With Reactant Which Is An Aldehyde, Aldehyde Derivative, Or Polymer Thereof, And Which Is Free Of An 1,2-epoxy Group (included Herein Are Alkylated Methylol Groups) Patents (Class 525/110)
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Patent number: 4467070Abstract: A novel organic solvent based, thermosetting coating composition comprises novel epoxy ester resin having number average molecular weight (M.sub.n) about 1000 to about 5000 and being the reaction product of diepoxide, for example bisphenol-A epichlorohydrin epoxy resin, with (i) diphenol, for example bisphenol-A, in chain extension reaction, (ii) dicarboxylic acid, for example the dimer acid reaction product of the dimerization of C-18 fatty acid, in chain extension reaction, and (iii) fatty acid, for example Soya fatty acid, in chain terminating esterification reaction, which chain extension reactions and esterification reaction occur at least in part substantially simultaneously. Preferably, catalyst is employed for said chain extension and esterification reactions. The coating composition further comprises polyfunctional aminoplast crosslinking agent, for example, hexamethoxymethylmelamine, and polycarboxy functional polymeric catalyst.Type: GrantFiled: September 30, 1982Date of Patent: August 21, 1984Assignee: Ford Motor CompanyInventors: Panagiotis I. Kordomenos, Kenneth R. Kurple
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Patent number: 4451506Abstract: Disclosed is a side seam-coated welded can comprising a welded can body having a seam on the side face and a resin coating layer covering at least one surface side of the seam, wherein said coating layer comprises a thermosetting resin and a thermoplastic resin having a softening point of 50.degree. to 300.degree. C. as determined according to the ring and ball method, at a volume ratio ranging (A) from 95/5 to 25/75 or (B) from 20/80 to 1/99, and one of said two resins is present in the coating in the form of a continuous phase and at least a part of the other resin is present in the coating in the form of fine dispersed particles.This can is excellent in corrosion resistance and processability.Type: GrantFiled: September 24, 1982Date of Patent: May 29, 1984Assignee: Toyo Seikan Kaisha LtdInventors: Seishichi Kobayashi, Tatsuo Mori, Tetsuo Miyazawa, Kazuo Taira, Makoto Horiguchi, Susumu Takahashi
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Patent number: 4436869Abstract: A process for the preparation of moldings, in particular resilient elements, which by virtue of a densified surface zone with substantially closed cells, have only a low water absorption, wherein a mixture comprising:(a) 100 parts by weight of an NCO-containing prepolymer, having an NCO content of from 3 to 6% by weight and based on organic diisocyanates and substantially linear polyester-polyols or polytetramethylene ether glycol,(b) from 0.5 to 1.6 parts by weight of water,(c) one or more catalysts, preferably a tertiary amine, in an amount of from 0.01 to 2.0 parts by weight and(d) assistants, with or without additives, is reacted in a closed mold, while undergoing densification, the surface temperature of the inner wall of the mold being from 50.degree. to 70.degree. C.Type: GrantFiled: March 30, 1982Date of Patent: March 13, 1984Assignee: Elastogran GmbHInventors: Otmar Zipp, Heinz Bollmann, Herbert Stutz, Wolfgang Scholz
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Patent number: 4430480Abstract: An improved two-part adhesive composition comprising as a first part monomer-in-polymer polymerizable solution and a second part, an activator enriched in its N-phenyl-3,5-diethyl-2-propyl-1,2-dihydropyridine content. The content is enriched to a concentration of at least about 70% of the second part.Type: GrantFiled: November 16, 1981Date of Patent: February 7, 1984Assignee: Loctite CorporationInventors: David P. Melody, Seamus M. Grant, Francis R. Martin
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Patent number: 4427802Abstract: A curable composition, and composites comprising (A) an epoxy resin and (B) a heterocyclic compound prepared by reacting at least one aromatic or aliphatic polyamine compound having at least two amine groups, which are separated by no more than one carbon atom, with at least one carbonyl-containing compound selected from the group consisting of aldehydes and ketones.Type: GrantFiled: July 27, 1981Date of Patent: January 24, 1984Assignee: Hexcel CorporationInventors: Richard J. Moulton, John D. Neuner
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Patent number: 4425450Abstract: Coating compositions comprising hydroxy functional film formers, crosslinking agent therefor and a novel flow control additive. Flow control additive comprises stable crosslinked dispersion formed by addition polymerization of selected monomers in the presence of (i) organic liquid which is a solvent for the monomers, but a non-solvent for the polymer and (ii) polymeric dispersion stabilizer having solvated and non-solvated segments, wherein the dispersion is stabilized further by inclusion therein of a butylated melamine formaldehyde resin.Type: GrantFiled: August 14, 1981Date of Patent: January 10, 1984Assignee: Ford Motor CompanyInventor: Stanley K. Horvath
