
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Patent number: 5262513Abstract: A copolyester which comprises, as main components, terephthalic acid as a dicarboxylic acid component and ethylene glycol as a diol component and which is characterized by:(1) isophthalic acid as a dicarboxylic acid component being from 0.5 to 3.0 mol %,(2) diethylene glycol as a diol component being from 1.0 to 2.5 mol %,(3) the intrinsic viscosity being from 0.60 to 1.50 dl/g,(4) the concentration of terminal carboxyl groups being at most 18 eq/ton, and(5) the content of a cyclic trimer being at most 0.40% by weight.Type: GrantFiled: July 13, 1992Date of Patent: November 16, 1993Assignee: Mitsubishi Kasei CorporationInventors: Katsuji Tanaka, Hitoshi Matsumoto, Takuji Hirahara, Osamu Kishiro
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Patent number: 5256363Abstract: Polyethylene terephthalates of the present invention are excellent in mechanical strength, heat resistance and transparency, and therefore blow molded containers molded from the present polyethylene terephthalate are excellent in high temperature filling properties when they are filled with juice, refrigerant beverage, carbonated beverage, seasonings, etc. Furthermore, the blow molded containers prepared from the present polyethylene terephthalates have such characteristic features that they are free from thermal deformation at the time when they are subjected to high temperature filling, they are readily subjected to sterilization treatment and hence excellent in high speed filling properties.Type: GrantFiled: December 4, 1992Date of Patent: October 26, 1993Assignee: Mitsui Petrochemical Industries, Ltd.Inventors: Mikio Hashimoto, Hiroji Niimi, Tadao Yatsu, Shigemi Shiraki
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Patent number: 5242645Abstract: A rubber-reinforcing polyester fiber composed of a polyester prepared by using 30 to 150 ppm as antimony of an antimony compound and 5 to 60 ppm as germanium of a germanium compound as the polymerization catalyst. The fiber is characterized in that the terminal carboxyl group content is not larger than 25 eq/ton, diethylene glycol content (DEG) is not larger than 1.3% by weight, the intrinsic viscosity (IV) is at least 0.85, the sum (S) of the intermediate elongation and the dry heat shrinkage is lower than 8%, the product between strength and elongation (T.sqroot.E) is at least (2S+5), and the terminal modulus (TM) is not higher than 40 g/d. The polyester fiber is used as a rubber reinforcement.Type: GrantFiled: September 13, 1991Date of Patent: September 7, 1993Assignee: Toray Industries, Inc.Inventors: Tai Sasamoto, Takehiko Miyoshi, Takuji Sato
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Patent number: 5218042Abstract: Disclosed is a water-dissipatable or dispersible polyester containing sulfonate groups that has improved stability having a substantial number of capped carboxyl groups attached to the sulfomonomer moieties. This polyester can be prepared by capping the carboxyl end groups of the polyester with oxirane compounds or by polymerizing the reactants wherein one reactant is a diol that is a diester adduct of a glycol and a dicarboxylic acid sulfomonomer.Type: GrantFiled: September 25, 1991Date of Patent: June 8, 1993Inventors: Thauming Kuo, Keith M. Moody
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Patent number: 5187216Abstract: Disclosed is a process for the preparation of crystalline copolyesters from substantially amorphous, diethylene glycol-containing copolyesters wherein the a zeolite is incorporated in the substantially amorphous copolyester to promote crystallization upon heating a particulate form of the resulting copolyester at crystallizing effective temperatures.Type: GrantFiled: April 18, 1991Date of Patent: February 16, 1993Assignee: Eastman Kodak CompanyInventors: Michael L. Cassell, Waylon L. Jenkins, Gerry F. Rhodes
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Patent number: 5180793Abstract: The invention is a polyester and a method for producing a polyester filament which has a combination of flame resistance and low pilling properties. The method comprises forming a polyester polymer from a mixture of two polymers, the first compound being the reaction product of terephthalic acid or dimethyl terephthalate, ethylene glycol, and an oxysilicon compound and the second compound being the reaction product of terephthalic acid or dimethyl terephthalate, ethylene glycol and a phosphinic acid in the amount between 0.5 and 20 mole percent of the terephthalate acid and monomer. In particular, the invention also comprises the enhanced fiber formed by the process, as well as the fabrics having a pilling of about 3 to less than 5 as measured in accordance with ASTM D-3512-82.Type: GrantFiled: December 31, 1991Date of Patent: January 19, 1993Assignee: Hoechst Celanese CorporationInventors: Richard E. Vigneault, William S. Wagner, Klaus Weisskopf, R. Edward Williamson, A. John Woodward
