Solid Polymer Or Sicp Derived From At Least One Heterocyclic Monomer Or Aldehyde Or Aldehyde Derivative Patents (Class 522/166)
  • Patent number: 5541036
    Abstract: A negative photoresist composition comprising:(A) a compound represented by the following formula (I): ##STR1## wherein R.sup.1 and R.sup.2 which are different from each other represent a hydrogen atom or a group represented by the following formula (II): ##STR2## (B) an alkoxymethylated melamine, and (C) a novolak resin.The photoresist composition has resolution below submicron, and can form resist patterns with an ideal rectangular profile.
    Type: Grant
    Filed: April 16, 1993
    Date of Patent: July 30, 1996
    Assignee: Hoechst Japan Limited
    Inventors: Akihiko Igawa, Masato Nishikawa, Georg Pawlowski, Ralph Dammel
  • Patent number: 5512608
    Abstract: A multi-part composition is provided which is suitable for use as an adhesive, a potting compound, a coating or a sealant. It consists of a polymerizable acrylate formulation and an activating formulation, the latter usually comprising an amine-aldehyde condensation product diluted with a liquid vinyl ether; liquid epoxides may also be included as diluents in the activating formulation.
    Type: Grant
    Filed: January 27, 1995
    Date of Patent: April 30, 1996
    Assignee: Dymax Corporation
    Inventors: Andrew G. Bachmann, Stephen E. Cantor
  • Patent number: 5494944
    Abstract: A hardenable composition containing:a) a material polymerizable by free radical or cationic polymerization,b) at least one iron compound of the formula I ##EQU1## wherein a is 1 or 2 and q is 1, 2 or 3,L is a divalent to heptavalent metal or non-metal,Q is a halogen atom,m is an integer corresponding to the sum of the values of L and q,R.sup.1 is an unsubstituted or substituted .eta..sup.6 -benzene andR.sup.2 is an unsubstituted or substituted cyclopentadienyl anion, andc) at least one sensitizer for the compound of the formula I,and, in the case of materials polymerizable by free radical polymerization, also d) an electron acceptor as an oxidizing agent, which is also advantageously used concomitantly for the material polymerizable by cationic polymerization. The composition is suitable for the production of protective layers and photographic images.
    Type: Grant
    Filed: August 18, 1994
    Date of Patent: February 27, 1996
    Assignee: Ciba-Geigy Corporation
    Inventors: Kurt Meier, Hans Zweifel
  • Patent number: 5489664
    Abstract: Crosslinkable liquid composition based on organic isocyanates and epoxy compounds, comprising the following components:(A) an organic polyisocyanate;(B) a polyepoxide or mixture of a polyepoxide and a monoepoxide; and(C) a catalyst constituted by at least one cyanoderivative containing a quaternary nitrogen atom,which composition can be polymerized at temperatures of 40.degree. C. or higher, by a process comprising exposure thereof to a non-ionizing electromagnetic radiation having a frequency comprised in the microwave range of frequencies, to obtain a solid material endowed with an excellent combination of physical, chemical and mechanical properties.
    Type: Grant
    Filed: November 4, 1994
    Date of Patent: February 6, 1996
    Assignees: Enichem S.p.A., Eniricerche S.p.A.
    Inventors: Fabrizio Parodi, Renata Gerbelli, Mark De Meuse
  • Patent number: 5439779
    Abstract: The present invention provides a photoimageable soldermask that may be applied using aqueous solvents, thereby reducing the emission of organic solvents. The soldermask contains an epoxy based resin system comprised of at least one epoxy resin, a coating agent, and preferably a cationic photoinitiator and a dye.
