Halogen Compound Containing Patents (Class 430/925)
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Patent number: 5272042Abstract: Disclosed is a positive photoresist. The photoresist has as its polymeric component a substantially water and base insoluble, photolabile polymer. The photoresist further includes a photo acid generator that is capable of forming a strong acid. This photo acid generator may be a sulfonate ester derived from a N-hydroxyamide, or a N-hydroxyimide. Finally, the photoresist composition includes an appropriate photosensitizer.Type: GrantFiled: September 17, 1991Date of Patent: December 21, 1993Assignee: International Business Machines CorporationInventors: Robert D. Allen, William R. Brunsvold, Burton J. Carpenter, William D. Hinsberg, Joseph LaTorre, Michael G. McMaster, Melvin W. Montgomery, Wayne M. Moreau, Logan L. Simpson, Robert J. Tweig, Gregory M. Wallraff
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Patent number: 5219700Abstract: A photosensitive composition comprising (a) a 1,2-naphthoquinone-2-diazido-4-sulfonic acid ester compound, (b) alkali-soluble resin, (c) a halomethyloxadiazole compound which releases halogen free radicals by irradiation with actinic rays and (a) a dye which interacts withthe decomposition product of said halomethyloxydiazole compound and discolors or develops color. The composition exhibits excellent development latitude, light safety, visible-on-exposure characteristic and printing resistance.Type: GrantFiled: March 24, 1992Date of Patent: June 15, 1993Assignees: Mitsubishi Kasei Corporation, Konica CorporationInventors: Hideyuki Nakai, Kiyoshi Goto, Hiroshi Tomiyasu, Yoshiko Fujita
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Patent number: 5212046Abstract: A photoacid-generating photoresist composition sensitized with an aromatic, multi-ring, heterocylcic nitrogen containing sensitizer, preferably a ring extended phenothiazine derivative. The use of the sensitizer permits exposure of photoresists to near UV irradiation where such photoresists have heretofore been exposed to deep UV irradiation. The invention is especially useful for acid hardening photoresist systems.Type: GrantFiled: June 28, 1991Date of Patent: May 18, 1993Assignee: Shipley Company Inc.Inventors: Angelo A. Lamola, Gary Calabrese, Roger Sinta
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Patent number: 5141841Abstract: A radiation-sensitive compound has the general formula ##STR1## wherein A represents the ring members required to complete a 5- or 6-membered heterocyclic ring which may optionally be fused to an optionally substituted aromatic nucleus,B represents H, acyl, aroyl, heterocyclyl carbonyl or ##STR2## R represents an optionally substituted alkyl group, E and G, which may be the same or different, each represents H or CH.sub.p X.sub.3-p,J and K, which may be the same or different, each represents an aryl or heterocyclic group, which may optionally include a substituent additional to E or G,X represents Cl or Br, and m,n and p, which may be the same or different, each represents an integer equal to 0, 1 or 2.The compound can be used to form radiation sensitive compositions for the production of radiation sensitive plates in lithographic printing plate manufacture.Type: GrantFiled: August 17, 1989Date of Patent: August 25, 1992Assignee: Vickers PLCInventor: John R. Wade
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Patent number: 5141840Abstract: A light-sensitive composition comprising:(a) a polysiloxane compound having at least 1 mol % of a structural unit derived from a product of a thermal cycloaddition reaction between a compound of formula (I), (II), (III) or (IV) and a compound of formula (V), (VI), (VII) or (VIII), and(b) an onium salt compound.Type: GrantFiled: January 29, 1991Date of Patent: August 25, 1992Assignee: Fuji Photo Film Co., Ltd.Inventors: Kazuyoshi Mizutani, Toshiaki Aoai
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Patent number: 5128231Abstract: A photoresist composition is disclosed. The photoresist composition comprises a base resin, a photosensitizer, and a solvent. The base resin comprises polyhydroxystyrene represented by the following structural formula (I): ##STR1## (wherein k is a positive integer). The photosensitizer comprises a polyhalogen compound(s). The photoresist composition of the present invention has dry etching resistance characteristics comparable to those of conventional positive novolak photoresist compositions and can form a resist pattern with a high resolution and vertical sidewall profiles. This makes microprocessing possible.Type: GrantFiled: November 29, 1991Date of Patent: July 7, 1992Assignees: Oki Electric Industry Co., Ltd., Fuji Chemicals Industrial Co., Ltd.Inventors: Toshio Itoh, Miwa Sakata, Yoshio Yamashita, Takateru Asano, Yuuzi Kosuga, Hiroshi Umehara
