Containing Ethylenic Unsaturation Patents (Class 522/34)
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Patent number: 5629356Abstract: Compounds of the formula I, II, III and IIIa ##STR1## in which Ar.sup.1 is an unsubstituted or substituted aromatic radical and at least one of the radicals R.sup.1 and R.sup.2 is an alkenyl, cycloalkenyl or arylmethyl group, are effective photoinitiators for photopolymerization of unsaturated compounds. They are particularly suitable for photocuring of pigmented systems.Type: GrantFiled: March 12, 1996Date of Patent: May 13, 1997Assignee: Ciba Geigy CorporationInventors: Vincent Desobry, Kurt Dietliker, Rinaldo H usler, Werner Rutsch, Manfred Rembold, Franciszek Sitek
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Patent number: 5554663Abstract: Compounds of the formula I, II, III and IIIa ##STR1## in which Ar.sup.1 is an unsubstituted or substituted aromatic radical and at least one of the radicals R.sup.1 and R.sup.2 is an alkenyl, cycloalkenyl or arylmethyl group, are effective photoinitiators for photopolymerization of unsaturated compounds. They are particularly suitable for photocuring of pigmented systems.Type: GrantFiled: June 6, 1995Date of Patent: September 10, 1996Assignee: Ciba-Geigy CorporationInventors: Vincent Desobry, Kurt Dietliker, Rinaldo H usler, Werner Rutsch, Manfred Rembold, Franciszek Sitek
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Patent number: 5534629Abstract: Compounds of the formula I, II, III and IIIa ##STR1## in which Ar.sup.1 is an unsubstituted or substituted aromatic radical and at least one of the radicals R.sup.1 and R.sup.2 is an alkenyl, cycloalkenyl or arylmethyl group, are effective photoinitiators for photopolymerization of unsaturated compounds. They are particularly suitable for photocuring of pigmented systems.Type: GrantFiled: May 1, 1995Date of Patent: July 9, 1996Assignee: Ciba-Geigy CorporationInventors: Vincent Desobry, Kurt Dietliker, Rinaldo Husler, Werner Rutsch, Manfred Rembold, Franciszek Sitek
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Patent number: 5532112Abstract: Compounds of the formulaRG--A--INwhereinIN is a photoinitiator basic structureA is a spacer group andRG is a functional reactive groupcan be employed as coreactive photoinitiators for photopolymerization of systems containing ethylenically unsaturated compounds.Type: GrantFiled: June 2, 1994Date of Patent: July 2, 1996Assignee: Ciba-Geigy CorporationInventors: Manfred Kohler, Jorg Ohngemach, Eike Poetsch, Rudolf Eidenschink, Gerhard Greber, Dieter Dorsch, Jurgen Gehlhaus, Konrad Dorfner, Hans L. Hirsch
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Patent number: 5506279Abstract: The invention provides novel acrylamide functional disubstituted acetyl aryl ketones and a process for their preparation in high yields uncontaminated by difunctional material. The invention further provides photocrosslinkable compositions comprising one or more ethylenically-unsaturated monomers and as photoinitiator the acrylamide functional disubstituted acetyl aryl ketone of the invention. The compositions are useful for the preparation of films and coatings, particularly pressure-sensitive adhesive coatings.Type: GrantFiled: May 3, 1994Date of Patent: April 9, 1996Assignee: Minnesota Mining and Manufacturing CompanyInventors: Gaddam N. Babu, Greggory S. Bennett, Kejian Chen, Steven M. Heilmann, Howell K. Smith, II, Louis E. Winslow
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Patent number: 5484821Abstract: A novel photocrosslinkable polymeric system has been developed for processing into films having stable second-order nonlinear optical properties. In the present system, polymers bearing photo-crosslinkable chromophores, such as polyvinylcinnamate and are reacted with appropriately designed nonlinear optical molecules with the cinnamate or other photocrosslinkable functionalities for photocrosslinking at one, two or more points. The system can be poled and photocrosslinked in the poled state to yield a material with stable optical nonlinearity and large electro-optic coefficients.Type: GrantFiled: February 7, 1994Date of Patent: January 16, 1996Assignee: University of LowellInventors: Braja K. Mandal, Sukant K. Tripathy, Jan-Chan Huang, Jayant Kumar
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Patent number: 5474876Abstract: A radiation-crosslinkable mixture which contains a carboxyl-containing precursor of a heterocyclic polymer, a copolymerizable ethylenically unsaturated ternary sulfonium salt, a photoinitiator and a polar aprotic organic solvent.Type: GrantFiled: October 5, 1994Date of Patent: December 12, 1995Assignee: BASF Lacke + Farben AGInventors: Hans-Joachim Haehnle, Manfred Schwarz, Rainer Blum
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Patent number: 5466721Abstract: Provided are compounds having the formula: ##STR1## wherein: R.sup.1 and R.sup.2 are independently selected from the group consisting of a hydrogen atom, an aliphatic group, a hetero-aliphatic group, an aromatic group, and a heterocyclic group, provided that R.sup.1 and R.sup.2 may together form a divalent radical selected from the group consisting of an aliphatic radical and hetero-aliphatic group;each R.sup.3 is independently selected from the group consisting of an aliphatic group, a hetero-aliphatic group, an aromatic group, and a heterocyclic group;R.sup.4 is selected from the group consisting of an aliphatic group, a hetero-aliphatic group, an aromatic group, and a heterocyclic group; andn is an integer from 0 to 5.Also provided are polymerizable compositions containing such compounds and a method of coating a substrate which uses such polymerizable compositions.Type: GrantFiled: June 13, 1994Date of Patent: November 14, 1995Assignee: Henkel CorporationInventor: Paul E. Share