    Type: Grant
    Filed: June 13, 1994
    Date of Patent: August 8, 1995
    Assignee: International Business Machines Corporation
    Inventors: Richard A. Day, Donald H. Glatzel, David J. Russell, Jeffrey D. Gelorme, John R. Mertz
  • Patent number: 5438082
    Abstract: In order to produce a polymer electrolyte membrane from sulfonated, aromatic polyether ketone, an aromatic polyether ketone of the formula (I) ##STR1## in which Ar is a phenylene ring having p- and/or m-bonds,Ar' is a phenylene, naphthylene, biphenylene, anthrylene or another divalent aromatic unit,X, N and M, independently of one another are 0 or 1,Y is 0, 1, 2 or 3,P is 1, 2, 3 or 4,is sulfonated and the sulfonic acid is isolated. At least 5% of the sulfonic groups in the sulfonic acid are converted into sulfonyl chloride groups, and these are reacted with an amine containing at least one crosslinkable substituent or a further functional group, and unreacted sulfonyl chloride groups are subsequently hydrolyzed. The resultant aromatic sulfonamide is isolated and dissolved in an organic solvent, the solution is converted into a film, and the crosslinkable substituents in the film are then crosslinked.In specific cases, the crosslinkable substituents can be omitted.
    Type: Grant
    Filed: June 10, 1993
    Date of Patent: August 1, 1995
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Freddy Helmer-Metzmann, Frank Osan, Arnold Schneller, Helmut Ritter, Konstantin Ledjeff, Roland Nolte, Ralf Thorwirth
  • Patent number: 5414025
    Abstract: A method for the crosslinking of polymeric electrolytes is presented. The method achieves crosslinking by means of ultraviolet radiation. The resulting crosslinked polymers are stable and useful as solid state battery electrolytes.
    Type: Grant
    Filed: September 30, 1992
    Date of Patent: May 9, 1995
    Assignee: The Penn State Research Foundation
    Inventors: Harry R. Allcock, Constance J. Nelson, William D. Coggio
  • Patent number: 5385956
    Abstract: The method concerns preparing a polymer composition containing an electrically conductive polymer which is formed, in the presence of a catalyst, from polymerizable monomer units that are converted from non-polymerizable precursor monomers with the aid of a sufficiently energy-intense light source. In this method according to the invention is that the precursor monomers have a structure according to formula (I). The method according to the invention makes it possible to very easily and rapidly, and thus economically, prepare a polymer composition containing an electrically conductive polymer. Furthermore, the method according to the invention permits a polymer composition to be produced that contains an electrically conductive polymer in specifically pre-selected areas.
    Type: Grant
    Filed: July 15, 1993
    Date of Patent: January 31, 1995
    Assignee: DSM N.V.
    Inventors: Ronald M. A. M. Schellekens, Hans K. Van Dijk
  • Patent number: 5371115
    Abstract: A hardenable composition containing:a) a material polymerizable by free radical or cationic polymerization,b) at least one iron compound of the formula I ##EQU1## wherein a is 1 or 2 and q is 1, 2 or 3,L is a divalent to heptavalent metal or non-metal,Q is a halogen atom,m is an integer corresponding to the sum of the values of L and q,R.sup.1 is an unsubstituted or substituted .eta..sup.6 -benzene andR.sup.2 is an unsubstituted or substituted cyclopentadienyl anion, andc) at least one sensitizer for the compound of the formula I,and, in the case of materials polymerizable by free radical polymerization, also d) an electron acceptor as an oxidizing agent, which is also advantageously used concomitantly for the material polymerizable by cationic polymerization. The composition is suitable for the production of protective layers and photographic images.
    Type: Grant
    Filed: April 15, 1992
    Date of Patent: December 6, 1994
    Assignee: Ciba-Geigy Corporation
    Inventors: Kurt Meier, Hans Zweifel
  • Patent number: 5356947
    Abstract: The present invention provides controllably curable photoiniferter containing adhesive compositions which are suitable for the mounting of microelectronic devices such as flip chips onto transparent wiring boards, a method of making the adhesive compositions, and a method of using the adhesive compositions in order to bond microelectronic devices to transparent wiring boards by intermittent exposure of the adhesive composition to a radiant energy source. The adhesive compositions can be cured in a stepwise fashion by intermittent controlled exposure to a source of radiation thus providing exactly the amount of cure and hardening desired.
