Specified Rate-affecting Material Contains Onium Group Patents (Class 522/25)
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Patent number: 5252682Abstract: A cationically initiated curable resin system is provided using polyester dicyclopentadiene oligomer blended with monomer having vinyl ether end groups and a cationic initiator. A process for preparing the resin system and a process of coating are also provided.Type: GrantFiled: December 17, 1992Date of Patent: October 12, 1993Assignee: Zircon CorporationInventor: Charles E. Bayha
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Patent number: 5238744Abstract: A tough polymeric mixture comprises the polymerized product of admixture I or II, whereinadmixture I comprises 5 to 45 weight percent of a first monomer and a photoinitiator therefor, said first monomer being at least one free-radically polymerizable monomer, and 95 to 55 weight percent of a second monomer and a photoinitiator therefor, said second monomer being at least one set of polyurethane precursors, andadmixture II comprises 5 to 45 weight percent of a first monomer and a photoinitiator therefor, said first monomer being at least one set of polyurethane precursors, and 95 to 55 weight percent of a second monomer and a photoinitiator therefor, said second monomer being at least one free-radically polymerizable monomer,said polymeric mixture having been prepared by a process involving two sequential actinic radiations of wavelength ranges centered around .lambda..sub.1 and .lambda..sub.2, respectively, wherein .lambda..sub.1 and .lambda..sub.Type: GrantFiled: January 10, 1992Date of Patent: August 24, 1993Assignee: Minnesota Mining and Manufacturing CompanyInventors: Jerry W. Williams, Robert J. DeVoe
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Patent number: 5236808Abstract: Photopolymerizable compositions containing photoinitiator systems that absorb in the visible are disclosed. The photoinitiator system comprises a sensitizer which is a compound of the structure I: ##STR1## wherein R.sub.2 and R.sub.Type: GrantFiled: April 13, 1992Date of Patent: August 17, 1993Assignee: E. I. Du Pont de Nemours and CompanyInventor: William K. Smothers
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Patent number: 5230982Abstract: A photohardenable composition comprising a free radical addition polymerizable or crosslinkable compound, an ionic dye/reactive counter ion complex capable of absorbing actinic radiation and producing free radicals which initiate free radical polymerization or crosslinking of the polymerizable or crosslinkable compound, and a disulfide represented by the structure ##STR1## wherein X is selected from the group consisting of S and O except in a specific case in which the disulfide is derived from one or more tetrazolyl groups; n represents 0 or 1; A represents the residue of the ring containing the N, C and X atoms, the ring containing five or six members and, in addition, said ring members may be fused to an aromatic ring; and R.sup.Type: GrantFiled: November 19, 1991Date of Patent: July 27, 1993Assignee: The Mead CorporationInventors: Paul D. Davis, Jacqueline G. Truini, David A. Hutchings
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Patent number: 5212046Abstract: A photoacid-generating photoresist composition sensitized with an aromatic, multi-ring, heterocylcic nitrogen containing sensitizer, preferably a ring extended phenothiazine derivative. The use of the sensitizer permits exposure of photoresists to near UV irradiation where such photoresists have heretofore been exposed to deep UV irradiation. The invention is especially useful for acid hardening photoresist systems.Type: GrantFiled: June 28, 1991Date of Patent: May 18, 1993Assignee: Shipley Company Inc.Inventors: Angelo A. Lamola, Gary Calabrese, Roger Sinta
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Patent number: 5208135Abstract: Compounds having a utility as photosensitive dyes in photocurable polymer based imaging systems having a nucleus of general formula (I): ##STR1## wherein: n is 1 or 2,Y is selected from the group consisting of 0 and ##STR2## Z is selected from the group consisting of 0.sup..crclbar. and ##STR3## M.sup..sym. is a cation.Type: GrantFiled: February 11, 1991Date of Patent: May 4, 1993Assignee: Minnesota Mining and Manufacturing CompanyInventors: Ranjan C. Patel, Tran V. Thien, David Warner
