With Aldehyde Or Derivative Patents (Class 528/129)
  • Publication number: 20020007038
    Abstract: Improved anti-reflective coating compositions for use in integrated circuit manufacturing processes and methods of forming these compositions are provided. Broadly, the compositions are formed by heating a solution comprising a compound including specific compounds (e.g., alkoxy alkyl melamines, alkoxy alkyl benzoguanamines) under acidic conditions so as to polymerize the compounds and form polymers having an average molecular weight of at least about 1,000 Daltons. The monomers of the resulting polymers are joined to one another via linkage groups (e.g., —CH2—, —CH2—O—CH2—) which are bonded to nitrogen atoms on the respective monomers. The polymerized compound is mixed with a solvent and applied to a substrate surface after which it is baked to form an anti-reflective layer. The resulting layer has high k values, improved etch rates, and can be formulated for both conformal and planar applications.
    Type: Application
    Filed: May 30, 2001
    Publication date: January 17, 2002
    Inventors: Rama Puligadda, Runhui Huang
  • Patent number: 6316583
    Abstract: The specification discloses a method for the manufacture of a fluorescent polyphenolic product with high UV absorbance, its subsequent epoxidation as well as polyphenolic products and epoxidized derivatives and compositions thereof. The polyphenolic products are prepared by heating glyoxal at a temperature of about 80° C. to about 100° C. with a molar excess of a phenol in the presence of an acidic catalyst which is eliminated from the reaction mixture at a temperature below about 170° C. The total mole ratio of glyoxal to phenol charged to the reaction mixture is about 0.15 to 0.22 moles of glyoxal for each mole of phenol. The glyoxal is added continuously or by stepwise additions to the phenol so as to keep the aldehyde units in the reaction mixture to less than about 70% of the aldehyde units in the total quantity of glyoxal to be charged for making the polyphenol. Water is distilled stepwise or continuously from the reaction mixture.
    Type: Grant
    Filed: December 13, 2000
    Date of Patent: November 13, 2001
    Assignee: Borden Chemical, Inc.
    Inventor: Arthur H. Gerber
  • Patent number: 6307009
    Abstract: An aqueous binder composition suitable for use as a binder in making wool and board products including fiberglass insulation comprising a phenolic resole resin binder made from phenol and formaldehyde by using an excess amount of a basic catalyst.
    Type: Grant
    Filed: December 29, 1999
    Date of Patent: October 23, 2001
    Assignee: Owens Corning Fiberglas Technology, Inc.
    Inventor: Jianjun Li
  • Publication number: 20010029291
    Abstract: An aqueous binder composition suitable for use as a binder in making wool and board products including fiberglass insulation comprising a phenolic resole resin binder made from phenol and formaldehyde by using an excess amount of a basic catalyst.
    Type: Application
    Filed: December 29, 1999
    Publication date: October 11, 2001
    Inventor: JIANJUN LI
  • Patent number: 6268459
    Abstract: Method for preparing melamine from urea via a high-pressure process in which solid melamine is obtained by transferring the melamine melt coming from the reactor to a vessel where the melamine melt is cooled with an evaporating cooling medium. The melamine melt comes from the melamine reactor at a temperature between the melting point of melamine and 450° C. and is sprayed into a cooling vessel, via spraying means, and cooled by means of an evaporating cooling medium to form melamine powder. The cooling vessel has an ammonia environment with an increased ammonia pressure. The melamine melt is thereby converted into melamine powder having a temperature of between 200° C. and the solidification point of melamine. The melamine powder is then cooled to a temperature below 200° C. with the powder mechanically agitated and being cooled directly or indirectly, after which the ammonia pressure is released and, if necessary, the melamine powder is cooled further.
    Type: Grant
    Filed: November 22, 1999
    Date of Patent: July 31, 2001
    Assignee: DSM N.V.
    Inventors: Tjay T. Tjioe, Hubertus J. M. Slangen
  • Publication number: 20010004664
    Abstract: A novolak-type phenol resin with less unreacted phenol and a narrow molecular weight distribution is produced in high yield by reaction of a phenol with an aldehyde using an organophosphonic acid as a catalyst, while keeping a water concentration of reaction system at not more than 30% by weight and a reaction temperature at 110° C.-200° C.
    Type: Application
    Filed: December 13, 2000
    Publication date: June 21, 2001
    Inventors: Masakatsu Asami, Yoshikazu Kobayashi
  • Patent number: 6245882
    Abstract: Method for the manufacture of a phenolic resin emulsion and/or dispersion, wherein an aldehyde, a phenolic compound and an alkaline catalyst are allowed to react at a temperature of 40-100° C. until a desired degree of condensation is achieved, and the pH of the resin is adjusted to a value below 9 using an acid in the presence of a surface active agent or a mixture thereof at a temperature below 100° C. and a phenolic resin emulsion and/or dispersion is obtained providing a colorless or light-colored glue line or surface when cured.
    Type: Grant
    Filed: September 1, 1999
    Date of Patent: June 12, 2001
    Assignee: Neste Chemicals Oy
    Inventors: Leena Matilainen, Guomin Bian, Claude Ostiguy, Rick Cheng, Matti Satuli, Kari Leskinen, Kwok Tang
  • Patent number: 6245438
    Abstract: The preparation of phenol-formaldehyde and melamine-formaldehyde resin-based binders extended with a cyclic urea-formaldehyde prepolymer and to products prepared using the binders. More particularly, the invention relates to a cyclic urea prepolymer comprising urea, formaldehyde, and ammonia or a primary amine which, when added to a phenol-formaldehyde or melamine-formaldehyde based resin, results in a useful binder for the manufacturer numerous articles.
