Aldehyde Or Derivative Is Sole Coreactant Patents (Class 528/165)
  • Patent number: 5473045
    Abstract: A phenolic novolak composition prepared by a process comprising the steps of:(1) reacting a first phenolic monomer comprising a major portion of at least one trifunctional phenolic monomer with a first aldehyde source in the absence of a catalyst at a reaction temperature from about 100.degree. C. to about 200.degree. C. and at a reaction pressure of about 2 to about 15 atmospheres to form a phenolic oligomer having a weight average molecular weight from about 500 to about 2,000, having ortho--ortho bonding of about 55% to about 75% of the methylene bonds between the phenolic moieties; and having a time to clear of less than 125 seconds per micron; wherein the mole ratio of said first aldehyde source to said first phenolic monomer is from about 0.3:1.0 to about 0.55:1.0; and(2) then reacting said oligomer with an optional second phenolic source and a second aldehyde source at a temperature from about 80.degree. C. to about 150.degree. C.
    Type: Grant
    Filed: January 17, 1995
    Date of Patent: December 5, 1995
    Assignee: OCG Microelectronic Materials, Inc.
    Inventors: Joseph J. Sizensky, Thomas R. Sarubbi, Medhat A. Toukhy
  • Patent number: 5412058
    Abstract: New formaldehyde-phenol resins of the novolak type comprising aliphatic aldehyde radicals with 6 or more carbon atoms and with the molar ratio between these heavy aldehyde radicals and the phenolic structures being between 0.9 and 1.2. They are obtained by the condensation of phenols with aldehyde compounds containing at least 543% heavy aldehydes in the presence of acid catalysts in a virtually anhydrous medium. Application to the reinforcement of vulcanized rubbers.
    Type: Grant
    Filed: September 14, 1990
    Date of Patent: May 2, 1995
    Assignee: CECA S.A.
    Inventors: Thierry Dreyfus, Noel Le Bourt
  • Patent number: 5378791
    Abstract: This invention relates to a process for producing low molecular weight phenol-aldehyde resin which has predominantly 4 phenolic units in a chain and in which the phenolic ring has a substituent R which is an alkyl group and optionally contains methylol groups on either end of the chain, by reacting formaldehyde with p-alkyl phenol in the presence of ammonia as base in a liquid reaction medium. The resins can be used in producing demulsifiers.
    Type: Grant
    Filed: May 5, 1993
    Date of Patent: January 3, 1995
    Assignee: BP Chemicals Limited
    Inventors: Michael Lancaster, David J. Moreton, Alexander F. Psaila
  • Patent number: 5372879
    Abstract: The present invention provides a biaxially oriented polyester film made of a polyester containing 0.01 to 5% by weight of crosslinked polymer particles characterized by:(1) having a particle size distribution ratio (.gamma.) of 1.3 to 3.5,(2) having an average particle diameter of 0.1 to 2 .mu.m,(3) having a non-circularity of 3.4 or more, and(4) having a standard deviation of noncircularity, of at least 0.16.The polyester film of the present invention has a flat surface having a small number of large protuberances, excellent running property and excellent winding property, and can be produced economically. The film has excellent properties for use as a base for various magnetic recording media.
    Type: Grant
    Filed: February 18, 1994
    Date of Patent: December 13, 1994
    Assignee: Teijin Limited
    Inventors: Makoto Handa, Tomoyuki Kishino
  • Patent number: 5367040
    Abstract: A process for the production of modified phenol-formaldehyde resins includes the use of a difunctional phenolic compound as the phenolic component of the resins. The inventive resins resist pre-curing and are useful in the production of molded wood composites produced, for example, by wet-dry forming processes.
    Type: Grant
    Filed: December 29, 1992
    Date of Patent: November 22, 1994
    Assignee: Masonite Corporation
    Inventor: Zygmunt Teodorczyk
  • Patent number: 5358748
    Abstract: Described is an acidic glass fiber binding composition comprising an aqueous soluble phenol formaldehyde resin having low free formaldehyde, an effective amount of a formaldehyde scavenger, and an effective amount of a strong aqueous soluble acid, wherein the composition has an acidic pH and the solids content ranges from about 1 to about 30% by weight of the total composition. Also described is a method of binding glass fibers such as newly formed warm glass fibers at junctions of the fibers by applying the composition as described above to the fibers and then drying the composition. Also described are B-staged and C-staged glass fiber compositions having a alkylamine content less than 5 ppm.