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Patent number: 5176984Abstract: A photohardenable composition comprising a free radical addition polymerizable or crosslinkable compound, a cationic dye-borate anion complex, and a borate salt, said complex being capable of absorbing actinic radiation and producing free radicals which initiate free radical polymerization or crosslinking of said compound.Type: GrantFiled: April 12, 1991Date of Patent: January 5, 1993Assignee: The Mead CorporationInventors: Jesse Hipps, Sr., Michael S. Shanklin, Paul Davis
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Patent number: 5168032Abstract: The present invention relates to a photopolymerizable composition having a high sensitivity to visible light of 400 nm or longer and comprising a photopolymerization initiator consisting of:(a) a salt of an organic boron anionic compound with an organic and cationic dye or a combination of an organic and cationic dye with a salt of an organic boron anionic compound, and(b) a compound having the general formulae (I) to (VI) as defined in the present application.Type: GrantFiled: June 28, 1990Date of Patent: December 1, 1992Assignee: Fuji Photo Film Co., Ltd.Inventors: Yasuo Okamoto, Kouichi Kawamura
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Patent number: 5164278Abstract: Acid sensitized photoresists with enhanced photospeed are provided. The photoresist compositions include a polymer binder and/or a polymerizable compound and an acid sensitive group which enables patterning of the resist composition, and acid generating photoinitiator, and an hydroxy aromatic compound which enhances the speed of the resist composition under imaging radiation.Type: GrantFiled: March 1, 1990Date of Patent: November 17, 1992Assignee: International Business Machines CorporationInventors: William R. Brunsvold, Christopher J. Knors, Melvin W. Montgomery, Wayne M. Moreau, Kevin M. Welsh
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Patent number: 5153100Abstract: Photopolymerizable compositions in which the photoinitiator system contains a hexaarylbisimidazole and/or a p-dialkyaminophenyl carbonyl compound in combination with a borate anion coinitiator are disclosed.Type: GrantFiled: August 27, 1990Date of Patent: October 6, 1992Assignee: E. I. du Pont de Nemours and CompanyInventors: Gregory C. Weed, Dietrich Fabricius
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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
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Patent number: 5147758Abstract: Photopolymerizable compositions which comprise a borate anion, a squarylium sensitizer, and, in the preferred case, a halomethyl triazine are disclosed.Type: GrantFiled: February 19, 1991Date of Patent: September 15, 1992Assignee: E. I. Du Pont de Nemours and CompanyInventors: William K. Smothers, Gregory C. Weed, Evan D. Laganis, George Lalka
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Patent number: 5143818Abstract: This invention relates to initiator systems for photopolymerizable compositions. More particularly, this invention pertains to photopolymerizable compositions in which the initiator system comprises an anionic dye in combination with a borate anion coinitiator.Type: GrantFiled: February 1, 1991Date of Patent: September 1, 1992Assignee: E. I. Du Pont de Nemours and CompanyInventors: Gregory C. Weed, Bruce M. Monroe
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Patent number: 5141990Abstract: In-situ development of an ultraviolet absorber is provided by a compound such as a hydroxy-phenyl-triazole containing a group which protects the absorber during actinically activated polymerization by light at first frequency. After polymerization the protective group is removed by actinic reaction at a second frequency lower than the first frequency. The protective group is formed by replacing the hydrogen of the hydroxyl group with an acyl group containing 1 to 3 carbon atoms or an acryloxy group of the formula: ##STR1## where R.sup.1 is either an alkyl containing 1 to 6 carbon atoms or --CH.dbd.CH.sub.2.Type: GrantFiled: October 25, 1989Date of Patent: August 25, 1992Assignee: California Institute of TechnologyInventors: Vincent B. McKoy, Amitava Gupta