    Type: Grant
    Filed: June 22, 2000
    Date of Patent: June 12, 2001
    Assignee: Georgia-Pacific Resins, Inc.
    Inventors: F. C. Dupre, Millard E. Foucht, William P. Freese, Kurt D. Gabrielson, Benjamin D. Gapud, W. Hayes Ingram, Ted M. McVay, Richard A. Rediger, Kelly A. Shoemake, Kim K. Tutin, James T. Wright
  • Patent number: 6242533
    Abstract: The present invention relates to a novolak type phenol resin, in particular a novolak type phenol resin for resists suitable for forming resist patterns. The novolak type phenol resin of the present invention is obtained by reacting at least a vinylphenol having a vinyl group and a phenolic hydroxyl group, such as parahydroxystyrene, or a polyvinylphenol, which is a polymer of the vinylphenol, a compound (A) such as 4,4′-methylenebis(2-hydroxymethyl-3,6-dimethylphenol) and/or a compound (B) such as 2,6-dihydroxymethyl-4-phenol, in a ratio of 1 to 40 moles of the compound (A) and/or compound (B) to 100 moles of the vinylphenol or 100 moles of structural unit of the vinylphenol contained in the polyvinylphenol in the presence of an acid and having a weight average molecular weight of 2,000 to 20,000. Such a novolak type phenol resin provides good pattern shape, heat resistance, resolution, and sensitivity in resists for lithography.
    Type: Grant
    Filed: May 31, 2000
    Date of Patent: June 5, 2001
    Assignee: Gun Ei Chemical Industry Co., Ltd.
    Inventors: Yoshiaki Kurimoto, Katsuhiro Maruyama, Akira Yoshitomo, Satoru Yoshida, Satoru Kitano
  • Patent number: 6239248
    Abstract: The specification discloses a method for the manufacture of a fluorescent polyphenolic product with high UV absorbance, its subsequent epoxidation, polyphenolic products, epoxidized derivatives and compositions thereof as well as laminates containing fluorescent polyphenolic products and derivatives thereof. The polyphenolic products are prepared by heating glyoxal at a temperature of about 80° C. to about 100° C. with a molar excess of a phenol in the presence of an acidic catalyst which is eliminated from the reaction mixture at a temperature below about 170° C. The total mole ratio of glyoxal to phenol charged to the reaction mixture is about 0.15 to 0.22 moles of glyoxal for each mole of phenol. The glyoxal is added continuously or by stepwise additions to the phenol so as to keep the aldehyde units in the reaction mixture to less than about 70% of the aldehyde units in the total quantity of glyoxal to be charged for making the polyphenol.
    Type: Grant
    Filed: April 23, 1999
    Date of Patent: May 29, 2001
    Assignee: Borden Chemical, Inc.
    Inventor: Arthur H. Gerber
  • Patent number: 6232399
    Abstract: The specification discloses a method for the manufacture of a fluorescent polyphenolic product with high UV absorbance, its subsequent epoxidation as well as polyphenolic products and epoxidized derivatives and compositions thereof. The polyphenolic products are prepared by heating glyoxal at a temperature of about 80° C. to about 100° C. with a molar excess of a phenol in the presence of an acidic catalyst which is eliminated from the reaction mixture at a temperature below about 170° C. The total mole ratio of glyoxal to phenol charged to the reaction mixture is about 0.15 to 0.22 moles of glyoxal for each mole of phenol. The glyoxal is added continuously or by stepwise additions to the phenol so as to keep the aldehyde units in the reaction mixture to less than about 70% of the aldehyde units in the total quantity of glyoxal to be charged for making the polyphenol. Water is distilled stepwise or continuously from the reaction mixture.
    Type: Grant
    Filed: August 9, 2000
    Date of Patent: May 15, 2001
    Assignee: Borden Chemical, Inc.
    Inventor: Arthur H. Gerber
  • Patent number: 6214964
    Abstract: A process for forming a phenol formaldehyde resin, the process comprising the steps of: (i) reacting phenol with an excess of a formaldehyde material in the presence of an acid or base catalyst until water separates from the reactants as an immiscible layer; (ii) adding a mixture comprising an excess of polyhydric alcohol and an aromatic dicarboxylic or tricarboxylic acid, salt or anhydride thereof to the phenol and formaldehyde reaction mixture followed by addition of an alpha hydroxy acid; (iii) adding a non-aqueous solvent, wherein at least some of said water is removed either before addition of the mixture preparated in step (ii) or after addition of the alpha hydroxy acid; (iv) preparing a solution comprising a Lewis acid, a polyhydric alcohol, an alpha hydroxy acid, a non-aqueous solvent, an aromatic sulphonic acid and sulphuric or hydrochloric acid; (v) adding the solution formed in step (iv) to the mixture formed in step (ii) and allowing the mixture to cure.
    Type: Grant
    Filed: February 18, 2000
    Date of Patent: April 10, 2001
    Inventor: Barry William Ryan
  • Patent number: 6207789
    Abstract: The present invention provides a resin containing in the backbone chain a structural unit represented by the following Formula (I) or (II), as a novel phenolic resin having a high Tg, a low moisture absorption, a low molding shrinkage, high adhesive properties and high flow properties. The present invention also provides a resin composition and a molding material each containing the above resin, and an electronic component device having a device element encapsulated with it.
