Additional Phenol-aldehyde- Or -aldehyde-type Polymer, Condensation Product Or Reactants Therefrom Patents (Class 525/501)
  • Patent number: 8623585
    Abstract: Provided is a positive photoresist composition containing, as an essential component, a novolac phenolic resin (C) prepared by condensing an aromatic compound (A) represented by general formula (1) or (2) with an aliphatic aldehyde (B). This positive photoresist composition has high sensitivity and high heat resistance at the same time, and is suitable for use as a positive photoresist in, for example, the manufacture of semiconductor devices such as ICs and LSIs, the manufacture of displays such as LCDs, and the manufacture of printing plates. (In the formulas, R1, R2, and R3 are each independently an alkyl group having 1 to 8 carbon atoms; m, n, and p are each independently an integer of 0 to 4; q is an integer of 1 to (5?p); and s is an integer of 1 to (9?p).
    Type: Grant
    Filed: October 25, 2011
    Date of Patent: January 7, 2014
    Assignee: DIC Corporation
    Inventors: Tomoyuki Imada, Takakazu Kage, Norifumi Imaizumi
  • Publication number: 20130131215
    Abstract: There are provided a phenol resin which produces a cured product having excellent heat resistance and a low coefficient of thermal expansion, a curable resin composition containing the phenol resin as a curing agent for an epoxy resin, a cured product of the curable resin composition, and a printed circuit board having excellent heat resistance and low thermal expansibility. A novel phenol resin having a resin structure which is formed by oxidizing a polycondensate (a) of a naphthol compound and formaldehyde and in which a naphthol skeleton (n) and a naphthoquinone skeleton (q) are bonded through a methylene bond is used as a curing agent for an epoxy resin.
    Type: Application
    Filed: July 19, 2011
    Publication date: May 23, 2013
    Applicant: DIC CORPORATION
    Inventor: Yutaka Satou
  • Publication number: 20120308832
    Abstract: A phenol resin composition used as a curing agent for an epoxy resin includes a naphthol novolac resin (a1) represented by general formula (1) (wherein R1 and R2 each independently represent a hydrogen atom, an alkyl group, or an alkoxy group, and n is a repeating unit and an integer of 1 or more), and a compound (a2) represented by general formula (2) (wherein R1 and R2 each independently represent a hydrogen atom, an alkyl group, or an alkoxy group), wherein the total ratio of compounds with n=1 and n=2 in the general formula (1) present in the composition is in the range of 10 to 35%, the average of n in the general formula (1) is in the range of 3.0 to 7.0, and the content of the compound (a2) in the composition is 1 to 6%.
    Type: Application
    Filed: January 19, 2011
    Publication date: December 6, 2012
    Applicant: DIC Corporation
    Inventors: Yutaka Satou, Kazuo Arita, Ichirou Ogura
  • Patent number: 8211987
    Abstract: The present invention relates to a method for reducing residual volatiles from polymer compositions.
    Type: Grant
    Filed: April 12, 2011
    Date of Patent: July 3, 2012
    Assignee: BASF SE
    Inventors: Fatemeh Ahmadnian, Wolfgang Loth, Karl-Heinz Wassmer, Andreas Brodhagen, Gerd Konrad
  • Publication number: 20120041146
    Abstract: The present invention provides methods to functionalize and solubilize WCNT with a phenolic polymer such as a lignin or a PF resin followed by in-situ integration of this functionalized CNT in the presence of formaldehyde and phenol and/or lignin to generate either CNT-reinforced phenol-formaldehyde polymer or CNT-reinforced lignin-phenol-formaldehyde polymer in either liquid or powder form suitable as an adhesive in the manufacture of a lignocellulosic composite material such as OSB and plywood.
    Type: Application
    Filed: July 27, 2011
    Publication date: February 16, 2012
    Applicants: NATIONAL RESEARCH COUNCIL OF CANADA, FPINNOVATIONS
    Inventors: Yaolin ZHANG, Xiang-Ming WANG, Martin FENG, Gilles BRUNETTE, Fuyong CHENG, Benoit SIMARD
  • Patent number: 7541410
    Abstract: A thermosetting resin composition comprising a novolac-type phenolic resin, a polyacetal resin and a cyclohexyl compound represented by the general formula (1) as a curing catalyst, a thermosetting resin molding compound comprising the thermosetting resin composition and a filler, and a cured product formed by curing the thermosetting resin composition or the thermosetting resin molding compound are provided. In the formula, R1 to R12 are defined in the claims and description.