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Patent number: 5066564Abstract: A photopolymerizable mixture is disclosed that comprises,a) a polymeric binder,b) an acrylate or alkacrylate of a polyhydric alcohol containing one or more urea groups and one or more urethane groups,c) a photoreducible dye as photoinitiator,d) a trihalomethyl compound which can be cleaved by irradiation, ande) an acridine or phenazine compound which is active as a photoinitiator.The mixture is suitable for the production of printing plates and photoresists and is distinguished by an increased shelf life.Type: GrantFiled: July 19, 1989Date of Patent: November 19, 1991Assignee: Hoechst AktiengesellschaftInventors: Rudolf Zertani, Dieter Mohr, Klaus Rode
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Patent number: 5057398Abstract: A photopolymerizable composition that contains a polymeric binder, a polymerizable compound and photoinitiator combination comprising an N-heterocyclic compound and a halogen compound corresponding to one of the folowing formulas I and II ##STR1## in which X.sup.1 stands for chlorine or bromine,X.sup.2 and X.sup.3 are identical or different and denote X.sup.1, hydrogen or alkyl groups,Y and Z are identical or different and denote X.sup.1, hydrogen, CN or (A).sub.n --(B).sub.n --D,A is a phenylene group,n is 0 or 1,B is CO or SO.sub.2,D is R, OR, NHR, NH.sub.2, NR.sub.2 or CX.sup.1 X.sup.2 X.sup.3,R is an alkyl, cycloalkyl, aryl or heteroyl radical,W is a five or six-membered heterocyclic ring having from 1 to 3 heteroatoms, which optionally carries substituents and optionally a fused aromatic ring, andm is 1 or 2,is distinguished by an improved light sensitivity.Type: GrantFiled: April 26, 1990Date of Patent: October 15, 1991Assignee: Hoechst AktiengesellschaftInventors: Hans-Dieter Frommeld, Hansjoerg Vollmann
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Patent number: 5034307Abstract: Titanocenes with, for example, .pi.-cyclopentadienyl ligands in which one or two carbo- or heterocyclic aromatic rings are bonded to the titanium, the aromatic rings being substituted by fluorine in at least one of the two ortho-positions relative to the metal-carbon bond and being substituted by at least one free or etherified or esterified polyoxaalkylene radical, are suitable as photoinitiators for the photopolymerization of ethylenically unsaturated substrates.Type: GrantFiled: August 21, 1990Date of Patent: July 23, 1991Assignee: Ciba-Geigy CorporationInventors: Martin Riediker, Eginhard Steiner, Harry Beyeler, Manfred Rembold, Francissek Sitek
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Patent number: 5030548Abstract: A photo-polymerizable composition is disclosed, which comprisesa thermoplastic polymeric binder;a non-gaseous ethylenically unsaturated compound;a photo-polymerization initiator system composed of 4,4'-bis(dialkylamino)benzophenone, aromatic ketone and lophine dimer;an organic halogen compound; and a leuco dye.Type: GrantFiled: August 10, 1989Date of Patent: July 9, 1991Assignee: Fuji Photo Film Co., Ltd.Inventors: Sadao Fujikura, Masayuki Iwasaki, Minoru Maeda, Minoru Wada
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Patent number: 4997745Abstract: A photosensitive composition comprising a trihalomethyl-s-triazine compound and a photosensitizer, wherein the photosensitizer being a dye having a reduction potential not more than 0.10 volt higher than the reduction potential of the trihalomethyl-s-triazine compound, and a photopolymerizable composition employing the photosensitive composition.Type: GrantFiled: August 11, 1989Date of Patent: March 5, 1991Assignee: Fuji Photo Film Co., Ltd.Inventors: Kouichi Kawamura, Hirotaka Matsumoto, Jun Yamaguchi
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Patent number: 4970136Abstract: Titanocenes with, for example, .pi.-cyclopentadienyl ligands in which one or two carbo- or heterocyclic aromatic rings are bonded to the titanium, the aromatic rings being substituted by fluorine in at least one of the two ortho-positions relative to the matal-carbon bond and being substituted by at least one free or etherified or esterified polyoxaalkylene radical, are suitable as photoinitiators for the photopolymerization of ethylenically unsaturated substrates.Type: GrantFiled: June 5, 1989Date of Patent: November 13, 1990Assignee: Ciba-Geigy CorporationInventors: Martin Riediker, Eginhard Steiner, Harry Beyeler, Manfred Rembold, Franciszek Sitek
