Phenolic Reactant Contains Ethylenic Unsaturation Or Contains A 1,2-epoxy Group Fused To A Carbocyclic Ring Patents (Class 528/101)
  • Patent number: 5270405
    Abstract: Advanced epoxy resins containing mesogenic moieties are prepared from epoxy resins which contain such moieties.
    Type: Grant
    Filed: July 27, 1992
    Date of Patent: December 14, 1993
    Assignee: The Dow Chemical Company
    Inventors: Jimmy D. Earls, Robert E. Hefner, Jr., Paul M. Puckett
  • Patent number: 5268434
    Abstract: An epoxy resin composition useful as a molded article is curable with a combination of curing agents including diamino-alpha-alkylstilbenes and other curing agents wherein the epoxy resin and/or the other curing agents can contain rodlike mesogenic moieties.
    Type: Grant
    Filed: January 5, 1993
    Date of Patent: December 7, 1993
    Assignee: The Dow Chemical Company
    Inventors: Robert E. Hefner, Jr., Jimmy D. Earls
  • Patent number: 5266365
    Abstract: The present invention is directed to an epoxy-containing polymeric material having nonlinear optical properties, particularly a glycidyl amine polymer, and a process for making the nonlinear optical (NLO) epoxy-containing polymeric material including poling the polymeric material under high voltage at elevated temperature for a period of time to bring about orientation of the nonlinear optical functionalities in the polymer. The polymers have enhanced thermal stability and good NLO properties.
    Type: Grant
    Filed: February 28, 1992
    Date of Patent: November 30, 1993
    Assignee: The Dow Chemical Company
    Inventors: John J. Kester, H. Craig Silvis
  • Patent number: 5266405
    Abstract: This invention relates to thermosetting compositions for the production of epoxide networks of very high impact strength, to a process for their preparation and to their use as polymer materials, coating compounds, adhesives and materials for electrical insulation.
    Type: Grant
    Filed: July 22, 1991
    Date of Patent: November 30, 1993
    Assignee: Bayer Aktiengesellschaft
    Inventors: Stephan Kirchmeyer, Hanns P. Muller, Alexander Karbach, Joachim Franke
  • Patent number: 5266660
    Abstract: Compositions comprising epoxy resins containing one or more rodlike mesogenic moieties per molecule are cured with curing agents which will normally cure epoxy resins. These curable compositions can be oriented by the application of an electric field, magnetic field drawing and/or shear flow prior to and/or during curing. The resultant cured products exhibit an improvement in one or more physical or mechanical properties as compared to a like epoxy resin system which does not contain any rodlike mesogenic moieties.
    Type: Grant
    Filed: July 17, 1992
    Date of Patent: November 30, 1993
    Assignee: The Dow Chemical Co.
    Inventors: Robert E. Hefner, Jr., Jimmy D. Earls, Paul M. Puckett
  • Patent number: 5266661
    Abstract: Curable compositions are disclosed which contain (I) an advanced resin composition prepared by reacting epoxy resins with active hydrogen-containing compounds which contain mesogenic moieties and (II) a suitable curing agent.
    Type: Grant
    Filed: September 15, 1992
    Date of Patent: November 30, 1993
    Assignee: The Dow Chemical Company
    Inventors: Jimmy D. Earls, Paul M. Puckett, Robert E. Hefner, Jr.
  • Patent number: 5242996
    Abstract: A modified epoxy resin or compound of the formula: ##STR1## wherein A is the backbone reside of a glycidyl ether epoxy resin with removal of the glycidyloxy groups; R.sup.1 and R.sup.2 are independently a hydrogen atom or C.sub.1 -C.sub.12 alkyl; R.sup.3 is a glycidyl group; and n is an integer of greater than 1. A method for producing the modified epoxy resin is also disclosed.
    Type: Grant
    Filed: May 22, 1991
    Date of Patent: September 7, 1993
    Assignee: Nippon Paint Co., Ltd.
    Inventors: Mitsuo Yamada, Kei Aoki, Ryuzo Mizuguchi
  • Patent number: 5235006
    Abstract: Novel mesogens, epoxy resins and the synthesis thereof as well as coating binders for coating compositions based upon the mesogens and epoxy resins are described.