    Type: Grant
    Filed: September 30, 2005
    Date of Patent: June 2, 2009
    Assignee: Sumitomo Bakelite Co., Ltd.
    Inventors: Masayasu Horie, Yukio Tokunaga, Shigeyoshi Furuhara
  • Patent number: 7442741
    Abstract: Storage stable aqueous dispersions of a heat-reactive hydrophilic phenolic resin (e.g., phenol/formaldehyde) are disclosed. The dispersions comprise a base resin that is the reaction product of an aromatic alcohol and an aldehyde, and an etherified resin component selected from the group consisting of an etherified phenol/aldehyde resin, an etherified cresol/aldehyde resin, and mixtures thereof. The dispersions further comprise a protective colloid (e.g., polyvinyl alcohol). The addition of the etherified resin component in an amount of at least about 20% by weight of the base resin provides storage stability, but does not adversely affect the desirable physical and chemical characteristics (e.g., chemical resistance) of end products made from such dispersions. Moreover, the dispersions of the present invention can avoid the use of etherified resin components derived from bisphenol-A and/or xylenols, which present heath concerns in food coating applications.
    Type: Grant
    Filed: April 11, 2005
    Date of Patent: October 28, 2008
    Assignee: Georgia-Pacific Chemicals LLC
    Inventors: Peter C. Boyer, Jeffrey L. Mills
  • Publication number: 20080248211
    Abstract: A method for producing film-forming materials including resins and/or crosslinkers having a —Si(OR)3 group. Methods of producing coating compositions and coating a substrate, such as a metal substrate, by electrodeposition. Applied coatings containing the film-forming materials can be cured to form crosslinked films on substrates.
    Type: Application
    Filed: March 13, 2007
    Publication date: October 9, 2008
    Applicant: BASF CORPORATION
    Inventors: Sergio Gonzalez, Timothy S. December
  • Patent number: 7381788
    Abstract: Provided is a continuous production method of a polyamide with stabilized polymerization degree and good quality, particularly an aromatic-containing polyamide.
    Type: Grant
    Filed: August 27, 2003
    Date of Patent: June 3, 2008
    Assignee: Toyo Boseki Kabushiki Kaisha
    Inventors: Yasuhito Tsujii, Gaku Maruyama, Kaoru Ogawa, Yoshinori Takada, Kazuhisa Koishi, Kenta Susuki
  • Patent number: 7001560
    Abstract: The present invention provides a resin composition suitable for molding a microscopic structure that has small cure shrinkage, good mold transfer properties and excellent properties for post-processing such as polishing processing and laser processing. Such a resin is a thermosetting resin composition comprising 95 to 35 wt % of a thermosetting resin and 5 to 65 wt % of organic filler having a particle size of 10 ?m or less. From such a resin, an ink ejecting apparatus having a microscopic structure, for example, a nozzle of a diameter of 30 ?m, is integrally molded.
    Type: Grant
    Filed: July 2, 2001
    Date of Patent: February 21, 2006
    Assignee: Cluster Technology Co., Ltd.
    Inventors: Minoru Adachi, Shoji Uesugi
  • Patent number: 6734275
    Abstract: The present invention relates to a method of gluing wood based materials by providing an adhesive system onto wood based materials followed by curing, the adhesive system comprises a urea based amino resin and a hardener composition, wherein the hardener composition comprises an acid and a phenolic resin. The invention also relates to an adhesive system and a hardener composition as well as wood based products obtained by the method or through the use of the adhesive system.
    Type: Grant
    Filed: October 18, 2002
    Date of Patent: May 11, 2004
    Assignee: Akzo Nobel N.V.
    Inventors: Salme Pirhonen, Benyahia Nasli-Bakir, Ingvar Lindh
  • Patent number: 6733949
    Abstract: Disclosed is an alkali-soluble, film-forming novolak resin mixture containing at least two novolak resins, each novolak resin containing the addition-condensation reaction product of at least one phenolic compound with at least one aldehyde source, wherein the phenolic compound for first novolak resin contains 90-100 mole % of meta-cresol, and the phenolic compound for the second novolak resin contains less than 50 mole % of meta-cresol. Also disclosed is a photosensitive composition, containing an admixture of: a) the above-mentioned novolak resin mixture; b) at least one o-quinone photoactive compound; and c) at least one photoresist solvent.