    Type: Grant
    Filed: May 19, 1992
    Date of Patent: October 25, 1994
    Assignee: Schuller International, Inc.
    Inventors: Dale J. Mathews, Philip F. Miele, Edmund G. Dornfeld
  • Patent number: 5350827
    Abstract: A novolak resin composition comprising at least one unit of the reaction product of a para-, para-bonded bisphenol having formula (A): ##STR1## wherein R.sub.1 =hydrogen, lower alkyl group having 1-4 carbon atoms, halogen, or lower alkoxy group having 1-4 carbon atoms;wherein R.sub.2 =hydrogen or lower alkyl group having 1-4 carbon atoms; andwherein X is selected from the group consisting of: CH.sub.2, CH(CH.sub.3), C(CH.sub.3).sub.2, O, and S;with a bismethylol monomer selected from a difunctional ortho-, ortho-phenolic bismethylol of Formula (B), a difunctional ortho-, para-phenolic bismethylol of Formula (C): ##STR2## wherein R.sub.3 is selected from CH.sub.3, CH.sub.2 CH.sub.3, Cl, and Br; andwherein R.sub.4 is selected from H and CH.sub.3.
    Type: Grant
    Filed: February 9, 1994
    Date of Patent: September 27, 1994
    Assignee: OCG Microelectronic Materials, Inc.
    Inventors: Thomas R. Sarubbi, Joseph J. Sizensky
  • Patent number: 5344909
    Abstract: A latent catalyzed phenolic resin composition is provided containing a thermosetting phenolic resole resin and a latent catalyst consisting essentially of a primary or secondary amine salt of a strong acid.
    Type: Grant
    Filed: June 3, 1993
    Date of Patent: September 6, 1994
    Assignee: Georgia-Pacific Resins, Inc.
    Inventors: David A. Hutchings, Ted M. McVay, Richard F. Pennock
  • Patent number: 5319063
    Abstract: A phenolic resin can be obtained by a condensation reaction between a specific trifunctional aromatic compound and a phenolic compound. This resin can be reacted with a curing agent such as a hexamine to give cured articles having excellent heat resistance, electrical properties, wear resistance and chemical resistance, and the phenolic resin is also much more excellent in curing reactivity as compared with conventional techniques.
    Type: Grant
    Filed: January 15, 1993
    Date of Patent: June 7, 1994
    Assignee: Mitsui Toatsu Chemicals, Incorporated
    Inventors: Shinji Ando, Yukio Fukui, Shigeru Iimuro
  • Patent number: 5296584
    Abstract: The invention relates to a composition consisting of a melamine solid suspended or dispersed in a resole resin. The method of the invention favors the intermolecular condensation polymerization reaction between phenol and melamine, rather than homopolymerization between phenol molecules or between melamine molecules. This invention reduces formaldehyde emissions by favoring a reaction whose by-product is water rather than formaldehyde. The compositions are useful for bonding glass fiber mats used for thermal and acoustical insulation.
    Type: Grant
    Filed: July 22, 1993
    Date of Patent: March 22, 1994
    Assignee: Borden, Inc.
    Inventor: Wayne R. Walisser
  • Patent number: 5250653
    Abstract: A phenolic novolak resin composition comprising a condensation product of at least one aldehyde source with a phenolic source comprising 5-indanol. Said phenolic novolak resins are used in radiation-sensitive compositions, especially those useful as positive-working photoresists.
    Type: Grant
    Filed: February 22, 1993
    Date of Patent: October 5, 1993
    Assignee: OCG Microelectronic Materials, Inc.
    Inventor: Medhat A. Toukhy
  • Patent number: 5243015
    Abstract: A latent catalyzed phenolic resin composition is provided containing a thermosetting phenolic resole resin and a latent catalyst consisting essentially of a primary or secondary amine salt of a strong acid.
    Type: Grant
    Filed: June 25, 1992
    Date of Patent: September 7, 1993
    Assignee: Georgia-Pacific Resins, Inc.