    Type: Grant
    Filed: February 23, 2000
    Date of Patent: March 27, 2001
    Assignee: Hitachi Chemical Co., Ltd.
    Inventors: Haruaki Sue, Shinsuke Hagiwara, Fumio Furusawa, Seiichi Akagi, Kazuyoshi Tendo
  • Patent number: 6201094
    Abstract: The specification discloses epoxidized products and compositions of a polyphenol of a phenol and glyoxal wherein the polyphenol prior to epoxidation has an ultraviolet (UV) absorbance of at lest 0.260 at 365 nanometers (nm) and/or at least 0.400 at 350 nm.
    Type: Grant
    Filed: October 20, 1999
    Date of Patent: March 13, 2001
    Assignee: Borden Chemical, Inc.
    Inventor: Arthur H. Gerber
  • Patent number: 6179885
    Abstract: This invention relates to a composition, comprising: (I) an aromatic Mannich compound derived from: (A) a hydroxy containing aromatic compound having the formula  wherein in Formula (A-1): Ar is an aromatic group; m is 1, 2 or 3; n is a number from 1 to about 4; with the proviso that the sum of m and n does not exceed the number of available positions on Ar that can be substituted; each R1 independently is a hydrocarbyl group of up to about 400 carbon atoms; and R2 is H, amino or carboxyl; (B) an aldehyde or ketone having the formula  or a precursor thereof; wherein in Formula (B-1): R1 and R2 independently are H or hydrocarbyl groups having from 1 to about 18 carbon atoms; and R2 can also be a carbonyl-containing hydrocarbyl group having from 1 to about 18 carbon atoms; and (C) a mixture of water and an amine, said amine containing at least one primary or secondary amino group; and (II) alcohol.
    Type: Grant
    Filed: June 22, 1999
    Date of Patent: January 30, 2001
    Assignee: The Lubrizol Corporation
    Inventor: Rodney John McAtee
  • Patent number: 6174986
    Abstract: A process for polymerizing a vinyl chloride monomer wherein the vinyl chloride monomer is subjected to homopolymerization or (co)polymerization with a monomer copolymerizable with the vinyl chloride monomer in an aqueous solvent, comprising applying in advance a coating liquid containing a cocondensation product obtained by reacting either a phenothiazine derivative and an aldehyde or a phenothiazine derivative, a naphthol derivative and an aldehyde to give an initial condensation product and then reacting the initial product with a polyphenol, to an inner wall of a polymerization tank and parts of an apparatus in contact with the monomers during the polymerization process. The process makes it possible to apply the cocondensation product as an aqueous solution to, e.g., an inner wall of a polymerization tank; to quite effectively prevent polymer adhesion in, e.g.
    Type: Grant
    Filed: December 18, 1997
    Date of Patent: January 16, 2001
    Assignee: Mitsui Chemicals, Inc.
    Inventors: Ichisaburo Nakamura, Akihiko Takahashi, Masaaki Ozawa
  • Patent number: 6166131
    Abstract: Disclosed is a process for producing a highly reactive modified phenolic resin, which comprises mixing a heavy oil or pitch with 0.3 to 10 mol of a phenol, 0.2 to 9 mol in terms of formaldehyde, of a formaldehyde compound and 0.01 to 3.0 mol of an acid catalyst, each amount being based on 1 mol of the heavy oil or pitch calculated from an average molecular weight; and heating the resulting mixture with stirring, thereby to polycondensate the heavy oil or pitch, phenol and formaldehyde compound. According to this invention, there can be provided a process for producing simply and stably a highly reactive modified phenolic resin having low melt viscosity, excellent heat resistance and high reactivity with an epoxy resin, in one step.
    Type: Grant
    Filed: September 22, 1999
    Date of Patent: December 26, 2000
    Assignee: Kashima Oil Co., Ltd.
    Inventors: Masao Tashima, Hiromi Miyasita, Haruhiko Takeda, Tomoaki Fujii, Tatsushi Ishizuka, Makoto Hasegawa
  • Patent number: 6160079
    Abstract: Arylamines with electron donating groups such as alkyl and alkoxy groups in the meta position on the aromatic ring change the polymerization temperature of the benzoxazine prepared therefrom and offer an opportunity for an additional crosslinking site (the para position on the aromatic amine can couple to a Mannich base generated by the opening of the oxazine ring of the benzoxazine or a methylene bridge generated by a degradation reaction). Naphthenic amines with an alkyl or alkoxy substituent on the 5.sup.th through the 8.sup.th carbon atom on the naphthalene ring can function similarly. The polymers for benzoxazines prepared from at least 10% substituted aromatic or naphthenic amines are useful due to low polymerization temperatures and higher Tg (glass transition temperature).
    Type: Grant
    Filed: April 14, 1999
    Date of Patent: December 12, 2000
    Assignee: Edison Polymer Innovation Corporation
    Inventors: Hatsuo Ishida, Daniel Sanders
  • Patent number: 6143856
    Abstract: A phenolic-rich pyrolysis oil is produced by pyrolysing lignocellulosic material at a temperature of no more than about 550.degree. C under an absolute pressure of no more than about 50 kPa to produce pyrolysis vapors, and condensing the pyrolysis vapors to obtain a condensate consisting of a phenolic-rich pyrolysis oil having a dew point of about 65 to about 75.degree. C. under an absolute pressure of about 15 to about 20 kPa. Such a phenolic-rich pyrolysis can be directly used in making phenol-formaldehyde resol resins.