    Type: Grant
    Filed: September 18, 1990
    Date of Patent: August 10, 1993
    Assignee: North Dakota State University
    Inventors: Frank N. Jones, Steven L. Kangas, Der-Shyang Chen, Adel F. Dimian, Daozhang Wang
  • Patent number: 5227452
    Abstract: Compositions comprising epoxy resins containing one or more rodlike mesogenic moieties per molecule are cured with polyamines containing one or more rodlike mesogenic moieties per molecule. These curable compositions can be oriented by the application of an electric field or magnetic field or drawing and/or shear flow prior to and/or during curing. The resultant cured products exhibit an improvement in one or more physical and/or mechanical and/or thermal properties as compared to a like epoxy resin system which does not contain any rodlike mesogenic moieties.
    Type: Grant
    Filed: June 29, 1992
    Date of Patent: July 13, 1993
    Assignee: The Dow Chemical Company
    Inventors: Jimmy D. Earls, Robert E. Hefner, Jr., Paul M. Puckett
  • Patent number: 5218074
    Abstract: The invention provides epoxy resins having the following structure: ##STR1## The cross-linked epoxy resins have non-linear optical properties. The group "Z" constitutes a nonlinear optical chromophone having stilbene, azo, azomethine or propargyl moieties as linking units.
    Type: Grant
    Filed: September 17, 1991
    Date of Patent: June 8, 1993
    Assignees: Siemens Aktiengesellschaft, Siemens Aktiengesellschaft
    Inventors: Jens Nordmann, Heinz Hacker
  • Patent number: 5218062
    Abstract: Compositions comprising epoxy resins containing one or more rodlike mesogenic moieties per molecule are cured with polyamines containing one or more rodlike mesogenic moieties per molecule. These curable compositions can be oriented by the application of an electric field or magnetic field or drawing and/or shear flow prior to and/or during curing. The resultant cured products exhibit an improvement in one or more physical and/or mechanical and/or thermal properties as compared to a like epoxy resin system which does not contain any rodlike mesogenic moieties.
    Type: Grant
    Filed: June 29, 1992
    Date of Patent: June 8, 1993
    Assignee: The Dow Chemical Company
    Inventors: Jimmy D. Earls, Robert E. Hefner, Jr., Paul M. Puckett
  • Patent number: 5210115
    Abstract: A modified epoxy resin of the general formula (I) is prepared by dissolving an epoxy resin in a solvent, adding the mixture to allyl magnesium halide at -70.degree. C. under a nitrogen atmosphere, and removing the solvent and salts from the resultant product. The modified epoxy resin is useful for epoxy maleimide resin compositions as a heat resistance enhancer. An epoxy resin composition for sealing semiconductor elements comprising the modified epoxy resin as a heat resistance enhancer is an amount of from 0.1 to 30% by weight, based on the total weight of the composition, is also provided. ##STR1## wherein, R represents H or C.sub.1 to C.sub.10 -alkyl group and m represents an integer of 0 to 100 and n represents an integer of 1 to 100.
    Type: Grant
    Filed: December 6, 1991
    Date of Patent: May 11, 1993
    Assignee: Cheil Industries, Inc.
    Inventors: Whan G. Kim, Tai Y. Nam
  • Patent number: 5179176
    Abstract: An epoxy resin having a propenyl group conjugated with an aromatic ring is heat resistant and is easily molded and cured into products having high strength and Tg. It is thus useful as a resin component or modifier.
    Type: Grant
    Filed: February 1, 1991
    Date of Patent: January 12, 1993
    Assignee: Shin-Etsu Chemical Company, Ltd.
    Inventors: Toshio Shiobara, Hisashi Shimizu, Takayuki Aoki
  • Patent number: 5164464
    Abstract: Thermosettable vinyl ester resin compositions are prepared from polyepoxide compounds, optionally, monoepoxide compounds, at least one of which contains a mesogenic or rigid rodlike moiety and a monounsaturated monocarboxylic acid. These vinyl ester resins can be mixed with polymerizable ethylenically unsaturated monomers which can, if desired, contain a mesogenic or rigid rodlike moiety.
    Type: Grant
    Filed: June 7, 1991
    Date of Patent: November 17, 1992
    Assignee: The Dow Chemical Company
    Inventors: Robert E. Hefner, Jr., Jimmy D. Earls, Paul M. Puckett
  • Patent number: 5079330
    Abstract: A polyoxymethylene multi-copolymer obtainable by copolymerizing(a) trioxane,(b) at least one cyclic ether or formal compound chosen from the group of ethylene oxide, 1,3-dioxolane, 1,3-dioxepane, 1,3,5-trioxepane and 1,3,6-trioxocane, and(c) at least one compound chosen from the group of glycidyl phenyl ether, styrene oxide and glycidyl naphthyl ether,and characterized in that the number average molecular weight of said polyoxymethylene multi-copolymer is from 10,000 to 100,000, that the melting point (Tm) and crystallization temperature (Tc) there of are in a relationship ofTm-Tc<15 (.degree.C.)and that the size of the spherulites is 10 .mu.m or less, or a resin composition comprised of this polyoxymethylene multi-copolymer and a polyoxymethylene resin, is distinguished in crystallinity, mechanical strength and surface appearance and is particularly suited for faster cycle molding.
