Non-1,2-epoxy Or Nonphenolic Reactant Is A Carboxylic Acid, Salt Thereof, Or Carboxylic Acid Anhydride Patents (Class 528/112)
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Patent number: 6268055Abstract: Described are photochromic epoxy resin coatings that meet commercially acceptable “cosmetic” standards for optical coatings. Also described are articles having such coatings. The coatings exhibit a Fischer microhardness of from 50 to 150 Newtons per mm2 and desirable photochromic properties, i.e., the formation of darker activated colors and faster rates of photochromic activation and fade when irradiated with ultraviolet light.Type: GrantFiled: November 6, 1998Date of Patent: July 31, 2001Assignee: PPG Industries Ohio, Inc.Inventors: Robert W. Walters, Cletus N. Welch, John W. Burgman, Debra L. Singer, Shanti Swarup
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Patent number: 6262189Abstract: The invention provides for a process for the preparation of an advanced epoxy resin by reaction of a compound having on average more than one epoxy group per molecule and a compound having on average one or more hydroxyl group or carboxyl group per molecule in the presence of a catalyst at elevated temperature, the process comprising (1) mixing the epoxy compound, the hydroxyl compound or the carboxyl compound and the catalyst, and (2) transferring the mixture as a feedstream to a surface which is at least intermittently moving with respect to the feedstream. In a preferred embodiment an endless conveyer belt with additional heating means and optional cooling means are used.Type: GrantFiled: September 16, 1999Date of Patent: July 17, 2001Assignee: Shell Oil CompanyInventors: Johannes Petrus Jozef Beerepoot, Johannes Jozias Blom, Feike De Jong, Wilhelmina Johanna Maria Van Der Linden-Lemmers, Willem Sjardijn, Virgilius Christiaan Johannes Nicolaas Van Liempd, Paulus Egidius Raas
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Patent number: 6194490Abstract: A composition, which comprises (a) a compound containing at least one epoxy group in inner position per molecule, obtained by epoxidation of a natural unsaturated oil or of its derivative; (b) an epoxy compound selected from the group consisting of glycidyl ethers, glycidyl esters and cycloaliphatic epoxides; (c) a polycarboxylic acid anhydride; (d) a compound of formula I, I, III or IV or an acid adduct of a compound of formula I, II, III or IV wherein R1 to R4 are each independently of one another hydrogen; C1-C18alkyl which is unsubstituted or substituted by one or more than one hydroxyl group amino group, halogen atom, cyano group, C1-C6alkoxy group or C1-C6cyanalkoxy group; C5-C14aryl, C6-C24aralkyl, C3-C14heteroaryl or C4-C14heteroaralkyl which are unsubstituted or substituted by one or more than one C1-C6alkyl group, C1-C6alkoxy group or halogen atom, n is an integer from 1 to 3, and R5 and R6 are each independently of the other C1-C6alkyl or, together with theType: GrantFiled: February 19, 1999Date of Patent: February 27, 2001Assignee: Vantico, Inc.Inventors: Martin Roth, Qian Tang, Roger Malherbe, Catherine Schoenenberger
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Patent number: 6169158Abstract: The present invention is directed to a polyglycidyl compound having on average more than two, preferably more than two and a half, particularly preferably more than three, glycidyl groups per molecule and a Tg value (determined by DSC, heating rate=20° C./min) higher than 20° C.Type: GrantFiled: April 23, 1999Date of Patent: January 2, 2001Assignee: Vantico, Inc.Inventors: Christoph Rickert, Hugh Stephen Laver
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Patent number: 6120889Abstract: The invention relates to an amorphous copolyester having a maximum melt viscosity at 1 radian/second and at about 260 to about 290.degree. C. of about 12000 poise, a glass transition temperature ranging from about 88.degree. C. to about 120.degree. C., and an inherent viscosity of at least about 0.6 dl/g. The amorphous copolyesters comprise the reaction product of a diol component and a dicarboxylic acid component. The diol component comprises residues of from about 5.0 to about 50 mole % of 2,2'-(sulfonylbis(4,1 -phenyleneoxy))-bis(ethanol) which has the following chemical formula: ##STR1## and from about 50 to about 95 mole % of a mixture of at least two diols selected from the group consisting of ethylene glycol, neopentyl glycol, 1,3-propanediol, 1,4-butanediol, 1,4-cyclohexanedimethanol, and mixture thereof. The dicarboxylic acid component comprises residues of terephthalic acid, isophthalic acid, 1,4-cyclohexandedicarboxylic acid, 2,6-naphthalene dicarboxylic acid and mixtures thereof.Type: GrantFiled: June 3, 1999Date of Patent: September 19, 2000Assignee: Eastman Chemical CompanyInventors: S. Richard Turner, Bobby J. Sublett
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Patent number: 6077879Abstract: The present invention provides a radically polymerizable curable resin obtained by modifying an epoxy resin by reacting a phenol compound having an alcoholic hydroxyl group; and an unsaturated monobasic acid, to the epoxy resin having two or more epoxy groups in a molecule. The epoxy resin is reacted with the phenol compound and the unsaturated monobasic acid. The curable resin is subjected to polymerization curing with heat or light to form a cured product having excellent heat resistance, moisture resistance, and adhesion to substrates. The present invention also provides a curable resin composition containing the curable resin, as well as an alkaline-developable curable resin capable of forming a coating layer having excellent tack-free property, quick developability and excellent properties of cured layer.Type: GrantFiled: November 10, 1998Date of Patent: June 20, 2000Assignee: Nippon Shokubai Co., Ltd.Inventors: Nobuaki Ohtsuki, Toshio Awaji
