Sulfur In Heterocyclic Ring Patents (Class 430/922)
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Patent number: 5102775Abstract: A composition for visible light sensitive electrodeposition coating which comprises (A) a photocurable resin having light sensitive groups capable of being crosslinked or polymerized by light irradiation and ionic groups, (B) a sensitizer which is excited by absorption of visible light and has a property to interact with the resin (A), (C) a water-insoluble polymerization initiator, and optionally, (D) at least one specific nitrogen-containing compound; and an image-forming method which comprises (i) coating the surface of a conductor by electrodeposition with the aforesaid composition, (ii) exposing the resulting film by electrodeposition by partially irradiating the film with visible light, and then (iii) contacting the resulting film with a developing solution to remove the unexposed areas.Type: GrantFiled: September 28, 1989Date of Patent: April 7, 1992Assignee: Kansai Paint Co., Ltd.Inventors: Motoko Okuhara, Ichiro Yoshihara, Yasuo Doi, Takao Yamamoto, Kenji Seko, Yutaka Yoshikawa, Naozumi Iwasawa
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Patent number: 5068371Abstract: 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 a pyrrylalkyl group, amidoalkyl group or imidoalkyl group, are suitable as photoinitiators for the photopolymerization of ethylenically unsaturated compounds.Type: GrantFiled: May 23, 1990Date of Patent: November 26, 1991Assignee: Ciba-Geigy CorporationInventors: Eginhard Steiner, Harry Beyeler, Rinaldo Husler
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Patent number: 5064746Abstract: The radiation-sensitive mixture contains(a) a polymeric binder which is insoluble in water but soluble in aqueous alkaline solutions and(b) an organic compound whose solubility in an aqueous alkaline developer is increased by the action of an acid and which contains one or more acid-cleavable groups,the polymeric binder (a) being a copolymer which contains o-nitrobenzyl groups.The novel radiation-sensitive mixture is particularly suitable for the production of photoresists.Type: GrantFiled: April 14, 1989Date of Patent: November 12, 1991Assignee: BASF AktiengesellschaftInventor: Reinhold Schwalm
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Patent number: 5064747Abstract: A light-sensitive composition comprises a photo-crosslinkable polymer having a photo-dimerizable unsaturated bond and a sensitizer represented by the following general formula (I): ##STR1## wherein R.sub.1 and R.sub.2 each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group or a substituted or unsubstituted allyl group, provided that R.sub.1 and R.sub.2 may form a ring together with the carbon atoms to which they are attached; n represents 0, 1 or 2; and G.sub.1 and G.sub.2 each independently represents a hydrogen atom, a cyano group, a substituted or unsubstituted alkoxycarbonyl group, a substituted or unsubstituted aryloxycarbonyl group, a substituted or unsubstituted acyl group, a substituted or unsubstituted arylcarbonyl group, an alkylthio group, an arylthio group, an alkylsulfonyl group, an arylsulfonyl group or a fluoroalkylsulfonyl group, provided that G.sub.1 and G.sub.Type: GrantFiled: July 19, 1990Date of Patent: November 12, 1991Assignee: Fuji Photo Film Co., Ltd.Inventors: Masanori Imai, Noriaki Watanabe, Kouichi Kawamura
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Patent number: 5061605Abstract: A photopolymerizable composition comprises an addition polymerizable compound having at least one ethylenically unsaturated double bond and a photopolymerization initiator, wherein it comprises a compound represented by the following general formula (I) as the photopolymerization initiator: ##STR1## (wherein R.sub.1 and R.sub.2 may be the same or different and each independently represents a substituted or unsubstituted alkyl, aryl or alkenyl group or R.sub.1 and R.sub.2 may form a non-metallic ring together with the sulfur atoms to which they are bonded; n is 0, 1 or 2; G.sub.1 and G.sub.2 may be the same or different and each represents a hydrogen atom, a cyano group or a substituted or unsubstituted alkoxycarbonyl, aryloxycarbonyl, acyl, arylcarbonyl, alkylthio, arylthio, alkylsulfonyl, arylsulfonyl or fluoroalkylsulfonyl group, provided that G.sub.1 and G.sub.2 do not simultaneously represent hydrogen atoms or G.sub.1 and G.sub.Type: GrantFiled: April 16, 1991Date of Patent: October 29, 1991Assignee: Fuji Photo Film Co., Ltd.Inventors: Kouichi Kawamura, Mitsumasa Tsuchiya
