Material Contains A Boron Atom Patents (Class 528/138)
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Patent number: 9152069Abstract: A toner including a binder resin, a colorant and a phenol multimer represented by the following General Formula (1): where R1 to R6, R11, R12, R14 to R16, R21, R22, and R24 to R26 each are a hydrogen atom or a substituent; and n is an integer.Type: GrantFiled: February 17, 2012Date of Patent: October 6, 2015Assignee: Ricoh Company, Ltd.Inventors: Masaki Watanabe, Hiroshi Yamashita, Satoyuki Sekiguchi
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Patent number: 9096790Abstract: Disclosed herein are free flowing coated particles and low temperature methods of making same. Each particle has a curable coating disposed upon a substrate. The substrate is a particulate substrate including an inorganic material, a particulate substrate including an organic material, a composite substantially homogeneous formed particle including a first portion of an at least partly cured binder and filler particles, or a hybrid particle having an inorganic particle as a core and a composite coating including at least partially cured resin and filler. The curable coating includes a continuous phase including a curable liquid resin and reactive powder particles embedded or adhered to the continuous phase. The reactive powder particles typically include one or more of a resole phenolic-formaldehyde resin, a novolak phenolic-formaldehyde resin, a polyester resin, an acrylic polymer resin, a urethane resin or an epoxy resin.Type: GrantFiled: October 26, 2009Date of Patent: August 4, 2015Assignee: HEXION INC.Inventors: Avis Lloyd McCrary, Robert Ray McDaniel, John W. Green
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Patent number: 8383862Abstract: Provided are a salt compound, cationic polymerization initiator and cationically polymerizable composition, which have a superior acid-generating capacity and high sensitivity, and are free from coloration. The salt compound is represented by the following general Formula (1): (wherein, R01 to R05 each independently represents a group selected from a hydrogen atom, a fluorine atom and —YR group, one of the R01 to R05 being a —YR group and at least two of the R01 to R05 being fluorine atoms; Y represents an oxygen atom or a sulfur atom; R represents a C1-C4 alkyl group; Ctp+ represents a p-valent cation, the p being 1 or 2; and n represents a coefficient required for maintaining electrical neutrality).Type: GrantFiled: October 28, 2008Date of Patent: February 26, 2013Assignee: Adeka CorporationInventors: Kentaro Kimura, Shohei Fujita, Tomoya Tamachi
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Publication number: 20110217554Abstract: A phenolic resin for shell molding is provided which generates less tar during casting and has low thermal expansion properties and high flexibility. Further, a process for producing the phenolic resin, RCS obtained by using the phenolic resin, and a shell mold obtained by using such RCS are provided. A phenolic resin having advantageous characteristics is obtained by reacting phenols and naphthols with aldehydes in the presence of at least one of divalent metal salt and oxalic acid which acts as catalyst.Type: ApplicationFiled: May 13, 2011Publication date: September 8, 2011Applicant: Asahi Organic Chemicals Industry Co., Ltd.Inventors: Keiichi MORI, Tomohiro TAKAMA
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Publication number: 20110015341Abstract: A phenol-formaldehyde resin, which can be obtained by alkalinically catalyzed condensation of phenol and formaldehyde in the presence of at least one salt of inorganic acids and by neutralization by means of an inorganic or organic acid following the condensation, wherein the production takes place with the addition of at least one compound of the formula R1—(CH2)n—R2, in which R1 and R2, independently of one another, stand for —C(O)R, —COOR, —CN, or —NO2, and R represents H or CH3, and n has the value of 1 or 2. Also disclosed are the production of such resins and their use as binders for mineral-fiber-based insulating products.Type: ApplicationFiled: January 21, 2008Publication date: January 20, 2011Applicant: Dynea OyInventors: Stefan Kowatsch, Karl Loidolt, Christoph Prock
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Patent number: 6881814Abstract: Phenolic resins and processes of making these phenolic resins that are useful for making binders for mineral wool insulation products are disclosed. The addition of a boron salt early in the process of making these phenolic resins leads to enhanced properties such as a reduction in the amount of tetradimers and an improvement in the stability of both the base resin and the pre-react.Type: GrantFiled: October 7, 2002Date of Patent: April 19, 2005Assignee: Dynea Canada Ltd.Inventors: Kwok Tang, Ruben A. Santos, Bohumila Zapletal