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Patent number: 6075099Abstract: A curable epoxidized polyester-based composition useful for powder coatings application is provided by epoxidizing a polyester having a melting point of at least 90.degree. C. and a viscosity of at most 50 Poise@ 200.degree. C., where such polyester is a polyester prepared by reacting (I) a tetrahydrophthalic acid or anhydride, (ii) at least one cycloaliphatic polyol, (iii) at least one saturated polycarboxylic acid, and (iv) optionally at least one other alcohol under conditions effective to obtain a solid polyester having a melting point of at least 90.degree. C. Curable coating powder is obtained containing the epoxidized polyester and a solid carboxylic acid curing agent having an acid equivalent weight within the range of from about 100 to about 1500.Type: GrantFiled: February 6, 1996Date of Patent: June 13, 2000Assignee: Shell Oil CompanyInventors: Charles John Stark, Edward John Marx
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Patent number: 6040397Abstract: A single component, extremely low viscosity, pre-catalyzed high functionality diepoxide and epoxy resin system has been developed. This resin system has good thermal stability, an extended work life and is capable of being refrigerated to -18 C. and stored for extended periods of time with little or no change in physical or mechanical properties. The resin system has direct applications in a number of industries including, but not limited to, the aircraft and spacecraft industries. The resin system is a mixture of specific epoxy resins and curing agents that when combined form an extremely low viscosity resinous system that may be readily cured at a temperature as low as 52 degrees C. into novel thermoset materials prepared therefrom, which are characterized by superior strength properties and methods for preparing the same.Type: GrantFiled: July 6, 1998Date of Patent: March 21, 2000Assignee: Lockheed Martin CorporationInventors: James R. Hooper, Richard K. Strother, John Fish, Paul G. Pawling, Gerald L. Sauer
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Patent number: 6037425Abstract: The present invention provides an epoxy resin composition useful for casting applications, comprising a reaction product obtained by reacting (A) a bisphenol epoxy resin, and (B) bisphenol compounds, and if necessary, (C) monofunctional phenols or carboxylic acid compounds, in the presence of sodium compounds, wherein the epoxy resin composition has(a) an epoxy equivalent: 250 to 500 g/equivalent,(b) a sodium content: 20 to 200 ppm, and(c) a haze of its 40 wt % methyl ethyl ketone solution measured according to ASTM D 1003: 15% or less.Type: GrantFiled: November 21, 1996Date of Patent: March 14, 2000Assignee: Shell Oil CompanyInventors: Takao Fukuzawa, Tetsuro Imura, Masayuki Ohta
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Patent number: 6022931Abstract: The invention provides for a process for the preparation of an advanced epoxy resin by reaction of a compound having on average more than one epoxy group per molecule and a compound having on average one or more hydroxyl group or carboxyl group per molecule in the presence of a catalyst at elevated temperature, the process comprising (1) mixing the epoxy compound, the hydroxyl compound or the carboxyl compound and the catalyst, and (2) transferring the mixture as a feedstream to a surface exposed to an elevated temperature sufficient to produce an advanced epoxy resin which is at least intermittently moving with respect to the feedstream. In a preferred embodiment an endless conveyer belt with additional heating means and optional cooling means are used.Type: GrantFiled: July 17, 1998Date of Patent: February 8, 2000Assignee: Shell Oil CompanyInventors: Johannes Petrus Jozef Beerepoot, Johannes Jozias Blom, Feike De Jong, Wilhelmina Johanna Maria Van Der Linden-Lemmers, Willem Sjardijn, Virgilius Christiaan Johannes Nicolaas Van Liempd, Paulus Egidius Raas
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Patent number: 5985043Abstract: A thermally curable adhesive composition that includes a fluxing agent that also acts as an adhesive is provided. The composition includes: (a) a fluxing agent represented by the formula RCOOH, wherein R comprises a moiety having two or more carbon--carbon double bonds; (b) optionally, an effective amount of a crosslinkable diluent; (c) optionally, an effective amount of a source of free radical initiators; and (d) optionally, an effective amount of a resin to react with remnant carboxylic acid moieties. The composition can be applied directly onto the surface(s) of devices that are to be joined electrically and mechanically. These devices include, printed circuit substrates, connectors, components, cables, and other electrical devices having metallization patterns to be soldered together by means of a solder-bumped pattern on one or both surfaces. Alternatively, a solder paste, comprising solder powder mixed with the fluxing agent of the present invention can be used.Type: GrantFiled: July 21, 1997Date of Patent: November 16, 1999Assignee: Miguel Albert CapoteInventors: Zhiming Zhou, Miguel A. Capote