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Patent number: 4963470Abstract: Titanocenes with silylated .pi.-cyclopentadienyl ligands in which one or two carbo- or heterocyclic aromatic rings are bonded to the titanium, the aromatic rings being substituted by fluorine, --CF.sub.3, --C.sub.2 F.sub.5, --CF.sub.2 CL or --CF.sub.2 CH.sub.3 in at least one of the two ortho-positions relative to the metal-carbon bonds, are suitable as photoinitiators for the photopolymerization of ethylenically unsaturated substrates. They are distinguished by a high sensitivity, stability to air and the action of heat, and a high activity in the region of UV light to visible light. They are furthermore readily soluble in the photopolymerizable compositions.Type: GrantFiled: January 19, 1990Date of Patent: October 16, 1990Assignee: Ciba-Geigy CorporationInventors: Bernd Klingert, Franciszek Sitek, Manfred Rembold
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Patent number: 4959297Abstract: Photopolymerizable compositions comprising:(1) at least one vinyl monomer capable of undergoing free radical polymerization,(2) a visible light or ultraviolet light responsive photoinitiator system comprising:(a) a diaryliodonium salt,(b) a pigment, insoluble in the photopolymerizable composition, said pigment also serving as a sensitizer,(c) one or more electron donating compounds, and, optionally,(3) adjuvants.The three component photoinitiator system of this invention can increase, by several orders of magnitude, the rate of ultraviolet light or visible light photocuring of vinyl monomers.Type: GrantFiled: November 22, 1989Date of Patent: September 25, 1990Assignee: Minnesota Mining and Manufacturing CompanyInventor: Michael C. Palazzotto
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Patent number: 4950581Abstract: A photopolymerizable composition is provided containing a polymerizable compound having an ethylenically unsaturated bond, a photopolymerization initiator, and if necessary, a linear organic high molecular weight polymer. The photopolymerization initiator comprises a combination of (a) an organic compound represented by formula (I): ##STR1## wherein R.sup.1, R.sup.2, R.sup.3, and R.sup.4, which may be the same or different, each represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted alkenyl group a substituted or unsubstituted alkynyl group, or a substituted or unsubstituted heterocyclic group, and at least two of said R.sup.1, R.sup.2, R.sup.3, and R.sup.4 may combine to form a cyclic structure, with the proviso that at least one of R.sup.1, R.sup.2, R.sup.3, and R.sup.4 is an alkyl group, and wherein Z.sym. represents an alkali metal cation or a quaternary ammonium cation, and (b) an organic dye having no counter anion.Type: GrantFiled: July 5, 1988Date of Patent: August 21, 1990Assignee: Fuji Photo Film Co., Ltd.Inventors: Mitsuru Koike, Nobuyuki Kita
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Patent number: 4946760Abstract: A radiation-sensitive mixture, in particular photosensitive mixture, is disclosed that contains a compound which forms a strong acid on exposure to actinic radiation and a polymeric reaction product of (i) a polymeric organic compound containing free OH groups, (ii) an organic compound containing at least two isocyanate groups or at least two epoxy groups, and (iii) a compound containing repeating acid-cleavable acetal or ketal groups and at least one free OH group. The mixture yields printing plates or photoresists with a longer storage life.Type: GrantFiled: November 1, 1988Date of Patent: August 7, 1990Assignee: Hoechst AktiengesellschaftInventor: Andreas Elsaesser
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Patent number: 4939069Abstract: Disclosed is a photopolymerizable composition which is very sensitive to light, especially visible light having a wave length of 600 to 700 nm. The photopolymerizable composition comprising a polymerizable compound having an ethylenically unsaturated double bond and a photopolymerization initiator wherein the photopolymerization initiator comprises (a) a specific sensitizer and (b) a radical forming agent.Type: GrantFiled: November 10, 1988Date of Patent: July 3, 1990Assignee: Nippon Paint Co., Ltd.Inventors: Masami Kawabata, Masahiko Harada, Yasuyuki Takimoto
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Patent number: 4927737Abstract: This invention relates to a radiation polymerizable composition for use in a photographic element such as a lithographic printing plate comprising in admixture(a) a binder resin having the general formula--A--B--C--wherein a plurality of each of components A, B and C occur in ordered or random sequence in the resin and wherein A is present in said resin at about 5% to about 20% by weight and comprises groups of the formula ##STR1## B is present in said resin at about 4% to about 30% by weight and comprises groups of the formula ##STR2## and C is present in said resin at about 50% to about 91% by weight and comprises acetal groups consisting of groups of the formulae ##STR3## where R is lower alkyl or hydrogen, and wherein said group I is present in component C from about 75% to about 85%, group II is present in component C from about 3% to about 5%; and group III is present in component C from about 10% to about 22%;(b) a photoinitiator; and(c) an acrylic monomer having one or more unsaturated groups.Type: GrantFiled: May 26, 1988Date of Patent: May 22, 1990Assignee: Hoechst Celanese CorporationInventors: John E. Walls, Carlos Tellechea, Major S. Dhillon