    Type: Grant
    Filed: October 29, 1992
    Date of Patent: October 18, 1994
    Assignee: Minnesota Mining and Manufacturing Company
    Inventors: Mahfuza B. Ali, Jean M. Pujol
  • Patent number: 5340697
    Abstract: A negative type photoresist composition comprising a light-sensitive s-triazine compound represented by formula (I), an acid-crosslinkable material, and an alkali soluble resin: ##STR1## wherein R.sub.1 and R.sub.2, which may be the same or different, each represents a hydrogen atom, an alkyl group, a substituted alkyl group, an aryl group, a substituted aryl group, a group represented by formula (II) or (III), or R.sub.1 and R.sub.2 may form a heterocyclic group consisting of non-metal atoms bonded to a nitrogen atom; R.sub.3 and R.sub.4 each represent a hydrogen atom, a halogen atom, an alkyl group, or an alkoxy group; X and Y, which may be the same or different, each represents a chlorine atom or a bromine atom; and m and n each represents 0, 1 or 2; ##STR2## wherein R.sub.5 represents an alkyl group, a substituted alkyl group, an aryl group, or a substituted aryl group; and R.sub.6 and R.sub.
    Type: Grant
    Filed: June 9, 1993
    Date of Patent: August 23, 1994
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Hiroshi Yoshimoto, Kazuya Uenishi, Tadayoshi Kokubo
  • Patent number: 5326792
    Abstract: A photosensitive cover coating agent forming an insulating, protective coating having superior compatibility, sensitivity, heat resistance, adhesion, electrical properties and flexibility is provided,which coating agent is obtained by mixing a polymer (A) of repetition units of the formula ##STR1## wherein R.sup.1 is ##STR2## R.sup.2 is a divalent organic group, a compound (B) containing two or more (meth)acryloyl groups in one molecule,a compound (C) of the formula ##STR3## wherein Z is a divalent aliphatic or alicyclic group, R.sup.3 is H, monovalent organic group or characteristic group and R.sup.4 is H or --Z--R.sup.3, in 0.01 to 0.80 mol equivalent based on compound (B), the total quantity of (B) and (C) being 20 to 200 wt. parts per 100 wt. parts of (A), anda photopolymerization initiator or a sensitizing agent (D), in 0.5 to 20 wt. parts per 100 wt. parts of (A).
    Type: Grant
    Filed: November 23, 1992
    Date of Patent: July 5, 1994
    Assignee: Chisso Corporation
    Inventors: Yoshinori Masaki, Kouichi Kunimune, Hirotoshi Maeda
  • Patent number: 5314983
    Abstract: Mixtures of polyisocyanates and epoxides are cured by microwave irradiation, optionally with microwave or thermal post-curing to produce cured polymer articles having good chemical, electrical and mechanical properties.
    Type: Grant
    Filed: November 9, 1992
    Date of Patent: May 24, 1994
    Assignee: Enichem S.p.A.
    Inventors: Mark T. DeMeuse, Fabrizio Parodi
  • Patent number: 5304456
    Abstract: A negative photoresist composition containing an alkali-soluble resin which is obtainable through a condensation reaction of an aldehyde with a phenol compound containing a compound of the general formula: ##STR1## wherein R.sup.1 to R.sup.9 are independently a hydrogen atom, an alkyl group, an alkenyl group, an alkylcarbonyl group, a halogen atom or a hydroxyl group, provided that at least one of R.sup.1 to R.sup.9 is a hydroxyl group and, at the ortho- or para-position to the hydroxyl group, at least two hydrogen atoms are present; a cross linking agent; and a photo-acid generator, and a negative photoresist composition comprising an alkali-soluble resin, a cross linking agent and a photo-acid generator having a trifluoromethanesulfonic acid ester group, which can increase resolution and contrast of a photoresist pattern.
    Type: Grant
    Filed: January 29, 1992
    Date of Patent: April 19, 1994
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Yuji Ueda, Hiromi Ueki, Naoki Takeyama, Takehiro Kusumoto
  • Patent number: 5258265
    Abstract: A radiation-sensitive mixture useful as a negative-working photoresist composition comprising:(a) at least one novolak resin; and(b) a photoactive benzannelated acetic acid selected from formula (I): ##STR1## wherein X is either an oxygen, sulfur or --C--H.sub.2.
