Carbonyl Compound Containing Patents (Class 430/923)
-
Patent number: 6692891Abstract: The present invention relates to a photoresist composition containing a photo radical generator, more specifically, to a photoresist composition which comprises (a) photoresist resin, (b) a photoacid generator, (c) an organic solvent and (d) a photo radical generator. The present photoresist composition reduces or prevents a sloping pattern formation due to a higher concentration of acid in the upper portion of the photoresist relative to the lower portion of the photoresist.Type: GrantFiled: June 12, 2001Date of Patent: February 17, 2004Assignee: Hynix Semiconductor IncInventors: Jae Chang Jung, Geun Su Lee, Min Ho Jung, Ki Ho Baik
-
Publication number: 20040013977Abstract: A liquid radiation-curable composition that comprisesType: ApplicationFiled: January 7, 2003Publication date: January 22, 2004Applicant: 3D Systems, Inc.Inventor: Bettina Steinmann
-
Publication number: 20030215745Abstract: A process for producing a polymer compound having a double bond in a side chain, wherein a functional group represented by the following formula (1) is subjected to an elimination reaction to form the polymer compound which includes another functional group having the double bond in the side chain thereof represented by the following formula (2): 1Type: ApplicationFiled: March 11, 2003Publication date: November 20, 2003Applicant: FUJI PHOTO FILM CO., LTD.Inventor: Kazuhiro Fujimaki
-
Publication number: 20030194641Abstract: A positive resist composition comprising (A) a resin, which is decomposed by the action of an acid to increase solubility in an alkali developing solution, having a repeating unit represented by formula (Y) defined in the specification, (B) a compound capable of generating an acid upon irradiation of an actinic ray or radiation, and (C) a solvent.Type: ApplicationFiled: February 25, 2003Publication date: October 16, 2003Applicant: FUJI PHOTO FILM CO., LTD.Inventors: Kazuyoshi Mizutani, Tomoya Sasaki, Shinichi Kanna
-
Publication number: 20030190554Abstract: A plate-making method of a printing plate comprising exposing a printing plate precursor having a photosensitive layer comprising a photopolymerizable composition containing (i) a crosslinking agent having two ethylenic polymerizable groups and (ii) a crosslinking agent having three or more ethylenic polymerizable groups, and development processing the exposed printing plate precursor with an alkali developer having a pH of not more than 12.5.Type: ApplicationFiled: August 29, 2002Publication date: October 9, 2003Inventor: Kazuto Kunita
-
Publication number: 20030118939Abstract: The present invention provides an IR-sensitive composition, which includes: a polymeric binder; and a free radical polymerizable system consisting of: at least one component selected from unsaturated free radical polymerizable monomers, oligomers which are free radical polymerizable and polymers containing C═C bonds in the backbone and/or in the side chain groups; and an initiator system, which includes: (a) at least one compound capable of absorbing IR radiation; (b) at least one compound capable of producing radicals; and (c) at least one carboxylic co-initiator, provided that the total acid number of the polymeric binder is 70 mg KOH/g or less. The present invention further provides a printing plate precursor, a process for preparing the printing plate and a method of producing an image.Type: ApplicationFiled: November 9, 2001Publication date: June 26, 2003Applicant: KODAK POLYCHROME GRAPHICS, L.L.C.Inventors: Heidi Munnelly, Paul West
-
Patent number: 6579663Abstract: Compounds of the formula I R1 and R2 independently of one another are C1-C20alkyl, OR11, CF3 or halogen; R3, R4 and R5 independently of one another are hydrogen, C1-C20alkyl, OR11 or halogen; R6, R7, R8, R9 and R10 independently of one another are hydrogen, C1-C20alkyl; C2-C20alkyl which is interrupted once or more than once by nonconsecutive O atoms and which is unsubstituted or substituted by OH and/or SH; or R6, R7, R8, R9 and R10 are OR11, SR11, N(R12)(R13), phenyl or halogen; R11 is C1-C20alkyl, C3-C8cycloalkyl, phenyl, benzyl or C2-C20alkyl which is interrupted once or more than once by O or S and which is unsubstituted or substituted by OH and/or SH; R12 and R13 independently of one another are hydrogen, C114 C20alkyl, C3-C8cycloalkyl, phenyl, benzyl or C2-C20alkyl which is interrupted once or more than once by nonconsecutive O atoms and which is unsubstituted or substituted by OH and/or SH; or R12 and R13 together are C3-C5alkylene which can be interrupted by O, S or NR14; R14 is hydType: GrantFiled: October 22, 2001Date of Patent: June 17, 2003Assignee: Ciba Specialty Chemicals CorporationInventors: Jean-Pierre Wolf, Beat Michael Aebli, Gebhard Hug