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Patent number: 5049481Abstract: A photopolymerizable composition comprising (i) a polymerizable compound having an addition polymerizable unsaturated bond, (ii) a compound represented by formula (Ia): ##STR1## a compound represented by formula (Ib): ##STR2## or a compound represented by formula (Ic): ##STR3## wherein A represents an oxygen atom, a sulfur atom, a selenium atom, a tellurium atom, an alkyl- or aryl-substituted nitrogen atom, or a dialkyl-substituted carbon atom; Y.sup.1 represents a hydrogen atom, an alkyl group, a substituted alkyl group, an aryl group, a substituted aryl group, an aralkyl group, an acyl group, an alkoxycarbonyl group, or a substituted alkoxycarbonyl group; R.sup.1 and R.sup.2 each represents a hydrogen atom, an alkyl group having from 1 to 18 carbon atoms, or an alkyl group having from 1 to 18 carbon atoms which is substituted with R.sup.3 O--, ##STR4## or a halogen atom (i.e., F, Cl, Br, and I), wherein R.sup.Type: GrantFiled: December 26, 1989Date of Patent: September 17, 1991Assignee: Fuji Photo Film Co., Ltd.Inventors: Yasuo Okamoto, Tadahiro Sorori
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Patent number: 5026624Abstract: An improved photoimagable cationically polymerizable epoxy based coating material is provided. The material includes an epoxy resin system consisting essentially of between about 10% and about 80% by weight of a polyol resin which is a condensation product of epichlorohydrin and bisphenol A having a molecular weight of between about 40,000 and 130,000; between about 20% and about 90% by weight of an epoxidized octafunctional bisphenol A formaldehyde novolak resin having a molecular weight of 4,000 to 10,000; and if flame retardancy is required between about 35% and 50% by weight of an epoxidized glycidyl ether of tetrabromo bisphenol A having a softening point of between about 60.degree. C. and about 110.degree. C. and a molecular weight of between about 600 and 2,500. To this resin system is added about 0.Type: GrantFiled: March 3, 1989Date of Patent: June 25, 1991Assignee: International Business Machines CorporationInventors: Richard A. Day, Jeffrey D. Gelorme, David J. Russell, Steven J. Wih
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Patent number: 4987057Abstract: A photoinitiator composition comprising (1) an aminobenzylidene carbonyl compound and (2) an N-aryl-.alpha.-amino acid is suitable for use in a photo-polymerizable composition comprising (a) an addition-polymerizable compound having a boiling point of 100.degree. C. or higher at an atmospheric pressure and (b) said photoinitiator composition.Type: GrantFiled: May 22, 1989Date of Patent: January 22, 1991Assignee: Hitachi Chemical Co., Ltd.Inventors: Makoto Kaji, Nobuyuki Hayashi
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Patent number: 4985470Abstract: A photopolymerizable composition which comprises an addition-polymerizable compound having at least one ethylenically unsaturated double bond and a photopolymerization initiator system, characterized in that said photopolymerization initiator system essentially consists of:(a) a p-dialkylaminostyrene derivative or p-dialkylaminophenylbutadiene derivative represented by the general formula ##STR1## wherein R.sup.1 and R.sup.2 independently represent an alkyl group; Y represents a divalent atom or atomic group selected from the group consisting of --O--, --S-- and --CH.dbd.Type: GrantFiled: June 30, 1986Date of Patent: January 15, 1991Assignee: Mitsubishi Kasei CorporationInventors: Hideki Nagasaka, Noriaki Takahashi
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Patent number: 4966828Abstract: Disclosed is a compound of the general formula ##STR1## wherein L=H or CO--(R.sup.1).sub.n (CX.sub.3).sub.m, M=alkylene, alkenylene, Q=S, Se, O, dialkylmethylene, alken-1,2-ylene, 1,2-phenylene or N-R, with M+Q together forming 3 or 4 ring members, R=alkyl, aralkyl or alkoxyalkyl, R.sup.1 is an aromatic group and X=Cl, Br or I, with n=O and m=1 or n=1 and m=1 or 2. The compounds, on exposure, eliminate HX and form free radicals and are therefore highly effective as acid donors and free radical initiators for photochemical processes.Type: GrantFiled: September 13, 1984Date of Patent: October 30, 1990Assignee: Hoechst AktiengesellschaftInventors: Reinhard Doenges, Hans Ruckert, Ulrich Geissler, Hartmut Steppan