    Type: Grant
    Filed: November 23, 1992
    Date of Patent: November 2, 1993
    Assignee: Olin Corporation
    Inventors: Sydney G. Slater, Stanley A. Ficner
  • Patent number: 5258260
    Abstract: A radiation-sensitive mixture useful as a negative-working photoresist composition comprising:(a) at least one novolak resin; and(b) a photoactive benzennelated acetic acid selected from formula (I): ##STR1## wherein X is either an oxygen, sulfur or --C--H.sub.2.
    Type: Grant
    Filed: November 23, 1992
    Date of Patent: November 2, 1993
    Assignee: Olin Corporation
    Inventors: Sydney G. Slater, Stanley A. Ficner
  • Patent number: 5215860
    Abstract: Energy polymerizable compositions comprising at least one cyanate monomer and as curing agent an organometallic compound are disclosed. The compositions are useful in applications requiring high performance, such as high temperature performance; in composites, particularly structural composities; structural adhesives; tooling for structural composities; electronic applications such as printed wiring boards and semiconductor encapsulants; graphic arts; injection molding and prepregs; and high performance binders.
    Type: Grant
    Filed: August 19, 1988
    Date of Patent: June 1, 1993
    Assignee: Minnesota Mining and Manufacturing Company
    Inventors: Fred B. McCormick, Katherine A. Brown-Wensley, Robert J. DeVoe
  • Patent number: 5215861
    Abstract: Reaction products of organosilane compounds and a novolac resin having phenolic groups are capable of generating either positive or negative tone patterns depending on the time and temperature of processing.
    Type: Grant
    Filed: March 17, 1992
    Date of Patent: June 1, 1993
    Assignee: International Business Machines Corporation
    Inventors: Peter A. Agostino, Adolph Herbst, Frederick M. Pressman
  • Patent number: 5185209
    Abstract: A predetermined pattern of a dielectric polymer is formed on a substrate from a prepolymer which is an ether of the oligomeric condensation product of a dihydric phenol and formaldehyde having the formula ##STR1##
    Type: Grant
    Filed: March 28, 1991
    Date of Patent: February 9, 1993
    Assignee: Allied-Signal Inc.
    Inventor: Joseph J. Zupancic
  • Patent number: 5185210
    Abstract: A predetermined pattern of a dielectric polymer is formed on a substrate from a mixture of prepolymers which are the ethers of the oligomeric condensation product of (a) dihydric phenol and formaldehyde and (b) a dialdehyde and 3 to 4 moles of a phenol.
    Type: Grant
    Filed: March 28, 1991
    Date of Patent: February 9, 1993
    Assignee: Allied-Signal Inc.
    Inventor: Joseph J. Zupancic
  • Patent number: 5178987
    Abstract: A radiation-sensitive mixture useful as a negative-working photoresist composition comprising:(a) at least one novolak resin; and(b) a photoactive benzannelated acetic acid selected from formula (I): ##STR1## wherein X is either an oxygen, sulfur or ##STR2##
    Type: Grant
    Filed: April 24, 1989
    Date of Patent: January 12, 1993
    Assignee: Olin Corporation
    Inventors: Sydney G. Slater, Stanley A. Ficner
  • Patent number: 5158989
    Abstract: A photocurable ink composition for forming patterns resistive to electroless plating is disclosed which includes (a) an epoxy resin, (b) an aliphatic polyol polyglycidyl ether as a reactive, viscosity controlling agent, (c) a photopolymerization catalyst, and (d) hydrophobic silica particles as a thixotropic agent.
    Type: Grant
    Filed: October 9, 1990
    Date of Patent: October 27, 1992
    Assignee: Somar Corporation
    Inventors: Osamu Ogitani, Toru Shirose
  • Patent number: 5114741
    Abstract: A predetermined pattern of a dielectric polymer is formed on a substrate from a mixture of prepolymers which are ethers of the reaction products of (a) a dicyclopentadiene and a phenol and (b) a dialdehyde and 3 to 4 moles of a phenol.
    Type: Grant
    Filed: December 19, 1990
    Date of Patent: May 19, 1992
    Assignee: Allied-Signal Inc.