    Inventors: David A. Hutchings, Ted M. McVay, Richard F. Pennock
  • Patent number: 5216111
    Abstract: An essentially aromatic alkali soluble novolak resin comprising the product resulting from the acid condensation of an aromatic aldehyde and a phenol where the resin has a molecular weight in excess of 1500 and a glass transition temperature in excess of 125.degree. C. If desired, the aromatic novolak resin may be blended with a conventional novolak resin to regulate the glass transition temperature of the resin. The aromatic novolak resin and blends formed therefrom are especially suitable as coating resins and are useful for the formation of photoresist coating compositions.
    Type: Grant
    Filed: October 22, 1990
    Date of Patent: June 1, 1993
    Assignee: Shipley Company Inc.
    Inventor: Anthony Zampini
  • Patent number: 5216112
    Abstract: A phenolic resin can be obtained by a condensation reaction between a specific trifunctional aromatic compound and a phenolic compound. This resin can be reacted with a curing agent such as a hexamine to give cured articles having excellent heat resistance, electrical properties, wear resistance and chemical resistance, and the phenolic resin is also much more excellent in curing reactivity as compared with conventional techniques.
    Type: Grant
    Filed: August 15, 1991
    Date of Patent: June 1, 1993
    Assignee: Mitsui Toatsu Chemicals, Inc.
    Inventors: Shinji Ando, Yukio Fukui, Shigeru Iimuro
  • Patent number: 5151496
    Abstract: The 2-functional component of substituted phenol-aldehyde novolac resins is reduced. Epoxy novolac resins prepared from the novolac resin containing reduced quantities of 2-functional product exhibit increased Tg values when cured.
    Type: Grant
    Filed: December 18, 1991
    Date of Patent: September 29, 1992
    Assignee: The Dow Chemical Company
    Inventors: James L. Bertram, Louis L. Walker, Avis L. McCrary, Fermin M. Cortez
  • Patent number: 5106923
    Abstract: The 2-functional component of substituted phenol-aldehyde novolac resins is reduced. Epoxy novolac resins prepared from the novolac resin containing reduced quantities of 2-functional product exhibit increased Tg values when cured.
    Type: Grant
    Filed: February 21, 1991
    Date of Patent: April 21, 1992
    Assignee: The Dow Chemical Company
    Inventors: James L. Bertram, Louis L. Walker, Avis L. McCrary, Fermin M. Cortez
  • Patent number: 5089589
    Abstract: The preparation of novolaks from phenols or mixtures of different phenols, and oxo compounds or mixtures of oxo compounds by condensation of the reactants in a medium having a low water content in homogeneous phase at temperature of .gtoreq.110.degree. C., preferably between 115.degree. and 200.degree. C. and preferably at normal pressure, in the presence of water-immiscible and/or only partially water-miscible inert organic solvents and of acids as catalysts with removal of water by distillation, the medium having a low water content being prepared or maintained by distilling off water from the reaction mixture, preferably by azeotropic distillation. Particular advantages are obtained when readily volatile oxo compounds, in particular aqueous formaldehyde solutions, are used.
    Type: Grant
    Filed: January 22, 1990
    Date of Patent: February 18, 1992
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Wolfgang Hesse, Klaus Hofmann, Erhard Leicht
  • Patent number: 5079314
    Abstract: Phenol-aldehyde novolac resins having reduced quantities of 2-functional material are prepared by removing all or part of the 2-functional material from this product resulting from reacting phenol with an aldehyde. Epoxy novolac resins prepared from the novolac resin containing less 2-functional product exhibit increased Tg values when cured.
    Type: Grant
    Filed: November 17, 1989
    Date of Patent: January 7, 1992
    Assignee: The Dow Chemical Company
    Inventors: James L. Bertram, Louis L. Walker, Avis L. McCrary, Fermin M. Cortez
  • Patent number: 5074946
    Abstract: It has now been found that when there is a partial or complete replacement of the sodium hydroxide that is used to make a sodium phenolate resole resin by a molar equivalent of potassium hydroxide, a far faster curing resin is obtained. Such potassium-modified phenolic resins exhibit significant improvement in cure speed without loss of flowability. To the contrary, these resins act as though they were lower molecular weight condensation products. Reduced application rates are possible. The combination of faster cure and lower application rates has allowed such resins to be used as effective adhesives for plywood, for example, with veneer and interior plies having a higher moisture content than was previously possible. Generally, resins according to the invention may contain from about 1% to about 14%, and preferably from about 1% to about 7% by weight, of potassium hydroxide, or more.