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Patent number: 4419495Abstract: The gloss of epoxy resin powder coatings is reduced by employing as the curing agent therefor or as a portion of the curing agent therefor, a polymer of two or more polymerizable ethylenically unsaturated monomers, at least one of which contains a group which is reactive with a vicinal epoxy group.Type: GrantFiled: August 23, 1982Date of Patent: December 6, 1983Assignee: The Dow Chemical CompanyInventor: Rhetta Q. Davis
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Patent number: 4418182Abstract: A novel tetrahydroxy oligomer crosslinkable with amine-aldehyde resins to form a coating composition adapted for use as an automotive topcoat and which upon curing forms a hard, glossy, coating with outstanding durability and excellent resistance to solvents and water. The coating composition comprises:(A) a tetrahydroxy oligomer having a number average (Mn) molecular weight of between about 600-2000 and being the reaction product of:(i) an ester containing pendant hydroxyl and carboxyl functionality and being made by a reaction wherein the reactants consist essentially of:(a) a C.sub.3 -C.sub.Type: GrantFiled: December 28, 1981Date of Patent: November 29, 1983Assignee: Ford Motor CompanyInventor: Mohinder S. Chattha
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Patent number: 4379886Abstract: A thermosetting coating composition having a binder of a film forming polymer having reactive hydroxyl groups, epoxy groups or methylol groups and a melamine, benzoguanamine or urea crosslinking agent and about 0.1-10% by weight of reactive catalyst which is a solid at 30.degree. C. in which the catalyst has one of the following structures: ##STR1## or mixtures of the above; where R is an alkyl group or a hydroxy alkyl group having 1-18 carbon atoms; the catalyst is prepared by reacting in a 1:1 molar ratio trimellitic anhydride and an aliphatic monohydric alcohol or an aliphatic diol.Type: GrantFiled: July 2, 1981Date of Patent: April 12, 1983Assignee: E. I. Du Pont de Nemours and CompanyInventors: Joseph E. McLaughlin, George A. Strickland
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Patent number: 4379872Abstract: Amphoteric amino sulfonate derivatives of epoxy resins having at least one terminal group of the formula: ##STR1## wherein R.sub.1 and R.sub.2 are hydrogen or methyl, R.sub.3 is hydrogen or C.sub.1 -C.sub.20 alkyl or substituted alkyl, and R.sub.4 is C.sub.1 -C.sub.6 alkylene or substituted alkylene, which are reaction products of an epoxy resin having a plurality of terminal groups of the formula: ##STR2## wherein R.sub.1 and R.sub.2 are as defined, with an amino sulfonate of the formula:R.sub.3 --NH--R.sub.4 --SO.sub.3 Mwherein R.sub.3 and R.sub.4 are as defined, and M is a cation.Type: GrantFiled: August 17, 1981Date of Patent: April 12, 1983Assignee: Nippon Paint Co., Ltd.Inventors: Shin-Ichi Ishikura, Kazunori Kanda, Ryuzo Mizuguchi
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Patent number: 4363896Abstract: Thermosetting high solids coating compositions which: (i) cure, at least in part, by reaction between an amine-aldehyde compound and hydroxyl functionality on a film-forming component, which hydroxyl functionality is either generated in situ during the cure of the composition or is both generated in situ during cure and is present on the film-forming component prior to curing; (ii) are adapted for low temperature bake applications; and (iii) contain greater than about 55% by weight of nonvolatile solids.Type: GrantFiled: July 28, 1981Date of Patent: December 14, 1982Assignee: Ford Motor CompanyInventor: Mohinder S. Chattha
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Patent number: 4355058Abstract: Storage stable epoxy resin powder coating compositions are disclosed, which contain a solid epoxy resin and, as hardening agent, a blocked polyisocyanate compound or isocyanate terminated polymer, wherein the blocking agent is an imidazoline compound.Type: GrantFiled: August 14, 1978Date of Patent: October 19, 1982Assignee: Chemische Werke Huels AktiengesellschaftInventors: Rainer Gras, Johann Obendorf, Elmar Wolf
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Patent number: 4350790Abstract: Thermosetting high solids coating compositions which: (i) cure, at least in part, by reaction between an amine-aldehyde compound and hydroxyl functionality on a film-forming component, which hydroxyl functionality is either generated in situ during the cure of the composition or is both generated in situ during cure and is present on the film-forming component prior to curing; (ii) are adapted for low temperature bake applications; and (iii) contain greater than about 55% by weight of nonvolatile solids. The claimed high solids coating compositions, exclusive of pigments, solvents and other nonreactive components, consist essentially of:(A) a film-forming component selected from the group consisting of an epoxy functional copolymer and polyepoxide resin;(B) a latent reactive catalyst comprising the reaction product of (i) a copolymer bearing pendent epoxy functionality, and (ii) a particular sulfonic acid;(C) an amine-aldehyde crosslinking agent; and(D) an optional hydroxy functional additive.Type: GrantFiled: September 8, 1981Date of Patent: September 21, 1982Assignee: Ford Motor CompanyInventor: Mohinder S. Chattha