    Type: Grant
    Filed: April 11, 2002
    Date of Patent: May 11, 2004
    Assignee: Clariant Finance (BVI) Limited
    Inventors: J. Neville Eilbeck, Alberto D. Dioses
  • Patent number: 6667078
    Abstract: An epoxy resin composition having a viscosity of from 50 to 400 P at 25° C. is disclosed. The composition provides by casting a resin plate, particularly a transparent resin plate for a liquid crystal display, which has satisfactory thickness precision.
    Type: Grant
    Filed: April 10, 2002
    Date of Patent: December 23, 2003
    Assignee: Nitto Denko Corporation
    Inventors: Katsumi Shimada, Yutaka Aoki
  • Publication number: 20030207195
    Abstract: Disclosed is an alkali-soluble, film-forming novolak resin mixture containing at least two novolak resins, each novolak resin containing the addition-condensation reaction product of at least one phenolic compound with at least one aldehyde source, wherein the phenolic compound for first novolak resin contains 90-100 mole % of meta-cresol, and the phenolic compound for the second novolak resin contains less than 50 mole % of meta-cresol. Also disclosed is a photosensitive composition, containing an admixture of: a) the above-mentioned novolak resin mixture; b) at least one o-quinone photoactive compound; and c) at least one photoresist solvent.
    Type: Application
    Filed: April 11, 2002
    Publication date: November 6, 2003
    Inventors: J. Neville Eilbeck, Alberto D. Dioses
  • Publication number: 20030104215
    Abstract: An aqueous dispersion of a polymer synthesized from free-radical polymerizable compounds (monomers), wherein the dispersed polymer particles comprise compounds containing carbodiimide groups (carbodiimides for short) and the carbodiimides are not attached to the polymer by free-radical copolymerization.
    Type: Application
    Filed: June 17, 2002
    Publication date: June 5, 2003
    Inventors: Ulrike Licht, Karl Haberle, Christian Lach, Sabine Kielhorn-Bayer, Karl-Heinz Schumacher
  • Patent number: 6437057
    Abstract: Blends of novolaks and cyanates, such blends can be thermally hardened in a short time and without using a catalyst and have an excellent storage stability. The resins obtained by the blends can be used as binding agents in abradants or as chip coverings or printed circuit boards (PCB) in electronics.
    Type: Grant
    Filed: August 10, 2001
    Date of Patent: August 20, 2002
    Assignee: Lonza AG
    Inventors: Ulrich Daum, Alessandro Falchetto
  • Patent number: 6407183
    Abstract: An epoxy resin composition having a viscosity of from 50 to 400 P at 25° C. is disclosed. The composition provides by casting a resin plate, particularly a transparent resin plate for a liquid crystal display, which has satisfactory thickness precision.
    Type: Grant
    Filed: August 15, 2000
    Date of Patent: June 18, 2002
    Assignee: Nitto Denko Corporation
    Inventors: Katsumi Shimada, Yutaka Aoki
  • Patent number: 6232398
    Abstract: A resin matrix with resistances to alkali and acid such as a fluorene-containing epoxy acrylate and/or a benzocyclobutene resin includes at least any one of insulative organic particles and insulative composite particles having an organic component and an inorganic component with the total amount of these particles being in the range of 5-50% by volume, wherein the insulative organic particles and the organic component of the insulative composite particles are allowed to be corroded by either alkali or acid, and wherein not less than 90% by volume of the insulative organic particles and insulative composite particles have a particle diameter in the range of 1-20 micrometers.
    Type: Grant
    Filed: December 5, 1997
    Date of Patent: May 15, 2001
    Assignee: NEC Corporation
    Inventors: Yoshitsugu Funada, Koji Matsui
  • Patent number: 6165618
    Abstract: Curable coating compositions are described comprising(a) a polymer resin comprising carbamate functional groups,(b) a curing agent having groups that are reactive with said functional groups on (a), and(c) a compound having a molecular weight of from 75 to 2000 comprising at least one group of the formula: ##STR1## wherein X is O or NH, R is H or alkyl of 1 to 4 carbon atoms, and either (a), (b), or both (a) and (b) comprise groups that are reactive with said group on (c).
    Type: Grant
    Filed: November 3, 1994
    Date of Patent: December 26, 2000
    Assignee: BASF Corporation
    Inventors: Walter H. Ohrbom, Gregory G. Menovcik, John W. Rehfuss, Robert J. Taylor
  • Patent number: 6159405
    Abstract: A fire resistant phenolic resole-resorcinol novolac system for a pultrusion process, having a much improved pot life of the two part mixture, lower emissions during processing and a much better surface finish of the pultruded composite when compared to a similar existing system. A method of making a phenolic resole for pultrusion including, but not limited to, the use of modified phenols such as p-phenyl phenol and nonyl phenol.