    Type: Grant
    Filed: February 5, 1999
    Date of Patent: November 7, 2000
    Assignee: Pyrovac Technologies Inc.
    Inventors: Christian Roy, Xiao Lu, Hooshang Pakdel
  • Patent number: 6140421
    Abstract: The specification discloses a method for the manufacture of a fluorescent polyphenolic product with high UV absorbance, its subsequent epoxidation as well as polyphenolic products and epoxidized derivatives and compositions thereof. The polyphenolic products are prepared by heating glyoxal at a temperature of about 80.degree. C. to about 100.degree. C. with a molar excess of a phenol in the presence of an acidic catalyst which is eliminated from the reaction mixture at a temperature below about 170.degree. C. The total mole ratio of glyoxal to phenol charged to the reaction mixture is about 0.15 to 0.22 moles of glyoxal for each mole of phenol. The glyoxal is added continuously or by stepwise additions to the phenol so as to keep the aldehyde units in the reaction mixture to less than about 70% of the aldehyde units in the total quantity of glyoxal to be charged for making the polyphenol. Water is distilled stepwise or continuously from the reaction mixture.
    Type: Grant
    Filed: September 23, 1999
    Date of Patent: October 31, 2000
    Assignee: Borden Chemical, Inc.
    Inventor: Arthur Harry Gerber
  • Patent number: 6121412
    Abstract: The present invention provides a method for producing a film forming, fractionated novolak resin, by:a) condensing formaldehyde with one or more phenolic compounds, and thereby producing a novolak resin;b) adding a photoresist solvent, and optionally a water-soluble organic polar solvent;c) feeding the mixture into a liquid/liquid centrifuge and feeding a C.sub.5 -C.sub.8 alkane, water or aromatic hydrocarbon solvent into the liquid/liquid centrifuge at a ratio of optional water-soluble organic polar solvent and photoresist solvent to C.sub.5 -C.sub.8 alkane, water or aromatic solvent, of from 5:1 to 0.5:1;d) rotating the liquid/liquid centrifuge containing the mixture at a speed of at least 500 rpm and thereby separating the mixture into two phases, collecting the two phases;e) optionally separating the lighter phase (L) into two second phases;f) removing residual C.sub.5 -C.sub.
    Type: Grant
    Filed: October 14, 1999
    Date of Patent: September 19, 2000
    Assignee: Clariant Finance (BVI) Limited
    Inventors: Stanley F. Wanat, M. Dalil Rahman, John J. Kokoszka, Balaji Narasimhan
  • Patent number: 6114491
    Abstract: The preparation of phenol-formaldehyde and melamine-formaldehyde resin-based binders extended with a cyclic urea-formaldehyde prepolymer and to products prepared using the binders. More particularly, the invention relates to a cyclic urea prepolymer comprising urea, formaldehyde, and ammonia or a primary amine which, when added to a phenol-formaldehyde or melamine-formaldehyde based resin, results in a useful binder for the manufacturer numerous articles.
    Type: Grant
    Filed: December 17, 1998
    Date of Patent: September 5, 2000
    Assignee: Georgia-Pacific Resins, Inc.
    Inventors: F. C. Dupre, Millard E. Foucht, William P. Freese, Kurt D. Gabrielson, Benjamin D. Gapud, W. Hayes Ingram, Ted M. McVay, Richard A. Rediger, Kelly A. Shoemake, Kim K. Tutin, James T. Wright
  • Patent number: 6100364
    Abstract: A water-reducible binder for coatings comprises the reaction products of a) a phenolic resin comprising the reaction product of bisphenol A, t-butyl phenol and formaldehyde; b) an alkylene carbonate alkoxylating agent; c) a diol selected form the group consisting of 1,4-cyclohexanedimethanol, 3,5,5-trimethylpentane diol and neopentyl glycol; and d) trimellitic anhydride. Methods for preparing such a water-reducible binder and coating systems comprising such a binder are also disclosed.
    Type: Grant
    Filed: May 4, 1999
    Date of Patent: August 8, 2000
    Assignee: U.S. Polymers, Inc.
    Inventors: Robert J. Gaal, Jr., Roger W. Heitland
  • Patent number: 6087414
    Abstract: Disclosed is a process which comprises reacting a polymer of the general formula ##STR1## wherein x is an integer of 0 or 1, A is one of several specified groups, such as ##STR2## B is one of several specified groups, such as ##STR3##
    Type: Grant
    Filed: December 23, 1998
    Date of Patent: July 11, 2000
    Assignee: Xerox Corporation
    Inventors: Timothy J. Fuller, Ram S. Narang, Thomas W. Smith, David J. Luca, Raymond K. Crandall
  • Patent number: 6087467
    Abstract: Rigid-rod and segmented rigid-rod polymers, methods for preparing the polymers and useful articles incorporating the polymers are provided. The polymers incorporate rigid-rod backbones with pendant solubilizing groups attached thereto for rendering the polymers soluble.
    Type: Grant
    Filed: December 2, 1998
    Date of Patent: July 11, 2000
    Assignee: Maxdem Incorporated
    Inventors: Matthew Louis Marrocco, III, Robert R. Cagne, Mark Steven Trimmer
  • Patent number: 6046252
    Abstract: A binder composition of a phenolic novolac resin and a (lower) alkoxylated triazine-formaldehyde resin curing agent is disclosed. The triazine resins have sufficient carbon atoms in the alkoxy groups so as to provide a curing agent having a water solubility of less than 15%. The binder cures at high temperatures so as to provide improved flow and prolonged workability to the composition. The compositions are useful in refractory applications having a need for high temperature curing agents such as for maintenance and repair within refractory vessels by gunning/spraying, manufacture of electrodes by the Soderberg method, and for use in blast furnace tap holes.