    Inventors: Joseph J. Zupancic, Daniel C. Blazej, Howard A. Fraenkel
  • Patent number: 5102772
    Abstract: Photocurable compositions with, as photoinitiator, sulfonium salts of the formula: ##STR1## wherein Ar is a fused aromatic radical; R.sub.1 is a divalent organic bridge; each R.sub.2 and R.sub.3 individually is an alkyl, aryl, alkaryl, aralkyl or substituted aryl, provided that not more than one of R.sub.2 and R.sub.3 is alkyl; and A is a non-nucleophilic anion; use thereof and preparation thereof.
    Type: Grant
    Filed: July 10, 1991
    Date of Patent: April 7, 1992
    Assignee: IBM
    Inventors: Raymond W. Angelo, Jeffrey D. Gelorme, Joseph P. Kuczynski, William H. Lawrence, Socrates P. Pappas, Logan L. Simpson
  • Patent number: 5089536
    Abstract: An energy polymerizable composition and process therefore, comprising a cationically polymerizable material and a catalytically effective amount of an ionic salt of an organometallic complex cation as polymerization initiator, said ionic salt of an organometallic complex cation being capable of adding an intermediate strength nucleophile or upon photolysis capable of liberating at least one coordination site, said metal in said organometallic complex cation being selected from elements of Periodic Groups IVB, VB, VIB, VIIB, and VIIIB are disclosed. Certain of the organometallic metallic polymerization initiators are novel cationic salts.
    Type: Grant
    Filed: November 22, 1982
    Date of Patent: February 18, 1992
    Assignee: Minnesota Mining and Manufacturing Company
    Inventor: Michael C. Palazzotto
  • Patent number: 5041358
    Abstract: A composition containing a polymeric material obtained by interreacting an epoxy-novolak polymer with an organosilicon compound, a radiation sensitive onium salt, and a near U.V. sensitizer.
    Type: Grant
    Filed: April 17, 1989
    Date of Patent: August 20, 1991
    Assignee: International Business Machines Corporation
    Inventors: Michael Hatzakis, Jane M. Shaw, Kevin J. Stewart
  • Patent number: 5009970
    Abstract: A solid polymer electrolyte is in the form of a gel comprising a complex of a solid polymer (e.g. poly(ethene oxide) and an alkali metal salt (e.g. LiClO.sub.4), the polymer being cross-linked to inhibit its transformation from an amorphous form to a crystalline form thereby to improve the alkali metal ion conductivity of the electrolyte at lower temperatures. The electrolyte may be made by irradiating (e.g. by gamma radiation or an electron beam) a solution, preferably aqueous, of the complex to cause the polymer to cross-link and form a gel. The electrolyte may be used as a component in a solid state electrochemical cell (e.g. for a rechargeable lithium battery), where the gel form of the electrolyte assists fabrication.
    Type: Grant
    Filed: July 25, 1988
    Date of Patent: April 23, 1991
    Assignee: United Kingdom Atomic Energy Authority
    Inventors: Esam Kronfli, Keith V. Lovell, Alan Hooper, Robin J. Neat
  • Patent number: 4975471
    Abstract: A photo-curable epoxy resin type composition which comprises (a) an epoxy resin, (b) at least one compound selected from the group consisting of (i) a compound having a group, other than an imido group, which is represented by the formula --CONH and (ii) an aromatic amine, (c) an organic metal compound, where said metal is selected from the group consisting of titanium, vanadium, chromium, manganese, iron, cobalt, nickel, copper, zinc, aluminum and zirconium; and (d) an organic silicon compound having at least one group selected from the group consisting of a peroxysilyl group and an o-nitrobenzyloxy group capable of forming a silanol group by irradiation with light. The photo-curable epoxy resin type composition according to this invention is capable of readily curing by light (ultraviolet ray in particular) and also capable of heat curing at a temperature of 150.degree. C.
    Type: Grant
    Filed: August 29, 1988
    Date of Patent: December 4, 1990
    Assignee: Kabushiki Kaisha Toshiba
    Inventors: Shuzi Hayase, Shuichi Suzuki, Moriyasu Wada
  • Patent number: 4939229
    Abstract: A method for preparing branched novolak polymers possessing excellent lithographic performance is provided. The method involves the acid catalyzed reaction of a phenol with a tris- or tetrakis(dialkylaminoalkyl)phenol followed by purification of the reaction product. The branched novolaks are soluble in aqueous base and organic solvent solutions and are particularly useful as the polymeric component of either positive acting or negative acting photoresist compositions.
