Material Contains A Boron Atom Patents (Class 528/138)
  • Patent number: 9152069
    Abstract: 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: Grant
    Filed: February 17, 2012
    Date of Patent: October 6, 2015
    Assignee: Ricoh Company, Ltd.
    Inventors: Masaki Watanabe, Hiroshi Yamashita, Satoyuki Sekiguchi
  • Patent number: 9096790
    Abstract: 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: Grant
    Filed: October 26, 2009
    Date of Patent: August 4, 2015
    Assignee: HEXION INC.
    Inventors: Avis Lloyd McCrary, Robert Ray McDaniel, John W. Green
  • Patent number: 8383862
    Abstract: 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: Grant
    Filed: October 28, 2008
    Date of Patent: February 26, 2013
    Assignee: Adeka Corporation
    Inventors: Kentaro Kimura, Shohei Fujita, Tomoya Tamachi
  • Publication number: 20110217554
    Abstract: 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: Application
    Filed: May 13, 2011
    Publication date: September 8, 2011
    Applicant: Asahi Organic Chemicals Industry Co., Ltd.
    Inventors: Keiichi MORI, Tomohiro TAKAMA
  • Publication number: 20110015341
    Abstract: 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: Application
    Filed: January 21, 2008
    Publication date: January 20, 2011
    Applicant: Dynea Oy
    Inventors: Stefan Kowatsch, Karl Loidolt, Christoph Prock
  • Patent number: 6881814
    Abstract: 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: Grant
    Filed: October 7, 2002
    Date of Patent: April 19, 2005
    Assignee: Dynea Canada Ltd.
    Inventors: Kwok Tang, Ruben A. Santos, Bohumila Zapletal
  • Patent number: 6770107
    Abstract: 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: Grant
    Filed: January 30, 2003
    Date of Patent: August 3, 2004
    Assignee: General Electric Company
    Inventors: Erich Otto Teutsch, Gary William Yeager, Kenneth Paul Zarnoch, Steven William Webb, Hua Guo
  • Publication number: 20040068083
    Abstract: 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: Application
    Filed: October 7, 2002
    Publication date: April 8, 2004
    Inventors: Kwok Tang, Ruben A. Santos, Bohumila Zapletal
  • Patent number: 6593391
    Abstract: 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: Grant
    Filed: March 27, 2001
    Date of Patent: July 15, 2003
    Assignee: General Electric Company
    Inventors: Erich Otto Teutsch, Gary William Yeager, Kenneth Paul Zarnoch, Steven William Webb, Hua Guo
  • Patent number: 6139804
    Abstract: 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: Grant
    Filed: April 24, 1997
    Date of Patent: October 31, 2000
    Assignee: Asahi Kasei Kogyo Kabushiki Kaisha
    Inventors: Yukio Tanigawa, Hiromasa Matumoto
  • Patent number: 6020452
    Abstract: 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: Grant
    Filed: August 26, 1997
    Date of Patent: February 1, 2000
    Assignee: North Dakota State University
    Inventors: Lin Pu, Wei-Sheng Huang, Qiao-Sheng Hu
  • Patent number: 5889134
    Abstract: 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: Grant
    Filed: August 26, 1997
    Date of Patent: March 30, 1999
    Assignee: North Dakota State University
    Inventors: Lin Pu, Wei-Sheng Huang, Qiao-Sheng Hu
  • Patent number: 5614349
    Abstract: 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: Grant
    Filed: December 29, 1992
    Date of Patent: March 25, 1997
    Assignee: Hoechst Celanese Corporation
    Inventors: M. Dalil Rahman, Daniel P. Aubin, Dana L. Durham, Ralph R. Dammel
  • Patent number: 5359024
    Abstract: 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: Grant
    Filed: August 17, 1993
    Date of Patent: October 25, 1994
    Assignee: DSM N.V.
    Inventors: Renier H. M. Kierkels, van Kempen Carolien H. M., Henricus A. C. Baur
  • Patent number: 5357039
    Abstract: 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: Grant
    Filed: April 26, 1993
    Date of Patent: October 18, 1994
    Assignee: Henkel Kommanditgesellschaft auf Aktien
    Inventors: Brigitte Hase, Ulrich Eicken, Herbert Fischer, Horst-Juergen Krause, Wolfgang Gress, Norbert Stork
  • Patent number: 5294648
    Abstract: 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: Grant
    Filed: January 4, 1993
    Date of Patent: March 15, 1994
    Assignee: Foseco International Limited
    Inventors: Garry Smith, Martin Bradley
  • Patent number: 5290843
    Abstract: 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: Grant
    Filed: April 29, 1993
    Date of Patent: March 1, 1994
    Assignee: Georgia-Pacific Resins, Inc.