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Patent number: 6770107Abstract: A curable resin composition comprises a poly(arylene ether), an acryloyl monomer, an allylic monomer, and an abrasive filler. The composition tolerates high filler contents, cures rapidly, and exhibits excellent toughness after curing. Useful articles prepared from the composition include grinding wheels and cut-off wheels having good wear characteristics.Type: GrantFiled: January 30, 2003Date of Patent: August 3, 2004Assignee: General Electric CompanyInventors: Erich Otto Teutsch, Gary William Yeager, Kenneth Paul Zarnoch, Steven William Webb, Hua Guo
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Publication number: 20040068083Abstract: Phenolic resins and processes of making these phenolic resins that are useful for making binders for mineral wool insulation products are disclosed. The addition of a boron salt early in the process of making these phenolic resins leads to enhanced properties such as a reduction in the amount of tetradimers and an improvement in the stability of both the base resin and the pre-react.Type: ApplicationFiled: October 7, 2002Publication date: April 8, 2004Inventors: Kwok Tang, Ruben A. Santos, Bohumila Zapletal
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Patent number: 6593391Abstract: A curable resin composition comprises a poly(arylene ether), an acryloyl monomer, an allylic monomer, and an abrasive filler. The composition tolerates high filler contents, cures rapidly, and exhibits excellent toughness after curing. Useful articles prepared from the composition include grinding wheels and cut-off wheels having good wear characteristics.Type: GrantFiled: March 27, 2001Date of Patent: July 15, 2003Assignee: General Electric CompanyInventors: Erich Otto Teutsch, Gary William Yeager, Kenneth Paul Zarnoch, Steven William Webb, Hua Guo
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Patent number: 6139804Abstract: A process for producing a polyoxymethylene using a reactor having a discharging port having a weir, which process comprises introducing trioxane or a mixture of trioxane and a compound reactive therewith into the reactor from its feeding port and continuously recovering the powdery polyoxymethylene formed, from said discharging port having a weir. Owing to the presence of the weir, the residence time of reaction mixture in reactor is long, making high the conversion of the monomer.Type: GrantFiled: April 24, 1997Date of Patent: October 31, 2000Assignee: Asahi Kasei Kogyo Kabushiki KaishaInventors: Yukio Tanigawa, Hiromasa Matumoto
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Patent number: 6020452Abstract: A chiral biphenyl compound includes a hindered 2,2'-substituted-1,1'-biphenyl subunit and has the following formula: ##STR1## The chiral biphenyl compounds have been shown to be useful as catalysts in asymmetric reactions. For example, an organozinc species can be formed by reacting the chiral biphenyl compound with an organozinc compound, R.sup.14 R.sup.15 Zn and then used as a catalyst for the asymmetric alkylation of an aldehyde by an organozinc compound.Type: GrantFiled: August 26, 1997Date of Patent: February 1, 2000Assignee: North Dakota State UniversityInventors: Lin Pu, Wei-Sheng Huang, Qiao-Sheng Hu
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Patent number: 5889134Abstract: An organozinc species, useful in the reactions of aldehydes and ketones, is a reaction product of a) a biphenyl compound having one or more hindered 2,2'-substituted biphenyl subunits and b) an organozinc compound, such as diethylzinc. The organozinc species catalyzes the reduction of a ketone by a borane, as well as the epoxidation of .alpha.,.beta.-unsaturated compounds by an oxidizing agent, such as O.sub.2 or an alkyl hydroperoxide. The biphenyl compound may be chiral and may catalyze the formation of optically active reaction products.Type: GrantFiled: August 26, 1997Date of Patent: March 30, 1999Assignee: North Dakota State UniversityInventors: Lin Pu, Wei-Sheng Huang, Qiao-Sheng Hu
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Patent number: 5614349Abstract: The present invention provides methods for producing water insoluble, aqueous alkali soluble novolak resins having a precise and consistent molecular weight, by adjusting the concentration of Lewis base. A method is also provided for producing photoresist composition from such novolak resins and for producing semiconductor devices using such photoresist compositions.Type: GrantFiled: December 29, 1992Date of Patent: March 25, 1997Assignee: Hoechst Celanese CorporationInventors: M. Dalil Rahman, Daniel P. Aubin, Dana L. Durham, Ralph R. Dammel
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Patent number: 5359024Abstract: The invention relates to a process for the preparation of a phenol-formaldehyde resin by causing phenol and formaldehyde to condense under the influence of a basic catalyst, the catalyst being an aqueous solution containing alkali metal ions, carbonate ions, ions of carboxylic acids and one or more ions chosen from the group comprising transition metal ions and borates.Type: GrantFiled: August 17, 1993Date of Patent: October 25, 1994Assignee: DSM N.V.Inventors: Renier H. M. Kierkels, van Kempen Carolien H. M., Henricus A. C. Baur