    Type: Grant
    Filed: May 12, 1989
    Date of Patent: July 3, 1990
    Assignee: Rohm and Haas Company
    Inventor: Leonard E. Bogan, Jr.
  • Patent number: 4927865
    Abstract: Anthraquinones of formula I ##STR1## wherein X is the group --CR.sup.2 R.sup.3 --, where R.sup.2 is H, --CH or C.sub.1 -C.sub.5 -alkyl and R.sup.3 is H or --CN, R.sup.1 is H or C.sub.1 -C.sub.5 -alkyl and R is a direct bond or linear or branched C.sub.1 -C.sub.18 -alkylene which, alone or together with the --CR.sup.2 R.sup.3 -- group, can be interrupted by one or more --O-- when R.sup.2 and/or R.sup.3 are not --CN, and curable compositions comprising (a) an epoxy resin, (b) a hardener if necessary, (c) an anthraquinone of formula I and (d) an amino alcohol. The cured compositions are photosensitive and are suitable for the preparation of coatings and metallic images by electroless metal deposition.
    Type: Grant
    Filed: May 12, 1989
    Date of Patent: May 22, 1990
    Assignee: Ciba-Geigy Corporation
    Inventors: Rudolf Duthaler, Jurgen Finter, Walter Fischer, Visvanathan Ramanathan
  • Patent number: 4921923
    Abstract: Oligomeric condensation products of certain diketones and phenols can be end-capped with a vinylbenzyl moiety and certain other moieties, especially alkyl groups, to afford thermosetting resins particularly valuable in making laminated circuit boards. Resins prepared by the reaction of 1 molar proportion of diacetylbenzene with from 3.5 to 4.0 molar proportions of phenol and end-capped with from 50 to 100% vinylbenzyl groups with the remainder being alkyls of 1 through 11 carbon atoms are particularly useful.
    Type: Grant
    Filed: November 18, 1988
    Date of Patent: May 1, 1990
    Assignee: Allied Signal Inc.
    Inventors: Joseph J. Zupancic, Jean M. J. Frechet, Andrew M. Zweig, Jeffrey P. Conrad
  • Patent number: 4871645
    Abstract: A positive-working photoresist composition is disclosed. The composition comprises a light-sensitive compound represented by general formula (A) and an alkali-soluble novolak resin. ##STR1## wherein R.sub.a, R.sub.b, R.sub.c, R.sub.d, R.sub.e and R.sub.f, which may be the same or different, each represents H, --X--R.sub.1, ##STR2## provided that among the six substituents represented by R.sub.a to R.sub.f, the number of the substituents representing H is a real number of more than 0 and not more than 3 calculated in terms of average value per molecule of the light-sensitive compound, the number of the substituents representing --X--R.sub.1 is a real number of not less than 0.3 calculated in terms of average value per molecule of the light-sensitive compound, and the number of the substituents representing ##STR3## is a real number of not less than 2.5 caluclated in terms of average value per molecule of the light-sensitive compound; X represents a simple bond, ##STR4## R.sub.
    Type: Grant
    Filed: June 6, 1988
    Date of Patent: October 3, 1989
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Kazuya Uenishi, Tadayoshi Kokubo, Yasumasa Kawabe
  • Patent number: 4839253
    Abstract: An electrodepositable photosensitive resin which is a phenolic novolak resin having(i) at least part of the phenolic hydroxyl groups thereof replaced by a quinone diazide sulphonyloxy group, and(ii) at least part of the aromatic rings thereof substituted in a position ortho and/or para to a phenolic hydroxyl group or quinone diazide sulphonyloxy group by a group of formula --CH(R.sup.1)R.sup.2 whereR.sup.1 represents a hydrogen atom, or an alkyl, aryl or carboxylic acid group, andR.sup.2 represents a sulphonic acid group --SO.sub.3 H or a group of formula --A--R.sup.3 --X,R.sup.3 represents an aliphatic, aromatic or araliphatic divalent group which may be substituted by a carboxlic, sulphonic or phosphonic acid group,A represents a sulphur atom or a group of formula --N(R.sup.4)--, where R.sup.4 represents a hydrogen atom or an alkyl group which may be substituted by a carboxylic acid group or by an optionally etherified hydroxyl group, or R.sup.3 and R.sup.