-
Patent number: 6576393Abstract: Disclosed are a composition for a resist underlayer film excellent in reproducibility of a resist pattern, excellent in adhesion to a resist, excellent in resistance to a developing solution used after exposure of the resist and decreased in film loss in oxygen ashing of the resist; and a method for producing the same, the composition comprising: both or either of a hydrolysate and a condensate of (A) at least one compound selected from the group consisting of (A-1) a compound represented by the following general formula (1): R1aSi(OR2)4−a (1) wherein R1 represents a hydrogen atom, a fluorine atom or a univalent organic group, R2 represents a univalent organic group, and a represents an integer of 0 to 2, and (A-2) a compound represented by the following general formula (2): R3b(R4O)3−bSi—(R7)d—Si(OR5)3−cR6c (2) wherein R3, R4, R5 and R6, which may be the same or different, each represent univalent organic groups, b and c, which may be the same or diffeType: GrantFiled: April 7, 2000Date of Patent: June 10, 2003Assignee: JSR CorporationInventors: Hikaru Sugita, Akio Saito, Kinji Yamada, Michinori Nishikawa, Yoshihisa Ohta, Yoshiji Yuumoto
-
Patent number: 6551761Abstract: This invention relates to &agr;-ammonium ketones, iminium ketones or amidinium ketones in the form of their tetraaryl- or triarylalkylborate salts which can be photochemically converted into amines, imines or amidines as well as to a process for their preparation. This invention also relates to base-polymerisable or crosslinkable compositions comprising these &agr;-ammonium ketones, iminium ketones or amidinium ketones in the form of their tetra- or triarylalkylborate salts, to a process for carrying out photochemically induced, base-catalysed reactions as well as to their use as photoinitiators for base-catalysed reactions.Type: GrantFiled: September 7, 2000Date of Patent: April 22, 2003Assignee: Ciba Specialty Chemical CorporationInventors: Véronique Hall-Goulle, Sean Colm Turner, Allan Francis Cunningham
-
Publication number: 20020168584Abstract: A positive resist composition comprises: (A) a resin capable of decomposing by the action of an acid to increase the solubility in an alkali developer; and (B) a compound capable of generating an acid upon irradiation with one of an actinic ray and a radiation, wherein the resin (A) contains a specified repeating unit.Type: ApplicationFiled: March 19, 2002Publication date: November 14, 2002Applicant: FUJI PHOTO FILM CO., LTD.Inventors: Toshiaki Aoai, Kazuyoshi Mizutani, Shinichi Kanna
-
Publication number: 20020106582Abstract: A photosensitive composition suitable for practical waveguide devices is provided. The photosensitive composition comprises at least one multifunctional acrylate prepared from a fluorinated multifunctional alcohol and at least one photoinitiator. The said composition has high photo contrast, high curing speed, controllable refractive index, low curing shrinkage, high thermo-optic coefficient, low volatility and high viscosity. A waveguide device is formed by patterning the photosensitive composition.Type: ApplicationFiled: January 18, 2002Publication date: August 8, 2002Inventors: Chuck C. Xu, Deepti Pant, Chris E. Osuch, Louay A. Eldada
-
Patent number: 6372406Abstract: Deactivated aromatic amines are useful to improve shelf life and performance of acid-catalyzed photoresist compositions without adverse interaction with radiation-sensitive acid generator components in said resist. The compositions are especially useful in photolithography processes used in forming integrated circuits and other miniaturized components.Type: GrantFiled: November 6, 2000Date of Patent: April 16, 2002Assignee: International Business Machines CorporationInventors: William R. Brunsvold, Ahmad D. Katnani, Pushkara R. Varanasi
-
Patent number: 6342334Abstract: Provided is a chemically amplified resist composition comprising a photoacid generator which releases, by exposure to light, an acid containing both a sulfonic acid group and a carboxyl group; and an acid sensitive resin which contains a dissolution controlling group to be cleaved therefrom by the action of the acid, thereby forming a carboxy-containing alkali soluble resin; or a chemically amplified resist composition comprising a photoacid generator and an acid sensitive resin which has a huge molecular weight and from which the dissolution controlling group is cleaved owing to the decomposition of the partially crosslinked structure by the acid released from the photoacid generator. By the above-described composition, ultrafine processing can be carried out with improved focal depth, whereby an excellent rectangular pattern can be formed.Type: GrantFiled: May 18, 2000Date of Patent: January 29, 2002Assignee: NEC CorporationInventor: Mitsuharu Yamana