    Type: Grant
    Filed: April 29, 1999
    Date of Patent: December 12, 2000
    Assignee: Borden Chemical, Inc.
    Inventor: John G. Taylor
  • Patent number: 6001483
    Abstract: A composition useful as an encapsulating material for photosemiconductor elements such as a photodetector or light emmitor comprises an epoxy resin, a hardener and at least one compound represented by the following general formula (1) or (2):CH.sub.3 CH.sub.2 --(--CH.sub.2 --CH.sub.2 --).sub.x --CH.sub.2 --CH.sub.2 --O--(--CH.sub.2 --CH.sub.2 --O--).sub.n --Y.sub.1 (1)[CH.sub.3 CH.sub.2 --(--CH.sub.2 --CH.sub.2 --).sub.x --CH.sub.2 --CH.sub.2 --O--(--CH.sub.2 --CH.sub.2 --O--).sub.n --RCOO--].sub.m --Y.sub.2(2)wherein Y.sub.1 represents --H, --RCOOH, --COR' or --R'; R' is an alkyl group with not more than 30 carbon atoms; R is a divalent organic group; Y.sub.2 represents a metal atom having a valence of at least one; the mean value for x is from 8-200; and n is set such that the weight ratio of the repeating unit --CH.sub.2 --CH.sub.2 --O-- accounts for from 25-95% by weight based on the whole compound; and m is a positive integer corresponding to the valence of Y.sub.2.
    Type: Grant
    Filed: September 23, 1996
    Date of Patent: December 14, 1999
    Assignee: Nitto Denko Corporation
    Inventors: Tadaaki Harada, Shinjirou Uenishi, Hirokatsu Kouyama, Takahiko Maruhashi, Katsumi Shimada, Satoshi Tanigawa
  • Patent number: 5944938
    Abstract: The invention is a method of gluing wood using a reactive two component thermosetting adhesive such as a phenol-resorcinol-formaldehyde (PRF) condensation product. One component is first coated on one of the members to be bonded. The second component is then spread directly on top of the first in a manner to minimize mixing; e.g., by spraying. When the mating member to be bonded is placed against the adhesive coated first member and pressure is applied the components are mixed. This begins the curing reaction between the components so that a thermosetting adhesive bond is formed. With selected adhesives very rapid curing times are possible. A preferred adhesive has a first component comprising a PRF resin mixed with a methylene group donor hardener such as paraformaldehyde. The second part is also a PRF resin. No hardener is present in the second part. Instead an oxygen and nitrogen containing heterocycle is used as an accelerator. Morpholine is a preferred compound.
    Type: Grant
    Filed: December 17, 1996
    Date of Patent: August 31, 1999
    Assignee: Weyerhaeuser Company
    Inventors: Jack G. Winterowd, Gerald N. MacPherson
  • Patent number: 5648435
    Abstract: A process of preparing multicyanate esters by: a) reacting an adduct of a tertiary amine and a phenol-formaldehyde oligomer or derivative thereof with cyanogen halide in a solvent reaction medium under conditions to form a reaction product stream containing at least one of the following compounds selected from the group consisting of tertiary amine-hydrohalide salt, solvent, and impurities, and, based upon the total weight of the reaction product stream excluding the weight of said tertiary amine-hydrohalide salt, from about 10 percent to about 40 percent of a multicyanate ester; b) recycling a portion of said reaction product stream into the mixture of step a; and c) separating and recovering said solvent and tertiary amine from said reaction product stream. The multicyanate ester products produced are useful as bonding agents in friction materials, molding materials, coatings, and adhesives.
    Type: Grant
    Filed: November 17, 1995
    Date of Patent: July 15, 1997
    Assignee: AlliedSignal Inc.
    Inventors: David W. H. Roth, Jr., Sajal Das
  • Patent number: 5646218
    Abstract: The present invention relates to a water insoluble, aqueous alkali soluble novolak resin blend, wherein the resin blend comprises two novolaks having dissimilar relative molecular weights and similar dissolution rates, a process for producing such a resin blend, a photoresist containing such a resin blend and a method for producing a semi-conductor device utilizing such a photoresist.