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Patent number: 5985456Abstract: A thermally curable adhesive composition that includes a fluxing agent that also acts as an adhesive is provided. The composition includes: (a) a fluxing agent represented by the formula RCOOH, wherein R comprises a moiety having two or more carbon-carbon double bonds wherein in one embodiment, at least one is within an acrylate or methacrylate group, and which may further contain at least one aromatic moiety; (b) optionally, an effective amount of a crosslinkable diluent; (c) optionally, an effective amount of a source of free radical initiators; and (d) optionally, an effective amount of a resin to react with remnant carboxylic acid moieties. By employing an acrylate, methacrylate, or phenol in the structure of the adhesive flux, the cure temperature and moisture absorption characteristics can be significantly improved. The composition can be applied directly onto the surface(s) of devices that are to be joined electrically and mechanically.Type: GrantFiled: September 9, 1997Date of Patent: November 16, 1999Assignee: Miguel Albert CapoteInventors: Zhiming Zhou, Miguel A. Capote
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Patent number: 5969059Abstract: An impregnation resin composition comprising an alicyclic epoxy compound, an acid anhydride, an aluminum compound having an organic group, and butylglycidyl ether, wherein the alicyclic epoxy compound contains not more than 30 ppm in concentration of Na ion component.Type: GrantFiled: March 13, 1998Date of Patent: October 19, 1999Assignee: Kabushiki Kaisha ToshibaInventors: Shinji Murai, Shuji Hayase
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Patent number: 5932656Abstract: A process for curing epoxidized diene polymers for use in adhesives, sealants, and coatings which comprises contacting the polymer with an aromatic anhydride curing agent at an epoxy/anhydride molar ratio from 0.5/1 to 2.0/1.0, optionally, and from 0.1 to 10 phr of an accelerator at a temperature of from 100 to for a period of 10 minutes to six hours.Type: GrantFiled: November 20, 1997Date of Patent: August 3, 1999Assignee: Shell Oil CompanyInventor: Michael Alan Masse
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Patent number: 5932682Abstract: A cleavable epoxy resin composition suitable for encapsulating electronic chips and a method for making the composition comprises the cured reaction product of a diepoxide; a cyclic dicarboxylic anhydride curing agent mixture; a 1,3-diaza compound having two nitrogen atoms present with one nitrogen atom doubly bonded to the central carbon and singly bonded to one other carbon, and the other nitrogen atom singly bonded to the central carbon and singly bonded to another carbon and singly bonded to a hydrogen. The 1,3-diaza compound serves either as the sole catalyst or in combination with a tertiary amine catalyst different from the diaza compound. The composition may include an optional hydroxy functional compound capable of reacting with the cyclic anhydrides to form a half ester thereby initiating the reaction between the diepoxide and the cyclic dicarboxylic anhydride curing agent. The resin can be used for the encapsulation of electronic parts, but can be removed by a solvent.Type: GrantFiled: December 19, 1995Date of Patent: August 3, 1999Assignee: International Business Machines CorporationInventors: Stephen Leslie Buchwalter, Joseph Paul Kuczynski, John Gregory Stephanie
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Patent number: 5910548Abstract: The process for producing a modified epoxy resin comprises reacting (a) an epoxy resin having at least two epoxy groups per one molecule, and (b) a specific active ester group-containing compound having at least two aromatic ring-bonded active ester groups per one molecule, in proportions such that the amount of the active ester groups in the active ester group-containing compound is from about 0.05 to about 0.95 mol per mole of the epoxy group in the epoxy resin, and the modified epoxy obtained by this process, and a composition of the epoxy resin and a curing agent are encompassed.Type: GrantFiled: July 22, 1997Date of Patent: June 8, 1999Assignee: Shell Oil CompanyInventors: Yasuyuki Murata, Norio Tohriiwa, Yoshinori Nakanishi
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Patent number: 5904888Abstract: A two-component system for producing two or more different curable mixtures in which the first component A is common to each mixture and comprises:1. a liquid epoxy2. an acid anhydride hardener and3. at least one fillerand the second component B is selected from two or more different components B, each of which comprises:1. an accelerator, and optionally2. a colourant, and optionally3. a non-volatile solvent/extender for the accelerator4. a flexibiliser for the epoxy-anhydride cure5. a acid anhydride hardener.Type: GrantFiled: December 18, 1997Date of Patent: May 18, 1999Assignee: Ciba Specialty Chemicals CorporationInventors: Barry James Hayes, Paul Terrence Wombwell, Philip David Willis
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Patent number: 5844048Abstract: Thermosetting powder coatings based on epoxide-containing acrylate copolymer resins are disclosed comprising:(A) an acrylate copolymer that contains glycidyl ether residues;(B) an aliphatic and/or cycloaliphatic polybasic acid and/or a polyol-modified anhydride of a polybasic acid and/or an amorphous or semi-crystalline carboxy-functional copolyester resin and/or a carboxy-functional acrylic resin;(C) and, optionally, fillers and/or pigments and/or additives wherein the acrylate copolymer (A) has a molecular weight (Mw) of 1,000 to 30,000 and a glass transition temperature of 20.degree. to 120.degree. C. and is obtainable by, in a first step, preparing a hydroxyl-functional acrylate copolymer (D), which copolymer is then transformed into the acrylate copolymer (A), by reaction with epihaloalkanes.The aforementioned compositions can be processed further to give thermosetting powder coatings which can be applied to substrates such as metal to form protective coatings or films.Type: GrantFiled: March 26, 1996Date of Patent: December 1, 1998Assignee: Ems-Inventa AGInventors: Andreas Kaplan, Rene Gisler, Albert Reich