-
Patent number: 6287749Abstract: Biradical initiators and methods using the same are disclosed. Polymerization of compositions which include the compounds of the invention may be activated by irradiating the composition with radiation.Type: GrantFiled: May 4, 1998Date of Patent: September 11, 2001Assignees: First Chemical Corporation, Univ. of Southern MississippiInventors: Rajamani Nagarajan, Joseph Stanton Bowers, Jr., Charles E. Hoyle, E. Sonny Jönsson, John R. I. Eubanks
-
Patent number: 6284430Abstract: Disclosed is a novel positive-working chemical-amplification photoresist composition capable of giving an extremely finely patterned resist layer in the manufacturing process of semiconductor devices and a method for forming a finely patterned resist layer therewith. The photoresist composition comprises: (A) 100 parts by weight of a copolymeric resin consisting of from 50 to 85% by moles of (a) hydroxyl group-containing styrene units, from 15 to 35% by moles of (b) styrene units and from 2 to 20% by moles of (c) tert-butyl (meth)acrylate units; and (B) from 1 to 20 parts by weight of a radiation-sensitive acid-generating agent which is an onium salt containing a fluoroalkyl sulfonate ion having 1 to 10 carbon atoms as the anion such as diphenyliodonium trifluoromethane sulfonate.Type: GrantFiled: September 7, 2000Date of Patent: September 4, 2001Assignee: Tokyo Ohka Kogyo Co., Ltd.Inventors: Katsumi Oomori, Hiroto Yukawa, Ryusuke Uchida, Kazufumi Sato
-
Patent number: 6280905Abstract: A photosensitive resin composition which comprises (1) a particulate copolymer comprising 10-99.8% by mole of the unit of (i) an aliphatic conjugated diene monomer, 0.1-30% by mole of the unit of (ii) a monomer having one polymerizable unsaturated group and an amino group, 0.1-20% by mole of the unit of (iii) a monomer having at least two polymerizable unsaturated groups and 0-40% by mole of the unit of (iv) a copolymerizable other monomer having one polymerizable unsaturated group, (2) a photopolymerizable unsaturated monomer and (3) a photopolymerization initiator typically represented by 9-fluorenone or 2-i-propylthioxanthone. A photosensitive resin composition is provided which can be developed by using water, has a low hardness and high resilience, and is excellent in balance of properties.Type: GrantFiled: April 21, 2000Date of Patent: August 28, 2001Assignee: JSR CorporationInventors: Katsuo Koshimura, Tsukasa Toyoshima, Takashi Nishioka, Tadaaki Tanaka
-
Patent number: 6261736Abstract: The pattern forming material of the present invention includes a polymer having a group which generates an acid when the polymer is irradiated with an energy beam or heated and a compound which generates a base when the compound is irradiated with an energy beam. The polymer is a binary polymer or a polymer of a higher degree obtained by polymerizing another group with a compound represented by the following general formula: where R1 indicates a hydrogen atom or an alkyl group, and R2 and R3 independently indicate a hydrogen atom, an alkyl group, a phenyl group or an alkenyl group, or together indicate a cyclic alkyl group, a cyclic alkenyl group, a cyclic alkyl group having a phenyl group or a cyclic alkenyl group having a phenyl group.Type: GrantFiled: October 12, 1999Date of Patent: July 17, 2001Assignee: Matsushita Electric Industrial Co., Ltd.Inventors: Masayuki Endo, Masamitsu Shirai, Masahiro Tsunooka
-
Patent number: 6180313Abstract: Disclosed is a poly(disulfonyl diazomethane) compound as a class of novel compounds represented by the general formula R-SO2-C(N2)-SO2&Brketopenst; Z-SO2-C(N2)-SO2&Brketclosest; nR in which the subscript n is 1 to 5, each R is a monovalent hydrocarbon group and Z is a divalent hydrocarbon group. The invention also discloses a chemical-amplification positive-working photoresist composition which comprises the above mentioned poly(disulfonyl diazomethane) compound as the radiation-sensitive acid-generating agent in combination with a film-forming resin capable of being imparted with increased solubility in an aqueous alkaline solution by the interaction with an acid, such as a polyhydroxystyrene resin of which a part of the hydroxyl groups are substituted by acid-dissociable solubility-reducing groups, e.g., tert-butoxycarbonyl groups.Type: GrantFiled: August 27, 1999Date of Patent: January 30, 2001Assignee: Tokyo Ohka Kogyo Co., Ltd.Inventors: Hiroto Yukawa, Waki Ohkubo, Kouki Tamura
-