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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: 4935330Abstract: A photopolymerizable mixture containing one or more ethylenically unsaturated, photopolymerizable or photocrosslinkable compounds and a photopolymerization initiator which comprises a combination of an aromatic carbonyl compound of the type stated in claim 1 and an s-triazine compound containing one or more halogen-substituted methyl groups, photosensitive recording elements which possess a photopolymerizable recording layer consisting of these photopolymerizable mixtures, and a process for the production of lithographic printing plates using these recording elements.Type: GrantFiled: November 14, 1989Date of Patent: June 19, 1990Assignee: BASF AktiengesellschaftInventors: Gerhard Hofmann, Reiner Hoffman, Harald Lauke, Wilhelm Weber, Reinhold J. Leyrer
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Patent number: 4933377Abstract: Sulfonium and oxysulfonium salts, useful as photoinitiators, have directly attached to the sulfur atom thereof:at least one aromatic or heterocyclic aromatic substituent containing at least 14 aromatic atoms and having a removable positive hydrogen ion, said substituent exhibiting a higher energy occupied molecular orbital than at least one other substituent directly attached to said sulfur atom;and at least one substituent comprising an electron withdrawing group and exhibiting a lower energy unoccupied molecular orbital than at least one other substituent directly attached to said sulfur atom;said salt being capable, upon exposure to visible radiation, of undergoing irreversible intramolecular rearrangement to form a Bronsted acid comprising the anion of said salt and said removable positive hydrogen ion.Type: GrantFiled: February 29, 1988Date of Patent: June 12, 1990Inventors: Franklin D. Saeva, David T. Breslin
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Patent number: 4910121Abstract: Titanocenes containing .pi.-cyclopentadienyl ligands, in which one or two carbocyclic or heterocyclic aromatic rings are attached to the metal atom, said aromatic rings being substituted by fluorine in at least one of the two ortho-positions relative to the metal-carbon bonds, are suitable photoinitiators for the photopolymerization of ethylenically unsaturated substrates. They are distinguished by high sensitivity, stability to air and heat, and are very effective in the range from UV light to visible light.Type: GrantFiled: July 28, 1987Date of Patent: March 20, 1990Assignee: Ciba-Geigy CorporationInventors: Martin Riediker, Martin Roth, Niklaus Buhler, Joseph Berger
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Patent number: 4895788Abstract: 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;(c) a photopolymerizable mixture of(1) a polyethoxylate diacrylate monomer; aType: GrantFiled: May 26, 1988Date of Patent: January 23, 1990Assignee: Hoechst Celanese CorporationInventors: John E. Walls, Frank C. Pagano
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Patent number: 4874685Abstract: The present invention provide a dye-sensitized photopolymerizable composition comprising a free radical addition polymerizable material, and a photoinitiator, the photoinitiator consisting essentially of a photoreducible dye, a thiol, and an N,N'-dialkylaniline.Type: GrantFiled: November 27, 1987Date of Patent: October 17, 1989Assignee: The Mead CorporationInventor: Paul C. Adair
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Patent number: 4837106Abstract: A recording material comprising (i) an addition polymerizable compound having at least one ethylenic unsaturated double bond, (ii) a photopolymerization initiator composition and (iii) at least one component capable of causing a color reaction, wherein components (i), (ii) and (iii) are contained in microcapsules; and wherein said photopolymerization initiator composition (ii) comprises the following components (a), (b) and (c), whereby the light sensitivity of the recording material is improved:(a) a photo-absorbent having a molecular extinction coefficient of 10.sup.3 or more at a maximum absorption wavelength;(b) a hexaaryl-biimidazole; and(c) a heterocyclic mercapto compound of general formula (I): ##STR1## where Z is a non-metallic atomic group for formation of a nitrogen-containing heterocyclic nucleus.Type: GrantFiled: December 29, 1986Date of Patent: June 6, 1989Assignee: Fuji Photo Film Co., Ltd.Inventors: Shun-ichi Ishikawa, Tadao Imagawa, Minoru Maeda, Fumiaki Shinozaki