    Type: Grant
    Filed: July 18, 1988
    Date of Patent: December 24, 1991
    Assignee: Borden, Inc.
    Inventor: Nick K. Daisy
  • Patent number: 5073622
    Abstract: The invention relates to a process for the preparation of novolak resins having a low amount of metal ions. In the process, a conventional resin in an organic solution is brought into contact with an acidic, preferably complex-forming compound which preferably is present in an aqueous phase. The resin solutions may be used in the production of photoresists.
    Type: Grant
    Filed: July 10, 1990
    Date of Patent: December 17, 1991
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Bernhard Wojtech, Walter Niederstaetter, Horst-Dieter Thamm
  • Patent number: 5053479
    Abstract: A phenolic novolak resin comprising the product of a condensation reaction of an aldehyde comprising a haloacetaldehyde source or a mixture of a haloacetaldehyde source and a formaldehyde source with a phenolic monomer comprising at least one compound of the formula: ##STR1## wherein R.sub.1, R.sub.2 and R.sub.3 are individually selected from hydrogen or a one to four carbon alkyl group and wherein the ratio of total carbon atoms in the sum of R.sub.1, R.sub.2 and R.sub.3 to the total number of phenolic nuclei in said resin is from about 0.5:1 to about 1.5:1 in the presence of a solvent; said resin made by employing a molar ratio of total aldehyde to total phenolic monomers from about 0.33:1 to about 0.70:1. These phenolic resins are suitable for use in light-sensitive compositions (e.g. positive-working photoresists).
    Type: Grant
    Filed: June 18, 1990
    Date of Patent: October 1, 1991
    Assignee: OCG Microelectronic Materials, Inc.
    Inventors: Andrew J. Blakeney, Thomas Sarubbi, Joseph J. Sizensky
  • Patent number: 5023311
    Abstract: Disclosed is a novel, organic solvent-soluble novolak resin having a high molecular weight and an inherent viscosity of at least 0.1. This high-molecular-weight novolak resin can be prepared with a good reproducibility by reacting an aldehyde with a polyfunctional phenol at an aldehyde/polyfunctional phenol molar ratio of from 0.85 to 1.20 in the presence of an acid catalyst in a solution state. This high-molecular-weight novolak resin is valuable as the resin component of a radiation-sensitive resist.
    Type: Grant
    Filed: November 30, 1988
    Date of Patent: June 11, 1991
    Assignee: Toray Industries, Inc.
    Inventor: Takashi Kubota
  • Patent number: 4965324
    Abstract: The 2-functional component of substituted phenol-aldehyde novolac resins is reduced. Epoxy novolac resins prepared from the novolac resin containing reduced quantities of 2-functional product exhibit increased Tg values when cured.
    Type: Grant
    Filed: November 17, 1989
    Date of Patent: October 23, 1990
    Assignee: The Dow Chemical Company
    Inventors: James L. Bertram, Louis L. Walker, Avis L. McCrary, Fermin M. Cortez
  • Patent number: 4839445
    Abstract: The present invention relates to a process for producing spherical thermosetting phenolic resin particles having a size of no larger than about 1,000 microns, and the spherical thermosetting phenolic resin particles produced by this process.In accordance with the process of the present invention, a novolak resin, and a nitrogenous basic compound, and, optionally, an aldehyde, are reacted while they are suspended in an aqueous medium in the presence of a suspension stabilizer.The thermosetting phenolic resin produced by the process of the present invention not only displays superior thermal curing characteristics during molding; the cured product fabricated by molding this resin also exhibits good physical properties such as improved mechanical strength and heat resistance. Therefore, the spherical thermosetting phenolic resin particles produced by the process of the present invention can be extensively used as molding materials, binders, adhesives, and in many other applications.
    Type: Grant
    Filed: January 6, 1988
    Date of Patent: June 13, 1989
    Assignee: Unitika, Ltd.