Patent number: 6074708Abstract: A photoinitiator is represented by general formula (I): ##STR1## where n is an integer of 1 or greater; A and B are each a trans cyclohexane ring or a benzene ring, the benzene ring being allowed to include a fluorine atom or a methyl group as a substituent, the benzene ring adjacent to a carbonyl group being allowed to include a fluorine atom or a methyl group as a substituent; p and q are each 0 or 1, p and q are not simultaneously 0; X is an alkyl group of C.sub.1 through C.sub.3 or hydrogen atom, Y is a methyl group, ethyl group or alkoxy group of C.sub.1 through C.sub.3, and Z is a methyl group, ethyl group, alkyl-substituted phenyl group or a group represented by general formula (II), Y and Z being allowed to bonded together to form a ring: ##STR2## where A, B, n, p and q are identical with those in general formula (I).Type: GrantFiled: December 22, 1998Date of Patent: June 13, 2000Assignees: Sharp Kabushiki Kaisha, Nippon Kayaku Co., Ltd.Inventors: Noriaki Onishi, Aya Miyazaki, Daisaku Matsunaga, Touru Ozaki
-
Patent number: 6048667Abstract: Heterogeneous photoinitiator in microparticle form, which consists of a finely divided substrate material to which identical or different photoinitiators are covalently bonded. The photoinitiators are suitable for the radiation-induced polymerization of photopolymerizable or photocrosslinkable monomers for the production of moldings, protective coats and relief images.Type: GrantFiled: January 15, 1998Date of Patent: April 11, 2000Assignee: Ciba Specialty Chemicals Corp.Inventors: Sameer Hosam Eldin, Peter Grieshaber, Fran.cedilla.ois Rime, Kurt Dietliker
-
Patent number: 6030749Abstract: A photosensitive resin composition comprising (A) a binder polymer and/or a prepolymer; (B) an ethylenically unsaturated compound; (C) a radical producer capable of producing a free radical upon exposure to an ultraviolet ray of 300 to 400 nm; and (D) an anthraquinone dye capable of exhibiting a color change upon exposure to an ultraviolet ray having a wavelength in the range of 300 to 400 nm in the presence of the radical producer (C). This photosensitive resin composition, upon exposure through a negative mask to an ultraviolet ray of a wavelength in a specific range and of a quantity larger than a threshold value, can form a photoresin product having image and non-image portions which are different in color from each other, and, hence, this composition can advantageously be used in the fields of printing plates and resists.Type: GrantFiled: March 20, 1992Date of Patent: February 29, 2000Assignee: Asahi Kasei Kogyo Kabushiki KaishaInventor: Katsuhiro Takahashi
-
Patent number: 5976735Abstract: There is described a lithographic plate which comprises a base coated with a photopolymerisable composition which comprises a polymeric binder, at least one free-radically polymerisable ethylenically unsaturated compound and as the photoinitiator combination a metallocene compound, N-phenyl glycine or a substituted N-phenyl glycine or an N-phenyl glycine derivative together with a third component which is a substance which helps in the reaction initiation but also increases the sensitivity of the photopolymerisable composition to a desired region of the spectrum.Type: GrantFiled: March 21, 1996Date of Patent: November 2, 1999Assignee: Kodak Polychrome Graphics LLCInventors: Alan Stanley Victor Monk, Peter Andrew Reath Bennett, Christopher David McCullogh, Geoffrey Horne
-
Patent number: 5770345Abstract: The sensitivity of a photoresist to actinic light is improved by the addition of certain dyes. The photoresist includes a polymer matrix, a photosensitive acid generator and at least one compound selected from the group consisting of dyes containing at least one heterosulphur atom such as 2,2.sup.1,5.sup.1,2"-terthiophene and its derivatives; thianthrene and its derivatives, and 4,6-diphenylthieno(3,4-d)-1,3-dioxol-2-one-5,5-dioxide; phenylsulfone and its derivatives; and 4,5-diphenyl-1,3-dioxol-2-one; 3,4-bis(acetoxymethyl)furan; chelidonic acid and its derivatives; and 5,7,12,14-pentacenetetrone. Resist images on a substrate are formed from the compositions.Type: GrantFiled: July 16, 1996Date of Patent: June 23, 1998Assignee: International Business Machines CorporationInventors: Edward Darko Babich, Karen Elizabeth Petrillo, John Patrick Simons, David Earle Seeger
-