    Type: Grant
    Filed: August 28, 1987
    Date of Patent: June 13, 1989
    Assignee: Ciba-Geigy Corporation
    Inventors: Christopher G. Demmer, Edward Irving
  • Patent number: 4835193
    Abstract: A photopolymerizable epoxy resin composition comprising (a) an epoxy resin and (b) a heteropoly-acid aromatic sulfonium salt or a heteropoly-acid aromatic iodonium salt as a photocuring catalyst exhibits rapid photopolymerization, with the cured product being great in hardness, the corrosive action being weak, and the electrical properties being excellent. The industrial utility of the composition is therefore substantial.
    Type: Grant
    Filed: May 7, 1987
    Date of Patent: May 30, 1989
    Assignee: Kabushiki Kaisha Toshiba
    Inventors: Shuzi Hayase, Yasunobu Onishi, Shuichi Suzuki, Moriyasu Wada
  • Patent number: 4816498
    Abstract: Oligomeric condensation products of certain dialdehydes and phenols can be end-capped with a vinylbenzyl moiety and certain other moieties, especially alkyl groups, to afford thermosetting resins particularly valuable in making laminated circuit boards. Resins prepared by the reaction of 1 molar proportion of glyoxal with from 3 to 4 molar proportions of phenol and end-capped with from 50 to 85% vinylbenzyl groups with the remainder being alkyls of 1 through 11 carbon atoms are particularly useful.
    Type: Grant
    Filed: November 30, 1987
    Date of Patent: March 28, 1989
    Assignee: Allied-Signal Inc.
    Inventors: Joseph J. Zupancic, Jean M. J. Frechet, Andrew M. Zweig, Jeffery P. Conrad
  • Patent number: 4758608
    Abstract: Ultraviolet curable terpolymers of trioxane, from at least 65 weight percent to about 75 weight percent of 1,3-dioxolane and from about 2 weight percent to about 20 weight percent of a monoethylenically unsaturated aliphatic diol formal having at least 4 carbon atoms in its main chain, e.g., 4,7-dehydro- 1,3-dioxepin, which are non-crystalline at room temperature or above are disclosed. These terpolymers, when admixed with a multifunctional crosslinking monomer, e.g., a multifunctional acrylate such as 1,6-hexanediol diacrylate, and a photosensitizer, e.g., a benzoin compound such as benzoin isobutyl ether, can be cured to an insoluble, non-tacky, rubbery state using UV radiation. The thus-cured polymeric materials form useful crosslinked films, and when cryogenically ground to a suitable small particle size can be blended with conventionally prepared crystalline oxymethylene homo-, co- and terpolymers to improve the latters' impact properties.
    Type: Grant
    Filed: September 14, 1987
    Date of Patent: July 19, 1988
    Assignee: Hoechst Celanese Corporation
    Inventors: George L. Collins, Paul Zema, William M. Pleban
  • Patent number: 4734481
    Abstract: Homopolymers or copolymers of organometallic, end-capped polyphthalaldehydes containing the repeating unit of formula I ##STR1## wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are each independently of the other hydrogen, halogen, cyano, nitro, carboxyl, hydroxyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkylthio or C.sub.1 -C.sub.4 alkoxycarbonyl, and at least one of the substituents R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are a group --Q(R.sup.5).sub.3 or --Q(R.sup.6).sub.3, where Q is Si, Sn, Ge, CH.sub.2 --Si or O--Si, R.sup.5 is C.sub.1 -C.sub.12 alkyl and R.sup.6 is C.sub.6 -C.sub.10 aryl, are suitable for producing dry-developed, plasma-resistant photoresists required for the production of structured images, especially for microelectronics.