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Patent number: 4889792Abstract: Photopolymerizable compositions comprising:(1) at least one vinyl monomr capable of undergoing free radical polymerization,(2) a visible light or ultraviolet light responsive photoinitiator system comprising:(a) a diaryliodonium salt,(b) a pigment, insoluble in the photopolymerizable composition, said pigment also serving as a sensitizer,(c) one or more electron donating compounds, and, optionally,(3) adjuvants.The three component photoinitiator system of this invention can increase, by several orders of magnitude, the rate of ultraviolet light or visible light photocuring of vinyl monomers.Type: GrantFiled: December 9, 1987Date of Patent: December 26, 1989Assignee: Minnesota Mining and Manufacturing CompanyInventor: Michael C. Palazzotto
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Patent number: 4868092Abstract: Disclosed is a photopolymerizable composition which is very sensitive to visible light. The composition comprises a polymerizable compound and a photopolymerization initiator wherein the photopolymerization initiator comprises (A) a particular xanthene, coumarin or merocianine dyestuff, (B) a diaryliodonium salt and (C) a compound having the formula;R(n)--D--CH.sub.Type: GrantFiled: January 22, 1988Date of Patent: September 19, 1989Assignee: Nippon Paint Co., Ltd.Inventors: Masami Kawabata, Masahiko Harada, Yasuyuki Takimoto
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Patent number: 4842977Abstract: A light-sensitive material comprises a light-sensitive layer which contains silver halide, a reducing agent, a polymerizable compound and a base or base precursor provided on a support. The silver halide and polymerizable compound are contained in microcapsules to form light-sensitive microcapsules which are dispersed in the light-sensitive layer. The base or base precursor is contained in particles which are arranged outside of the light-sensitive microcapsules. At least 30% of the particles are adsorbed on the surface of the light-sensitive microcapsules.Type: GrantFiled: January 28, 1988Date of Patent: June 27, 1989Assignee: Fuji Photo Film Co., Ltd.Inventor: Fujio Kakimi
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Patent number: 4840869Abstract: Light sensitive compositions are disclosed which comprise 2-halomethyl-1,3,4,-oxadiazole compounds having a heterocyclic radical in the fifth position containing at least one element selected from the group consisting of oxygen, nitrogen, sulphur, and selenium directly or through a vinyl radical.Type: GrantFiled: August 10, 1987Date of Patent: June 20, 1989Assignee: Konishiroku Photo Industry Co., Ltd.Inventors: Noriyasu Kita, Kiyoshi Goto
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Patent number: 4837125Abstract: An electron-beam-sensitive resist material is provided that includes film having high-polymers and includes dopings. The material is made into a solution that is added to the substrate so that the resist material can be produced on the semiconductive or piezoelectric substrates by drying. The doping additives of the resist material can include: halogens, halogen compounds, peroxides, kaotropic salts and xanthates. The resist material is used for the production of electron-beam-written microstructures with high structural resolution and, in comparison to the known methods, eliminates the error-affected developing process.Type: GrantFiled: February 24, 1987Date of Patent: June 6, 1989Assignee: Siemens AktiengesellschaftInventors: Erwin Knapek, Helmut Formanek
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Patent number: 4816375Abstract: A photosolubilizable composition contains both a compound capable of producing an acid by irradiation with actinic rays and a compound which has at least one silyl ether or silyl ester group capable of being decomposed by an acid; optionally, a compound having at least one silyl ether group has at least one hydrophilic group, providing for increased solubility in a developing solution under the action of an acid, thus enhancing the photosensitivity and the development latitude of the composition.Type: GrantFiled: April 30, 1987Date of Patent: March 28, 1989Assignee: Fuji Photo Film Co., Ltd.Inventor: Toshiaki Aoai