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Patent number: 4816379Abstract: Relief plates and printing plates are produced by a positive-working process, using a photopolymerizable layer which contains one or more photopolymerizable, olefinically unsaturated compounds, one or more photoinitiators which can be activated by UV light, and a combination of a phenothiazinium, phenoxazinium, phenazinium or acridinium dye with a mild reducing agent which, on exposure to visible light, is capable of reducing the dye in the excited electronic state. The photopolymerizable layer is exposed imagewise to light having a wavelength longer than 450 nm, and simultaneously or subsequently exposed uniformly to light having a wavelength of from 300 to 420 nm, after which the unpolymerized areas of the layer are removed.Type: GrantFiled: April 22, 1985Date of Patent: March 28, 1989Assignee: BASF AktiengesellschaftInventors: Bernd Bronstert, Gerhard Hoffmann, John Lynch
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Patent number: 4810618Abstract: A photopolymerizable composition comprises at least one polymerizable compound having at least one ethylenically unsaturated bond therein and at least one photopolymerization initiator and optionally at least one linear organic high molecular weight polymer and characterized in that the photopolymerization initiator comprises a specific combination of two kinds of compounds, for instance, 2,4,6-tris(trichloromethyl)-s-triazine and compound (12) represented by the following formula: ##STR1## The photopolymerizable composition exhibits a high sensitivity to extremely wide range of actinic rays extending from ultraviolet light to visible light and is useful for manufacturing PS plates and photoresist layer for use in making print circuit-boards or the like.Type: GrantFiled: January 11, 1988Date of Patent: March 7, 1989Assignee: Fuji Photo Film Co., Ltd.Inventors: Mitsuru Koike, Koichi Kawamura
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Patent number: 4772538Abstract: 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;(c) a photopolymerizable mixture of(1) a polyethoxylate diacrylate monomeType: GrantFiled: August 2, 1985Date of Patent: September 20, 1988Assignee: American Hoechst CorporationInventors: John E. Walls, Frank C. Pagano
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Patent number: 4766055Abstract: 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 or thioxanthene dyestuff, (b) a photosensitizer selected from the group consisting of N-phenylglycine, 2,4,6-tris(trichloromethyl)-1,3,5-triazine, and a mixture of p-dimethylaminobenzoic acid isopentyl ester and 2,4-diisopropylthioxanthone, and (c) a peroxide.Type: GrantFiled: August 1, 1986Date of Patent: August 23, 1988Assignee: Nippon Paint Co., Ltd.Inventors: Masami Kawabata, Koichi Kimoto, Yasuyuki Takimoto
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Patent number: 4756994Abstract: A photocurable composition comprising (a) 100 parts by weight of a resin having structural units derived from at least one alpha, beta-unsaturated ethylenically unsaturated monomer, (b) 10 to 300 parts by weight of a photopolymerizable monomer, (c) 0.1 to 20 parts by weight of a photopolymerization initiator, and (d) 0.01 to 1 part by weight of a compound represented by the following general formula (I) or general formula (II) ##STR1## wherein R.sup.1 represents a divalent aromatic hydrocarbon group having bonds at the ortho-position to each other; R.sup.2 represents hydrogen, an alkyl group having 1 to 4 carbon atoms, a phenyl group or an aryl group having a C.sub.1 -C.sub.4 alkyl; R.sup.3 and R.sup.4 each represent an alkyl group having 1 to 10 carbon atoms, an aryl group or an aralkyl group; X.sup.1 represents oxygen, sulfur or N--R.sup.5 ; X.sup.2 represents oxygen, sulfur or NH; X.sup.3 represents nitrogen or CR.sup.6 ; X.sup.4 represents oxygen, sulfur or NR.sup.6 ; X.sup.5 represents nitrogen or CR.Type: GrantFiled: June 6, 1986Date of Patent: July 12, 1988Assignee: Sekisui Kagaku Kogyo Kabushiki KaishaInventors: Yasuhiko Araki, Shigeru Danjo, Hajime Shohi