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Patent number: 5824752Abstract: The invention provides for a process for the preparation of an advanced resin by reaction of a compound having on average more than one epoxy group per molecule and a compound having on average one or more hydroxyl group or carboxyl group per molecule in the presence of a catalyst at elevated temperature, the process comprising (1) mixing the epoxy compound, the hydroxyl compound or the carboxyl compound and the catalyst, and (2) transferring the mixture as a feedstream to a surface exposed to an elevated temperature sufficient to produce an advanced epoxy resin which is at least intermittently moving with respect to the feedstream. In a preferred embodiment an endless conveyer belt with additional heating means and optional cooling means are used.Type: GrantFiled: April 18, 1997Date of Patent: October 20, 1998Assignee: Shell Oil CompanyInventors: Johannes Petrus JozeF Beerepoot, Johannes Jozias Blom, Feike De Jong, Wilhelmina Johanna Maria Van Der Linden-Lemmers, Willem Sjardijn, Virgilius Christiaan Johannes Nicolaas Van Liempd, Paulus Egidius Raas
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Patent number: 5760162Abstract: In a process for the preparation of poly-o-hydroxyamides and poly-o-mercaptoamides, a bis-o-aminophenol or a bis-o-aminothiophenol is reacted at a temperature of .ltoreq.0.degree. C. with a mixed dianhydride of a dicarboxylic acid and a sulfonic acid with the following structure:E--SO.sub.2 --O--CO--R*--CO--O--SO.sub.2 --Ewhere E is an (optionally substituted) methyl, phenyl, or naphthyl group and R* is the parent body of the dicarboxylic acid.Type: GrantFiled: August 27, 1996Date of Patent: June 2, 1998Assignee: Siemens AktiengesellschaftInventors: Recai Sezi, Hellmut Ahne, Roland Gestigkeit, Kurt Geibel
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Patent number: 5741856Abstract: A process for curing epoxidized diene polymers for use in adhesives, sealants, and coatings which comprises contacting the polymer with an aromatic anhydride curing agent at an epoxy/anhydride molar ratio from 0.5/1 to 2.0/1.0, optionally, and from 0.1 to 10 phr of an accelerator at a temperature of from 100.degree. to 200.degree. C. for a period of 10 minutes to six hours.Type: GrantFiled: February 10, 1997Date of Patent: April 21, 1998Assignee: Shell Oil CompanyInventor: Michael Alan Masse
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Patent number: 5736196Abstract: A coating powder based on an epoxy resin is applied to a substrate and fused and cured thereon. Curing is effected by exposing the coating powder at the point of application to a fluid curative or cure catalyst, e.g., by exposing the fusing coating powder to an ammonia-containing atmosphere.Type: GrantFiled: October 2, 1996Date of Patent: April 7, 1998Assignee: Morton International, Inc.Inventors: Owen H. Decker, Dieter W. Jungclaus, Karl R. Wursthorn, Glenn D. Correll, David A. Mountz
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Patent number: 5710234Abstract: Ortho spiroesters of excellent heat resistance and low volume shrinkage during curing are disclosed. Resin compositions of excellent heat resistance and low curing shrinkage containing these ortho spiroesters are also provided. These photosensitive or heat-curable resin compositions are formulated from photo- or heat-polymerizable compounds containing ethylenic double bonds and carboxyl groups, photopolymerization initiators and sensitizers, or polymerization initiators which generate radicals by heat, and said ortho spiroesters. These resin compositions have low curing shrinkage and are useful for applications requiring dimensional accuracy such as molding materials, encapsulants, adhesives and coatings and also for the preparation of image-forming materials such as protective films for color filters, inks and electrically insulating spacers for touch panels.Type: GrantFiled: January 19, 1996Date of Patent: January 20, 1998Assignees: Nippon Steel Chemical Co., Ltd., Nippon Steel CorporationInventors: Koichi Fujishiro, Masaya Furukawa, Kazuhiro Watanabe, Takero Teramoto
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Patent number: 5708120Abstract: The present invention relates to an epoxy composition that is isolated in the form of an infusible, gelled, heat curable, epoxy functional reaction product. The reaction product is formed by mixing together: (A) one or more epoxy resins or epoxy group containing compounds and (B) a hardener system which will react with (A) to give a gelled solid, but which does not cause complete curing of (A) under the reaction conditions chosen for reaction of (A) and (B) to give a gelled solid. The reaction product can be formed by including (C) an optional further hardener system for (A) and the reaction product of (A) and (B), which is different from (B), and which remains largely unreacted with (A) and (B) under said reaction conditions. The present invention further relates to a cured product of said epoxy composition.Type: GrantFiled: January 25, 1996Date of Patent: January 13, 1998Assignee: Ciba Specialty Chemicals CorporationInventor: Peter Drummond Boys White