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Patent number: 4800152Abstract: Heat stable, negative resist compositions are provided for use, particularly in deep ultraviolet light X-ray and electron beams. The composition comprises an acid generating onium salt photoinitiator, a source of polyfunctional activated aromatic rings and a source of polyfunctional carbonium ions, with at least one of said sources being a polymer.Type: GrantFiled: March 16, 1987Date of Patent: January 24, 1989Assignee: International Business Machines CorporationInventors: Robert D. Allen, Jean M. J. Frechet, Robert J. Twieg, Carlton G. Willson
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Patent number: 4791039Abstract: A visible ray-recording hologram material comprising a polymer containing a carbazole ring, iodoform, and an aromatic colorant having a fused ring system. This material enables recording with rays having a wavelength of 450 to 550 nm.Type: GrantFiled: February 13, 1987Date of Patent: December 13, 1988Assignee: Fujitsu LimitedInventors: Takeshi Ishitsuka, Yasuo Yamagishi, Akihiro Mochizuki
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Patent number: 4786577Abstract: A photo-solubilizable composition is disclosed, comprising (a) a compound capable of producing an acid upon being irradiated with actinic light rays, and (b) a compound containing at least one silyl ether group represented by formula (I) ##STR1## that is capable of being decomposed with an acid and at least one group selected from among a urethane group, a ureido group, an amido group, and an ester group, and, according to a preferred embodiment at least one hydrophilic group.Type: GrantFiled: December 12, 1985Date of Patent: November 22, 1988Assignee: Fuji Photo Film Co., Ltd.Inventors: Toshiaki Aoai, Akihiko Kamiya
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Patent number: 4774163Abstract: The present invention relates to a photopolymerizable composition which comprises(i) a monomer having at least one ethylenic unsaturated radical which is photopolymerizable under actinic light,(ii) at least one photopolymerizable initiator selected from the group consisting of compounds represented by the formula (I) ##STR1## wherein X represents a halogen atom and Y represents --CH.sub.3, --NH.sub.2, --NHR', --NR.sub.2, --OR' (wherein R' represents alkyl, substituted alkyl, aryl or substituted aryl and R represents --CX.sub.3, alkyl, substituted alkyl, aryl, substituted aryl or substituted alkenyl) and compounds represented by the formula (II) ##STR2## wherein X and R are the same as those of the formula (I) respectively, and(iii) a carbazole compound represented by the formula (III) ##STR3## wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.6, R.sub.7 and R.sub.Type: GrantFiled: March 11, 1987Date of Patent: September 27, 1988Assignee: Fuji Photo Film Co., Ltd.Inventor: Tatsuji Higashi
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Patent number: 4752552Abstract: A photosolubilizable composition contains both a compound capable of producing an acid by irradiation with actinic rays and a compound which has at least one silyl ether or silyl ester group capable of being decomposed by an acid; optionally, a compound having at least one silyl ether group has at least one hydrophilic group, providing for increased solubility in a developing solution under the action of an acid, thus enhancing the photosensitivity and the development latitude of the composition.Type: GrantFiled: August 12, 1987Date of Patent: June 21, 1988Assignee: Fuji Photo Film Co., Ltd.Inventor: Toshiaki Aoai
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Patent number: 4713401Abstract: Titanocenes with .pi.-cyclopentadienyl ligands, in which one or two carbocyclic or heterocyclic aromatic rings are bonded to the metal, the aromatic rings being substituted in at least one of the two ortho-positions relative to the metal-carbon bonds by CF.sub.2 Z (Z=F or substituted or unsubstituted alkyl), are suitable as photoinitiators for the photopolymerization of ethylenically unsaturated compounds. They are distinguished by a high radiation sensitivity, stability to air and thermal effects, and high effectiveness in the range from UV light to visible light.Type: GrantFiled: December 11, 1985Date of Patent: December 15, 1987Inventors: Martin Riediker, Kurt Meier, Hans Zweifel
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Patent number: 4707432Abstract: A free radical polymerizable composition comprising a free radical polymerizable material and a photoinitiator system therefor comprising appropriate amounts of an alpha-cleavage or homolytic bond cleavage, photoinitiator and a ferrocenium salt, said composition being suitable for use in the preparation of protective layers and photographic images.Type: GrantFiled: September 23, 1985Date of Patent: November 17, 1987Assignee: Ciba-Geigy CorporationInventors: Leslie R. Gatechair, Gary M. Blumenstein, Peter J. Schirmann