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Patent number: 5357039Abstract: Poly-N-acylalkyleneimines corresponding to the following formula ##STR1## are used as an oxidatively crosslinking constituent in paints. In formula (I), R--CO represents the acyl radical of a mono- or polyunsaturated, aliphatic C.sub.16-22 carboxylic acid or a mixture of such radicals, R'--CO represents the acyl radical of a C.sub.1-22 carboxylic acid or a mixture of such radicals and x and y represent the percentages by weight of the particular polymer units, x assuming values of 20 to 100% and preferably 20 to 95% and y assuming values of 80 to 0% and preferably 80 to 5%. The indices m and n independently of one another may assume the value 2 or 3.Type: GrantFiled: April 26, 1993Date of Patent: October 18, 1994Assignee: Henkel Kommanditgesellschaft auf AktienInventors: Brigitte Hase, Ulrich Eicken, Herbert Fischer, Horst-Juergen Krause, Wolfgang Gress, Norbert Stork
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Patent number: 5294648Abstract: A binder composition for producing articles of bonded particulate material such as foundry molds or core comprises an alkaline aqueous solution of a resol phenol-aldehyde resin, an oxyanion which can form a stable complex with the resin, and an ethylene glycol monoalkyl ether. The binder composition has an alkali to phenol molar ratio of from 1.5:1 to 2.5:1 and the amount of alkali present in the solution is sufficient to substantially prevent stable complex formation between the resin ad the oxyanion. Bonded articles are produced by passing carbon dioxide gas through articles formed from a mixture of particulate material and the binder composition so as to produce stable complex formation and curing of the resin.Type: GrantFiled: January 4, 1993Date of Patent: March 15, 1994Assignee: Foseco International LimitedInventors: Garry Smith, Martin Bradley
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Patent number: 5290843Abstract: The present invention is directed to a phenolic resin composition useful for preparing a binder for reinforced composites, to a binder for reinforced composites made using the phenolic resin composition, and to a reinforced composite made using the binder. The phenolic resin composition of the present invention contains an aqueous mixture of: (a) a resole formed by reacting phenol with formaldehyde in the presence of an ortho directing catalyst at a mole ratio of formaldehyde to phenol ranging from about 0.7:1 to about 3:1 and (b) a water-soluble borate, wherein the composition contains at least about 0.02 equivalent of the ortho directing catalyst per mole of phenol, has a pH at least about 7 and contains from about 0.02 to about 0.5 mole borate per mole of phenol. When the ortho directing catalyst has a cation that forms an insoluble material with a borate anion, the cation is removed after the resole is formed and prior to adding the water-soluble borate.Type: GrantFiled: April 29, 1993Date of Patent: March 1, 1994Assignee: Georgia-Pacific Resins, Inc.Inventors: Roderick A. McDonald, Mark J. Knudsen
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Patent number: 5281644Abstract: There are disclosed methods and compositions for retarding the ambient temperature hardening of a phenolic resole resin alone or with an aggregate when such resin is contacted with a nitroalkane and a hardening agent such as lightburned magnesium oxide, an organic ester functional hardening agent, and mixtures of lightburned magnesium oxide and an organic ester functional hardening agent in an alkaline medium. There is also disclosed a hardener composition for phenolic resole resins wherein the hardener composition consists essentially of a solution of a nitroalkane in an organic ester functional hardening agent.Type: GrantFiled: November 4, 1992Date of Patent: January 25, 1994Assignee: Borden, Inc.Inventors: S. Raja Iyer, David R. Armbruster, Arthur H. Gerber
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Patent number: 5254664Abstract: A reaction of the compound (A) having at least two 2-oxazoline groups with the compound (B) having at least two functional groups of one or a plural kind selected from the group consisting of an aromatic hydroxyl group, an amino group and a thiol group proceeds in a short period of time to produce a cured resin with superior mechanical strength, heat resistance and adhesion properties.Type: GrantFiled: December 31, 1991Date of Patent: October 19, 1993Assignee: Nippon Shokubai Co., Ltd.Inventors: Subhash C. Narang, Asutosh Nigam, Apparao Satyam, Susanna C. Ventura, Yoshihiro Arita