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Patent number: 4341682Abstract: Non-gelled compositions containing hydroxy ester copolymer having carboxyl groups and substantially free of oxirane groups are disclosed which are the esterification reaction product of(a) acidic addition copolymer; and(b) a polyepoxide which has been partially defunctionalized by reaction with carboxyl containing polybutadiene polymer. The resulting composition is neutralized with amine, is self-emulsifiable in water and is useful for coatings.Type: GrantFiled: December 23, 1980Date of Patent: July 27, 1982Assignee: Mobil Oil CorporationInventor: Michael A. Tobias
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Patent number: 4336346Abstract: Surface-coating binders based on a copolymer which contains carboxyl groups, blocked isocyanate groups, hydroxyl groups and ether groups, and which, due to partial or complete salification with ammonia or with an organic base, is water-soluble or water-dispersible.This copolymer contains, as copolymerized units, one or more .alpha.,.beta.-olefinically unsaturated carboxylic acids of 3 to 5 carbon atoms or one or more half-esters of an .alpha.,.beta.-olefinically unsaturated dicarboxylic acid of 3 to 5 carbon atoms, an N-(1-alkenyl) isocyanate blocked with a CH--, OH-- or NH-acidic blocking agent, an adduct of an epoxy resin, based on bisphenol A and epichlorohydrin and having a molecular weight of from 380 to 3,500, with an olefinically unsaturated alcohol of 3 to 20 carbon atoms, and one or more other copolymerizable olefinically unsaturated compounds, and has a mean molecular weight of from 1,000 to 20,000 and an acid number of from 35 to 150 mg of KOH/g.Type: GrantFiled: April 10, 1981Date of Patent: June 22, 1982Assignee: BASF AktiengesellschaftInventors: Juergen Gimpel, Karl-Heinz Feuerherd, Hans-Uwe Schenck
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Patent number: 4332713Abstract: A liquid or pasty thermosetting adhesive which can be pre-gelled, which is suitable for the bonding of moulded parts or for the sealing of folded seams, and which contains (a) a liquid epoxide resin having on average more than one epoxide group in the molecule, and (b) a latent epoxide curing agent insoluble in the epoxide resin, the adhesive being characterized in that it also contains (c) in an amount of 5 to 50 percent by weight relative to the epoxide resin, at least one halogen-free thermoplast in powder form, which is insoluble in the epoxide resin at room temperature, and which has a softening point of between 60.degree. and 160.degree. C., such as a polyethylene, a polypropylene or an ethylene/acrylic acid/acrylate terpolymer.Type: GrantFiled: October 29, 1980Date of Patent: June 1, 1982Assignee: Ciba-Geigy CorporationInventor: Hans Lehmann
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Patent number: 4324715Abstract: A coating composition comprising a dispersion of an epoxy resin, a nitrogen resin crosslinker such as a melamine formaldehyde, a particulate fluorocarbon such as PTFE, and citric acid can be applied to substrates such as polysulfones and cured at low temperatures on the order of 107.degree. C. The resulting coating is especially useful as a barrier to seal the surface of the substrate and to improve abrasion resistance.Type: GrantFiled: October 29, 1980Date of Patent: April 13, 1982Assignee: E. I. DuPont de Nemours and CompanyInventor: Dennis P. Emerick
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Patent number: 4323660Abstract: Thermosetting compositions comprising: (A) a sulfonic acid ester comprising the reaction product of an epoxy functional polymer bearing hydroxyl functionality, and a sulfonic acid having the formula ##STR1## wherein R is selected from linear or branched alkyl groups and aryl groups; and (B) an amine aldehyde crosslinking agent.During cure of the composition, component (A) breaks down to form not only a reactive sulfonic acid catalyst, but also the hydroxy functional film forming material which crosslinks with the amine aldehyde crosslinking agent.Type: GrantFiled: January 4, 1980Date of Patent: April 6, 1982Assignee: Ford Motor CompanyInventor: Mohinder S. Chattha