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Patent number: 4701399Abstract: A photosensitive composition containing a 2-halomethyl-5-substituted-1,3,4-oxadiazole compound represented by the following general formula (I): ##STR1## wherein A represents a substituted or unsubstituted aromatic residue; X represents a hydrogen atom, a cyano group, an alkyl group or an aryl group; Y represents a chlorine atom or a bromine atom; and n represents an integer of 1 to 3.The free radical generating agent represented by the general formula (I) has a photosensitive wavelength range from near ultraviolet range to visible range, high photo-decomposition sensitivity and good compatibility with other components present in the photosensitive composition.The photosensitive composition is suitable for use in light-sensitive printing plates or photo-resists.Type: GrantFiled: February 25, 1985Date of Patent: October 20, 1987Assignee: Fuji Photo Film Co., Ltd.Inventors: Teruo Nagano, Tadao Toyama, Akira Nagashima
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Patent number: 4698286Abstract: Disclosed are plasma developable photoresist compositions that possess photosensitivity to 436 n.m. light and maintain this photosensitivity for suitable periods of time after coating are obtainable. These compositions comprise perylene, certain perylene derivatives, or certain coumarin derivatives as photosensitizers in combination with N-vinyl monomers, haloalkene photoinitiators, and suitable polymeric binders in a suitable solvent.Type: GrantFiled: June 3, 1985Date of Patent: October 6, 1987Assignee: Hercules IncorporatedInventor: Wayne R. Messer
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Patent number: 4696888Abstract: Light-sensitive compounds are described which have the formula ##STR1## wherein R.sup.1 and R.sup.2 denote H or alkyl, R.sup.3 and R.sup.4 denote H or 4,6-bis-trichloromethyl-s-triazin-2-yl, R.sup.5 and R.sup.6 denote H or halogen, alkyl, alkenyl or alkoxy, and Ar denotes a mononuclear to trinuclear aromatic group.These compounds are suitable as photoinitiators for free-radical polymerizations or as photolytic acid donors for acid-cleavable compounds, and for cross-linking and color formation reactions. They are distinguished by a high sensitivity in various spectral ranges.Type: GrantFiled: July 30, 1986Date of Patent: September 29, 1987Assignee: Hoechst AktiengesellschaftInventor: Gerhard Buhr
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Patent number: 4689288Abstract: Photosensitive film which is photosensitive in a given wavelength range comprises at least one silicon-containing polymer, at least one salt which can be converted into a Brunsted acid by irradiation and optionally at least one photosensitizer. The silicon-containing polymer-based photosensitive film can be used as a masking resin in a lithography process for producing electronic components.Type: GrantFiled: September 19, 1985Date of Patent: August 25, 1987Assignee: Commissariat a l'Energie AtomiqueInventors: Francois Buiguez, Louis Giral, Charles Rosilio, Francois Schue
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Patent number: 4689289Abstract: Block polymer compositions are provided which are useful as positive or negative resists utilizing aryl onium salts in combination with silicone-organic block polymers, such as polydimethylsiloxane-poly-t-butylmethacrylate block polymers. A silicone prepolymer is used in combination with certain polymerizable vinyl monomers such as t-butylmethacrylate. The silicone prepolymer has chemically combined pinacolate groups in the backbone or terminal positions which are capable of generating free-radicals upon thermolysis.Type: GrantFiled: April 30, 1986Date of Patent: August 25, 1987Assignee: General Electric CompanyInventor: James V. Crivello
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Patent number: 4665006Abstract: A photoresist composition comprised of a radiation scissionable polymeric system having organopolysiloxane segments sensitized by an onium salt is disclosed. Useful organopolysiloxane containing polymers include polysiloxane-polycarbonate block copolymers, and polyorganosiloxane polyaryl esters. The resist films produced from the photoresist compositions exhibit high sensitivity, high thermal stability and resistance to oxygen reactive ion etching which makes them desirable for dry etching processes to enable submicron resolution.Type: GrantFiled: December 9, 1985Date of Patent: May 12, 1987Assignee: International Business Machines CorporationInventors: Krishna G. Sachdev, Ranee W. Kwong, Mahmoud M. Khojasteh, Harbans S. Sachdev