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Patent number: 5702820Abstract: There is disclosed a photo-imaging resist ink containing (A) an unsaturated group-containing polycarboxylic acid resin which is a reaction product of (c) succinic anhydride with an additive reaction product of (a) an epoxy resin with (b) an unsaturated group-containing monocarboxylic acid, wherein (a) the epoxy resin is represented by the following formula (1): ##STR1## wherein M stands for ##STR2## n is at least 1 on the average; and m is 1 to n on the average. The resist ink is excellent in developability and photosensitivity, while the cured product thereof is excellent in flex resistance and folding resistance, and well satisfactory in adhesion, pencil hardness, solvent resistance, acid resistance, heat resistance, etc.Type: GrantFiled: June 10, 1996Date of Patent: December 30, 1997Assignees: Nippon Kayaku Kabushiki Kaisha, Nippon Polytech Corp.Inventors: Minoru Yokoshima, Tetsuo Ohkubo, Kazunori Sasahara, Yoneji Sato, Yoko Baba
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Patent number: 5650477Abstract: Liquid reactive thermosetting compositions comprising:A) At least one polyepoxide or a mixture of one or more polyepoxides with at least one monoepoxide, of an aliphatic, cycloaliphatic or mixed nature;B) at least one anhydride of a di- or polycarboxylic acid of an aliphatic, cycloaliphatic or mixed nature;C) at least one catalyst capable of promoting the rapid polymerization of the mixture A+B under microwave irradiation and having general formula (I):N.tbd.C--CH.sub.2 --CH(Z)--(O).sub.r --Y.sup.+ NR.sub.1 R.sub.2 R.sub.3 X.sup.-.Type: GrantFiled: December 11, 1995Date of Patent: July 22, 1997Assignee: Enichem S.p.A.Inventors: Fabrizio Parodi, Renata Gerbelli, Mark DeMeuse
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Patent number: 5623031Abstract: A modified liquid epoxy resin composition is provided by reacting a crystalline epoxy resin, from about 3 to about 20 parts by weight, based on the epoxy resin, of a compound having two or more phenolic hydroxyl groups and/or carboxyl groups in one molecule and from about 3 to about 20 parts by weight of a compound having one phenolic hydroxyl group or carboxyl group in one molecule. The crystalline epoxy resin is preferably selected from various glycidylethers of biphenol compounds. The modified liquid epoxy resin composition has a low viscosity and good liquid stability at low temperatures, resulting in cured resins having excellent heat resistance and water resistance.Type: GrantFiled: January 11, 1996Date of Patent: April 22, 1997Assignee: Shell Oil CompanyInventors: Tetsuro Imura, Yasuyuki Murata, Yoshinori Nakanishi
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Patent number: 5616658Abstract: A curing agent for a composition useful for the production of matt epoxy resin and hybrid powder coatings, comprising a mixture ofa) salts of phthalic acid, isophthalic acid and terephthalic acid with the following amines ##STR1## in which R.sub.1, R.sub.2 and R.sub.3 are identical or different aliphatic, cycloaliphatic, araliphatic or aromatic hydrocarbon radicals having 1-20 carbon atoms and in which one or more CH.sub.2 groups in the carbon chain may be replaced by 0 atoms, by NR.sub.4 groups where R.sub.4 =C.sub.1-6 -alkyl, CH--OH groups, and/or one or more terminal methyl groups may be replaced by dialkyl-substituted amino groups having 1 to 6 carbon atoms, and R.sub.1 and R.sub.2 may form a joint ring in which one CH.sub.2 group may be replaced by an O atom or by an NR.sub.4 group, and R.sub.1 =R.sub.2 =R.sub.3 --CH.sub.2 --CH.sub.2 -- attached via a common nitrogen atom, and n=3-11, and 0.5-2 mol of amine A)-C) per mole of acid, andb) pyromellitic acid and/or trimellitic acid, 0.Type: GrantFiled: January 10, 1995Date of Patent: April 1, 1997Assignee: Huels AktiengesellschaftInventors: Rainer Gras, Elmar Wolf
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Patent number: 5614126Abstract: The invention relates to a substantially solventless curable resin composition, in particular for the fabrication of prepregs, which contains more than 45% by weight of substances which are solid at ambient temperature at least or at lower temperature, and which, in addition to comprising customary modifiers, comprises solid epoxy resins or a mixture of liquid and solid epoxy resins, at least one initiator which is sensitive to UV radiation for the polymerisation of the epoxy resins and has the formula I ##STR1## wherein a and b are each independently of the other 1 or 2, R.sup.1 ist a .pi.-arene, R.sup.2 is a .pi.-arene, an indenyl anion or a cyclopentadienyl anion, [X].sup..crclbar. is an anion [LQ.sub.m ].sup..crclbar.Type: GrantFiled: May 24, 1995Date of Patent: March 25, 1997Assignee: Ciba-Geigy CorporationInventors: Urs Gruber, Aloysius H. Manser
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Patent number: 5589554Abstract: An adhesive composition is here disclosed which comprises a 2-cyanoacrylate and at least one of compounds (a) and (b):(a) an addition reaction product of an epoxy group and a compound having a cyano group and a carboxylic acid group in its molecule, and(b) a compound having a cyano group and a carboxylic acid group in its molecule. A process for preparing the adhesive composition is also disclosed herein. According to the present invention, the 2-cyanoacrylate-based adhesive composition can be obtained which is excellent in storage stability and hardening properties of thick films and which has a high hardening rate and remarkably improved surface hardening properties of the adhesive composition itself bulged from between adherends. Particularly, the 2-cyanoacrylate bulged from between the adherends can harden rapidly, so that the vaporization of the 2-cyanoacrylate can be minimized.Type: GrantFiled: September 16, 1994Date of Patent: December 31, 1996Assignee: Three Bond Co., Ltd.Inventor: Soichiro Hiraoka