    Type: Grant
    Filed: February 25, 1997
    Date of Patent: April 4, 2000
    Assignee: Borden Chemical, Inc.
    Inventor: Arthur H. Gerber
  • Patent number: 6034210
    Abstract: Disclosed is a process for producing a highly reactive modified phenolic resin, which comprises mixing a heavy oil or pitch with 0.3 to 10 mol of a phenol, 0.2 to 9 mol in terms of formaldehyde, of a formaldehyde compound and 0.01 to 3.0 mol of an acid catalyst, each amount being based on 1 mol of the heavy oil or pitch calculated from an average molecular weight; and heating the resulting mixture with stirring, thereby to polycondensate the heavy oil or pitch, phenol and formaldehyde compound. According to this invention, there can be provided a process for producing simply and stably a highly reactive modified phenolic resin having low melt viscosity, excellent heat resistance and high reactivity with an epoxy resin, in one step.
    Type: Grant
    Filed: February 17, 1998
    Date of Patent: March 7, 2000
    Assignee: Kashima Oil Co., Ltd.
    Inventors: Masao Tashima, Hiromi Miyasita, Haruhiko Takeda, Tomoaki Fujii, Tatsushi Ishizuka, Makoto Hasegawa
  • Patent number: 6031064
    Abstract: Condensation products obtained by condensation of(A) a mixture consisting of(a) a triazine of the general formula I ##STR1## and (b) a mixture consisting of(b1) a triazine of the general formula II ##STR2## (b2) a substituted melamine of the general formula III ##STR3## (B) phenols withformaldehyde or formaldehyde-donating compounds are useful for producing shaped articles, especially fibers and foams.
    Type: Grant
    Filed: August 28, 1998
    Date of Patent: February 29, 2000
    Assignee: BASF Aktiengesellschaft
    Inventors: Erhard Guenther, Wolfgang Reuther
  • Patent number: 6019867
    Abstract: Mixed glycols, as exist in the waste stream from a glycol production unit, are utilized for production of a liquid resole resin in an aqueous alcoholic solvent. The solvated resole resin is employed as a binder for production of laminates.
    Type: Grant
    Filed: November 27, 1996
    Date of Patent: February 1, 2000
    Assignee: Saudi Basic Industries Corporation
    Inventor: Mahmood Ahmad M. Saeed
  • Patent number: 6015863
    Abstract: Polymeric Mannich base condensates useful as fuel and lubricant additives. The polymeric Mannich base additives are the reaction products of poly (alpha-olefin/unsaturated acidic reactants) with Mannich base adducts of alkyl-substituted phenols condensed with aldehydes and amines.
    Type: Grant
    Filed: April 2, 1998
    Date of Patent: January 18, 2000
    Assignee: Ethyl Corporation
    Inventors: Carl Anthony Mike, Gregory Paul Anderson, Carl Kurt Esche, Jr.
  • Patent number: 6001950
    Abstract: The specification discloses a method for the manufacture of a fluorescent polyphenolic product with high UV absorbance, its subsequent epoxidation as well as polyphenolic products and epoxidized derivatives and compositions thereof. The polyphenolic products are prepared by heating glyoxal at a temperature of about 80.degree. C. to about 100.degree. C. with a molar excess of a phenol in the presence of an acidic catalyst which is eliminated from the reaction mixture at a temperature below about 170.degree. C. The total mole ratio of glyoxal to phenol charged to the reaction mixture is about 0.15 to 0.22 moles of glyoxal for each mole of phenol. The glyoxal is added continuously or by stepwise additions to the phenol so as to keep the aldehyde units in the reaction mixture to less than about 70% of the aldehyde units in the total quantity of glyoxal to be charged for making the polyphenol. Water is distilled stepwise or continuously from the reaction mixture.
    Type: Grant
    Filed: September 22, 1998
    Date of Patent: December 14, 1999
    Assignee: Borden Chemical, Inc.
    Inventor: Arthur Harry Gerber
  • Patent number: 6001949
    Abstract: One of the objects of the present invention is to offer novolak type phenolic resins which use phenols and aldehydes as raw materials and give narrow molecular weight distributions.The novolak type phenolic resins of the present invention are those obtained by condensation reaction of phenols with aldehydes in the presence of an oxycarboxylic acid having carboxyl groups, --COOH, and alcoholic hydroxyl groups, --OH, in one molecule. Thus obtained novolak type phenolic resins show narrow molecular weight distributions, lower viscosity in molten state and, as a consequence, uniformity in curing time.
    Type: Grant
    Filed: December 13, 1995
    Date of Patent: December 14, 1999
    Assignee: Gun Ei Chemical Industry Co., Ltd.
    Inventors: Yoshiaki Kurimoto, Akiyuki Kojima, Yukio Abe, Tsuyoshi Fukuda, Kaori Hasegawa
  • Patent number: 5986035
    Abstract: Provided is a high-molecular weight high-ortho novolak type phenolic resin excellent in handleability, heat resistance characteristics, curability and electric characteristics suitable for various uses and superior in balance of properties. This high-molecular weight high-ortho novolak type phenolic resin is a condensate of a trifunctional phenol compound with an aldehyde compound, is soluble in solvents, has a weight-average molecular weight of 50,000 or more calculated by polystyrene standard, has methylene bonds at ortho-ortho position in respect to phenolic hydroxyl group in an amount of 55% or more based on total methylene bonds, and has an extraction water electric conductivity of 10 .mu.S/cm or less.