    Type: Grant
    Filed: August 6, 1990
    Date of Patent: January 7, 1992
    Assignee: Toray Industries, Inc.
    Inventors: Yoshiki Makabe, Shigeru Okita, Yoshiyuki Yamamoto
  • Patent number: 5023310
    Abstract: Chain extended tougheners derived from the reaction of a propenylphenol, a di- or polyphenol, and an epoxy resin may be used to increase the toughness of bismaleimide resin systems.
    Type: Grant
    Filed: September 14, 1989
    Date of Patent: June 11, 1991
    Assignee: BASF Aktiengesellschaft
    Inventor: Jack D. Boyd
  • Patent number: 4916203
    Abstract: A curable resin composition comprises an epoxy compound and a propargyl aromatic ether.
    Type: Grant
    Filed: November 14, 1988
    Date of Patent: April 10, 1990
    Assignee: Shell Oil Company
    Inventors: Anthony M. Pigneri, James Vick, III, deceased
  • Patent number: 4908423
    Abstract: The invention relates to compounds of the formula I or II ##STR1## in which A is a radical ##STR2## R.sup.1 is hydrogen or methyl, R.sup.2 is the radical of an aliphatic, cycloaliphatic, aromatic or araliphatic diol after both of the hydroxyl groups have been removed, R.sup.3, R.sup.4, R.sup.5 and R.sup.6 independently of one another are hydrogen, C.sub.1 -C.sub.6 alkyl, chlorine or bromine, R.sup.7 is a radical of the formula III, IV, V or VI ##STR3## R.sup.8, R.sup.10, R.sup.12 and R.sup.14 are hydrogen, C.sub.1 -C.sub.6 alkyl or phenyl, R.sup.9, R.sup.11, R.sup.13 and R.sup.15 are hydrogen or C.sub.1 -C.sub.6 alkyl and the average value of n (number average) is a number from 1 to 20, it being possible for the radicals R.sup.1 to R.sup.15, within a given molecule, to assume different meanings within the scope of the definitions given.These compounds or also the epoxidized intermediates of the formula X ##STR4## in which R.sup.1 to R.sup.3 are as defined above and R.sup.
    Type: Grant
    Filed: November 14, 1988
    Date of Patent: March 13, 1990
    Assignee: Ciba-Geigy Corporation
    Inventors: Martin Roth, Charles E. Monnier
  • Patent number: 4883844
    Abstract: Epoxy resins of substituted hydroxystyrylaza compounds are disclosed. These thermosettable epoxy resins are cured to give a combination of high mechanical strength and glass transition temperature.
    Type: Grant
    Filed: December 6, 1988
    Date of Patent: November 28, 1989
    Assignee: The Dow Chemical Company
    Inventors: Robert E. Hefner, Jr., John W. Robinson, Jimmy D. Earls
  • Patent number: 4845172
    Abstract: Co-advanced epoxy resins prepared by the reaction of polyethers of polyhydric phenols, diglycidyl ethers of di-secondary alcohols and dihydric phenols, said co-advanced resins being heat curable with suitable curing agents to afford cured coating compositions exhibiting a variety of excellent physical properties and performance characteristics.The diglycidyl ethers have the following formula: ##STR1## as defined in the specification.
    Type: Grant
    Filed: April 26, 1988
    Date of Patent: July 4, 1989
    Assignee: Ciba-Geigy Corporation
    Inventors: Vincent Brytus, Kenneth L. Payne
  • Patent number: 4840979
    Abstract: This invention provides a process for the preparation of cationic coating compositions, which comprises blending:(1) 5-35% w of a crosslinking compound, and(2) 65-95% w of a carboxylated amide group-containing amino binder being the reaction product of an amino group-containing resin binder and not more than about 0.1 mole of a cyclic anhydride per amino group equivalent of said amino group containing resin binder, which amino group-containing binder comprises the reaction product of(a) ammonia, and(b) a blend of(b.sub.1) a polyglycidyl ether having n epoxy groups per molecule, wherein 1<n<1.9, said polyglycidyl ether being the reaction product of a multifunctional polyglycidyl ether having x epoxy groups per molecule, wherein x>2, and (x-n) mol of a monofunctional phenol per mol of the multifunctional polyglycidyl ether, and(b.sub.