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Patent number: 5141969Abstract: Sulfonium, selenonium, arsonium, ammonium and phosphonium salts, useful as photoinitiators, comprise:a chromophore which absorbs visible radiation, the chromophore (1) having a removable positive hydrogen ion and (2) exhibiting a higher energy occupied molecular orbital than at least one other substituent attached to the S, Se, As, N or P atom of the salt;an insulating group which links the chromophore to the S, Se, As, N or P atom of the salt, the insulating group essentially preventing .pi. resonance between the chromophore and the other substituents in the salt;at least one substituent comprising an electron withdrawing group and exhibiting a lower unoccupied molecular orbital than the chromophore; and,an anion;the salts being capable, upon exposure to visible radiation, of forming a Bronsted acid.Type: GrantFiled: October 10, 1989Date of Patent: August 25, 1992Assignee: Eastman Kodak CompanyInventors: Franklin D. Saeva, David T. Breslin
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Patent number: 5130347Abstract: A dental cement system containing a photocurable ionomer, reactive powder and water undergoes both a conventional setting reaction and a photocuring reaction.The cement system can provide a long working time and can be cured on demand by exposure to an appropriate source of radiant energy. The surface of the cement cured in this manner is then hard enough to allow subsequent clinical procedures to be performed, while the ongoing chemical-cure "setting" reaction hardens the remainder of the cement.Type: GrantFiled: February 19, 1991Date of Patent: July 14, 1992Assignee: Minnesota Mining and Manufacturing CompanyInventor: Sumita B. Mitra
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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: 5100928Abstract: Described herein are photopolymerizable compositions comprising at least one polymerizable ethylenically unsaturated compound, and an initiating combination of an organic soluble xanthene dye compound and an organic activator compound. These compositions are useful as radiation-curable coatings, photocurable films, and photoactive films.Type: GrantFiled: April 18, 1990Date of Patent: March 31, 1992Assignee: Olin CorporationInventors: Paul V. Grosso, Willard F. Burt, Guilford Jones
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Patent number: 5098806Abstract: Rapid changes in absorption are made within the volume of a photosensitive transparent member that absorbs incident radiation to prevent the photocopy of a document, the original transparency being restored after discontinuance of the incident radiation.Type: GrantFiled: September 22, 1989Date of Patent: March 24, 1992Assignee: Board of Regents, The University of Texas SystemInventor: Jean J. Robillard
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Patent number: 5085974Abstract: A photopolymerizable mixture is disclosed which comprisesa) a polymeric binder,b) an acrylate or alkacrylate of a polyhydric alcohol containing one or more groups which are photooxidizable on exposure in the presence of the photoreducible dye, and one or more urethane groups,c) a photoreducible dye as photoinitiator.The mixture is suitable for the production of printing plates and photoresists and is distinguished by increased photosensitivity, which can be even further increased by the addition of a photolytically cleavable compound which contains at least one trihalomethyl group. A recording material comprising the photopolymerizable mixture is also disclosed.Type: GrantFiled: March 28, 1988Date of Patent: February 4, 1992Assignee: Hoechst AktiengesellschaftInventors: Werner Frass, Dieter Mohr, Klaus Rode
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Patent number: 5086086Abstract: A polymerizable composition comprises a polymeric precursor selected from the group consisting of 1) at least one ethylenically-unsaturated monomer, 2) at least one epoxy monomer, and 3) polyurethane precursors, and a curing agent comprising an organometallic compound and an onium salt.Type: GrantFiled: May 2, 1990Date of Patent: February 4, 1992Assignee: Minnesota Mining and Manufacturing CompanyInventors: Katherine A. Brown-Wensley, Robert J. DeVoe, Michael C. Palazzotto