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Patent number: 5166310Abstract: Polyesters are prepared from dihydroxyl-containing compounds and di-carboxylic acids or anhydrides or lower alkyl esters thereof in the presence of a combination of tin catalysts comprising (1) at least one organotin salt of a carboxylic acid, and (2) either (a) at least one organotin oxide, or (b) at least one organostannoic acid, or (c) a combination of (a) and (b). The polyesters prepared by this process are useful in coating, adhesive, fiber and molding applications.Type: GrantFiled: August 27, 1991Date of Patent: November 24, 1992Assignee: The Dow Chemical CompanyInventor: Peter C. Rooney
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Patent number: 5143984Abstract: A process for preparing a polyester having an inherent viscosity of at least 0.5 comprising(A) preparing an admixture of a molten polyester having an inherent viscosity of less than 0.5, a titanium alkoxide and a 13X zeolite, and(B) subjecting the admixture to a time and temperature sufficient to increase the inherent viscosity of the polyester to at least 0.5.Type: GrantFiled: January 21, 1992Date of Patent: September 1, 1992Assignee: Eastman Kodak CompanyInventors: Waylon L. Jenkins, Gerry Rhodes, Mark Rule
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Patent number: 5138024Abstract: A copolyester is synthesized by reacting a dialkyl ester of an aromatic dicarboxylic acid (e.g., dimethyl terephthalate) with ethylene glycol, low molecular weight poly(ethylene glycol) and a salt of a sulfonic acid-substituted aromatic dicarboxylate (e.g., sodium sulfoisophthalic acid) simultaneously in a first stage reaction in the presence of a phosphite or phosphate stabilizer. The intermediate product of the first stage is further reacted in a second stage in the presence of a polycondensation catalyst to obtain a random copolyester of the desired molecular weight. The copolyester is extruded to form a film which, after orientation and heat setting, has excellent clarity and is useful as a photographic film support. Aqueous processing of the film relaxes any core set or curl.Type: GrantFiled: January 25, 1991Date of Patent: August 11, 1992Assignee: Eastman Kodak CompanyInventors: Carl T. Brozek, Robert C. Daly, Robert H. Fehnel, Constantine C. Petropoulos
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Patent number: 5132392Abstract: Hydrophilic polyester resin is provided by the method comprising reacting an aromatic dicarboxylic acid or diester thereof, a diol and a polysiloxane-polyether copolymer wherein the polysiloxane backbone is endblocked with a hydroxyl-substituted organic group and the polyether portion of the copolymer comprises polyoxyethylene. The resulting silicone-modified polyester is especially suited for making hydrophilic fiber and film.Type: GrantFiled: December 24, 1991Date of Patent: July 21, 1992Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: Douglas J. DeYoung, Gerald J. Murphy
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Patent number: 5115086Abstract: In one aspect, this invention is a primer which comprises a solution of: (a) a polyester resin of a carboxylic acid and a glycol; and (b) a polymethylene poly(phenyl isocyanate), diphenylmethane diisocyanate, or mixture thereof; in a volatile solvent, wherein the weight ratio of (a):(b) is in the range of from about 0.25:1.0 to 2.0:1.0. In a second aspect, this invention is a primer which comprises a solution of: (a) 5-18 weight percent of a polyester resin of a carboxylic acid and a glycol; and (b) 6-17 weight percent of a polymethylene poly(phenyl isocyanate), diphenylmethane diisocyanate, or mixture thereof; in a volatile solvent. It has been discovered that the primer of the invention advantageously provides improved adhesion characteristics of metal-to-glass bonding when used to prime paint-coated metal substrates before the application of a urethane adhesive, particularly when used with a "fast cure" adhesive comprised of an isocyanate-functional prepolymer and dimorpholinediethyl ether.Type: GrantFiled: February 6, 1990Date of Patent: May 19, 1992Assignee: Essex Specialty Products, Inc.Inventor: Harry W. S. Hsieh
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Patent number: 5106941Abstract: A process for preparing a crystalline poly(cyclohexanedimethylene terephthalate) comprising(A) preparing an admixture of molten poly(cyclohexanedimethylene terephthalate) and a 4A zeolite, and(b) cooling the admixture at a rate less than about 1000.degree. C. per minute to a temperature less than about 80.degree. C.Type: GrantFiled: June 24, 1991Date of Patent: April 21, 1992Inventors: Waylon L. Jenkins, Gerry F. Rhodes, Mark Rule
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Patent number: 5104965Abstract: A process for preparing a crystalline poly(ethylene terephthalate) having an inherent viscosity of at least 0.5 comprising(A) preparing an admixture of molten poly(ethylene terephthalate) and a zeolite, and(B) cooling the admixture at a rate less than about 300 degrees C. per minute to a temperature less than about 80 degrees C.Type: GrantFiled: February 22, 1991Date of Patent: April 14, 1992Assignee: Eastman Kodak CompanyInventors: Waylon L. Jenkins, Gerry F. Rhodes, Mark Rule