    Type: Grant
    Filed: June 10, 1988
    Date of Patent: June 20, 1989
    Assignee: Shell Oil Company
    Inventors: Roeland Van Iperen, Johannes M. Van Der Mark, Petrus G. Kooijmans
  • Patent number: 4789711
    Abstract: The invention relates to compounds of the formula I ##STR1## in which A is a group ##STR2## R.sup.1 is hydrogen or methyl R.sup.2 is C.sub.1 -C.sub.6 -alkyl, halogen or phenyl,X is a direct C--C bond, --CH.sub.2 -- or --SO.sub.2 --,m is 0, 1, 2 or 3, n is 0, 1 or 2 andp is 0 or, in the case of X=--CH.sub.2 --, can also be an integer from 1 to 6, with the proviso that the groups --A and --O--A are in the ortho-position relative to one another.The compounds can preferably be used as matrix resins for composite materials.The invention also relates to the allyl glycidyl ether intermediates, from which the compounds of the formula I are as a rule prepared by epoxidation with peracids.
    Type: Grant
    Filed: November 23, 1987
    Date of Patent: December 6, 1988
    Assignee: Ciba-Geigy Corporation
    Inventors: Charles E. Monnier, Sameer H. Eldin, Peter Flury
  • Patent number: 4774282
    Abstract: Novel curable resin compositions are disclosed containing an aromatic cyanate ester and an allyl ether of a bisphenol as a modifier. These compositions provide improved prepregs and composites. Additional modifiers including epoxy resins and bismaleimides may be included.
    Type: Grant
    Filed: November 20, 1986
    Date of Patent: September 27, 1988
    Assignee: Amoco Corporation
    Inventor: Shahid P. Qureshi
  • Patent number: 4771112
    Abstract: Oligomeric and prepolymeric organic compounds with aldehyde, epoxide, isocyanate, or halotriazine groups and polymerizable groups. Compounds of this type and mixtures thereof have outstanding adhesion properties, especially in relation to biological substrates, can be copolymerized with composites based on unsaturated monomers, and are especially appropriate in dentistry and medicine as adhesion promoters, adhesive fillers, or adhesive cement.
    Type: Grant
    Filed: October 7, 1987
    Date of Patent: September 13, 1988
    Assignee: Ernst Muhlbauer KG
    Inventor: Jurgen Engelbrecht
  • Patent number: 4754003
    Abstract: Novel epoxidised phenol ethers of formula I ##STR1## are described wherein R.sup.1 denotes C.sub.1 -C.sub.20 alkyl, C.sub.5 -C.sub.9 cycloalkyl or C.sub.7 -C.sub.14 aralkyl, R.sup.2 has one of the meanings of R.sup.1 or is, in addition hydrogen or a radical or formula II ##STR2## R.sup.3 denotes C.sub.1 -C.sub.6 alkyl or halogen, R.sup.4 and R.sup.5 denotes hydrogen or C.sub.1 -C.sub.6 alkyl, R.sup.6 denotes hydrogen or methyl, m is 0, 1 or 2 and n is an integer from 0 to 30, with the proviso that at least two radicals, R.sup.2, must be epoxide groups of formula II. The compounds are especially suitable for encasing electronic components.
    Type: Grant
    Filed: April 15, 1987
    Date of Patent: June 28, 1988
    Assignee: Ciba-Geigy Corporation
    Inventors: Charles E. Monnier, Martin Roth
  • Patent number: 4737553
    Abstract: Advanced epoxy resins prepared by the reaction of diglycidyl ethers of di-secondary alcohols and dihydric phenols, said advanced resins being heat curable with suitable curing agents to afford cured coating compositions exhibiting a variety of excellent physical properties and performance characteristics.
    Type: Grant
    Filed: September 29, 1986
    Date of Patent: April 12, 1988
    Assignee: Ciba-Geigy Corporation
    Inventors: John A. Gannon, Joseph S. Puglisi, Vincent Brytus, Kenneth L. Payne
  • Patent number: 4707533
    Abstract: Vinyl ester resins are prepared by reacting a polyepoxide of a co-oligomerization product of a mixed cyanate of a polyphenol and a polymaleimide with a monounsaturated monocarboxylic acid.