Patent number: 5767169Abstract: A photopolymerizable composition comprising (a) at least one ethylenically unsaturated photopolymerizable compound, and (b) alkoxyphenyl-substituted bisacylphosphine oxides of the formula I ##STR1## in which R.sub.1 and R.sub.2 are identical or different and are a radical of the formula II ##STR2## in which R.sub.4 and R.sub.5 independently of one another are C.sub.1 -C.sub.12 alkyl or C.sub.1 -C.sub.12 alkoxy, andR.sub.6, R.sub.7 and R.sub.8 independently of one another are hydrogen, C.sub.1 -C.sub.12 alkyl, C.sub.1 -C.sub.12 alkoxy or halogen,R.sub.3 is a radical of the formula III ##STR3## in which R.sub.9 is C.sub.1 -C.sub.20 alkyl, C.sub.2 -C.sub.20 alkyl, C.sub.5 -C.sub.6 cycloalkyl, phenyl, naphthyl, phenyl-C.sub.1 -C.sub.5 alkyl, C.sub.2 -C.sub.12 alkenyl, --CF.sub.3 or ##STR4## or R.sub.9 is a radical of the formula IV or V ##STR5## in which X is for example C.sub.1 -C.sub.16 alkylene, C.sub.4 -C.sub.12 alkenylene or is xylylene,R.sub.10 is for example hydrogen, C.sub.1 -C.sub.20 alkyl, C.sub.2 -C.Type: GrantFiled: February 14, 1996Date of Patent: June 16, 1998Assignee: Ciba Specialty Chemicals CorporationInventors: David George Leppard, Manfred Kohler
-
Patent number: 5756255Abstract: Proposed is a novel undercoating composition used in the photolithographic patterning of a photoresist layer by intervening between the substrate surface and the photoresist layer to decrease the adverse influences of the reflecting light from the substrate surface. The undercoating composition of the invention comprises (a) a melamine compound substituted by methylol groups and/or alkoxymethyl groups and (b) a polyhydroxy benzophenone compound, diphenyl sulfone compound or diphenyl sulfoxide compound, optionally, with admixture of (c) an alkali-insoluble resin of a (meth)acrylic acid ester.Type: GrantFiled: November 12, 1996Date of Patent: May 26, 1998Assignee: Tokyo Ohka Kogyo Co., Ltd.Inventors: Mitsuru Sato, Katsumi Oomori, Kiyoshi Ishikawa, Etsuko Iguchi, Toshimasa Nakayama
-
Patent number: 5753412Abstract: The sensitivity of a photoresist to actinic light is improved by the addition of certain dyes. The photoresist includes a polymer matrix, a photosensitive acid generator and at least one compound selected from the group consisting of dyes containing at least one heterosulphur atom such as 2,2.sup.1,5.sup.1,2"-terthiophene and its derivatives; thianthrene and its derivatives, and 4,6-diphenylthieno(3,4-d)-1,3-dioxol-2-one-5,5-dioxide; phenylsulfone and its derivatives; and 4,5-diphenyl-l,3-dioxol-2-one; 3,4-bis(acetoxymethyl)furan; chelidonic acid and its derivatives; and 5,7,12,14-pentacenetetrone. Resist images on a substrate are formed from the compositions.Type: GrantFiled: June 5, 1996Date of Patent: May 19, 1998Assignee: International Business Machines CorporationInventors: Edward Darko Babich, Karen Elizabeth Petrillo, John Patrick Simons, David Earle Seeger
-
Patent number: 5645974Abstract: Compositions comprising a linear base polymer, an ethylenically unsaturated addition-polymerizable compound and a combination of (A) a 1-benzoyl-1-amino-substituted-1-benzylalkane with (B) an .alpha.-phenyl-.alpha.,.alpha.-dialkoxyacetophenone as photopolymerization initiator are suitable for the production of thick-film printing plates.Type: GrantFiled: April 22, 1996Date of Patent: July 8, 1997Assignees: Tokyo Ohka Kogyo, K.K., Ciba-Geigy CorporationInventors: Katsuyuki Ohta, Toshiya Takagi, Toshimi Aoyama
-
Patent number: 5627006Abstract: A photoresist composition comprising (a) a difficultly alkali-soluble special resin, (b) a photo-sensitive compound capable of generating a carboxylic acid, and (c) a solvent, is effective for pattern formation using deep ultraviolet light, KrF excimer laser beams, etc.Type: GrantFiled: April 18, 1995Date of Patent: May 6, 1997Assignees: Wako Pure Chemical Industries, Ltd., Matsushita Electric Industrial Co., Ltd.Inventors: Fumiyoshi Urano, Keiji Oono, Hirotoshi Fujie
-
Patent number: 5609992Abstract: A photopolymerizable composition is disclosed, comprising (i) a compound having at least one addition-polymerizable, ethylenically unsaturated bond; (ii) a compound represented by formula (IA) or (IB): ##STR1## wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.9, R.sup.10, R.sup.11 and R.sup.12 each independently represents a hydrogen atom, a halogen atom, an alkyl group, a substituted alkyl group, an aryl group, a substituted aryl group, a hydroxyl group, a substituted oxy group, a mercapto group, a substituted thio group, an amino group, a substituted amino group, a substituted carbonyl group, a sulfo group, a sulfonato group, a substituted sulfinyl group, a substituted sulfonyl group, a phosphono group, a substituted phosphono group, a phosphonato group, a substituted phosphonato group, a cyano group or a nitro group or R.sup.1 and R.sup.2, R.sup.2 and R.sup.3, R.sup.3 and R.sup.4, R.sup.9 and R.sup.10, R.sup.10 and R.sup.11 or R.sup.11 and R.sup.Type: GrantFiled: October 27, 1995Date of Patent: March 11, 1997Assignee: Fuji Photo Film Co., Ltd.Inventors: Tadahiro Sorori, Yasuo Okamoto, Syunichi Kondo, Hiromichi Kurita