    Inventors: Yoshiaki Echigo, Kenichi Sugawara, Mutsunori Yamao, Yoshiyuki Suematu, Keiichi Asami, Tuneyuki Ohsawa
  • Patent number: 4758478
    Abstract: It has now been found that when there is a partial or complete replacement of the sodium hydroxide that is used to make a sodium phenolate resole resin by a molar equivalent of potassium hydroxide, a far faster curing resin is obtained. Such potassium-modified phenoli resins exhibit significant improvement in cure speed without loss of flowability. To the contrary, these resins act as though they were lower molecular weight condensation products. Reduced application rates are possible. The combination of faster cure and lower application rates has allowed such resins to be used as effective adhesives for plywood, for example, with veneer and interior plies having a higher moisture content than was previously possible. Generally, resins according to the invention may contain from about 1% to about 15%, and preferably from about 1% to about 7% by weight, of potassium hydroxide, or more.
    Type: Grant
    Filed: September 30, 1986
    Date of Patent: July 19, 1988
    Inventors: Nick K. Daisy, Dale L. Leeper
  • Patent number: 4757118
    Abstract: Modified phenolic resins and cured resins prepared therefrom.
    Type: Grant
    Filed: January 23, 1986
    Date of Patent: July 12, 1988
    Assignee: Allied Corporation
    Inventors: Sajal Das, Dusan C. Prevorsek
  • Patent number: 4668759
    Abstract: A process for preparing modified phenolic resole resins providing improved binders for refractories and foundry cores and molds. The resins are prepared by treating a phenol with a molar excess of aldehyde in the presence of an alkaline catalyst followed by further reaction at a pH below 7 in the presence of a catalyst which promotes formation of ortho-ortho benzylic ether bridges between the phenolic nuclei.
    Type: Grant
    Filed: July 31, 1985
    Date of Patent: May 26, 1987
    Assignee: Acme Resin Corporation
    Inventors: Raja Iyer, Rasik C. Shah
  • Patent number: 4656239
    Abstract: The process described herein involves the gradual addition of aqueous formaldehyde, containing 35-60 percent by weight of formaldehyde, to a phenol maintained at a temperature of 60.degree.-100.degree. C., preferably 70.degree.-90.degree. C., and at a reduced pressure of 11-26 inches of mercury in the presence of an alkaline catalyst. The rate of formaldehyde addition is such that the exothermic reaction aids in maintaining the stated temperature range and thereby simultaneously distills approximately all the water added with the formaldehyde and that formed by the condensation so that the volume of the reaction mass is maintained approximately constant. This constant volume allows efficient use of the equipment.
    Type: Grant
    Filed: March 27, 1986
    Date of Patent: April 7, 1987
    Assignee: Plastics Engineering Company
    Inventors: Phillip A. Waitkus, Bohumir Lepeska
  • Patent number: 4649188
    Abstract: The 2-functional content of phenol-aldehyde novolac resins is reduced by water extraction. Epoxy novolac resins prepared from the novolac resin containing less 2-functional product exhibit increased Tg values when cured.
    Type: Grant
    Filed: January 13, 1986
    Date of Patent: March 10, 1987
    Assignee: The Dow Chemical Company
    Inventors: James L. Bertram, Louis L. Walker, Avis L. McCrary, Fermin M. Cortez
  • Patent number: 4640971
    Abstract: A resole resin in the form of microspherical particles whose surfaces are partly or entirely covered with a coating of a substantially water-insoluble inorganic salt and which are not larger than 500 .mu.m in size, and a process for producing such resole resin. The resole resin comprises solid particles that are highly heat reactive and can be stored in a stable manner for a prolonged period. The resin particles can be used with good results in all fields of applications (e.g., moldings, laminations and binders) where conventional phenolic resins are used.
    Type: Grant
    Filed: July 17, 1985
    Date of Patent: February 3, 1987
    Assignee: Unitika Ltd.
    Inventors: Yoshiaki Echigo, Mutsunori Yamao, Yoshiyuki Suematu, Tadashi Ishikura, Keiichi Asami, Ritsuko Shidei
  • 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: 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: 4578448
    Abstract: Disclosed are high-ortho phenol-formaldehyde resoles having stable hemiformal groups. These resoles are of low viscosity, are essentially free of unbound water and volatile organic compounds. They are curable to phenolic formaldehyde resinous solids and are particularly suitable for use in liquid injection molding processes to form composites.