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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: 4677047Abstract: Novel compositions of matter which crosslink under the action of light and which contain(A) an aliphatically unsaturated polymerization product which is free of aromatic groups and which can contain structural elements of the formula I ##STR1## (B) a bisimide of the formula II ##STR2## and a sensitizer and, if desired, a further crosslinking agent, where R and R' are alkyl or together are tetramethylene, R.sub.1 is hydrogen, chlorine or methyl, Y and Y' are each --OH or together are --O-- and R.sub.4 is alkylene, arylene or bis-arylene, are suitable, inter alia, for preparing printing plates or as photoresist materials.Type: GrantFiled: September 23, 1985Date of Patent: June 30, 1987Assignee: Ciba-Geigy CorporationInventors: Joseph Berger, Friedrich Lohse
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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: 4657942Abstract: A photopolymerizable composition is described, comprising an addition polymerizable compound having at least two ethylenically unsaturated bonds in the molecule, at least one photopolymerization initiator, and at least one of 2-mercapto-5-substituted thiadiazole compounds represented by formulae (I) and (II) ##STR1## wherein R represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted alkylthio group, or a substituted or unsubstituted aralkylthio group; and R' represents a substituted or unsubstituted alkylene group. The composition has a remarkably good photosensitivity.Type: GrantFiled: January 27, 1986Date of Patent: April 14, 1987Assignee: Fuji Photo Film Co., Ltd.Inventors: Masayuki Iwasaki, Minoru Maeda, Sadao Fujikura
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Patent number: 4618564Abstract: Positive images are produced by (i) exposing to actinic radiation in a predetermined pattern a composition supported on a substrate, which composition comprises a film-forming organic material and a substance which releases a sulphonic acid on exposure to actinic radiation, thereby rendering the composition more soluble in the developer in the exposed areas than the unexposed areas, and (ii) treating the composition with the aqueous base developer to remove the unexposed areas. The image-forming process may be used in the production of printing plates and electrical circuits.Type: GrantFiled: May 24, 1985Date of Patent: October 21, 1986Assignee: Ciba-Geigy CorporationInventors: Christopher G. Demmer, Edward Irving
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Patent number: 4609612Abstract: There are obtained by mixing together approximately equal parts of 1-benzoylcyclohexanol and benzophenone or a benzophenone derivative liquid mixtures which possess a high activity as photoinitiators for the polymerization of ethylenically unsaturated compounds. The level of activity is higher than that of the individual components taken separately.Type: GrantFiled: October 4, 1985Date of Patent: September 2, 1986Assignee: Ciba Geigy CorporationInventors: Godwin Berner, Aloysius H. Manse
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Patent number: 4604342Abstract: A photopolymerizable mixture is described which contains the following: a binding agent which is soluble or at least capable of swelling in aqueous-alkaline solutions, a photoinitiator or a photoinitiator system and at least one ethylenically unsaturated monomer, whereby at least one monomer contains an aromatic hydroxyl-, mercapto-, sulfonamide- or a mono-N-substituted sulfonamide group, or combinations thereof.Type: GrantFiled: March 13, 1985Date of Patent: August 5, 1986Assignee: E. I. Du Pont de Nemours and CompanyInventors: Manfred A. J. Sondergeld, Mario Grossa
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Patent number: 4590145Abstract: The initiator composition is effectively used for a photopolymerizable resin composition which comprises a photopolymerizable compound having a double bond for polymerization and a polymer binder and comprises (A) thioxanthone or a substituted thioxanthone and (B) an oxime ester of the formula: ##STR1## wherein R.sub.1 and R.sub.2 may be the same or different and represent each an alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted phenyl, naphthyl, anthryl, pyridyl or quinolyl group or R.sub.1 and R.sub.2 may be bonded together to form a ring, and R.sub.3 represents an alkyl group having 1 to 5 carbon atoms or a substituted or unsubstituted aryl group.Type: GrantFiled: June 28, 1985Date of Patent: May 20, 1986Assignee: Daicel Chemical Industries, Ltd.Inventors: Masanori Itoh, Fumio Takenaka, Kouzi Tohya