-
Patent number: 5593812Abstract: The sensitivity of a photoresist to actinic light is improved by the addition of certain dyes. The photoresist includes a polymer matrix, a photosensitive acid generator and at least one compound selected from the group consisting of dyes containing at least one heterosulphur atom such as 2,2.sup.1,5.sup.1,2"-terthiophene and its derivatives; thianthrene and its derivatives, and 4,6-diphenylthieno(3,4-d)-1,3-dioxol-2-one-5,5-dioxide; phenylsulfone and its derivatives; and 4,5-diphenyl-1,3-dioxol-2-one; 3,4-bis(acetoxymethyl)furan; chelidonic acid and its derivatives; and 5,7,12,14-pentacenetetrone. Resist images on a substrate are formed from the compositions.Type: GrantFiled: February 17, 1995Date of Patent: January 14, 1997Assignee: International Business Machines CorporationInventors: Edward D. Babich, Karen E. Petrillo, John P. Simons, David E. Seeger
-
Patent number: 5543262Abstract: A light sensitive composition which is capable of photopolymerization which includes a photopolymerizable compound a free radical generating component and a benzanthrone or substituted benzanthrone which substantially prevents photopolymerization when the light sensitive composition is exposed to actinic radiation below a threshold amount but permits photopolymerization when the light sensitive composition is exposed to actinic radiation above a threshold amount. This achieves a gate effect which eliminates or decreases unwanted partial exposure in the nonimage areas and hence improves reproduction quality.Type: GrantFiled: February 24, 1995Date of Patent: August 6, 1996Assignee: International Paper CompanyInventors: Maria T. Sypek, John R. Delude, Paul A. Perron
-
Patent number: 5541038Abstract: Compositions comprising a linear base polymer, an ethylenically unsaturated addition-polymerizable compound and a combination of (A) a 1-benzoyl-1-amino-substituted-1-benzylalkane with (B) an .alpha.-phenyl-.alpha.,.alpha.-dialkoxyacetophenone as photopolymerization initiator are suitable for the production of thick-film printing plates.Type: GrantFiled: April 5, 1995Date of Patent: July 30, 1996Assignees: Ciba-Geigy Corporation, Tokyo Ohka Kogyo, K.K.Inventors: Katsuyuki Ohta, Toshiya Takagi, Toshimi Aoyama
-
Patent number: 5468589Abstract: A resist composition comprising (a) a polymer having at least repeating units of the formulae: ##STR1## (b) a photoacid generator and (c) a solvent, has high sensitivity to light, excellent heat resistance, adhesiveness to a substrate and suitable for pattern formation with high resolution.Type: GrantFiled: June 15, 1992Date of Patent: November 21, 1995Assignees: Wako Pure Chemical Industries, Ltd., Matsushita Electric Industrial Co., Ltd.Inventors: Fumiyoshi Urano, Hirotoshi Fujie, Keiji Oono, Takaaki Negishi
-
Patent number: 5451343Abstract: The present invention relates to a novel class of compounds which absorb light at wavelengths greater than 350 nm and are useful as fluorescers or as photoinitiators. The present invention provides compounds of the formulas (I) and (II) and their equivalents (the nomenclature of the compounds used herein is based on the numbering of positions as shown in formula (I)): ##STR1## where: when W is .dbd.O, W.sup.1 is hydrogen or --OR.sup.9 and when W is .dbd.NR.sup.+.sub.2, W is hydrogen or NR.sub.2.sup.+2, A is hydrogen, alkenyl, alkyl or an election withdrawing group, and the remaining groups are as defined in the disclosure.Type: GrantFiled: November 19, 1993Date of Patent: September 19, 1995Assignee: Spectra Group Limited, Inc.Inventors: Douglas C. Neckers, Jianmin Shi
-
Patent number: 5447797Abstract: A reaction resin mixture, which is able to be hardened thermally and by means of UV radiation, contains the following constituents:a cationically polymerizable epoxide resin;a latent hardening initiator in the form of an aralkyl-thiolanium salt; anda sensitizer of the structure ##STR1## A being --CO--, --NR-- and --CO--CO--, and D being --O--, --S--, --CO-- and --CH.sub.2).sub.x (where x= 1 or 2) or rather a single bond or two hydrogen atoms.Type: GrantFiled: August 9, 1993Date of Patent: September 5, 1995Assignee: Siemens AktiengesellschaftInventors: Bernhard Stapp, Lothar Schoen, Volker Muhrer
-