    Type: Grant
    Filed: December 8, 1986
    Date of Patent: November 17, 1987
    Assignee: The Dow Chemical Company
    Inventor: Robert E. Hefner, Jr.
  • Patent number: 4677170
    Abstract: The invention relates to polyepoxides which are obtainable by reacting compounds of formula I ##STR1## wherein n is 1 or 2, and X, if n is 1, is a group R.sub.3, or, if n is 2, X is a group of the formula ##STR2## each of R.sub.1 and R.sub.3 independently of the other is C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, allyl, a halogen atom or C.sub.6 -C.sub.10 aryl and R.sub.2 is allyl, 1-propenyl or 2-propenyl, with compounds containing phenolic OH groups, and subsequently epoxidizing the resultant adducts in the presence of a peracid. Said polyepoxides can be used, together with customary epoxy resin hardeners, for the preparation of cured products, in particular for coating electronic components, or as adhesives.
    Type: Grant
    Filed: June 4, 1986
    Date of Patent: June 30, 1987
    Assignee: Ciba-Geigy Corporaton
    Inventors: Charles E. Monnier, Sheik Abdul-Cader Zahir
  • Patent number: 4661553
    Abstract: Vinyl ester resins are prepared by reacting a polyepoxide of a co-oligomerization product of a mixed cyanate of a polyphenol and a polymaleimide with a monounsaturated monocarboxylic acid.
    Type: Grant
    Filed: February 24, 1986
    Date of Patent: April 28, 1987
    Assignee: The Dow Chemical Company
    Inventor: Robert E. Hefner, Jr.
  • Patent number: 4639503
    Abstract: A thermosetting resin composition having an improved crack resistance comprising 100 weight parts of a curable epoxy resin and 30 to 300 weight parts of a phenol compound-added conjugated diolefin polymer, which is prepared in the presence of aluminum phenoxide as the catalyst. The composition is suitable for resin encapsulation of electronic components.
    Type: Grant
    Filed: November 15, 1985
    Date of Patent: January 27, 1987
    Assignee: Nippon Oil Co., Ltd.
    Inventors: Hajime Hara, Shingo Orii, Kazuho Aoyama, Masami Enomoto
  • Patent number: 4616066
    Abstract: A vinyl or acrylic polymer-modified epoxy resin comprising a reaction product of(A) an epoxy group-containing vinyl or acrylic polymer,(B) a bisphenol compound, and(C) a diglycidyl ether of a bisphenol compound.
    Type: Grant
    Filed: October 4, 1985
    Date of Patent: October 7, 1986
    Assignee: Kansai Paint Co., Ltd.
    Inventor: Akira Tominaga
  • Patent number: 4554213
    Abstract: Sheet steel used for making the cores of electrical machines is improved as to its punchability by coating it with a heat resistant coating of a complex mixture of phosphates and resins compatible with acid phosphate ions. The coating contains between 60 and 95% by weight of the phosphates and between 5 and 40% by weight of the resins. The resins can be acrylic base resins, ethylene-vinyl acetate copolymer resins, or thermosetting epoxy resins.
    Type: Grant
    Filed: November 29, 1984
    Date of Patent: November 19, 1985
    Assignees: Centro Sperimentale Metallurgico SpA, Terni - Societa per l'Industria e l'Elettricita SpA
    Inventors: Paolo Marini, Marcello Candiotti
  • Patent number: 4525572
    Abstract: A mixture consisting of a polymaleimide and a copolymerizable monomer or a prepolymer formed from these two compounds contains, as the polymerization catalyst, an ethane which is substituted by aromatic groups and hydroxyl groups or halogen (cf. formula II), such as benzpinacol. The mixture is stable on storage and heat-curable. It can be cured, while at the same time being shaped to give mouldings, sheet-like structures, laminates, adhesive bonds or foams, for example by casting or compression moulding.
    Type: Grant
    Filed: April 16, 1984
    Date of Patent: June 25, 1985
    Assignee: Ciba-Geigy Corporation
    Inventors: Hermann Diethelm, Sheik A. Zahir
  • Patent number: 4496709
    Abstract: Epoxy resins having improved properties are prepared by reacting an epoxy resin with a dihydric phenol in the presence of a sufficient quantity of a phosphonium trifluoroacetate catalyst such that the product resulting from reacting a mixture of the catalyst, epoxy resin and dihydric phenol has a % epoxide difference from the theoretical percent epoxide of from about 0.5 to about 4.0.