    Inventors: Roderick A. McDonald, Mark J. Knudsen
  • Patent number: 5281644
    Abstract: 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: Grant
    Filed: November 4, 1992
    Date of Patent: January 25, 1994
    Assignee: Borden, Inc.
    Inventors: S. Raja Iyer, David R. Armbruster, Arthur H. Gerber
  • Patent number: 5254664
    Abstract: 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: Grant
    Filed: December 31, 1991
    Date of Patent: October 19, 1993
    Assignee: Nippon Shokubai Co., Ltd.
    Inventors: Subhash C. Narang, Asutosh Nigam, Apparao Satyam, Susanna C. Ventura, Yoshihiro Arita
  • Patent number: 5242957
    Abstract: 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: Grant
    Filed: February 13, 1992
    Date of Patent: September 7, 1993
    Assignee: Foseco International Limited
    Inventors: Garry Smith, Martin Bradley
  • Patent number: 5233020
    Abstract: 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: Grant
    Filed: July 12, 1991
    Date of Patent: August 3, 1993
    Assignee: Henkel Kommanditgesellschaft auf Aktien
    Inventors: Brigitte Hase, Ulrich Eicken, Herbert Fischer, Horst-Jurgen Krause, Wolfgang Gress, Norbert Stork
  • Patent number: 5075413
    Abstract: 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: Grant
    Filed: September 4, 1990
    Date of Patent: December 24, 1991
    Assignee: Indspec Chemical Corporation
    Inventor: Theodore H. Dailey, Jr.
  • Patent number: 5075414
    Abstract: 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: Grant
    Filed: September 4, 1990
    Date of Patent: December 24, 1991
    Assignee: Indspec Chemical Corporation
    Inventor: Theodore H. Dailey, Jr.
  • Patent number: 5032431
    Abstract: 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: Grant
    Filed: February 6, 1990
    Date of Patent: July 16, 1991
    Assignee: Georgia-Pacific Resins, Inc.
    Inventors: Rodney R. Conner, Mary L. Foster
  • Patent number: 5021522
    Abstract: 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: Grant
    Filed: February 21, 1990
    Date of Patent: June 4, 1991
    Assignee: Indspec Chemical Corporation
    Inventors: Bojayan Durairaj, Alex Peterson, Jr., Robert M. Lamars, Richard T. Hood
  • Patent number: 4985489
    Abstract: 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: Grant
    Filed: September 29, 1989
    Date of Patent: January 15, 1991
    Assignee: Foseco International Limited
    Inventors: Sidney A. Barker, Neil Baggett, John Stevenson, Raymond D. George, David R. De Courcy, Timothy Hammond, Martin Bradley
  • Patent number: 4977209
    Abstract: 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: Grant
    Filed: December 6, 1988
    Date of Patent: December 11, 1990
    Assignee: Foseco International Limited
    Inventors: Sidney A. Barker, Neil Baggett, John Stevenson, Raymond D. George, David R. De Courcy, Timothy Hammond, Martin Bradley
  • Patent number: 4904753
    Abstract: 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: Grant
    Filed: March 23, 1988
    Date of Patent: February 27, 1990
    Assignee: Ashland Oil, Inc.
    Inventors: Golden F. Watts, Warren L. Robbins
  • Patent number: 4841002
    Abstract: 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: Grant
    Filed: November 8, 1988
    Date of Patent: June 20, 1989
    Assignee: Ashland Oil, Inc
    Inventors: Billy M. Culbertson, Omar Tiba
  • Patent number: 4839446
    Abstract: 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: Grant
    Filed: August 8, 1988
    Date of Patent: June 13, 1989
    Assignee: Ashland Oil, Inc.
    Inventors: Billy M. Culbertson, Omar Tiba
  • Patent number: 4820576
    Abstract: 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: Grant
    Filed: February 18, 1988
    Date of Patent: April 11, 1989
    Assignee: Fiber Materials, Inc.
    Inventor: Harold E. Duryea
  • Patent number: 4746719
    Abstract: 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: Grant
    Filed: June 3, 1987
    Date of Patent: May 24, 1988
    Assignee: Ashland Oil, Inc.