Patent number: 5415976Abstract: Aminoketone-substituted coumarin sensitizers having tethered tertiary amino groups are described which have extremely good photosensitivity. The sensitizers of the instant invention have the formula: ##STR1## wherein R.sub.1 and R.sub.2 each represent an alkyl group having 1 to 6 carbon atoms, and R.sub.3 and R.sub.4 each represent hydrogen; or at least one of R.sub.1 and R.sub.3 or R.sub.2 and R.sub.4 together represent an alkylene group having 2 to 4 carbon atoms,R.sub.5 represents an alkyl group having 1 to 6 carbon atoms or H,R.sub.6 represents an alkylene group having 1 to 6 carbon atoms, andR.sub.7 and R.sub.8 each independently represent an alkyl group having 1 to 6 carbon atoms, both of R.sub.7 and R.sub.8 taken together represent an alkylene group having 4 to 6 carbon atoms, or R.sub.5 or R.sub.6 taken together with R.sub.7 or R.sub.8 represent a five, six, or seven membered heterocyclic ring group.Type: GrantFiled: April 28, 1994Date of Patent: May 16, 1995Assignee: Minnesota Mining and Manufacturing CompanyInventor: M. Zaki Ali
-
Patent number: 5401608Abstract: A negative-working radiation-sensitive mixture containinga) a compound which contains at least one --CBr.sub.3 group bound to an atom not linked in turn to a hydrogen atom,b) an alkoxymethylated melamine andc) a water-insoluble polymeric binder which is soluble, or at least swellable, in aqueous alkaline solutions and contains phenolic OH groups,wherein(1) the mixture has an absorption of <0.4 .mu.m.sup.-1 at 248 nm,(2) the CBr.sub.3 group of the compound a) is bound to the sulfur atom of a sulfonyl group and the compound a) is contained in the mixture in an amount of 0.2 to 10% by weight, based on the total amount of the components b) and c),(3) the ratio by mass of the components b) and c) is between 50:50 and 5:95 and(4) the component c) is a homopolymer or copolymer of hydroxystyrene or a derivative thereof, the homopolymer or copolymer having a removal rate of 200 to 3,000 nm/min at 21.degree. C. in an aqueous alkaline developer containing 2.Type: GrantFiled: July 23, 1992Date of Patent: March 28, 1995Assignee: Hoechst AktiengesellschaftInventors: Georg Pawlowski, Ralph Dammel, Horst Roeschert, Winfried Meier, Walter Spiess, Klaus-Juergen Przybilla
-
Patent number: 5368985Abstract: Bisacylphosphine sulfides of formula I ##STR1## wherein R.sub.1 is unsubstituted C.sub.1 -C.sub.18 or C.sub.1 -C.sub.8 alkyl which is substituted by phenyl, --CN, C.sub.1 -C.sub.12 alkoxy or halogen, C.sub.2 -C.sub.18 alkenyl, unsubstituted C.sub.5 -C.sub.8 cycloalkyl or C.sub.5 -C.sub.8 cycloalkyl which is substituted by C.sub.1 -C.sub.12 alkyl, C.sub.1 -C.sub.12 alkoxy or halogen, unsubstituted C.sub.6 -C.sub.12 aryl or C.sub.6 -C.sub.12 aryl which is substituted by halogen, C.sub.1 -C.sub.12 alkyl or C.sub.1 -C.sub.12 alkoxy, or a 5- or 6-membered aromatic heterocyclic radical which contains oxygen, sulfur and/or nitrogen and is unsubstituted or substituted by halogen, C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy, andR.sub.2 and R.sub.3 are each independently of the other unsubstituted C.sub.1 -C.sub.18 alkyl or C.sub.1 -C.sub.8 alkyl which is substituted by phenyl, halogen or C.sub.1 -C.sub.12 alkoxy, C.sub.2 -C.sub.6 alkenyl, unsubstituted C.sub.5 -C.sub.8 cycloalkyl or C.sub.5 -C.sub.Type: GrantFiled: February 28, 1994Date of Patent: November 29, 1994Assignee: Ciba-Geigy CorporationInventors: Werner Rutsch, Gebhard Hug, Manfred Kohler
-
Patent number: 5350660Abstract: A resist material comprising (a) a polymer having a monomer unit having a special functional group, a monomer unit having a phenolic hydroxyl group, and if necessary a third monomer unit, (b) a photoacid generator, and (c) a solvent can provide a resist film excellent in heat resistance and adhesiveness to a substrate when exposed to light with 300 nm or less such as deep UV light, KrF excimer laser light, etc., and is suitable for forming ultrafine patterns.Type: GrantFiled: January 28, 1991Date of Patent: September 27, 1994Assignee: Wako Pure Chemical Industries, Ltd.Inventors: Fumiyoshi Urano, Masaaki Nakahata, Hirotoshi Fujie, Keiji Oono
-
Patent number: 5306600Abstract: Titanocenes of the formula I ##STR1## in which R.sup.1 are cyclopentadienyl.sup..crclbar. groups and R.sup.2 and R.sup.3 are aromatic radicals which are substituted in both ortho-positions by fluorine and, in addition, are substituted by an acyloxy group are suitable as photoinitiators for the photopolymerization of ethylenically unsaturated compounds.Type: GrantFiled: November 12, 1992Date of Patent: April 26, 1994Assignee: Ciba-Geigy CorporationInventors: Eginhard Steiner, Harry Beyeler, Martin Riediker, Vincent Desobry, Kurt Dietliker, Rinaldo Husler
-