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Patent number: 5073643Abstract: Synthesis use of a new class of diaryliodonium salt photo and thermal polymerization initiators in which the aryl groups are substituted with alkoxy group bearing hydroxy groups. Good to excellent yields are obtained of diaryliodonium salts in which the aryl groups are substituted with long chain alkoxy groups, which alkoxy groups also possess at least one hydroxyl moiety attached at the 2-position of an alkoxy group. The resultant salts have enhanced solubility when compared with their lower molecular weight counterparts. The hydroxyl groups serve as chain transfer agents; and, in cross linking UV-induced cationic polymerizations, the hydroxyl groups effect marked accelertion on polymerization rates. The salts also have excellent compatability with nonpolar monomers such as epoxidized oil and poly(1,2-butadience oxide) and provide further benefits when they are used along with copper cocatalysts in thermally curable polymer systems.Type: GrantFiled: August 30, 1990Date of Patent: December 17, 1991Assignee: Polyset CorporationInventor: James V. Crivello
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Patent number: 5066564Abstract: A photopolymerizable mixture is disclosed that comprises,a) a polymeric binder,b) an acrylate or alkacrylate of a polyhydric alcohol containing one or more urea groups and one or more urethane groups,c) a photoreducible dye as photoinitiator,d) a trihalomethyl compound which can be cleaved by irradiation, ande) an acridine or phenazine compound which is active as a photoinitiator.The mixture is suitable for the production of printing plates and photoresists and is distinguished by an increased shelf life.Type: GrantFiled: July 19, 1989Date of Patent: November 19, 1991Assignee: Hoechst AktiengesellschaftInventors: Rudolf Zertani, Dieter Mohr, Klaus Rode
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Patent number: 5059512Abstract: An ultraviolet light sensitive photoinitiator composition that includes at least one anthracene derivative represented by the formula: ##STR1## wherein X is CH.dbd.CH.sub.2 or --(--CH.sub.2 --)--.sub.n O--(--R) with R being H or ##STR2## wherein each R.sup.I, R.sup.II and R.sup.III individually is selected from the group of alkyl, alkenyl, aryl, ##STR3## wherein each R.sup.IV, R.sup.V and R.sup.VI individually is selected from the group of alkyl, alkenyl and aryl; wherein m is an integer of 0 to 4, p is an integer of 0 to 4; and is n being 1 to 2; and onium salt; and an organic solvent. The composition is used for cationic polymerization of cationic polymerizable materials including in the formation of a pattern of a photoresist. Also certain novel epoxy-functionalized organosilicons are provided that are sensitive to radiation including E-beam radiation and exhibit resistance to oxygen reactive ion etching.Type: GrantFiled: October 10, 1989Date of Patent: October 22, 1991Assignee: International Business Machines CorporationInventors: Edward D. Babich, Jeffrey D. Gelorme, Michael Hatzakis, Jane M. Shaw, Kevin J. Stewart, David F. Witman
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Patent number: 5057551Abstract: Adhesives containing some bifunctional and some at least trifunctional epoxide compounds, photoinitiators, and acrylates of methacrylates corresponding to general formulaCH.sub.2 =C(R.sup.1)-CO-(OC.sub.m H.sub.2m).sub.n -OR.sup.2in which R.sup.1 is hydrogen or methyl and R.sup.2 is a hydrocarbon radical containing a cationically cleavable oxacycloalkyl or oxacycloalkenyl group, continue to harden in darkness after their hardening has been photoinitiated, and thus can produce strong bonds between opaque substrates, when the substrates are coated with the adhesives, the adhesive coatings are exposed to light to initiate the hardening, and the coated substrates are pressed together within a short interval before the hardening of the photoinitiated adhesives advances to the gel point.Type: GrantFiled: March 2, 1989Date of Patent: October 15, 1991Assignee: Henkel Kommanditgesellschaft auf AktienInventors: Rene-Andres A. Gonzalez, Heinz-Christian Nicolaisen, Lothar Kammer