    Type: Grant
    Filed: December 14, 1983
    Date of Patent: March 25, 1986
    Assignee: Union Carbide Corporation
    Inventors: George L. Brode, Sui-Wu Chow
  • Patent number: 4564466
    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: December 21, 1983
    Date of Patent: January 14, 1986
    Assignee: Brown, Boveri & Cie AG
    Inventors: Gerd Weddigen, Robert Huber, Birgit Schmidt, Hartmut Schneider
  • Patent number: 4542204
    Abstract: A method for a condensate of an aldehyde compound and a phenol compound, said method comprising dispersing a viscous condensate obtained by the reaction of an aldehyde compound with a phenol compound into cold water or hot water by the aid of a dispersing agent, and then solidifying said condensate.
    Type: Grant
    Filed: October 28, 1983
    Date of Patent: September 17, 1985
    Assignee: Kanegafuchi Kagaku Kogyo Kabushiki Kaisha
    Inventors: Hiroshi Shibahara, Hiromitsu Tachibana
  • Patent number: 4483788
    Abstract: An electroviscous (EV) fluid composition whose fluid properties are altered in the presence of an electric field comprises water-containing particles of a phenol-formaldehyde polymer dispersed in a non-conducting liquid. The composition, selected from the broad range of fluid compositions of UK Pat. No. 1570234, possesses improved fluid properties combined with markedly reduced electrical conductivity, and is thus more suitable for use in applications such as at the interface between electronics and power hydraulics for example.In a preferred embodiment of the present invention the polymer comprises the dilithium salt of 2,2', 4,4' tetrahydroxybenzophenone condensed with formaldehyde, dispersed at 30% V/V in a mixture of brominated diphenyl methane (BDM) liquid components having the averaged formula C.sub.6 H.sub.4 Br.CH.sub.2.C.sub.6 H.sub.5.
    Type: Grant
    Filed: March 14, 1983
    Date of Patent: November 20, 1984
    Assignee: The National Research Development Corp.
    Inventors: James E. Stangroom, Ian Harness
  • Patent number: 4468507
    Abstract: Large-scale preparation of branched novolacs by the acid catalyzed, exothermic condensation of methylol-reactive phenols with polymethylol diphenols is made practical by first carrying out the reaction on a scale which permits temperature control simply by cooling and then separately adding more of the premixed reactants and the catalyst at rates such that the temperature of the reaction mixture can readily be controlled.
    Type: Grant
    Filed: November 21, 1983
    Date of Patent: August 28, 1984
    Assignee: The Dow Chemical Company
    Inventor: Theodore L. Parker
  • Patent number: 4454298
    Abstract: A granular or powdery resin which is a condensation product of a phenol and an aldehyde and optionally a nitrogen-containing compound having at least two active hydrogens, said granular or powdery resin being characterized by(A) containing spherical primary particles and secondary particles resulting from the agglomeration of the primary particles, each of said particles having a particle diameter of 0.1 to 150 microns,(B) having such a size that at least 50% by weight thereof can pass through a 100 Tyler mesh sieve,(C) having a free phenol content, determined by liquid chromatography, of not more than 500 ppm, and(D) having a methanol solubility (S) of more than 20% by weight when about 10 g of the resin is heated under reflux in 500 ml of substantially anhydrous methanol.
    Type: Grant
    Filed: December 23, 1982
    Date of Patent: June 12, 1984
    Assignee: Kanebo Ltd.
    Inventors: Hiroaki Koyama, Shigeo Shimizu
  • Patent number: 4433119
    Abstract: There are described liquid compositions of a hemiformal of phenol and/or a hemiformal of a methylolated phenol with a miscible polymers such as phenol-formaldehyde resoles, phenol-formaldehyde, novolacs, aromatic polyesters, unsaturated polyesters, poly(aryl-ethers), aromatic polycarbonates urea-formaldehyde resins, or melamine-formaldehyde resins. The compositions are useful for forming thermoset plastic materials.
    Type: Grant
    Filed: January 19, 1982
    Date of Patent: February 21, 1984
    Assignee: Union Carbide Corporation
    Inventors: George L. Brode, Sui-Wu Chow
  • Patent number: 4427800
    Abstract: Refractory shaped articles are prepared by heating refractory mixes comprised of refractory particles and a liquid phenolic resole resin having a methylol group index of about 0.8 or less and a free moisture content of about 8 weight percent or less.