    Type: Grant
    Filed: June 16, 1983
    Date of Patent: January 29, 1985
    Assignee: The Dow Chemical Company
    Inventors: George A. Doorakian, Marsha A. Paul, Adolphus V. Gist
  • Patent number: 4412055
    Abstract: Phosphonopolyester oligomers are prepared from hydroxyalkylated 2,2',-bis(3-allylphenyl-4-hydroxy) alkanes and phosphonyl dihalides. The oligomers are useful in the preparation of polyester resins, epoxy resins, and polyurethanes.
    Type: Grant
    Filed: September 27, 1982
    Date of Patent: October 25, 1983
    Assignee: The Dow Chemical Company
    Inventor: Robert E. Hefner, Jr.
  • Patent number: 4394497
    Abstract: Solid compositions are prepared by reacting (A) one or more materials containing an average of more than one 1,2-epoxy groups with (B) one or more materials containing an average of more than one phenolic hydroxy groups wherein at least one of (A) or (B) contains with respect to (B) or has been prepared from with respect to (A) a reaction product of (1) at least one aromatic compound having at least one aromatic ring, at least one aromatic hydroxyl group and which aromatic ring contains at least one ortho or para position which is capable of being alkylated and (2) at least one aliphatic or cycloaliphatic C.sub.4 -C.sub.6 unsaturated hydrocarbon or a dimer, codimer, oligomer or cooligomer thereof.
    Type: Grant
    Filed: March 29, 1982
    Date of Patent: July 19, 1983
    Assignee: The Dow Chemical Company
    Inventors: Donald L. Nelson, Bryan A. Naderhoff
  • Patent number: 4393165
    Abstract: A polymer composition is herein disclosed, which consists essentially of:(A) 90 to 50 wt % of a saturated polymer having in one molecule (1) at least two groups of at least one type selected from the group consisting of an epoxy group of the formula ##STR1## (R is hydrogen or methyl), an alcoholic or phenolic hydroxyl group and an alkoxymethyl-substituted acid amide group of the formula ##STR2## (R is an alkyl group of C.sub.1 to C.sub.4) and (2) a repeating unit made of a nonaromatic methylene group or methine group; and(B) 50 to 10 wt % of a nonfunctional radical polymerizable monomer mixture consisting of (a) a radical polymerizable monomer having in one molecule at least one functional group selected from the group consisting of a carboxyl group, an acid anhydride group, an alcoholic hydroxyl group, an alkoxymethyl-substituted acid amide group of the formula ##STR3## (R is an alkyl group of C.sub.1 to C.sub.4) and an amino group of the formula --NR.sub.1 R.sub.2 (R.sub.1 and R.sub.
    Type: Grant
    Filed: August 9, 1982
    Date of Patent: July 12, 1983
    Assignee: Japan Atomic Energy Research Institute
    Inventors: Takashi Sasaki, Miyuki Hagiwara, Fumio Hosoi, Tohru Takagi
  • Patent number: 4390680
    Abstract: Epoxy resins are prepared by dehydrohalogenating the reaction product of an epoxy alkyl halide such as epichlorohydrin with the reaction product of an aromatic hydroxyl-containing compound such as phenol with an unsaturated hydrocarbon such as piperylene or isoprene or mixtures of dicyclopentadiene with other dimers or oligomers derived from C.sub.3 -C.sub.6 unsaturated hydrocarbons.
    Type: Grant
    Filed: March 29, 1982
    Date of Patent: June 28, 1983
    Assignee: The Dow Chemical Company
    Inventor: Donald L. Nelson
  • Patent number: 4384129
    Abstract: Mono- and polyvalent phenolglycidyl ethers which contain in the molecule at least one 1-propenyl group in the ortho- or para-position with respect to the glycidyl ether group, or isomeric mixtures of mono- or polyvalent phenolglycidyl ethers which are propenyl-substituted in the ortho or para-position with respect to the glycidyl ether group and mono- or polyvalent phenolglycidyl ethers which are allyl-substituted in the ortho- or para-position with respect to the glycidyl ether group, the proportion of propenyl groups in the isomeric mixture having to be at least 5 equivalent-%, relative to the sum of the equivalents of propenyl and allyl groups, are obtained by a process wherein the propenyl-substituted phenols, or isomeric mixtures of propenyl- and allyl-substituted phenols, are glycidylated with an epihalohydrin. The novel compounds can be converted, both by use of curing agents for epoxide resins and by radical polymerization, into polymers having valuable mechanical properties.