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Patent number: 5242957Abstract: A binder composition for producing articles of bonded particulate material such as foundry molds or cores comprises an alkaline aqueous solution of a resol phenol-aldehyde resin, an oxyanion which can form a stable complex with the resin, and a phenyl ethylene glycol ether. The binder composition has an alkali to phenol molar ratio of from 1.5:1 to 2.5:1 and the amount of alkali present in the solution is sufficient to substantially prevent stable complex formation between the resin and the oxyanion. Bonded articles are produced by passing carbon dioxide gas through articles formed from a mixture of particulate material and the binder composition so as to produce stable complex formation and curing of the resin.Type: GrantFiled: February 13, 1992Date of Patent: September 7, 1993Assignee: Foseco International LimitedInventors: Garry Smith, Martin Bradley
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Patent number: 5233020Abstract: Poly-N-acylalkyleneimines corresponding to the following formula ##STR1## are used as an oxidatively crosslinking constituent in paints. In formula (I), R--CO represents the acyl radical of a mono- or polyunsaturated, aliphatic C.sub.16-22 carboxylic acid or a mixture of such radicals, R'--CO represents the acyl radical of a C.sub.1-22 carboxylic acid or a mixture of such radicals and x and y represent the percentages by weight of the particular polymer units, x assuming values of 20 to 100% and preferably 20 to 95% and y assuming values of 80 to 0% and preferably 80 to 5%. The indices m and n independently of one another may assume the value 2 or 3.Type: GrantFiled: July 12, 1991Date of Patent: August 3, 1993Assignee: Henkel Kommanditgesellschaft auf AktienInventors: Brigitte Hase, Ulrich Eicken, Herbert Fischer, Horst-Jurgen Krause, Wolfgang Gress, Norbert Stork
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Patent number: 5075413Abstract: A fire resistant resin for use as a binder in reinforced plastics and a resultant reinforced plastic includes the reaction product of (a) at least one resorcinol component selected from the group consisting of resorcinol and resorcinol formaldehyde novolak resin, and (b) a phenolic resole resin. The reaction may be achieved in the presence of an alkaline catalyst.A method of making a fire resistant resin binder for reinforced plastics and the method of making such reinforced plastics including, (a) at least one resorcinol component selected from the group consisting of resorcinol and resorcinol formaldehyde novolak resin, and (b) a phenolic resole resin. The reaction may be achieved in the presence of an alkaline catalyst.Type: GrantFiled: September 4, 1990Date of Patent: December 24, 1991Assignee: Indspec Chemical CorporationInventor: Theodore H. Dailey, Jr.
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Patent number: 5075414Abstract: A fire resistant resin for use as a binder in reinforced plastics and a resultant reinforced plastic includes the reaction product of (a) at least one resorcinol component selected from the group consisting of resorcinol and resorcinol formaldehyde novolak resin, and (b) a phenolic resole resin. The reaction may be achieved in the presence of an alkaline catalyst.A method of making a fire resistant resin binder for reinforced plastics and the method of making such reinforced plastics including, (a) at least one resorcinol component selected from the group consisting of resorcinol and resorcinol formaldehyde novolak resin, and (b) a phenolic resole resin. The reaction may be achieved in the presence of an alkaline catalyst.Type: GrantFiled: September 4, 1990Date of Patent: December 24, 1991Assignee: Indspec Chemical CorporationInventor: Theodore H. Dailey, Jr.
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Patent number: 5032431Abstract: A dark colored glass fiber insulation having improved moisture tolerance prepared using an aqueous phenolic resole resin composition containing a water soluble borate and cured under alkaline conditions.Type: GrantFiled: February 6, 1990Date of Patent: July 16, 1991Assignee: Georgia-Pacific Resins, Inc.Inventors: Rodney R. Conner, Mary L. Foster
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Patent number: 5021522Abstract: An improved vulcanizable rubber composition of the type comprising (I) a rubber component selected from natural rubber, synthetic rubber or combinations thereof, and (II) a methylene donor compound which generates formaldehyde upon heating, and (III) a phenolic novolak resin type methylene acceptor compound is disclosed. The improvement comprises having at least ten mole percent of the phenolic groups of the phenolic novolak resin aralkylated with one or more compounds selected from the group consisting of styrene, alpha methyl styrene, beta methyl styrene, p-methyl styrene, alpha chloro styrene and vinyl naphthalenes.Type: GrantFiled: February 21, 1990Date of Patent: June 4, 1991Assignee: Indspec Chemical CorporationInventors: Bojayan Durairaj, Alex Peterson, Jr., Robert M. Lamars, Richard T. Hood