Patent number: 5279921Abstract: Disclosed is a pattern formation resist which can be exposed with deep UV, has a high dry etching resistance, has a large allowance in a development manipulation using an aqueous alkali solution, and can form a fine pattern having a good sectional shape. The resist comprises an alkali-soluble polymer and a compound represented by the following formula (I) and simultaneously containing, in a single molecule, a substituent which decomposes with an acid and a group which produces an acid with deep UV: ##STR1## wherein the substituent which decomposes with an acid is present in at least one of R.sub.1 to R.sub.4, and when R.sub.1 to R.sub.4 have a group except for the substituent which decomposes with an acid, R.sub.1 represents a nonsubstituted or substituted aliphatic hydrocarbon group, each of R.sub.2 and R.sub.3 independently represents a hydrogen atom or a non-substituted or substituted aliphatic hydrocarbon group, and R.sub.4 represents a nonsubstituted or substituted aliphatic hydrocarbon group.Type: GrantFiled: November 27, 1991Date of Patent: January 18, 1994Assignee: Kabushiki Kaisha ToshibaInventors: Yasunobu Onishi, Yoshihito Kobayashi, Hirokazu Niki
-
Patent number: 5256520Abstract: Photopolymerizable compositions containing photoinitiator systems that absorb in the visible are disclosed. The photopolymerizable compositions contain at least one ethylenically unsaturated monomer capable of free radical initiated addition polymerization and a photoinitiator system capable of being activated by actinic radiation. The photoinitiator system comprises a hexaarylbisimidazole, a chain transfer agent, and a sensitizer given by the formulae A or B wherein X and R.sub.1 -R.sub.13 are as defined herein.Type: GrantFiled: November 10, 1992Date of Patent: October 26, 1993Assignee: E. I. Du Pont de Nemours and CompanyInventor: William K. Smothers
-
Patent number: 5192642Abstract: Titanocenes of the formula I ##STR1## in which R.sup.1 are cyclopentadienyl.sup..crclbar. groups and R.sup.2 and R.sup.3 are aromatic radicals which are substituted in both ortho-positions by fluorine and, in addition, are substituted by an acyloxy group are suitable as photoinitiators for the photopolymerization of ethylenically unsaturated compounds.Type: GrantFiled: May 23, 1990Date of Patent: March 9, 1993Assignee: Ciba-Geigy CorporationInventors: Eginhard Steiner, Harry Beyeler, Martin Riediker, Vincent Desobry, Kurt Dietliker, Rinaldo Husler
-
Patent number: 5147900Abstract: An energy polymerizable composition comprises at least one ethylenically-unsaturated monomer, one of polyurethane precursors, and at least one epoxy monomer, and a curing agent comprising an organometallic compound, and an onium salt.Type: GrantFiled: April 24, 1990Date of Patent: September 15, 1992Assignee: Minnesosta Mining and Manufacturing CompanyInventors: Michael C. Palazzotto, Katherine A. Brown-Wensley, Robert J. DeVoe
-
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
-
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
-
Patent number: 5091282Abstract: This invention includes a photosensitive composition containing an alkali-soluble resin and a compound represented by formula (I), (II) or (III) described in the claims and the specification, a photosensitive composition containing an alkali-soluble polymer, a compound represented by formula (IV) described in the claims and the specification and a basic compound, and a photosensitive composition containing an alkali-soluble polymer, a compound represented by formula (VI) described in the claims and the specification and a compound which produces an acid upon radiation of light.Type: GrantFiled: April 3, 1990Date of Patent: February 25, 1992Assignee: Kabushiki Kaisha ToshibaInventors: Yasunobu Onishi, Hirokazu Niki, Yoshihito Kobayashi, Rumiko Hayase, Toru Ushirogouchi
-
Patent number: 5087550Abstract: Radiation-reactive mixtures suitable for producing insulating layers and printed circuits are composed of certain precursors for preparing polyimides, polyisoindoloquinazolinediones, polyoxiazinediones, polyquinazolinediones or polyquinazolones and aryl-containing carbonyl compounds which when excited by UV radiation are capable of hydrogen abstraction, these mixtures undergoing solubility differentiation on irradiation with actinic light.Type: GrantFiled: September 26, 1989Date of Patent: February 11, 1992Assignee: BASF AktiengesellschaftInventors: Rainer Blum, Gerd Rehmer, Hans Schupp
-
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
-
Patent number: 5011762Abstract: A photosensitive composition which is suitable for free radical polymerization systems initiated by ultraviolet light, particularly useful in UV-curing coating and image transfer systems such as printing plates and photoresists. Among the above mentioned applications, systems in which the photosensitive layer has no protective film to insulate it from the air shows the greatest improvement in photosensitivity.Type: GrantFiled: August 14, 1990Date of Patent: April 30, 1991Assignee: Industrial Technology Research InstituteInventors: Rong-Jer Lee, Chein-Dhau Lee, Wen-Shin Shen