Halogen Compound Containing Patents (Class 430/925)
  • Patent number: 5272042
    Abstract: 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: Grant
    Filed: September 17, 1991
    Date of Patent: December 21, 1993
    Assignee: International Business Machines Corporation
    Inventors: 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
  • Patent number: 5219700
    Abstract: 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: Grant
    Filed: March 24, 1992
    Date of Patent: June 15, 1993
    Assignees: Mitsubishi Kasei Corporation, Konica Corporation
    Inventors: Hideyuki Nakai, Kiyoshi Goto, Hiroshi Tomiyasu, Yoshiko Fujita
  • Patent number: 5212046
    Abstract: 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: Grant
    Filed: June 28, 1991
    Date of Patent: May 18, 1993
    Assignee: Shipley Company Inc.
    Inventors: Angelo A. Lamola, Gary Calabrese, Roger Sinta
  • Patent number: 5141841
    Abstract: 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: Grant
    Filed: August 17, 1989
    Date of Patent: August 25, 1992
    Assignee: Vickers PLC
    Inventor: John R. Wade
  • Patent number: 5141840
    Abstract: 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: Grant
    Filed: January 29, 1991
    Date of Patent: August 25, 1992
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Kazuyoshi Mizutani, Toshiaki Aoai
  • Patent number: 5128231
    Abstract: 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: Grant
    Filed: November 29, 1991
    Date of Patent: July 7, 1992
    Assignees: Oki Electric Industry Co., Ltd., Fuji Chemicals Industrial Co., Ltd.
    Inventors: Toshio Itoh, Miwa Sakata, Yoshio Yamashita, Takateru Asano, Yuuzi Kosuga, Hiroshi Umehara
  • Patent number: 5066564
    Abstract: 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: Grant
    Filed: July 19, 1989
    Date of Patent: November 19, 1991
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Rudolf Zertani, Dieter Mohr, Klaus Rode
  • Patent number: 5057398
    Abstract: 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: Grant
    Filed: April 26, 1990
    Date of Patent: October 15, 1991
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Hans-Dieter Frommeld, Hansjoerg Vollmann
  • Patent number: 5034307
    Abstract: 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: Grant
    Filed: August 21, 1990
    Date of Patent: July 23, 1991
    Assignee: Ciba-Geigy Corporation
    Inventors: Martin Riediker, Eginhard Steiner, Harry Beyeler, Manfred Rembold, Francissek Sitek
  • Patent number: 5030548
    Abstract: 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: Grant
    Filed: August 10, 1989
    Date of Patent: July 9, 1991
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Sadao Fujikura, Masayuki Iwasaki, Minoru Maeda, Minoru Wada
  • Patent number: 4997745
    Abstract: 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: Grant
    Filed: August 11, 1989
    Date of Patent: March 5, 1991
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Kouichi Kawamura, Hirotaka Matsumoto, Jun Yamaguchi
  • Patent number: 4970136
    Abstract: 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: Grant
    Filed: June 5, 1989
    Date of Patent: November 13, 1990
    Assignee: Ciba-Geigy Corporation
    Inventors: Martin Riediker, Eginhard Steiner, Harry Beyeler, Manfred Rembold, Franciszek Sitek
  • Patent number: 4963470
    Abstract: 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: Grant
    Filed: January 19, 1990
    Date of Patent: October 16, 1990
    Assignee: Ciba-Geigy Corporation
    Inventors: Bernd Klingert, Franciszek Sitek, Manfred Rembold
  • Patent number: 4959297
    Abstract: 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: Grant
    Filed: November 22, 1989
    Date of Patent: September 25, 1990
    Assignee: Minnesota Mining and Manufacturing Company
    Inventor: Michael C. Palazzotto
  • Patent number: 4950581
    Abstract: 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: Grant
    Filed: July 5, 1988
    Date of Patent: August 21, 1990
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Mitsuru Koike, Nobuyuki Kita
  • Patent number: 4946760
    Abstract: 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: Grant
    Filed: November 1, 1988
    Date of Patent: August 7, 1990
    Assignee: Hoechst Aktiengesellschaft
    Inventor: Andreas Elsaesser
  • Patent number: 4939069
    Abstract: 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: Grant
    Filed: November 10, 1988
    Date of Patent: July 3, 1990
    Assignee: Nippon Paint Co., Ltd.