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Patent number: 4322508Abstract: A high solids, thermosetting coating composition which, exclusive of pigments, solvents and other nonreactive components consists essentially of:(A) A hydroxy functional component consisting of:(1) between about 1 and about 90 weight percent of an oligoester (i) having a number average molecular weight (M.sub.n) of between about 150 and about 3000 (ii) bearing at least about 2 hydroxyl groups and (iii) being formed by an esterification reaction between a carboxylic acid and an epoxide; and(2) between about 99 and about 10 weight percent of a hydroxy functional copolymer having a number average molecular weight (M.sub.Type: GrantFiled: June 9, 1980Date of Patent: March 30, 1982Assignee: Ford Motor CompanyInventors: Stephen C. Peng, David M. Thomson
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Patent number: 4307208Abstract: Thermosetting compositions comprising a film forming component bearing or capable of generating hydroxyl functionality, amine-aldehyde crosslinking agent, and a latent reactive catalyst comprising the reaction product of (i) a copolymer bearing pendent epoxy functionality, and (ii) a sulfonic acid having the formula ##STR1## wherein R is selected from linear or branched alkyl groups and aryl groups.Preferred compositions within the scope of the invention include high solids, thermosetting coating compositions suitable for automotive applications.Type: GrantFiled: January 4, 1980Date of Patent: December 22, 1981Assignee: Ford Motor CompanyInventor: Mohinder S. Chattha
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Patent number: 4302373Abstract: Water-borne reaction products of (a) carboxylfunctional polymers; (b) modified polyepoxides; and (c) tertiary amines are useful as film-forming components of coating compositions which can be spray-, flow-, dip-, roller-, or electro-coated. The coating compositions are useful as such or can be crosslinked with crosslinking agents such as a nitrogen resin and, when coated on metal and paper substrates, they provide coatings of improved properties, including a high degree of flexibility during machining and stamping of the coated articles, corrosion resistance, gloss, hydrolytic stability, and nonadulterating of foods and beverages in contact therewith.Type: GrantFiled: August 5, 1980Date of Patent: November 24, 1981Assignee: E. I. Du Pont de Nemours and CompanyInventor: William H. Steinmetz
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Patent number: 4299747Abstract: Coating compositions which may be applied by conventional techniques as well as by electrodeposition are provided by reacting a polyglycidyl ether of a polyphenol with an amino acid containing at least one amine group and one carboxyl group, wherein the amine group of the acid is preferentially reactive with the epoxy groups of the polyglycidyl ether. The resultant product can then be solubilized by neutralizing at least a portion of the acid functionality thereof with an amine or other base. Especially useful amino acids are the aminobenzoic acids.Type: GrantFiled: March 8, 1977Date of Patent: November 10, 1981Assignee: PPG Industries, Inc.Inventor: William J. Birkmeyer
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Patent number: 4293457Abstract: A primer composition comprises an oil-free saturated polyester resin, an aminoplast curing agent for the polyester, and a thermoplastic acrylic polymer. The primer is used as a bond coat to adhere an acrylic polymer dispersion topcoat to a metal base.Type: GrantFiled: November 14, 1979Date of Patent: October 6, 1981Assignee: PPG Industries, Inc.Inventor: Martin J. Simon
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Patent number: 4291137Abstract: A one-pack high solid coating composition consisting essentially of (I) 100 parts by weight of an acrylic resin which is a copolymer having a glass transition temperature of -21.degree. to -50.degree. C. and a hydroxyl number of 40 to 280 and being prepared from (a) one or more members selected from hydroxyalkyl acrylates and methacrylates of the general formula ##STR1## wherein R is a hydrogen atom or a methyl group and R.sub.1 is a divalent alkyl group having 2 to 5 carbon atoms, and (b) one or more members selected from alkyl acrylates and methacrylates of the general formula ##STR2## wherein R is as defined above and R.sub.2 is a monovalent alkyl group having 1 to 12 carbon atoms, and glycidyl acrylates and methacrylates of the general formula ##STR3## wherein R is as defined above and R.sub.3 is a divalent alkyl group having 1 to 5 carbon atoms, (II) 20 to 160 parts by weight of an amino-formaldehyde resin etherified with a monohydric alcohol having 1 to 4 carbon atoms, and (III) 0.Type: GrantFiled: August 31, 1979Date of Patent: September 22, 1981Assignee: Kansai Paint Co., Ltd.Inventors: Yasushi Nakate, Hiroshi Iwai, Kiyoshi Nanishi
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Patent number: 4281075Abstract: Thermosetting compositions comprising a film forming component bearing or capable of generating hydroxyl functionality, amine-aldehyde crosslinking agent, and a latent reactive catalyst having the formula: ##STR1## wherein R is selected from alkyl or aryl groups and X is selected from 2-hydroxycycloalkyl and aryl substituted 2-hydroxycycloalkyl groups.Preferred compositions within the scope of the invention include high solids, thermosetting coating compositions suitable for automotive applications.Type: GrantFiled: January 4, 1980Date of Patent: July 28, 1981Assignee: Ford Motor CompanyInventor: Mohinder S. Chattha