    Type: Grant
    Filed: August 5, 1996
    Date of Patent: July 8, 1997
    Assignee: Hoechst-Celanese Corp.
    Inventors: Thomas J. Lynch, Chester J. Sobodacha, Dana L. Durham
  • Patent number: 5626705
    Abstract: A rapid curing adhesive for wood finger jointing and laminating and a method of its use are disclosed. The adhesive consists of two parts that are used as a honeymoon system. One part is used on one side of the joint being formed and the other part on the other side. When the parts are joined under pressure a very rapid reaction occurs resulting in a durable weather resistant joint. Wood finger joints bonded with the adhesive can be handled for further processing within as little time as 15 seconds. The first part of the adhesive is a conventional resorcinol-formaldehyde or phenol-resorcinol formaldehyde resin containing a hardener such as an alkylene group donor. The second part is a similar resin lacking any hardener but containing a modifier which is a heterocyclic oxygen and nitrogen containing compound. Morpholine has proved to serve well as the modifier. The hardener in the first part is used in a sufficient amount to effect a thermosetting cure for the resin used in both parts.
    Type: Grant
    Filed: June 7, 1995
    Date of Patent: May 6, 1997
    Assignee: Weyerhaeuser Company
    Inventors: Jack G. Winterowd, Harvey H. Cox, Roland E. Kreibich, Stanley L. Floyd, Hans Gross
  • Patent number: 5525684
    Abstract: A phenolic resin composition comprises a mixture of 100 parts by weight of a phenol aralkyl resin and 5 to 60 parts by weight of a novolak type phenolic resin having a content of binuclear components of not more than 10% by area, and a content of trinuclear components of not less than 50% by area and a sum content of tri- and tetra-nuclear components of 75% by area based on the total novolak phenolic resin except for the binuclear components, and an epoxy-cured product obtained by curing an epoxy resin while using the phenolic resin composition as set forth in claim 1 as a curing agent. The phenolic resin composition has a low viscosity and, when it is used as a curing agent for epoxy resins, the resulting epoxy-cured product has a low water absorption rate, is excellent in resistance to moisture and has a high glass transition temperature as compared with the cured product obtained using a novolak type phenolic resin as a curing agent.
    Type: Grant
    Filed: January 20, 1995
    Date of Patent: June 11, 1996
    Assignee: Mitsui Toatsu Chemicals, Inc.
    Inventors: Tomoyuki Kawabata, Shigeru Iimuro, Teruo Yuasa
  • Patent number: 5516859
    Abstract: This invention relates to polyurethane-forming foundry no-bake binder systems comprising a phenolic resin component and polyisocyanate component. The phenolic resin component comprises a blend of (a) polyphenol resin and (b) a phenolic resole resin. The binder systems have reduced phenol and free formaldehyde due to the presence of the polyphenol resin in the phenolic resin component. Foundry shapes are made by the no-bake process and are used in making ferrous and non ferrous metal castings.
    Type: Grant
    Filed: November 23, 1993
    Date of Patent: May 14, 1996
    Assignee: Ashland Inc.
    Inventors: William R. Dunnavant, Ken K. Chang, Robert B. Fechter
  • Patent number: 5510446
    Abstract: A naphthol-modified phenolic resin having low softening point and good flowability is obtained by allowing a naphthol and a phenol to react with an aldehyde in the presence of an acid catalyst at 60 to 110.degree. C. to obtain a primary reaction mixture, heating the primary reaction mixture in the presence of a strong acid, a super acid or a mixture thereof under ambient pressure at 120 to 180.degree. C. for 1 to 12 hours to obtain a secondary reaction mixture, and subjecting the secondary reaction mixture to vacuum concentration or steam distillation, and the naphthol-modified phenolic resin is suited to use as a curing agent in epoxy resin molding materials for sealing electronic parts.
    Type: Grant
    Filed: June 2, 1995
    Date of Patent: April 23, 1996
    Assignee: Hitachi Chemical Company, Ltd.
    Inventors: Haruaki Sue, Shinsuke Hagiwara, Hiroyuki Saitoh
  • Patent number: 5498647
    Abstract: The invention relates to the use of a resorcinol-glutaraldehyde reaction product as an accelerator for thermosetting phenolic resin and to a method of making the accelerator. Further, the invention relates to a resin blend comprising phenol-formaldehyde and the accelerator and a process for making cellulosic board, oriented strandboard and plywood wherein the binder for the cellulosic board, oriented strandboard and plywood in its uncured form comprises the resin blend of the invention. In another embodiment the accelerator for thermosetting resin comprises resorcinol and glutaraldehyde.