    Type: Grant
    Filed: April 27, 1981
    Date of Patent: May 17, 1983
    Assignee: Ciba-Geigy Corporation
    Inventors: Sheik A. Zahir, Sameer H. Eldin
  • Patent number: 4343843
    Abstract: A fiber reinforced epoxy resin article in which a Lewis base is employed as the catalyst for the addition reaction of a phenolic or alcoholic hydroxyl group and the oxirane group of the epoxy resin. The resin system has improved flexibility and pot life and the cured article has improved chemical resistance.
    Type: Grant
    Filed: August 28, 1980
    Date of Patent: August 10, 1982
    Assignee: A. O. Smith-Inland, Inc.
    Inventors: Junior L. Johnson, Leonard E. Pikey
  • Patent number: 4289812
    Abstract: Hydrophobic, thermoset resins having highly desirable properties in coatings applications can be prepared from novel, water-thinnable, base-neutralized, acidic reaction products of orthophosphoric acid with hydrophobic, nominally-difunctional polyether epoxide resins having average epoxide equivalent weights (EEW) of from about 172 to about 5500. The phosphate groups in these products, when formed with fugitive bases, are thermally decomposable to yield resins which are not rapidly self-converting as such but are rapidly heat convertible in admixture with any of several types of curing agents. The functional groups responsible for water solubilization are utilized (and reacted out) in curing of the resins. The invention provides a method of utilizing hydrophobic, high performance polyether epoxide type polymers in aqueous coating systems having the ability to wet metal surfaces.
    Type: Grant
    Filed: March 12, 1979
    Date of Patent: September 15, 1981
    Assignee: The Dow Chemical Company
    Inventor: Patrick H. Martin
  • Patent number: 4283521
    Abstract: A prepolymer is comprised of the reaction product of at least one aliphatic bismaleimide, at least one aromatic amine and at least one aromatic bismaleimide in combination with an aromatic and/or a cycloaliphatic epoxy resin providing at least two functional epoxy groups to provide a low temperature curable composition. The cured products are strongly adherent to a variety of substrates.
    Type: Grant
    Filed: February 14, 1979
    Date of Patent: August 11, 1981
    Assignee: TRW Inc.
    Inventor: Robert J. Jones
  • Patent number: 4282345
    Abstract: A method for preparing a resinous condensation product of an allylated phenol and an ethoxyline resin comprising reacting an allylated phenol with an ethoxyline resin in the presence of an acid catalyst and a compound selected from certain ketones and esters.
    Type: Grant
    Filed: April 16, 1980
    Date of Patent: August 4, 1981
    Assignee: General Electric Company
    Inventor: John D. Nelson
  • Patent number: 4273916
    Abstract: A prepolymer comprised of the reaction product of at least one aliphatic bismaleimide, at least one aromatic amine and at least one aromatic bismaleimide is combined with at least one cycloaliphatic epoxy resin having a melting point less than about 120.degree. F. and at least two functional epoxy groups to provide a low temperature curable composition. The cured products are strongly adherent to a variety of substrates.
    Type: Grant
    Filed: June 13, 1980
    Date of Patent: June 16, 1981
    Assignee: TRW Inc.
    Inventor: Robert J. Jones
  • Patent number: 4237035
    Abstract: An epoxy resin useful for coatings, adhesives and molding materials which is derived from a by-product tar produced as by-product in manufacturing resorcinol or resorcinol and hydroquinone via hydroperoxide of m-diisopropylbenzene or of a combination of m- and p-diisopropylbenzenes and containing m-substituted phenolic constituents or a combination of m- and p-substituted phenolic constituents as major constituents, or is derived from a polymerization product of said by-product tar.
    Type: Grant
    Filed: May 29, 1979
    Date of Patent: December 2, 1980
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Shuichi Kanagawa, Kazunori Kawakami, Akira Shintani
  • Patent number: 4220513
    Abstract: Polymerizable compositions comprise(a) a compound containing in the same molecule both at least one 1,2-epoxide group and at least two groups chosen from allyl, methallyl, and 1-propenyl groups, e.g., 2,2-bis(3-allyl-4-(glycidyloxy)phenyl)propane or bis(3-(1-propenyl)-4-(glycidyloxy)phenyl)methane, and(b) a compound containing at least two mercaptan groups per molecule, e.g., pentaerythritol tetrathioglycollate.The compositions are caused to polymerize by the action of irradiation or free-radical catalysts. They may, if desired, also contain a heat-curing crosslinking agent for epoxide resins; the epoxide-containing polymers so obtained can be subsequently crosslinked in situ. The compositions are useful in various two-stage operations, such as the production of multilayer printed circuits.