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Patent number: 4238573Abstract: The curing temperature of an otherwise substantially conventional methacrylate coating composition is lowered and the weather resistance of the cured composition is improved by incorporating therein a phosphated and amine-neutralized epoxy resin.Type: GrantFiled: February 12, 1979Date of Patent: December 9, 1980Assignee: E. I. Du Pont de Nemours and CompanyInventor: Louis W. Hamilton
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Patent number: 4237241Abstract: An improved thermosetting coating composition of the type comprising a film forming component and an amine aldehyde compound, wherein the composition cures by reaction between the amine aldehyde compound and hydroxy functionality present on the film forming material. The improvement comprises including in the composition a catalyst comprising at least one hydroxy functional organophosphate ester selected from certain mono- and diesters of phosphoric acid.Type: GrantFiled: September 22, 1978Date of Patent: December 2, 1980Assignee: Ford Motor CompanyInventor: Mohinder S. Chattha
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Patent number: 4196270Abstract: A fast curing, high solids coating composition that is adapted for use as an automotive topcoat and which upon curing forms a hard, glossy, durable coating exhibiting excellent resistance to solvents and water. The coating composition contains greater than about 60 percent by weight of nonvolatile solids and, exclusive of pigments, solvents and other nonreactive components, consists essentially of:(A) a polyepoxide resin having a number average molecular weight (M.sub.n) of between about 140 and about 3,000;(B) a reactive catalyst comprising at least one hydroxy functional organophosphate ester selected from certain mono- and diesters of phosphoric acid;(C) an amino resin crosslinking agent; and(D) optionally, a hydroxy functional additive.The hydroxy functional organophosphate ester is included in the composition in an amount sufficient to provide between about 0.67 and about 1.Type: GrantFiled: September 22, 1978Date of Patent: April 1, 1980Assignee: Ford Motor CompanyInventor: Mohinder S. Chattha
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Patent number: 4192932Abstract: Crosslinking compositions comprising (a) optionally at least partially neutralized reaction product of di- or poly epoxy compound and hydroxy amine and (b) amino resin crosslinker that are formulated into primers providing alkaline resistant coatings even in absence of chromate inhibiting pigments are improved by incorporation of reactive hydroxy phosphate catalyst that lowers cure temperature without increase in moisture sensitivity of cured coating. One reactive catalyst is a reaction product of di- or triol and P.sub.2 O.sub.5.Type: GrantFiled: August 31, 1978Date of Patent: March 11, 1980Assignee: Ford Motor CompanyInventors: Ray A. Dickie, Joseph W. Holubka, Mohinder S. Chattha
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Patent number: 4192929Abstract: Electrodepositable resins that do not require chromate corrosion inhibiting pigments and comprise (A) the at least partially neutralized reaction product of (1) an epoxy reactant having about two or more epoxy groups that are not linked by carboxy-ester moieties and (2) an amine reactant selected from mono and diamines containing primary or secondary amino groups and also being at least about 50 mole percent hydroxy amine, (B) water soluble or dispersible amino resin crosslinking agent are improved by incorporation of (C) a co-reactive flow control agent that comprises, for example, a polyepoxy copolymer having a molecular weight desirably between 1000-20,000. The co-reactive flow control agent, used at low levels, allows formation of smooth, non-tacky films exhibiting desirable corrosion resistant properties.Type: GrantFiled: August 31, 1978Date of Patent: March 11, 1980Assignee: Ford Motor CompanyInventor: Robert C. Wingfield, Jr.
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Patent number: 4160757Abstract: An adhesive composition which shows improved stickiness and adhesive property at room temperature and exhibits an excellent adhering ability in a short time is prepared by compounding(a) an acrylonitrile-containing copolymer having carbon-to-carbon double bond(b) a phenol-polysulfide resin(c) a metal oxide, and(d) a polyfunctional electrophilic reactive compound containing at least two electrophilic reactive groups.Type: GrantFiled: February 28, 1977Date of Patent: July 10, 1979Assignee: Bridgestone Tire Co., Ltd.Inventors: Toshio Honda, Yukio Fukuura, Shoji Tanaka, Itsuo Tanuma, Yoshikatsu Suzuki, Hikaru Ishikawa