    Type: Grant
    Filed: June 7, 1995
    Date of Patent: March 12, 1996
    Assignee: Borden, Inc.
    Inventors: David W. Shiau, William D. Detlefsen, Earl K. Phillips
  • Patent number: 5494785
    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: February 27, 1996
    Assignee: OCG Microelectronic Materials, Inc.
    Inventors: Joseph J. Sizensky, Thomas R. Sarubbi, Medhat A. Toukhy
  • Patent number: 5491031
    Abstract: A coating composition for application to primed metal substrates as a topcoat is disclosed. The coating composition is especially useful on metal closures for vacuum-packed food products. The coating composition is free of a halide-containing vinyl polymer and comprises: (a) an epoxy novolac resin, (b) a phenolic resin, (c) a polyester, and (d) an elastomer, in (e) a nonaqueous carrier.
    Type: Grant
    Filed: November 14, 1994
    Date of Patent: February 13, 1996
    Assignee: The Dexter Corporation
    Inventor: Lawrence P. Seibel
  • Patent number: 5470924
    Abstract: A process for forming a phenol formaldehyde resin including the steps of: (i) forming a first additive including a glycol and an aromatic dicaborxylic acid; (ii) adding said first additive as well as an alpha hydroxy acid to a first resin component comprising resin precursors including phenol, formaldehyde, an acid catalyst or a base catalyst after said precursors have reacted for 40-55 minutes and/or when water has separated from said precursors; (iii) isolating or storing said first resin component which is maintained in a non cured state by the addition of said first additive; (iv) forming a second additive including zinc chloride, an alpha hydroxy acid, para toluene sulphonic acid, sulphuric or hydrochloric acid and a non aqueous solvent; (v) adding said second additive to a second resin component which includes resin precursors phenol, formaldehyde, methanol and an aliphatic dicarboxylic acid after said precursors have reacted for 20-30 minutes; (vi) combining said first resin component and said second r
    Type: Grant
    Filed: November 24, 1993
    Date of Patent: November 28, 1995
    Inventor: Barry W. Ryan
  • Patent number: 5459223
    Abstract: A naphthol-modified phenolic resin having low softening point and good flowability is obtained by allowing a naphthol and a phenol to react with an aldehyde in the presence of an acid catalyst at 60.degree. to 110.degree. C. to obtain a primary reaction mixture, heating the primary reaction mixture in the presence of a strong acid, a super acid or a mixture thereof under ambient pressure at 120.degree. to 180.degree. C. for 1 to 12 hours to obtain a secondary reaction mixture, and subjecting the secondary reaction mixture to vacuum concentration or steam distillation, and the naphthol-modified phenolic resin is suited to use as a curing agent in epoxy resin molding materials for sealing electronic parts.
    Type: Grant
    Filed: February 8, 1994
    Date of Patent: October 17, 1995
    Assignee: Hitachi Chemical Company
    Inventors: Haruaki Sue, Shinsuke Hagiwara, Hiroyuki Saitoh
  • Patent number: 5416138
    Abstract: An epoxy resin composition used for sealing of semiconductor devices, comprising as essential components:(A) an epoxy resin containing 50-100% by weight, based on total epoxy resin amount, of an epoxy compound represented by formula (I) ##STR1## wherein R.sub.1 to R.sub.8, which may be the same or different, are each an atom or group selected from the group consisting of hydrogen atom, halogen atoms and alkyl groups,(B) a phenolic resin curing agent containing 30-100% by weight, based on total phenolic resin curing agent amount, of a phenolic resin curing agent represented by formula (II) ##STR2## wherein R is paraxylylene group or a residual group which is obtained by removing two hydrogen atoms from dicylopentadiene, a terpene, cyclopentane or cyclohexane, and n is an integer of 0 to 4,(C) an inorganic filler, and(D) a curing accelerator.
    Type: Grant
    Filed: September 15, 1993
    Date of Patent: May 16, 1995
    Assignee: Sumitomo Bakelite Company Limited
    Inventors: Naoki Mogi, Hiroshi Yasuda
  • Patent number: 5413894
    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: May 7, 1993
    Date of Patent: May 9, 1995
    Assignee: OCG Microelectronic Materials, Inc.
    Inventors: Joseph J. Sizensky, Thomas R. Sarubbi, Medhat A. Toukhy
  • Patent number: 5374678
    Abstract: A wood adhesive composition including an effective amount of a phenol-formaldehyde resin; and a modifying agent which agent renders the composition capable of bonding to a hard wood.