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Patent number: 5089598Abstract: Silane esters are transesterified with hydroxyl-terminated polyester resins to obtain end-capped, extended or branched polyester molding compositions.Type: GrantFiled: October 5, 1990Date of Patent: February 18, 1992Assignee: General Electric CompanyInventors: Christopher M. Hawkins, Edgar E. Bostick, James L. Derudder
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Patent number: 5015759Abstract: A process for increasing the direct esterification reaction rate between a diacid and 1,4-butanediol and for directly esterifying greater than 95% of the acid ends of the diacid by mixing in any order the diacid, the 1,4-butanediol and a catalyst compound selected from organo-titanium, organo-tin, and organo-zirconium compounds, to form a reaction mixture wherein the ratio of diol:diacid is at least 2:1 and then reacting the reaction mixture at an average temperature ranging between 190.degree. C. to 200.degree. C. for a period of time no longer than sixty minutes. The same process may be followed substituting ethylene glycol for 1,4-butanediol, provided the catalyst compound is added neat, further provided that the average reaction temperature ranges from 190.degree. C. to 200.degree. C., and also provided that the reaction mixture be reacted for a period of time no longer than seventy minutes.Type: GrantFiled: December 8, 1989Date of Patent: May 14, 1991Assignee: E. I. Du Pont de Nemours and CompanyInventor: David J. Lowe
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Patent number: 5008366Abstract: A process is disclosed for preparing adhesives from polyethylene terephthalate which comprises reacting a trimellitic acid polyester ether with polyethylene terephthalate to prepare a nonlinear copolymer with crosslinking characteristics suitable for use as an adhesive either as a hot-melt adhesive or as a pressure-sensitive adhesive.Type: GrantFiled: April 25, 1990Date of Patent: April 16, 1991Assignee: Amoco CorporationInventor: Oscar M. Bathe
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Patent number: 4988793Abstract: Disclosed are thermosetting, powder coating compositions comprised of certain novel polyesters comprised of residues of terephthalic acid and 1,3-bis(2-hydroxyethoxy)benzene in combination with a blocked polyisocyanate which, when applied to a substrate and heated, provide cross-linked coatings having a combination of desirable properties including good gloss, impact strength and flexibility.Type: GrantFiled: May 23, 1989Date of Patent: January 29, 1991Assignee: Eastman Kodak CompanyInventors: Robert B. Barbee, Brian S. Phillips
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Patent number: 4978741Abstract: A method of producing essentially haze-free isophthalic acid and polymethylolalkanoic acid-containing resins comprising reacting isophthalic acid, a polymethylolalkanoic acid, and a polyol in the presence of a catalytically effective amount of a catalyst selected from the group consisting of stannous oxalate, dibutyltin oxide, and tetrabutyl titanate at a temperature of between about 150.degree. C. and 230.degree. C. to produce haze-free resin.Type: GrantFiled: December 15, 1989Date of Patent: December 18, 1990Assignee: Questra Chemicals Corp.Inventor: Paul E. Eckler
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Patent number: 4973646Abstract: Disclosed are thermosetting, powder coating compositions comprised of semi-crystalline polyesters and .epsilon.-caprolactam-blocked bis(1-cyanato-1-methylethyl) benzene compounds which are readily curable at relatively-mild temperatures and using cure times commonly used to cure (cross-link) powder coatings. When using equivalent curing conditions, the disclosed coating compositions exhibit a higher degree of cross-linking than do combinations of amorphous polyesters and the .epsilon.-caprolactam-blocked bis(1-cyanato-1-methylethyl)-benzene compounds.Type: GrantFiled: April 9, 1990Date of Patent: November 27, 1990Assignee: Eastman Kodak CompanyInventors: Jonathan S. Witzeman, Yeong-Ho Chang
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Patent number: 4970288Abstract: Non-toxic organotin catalysts containing at least one direct oxygen-to-tin bond and one direct carbon-to-tin bond are provided for use as esterification catalysts in the production of non-toxic polyester and polyester-containing compositions. Articles made from such polyester and polyester-containing compositions are suitable for use in regulated food, beverage, pharmaceutical, and medical-device applications.Type: GrantFiled: September 22, 1989Date of Patent: November 13, 1990Assignee: Atochem North America, Inc.Inventors: William A. Larkin, Emily C. Bossert, Edmund M. Gibbons