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Patent number: 5583187Abstract: Hot melt adhesive compositions, particularly biodegradable hot melt adhesives are prepared from 10 to 90% by weight of a thermoplastic methylol polyester prepared from the reaction of at least one dicarboxylic acid with a diglycidyl ether, a diglycidyl ester or a combination thereof; 0 to 90% by weight of a compatible tackifier; 0 to 80% by weight of a compatible plasticizer; 0 to 50% by weight of a compatible wax diluent and 0 to 3% by weight of a stabilizer.Type: GrantFiled: May 3, 1995Date of Patent: December 10, 1996Assignee: National Starch and Chemical Investment Holding CorporationInventors: Matthew L. Sharak, Charles W. Paul, Dilip Ray-Chaudhuri
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Patent number: 5576399Abstract: Novel epoxy acrylates and carboxyl group-containing epoxy acrylates of formulae II and III of the claims that are relatively highmolecular and are chemically crosslinkable can be used in photoresist formulations with the additional use of highly polymerized polymer binders. Such resist formulations are used in particular in the field of printed circuit boards and printing plates, are applicable from aqueous medium, are almost tack-free and have very good edge coverage, especially on conductors.Type: GrantFiled: June 28, 1994Date of Patent: November 19, 1996Assignee: Ciba-Geigy CorporationInventors: Martin Roth, Roger Salvin, Kurt Meier, Bernhard Sailer, Rolf Wiesendanger
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Patent number: 5567781Abstract: A liquid coating composition particularly adapted for coating cans. The composition comprises a curable, hydroxyl functional block copolymer which is the reaction product of a 1,2-epoxy resin and a carboxyl functional polyester resin, and a hydroxyl-reactive crosslinking agent providing desirably at least 2.0 equivalents of hydroxyl reactive functional groups per hydroxyl equivalent of the block copolymer. The block copolymer desirably has a number average molecular weight in the range of 7000 to 30,000. Also disclosed is a method for formulating a coating composition utilizing craze resistance testing over an aging period to enable the choice of the quantity of curing agent to be used in the coating composition.Type: GrantFiled: June 7, 1995Date of Patent: October 22, 1996Assignee: The Valspar CorporationInventors: Phillip C. Martino, Kenneth G. Davis
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Patent number: 5543464Abstract: Coating powder compositions are formulated with epoxy-functional acrylic resins, and as curatives 5 to 50 phr poly-carboxylic functional polyesters and 5 to 40 phr poly-carboxylic functional crystalline curatives.Type: GrantFiled: December 8, 1995Date of Patent: August 6, 1996Assignee: Morton International, Inc.Inventors: Owen H. Decker, Charles P. Tarnoski
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Patent number: 5510428Abstract: Compositions (I), (II) and (III) comprising compounds having vinyl groups as side chains and epoxidized compositions (XI), (XII) and (XIII) thereof, which can be prepared by the various reaction combinations of (a) with (b) or (b)+(c), and or (d), where(a) is at least one compound having at least one vinyl group and one epoxy group in the molecule; (b) is at least one of a polybasic compound, an anhydride thereof, a polymer having carboxylic groups at terminals and a polymer having carboxylic groups as side chains; (c) is at least one organic compound having at least one active hydrogen atom; and (d) is at east one of an unsaturated monocarboxylic compound or an unsaturated monocarboxylic ester having a hydroxyl group.Type: GrantFiled: November 21, 1994Date of Patent: April 23, 1996Assignee: Daicel Chemical Industries, Ltd.Inventors: Yoshiyuki Harano, Sozo Namai, Katsuyuki Maeda, Takaaki Murai
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Patent number: 5506331Abstract: A polyester polymer comprising repeating units (I), or repeating units (I) and (II), and having a reduced viscosity (.eta..sub.sp /c) of 0.2 to 10.0 dl/g, measured at 20.degree. C. as a 0.5 g/dl solution dissolved in methylene chloride is prepared by allowing a dihydric phenol (III), or dihydric phenols (III) and (IV), to react with a carbonate precursor or a dibasic acid. An electrophotographic photoreceptor which comprises an electroconductive substrate and a photosensitive layer disposed on the electroconductive substrate and containing the polyester polymer as a charge transporting material or a binder resin. ##STR1## wherein, W is --O-- or single bond, X is a divalent group which is derived from a dihydric phenol containing a hydrazine structure, each of R.sup.25 and R.sup.26 is a halogen atom, an alkyl group, a cycloalkyl group or an aryl group, each of m and n is an integer of 0 to 4, Y is single bond, --O--, --S--, --SO--, --SO.sub.2 --, --CR.sup.27 R.sup.28 --, a 1,1-cycloalkylene group or an .alpha.Type: GrantFiled: December 28, 1993Date of Patent: April 9, 1996Assignee: Idemitsu Kosan Co., Ltd.Inventors: Tomohiro Nagao, Shuji Sakamoto, Hironobu Morishita, Hideyuki Miyamoto