    Type: Grant
    Filed: January 15, 1993
    Date of Patent: December 20, 1994
    Assignees: Commonwealth Scientific & Industrial Research Organization, Huntsman Chemical Company Australia Limited
    Inventors: Peter J. Collins, Michael J. Delaney, Yoshikazu Yazaki
  • Patent number: 5374693
    Abstract: The present invention relates to a water insoluble. aqueous alkali soluble novolak resin blend, wherein the resin blend comprises two novolaks having dissimilar relative molecular weights and similar dissolution rates, a process for producing such a resin blend, a photoresist containing such a resin blend and a method for producing a semi-conductor device utilizing such a photoresist.
    Type: Grant
    Filed: December 29, 1992
    Date of Patent: December 20, 1994
    Assignee: Hoechst Celanese Corporation
    Inventors: Thomas J. Lynch, Chester J. Sobodacha, Dana L. Durham
  • Patent number: 5371169
    Abstract: The present invention provides mixture of at least two novolak resins with a molecular weight distribution overlap of at least 50% and having dissolution rates which differ by a factor of at least 2.0. A method is also provided for producing such novolak resin mixtures.
    Type: Grant
    Filed: September 28, 1992
    Date of Patent: December 6, 1994
    Assignee: Hoechst Celanese Corporation
    Inventors: Ping H. Lu, Anthony Canize, Dinesh N. Khanna, M. Dalil Rahman
  • 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: 5364902
    Abstract: The invention relates to the use of a resorcinol-glutaraldehyde reaction product as an accelerator for thermosetting phenolic resin and to a method of making the accelerator. Further, the invention relates to a resin blend comprising phenol-formaldehyde and the accelerator and a process for making cellulosic board, oriented strandboard and plywood wherein the binder for the cellulosic board, oriented strandboard and plywood in its uncured form comprises the resin blend of the invention. In another embodiment the accelerator for thermosetting resin comprises resorcinol and glutaraldehyde.
    Type: Grant
    Filed: December 15, 1992
    Date of Patent: November 15, 1994
    Assignee: Borden, Inc.
    Inventors: David W. Shiau, William D. Detlefsen, Earl K. Phillips
  • Patent number: 5358980
    Abstract: A thermosetting resin composition comprising (A) a naphthalene ring-bearing epoxy resin containing 1 to 10% by weight of a glycidyl naphthol derivative, (B) a naphthalene ring-bearing phenolic resin containing 1 to 10% by weight of a naphthol derivative, and (C) an inorganic filler wherein the content of the naphthol derivatives is 1 to 5% by weight based on the total resin components is suitable for encapsulating semiconductor devices since the composition has a good moldability and cures into a product having a low coefficient of expansion, heat resistance and low moisture absorption.
    Type: Grant
    Filed: January 14, 1994
    Date of Patent: October 25, 1994
    Assignee: Shin-Etsu Chemical Company, Limited
    Inventors: Toshio Shiobara, Kazutoshi Tomiyoshi
  • Patent number: 5340888
    Abstract: The present invention is directed to a phenolic resin composition suitable for use in bonding refractory materials, such as sand, in the production of foundry moulds and cores and also in treating subterranean formations. The phenolic resin composition comprises an esterified phenolic compound, a phenolic novolak resin and a base, which will react to provide final cure in the presence of water or other polar solvent. The composition, once reacted, will bond granular refractory materials. The esterified phenolic compound contains at least one esterified methylol group positioned ortho or para to a phenolic hydroxyl group or an esterified phenolic hydroxyl group. Included within the invention are anhydrous precursors to the reactive phenolic resin composition and also foundry moulding compositions which incorporate the reactive phenolic resin compositions. Other embodiments of the invention include methods for making foundry moulds and cores and methods for curing the reactive phenolic resin composition.
    Type: Grant
    Filed: March 8, 1993
    Date of Patent: August 23, 1994
    Assignee: Borden Inc.
    Inventors: Peter H. R. B. Lemon, James G. King, Graham Murray, Henry Leoni, Arthur H. Gerber
  • Patent number: 5264500
    Abstract: A thermosetting resin designated a "APT" resin is produced by a two-step procedure in which a substituted aromatic compound, preferably diphenyl ether is reacted with formaldehyde to produce an oligomeric backbone, followed by further reaction with a phenol to provide pendant phenolic groups. Finally, the resulting polymer is cyanated with a cyanogen halide.