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Patent number: 4968776Abstract: The sizing agent according to the present invention contains as the essential component a high molecular compound having an weight-average molecular weight of not less than 20,000 prepared by reacting(A) a polyhydroxy compound having an weight-average molecular weight of not less than 1,000, which is prepared by an addition polymerization of ethylene oxide or alkylene oxides comprising ethylene oxide to an organic compound having two active hydrogens, with(B) a polycarboxylic acid, a polycarboxylic acid anhydride or a lower ester of a polycarboxylic acid.Type: GrantFiled: October 24, 1989Date of Patent: November 6, 1990Assignee: Dai-Ichi Kogyo Seiyaku Co., Ltd.Inventors: Takeshi Fujita, Tadayuki Sugimoto, Kazuyo Aketa
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Patent number: 4921929Abstract: Isophthalic acid is commonly utilized as a comonomer in the preparation of copolyester resins which are utilized as solution adhesives. Unfortunately, solutions of such resins frequently become hazy due to the presence of cyclic oligomers. This invention is based upon the unexpected discovery that the presence of protonic acids during the synthesis of the copolyester resins containing isophthalic acid utilizing conventional metallic catalysts results in solutions of the resins in organic solvents being virtually haze free.Type: GrantFiled: March 28, 1989Date of Patent: May 1, 1990Assignee: The Goodyear Tire & Rubber CompanyInventors: John R. Wilson, Marian M. Rousek, Fred L. Massey
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Patent number: 4818808Abstract: A process for producing a linear polyester comprising a main structural unit of an aromatic dicarboxylic acid ester of an alkylene glycol, particularly, comprising a polyethylene terephthalate or polytetramethylene terephthalate unit, is provided. In the process of the invention, the polycondensation reaction is conducted in the presence of a niobic acid catalyst that is obtained by heat-treating a hydrated niobium compound at the temperature range between 80.degree. C. and 400.degree. C. The process of the invention is also effecitvely applied to the manufacture of an elastomeric polyester comprising a polyalkylene terephthalate as a hard segment and a polyalkylene glycol as a soft segment.Type: GrantFiled: March 24, 1988Date of Patent: April 4, 1989Assignees: Kanebo, Ltd., Research Association for Synthetic Fiber TechnologyInventors: Toshihiro Kushimoto, Yoshimichi Ozawa, Nobuo Izawa
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Patent number: 4804730Abstract: Condensation polymers of high molecular weight, such as polyesters, polyureas, and polyamides, are usually prepared at temperatures of 200.degree. C. or greater. However, by utilizing the catalyst systems of the present invention, condensation polymers can be synthesized at much lower temperatures. The polycondensation catalyst systems of the present invention are particularly useful for synthesizing aliphatic polyesters, such as polyethylene terephthalate, from dicarboxylic acids and aliphatic glycols. The present invention more specifically discloses a process for the synthesis of an aliphatic polyester comprising polymerizing at least one dicarboxylic acid with at least one aliphatic glycol in the presence of (1) at least one phosphorus containing compound which contains at least one trivalent or pentavalent phosphorus atom which is bonded directly to at least one phenyl group, (2) an acid acceptor, and (3) at least one halogenated oganic compound.Type: GrantFiled: February 5, 1987Date of Patent: February 14, 1989Assignee: The Goodyear Tire & Rubber CompanyInventor: Naoya Ogata
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Patent number: 4780527Abstract: Poly(butylene terephthalate) is prepared in a two-stage process wherein terephthalic acid and 1,4-butanediol are esterified in the presence of a catalytic amount of a catalyst having an organo-metallic component which is an organo-titanate compound, an organo-tin compound or a combination thereof and a salt component which is an organic acid salt or an inorganic salt. In a second step, the esterification product is subject to polycondensation. By following the foregoing procedure, the formation of tetrahydrofuran is significantly suppressed and the percent conversion of esterification products increased.Type: GrantFiled: May 6, 1987Date of Patent: October 25, 1988Assignee: Industrial Technology Research InstituteInventors: Shen-Nan Tong, Mei-Sui Chen, Wu-Bin Yuo, Nien-Hsi Chang
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Patent number: 4727133Abstract: Hydrolysis-stable, thermoplastic block polyetheresteramides are produced by a catalyzed polycondensation of linear, aliphatic polyamides having carboxyl end groups with .alpha.,.omega.-dihydroxypolyethers and additionally, a linear or branched, aliphatic or cycloaliphatic diol having 2-8 carbon atoms in an amount of 3-30 mol %, relative to the sum of the moles of both other starting materials. The ratio of the moles of the polyamide components to the sum of the moles of the dihydroxypolyether and diol components is 0.81 to 0.985.Type: GrantFiled: February 5, 1986Date of Patent: February 23, 1988Assignee: Inventa AG Fur Forschung und PatentverwertungInventor: Hanns-Jorg Liedloff