    Type: Grant
    Filed: February 12, 1982
    Date of Patent: January 24, 1984
    Assignee: Sumitomo Durez Company, Ltd.
    Inventors: Masayuki Nakamura, Masaaki Tsuriya
  • Patent number: 4424300
    Abstract: Phenol-formaldehyde resin powder capable of both heat softening and fast-cure is produced by spray drying a blend of resole and novolac prepolymers. The powder, when mixed, heated and pressed with wax-coated wood chips, flows and cures to form a superior, bonded flake waferboard.
    Type: Grant
    Filed: September 29, 1982
    Date of Patent: January 3, 1984
    Assignee: Borden, Inc.
    Inventors: Otto G. Udvardy, Patricia E. Titus, Martin Navratil
  • Patent number: 4414379
    Abstract: A granular or powdery nitrogen-containing phenol-aldehyde copolymer resin which is a condensation product of a phenol, a nitrogen-containing compound having at least two active hydrogen atoms and an aldehyde, said granular or powdery resin being characterized by(A) containing spherical primary particles and secondary particles resulting from the agglomeration of the primary particles, each of said particles having a particle diameter of 0.1 to 100 microns,(B) having such a size that at least 50% by weight thereof can pass through a 150 Tyler mesh sieve,(C) having a free phenol content, determined by liquid chromatography, of not more than 50 ppm, and(D) having a D.sub.960-1020 /D.sub.1450-1500 ratio of from 0.1 to 2.0 in its infrared absorption spectrum.
    Type: Grant
    Filed: June 16, 1982
    Date of Patent: November 8, 1983
    Assignees: Kanebo Ltd., Mitsubishi Chemical Industries Limited
    Inventors: Hiroaki Koyama, Shigeo Shimizu
  • Patent number: 4414378
    Abstract: A granular or powdery resin which is a condensation product of a phenol and formaldehyde, said granular or powdery resin being characterized by(A) containing spherical primary particles and secondary particles resulting from the agglomeration of the primary particles, each of the particles having a particle diameter of 0.1 to 150 microns,(B) having such a size that at least 50% by weight thereof can pass through a 100 Tyler mesh sieve,(C) having a free phenol content, determined by liquid chromatography, of not more than 50 ppm,(D) having a D.sub.990-1015 /D.sub.1600 ratio of from 0.2 to 9.0 and a D.sub.890 /D.sub.1600 ratio of from 0.09 to 1.0 in its infrared absorption spectrum measured by a KBr tablet method, wherein D.sub.1600 represents the absorption intensity of an absorption peak at 1600 cm.sup.-1, D.sub.990-1015 represents the highest absorption intensity of absorption peaks at 990 to 1015 cm.sup.-1, and the D.sub.890 represents the absorption intensity of an absorption peak at 890 cm.sup.
    Type: Grant
    Filed: April 15, 1982
    Date of Patent: November 8, 1983
    Assignee: Mitsubishi Chemical Industries Limited
    Inventors: Hiroaki Koyama, Shigeo Shimizu
  • Patent number: 4413113
    Abstract: A process is disclosed whereby water-soluble phenol-formaldehyde resins are produced from molten phenol and particulate paraformaldehyde in the presence of an alkaline catalyst by reacting in a coil container at a temperature ranging from about 90.degree. C. to 120.degree. C. Apparatus for conducting the reaction and decorative laminates produced from the resultant resin are also disclosed.
    Type: Grant
    Filed: March 17, 1982
    Date of Patent: November 1, 1983
    Assignee: Formica Limited
    Inventors: Paul J. Gelling, James E. B. Hunt, John D. Marshman
  • Patent number: 4403076
    Abstract: A fast curing shell molding composition having the tensile strength of a conventional novolac resin when cured contains a fast curing novolac resin comprising a methylene chained polyphenylol wherein a major portion of the methylene linkages are coupled to adjacent phenylol groups at the o-o' and p-p' position, wherein at least about 19% of the methylene linkages are coupled to adjacent phenylol groups at the o-o' portions, and wherein at least about 3% of the total number of methylene linkages are coupled to adjacent phenylol groups at the p-p' positions. The shell molding composition is produced from the fast curing novolac resin by uniformly coating refractory granules with the fast curing resin. The fast curing novolac resin can be prepared by blending a conventional novolac resin with a novolac resin having a large proportion of methylene linkages coupled to adjacent phenylol groups at the o-o' position.