    Type: Grant
    Filed: January 19, 1979
    Date of Patent: September 2, 1980
    Assignee: Ciba-Geigy Corporation
    Inventors: George E. Green, Abdul-Cader Zahir
  • Patent number: 4196066
    Abstract: A cured or uncured linear aromatic polyester composition melt-blended and composed of(A) 100 parts by weight of a saturated linear aromatic polyester in which at least 70 mole % of the acid component consists of an aromatic dicarboxylic acid, and(B) 0.1 to 50 parts by weight of a reactive compound which is solid at room temperature or is a liquid having a boiling point of at least 200.degree. C. under atmospheric pressure, and which contains in its molecule at least one aliphatic unsaturated group substantially non-reactive with the polyester (A) and the aliphatic unsaturated group of the reactive compound (B) under conditions of melt-blending with the polyester (A) and at least one epoxy group reactive with the polyester (A) under the melt-blending conditions. The cured linear aromatic polyester composition can be prepared by extruding the uncured linear aromatic polyester composition under melting conditions, and subjecting the resulting extrudate to a curing treatment.
    Type: Grant
    Filed: June 30, 1978
    Date of Patent: April 1, 1980
    Assignee: Teijin Limited
    Inventors: Hiroo Inata, Makoto Ogasawara, Tsuto Morinaga, Akihiro Norike
  • Patent number: 4195152
    Abstract: There is disclosed a class of N-alkylpolyamines and their use as curing agents for epoxy resins, and in particular to such polyamines having the formula R--[NH(CH.sub.2).sub.x ].sub.y --NHR' where R is an aliphatic hydrocarbon radical having from 5 through 8 carbon atoms, R' is H, R or R", x is an integer of 2 or 3 and y is an integer of 2-4. A monoepoxide adduct of the monoalkyl substituted polyamine is also disclosed wherein R" may then become an aliphatic substituent (2-14 carbon atoms) which may contain (a) an oxygen atom, (b) a hydroxyl group or (c) an aromatic substituent such as a phenyl ring.
    Type: Grant
    Filed: July 20, 1978
    Date of Patent: March 25, 1980
    Assignee: Henkel Corporation
    Inventor: Don E. Floyd
  • Patent number: 4174333
    Abstract: Carboxylated amide polymers and coating compositions containing same are especially useful for the coating of food and beverage containers. The carboxylated amide polymers are the reaction product of (1) a compound of formula: ##STR1## wherein A is the organic residue resulting from a ring opening reaction of a 1,2-epoxy group on a polyepoxide with ammonia or amine, R.sub.1 is hydrogen or a C.sub.1-4 alkyl group, R.sub.2 is a C.sub.2-12 alkylene group, x is 0 or 1, y is from 0 to 4, R.sub.3 is hydrogen or a C.sub.1-6 alkyl group, R.sub.4 is hydrogen or a C.sub.1-6 alkyl group, provided at least one R.sub.1, R.sub.3 or R.sub.4 is hydrogen, and n is at least 1.0 with (2) a cyclic anhydride of a dibasic carboxylic acid. The carboxylated amide polymers can be made water reducible by neutralizing the polymer with an organic or inorganic base and used in aqueous coating compositions.
    Type: Grant
    Filed: November 2, 1978
    Date of Patent: November 13, 1979
    Assignee: PPG Industries, Inc.
    Inventors: Marvis E. Hartman, Thomas R. Hockswender
  • Patent number: 4153586
    Abstract: A process of making modified epoxy resins wherein a polyepoxide resin is reacted with a mercaptan compound of the formula HS--R--(COOX).sub.m wherein R is an organic radical having from 1 to 10 carbon atoms, X is hydrogen or a moiety formed by reacting the carboxyl group with a basic compound to form its salt and m is an integer of from 1 to 5. The compounds are reacted in the presence of a tin catalyst to produce resins of the structureB [--S--R--(COOX).sub.m ].sub.nwherein B is the residue from the ring opening reaction of an epoxide group on the polyepoxide resin molecule and the sulfhydryl hydrogen, R, X and m are as defined previously and n is at least 1. The aforementioned resins are produced without the need of a hydrolysis step.The modified epoxy resins are useful in formulating coating compositions having excellent physical and chemical properties. The resins can be dissolved or dispersed in water to form aqueous coating compositions.
    Type: Grant
    Filed: March 13, 1978
    Date of Patent: May 8, 1979
    Assignee: PPG Industries, Inc.
    Inventors: Thomas R. Hockswender, Marvis E. Hartman