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Patent number: 5057393Abstract: The present invention is directed to a compound of the formula (I): ##STR1## where D+ is a cationic dye moiety; R.sup.1 is a branched chain alkyl group, and R.sup.2, R.sup.3 and R.sup.4 are independently selected from the group consisting of alkyl, aryl, aralkyl, alkaryl, alkenyl, alkynyl, alicyclic, heterocyclic, and allyl groups.Type: GrantFiled: July 10, 1989Date of Patent: October 15, 1991Assignee: The Mead CorporationInventors: Michael S. Shanklin, Peter Gottschalk
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Patent number: 5055376Abstract: Compositions of matter are provided which comprise a material curable by a Bronsted acid, and a photoinitiator salt having the formula: ##STR1## wherein: R.sup.1 represents an electron-donating chromophore group which absorbs visible radiation and which exhibits a higher energy occupied molecular orbital than at least one of R", R'" and R"";R" represents the same substituent as R' or R'", an optionally substituted aryl group or an optionally substituted alkyl group having from 1 to 18 carbon atoms;R'" represents an electron-withdrawing alkyl, aryl or heterocyclic group;R.sub.1 and R.sub.2 each, independently, represents hydrogen or an electron-donating group;J represents an S, Se, As, N or P atom; andwhen J represents As, N or P, R"" represents the same substituent as R', R" or R'", and when J represents an S or Se atom, R"" represents O or an electron pair; andW.sup..THETA.Type: GrantFiled: November 13, 1990Date of Patent: October 8, 1991Assignee: Eastman Kodak CompanyInventor: Franklin D. Saeva
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Patent number: 5055372Abstract: A photohardenable composition comprising a free radical addition polymerizable or crosslinkable compound and an aromatic ketone and a borate salt; and photosensitive materials employing the composition where in one embodiment the composition is microencapsulated.Type: GrantFiled: April 23, 1990Date of Patent: October 8, 1991Assignee: The Mead CorporationInventors: Michael S. Shanklin, Peter Gottschalk, Paul C. Adair
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Patent number: 5049479Abstract: A photopolymerizable mixture is described which comprises a polymeric binder, a free-radically polymerizable compound having at least one polymerizable group, a photoreducible dye, a trihalomethyl compound which can be cleaved by radiation and a metallocene compound as photoinitiators. The mixture is suitable for use in the production of printing plates and photoresists and is characterized by a particularly high photosensitivity, especially in the visible spectral region. The mixture can therefore be used for the production of images, in particular by means of laser radiation in the visible region.Type: GrantFiled: September 21, 1989Date of Patent: September 17, 1991Assignee: Hoechst AktiengesellschaftInventors: Rudolf Zertani, Dieter Mohr
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Patent number: 5043249Abstract: A photopolymerizable mixture is described comprising (a) a polymeric binder, (b) an acrylate or alkacrylate of a polyhydric alcohol, said compound being free of urethane groups and further comprising at least one group which is photooxidizable on exposure to actinic radiation in the presence of a photoreducible dye, (c) a photoinitiator comprising a photoreducible dye, (d) a second photoinitiator comprising a trihalomethyl compound capable of being cleaved by irradiation, and (e) a third photoinitiator comprising an acridine, phenazine or quinoxaline compound. The mixture is suitable for the production of printing plates and photoresists and displays increased photosensitivity.Type: GrantFiled: December 21, 1988Date of Patent: August 27, 1991Assignee: Hoechst AktiengesellschaftInventors: Klaus Rode, Joachim Gersdorf, Dieter Mohr, Werner Frass
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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: 5019481Abstract: An aqueous base developable negative resist composition comprising a phenolic resin, a radio-chemical acid generator and a small molecule which upon irradication and postbake reacts with the phenolic resin to decrease its rate of dissolution.Type: GrantFiled: September 25, 1989Date of Patent: May 28, 1991Assignee: International Business Machines CorporationInventor: Hiroshi Ito