    Type: Grant
    Filed: March 5, 1982
    Date of Patent: September 6, 1983
    Assignee: Pacific Resins & Chemicals, Inc.
    Inventor: Roderick A. McDonald
  • Patent number: 4395535
    Abstract: A process for the manufacture of condensation products of phenols and isobutyraldehyde by reacting the phenols and isobutyraldehyde at elevated temperature in a mole ratio of 0.5:1 to 1.5:1 in the presence of acid or compounds hydrolyzable to acids as catalysts, subsequent neutralization and removal of the resultant reaction water by distillation wherein the reaction products obtained in this manner are also subjected to a water-vapor distillation.
    Type: Grant
    Filed: October 6, 1981
    Date of Patent: July 26, 1983
    Assignee: BASF Aktiengesellschaft
    Inventors: Juergen Nieberle, Karl-Clemens Peters, Wolfgang Reuther, Heinz-Hilmar Bankowsky
  • Patent number: 4366303
    Abstract: Particulate resoles are produced by mixing phenol, formaldehyde and amine in an aqueous medium containing a protective colloid. The resoles exhibit improved cure rate and sinter resistance when an alkaline compound is added to the reaction mixture after particulate formation.
    Type: Grant
    Filed: December 11, 1981
    Date of Patent: December 28, 1982
    Assignee: Union Carbide Corporation
    Inventor: Peter W. Kopf
  • Patent number: 4355141
    Abstract: In the polymerization of vinyl chloride, the adhesion of the resulting polymer to the walls can be prevented by previously applying a specific chemical to the inner walls of the polymerization tank and parts of the device to be contacted with the monomer during the polymerization. This specific chemical is a copolycondensate obtained by reacting a resol type phenol/formaldehyde precondensate with a nitrogen-containing compound selected from the group consisting of nitrophenols, nitrobenzoic acids, nitrobenzenesulfonic acids, aminophenols, aminobenzoic acids and aminobenzenesulfonic acids.
    Type: Grant
    Filed: May 20, 1981
    Date of Patent: October 19, 1982
    Assignee: Mitsui Toatsu Chemical, Inc.
    Inventors: Hiroshi Okada, Seiichi Masuko, Kuniyuki Gotoh, Takehiko Mogi
  • Patent number: 4350800
    Abstract: A process for the preparation of synthetic resins based on resorcinol compounds which comprises reacting a resorcinol pitch which is obtained in the manufacture of resorcinol from benzenedisulfonic acid in at least one step with an oxo-compound selected from aldehydes, ketones and compounds based on or splitting off at least one of these substances, and the use of the products as binders for abrasive articles.
    Type: Grant
    Filed: September 14, 1981
    Date of Patent: September 21, 1982
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Wolfgang Hesse, Franz Landauer, Klaus Schmiedel
  • Patent number: 4340700
    Abstract: A process for preparing a resin containing phenolic groups, in which an aralkylene ether of formula ROCH.sub.2.Ar. CH.sub.2 OR, wherein Ar represents a phenylene group and R is an alkyl group of 1-4 carbon atoms, is reacted with a phenol containing 1-3 hydroxyl groups and at least 2 hydrogen atoms in the aromatic phenolic nucleus, wherein (1) an ether composition which comprises at least 50 molar % e.g. 50-100% of said ether and the remainder of said composition, if any i.e. up to 50% (such as 0.1-50%) is selected from aromatic compounds each with an Ar nucleus having two substituents selected from CH.sub.3, CH.sub.2 OR, CHO, CH(OR).sub.2, said phenol and (2) an added compound of formula R'CHO or R'CH (OR.sup.2).sub.2, wherein R' is monovalent phenyl group or substituted phenyl group, in which each substituent is an alkyl group of 1-4 carbon atoms or a chlorine atom, and R.sup.
    Type: Grant
    Filed: August 19, 1981
    Date of Patent: July 20, 1982
    Assignee: Albright & Wilson Limited
    Inventor: Alfred G. Edwards