    Type: Grant
    Filed: April 9, 1998
    Date of Patent: November 16, 1999
    Assignee: Sumitomo Bakelite Company Limited
    Inventors: Masayuki Inagaki, Shoji Tomita
  • Patent number: 5976761
    Abstract: A process for producing a water insoluble, aqueous alkali soluble, film forming novolak resin having low metal ions, made by the fractionation of a phenol formaldehyde condensation product, a process for producing a resin a photoresist composition of superior quality containing such novolak resin, and a method for producing a semiconductor device using such photoresist composition.
    Type: Grant
    Filed: March 25, 1998
    Date of Patent: November 2, 1999
    Assignee: Clariant Finance (BVI) Limited
    Inventors: M. Dalil Rahman, Daniel P. Aubin, Dinesh N. Khanna, Sunit S. Dixit
  • Patent number: 5977288
    Abstract: The present invention provides a method for producing a film forming, fractionated novolak resin having consistent molecular weight and superior performance in photoresist composition, by isolating such novolak resin fractions without high temperature distillation. A method is also provided for producing photoresist composition from such a fractionated novolak resin and for producing semiconductor devices using such a photoresist composition.
    Type: Grant
    Filed: August 4, 1998
    Date of Patent: November 2, 1999
    Assignee: Clariant Finance (BVI) Limited
    Inventors: M. Dalil Rahman, Ping-Hung Lu
  • Patent number: 5977287
    Abstract: There is provided a composition comprising tannin containing hydroxyl groups which has been (a) chemically modified by reaction of at least one of said hydroxyl groups with at least one member selected from the group consisting of an esterification agent (e.g. acetic anhydride), etherification agent (e.g. dichloromethane or quaternary organic amine such as N-(3-chloro-2-hydroxypropyl) trimethyl ammonium chloride) to form the corresponding ester, or ether, through said hydroxyl group, and (b) derivatized. The chemically modified tannin is derivatized by reaction with aldehyhde (e.g. formaldehyde), or aldehyde and at least one member selected from the group consisting of ammonia and organic amine containing at least one primary or secondary nitrogen (e.g. cyclohexyl amine); said derivatized tannin being water soluble or dispersable at a pH below 7 and water insoluble at a pH above 7.
    Type: Grant
    Filed: July 16, 1998
    Date of Patent: November 2, 1999
    Assignee: BetzDearborn Inc.
    Inventors: David Brian Mitchell, Ralph Lemmel Minnis, Thomas Peter Curran, Steven M Deboo, John Arthur Kelly, Rashmi Patwardhan, Wun Ten Tai
  • Patent number: 5939515
    Abstract: Condensation of products obtained by condensation of a mixture comprising(A) from 90 to 99.9 mol % of a mixture consisting essentially of(a) from 30 to 100 mol % of melamine and(b) from 0 to 70 mol % of a substituted melamine of the formula I ##STR1## where X, X' and X" are as defined in the specification, or mixtures of melamines I, and(c) from 1 to 70 mol %, based on (a)+(b), of a substituted triazine of the formula II ##STR2## where R", Z' and Z" are as defined in the specification, or mixtures of triazines II, and(B) from 0.1 to 10 mol %, based on (A) (a), (A) (b) and (B), of phenols which are unsubstituted or are substituted by radicals selected from the group consisting of C.sub.1 -C.sub.9 -alkyl and hydroxyl, C.sub.1 -C.sub.4 -alkanes substituted by two or three phenol groups, di(hydroxyphenyl)sulfones or mixtures of these phenols,withformaldehyde or formaldehyde-supplying compounds in a molar ratio of melamine, substituted melamine I and triazine II to formaldehyde within the range from 1:1.15 to 1:4.
    Type: Grant
    Filed: January 29, 1998
    Date of Patent: August 17, 1999
    Assignee: BASF Aktiengesellschaft
    Inventors: Erhard Guenther, Wolfgang Reuther
  • Patent number: 5939511
    Abstract: The invention is directed to purification of phenolic resins and to a process for preparing an organic photoresist coating composition. The process comprises reacting one or more phenols to form a crude phenolic resin. The crude phenolic resin formed is then separated from its reaction mixture and dissolved in an aqueous insoluble organic solvent in an organic solvent that is a solvent for the photoresist coating composition. The solution so formed is then mixed with an aqueous phase to extract water soluble impurities from the resin solution into the aqueous phase. Finally, the purified resin solution is further diluted with additional photoresist solvent.
    Type: Grant
    Filed: April 8, 1998
    Date of Patent: August 17, 1999
    Assignee: Shipley Company, L.L.C.
    Inventors: Anthony Zampini, Suzanne M. Coley
  • Patent number: 5929191
    Abstract: One of the objects of the present invention is to offer novolak type phenolic resins which use phenols and aldehydes as raw materials and give narrow molecular weight distributions.The novolak type phenolic resins of the present invention are those obtained by condensation reaction of phenols with aldehydes in the presence of an oxycarboxylic acid having carboxyl groups, --COOH, and alcoholic hydroxyl groups, --OH, in one molecule. Thus, obtained novolak type phenolic resins show narrow molecular weight distributions, lower viscosity in molten state and, as a consequence, uniformity in curing time.