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Patent number: 4587200Abstract: A photopolymerizable composition is disclosed, comprising a polymerizable compound having at least one ethylenic unsaturated double bond and a photopolymerization initiator, where the photopolymerization initiator is a combination of (A) acridine having a substituted or unsubstituted phenyl group at 9-position and (B) a heterocyclic compound having a thiol group connected to a 5- to 7-membered heterocyclic ring containing at least one nitrogen atom. The photopolymermizable composition is useful for preparation of lithographic plates and photoresists and as an adhesive, printing ink or coating material.Type: GrantFiled: June 5, 1984Date of Patent: May 6, 1986Assignee: Fuji Photo Film Co., Ltd.Inventors: Koji Tamoto, Akira Umehara
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Patent number: 4564578Abstract: The novel thioxanthones of the formula I ##STR1## in which R.sub.1, R.sub.2, X and W are as defined in patent claim 1, are suitable, for example, for the preparation of photosensitive, compositions of matter which are capable of undergoing condensation or addition reactions and may or may not be crosslinkable, and which in turn are used for image formation, in particular by means of electroless deposition of metals. Such compositions of matter contain, for example, a thioxanthone of the formula I, an oligomer or polymer with terminal glycidyl groups and, where relevant, a crosslinking agent and/or a salt of a metal or group Ib or VIII of the Periodic Table.Type: GrantFiled: November 14, 1983Date of Patent: January 14, 1986Assignee: Ciba-Geigy CorporationInventors: Jurgen Finter, Walter Fischer
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Patent number: 4563413Abstract: The photosensitive composition of this invention contains (1) an ethylenically unsaturated component capable of forming a high polymer by addition polymerization or crosslinking, (2) a cyclic cisoid conjugated diene as a photooxidizable component capable of reacting with singlet oxygen to form an endoperoxide, and (3) a photooxygenation sensitizer. A process for preparing a photosensitive element, such as a relief printing plate, embodying a layer of such a composition is described.Type: GrantFiled: April 23, 1984Date of Patent: January 7, 1986Assignee: Hercules IncorporatedInventor: Wayne R. Messer
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Patent number: 4563438Abstract: There are obtained by mixing together approximately equal parts of 1-benzoylcyclohexanol and benzophenone or a benzophenone derivative liquid mixtures which possess a high activity as photoinitiators for the polymerization of ethylenically unsaturated compounds. The level of activity is higher than that of the individual components taken separately.Type: GrantFiled: April 26, 1984Date of Patent: January 7, 1986Assignee: Ciba Geigy CorporationInventors: Godwin Berner, Aloysius H. Manser
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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: 4543318Abstract: A photopolymerizable composition is described, comprising (1) a non-gaseous ethylenically unsaturated compound which has at least two ethylenically unsaturated terminal groups and is capable of forming a polymer, (2) a thermoplastic polymeric binder, (3) a photopolymerization initiator which is activated by actinic radiation, and (4) at least one of certain heterocyclic compounds. The composition is useful as a photoresist for producing printed circuit boards, printing plates, etc., by etching or plating, and the photoresist has superior adhesion with respect to the base.Type: GrantFiled: July 2, 1984Date of Patent: September 24, 1985Assignee: Fuji Photo Film Co., Ltd.Inventors: Minoru Maeda, Masayuki Iwasaki, Fumiaki Shinozaki