    Inventors: Masami Kawabata, Masahiko Harada, Yasuyuki Takimoto
  • Patent number: 4927737
    Abstract: 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: Grant
    Filed: May 26, 1988
    Date of Patent: May 22, 1990
    Assignee: Hoechst Celanese Corporation
    Inventors: John E. Walls, Carlos Tellechea, Major S. Dhillon
  • Patent number: 4889792
    Abstract: 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: Grant
    Filed: December 9, 1987
    Date of Patent: December 26, 1989
    Assignee: Minnesota Mining and Manufacturing Company
    Inventor: Michael C. Palazzotto
  • Patent number: 4868092
    Abstract: 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: Grant
    Filed: January 22, 1988
    Date of Patent: September 19, 1989
    Assignee: Nippon Paint Co., Ltd.
    Inventors: Masami Kawabata, Masahiko Harada, Yasuyuki Takimoto
  • Patent number: 4842977
    Abstract: 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: Grant
    Filed: January 28, 1988
    Date of Patent: June 27, 1989
    Assignee: Fuji Photo Film Co., Ltd.
    Inventor: Fujio Kakimi
  • Patent number: 4840869
    Abstract: 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: Grant
    Filed: August 10, 1987
    Date of Patent: June 20, 1989
    Assignee: Konishiroku Photo Industry Co., Ltd.
    Inventors: Noriyasu Kita, Kiyoshi Goto
  • Patent number: 4837125
    Abstract: 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: Grant
    Filed: February 24, 1987
    Date of Patent: June 6, 1989
    Assignee: Siemens Aktiengesellschaft
    Inventors: Erwin Knapek, Helmut Formanek
  • Patent number: 4816375
    Abstract: 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: Grant
    Filed: April 30, 1987
    Date of Patent: March 28, 1989
    Assignee: Fuji Photo Film Co., Ltd.
    Inventor: Toshiaki Aoai
  • Patent number: 4800152
    Abstract: 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: Grant
    Filed: March 16, 1987
    Date of Patent: January 24, 1989
    Assignee: International Business Machines Corporation
    Inventors: Robert D. Allen, Jean M. J. Frechet, Robert J. Twieg, Carlton G. Willson
  • Patent number: 4791039
    Abstract: 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: Grant
    Filed: February 13, 1987
    Date of Patent: December 13, 1988
    Assignee: Fujitsu Limited
    Inventors: Takeshi Ishitsuka, Yasuo Yamagishi, Akihiro Mochizuki
  • Patent number: 4786577
    Abstract: 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: Grant
    Filed: December 12, 1985
    Date of Patent: November 22, 1988
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Toshiaki Aoai, Akihiko Kamiya
  • Patent number: 4774163
    Abstract: 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: Grant
    Filed: March 11, 1987
    Date of Patent: September 27, 1988
    Assignee: Fuji Photo Film Co., Ltd.
    Inventor: Tatsuji Higashi
  • Patent number: 4752552
    Abstract: 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: Grant
    Filed: August 12, 1987
    Date of Patent: June 21, 1988
    Assignee: Fuji Photo Film Co., Ltd.