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Patent number: 5496910Abstract: A biodegradable hydroxy-functional polyester is prepared by contacting a hydroxy-functional aliphatic dicarboxylic acid or a mixture of dicarboxylic acids containing hydroxy-functional aliphatic diacids, with a diglycidyl ether or diglycidyl ester in the presence of an onium catalyst in an ether solvent under conditions suitable for forming the polyester.Type: GrantFiled: July 21, 1994Date of Patent: March 5, 1996Assignee: The Dow Chemical CompanyInventors: Michael N. Mang, Jerry E. White, Paul E. Swanson
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Patent number: 5496589Abstract: A curing composition and a method for impregnating wood using the curing composition, which comprises a reaction product represented by formula (1) obtained by reacting an alkylene oxide adduct of a hydrocarbon polyol and (meth)acrylic acid: ##STR1## wherein R.sup.10 represents a residual group of a hydrocarbon polyol having from 3 to 15 carbon atoms and (c1+d1) hydroxyl groups; R.sup.11 represents an alkylene group having from 2 to 4 carbon atoms; R.sup.12 represents an alkylene group having from 2 to 4 carbon atoms; R.sup.13 represents a hydrogen atom or a methyl group; a1 represents a number of from 0 to 10; b1 represents a number of from 0 to 10; c1 represents a number of not less than 1.5; and d1 represents a number of not less than 0.5; provided that (a1+b1) is not less than 1.Type: GrantFiled: March 22, 1994Date of Patent: March 5, 1996Assignee: Toagosei Chemical Industry Co., Ltd.Inventors: Ichiro Igarashi, Hiroyuki Ota, Yoshio Mizoguchi
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Patent number: 5466764Abstract: There are here disclosed an adhesive composition obtained by adding a fluorine-containing carboxylic acid epoxy adduct to a 2-cyanoacrylate, and a process for preparing the adhesive composition. This 2-cyanoacrylate-based adhesive composition is excellent in storage stability and particularly excellent in adhesive force and impact resistance and has a high hardening rate. In particular, the adhesive strength of the 2-cyanoacrylate-based adhesive composition can be remarkably increased without lowering the hardening rate, and so the 2-cyanoacrylate-based adhesive composition can exert a sufficient resistance to impact and the like at the time of the adhesion of metals, rubbers, plastics and lumbers and the reliability of adherends can be improved.Type: GrantFiled: September 16, 1994Date of Patent: November 14, 1995Assignee: Three Bond Co., Ltd.Inventor: Soichiro Hiraoka
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Patent number: 5457168Abstract: There is disclosed a solid composition of polyglycidyl compounds having a molecular weight of less than 1500, which composition consists of one or more than one solid polyglycidyl compound and altogether not less than 5% by weight of one or of a mixture of more than one polyglycidyl compound, which compound or mixture is normally in liquid form, said amount being based on the total amount of all polyglycidyl compounds in the composition, which composition contains the said solid polyglycidyl compounds or at least part of the said solid polyglycidyl compounds in form of one or a mixture of more than one solid mixed phase, which solid mixed phase or mixture of more than one solid mixed phase essentially comprises the total amount of the polyglycidyl compounds which are normally in liquid form as additional component or components.Type: GrantFiled: February 13, 1995Date of Patent: October 10, 1995Assignee: Ciba-Geigy CorporationInventors: Jacques-Alain Cotting, Philippe-Guilhaume Gottis
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Patent number: 5449528Abstract: A curing agent for a composition for the production of matt epoxide and hybrid powder coatings which is a mixture comprising:a) salts of phthalic, isophthalic and terephthalic acid and the following guanidines. ##STR1## wherein R, R.sup.1, R.sup.2, R.sup.3 and R.sup.4 may be identical or different radicals selected from the group consisting of H, (cyclo)alkyl and aromatic hydrocarbon radicals having 1-9 carbon atoms and where R.sup.1 with R.sup.2 and R.sup.3 with R.sup.4 each form a ring which contains an oxygen atom as heteroatom, and 0.5-2 mol of the guanidine A) react per mole of acid, andb) pyromellitic acid and/or trimellitic acid, 0.25-2 mol of b) employed per mole of a).Type: GrantFiled: December 19, 1994Date of Patent: September 12, 1995Assignee: Huels AktiengesellschaftInventors: Rainer Gras, Elmar Wolf
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Patent number: 5439977Abstract: An acid anhydride-containing one package epoxy resin composition consisting indispensably of (1) an epoxy resin having two or more epoxy groups in one molecule, (2) an acid anhydride, (3) at least one of (a) a liquid latent curing accelerator, (b) a latent curing accelerator soluble in an epoxy resin having two or more epoxy groups in one molecule and (c) a latent curing accelerator soluble in an acid anhydride, and (4) a dispersible latent curing accelerator, wherein the ratio of (1) to (2) is from 0.8 to 1.2, defined as the number of acid anhydride equivalents/the number of epoxy equivalents, and the amounts of (3) and (4) each are from 0.1 to 10 parts by weight to 100 parts by weight of the epoxy resin. The composition has excellent infiltrability, storage stability and reactivity.Type: GrantFiled: April 15, 1994Date of Patent: August 8, 1995Assignee: Ajinomoto Co., Inc.Inventors: Tadahiko Yokota, Hiroyuki Sakata, Kiyomiki Hirai, Koji Takeuchi