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Patent number: 4505794Abstract: Thioxanthonecarboxylic acid esters, thioesters or amides of the formula I ##STR1## in which X and Z are hydrogen or one of the substituents defined in more detail in claim 1 and Y is --OR.sub.1, --SR.sub.1 or --N(R.sub.1)(R.sub.2), in which R.sub.1 is C.sub.1-24 alkyl and R.sub.2 is H or R.sub.1, are suitable, if desired together with amines, as initiators for the photopolymerization of ethylenically unsaturated compounds or for photochemical crosslinking of polyolefines. They are also used as sensitizers for photocrosslinkable polymers. They can be prepared by methods known per se, for example by cyclization of phenylthio-phthalic, -isophthalic or -terephthalic acids, which can be correspondingly substituted, and subsequent reaction with suitable alcohols, thiols or amines.Type: GrantFiled: September 23, 1982Date of Patent: March 19, 1985Assignee: Ciba-Geigy CorporationInventors: Vratislav Kvita, Hans Zweifel, Martin Roth, Louis Felder
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Patent number: 4499175Abstract: Aqueous compositions useful in making stencils for screen printing comprise a solution of an unsaturated prepolymer dispersed in an aqueous solution of a colloid, and a photo-initiator. Such compositions may be coated on suitable support sheets to produce photosensitive sheets useful for making stencils for screen printing by the direct, indirect, or direct/indirect methods.Type: GrantFiled: September 22, 1982Date of Patent: February 12, 1985Assignee: Sericol Group LimitedInventors: John R. Curtis, John D. Renwick
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Patent number: 4481276Abstract: A photopolymerizable composition having an improved sensitivity, which comprises a polymerizable compound having an ethylenically unsaturated bond and a photopolymerization initiator, wherein said photopolymerization initiator comprises a compound represented by general formula I ##STR1## wherein R.sup.1 and R.sup.2 each represents a hydrogen atom, an alkyl group, a substituted alkyl group, an aryl group, a substituted aryl group, or an aralkyl group; X represents a substituent having a Hammett's value of not more than 0.7; and Y represents a hydrogen atom, an alkyl group, a substituted alkyl group, an aryl group, a substituted aryl group, an aralkyl group, an acyl group, or an alkoxycarbonyl group and a 1,3,5-triazine compound represented by general formula II ##STR2## wherein R.sup.3, R.sup.4, and R.sup.Type: GrantFiled: November 14, 1983Date of Patent: November 6, 1984Assignee: Fuji Photo Film Co., Ltd.Inventors: Shun-ichi Ishikawa, Koji Tamoto, Masayuki Iwasaki, Akira Umehara
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Patent number: 4478922Abstract: Compositions comprising a polymer and dendrite crystals of a salt consisting of the cation of 2-(4,5-dihydronaphtho[1,2-d]-1,3-dithiole-2-ylidene)-4,5-dihydronaphtho [1,2-d]-1,3-dithiole and an anion are useful in forming conductive coatings.Type: GrantFiled: November 21, 1983Date of Patent: October 23, 1984Assignee: Eastman Kodak CompanyInventors: Jerome H. Perlstein, Neil F. Haley
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Patent number: 4474868Abstract: A photo polymerization initiator composition is disclosed. The composition is comprised of an organic peroxide and a salt selected from the group consisting of pyrylium salts, thiapyrylium salts and selenopyrylium salts represented by the general formula (I): ##STR1## the substituents are defined within the specification. By utilizing the disclosed photo polymerization initiator composition, it is possible to obtain high sensitivity even in the visible range of light.Type: GrantFiled: September 7, 1983Date of Patent: October 2, 1984Assignee: Nippon Oil and Fats Co., Ltd.Inventors: Tsuguo Yamaoka, Kenichi Koseki, Yoshitaka Goto
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Patent number: 4465758Abstract: Described are 1,3-diaza-9-thia-anthracene-2,4-diones of the general formula (II) ##STR1## wherein R.sup.1, R.sup.3 and R.sup.4 are identical or different and individually each denotes a hydrogen or halogen atom, an alkyl, alkoxy, carboxyl or alkoxy-carbonyl group,R.sup.2 denotes an alkoxy, carboxyl or alkoxy-carbonyl group, ortwo of the groups R.sup.1, R.sup.2, R.sup.3, and R.sup.4 together form a condensed aromatic radical.These compounds are used as photoinitiators in photopolymerizable recording materials and have an increased sensitivity in the spectral range between 425 and 480 nm.Type: GrantFiled: August 29, 1983Date of Patent: August 14, 1984Assignee: Hoechst AktiengesellschaftInventors: Rainer Wingen, Klaus Horn, Walter Lutz