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Patent number: 4985489Abstract: A binder composition for producing articles of bonded particulate material such as foundry moulds or cores comprises an alkaline aqueous solution of a resol phenol-aldehyde resin and an oxyanion capable of forming a stable complex with the resin the amount of alkali present in the solution being sufficient to substantially prevent stable complex formation. Bonded articles are produced from mixtures of particulate material and the binder composition by passing carbon dioxide gas through the formed articles whereby the oxyanion forms a stable complex with the resin and the resin is cured. The oxyanion may be for example borate, stannate or aluminate.Type: GrantFiled: September 29, 1989Date of Patent: January 15, 1991Assignee: Foseco International LimitedInventors: Sidney A. Barker, Neil Baggett, John Stevenson, Raymond D. George, David R. De Courcy, Timothy Hammond, Martin Bradley
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Patent number: 4977209Abstract: A binder composition for producing articles of bonded particulate material such as foundry moulds or cones comprises an alkaline aqueous solution of a resol phenol-aldehyde resin and an oxyanion capable of forming a stable complex with the resin the amount of alkali present in the solution being sufficient to substantially prevent stable complex formation. Bonded articles are produced from mixtures of particulate material and the binder composition by passing carbon dioxide gas through the formed articles whereby the oxyanion forms a stable complex with the resin and the resin is cured. The oxyanion may be for example borate, stannate or aluminate.Type: GrantFiled: December 6, 1988Date of Patent: December 11, 1990Assignee: Foseco International LimitedInventors: Sidney A. Barker, Neil Baggett, John Stevenson, Raymond D. George, David R. De Courcy, Timothy Hammond, Martin Bradley
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Patent number: 4904753Abstract: Disclosed is a catalyst system which improves the cure time of acid-catalyzable resole resins while providing extended shelf life thereof. Broadly, the present invention includes a method for formulating an acid-catalyzed, non-aqueous resole resin composition and to the composition itself. The catalyst system comprises an acid catalyst and an oxidizing agent in an amount adequate for cure in at least about the same time that occurs by use of at least twice the amount of said acid catalyst alone. The shelf life of the catalyzed resole resin is greater with the inventive catalyst system than with an equivalent resole resin containing only the acid catalyst in twice the amount.Type: GrantFiled: March 23, 1988Date of Patent: February 27, 1990Assignee: Ashland Oil, Inc.Inventors: Golden F. Watts, Warren L. Robbins
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Patent number: 4841002Abstract: Compositions have melting points below 100.degree. C. which are useful in the formation of resins by reaction with polyphenolic compounds consisting of a mixture of more than two compounds having the formula ##STR1## wherein A represents a cyclic or acyclic aliphatic or substituted cyclic or acyclic aliphatic moiety having from 1 to 20 carbon atoms or an aromatic mono- or multi-nuclear or aliphatic substituted aryl residue having from 6 to 20 carbon atoms,R independently represents H, CH.sub.3, CH.sub.2 CH.sub.3 or C.sub.6 H.sub.5,R.sup.1 independently represents H or CH.sub.3,R.sup.2 independently represents H or CH.sub.3, andx represents an integer from 0 to 2are described.Type: GrantFiled: November 8, 1988Date of Patent: June 20, 1989Assignee: Ashland Oil, IncInventors: Billy M. Culbertson, Omar Tiba
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Patent number: 4839446Abstract: A polymerizable thermosetting composition which is a flowable liquid at moderate temperatures which comprises a mixture of:(A) from about 75% to about 95% by weight of a mixture of:(1) from about 80% to about 20% by weight of a bisoxazoline and(2) from about 20% to about 80% by weight of a polyphenolic compound and(B) from about 5% to about 25% by weight of at least one member selected from the group consisting of a monooxazoline and a monooxazine,a method for forming thermoset products therefrom and the novel thermoset products resulting from said method are described.Type: GrantFiled: August 8, 1988Date of Patent: June 13, 1989Assignee: Ashland Oil, Inc.Inventors: Billy M. Culbertson, Omar Tiba
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Patent number: 4820576Abstract: A flame-retardant polymer is created by forming a first resin typically by reacting resorcinol with furfural in a ratio of one mole of the former to less than a mole of the latter in the presence of an alkaline catalyst. A resole is then formed by reacting typically phenol with formaldehyde in a ratio of one mole of phenol to more than a mole of the aldehyde in the presence of an alkaline catalyst. The first resin and resole are mixed together with a powered oxyborate compound such as zinc borate and allowed to polymerize to form the polymer.Type: GrantFiled: February 18, 1988Date of Patent: April 11, 1989Assignee: Fiber Materials, Inc.Inventor: Harold E. Duryea