    Type: Grant
    Filed: July 30, 1991
    Date of Patent: November 23, 1993
    Assignee: Allied-Signal Inc.
    Inventors: George D. Green, William B. Bedwell, Raymond J. Swedo
  • Patent number: 5235022
    Abstract: A block copolymer novolak resin composition comprising at least one unit of the reaction product of an alkali-soluble phenolic polymer and a reactive ortho, ortho bonded oligomer having the formula: ##STR1## wherein x is from 2 to 7; wherein R is selected from hydrogen a lower alkyl group or lower alkoxy group having 1-4 carbon atoms and a halogen group; and Y.sub.1 is either a hydroxyl group; an alkoxy group or a halogen group; and Y.sub.2 is hydrogen, alkyl, alkoxy, halogen, hydroxyl, --CH.sub.2 OH, --CH.sub.2 -- halogen, or --CH.sub.2 -alkoxy group.
    Type: Grant
    Filed: November 23, 1992
    Date of Patent: August 10, 1993
    Assignee: OCG Microelectronic Materials, Inc.
    Inventors: Alfred T. Jeffries, III, Kenji Honda, Andrew J. Blakeney, Sobhy Tadros
  • Patent number: 5223587
    Abstract: Disclosed is an adhesive composition for wood comprising a phenol resin adhesive and a phenol resin highly condensed in a mole ratio (F/P) of formaldehyde (F) to a phenol (P) in the range of 0.8:1 to 1.5:1, having a softening point of 100.degree. to 200.degree. C. and having a number average molecular weight of 2,000 or more, whereby the adhesive is accelerated in hardening to impart fast setting-ability thereto, which causes the pressing temperature to be reduced and makes it possible to raise the allowable moisture content of adherends.
    Type: Grant
    Filed: August 7, 1992
    Date of Patent: June 29, 1993
    Assignee: Oshika Shinko Co. Ltd.
    Inventor: Natsuhi Tsuruta
  • Patent number: 5162428
    Abstract: A phenolic resin composition comprising (a) 30-55% by weight of an alkylbenzene-modified novolac type phenolic resin, (b) 30-55% by weight of a novolac type phenolic resin and (c) 15-30% by weight of a dimethylene ether resole type phenolic resin, and a phenolic resin molding material comprising said composition.
    Type: Grant
    Filed: August 21, 1990
    Date of Patent: November 10, 1992
    Assignee: Sumitomo Bakelite Company Limited
    Inventors: Ken Katoh, Keiji Ooi
  • Patent number: 5145887
    Abstract: There are disclosed methods and compositions for room temperature hardening of phenolic resole resin refractory compositions containing a magnesium oxide hardening agent alone or together with an organic ester. The resin is a low viscosity, low molecular weight resin having a high free phenol content. The magnesium hardening agent has a surface area of at least 20 square meters per gram. The compositions provide adequate working times and room temperature hardening within 24 hours.
    Type: Grant
    Filed: April 4, 1991
    Date of Patent: September 8, 1992
    Assignee: Borden, Inc.
    Inventors: John G. Taylor, Arthur H. Gerber
  • Patent number: 5130410
    Abstract: This invention relates to alternating and block copolymer resins and methods for preparing the same. The alternating copolymer resins are formed from the reaction of a preformed bishydroxymethyl phenol and a reactive phenolic compound. The alternating copolymer may then be further reacted with a second reactive compound in the presence of an aldehyde to form the substantially block copolymer. The alternating and block copolymer resins are characterized by enhanced ortho-, ortho-coupling and low molecular weight distribution.
    Type: Grant
    Filed: February 27, 1991
    Date of Patent: July 14, 1992
    Assignee: Shipley Company Inc.
    Inventor: Anthony Zampini
  • Patent number: 5108824
    Abstract: Epoxy resins have been reacted with a copolymer of a diunsaturated aliphatic compound and acrylonitrile or methacrylonitrile and a siloxane-containing polymer resulting in a rubber modified epoxy resin suitable for use in electrical and electronic component encapsulation formulations which provide such components with improved thermal shock performance. The rubber modified epoxy resins have improved flexural properties with minimal reduction in glass transition temperature.
    Type: Grant
    Filed: February 6, 1990
    Date of Patent: April 28, 1992
    Assignee: The Dow Chemical Company
    Inventors: Chun S. Wang, Douglas G. Kleweno
  • 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.