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Patent number: 4442197Abstract: Photocurable compositions are provided which can be cured with ultraviolet light at a wave length greater than 300 nm. The photocurable compositions are based on the use of cationically polymerizable organic materials, for example, an epoxy resin and a photoinitiator in the form of a dialkylphenacyl sulfonium salt or hydroxyaryldialkyl sulfonium salt which have been sensitized with a particular dye sensitizer.Type: GrantFiled: January 11, 1982Date of Patent: April 10, 1984Assignee: General Electric CompanyInventors: James V. Crivello, Julia L. Lee
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Patent number: 4439505Abstract: Compositions comprising a polymer and dendrite crystals of a salt consisting of the cation of 2-(4,5-dihydronaphtho[1,2-d]-1,3-dithiole-2-ylidene)-4,5-dihydronaphtho [1,2-d]-1,3-dithiole and an anion are useful in forming conductive coatings.Type: GrantFiled: January 21, 1982Date of Patent: March 27, 1984Assignee: Eastman Kodak CompanyInventors: Jerome H. Perlstein, Neil F. Haley
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Patent number: 4438190Abstract: A photosensitive resin composition comprising (a) at least one compound selected from the group consisting of benzotriazole, benzimidazole, benzothiazole, derivatives thereof and salts thereof, (b) a phosphate compound having photopolymeric unsaturated bonds, (c), if necessary, an organic thermoplastic polymer, (d) a photopolymerizable unsaturated compound having at least one terminal ethylene group and (e) a sensitizer and/or a sensitizer system, and a photosensitive element comprising a layer of said photosensitive resin composition and a support film therefor, are provided. The photosensitive resin composition can form a protective coating film with excellent adhesiveness to the substrate surface, and such a protective coating film or, photosensitive element obtained therefrom can be advantageously used as a resist for soldering mask, etc.Type: GrantFiled: February 24, 1982Date of Patent: March 20, 1984Assignee: Hitachi Chemical Company, Ltd.Inventors: Toshiaki Ishimaru, Katsushige Tsukada, Nobuyuki Hayashi
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Patent number: 4434035Abstract: Mixtures containing at least one hydroxyalkylphenone of the formula ##STR1## wherein R.sup.1 is H, alkyl of 1-4 C atoms or chlorine, R.sup.2 is H or methyl, R.sup.3 is H or methyl, R.sup.4 is alkyl of 1-6 C atoms and R.sup.5 is alkyl of 1-6 C atoms, and at least one 2-alkylthioxanthone of the formula ##STR2## wherein R.sup.6 is alkyl of 1-8 C atoms, have a considerably increased reactivity in initiating the photopolymerization of ethylenically unsaturated compounds. The polymers fully hardened using these initiator mixtures suffer only little yellowing.Type: GrantFiled: April 4, 1983Date of Patent: February 28, 1984Assignee: Merck Patent Gesellschaft mit beschr/a/ nkter HaftungInventors: J/u/ rgen Eichler, Claus Herz, Karl-Heinz Neisius
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Patent number: 4418138Abstract: Aqueous compositions useful in making stencils for screen printing comprise one or more unsaturated monomers, a tertiary amino compound, a colloid, and a water-soluble, carboxy- or sulpho-alkyleneoxy-thioxanthone photoinitiator. When coated on to a suitable support sheet and dried, photosensitive sheets are obtained useful for making stencils for screen printing by the direct, indirect, or direct/indirect methods.Type: GrantFiled: August 25, 1982Date of Patent: November 29, 1983Assignee: Sericol Group LimitedInventor: John R. Curtis
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Patent number: 4410621Abstract: A photosensitive resin composition which comprises (1) an ethylenically unsaturated compound which can be addition polymerized to form a high molecular compound, said addition polymerization being initiated by a free radical and chain-propagating, (2) a 2-polycyclic aryl-4,5-diphenylimidazolyl dimer wherein the polycyclic aryl group at the 2-position comprises at least two benzene rings condensed each other and (3) a heterocyclic mercaptan compound, said photosensitive resin composition being excellent in having a high photopolymerization initiation potency.Type: GrantFiled: April 3, 1981Date of Patent: October 18, 1983Assignee: Toyo Boseki Kabushiki KaishaInventors: Minoru Wada, Minoru Fukuda