    Type: Grant
    Filed: May 27, 1997
    Date of Patent: July 27, 1999
    Assignee: Gun Ei Chemical Industry Co., Ltd.
    Inventors: Yoshiaki Kurimoto, Akiyuki Kojima, Yukio Abe, Tsuyoshi Fukuda, Kaori Hasegawa
  • Patent number: 5919873
    Abstract: Disclosed are novel crosslinked polymers derived from methylol phenols and maleic acid species, and methods of synthesizing these macromolecules. Polyesters and chromandicarboxylic groups are the dominant linkages in the structure of general formula: ##STR1## R is H or a spacing group between aromatics, R.sub.1 is an aldehyde substituent, R.sub.2 a spacing group belonging to multihidric alcohols, a maleyl grouping, and n a whole number either 0 or 1.
    Type: Grant
    Filed: July 24, 1998
    Date of Patent: July 6, 1999
    Assignee: Rio Oeste, S.A.
    Inventor: Nicholas M. Irving
  • Patent number: 5912317
    Abstract: An improved oxazolidine-based hardener to be used with a resorcinol resin or a tannin resin as the adhesive for the bonding of wood articles. Preferably, an oxazolidine is combined with particulate silica, and the resin is combined with a base such as NaOH. The adhesive based on the improved hardener can be used to glue wood particles to pass wet strength requirements after the glue is cured at room temperature for under 24 hours. The improved hardener composition is storage stable; it can be prepared anytime before its use and, thus, eliminate the need to prepare a hardener immediately prior to the glue use. Since it is formaldehyde-free; it eliminates the safety issues associated with handling formaldehyde or paraformaldehyde. Also, the hardener provides flexible gel time or working time. Since the resins can be cured at room temperature, heating in an oven is not needed but could be used to reduce curing time. If radio frequencies are used to cure the resins, the exposure time can be reduced.
    Type: Grant
    Filed: August 15, 1997
    Date of Patent: June 15, 1999
    Assignee: ANGUS Chemical Company
    Inventor: Gaoming Wu
  • Patent number: 5908914
    Abstract: This invention relates to benzylic ether phenolic resole resins prepared in a sealed reaction vessel and their uses. The benzylic ether phenolic resole resins are prepared by heating phenol and an aldehyde in a sealed reaction vessel in the presence of a divalent metal catalyst without removing water generated by the reaction until an appropriate endpoint for the resin is reached. The benzylic ether phenolic resole resins produced by the process are preferably free or essentially free of unreacted formaldehyde and can be used in the resin component of phenolic-urethane foundry binders to make foundry cores and/or molds by the cold-box and no-bake processes. The cores and/or molds are used for making metal castings.
    Type: Grant
    Filed: July 17, 1996
    Date of Patent: June 1, 1999
    Assignee: Ashland Inc.
    Inventors: Thomas Edward Dando, William Rexford Dunnavant, Robert Bernard Fechter, Heimo Josef Langer
  • Patent number: 5900472
    Abstract: Copolymerizable benzophenone photoinitiators of the formula I ##STR1## wherein 1, k=0, 1, 2.R.sub.1 =divalent organic group having 1 to 25 carbon atoms;R.sub.2 =H or methyl; andR.sub.3, R.sub.4 =organic group having 1 to 25 carbon atoms.X, Y=hydrogen, halogen or (C.sub.1 -C.sub.25) groups containing N, S, and/or O;and method of making the photoinitiators.The photoinitiators overcome the leaching problem with prior photoinitiators in radiation curable polymer applications. Radiation curable polymers, cured polymers, and coated articles are also disclosed.
    Type: Grant
    Filed: December 23, 1996
    Date of Patent: May 4, 1999
    Assignee: Sartomer Technology
    Inventors: Mingxin Fan, Gary W. Ceska, James Horgan
  • Patent number: 5866669
    Abstract: A method for the improvement of yield and freeness which does not discolor the paper product and gives a long life to the product and exerts stable yield improving effect even for the paper stuff containing much deinked pulp and filler as well as a yield improving promotor used in this method are provided.In the method for the improvement of yield and freeness in the paper-making process and the waste water treating process according to the present invention, a special phenol resin is used in combination with polyethylene oxide (PEO). The phenol resin of the present invention is a sulfonated phenol-formaldehyde resin synthesized by sulfonating a phenol and then condensing it with formaldehyde. Preferred as the phenol to be sulfonated are Bisphenol A and Bisphenol S.By using the method of the present invention, the yields of fine fiber and filler can be improved and the paper stuffs can be saved and the waste water treating load can be decreased.
    Type: Grant
    Filed: May 29, 1997
    Date of Patent: February 2, 1999
    Assignee: Meisel Chemical Works, Ltd.
    Inventors: Hisao Takatsu, Seika Tay, Mitsuyoshi Kato, Masafumi Yoshikawa
  • Patent number: 5859169
    Abstract: Urethane-modified novolaks which are prepared by simultaneous reaction of a monohydric or polyhydric phenol (A) with an oxo compound (aldehyde or ketone) (B) and a urethane (C) in the presence of an acidic catalyst (D) at an elevated temperature of 60.degree. to 200.degree. C. and contain no interfering amounts of free starting phenol, and their use as adhesion improvers in rubbers, in particular rubbers containing reinforcing media such as steel cord or textile fibers.