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Patent number: 4661434Abstract: A photopolymerizable composition comprising (A) an addition-polymerizable unsaturated compound having two or more ethylenically unsaturated double bonds and (B) a ternary photopolymerization initiator system, comprising a combination of a 4,4'-bis(dialkylamino)benzophenone represented by the following general formula (I), a carbonyl compound represented by the following general formula (IIa) or (IIb), and a compound having a group represented by the following general formula (III): ##STR1## wherein each R, which may be the same or different, represents an alkyl group, a cycloalkyl group or a hydroxyalkyl group, or may be bonded to another R substituent of the same nitrogen atom to form a tetramethylene group, a pentamethylene group or an oxybisethylene group; ##STR2## wherein X represents a single bond, an oxygen atom, a sulfur atom, a substituted or unsubstituted nitrogen atom or a carbonyl group, R.sup.1 and R.sup.Type: GrantFiled: August 16, 1984Date of Patent: April 28, 1987Assignee: Fuji Photo Film Co., Ltd.Inventors: Masayuki Iwasaki, Minoru Maeda, Fumiaki Shinozaki
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Patent number: 4659649Abstract: The invention provides new compositions which change color on exposure to actinic radiation and contain a photosensitive onium, e.g. iodonium or sulphonium, salt and a dyestuff which changes color when protonated. The compositions may also include a resin, especially a resin curable by the onium salt when the latter is exposed, and preferably an epoxy resin. The compositions are useful especially as coatings, e.g. for making screen stencils or for producing lithographic printing plates.Type: GrantFiled: April 30, 1984Date of Patent: April 21, 1987Assignee: Sericol Group LimitedInventors: Peter Dickinson, Michael Ellwood
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Patent number: 4657844Abstract: A negative resist composition including a polymeric matrix material, a polymerizable monomer, and an onium salt radiation sensitive initiator. The monomer is polymerized by irradiating the resist with an e-beam, x-ray, or ultraviolet source and heating the exposed resist. The resist is developed by a dry etchant such as plasma or a reactive ion etchant.Type: GrantFiled: May 14, 1985Date of Patent: April 14, 1987Assignee: Texas Instruments IncorporatedInventors: Jing S. Shu, Johnny B. Covington, Wei Lee, Larry G. Venable, Gilbert L. Varnell
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Patent number: 4631247Abstract: Disclosed are shelf life improvers for photoresist compositions containing organic halides as the photoinitiator that comprise an acetylene compound having the general formula RC.tbd.CR' where R and R' are each independently phenyl, hydrogen, benzyl, vinyl, lower alkyl substituted vinyl, phenyl substituted vinyl, lower alkoxy methyl and phenoxymethyl.Type: GrantFiled: August 9, 1985Date of Patent: December 23, 1986Assignee: Hercules IncorporatedInventor: Frank P. Tise
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Patent number: 4610952Abstract: Water soluble blends are provided of alkanolacrylamide, water soluble hydroxyl containing film forming organic oligomer and an effective amount of an onium salt photoinitiator. These photocurable compositions can be used as photoresists.Type: GrantFiled: April 22, 1985Date of Patent: September 9, 1986Assignee: General Electric CompanyInventor: James V. Crivello
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Patent number: 4590146Abstract: Photopolymerizable water-soluble or water-dispersible mixtures essentially consisting of a base polymer, at least one polymerizable ethylenically unsaturated compound and at least one photoinitiator and/or photosensitizer are stabilized to thermal polymerization by treating the base polymer with a halogen, a pseudohalogen or a polyhalide.Type: GrantFiled: July 6, 1984Date of Patent: May 20, 1986Assignee: BASF AktiengesellschaftInventor: Guenter Wallbillich
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Patent number: 4584260Abstract: A photopolymerizable composition comprising an addition polymerizable unsaturated compound containing at least two ethylenically unsaturated double bonds in the molecule thereof and photopolymerization initiators, wherein a 4,4'-bis(dialkylamino)benzophenone represented by general formula I below, a benzophenone derivative represented by general formula II below and a compound having a group represented by general formula III below are contained as said photopolymerization initiators: ##STR1## wherein R represents an alkyl, cycloalkyl or hydroxyalkyl group having 1 to 6 carbon atoms or is combined with another R substituted on the same nitrogen atom to form tetramethylene, pentamethylene or oxybisethylene; ##STR2## wherein R.sup.1 represents a hydrogen atom ##STR3## X.sub.1 and X.sub.2 each represents an alkyl group, an alkoxy group, a carboxy group, an alkoxycarbonyl group, an aryloxycarbonyl group or a halogen atom; m and n each represents 0, 1 or 2 and when m and n each represents 2, X.sub.1 and X.sub.Type: GrantFiled: June 6, 1985Date of Patent: April 22, 1986Assignee: Fuji Photo Film Co., Ltd.Inventors: Masayuki Iwasaki, Minoru Maeda, Fumiaki Shinozaki