    Type: Grant
    Filed: January 8, 1987
    Date of Patent: March 29, 1988
    Assignee: Ciba-Geigy Corporation
    Inventor: Alfred Steinmann
  • Patent number: 4681923
    Abstract: An electrodepositable photosensitive modified phenolic novolak resin of general formula ##STR1## where Ar.sup.1 represents a divalent aromatic group linked through aromatic carbon atoms to the indicated groups --OR.sup.2 and --CH(R.sup.1)--,Ar.sup.2 represents a trivalent aromatic group linked through aromatic carbon atoms to the indicated groups --OR.sup.2 and --CH(R.sup.1)--,R.sup.1 represents a hydrogen atom or an alkyl, aryl or carboxyl group,R.sup.2 represents a hydrogen atom, an alkyl group which may be substituted by a hydroxyl or alkoxy group, or a group of formula --CO--R.sup.3 --COOH, --SO.sub.2 R.sup.4, --COR.sup.5 or --SO.sub.2 R.sup.5, at least 1% of the groups R.sup.2 representing a group --CO--R.sup.3 --COOH and at least 4% of the groups R.sup.2 representing a group --SO.sub.2 R.sup.4,R.sup.3 denotes a divalent aliphatic, cycloaliphatic, aromatic or araliphatic group,R.sup.4 denotes a 1,2-benzoquinone diazide group or 1,2-naphthoquinone diazide groupR.sup.
    Type: Grant
    Filed: February 21, 1986
    Date of Patent: July 21, 1987
    Assignee: Ciba-Geigy Corporation
    Inventors: Christopher G. Demmer, Edward Irving
  • Patent number: 4663268
    Abstract: There is disclosed a resist comprising a radiation-sensitive sensitizer that produces, with a binder, imagewise differential solubility when imagewise exposed.
    Type: Grant
    Filed: February 24, 1986
    Date of Patent: May 5, 1987
    Assignee: Eastman Kodak Company
    Inventors: Sam R. Turner, Conrad G. Houle
  • Patent number: 4659788
    Abstract: A radiation curable adhesive composition comprising a liquid oligomer, a chain transfer agent, and an N-methyl compound can give a surface protective film which is slightly influenced in adhesive strength with the lapse of time, and excellent in weather resistance and heat resistance.
    Type: Grant
    Filed: April 1, 1985
    Date of Patent: April 21, 1987
    Assignee: Hitachi Chemical Co., Ltd.
    Inventors: Tomohisa Ohta, Akihiko Dobashi, Hisashige Kanbara, Yasuyuki Seki
  • Patent number: 4609686
    Abstract: 100 percent solids epoxy, nitrile coating compositions comprising:(a) epoxy resins, and(b) epoxy-nitrile monomers which are useful for protective coatings.The invention further includes a process for producing the 100 percent solids epoxy nitrile coating compositions comprising:(1) forming a mixture of the epoxy resins with the epoxy nitrile monomers and curing agents,(2) applying the mixture to a substrate to form a coating, and(3) curing the coating so that in situ copolymerization of the epoxy resin and epoxy-nitrile monomer results in a multifunctional epoxy nitrile coating system.
    Type: Grant
    Filed: April 19, 1985
    Date of Patent: September 2, 1986
    Assignee: The Standard Oil Company
    Inventors: Paul Giordano, Jr., Richard C. Smierciak
  • Patent number: 4593052
    Abstract: Polymerizable compositions contain (A) a cationically polymerizable material, such as an epoxide resin, a phenoplast or a cyclic vinyl ether, (B) a hydroxy compound such as styreneallyl alcohol copolymer, and (c) an aromatic iodosyl salt of formula ##STR1## where R.sup.3 and R.sup.4, which may be the same or different, each represent a monovalent aromatic radical having from 4 to 25 carbon atoms, x denotes 1, 2 or 3, and Z.sup.x- denotes an x-valent anion of a protic acid.Suitable salts of formula II include diphenyliodosyl hexafluorophosphate and tetrafluoroborate. The compositions may be photopolymerized or they may be thermally polymerized in the presence, as catalyst for the iodosyl salt, of a salt or complex of a d-block transition metal, a stannous salt, an organic peroxide or an activated .alpha.-hydroxy compound.The compositions may be used as surface coatings and adhesives, and in the preparation of printing plates, printed circuits and reinforced composites.
    Type: Grant
    Filed: November 19, 1984
    Date of Patent: June 3, 1986
    Assignee: Ciba-Geigy Corporation
    Inventor: Edward Irving