    Inventor: Toshiaki Aoai
  • Patent number: 4713401
    Abstract: 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: Grant
    Filed: December 11, 1985
    Date of Patent: December 15, 1987
    Inventors: Martin Riediker, Kurt Meier, Hans Zweifel
  • Patent number: 4707432
    Abstract: 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: Grant
    Filed: September 23, 1985
    Date of Patent: November 17, 1987
    Assignee: Ciba-Geigy Corporation
    Inventors: Leslie R. Gatechair, Gary M. Blumenstein, Peter J. Schirmann
  • Patent number: 4701399
    Abstract: 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: Grant
    Filed: February 25, 1985
    Date of Patent: October 20, 1987
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Teruo Nagano, Tadao Toyama, Akira Nagashima
  • Patent number: 4698286
    Abstract: 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: Grant
    Filed: June 3, 1985
    Date of Patent: October 6, 1987
    Assignee: Hercules Incorporated
    Inventor: Wayne R. Messer
  • Patent number: 4696888
    Abstract: 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: Grant
    Filed: July 30, 1986
    Date of Patent: September 29, 1987
    Assignee: Hoechst Aktiengesellschaft
    Inventor: Gerhard Buhr
  • Patent number: 4689288
    Abstract: 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: Grant
    Filed: September 19, 1985
    Date of Patent: August 25, 1987
    Assignee: Commissariat a l'Energie Atomique
    Inventors: Francois Buiguez, Louis Giral, Charles Rosilio, Francois Schue
  • Patent number: 4689289
    Abstract: 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: Grant
    Filed: April 30, 1986
    Date of Patent: August 25, 1987
    Assignee: General Electric Company
    Inventor: James V. Crivello
  • Patent number: 4665006
    Abstract: 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: Grant
    Filed: December 9, 1985
    Date of Patent: May 12, 1987
    Assignee: International Business Machines Corporation
    Inventors: Krishna G. Sachdev, Ranee W. Kwong, Mahmoud M. Khojasteh, Harbans S. Sachdev
  • Patent number: 4661434
    Abstract: 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: Grant
    Filed: August 16, 1984
    Date of Patent: April 28, 1987
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Masayuki Iwasaki, Minoru Maeda, Fumiaki Shinozaki
  • Patent number: 4659649
    Abstract: 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: Grant
    Filed: April 30, 1984
    Date of Patent: April 21, 1987
    Assignee: Sericol Group Limited
    Inventors: Peter Dickinson, Michael Ellwood
  • Patent number: 4657844
    Abstract: 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: Grant
    Filed: May 14, 1985
    Date of Patent: April 14, 1987
    Assignee: Texas Instruments Incorporated
    Inventors: Jing S. Shu, Johnny B. Covington, Wei Lee, Larry G. Venable, Gilbert L. Varnell
  • Patent number: 4631247
    Abstract: 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: Grant
    Filed: August 9, 1985
    Date of Patent: December 23, 1986
    Assignee: Hercules Incorporated
    Inventor: Frank P. Tise
  • Patent number: 4610952
    Abstract: 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: Grant
    Filed: April 22, 1985
    Date of Patent: September 9, 1986
    Assignee: General Electric Company
    Inventor: James V. Crivello
  • Patent number: 4590146
    Abstract: 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: Grant
    Filed: July 6, 1984
    Date of Patent: May 20, 1986
    Assignee: BASF Aktiengesellschaft
    Inventor: Guenter Wallbillich
  • Patent number: 4584260
    Abstract: 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: Grant
    Filed: June 6, 1985
    Date of Patent: April 22, 1986
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Masayuki Iwasaki, Minoru Maeda, Fumiaki Shinozaki
  • Patent number: 4571377
    Abstract: 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: Grant
    Filed: January 23, 1984
    Date of Patent: February 18, 1986
    Assignee: Battelle Memorial Institute
    Inventors: Vincent D. McGinniss, Robert E. Schwerzel
  • Patent number: 4548890
    Abstract: 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: Grant
    Filed: March 30, 1984
    Date of Patent: October 22, 1985
    Assignee: Sericol Group Limited
    Inventors: Peter Dickinson, Michael Ellwood
  • Patent number: 4548891
    Abstract: 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: Grant
    Filed: February 2, 1984
    Date of Patent: October 22, 1985
    Assignee: Ciba Geigy Corporation
    Inventors: Martin Riediker, Ottmar Rohde, Martin Roth, Niklaus Buhler
  • Patent number: 4548892
    Abstract: 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: Grant
    Filed: January 29, 1985
    Date of Patent: October 22, 1985
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Masayuki Iwasaki, Minoru Maeda, Fumiaki Shinozaki, Kouichi Kawamura
  • Patent number: 4537854
    Abstract: 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: Grant
    Filed: September 14, 1983
    Date of Patent: August 27, 1985
    Assignee: General Electric Company
    Inventor: James V. Crivello
  • Patent number: 4535052
    Abstract: 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: Grant
    Filed: August 28, 1984
    Date of Patent: August 13, 1985
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Albert G. Anderson, Thomas E. Dueber