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Patent number: 4746719Abstract: A process for preparing copolymers of a mixture of a bis-oxazoline and a polyphenolic compound at improved rate of copolymerization by the inclusion of a catalytic amount of a carbonium ion salt of the formula Ph.sub.3 CX wherein Ph represents a phenyl group and X represents BF.sub.4, PF.sub.6, SbF.sub.6, AsF.sub.6, BPh.sub.4 or ClO.sub.4, is described.Type: GrantFiled: June 3, 1987Date of Patent: May 24, 1988Assignee: Ashland Oil, Inc.Inventors: Anil B. Goel, Omar Tiba
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Patent number: 4650840Abstract: There are disclosed thermosetting resoles containing chemically bonded boron, tungsten and/or zirconium atoms. The metal containing resoles of this invention are useful, for example, as reimpregnation resins.Type: GrantFiled: October 11, 1985Date of Patent: March 17, 1987Assignee: HitcoInventor: Paul V. Mosher
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Patent number: 4639496Abstract: Method for the manufacture of a polymer with triaromatic methane units as basic building blocks, the electric conductivity of which is obtained through the formation of charge transfer complexes. Electron donors and/or electron acceptors are added to the synthetic polymer during or after its preparation, for forming charge transfer complexes.Type: GrantFiled: August 29, 1985Date of Patent: January 27, 1987Assignee: Brown, Boveri & Cie AGInventors: Gerd Weddigen, Robert Huber, Birgit Schmidt, Hartmut Schneider
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Patent number: 4613662Abstract: A process comprising copolymerizing an oxazoline with a bis-or poly-phenolic compound in the presence of a catalyst which is a cationic complex of an alkali or an alkaline earth metal at a temperature in the range of from about 100.degree. to 200.degree. C. is described.Type: GrantFiled: August 7, 1985Date of Patent: September 23, 1986Assignee: Ashland Oil, Inc.Inventor: Anil B. Goel
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Patent number: 4593052Abstract: Polymerizable compositions contain (A) a cationically polymerizable material, such as an epoxide resin, a phenoplast or a cyclic vinyl ether, (B) a hydroxy compound such as styreneallyl alcohol copolymer, and (c) an aromatic iodosyl salt of formula ##STR1## where R.sup.3 and R.sup.4, which may be the same or different, each represent a monovalent aromatic radical having from 4 to 25 carbon atoms, x denotes 1, 2 or 3, and Z.sup.x- denotes an x-valent anion of a protic acid.Suitable salts of formula II include diphenyliodosyl hexafluorophosphate and tetrafluoroborate. The compositions may be photopolymerized or they may be thermally polymerized in the presence, as catalyst for the iodosyl salt, of a salt or complex of a d-block transition metal, a stannous salt, an organic peroxide or an activated .alpha.-hydroxy compound.The compositions may be used as surface coatings and adhesives, and in the preparation of printing plates, printed circuits and reinforced composites.Type: GrantFiled: November 19, 1984Date of Patent: June 3, 1986Assignee: Ciba-Geigy CorporationInventor: Edward Irving
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Patent number: 4585837Abstract: There are disclosed thermosetting resoles containing chemically bonded boron, tungsten and/or zirconium atoms. The metal containing resoles of this invention are useful, for example, as reimpregnation resins.Type: GrantFiled: January 16, 1985Date of Patent: April 29, 1986Assignee: HitcoInventor: Paul V. Mosher
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Patent number: 4398014Abstract: New aromatic sulfonylsulfoxonium salts are of formula ##STR1## where q is 1 to 4,R denotes an aliphatic, cycloaliphatic, or aromatic group,R.sup.6 denotes H, an alkyl or aralkyl group, or a group --COR.sup.9, --CO--NH--(CO).sub.r --R.sup.10, or --SO.sub.2 --R.sup.11, where r is zero or 1,one, but not both, of R and R.sup.6 denoting an aromatic group,R.sup.7 denotes an alkyl, alkenyl, cycloalkyl, cycloalkylalkyl, or aralkyl group,R.sup.8 has the same meaning as R.sup.7 but may alternatively represent a dialkylamino group or, if R.sup.7 denotes alkyl, it may alternatively represent an arylamino group,R.sup.9, R.sup.10, and R.sup.11 each denote an alkyl, aryl, or aralkyl radical of 1 to 25 carbon atoms,t is 1, 2, or 3, andZ.sup.- denotes a t-valent anion of a protic acid.The salts, e.g., dimethyl-p-toluenesulfonylmethylsufoxonium hexafluorophosphate, are useful as catalysts for the polymerization of cationically polymerizable materials by means of actinic radiation and/or heat.Type: GrantFiled: October 23, 1981Date of Patent: August 9, 1983Assignee: Ciba-Geigy CorporationInventors: George E. Green, Edward Irving, Bernard P. Stark
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Patent number: 4382130Abstract: Certain aryloxyphosphonium salts have been found to be effective as curing agents for various cationically polymerizable organic materials, such as epoxy resins, when incorporated into such materials. The materials are found to be moisture curable coating compositions.Type: GrantFiled: October 14, 1981Date of Patent: May 3, 1983Assignee: General Electric CompanyInventors: Robert H. Ellison, Martin A. Byrne