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Patent number: 5436103Abstract: Modified unsaturated linear polymers have at least a first residue, a second residue and an acid residue. The first, second and acid residues correspond to a first, second and acid monomers used to prepare the polymers. The first monomer may be a diacid, anhydride, diacid ester or mixture thereof. The second monomer may be a diol or glycol. The acid monomer may be an aromatic dicarboxylic acid, different than the first monomer. The first residue is present in a concentration not less than about 7.5 mole % and the acid residue is present in a concentration ranging between 2.5 mole % and 12.5 mole %, based on the total mole monomer ratio of the polymer. The polymers have a glass transition temperature ranging from about 54.degree. C. to about 64.degree. C.Type: GrantFiled: August 27, 1993Date of Patent: July 25, 1995Assignee: Xerox CorporationInventors: Robert D. Bayley, Carol A. Fox, Thomas R. Hoffend, James R. Paxson
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Patent number: 5412057Abstract: Anhydride compounds which contain at least one rodlike mesogenic moiety and at least two anhydride groups per molecule, wherein each of said aromatic anhydride groups is linked to the mesogen via an ester linkage are prepared. These anhydride compounds are useful in curing epoxy resins to provide the cured products with one or more improved properties.Type: GrantFiled: February 15, 1994Date of Patent: May 2, 1995Assignee: The Dow Chemical CompanyInventors: Robert E. Hefner, Jr., Jimmy D. Earls
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Patent number: 5412009Abstract: The invention provides a compound of general formula I ##STR1## in which X represents a direct bond or a ##STR2## group.Type: GrantFiled: December 7, 1992Date of Patent: May 2, 1995Assignee: FMC Corportion (UK) LimitedInventors: Michael J. Schneider, James Gainer
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Patent number: 5405932Abstract: Oil-soluble, phenolic resin-modified natural resinic acid esters, which are able to form self-gelling mineral oil solutions and in the form of gel varnishes can advantageously be used as binder resins in printing inks for offset printing and letterpress printing, and also processes for their preparation from natural resins, phenols, aldehydes, condensation catalyst, esterifying agents and modifiers by reaction of the components at temperatures in the range from 80.degree. to 300.degree. C., individual components preferably being initially introduced and the other components being metered in, the combined use of a magnesium compound as condensation catalyst and the continuous removal of the water of reaction during the condensation reaction by azeotropic distillation with co-use of an inert organic solvent as distillative entraining agent being necessary and decisive for the self-gelling property of the process product.Type: GrantFiled: January 21, 1994Date of Patent: April 11, 1995Assignee: Hoechst AGInventors: Albert Bender, Walter Hilker, Lothar Bothe
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Patent number: 5399654Abstract: A phosphorus-containing wholly aromatic polyester is produced by an interfacial polymerization method which includes the step of reacting a phosphorus-containing bisphenol compound and a bisphenol compound with dicarboxylic acid chlorides. An organic layer containing the dicarboxylic acid chlorides and phase transfer catalyst is added into an alkaline aqueous layer which contains a bisphenol compound.Type: GrantFiled: October 21, 1993Date of Patent: March 21, 1995Assignee: Korea Kumho Petrochemical Co., Ltd.Inventors: Young H. Ko, Seung D. Cho, Byung C. Jeon
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Patent number: 5395900Abstract: An acrylated epoxy resin based on bisphenol-S having a formula as follows ##STR1## wherein ph is phenylene or halophenylene; R.sub.1 is C.sub.2 -C.sub.4 alkylene;R.sub.2 is --CH.sub.2 CH(OH)CH.sub.2 --;R.sub.3 is acryloyl or methacryloyl;m is 0-4 integer, n is 0-4 integer and k is 0-5 integer.Type: GrantFiled: September 27, 1993Date of Patent: March 7, 1995Assignee: National Science CouncilInventors: Der-Jan Liaw, Wen-Chang Shen
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Patent number: 5391652Abstract: An epoxy ester resin which results from reacting (a) an epoxy resin, (b) a dimerized fatty acid and (c) a monocarboxylic acid. The epoxy ester resins are useful in coating compositions.Type: GrantFiled: April 23, 1993Date of Patent: February 21, 1995Assignee: The Dow Chemical CompanyInventors: David S. Wang, Pong S. Sheih, Loan A. Ho, Charles M. Vetters
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Patent number: 5362822Abstract: An adduct is prepared by reacting (A) a compound containing at least one epoxy group per molecule, with (B) a compound containing at least one epoxide reactive group per molecule selected from the group consisting of phenolic, thiol, secondary amine and carboxyl; wherein (i) when compound (A) is a polyepoxide, compound (B) contains a single epoxide reactive group per molecule; (ii) when compound (A) is a monoepoxide it is a monoglycidyl ether and compound (B) contains at least two epoxide reactive groups per molecule; and (iii) at least one of components (A) and (B) contains a rodlike mesogenic moiety. These adducts are useful in the preparation of polyurethanes.Type: GrantFiled: January 3, 1994Date of Patent: November 8, 1994Assignee: The Dow Chemical CompanyInventor: Robert E. Hefner, Jr.