    Inventors: Anil B. Goel, Omar Tiba
  • Patent number: 4650840
    Abstract: 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: Grant
    Filed: October 11, 1985
    Date of Patent: March 17, 1987
    Assignee: Hitco
    Inventor: Paul V. Mosher
  • Patent number: 4639496
    Abstract: 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: Grant
    Filed: August 29, 1985
    Date of Patent: January 27, 1987
    Assignee: Brown, Boveri & Cie AG
    Inventors: Gerd Weddigen, Robert Huber, Birgit Schmidt, Hartmut Schneider
  • Patent number: 4613662
    Abstract: 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: Grant
    Filed: August 7, 1985
    Date of Patent: September 23, 1986
    Assignee: Ashland Oil, Inc.
    Inventor: Anil B. Goel
  • Patent number: 4593052
    Abstract: 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: Grant
    Filed: November 19, 1984
    Date of Patent: June 3, 1986
    Assignee: Ciba-Geigy Corporation
    Inventor: Edward Irving
  • Patent number: 4585837
    Abstract: 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: Grant
    Filed: January 16, 1985
    Date of Patent: April 29, 1986
    Assignee: Hitco
    Inventor: Paul V. Mosher
  • Patent number: 4398014
    Abstract: 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: Grant
    Filed: October 23, 1981
    Date of Patent: August 9, 1983
    Assignee: Ciba-Geigy Corporation
    Inventors: George E. Green, Edward Irving, Bernard P. Stark
  • Patent number: 4382130
    Abstract: 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: Grant
    Filed: October 14, 1981
    Date of Patent: May 3, 1983
    Assignee: General Electric Company
    Inventors: Robert H. Ellison, Martin A. Byrne
  • Patent number: 4345054
    Abstract: 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: Grant
    Filed: December 29, 1980
    Date of Patent: August 17, 1982
    Assignee: Mitsui Petrochemical Industries, Ltd.
    Inventors: Nobuyuki Takeda, Tadao Iwata
  • Patent number: 4339567
    Abstract: 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: Grant
    Filed: February 23, 1981
    Date of Patent: July 13, 1982
    Assignee: Ciba-Geigy Corporation
    Inventors: George E. Green, Edward Irving
  • Patent number: 4336366
    Abstract: 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: Grant
    Filed: February 20, 1981
    Date of Patent: June 22, 1982
    Assignee: Ciba-Geigy Corporation
    Inventors: Godwin Berner, Rudolf Kirchmayr
  • Patent number: 4323667
    Abstract: 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: Grant
    Filed: January 22, 1981
    Date of Patent: April 6, 1982
    Assignee: Societe Chimique des Charbonnages SA
    Inventors: Nicolas Meyer, Raymond Foulon
  • Patent number: 4309527
    Abstract: 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: Grant
    Filed: February 9, 1981
    Date of Patent: January 5, 1982
    Assignee: Fiber Materials, Inc.
    Inventors: Lawrence E. McAllister, Herbert Dietrich
  • Patent number: 4299938
    Abstract: 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: Grant
    Filed: June 9, 1980
    Date of Patent: November 10, 1981
    Assignee: Ciba-Geigy Corporation
    Inventors: George E. Green, Edward Irving
  • Patent number: 4275170
    Abstract: 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: Grant
    Filed: September 7, 1979
    Date of Patent: June 23, 1981
    Assignee: Fiber Materials, Inc.
    Inventors: Lawrence E. McAllister, Herbert Dietrich
  • Patent number: 4272403
    Abstract: 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: Grant
    Filed: June 15, 1979
    Date of Patent: June 9, 1981
    Assignee: Societe Chimiques des Charbonnages SA
    Inventors: Nicolas Meyer, Raymond Foulon
  • Patent number: 4259473
    Abstract: 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: Grant
    Filed: January 15, 1980
    Date of Patent: March 31, 1981
    Assignee: Bergwerksverband GmbH
    Inventors: Ingo Romey, Menachem El-Roy
  • Patent number: 4229557
    Abstract: 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: Grant
    Filed: August 27, 1979
    Date of Patent: October 21, 1980
    Assignee: Ciba-Geigy Corporation
    Inventors: Dieter Feinauer, Ludwig Streinz
  • Patent number: 4176216
    Abstract: 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: Grant
    Filed: September 29, 1978
    Date of Patent: November 27, 1979
    Assignee: Union Carbide Corporation
    Inventors: Wallace G. Reid, Rakesh Saini, Kenneth E. Atkins