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Patent number: 4345054Abstract: A high-molecular-weight novolak type substituted phenolic resin having a number average molecular weight of at least 1500 is prepared by reacting (A) (i) a phenol comprised mainly of a bifunctional phenol or (ii) a low-molecular-weight novolak type substituted phenolic resin derived from this phenol and an aldehyde with (B) a chain extender selected from the group consisting of (i) a dimethylolated product of a bifunctional or trifunctional phenol, (ii) a low-molecular-weight resol type substituted phenolic resin derived from a phenol comprised mainly of a bifunctional phenol and an aldehyde, (iii) an aldehyde, (iv) a ketone, (v) a diol and (vi) a dihalide in the presence of an acid catalyst, with the proviso that if the reactant (A) is the phenol (i), the chain extender is the resol type substituted phenolic resin (ii).Type: GrantFiled: December 29, 1980Date of Patent: August 17, 1982Assignee: Mitsui Petrochemical Industries, Ltd.Inventors: Nobuyuki Takeda, Tadao Iwata
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Patent number: 4339567Abstract: Substances (I) capable of being converted into higher-molecular weight materials under the influence of a cationic catalyst, such as 1,2-epoxides, aminoplasts, vinyl monomers or prepolymers, or phenoplasts, are so converted by exposure to actinic radiation in the presence of a sulphoxonium salt (II) of formula ##STR1## where P denotes zero or 1,R.sup.6 denotes an arylene or aralkylene group,R.sup.7 denotes --H or a group of formula ##STR2## R.sup.8 denotes an alkyl, alkenyl, cycloalkyl, cycloalkylalkyl, aryl, or aralkyl group,R.sup.9 has the same meaning as R.sup.8 but may alternatively represent a dialkylamino group or, if R.sup.8 represents an alkyl group, R.sup.9 may represent an arylamino group,R.sup.10 and R.sup.11 each independently have the same meaning as R.sup.8 but may also each denote --H,r represents 1, 2, or 3,Z.sup.r- denotes an r-valent anion of a protic acid, and q denotes zero when p denotes zero, or zero or 1 when p denotes 1.Type: GrantFiled: February 23, 1981Date of Patent: July 13, 1982Assignee: Ciba-Geigy CorporationInventors: George E. Green, Edward Irving
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Patent number: 4336366Abstract: Cationically polymerizable compounds, for example cyclic ethers, can be thermally polymerised if an aromatic iodonium salt of the formula I[(Ar.sup.1)(Ar.sup.2)I].sup.+ [MX.sub.n ].sup.- (I)in which Ar.sup.1 Ar.sup.2, M, X and n are as defined in claim 1, is used as the catalyst and an agent which forms free radicals on heating and has the formula III or IV ##STR1## in which R.sup.2, R.sup.3, R.sup.5, R.sup.6, R.sup.8 and m are as defined in claim 1, for example a benzpinacol silyl ether, is used as the co-catalyst. The process is of particular importance for heat-curing epoxide resins as a one-component system.Type: GrantFiled: February 20, 1981Date of Patent: June 22, 1982Assignee: Ciba-Geigy CorporationInventors: Godwin Berner, Rudolf Kirchmayr
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Patent number: 4323667Abstract: Concentrated boric anhydride solutions containing more than 5% of boric anhydride in an organic solvent selected from mono or polyalcohols, trialkylborate and/or dialkylacetal when the solvent also contains an acid selected from sulfuric acid and/or aromatic acids. These solutions are used as hardeners of formo-phenolic resols, more particularly for the manufacture of laminates comprising glass fibers and formo-phenolic resols.Type: GrantFiled: January 22, 1981Date of Patent: April 6, 1982Assignee: Societe Chimique des Charbonnages SAInventors: Nicolas Meyer, Raymond Foulon
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Patent number: 4309527Abstract: Flame retardant polymer resins formed by an acid condensation reaction from a mixture of resorcinol and furfural with a molar excess of the aldehyde. In one particular embodiment the resin is formed of a mixture of two prepolymer solutions with at least a boric acid catalyst, one or both of the prepolymer solutions being an acid-condensation reaction product of resorcinol and furfural with excess aldehyde functionality, or one of the prepolymers being a mix of substantially unreacted resorcinol and furfural with a slight molar excess of aldehyde.Type: GrantFiled: February 9, 1981Date of Patent: January 5, 1982Assignee: Fiber Materials, Inc.Inventors: Lawrence E. McAllister, Herbert Dietrich