    Type: Grant
    Filed: September 8, 1997
    Date of Patent: January 12, 1999
    Assignee: Vianora Resins GmbH
    Inventors: Thomas Burkhart, Siegfried Wallenwein, Gerhard Brindoepke, Gerd Walz
  • Patent number: 5859168
    Abstract: One of the objects of the present invention is to offer novolak type phenolic resins which use phenols and aldehydes as raw materials and give narrow molecular weight distributions.The novolak type phenolic resins of the present invention are those obtained by condensation reaction of phenols with aldehydes in the presence of an oxycarboxylic acid having carboxyl groups, --COOH, and alcoholic hydroxyl groups, --OH, in one molecule. Thus obtained novolak type phenolic resins show narrow molecular weight distributions, lower viscosity in molten state and, as a consequence, uniformity in curing time.
    Type: Grant
    Filed: November 22, 1996
    Date of Patent: January 12, 1999
    Assignee: Gun Ei Chemical Industry Co., Ltd.
    Inventors: Yoshiaki Kurimoto, Akiyuki Kojima, Yukio Abe, Tsuyoshi Fukuda, Kaori Hasegawa
  • Patent number: 5849808
    Abstract: A polymer which is insoluble in aqueous-alkaline developer solutions, and comprises structural units of the formula (I): ##STR1## in which R.sub.2 is hydrogen, C.sub.1 -C.sub.18 alkyl, C.sub.5 -C.sub.10 cycloalkyl, C.sub.5 -C.sub.14 aryl, C.sub.6 -C.sub.30 aralkyl, R.sub.3 is C.sub.1 -C.sub.18 alkyl, C.sub.5 -C.sub.10 cycloalkyl, C.sub.5 -C.sub.14 aryl, or C.sub.6 -C.sub.30 aralkyl, it being possible for the alkyl, cycloalkyl, aryl, or aralkyl groups to be substituted if desired by one or more hydroxyl groups or nitro groups or by one or more halogen atoms, and X is a k+1 valent organic radical, k being a number from 1 to 5, and 1 is a number from 0 to 4, in a quantity such that the cleavage products obtained by reaction with an acid are soluble in aqueous-alkaline developer solutions, is suitable as a binder for DUV photoresists of high processing stability, high contrast, and good resolution.
    Type: Grant
    Filed: April 19, 1996
    Date of Patent: December 15, 1998
    Assignee: Olin Microelectronic Chemicals, Inc.
    Inventors: Hans-Thomas Schacht, Norbert Muenzel
  • Patent number: 5847190
    Abstract: The present invention relates to dendritic, nitrogen-containing organic compounds containing at least 4 planar-chiral or axial-chiral groups, where these planar-chiral or axial-chiral groups are linked as Schiff's bases to the primary amino groups of compounds of the formula (I)(R.sup.1 R.sup.1)N--X--N(R.sup.1 R.sup.1) (I)whereR.sup.1 is (R.sup.2 R.sup.2)N--(CH.sub.2).sub.2 -- or (R.sup.2 R.sup.2)N--(CH.sub.2).sub.3 --,R.sup.2 is hydrogen or (R.sup.3 R.sup.3)N--CH.sub.2).sub.2 -- or (R.sup.3 R.sup.3)N--(CH.sub.2).sub.3 --,R.sup.3 is hydrogen or (R.sup.4 R.sup.4)N--(CH.sub.2).sub.2 -- or (R.sup.4 R.sup.4)N--(CH.sub.2).sub.3 --,R.sup.4 is hydrogen or (R.sup.5 R.sup.5)--N--(CH.sub.2).sub.2 -- or (R.sup.5 R.sup.5)N--(CH.sub.2).sub.3 --,R.sup.5 is hydrogen or (R.sup.6 R.sup.6)N--(CH.sub.2).sub.2 -- or (R.sup.6 R.sup.6)N--(CH.sub.2).sub.3 -- andR.sup.6 is hydrogen,X is an aliphatic and/or aromatic group, which may contain heteroatoms,which are suitable as catalysts for asymmetrical homogeneous catalysis.
    Type: Grant
    Filed: May 20, 1997
    Date of Patent: December 8, 1998
    Assignee: BASF Aktiengesellschaft
    Inventors: Wolfgang Paulus, Fritz Vogtle, Jorg Issberner
  • Patent number: 5847058
    Abstract: A process for the production of a storage-stable, modified phenol-aldehyde resol resin includes the use of an alkylresorcinol modifier and preferably a readily-available mixture of alkylresorcinols. A binder system includes the modified phenol-aldehyde resin combined with a curing agent that includes an additional source of an aldehyde, e.g., a phenol-formaldehyde resin. The resin and binder system are useful in the production of a wood composite (such as plywood, oriented strandboard, or fiberboard).
    Type: Grant
    Filed: April 5, 1996
    Date of Patent: December 8, 1998
    Assignee: Masonite Corporation
    Inventor: Zygmunt Teodorczyk
  • Patent number: 5834088
    Abstract: A polyamide fibrous substrate having deposited on it an amount of a composition effective to impart stain-resistance comprising a water-soluble or water-dispersible alpha-olefin/maleic anhydride polymer or a mixture of said polymers, and processes for preparing the substrates. The maleic anhydride polymer is used either in hydrolyzed form or in the form resulting from reacting it with a lower alkyl alcohol so as to form an alpha-olefin/maleic acid monalkyl ester polymer.
    Type: Grant
    Filed: September 16, 1997
    Date of Patent: November 10, 1998
    Assignee: E. I. du Pont de Nemours and Company
    Inventor: Engelbert Pechhold