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Patent number: 4987055Abstract: A photopolymerizable mixture is described comprising (a) a polymeric binder, (b) an acrylate or alkacrylate of a polyhydric alcohol, said compound comprising at least one group which is photooxidizable on exposure to actinic radiation in the presence of a photoreduciable dye, (c) a photoinitiator comprising a photoreducible benzoxanthene or benzothioxanthene dye, and (d) a second photoinitiator comprising a trihalomethyl compound capable of being cleaved by irradiation. The mixture is suitable for the production of printing plates and photoresists and displays increased photosensitivity.Type: GrantFiled: December 21, 1988Date of Patent: January 22, 1991Assignee: Hoechst AktiengesellschaftInventors: Klaus Rode, Dieter Mohr, Werner Frass, Joachim Gersdorf
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Patent number: 4985341Abstract: A photopolymerizable composition is described comprising (a) a polymeric binder, (b) an acrylate or alkacrylate of a polyhydric alcohol, said acrylate or alkacrylate being free of urethane groups and further comprising at least one group which is photooxidizable on exposure to actinic radiation in the presence of a photoreducible dye, (c) a photoinitiator comprising a photoreducible dye, and (d) a second photoinitiator comprising a trihalomethyl compound capable of being cleaved by irradiation. The composition is suitable for production of printing plates and photoresists and displays increased photosensitivity.Type: GrantFiled: December 21, 1988Date of Patent: January 15, 1991Assignee: Hoechst AktiengesellschaftInventors: Klaus Rode, Dieter Mohr, Werner Frass, Joachim Gersdorf
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Patent number: 4985340Abstract: A polymerizable composition comprises a polymeric precursor selected from the group consisting of (1) at least one ethylenically-unsaturated monomer, optionally in combination with an epoxy monomer or polyurethane precursors, or (2) at least one epoxy monomer, or (3) polyurethane precursors, and a curing agent comprising an organometallic salt and an onium salt.Type: GrantFiled: June 1, 1988Date of Patent: January 15, 1991Assignee: Minnesota Mining and Manufacturing CompanyInventors: Michael C. Palazzotto, Robert J. DeVoe
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Patent number: 4983498Abstract: A photopolymerizable mixture is disclosed comprising:(a) a polymeric binder,(b) an acrylate or alkacrylate of a polyhydric alcohol containing one or more groups which are photooxidizable on exposure in the presence of the photoreducible dye, and one or more urethane groups,(c) a photoreducible dye as photoinitiator,(d) a trihalomethyl compound which can be cleaved by irradiation, and(e) 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 increased photosensitivity.Type: GrantFiled: March 23, 1988Date of Patent: January 8, 1991Assignee: Hoechst AktiengesellschaftInventors: Klaus Rode, Dieter Mohr, Werner Frass
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Patent number: 4980266Abstract: A photosensitive resin composition comprising (A) a carboxyl group-containing film-forming property imparting polymer, (B) a copolymerizable vinyl compound, (C) a photopolymerization initiator, and (D) a 1,2,3-benzotriazole derivative is useful for forming a photosensitive film excellent in resistance to plating and stability.Type: GrantFiled: May 15, 1990Date of Patent: December 25, 1990Assignee: Hitachi Chemical Company, Ltd.Inventors: Taku Kawaguchi, Yoshitaka Minami, Tatsuya Ichikawa
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Patent number: 4977198Abstract: Epoxy functional organopolysiloxanes are compatibilized with onium salt photocatalysts by modifying a controlled number of epoxy groups by esterification with carboxylic acids.Type: GrantFiled: March 21, 1988Date of Patent: December 11, 1990Assignee: General Electric CompanyInventor: Richard P. Eckberg