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Patent number: 4571377Abstract: Disclosed is a photopolymerizable vehicle and method for the selective photopolymerization of said vehicle by the application of a plurality of different selected wavelengths of energy wherein any single wavelength of energy is inadequate for effecting said photopolymerization. The method comprises sequentially applying a plurality of different selected wavelengths of energy to said vehicle whereby polymerization is effected at the intersection of said wavelengths of energy.Type: GrantFiled: January 23, 1984Date of Patent: February 18, 1986Assignee: Battelle Memorial InstituteInventors: Vincent D. McGinniss, Robert E. Schwerzel
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Patent number: 4548890Abstract: Aqueous dispersions comprising water, a cationically curable compound, and a photosensitive onium salt, and preferably other ingredients such as sensitizers, fillers, and plasticizers, are useful for making printing screens, lithographic plates, and printed circuit resists. After exposure, the un-cured composition is easily removed by washing with water.Type: GrantFiled: March 30, 1984Date of Patent: October 22, 1985Assignee: Sericol Group LimitedInventors: Peter Dickinson, Michael Ellwood
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Patent number: 4548891Abstract: The invention relates to photopolymerizable compositions comprising (a) a prepolymer containing photopolymerizable olefinic double bonds, (b) photoinitiator of the formula ##STR1## wherein R.sup.1, R.sup.2 and R.sup.3 are as defined in claim 1, and optionally (c) an ester of acrylic or methacrylic acid or an allyl ether or allyl ester of a polyol.Owing to their excellent light sensitivity, these compositions are suitable for the economic production of high temperature resistant protective layers and relief structures having excellent resolution and good contours.Type: GrantFiled: February 2, 1984Date of Patent: October 22, 1985Assignee: Ciba Geigy CorporationInventors: Martin Riediker, Ottmar Rohde, Martin Roth, Niklaus Buhler
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Patent number: 4548892Abstract: A photopolymerizable composition is described, containing an addition polymerizable, unsaturated compound having two or more ethylenically unsaturated double bonds within the molecule and a photopolymerization initiator, wherein said photopolymerization initiator is an acylhaloacetic acid amide derivative represented by formula (I) ##STR1## wherein Ar represents a substituted or unsubstituted aryl group, X represents a carbonyl or sulfonyl group, Y represents a chlorine atom or a bromine atom, R represents a hydrogen atom, a chlorine atom or a bromine atom, and R.sup.a and R.sup.b each represents a hydrogen atom, a substituted or unsubstituted alkyl group, an aryl group, or an aralkyl group.Type: GrantFiled: January 29, 1985Date of Patent: October 22, 1985Assignee: Fuji Photo Film Co., Ltd.Inventors: Masayuki Iwasaki, Minoru Maeda, Fumiaki Shinozaki, Kouichi Kawamura
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Patent number: 4537854Abstract: Water soluble blends are provided of alkanolacrylamide, water soluble hydroxyl containing film forming organic oligomer and an effective amount of an onium salt photoinitiator. These photocurable compositions can be used as photoresists.Type: GrantFiled: September 14, 1983Date of Patent: August 27, 1985Assignee: General Electric CompanyInventor: James V. Crivello
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Patent number: 4535052Abstract: Photopolymerizable compositions comprising(a) at least one ethylenically unsaturated compound,(b) at least one organic polymeric binder,(c) optionally at least one photoinitiator and(d) at least one constrained N-alkylamino aryl ketone compound as defined, e.g., bis(9-julolidyl ketone), bis-(N-ethyl-1,2,3,4-tetrahydro-6-quinolyl)ketone, etc. The compositions, in layer form, are useful in photoresists, including projection speed photoresists, printing plates, drafting and toning films, etc.Type: GrantFiled: August 28, 1984Date of Patent: August 13, 1985Assignee: E. I. Du Pont de Nemours and CompanyInventors: Albert G. Anderson, Thomas E. Dueber