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Patent number: 4299938Abstract: Substances (I) capable of being converted into higher-molecular weight materials under the influence of a cationic catalyst, such as 1,2-epoxides, aminoplasts, vinyl monomers or prepolymers, or phenoplasts, are so converted by exposure to actinic irradiation or by heating in the presence of an aryloxysulfoxonium salt of formula ##STR1## where either R.sup.6 and R.sup.7 separately denote lower alkyl (optionally substituted by halogen and interrupted in the chain by --O-- or --SO.sub.2 --), or an aryl or aryloxy group, or R.sup.6 and R.sup.7 together denote a divalent group forming with the S atom a heterocyclic radical; R.sup.8 denotes an aryl group; M denotes an atom of a metal or metalloid; X denotes a halogen atom; and n is 4, 5, or 6, for instance,p-chlorophenoxy-p-tolyl-p-phenoxysulfoxonium hexafluorophosphate and 1-phenoxy-1-oxidotetrahydrothiophenium tetrafluorborate.Type: GrantFiled: June 9, 1980Date of Patent: November 10, 1981Assignee: Ciba-Geigy CorporationInventors: George E. Green, Edward Irving
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Patent number: 4275170Abstract: Flame retardant polymer resins formed by an acid condensation reaction from a mixture of resorcinol and furfural with a molar excess of the aldehyde. In one particular embodiment the resin is formed of a mixture of two prepolymer solutions with at least a boric acid catalyst, one or both of the prepolymer solutions being an acid-condensation reaction product of resorcinol and furfural with excess aldehyde functionality, or one of the prepolymers being a mix of substantially unreacted resorcinol and furfural with a slight molar excess of aldehyde.Type: GrantFiled: September 7, 1979Date of Patent: June 23, 1981Assignee: Fiber Materials, Inc.Inventors: Lawrence E. McAllister, Herbert Dietrich
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Patent number: 4272403Abstract: Concentrated boric anhydride solutions containing more than 5% of boric anhydride in an organic solvent selected from mono or polyalcohols, trialkylborate and/or dialkylacetal when the solvent also contains an acid selected from sulfuric acid and/or aromatic acids. These solutions are used as hardeners of formo-phenolic resols, more particularly for the manufacture of laminates comprising glass fibers and formo-phenolic resols.Type: GrantFiled: June 15, 1979Date of Patent: June 9, 1981Assignee: Societe Chimiques des Charbonnages SAInventors: Nicolas Meyer, Raymond Foulon
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Patent number: 4259473Abstract: Self-curing or curable materials are obtained from the distillation residues of coal hydrogenation by condensing a residue of this type having a softening point of 30.degree. to 54.degree. C. in a first stage with a mono- or dihydroxybenzene and/or a methylhydroxybenzene and/or an ethylene substituted benzene. These reactants are used at a ratio of residue to benzene derivative between 1:1 and 2:1 and the reaction is carried out in the presence of acid at a pH of 1 to 2 and at a temperature of 90.degree. to 100.degree. C. In a second stage the thus obtained reaction product is then further reacted at about the same temperature with an aldehyde. As a result a novolak-type resin is obtained. The invention permits the making of inexpensive self-curing or curable materials with properties similar to those of phenolic acids. Besides, the invention also provides an outlet for the high boiling residue of the extractive coal hydrogenation which otherwise had little use.Type: GrantFiled: January 15, 1980Date of Patent: March 31, 1981Assignee: Bergwerksverband GmbHInventors: Ingo Romey, Menachem El-Roy
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Process for the production of white melamine-phenol-aldehyde resins which are resistant to yellowing
Patent number: 4229557Abstract: Resins which are substantially white and resistant to yellowing are obtained by the addition of ammonium or alkali phosphates or ammonium or alkali borates during the production or processing of melamine-phenol-aldehyde resins in an aqueous basic medium, and by subsequently obtaining the resin by dehydration at a temperature of at least 70.degree. C.Type: GrantFiled: August 27, 1979Date of Patent: October 21, 1980Assignee: Ciba-Geigy CorporationInventors: Dieter Feinauer, Ludwig Streinz -
Patent number: 4176216Abstract: The present invention provides particular phenol/formaldehyde resoles which are especially useful as foamable resins, and further provides cellular phenolic products having physical properties which are especially attractive for end-use application as construction foam. The resoles are characterized by a particular relationship between their viscosity and water content, expressed as the area bounded by certain points on a plot of resole viscosity on a logarithmic scale, as a function of water content of the resole, the particular area depending upon the mole ratio of formaldehyde-to-phenol at which the resole has been condensed. It has been found that phenol-formaldehyde resoles having the defined viscosity/water relationship are capable of providing phenolic foam having acceptable foam processability, a foam density from about 1.90 to about 3.Type: GrantFiled: September 29, 1978Date of Patent: November 27, 1979Assignee: Union Carbide CorporationInventors: Wallace G. Reid, Rakesh Saini, Kenneth E. Atkins