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Patent number: 4975471Abstract: A photo-curable epoxy resin type composition which comprises (a) an epoxy resin, (b) at least one compound selected from the group consisting of (i) a compound having a group, other than an imido group, which is represented by the formula --CONH and (ii) an aromatic amine, (c) an organic metal compound, where said metal is selected from the group consisting of titanium, vanadium, chromium, manganese, iron, cobalt, nickel, copper, zinc, aluminum and zirconium; and (d) an organic silicon compound having at least one group selected from the group consisting of a peroxysilyl group and an o-nitrobenzyloxy group capable of forming a silanol group by irradiation with light. The photo-curable epoxy resin type composition according to this invention is capable of readily curing by light (ultraviolet ray in particular) and also capable of heat curing at a temperature of 150.degree. C.Type: GrantFiled: August 29, 1988Date of Patent: December 4, 1990Assignee: Kabushiki Kaisha ToshibaInventors: Shuzi Hayase, Shuichi Suzuki, Moriyasu Wada
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Patent number: 4971892Abstract: A high speed visible light sensitive photopolymerizable composition useful for printing plates comprising(a) at least one free radically polymerizable monomer having at least one ethylenically unsaturated group,(b) an ethylenically unsaturated free radically polymerizable oligomer having carboxyl groups substituted thereon,(c) a visible light sensitizing initiator system for free radical polymerization comprising an initiator selected from diaryl iodonium salts, halogenated triazines, and triaryl iodonium salts which are photoinitiating electron acceptor compounds having a reduction potential in the range 0.0 to -1.5 eV, spectrally sensititzed with at least one merocyanine sensitizer containing a constrained alkylamino group, preferably a julolidinyl group.Type: GrantFiled: October 26, 1989Date of Patent: November 20, 1990Assignee: Minnesota Mining and Manufacturing CompanyInventors: Mohammad Z. Ali, Stanley C. Busman
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Patent number: 4971891Abstract: Disclosed is a photopolymerizable composition comprising (i) a monomer having at least one ethylenic unsaturated group which is polymerizable by means of active light, (ii) an organoboron compound, and (iii) a pyrylium or thiopyrylium dye. The composition is useful, for example, as photosensitive layers for photosensitive printing plates which are sensitive and respond to an argon laser light source.Type: GrantFiled: October 12, 1988Date of Patent: November 20, 1990Assignee: Fuji Photo Film Co., Ltd.Inventors: Koichi Kawamura, Yasuo Okamoto
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Patent number: 4966922Abstract: A silicone polymer substituted with both hydrolyzable leaving groups and epoxy groups is catalyzed with condensation cure catalyst and onium salt photoinitiator to produce a dual curable composition.Type: GrantFiled: June 9, 1988Date of Patent: October 30, 1990Assignee: General Electric CompanyInventors: David C. Gross, Gary M. Lucas
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Patent number: 4962011Abstract: Novel photopolymerizable recording materials suitable in particular for producing photoresist layers and lithographic printing plates are composed of one or more photopolymerizable, olefinically unsaturated organic compounds, optionally a polymeric binder, a photopolymerization initiator, a color-forming system composed of a color former and a photooxidant, a certain benzotriazole compound as a sensitizer and optionally further additive and/or auxiliary substances.Type: GrantFiled: May 17, 1988Date of Patent: October 9, 1990Assignee: BASF AktiengesellschaftInventors: Reinhard Aldag, Peter Neumann, Andreas Boettcher, Thomas Bluemel, Friedrich Seitz
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Patent number: 4959297Abstract: Photopolymerizable compositions comprising:(1) at least one vinyl monomer capable of undergoing free radical polymerization,(2) a visible light or ultraviolet light responsive photoinitiator system comprising:(a) a diaryliodonium salt,(b) a pigment, insoluble in the photopolymerizable composition, said pigment also serving as a sensitizer,(c) one or more electron donating compounds, and, optionally,(3) adjuvants.The three component photoinitiator system of this invention can increase, by several orders of magnitude, the rate of ultraviolet light or visible light photocuring of vinyl monomers.Type: GrantFiled: November 22, 1989Date of Patent: September 25, 1990Assignee: Minnesota Mining and Manufacturing CompanyInventor: Michael C. Palazzotto
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Patent number: 4954415Abstract: A photoinitiator composition comprising a compound which absorbs actinic radiation and directly or indirectly generates free radicals, and an O-acylthiohydroxamate compound or an N-alkoxypyridine thione; photohardenable compositions containing that photoinitiator composition; and photosensitive materials employing same.Type: GrantFiled: March 9, 1989Date of Patent: September 4, 1990Assignee: The Mead CorporationInventors: Paul D. Davis, Gary B. Schuster, Jacqueline G. Truini, Al Fentiman
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Patent number: 4954416Abstract: Free radical polymerizable compositions contain a sulfonium salt which is tethered to at least one of an electron donor and a sensitizer, and a polymerizable monomer, demonstrate substantially enhanced photosensitivity. This invention also provides layered structures comprising a substrate coated with a free radical polymerizable composition containing a sulfonium salt which is tethered to at least one of an electron donor and a sensitizer, and the polymerized layered structures. A method for the preparation of certain tethered sulfonium salts is described.Type: GrantFiled: December 21, 1988Date of Patent: September 4, 1990Assignee: Minnesota Mining and Manufacturing CompanyInventors: Bradford B. Wright, Robert J. DeVoe
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Patent number: 4952612Abstract: A polymerizable composition comprises a polymeric precursor selected from the group consisting of (1) at least one ethylenically-unsaturated monomer, (2) at least one epoxy monomer, and (3) polyurethane precursors, and a curing agent comprising an organometallic compound and an onium salt.Type: GrantFiled: August 28, 1987Date of Patent: August 28, 1990Assignee: Minnesota Mining and Manufacturing CompanyInventors: Katherine A. Brown-Wensley, Robert J. Devoe, Michael C. Palazzotto
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Patent number: 4950696Abstract: 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: August 28, 1987Date of Patent: August 21, 1990Assignee: Minnesota Mining and Manufacturing CompanyInventors: Michael C. Palazotto, Katherine A. Brown-Wensley, Robert J. DeVoe
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Patent number: 4950581Abstract: A photopolymerizable composition is provided containing a polymerizable compound having an ethylenically unsaturated bond, a photopolymerization initiator, and if necessary, a linear organic high molecular weight polymer. The photopolymerization initiator comprises a combination of (a) an organic compound represented by formula (I): ##STR1## wherein R.sup.1, R.sup.2, R.sup.3, and R.sup.4, which may be the same or different, each represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted alkenyl group a substituted or unsubstituted alkynyl group, or a substituted or unsubstituted heterocyclic group, and at least two of said R.sup.1, R.sup.2, R.sup.3, and R.sup.4 may combine to form a cyclic structure, with the proviso that at least one of R.sup.1, R.sup.2, R.sup.3, and R.sup.4 is an alkyl group, and wherein Z.sym. represents an alkali metal cation or a quaternary ammonium cation, and (b) an organic dye having no counter anion.Type: GrantFiled: July 5, 1988Date of Patent: August 21, 1990Assignee: Fuji Photo Film Co., Ltd.Inventors: Mitsuru Koike, Nobuyuki Kita
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Patent number: 4940649Abstract: Novel photopolymerizable recording materials suitable in particular for producing photoresist layers and lithographic printing plates are composed of one or more photopolymerizable, olefinically unsaturated organic compounds, optionally a polymeric binder, a photopolymerization initiator, a color-forming system composed of a color former and a photooxidant, a certain 4-phenylpyridine as sensitizer and optionally further additive and/or auxiliary substances.Type: GrantFiled: May 17, 1988Date of Patent: July 10, 1990Assignee: BASF AktiengesellschaftInventors: Reinhard Aldag, Peter Neumann, Andreas Boettcher, Thomas Bluemel, Friedrich Seitz, Friedrich-Wilhelm Raulfs