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Patent number: 5455143Abstract: Aminoketone-substituted coumarin sensitizers having quaternary amine substituents are described which have very high photosensitivity, and are useful in moderate pH aqueous-developable printing plates. The aminoketone-substituted coumarin sensitizers are described by 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 16 carbon atoms, an oxyalkylene group having form 1 to 16 carbon atoms, or a poly(oxyalkylene) group in which said alkylene group has 2 to 4 carbon atoms and the number of oxygen atoms is a positive integer less than or equal to four,R.sub.7, R.sub.8, and R.sub.9 each independently represent an alkyl group having 1 to 6 carbon atoms, or any two of R.sub.Type: GrantFiled: April 28, 1994Date of Patent: October 3, 1995Assignee: Minnesota Mining and Manufacturing CompanyInventor: M. Zaki Ali
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Patent number: 5437932Abstract: Novel photosensitive compositions based on azlactone derived polymers are described. The polymers have a hydroearbyl backbone and pendant peptide groups with free-radically polymerizable functionality attached thereto, said polymer further comprising at least one oxyacid group or salt thereof, and optionally quaternary ammonium salt groups. A high speed durable printing plate having a mild pH aqueous developability is disclosed which incorporates these polymers in combination with a photoinitiator. The polymers are also useful as proofing films in graphic arts applications.Type: GrantFiled: May 13, 1994Date of Patent: August 1, 1995Assignee: Minnesota Mining and Manufacturing CompanyInventors: M. Zaki Ali, Mahfuza B. Ali, Dean M. Moren
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Patent number: 5405888Abstract: A photocurable and moisture-curable silione composition comprising a reactive organosilane which has acryldialkoxysilyl or acryldiallyloxysilyl groups at both ends, a silicone oil, a photosensitizer and a moisture-curing catalyst.Type: GrantFiled: December 28, 1993Date of Patent: April 11, 1995Assignee: Three Bond Co, Ltd.Inventor: Toru Takeoka
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Patent number: 5389699Abstract: UV-crosslinkable materials based on (meth)acrylate copolymers and containing from 0.01 to 10% by weight, based on the copolymer, of copolymerized monomers of the formula I ##STR1## where x is alkyl of 1 to 3 carbon atoms or is phenyl which is unsubstituted or substituted by n Y groups, Y is --H, --CF.sub.3, --O-- alkyl and/or alkyl-COO--, where alkyl in each case is of 1 to 4 carbon atoms, halogen, --CH, --COOH or a non-ortho --OH group, n is from 0 to 4 and Z is a group of the formula ##STR2## where R is H or C.sub.1 -C.sub.4 -alkyl and A is an alkylene, oxaalkylene or polyoxaalkylene radical of 2 to 12 carbon atoms are used as hotmelt adhesives, for coating sheet-like mineral substrates and as surface coatings.Type: GrantFiled: July 8, 1993Date of Patent: February 14, 1995Assignee: BASF AktiengesellschaftInventors: Gerd Rehmer, Andreas Boettcher, Michael Portugall
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Patent number: 5362603Abstract: The present invention relates to a photopolymerizable composition containing a photopolymerizable compound having at least one ethylenically unsaturated double bond, a photopolymerization initiator, a pigment and optionally another resin, wherein said photopolymerizable compound contained therein comprises not less than 60%.Type: GrantFiled: February 24, 1993Date of Patent: November 8, 1994Assignee: Nippon Kayaku Kabushiki KaishaInventors: Yoshinori Katoh, Naoko Ichinose, Teruhito Sotogoshi
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Patent number: 5314930Abstract: Novel ketone monomers containing both alpha-beta unsaturated acylate and unsaturated fatty acylate substituents on more carbon atoms beta to the carbonyl group (Formula 1) have been found to be surprisingly useful in a variety of essentially pollution free coatings applications.a,b,cCC(0)Cd,e,f Formula IWherein not less than one, but no more than three of a,b,d and e are each independently chosen from among monovalent ligands having the structure --CH.sub.2,O.sub.2 CCR.dbd.CR'R" (wherein each of R,R', and R" is independently chosen from among hydrogen, methyl or ethyl ligands); and wherein at least one, but not more than three of a,b,d and e are each independently chosen from among monovalent ligands having the structure: --CH.sub.2 O.sub.2 CC.sub.n H.sub.Type: GrantFiled: April 5, 1993Date of Patent: May 24, 1994Inventor: Gerald Sugerman
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Patent number: 5290824Abstract: A novel photocrosslinkable polymeric system has been developed for processing into films having stable second-order nonlinear optical properties. In the present system, polymers bearing photo-crosslinkable chromophores, such as polyvinylcinnamate and are reacted with appropriately designed nonlinear optical molecules with the cinnamate or other photocrosslinkable functionalities for photocrosslinking at one, two or more points. The system can be poled and photocrosslinked in the poled state to yield a material with stable optical nonlinearity and large electro-optic coefficients.Type: GrantFiled: May 12, 1992Date of Patent: March 1, 1994Assignee: University of LowellInventors: Braja K. Mandal, Sukant K. Tripathy, Jan-Chuan Huang, Jayant Kumar
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Patent number: 5264533Abstract: UV-crosslinkable materials based on (meth)acrylate copolymers and containing special modified unsaturated benzophenone derivatives as copolymerized units are used as hotmelt adhesives, for coating sheet-like mineral substrates and as surface coatings.Type: GrantFiled: August 1, 1991Date of Patent: November 23, 1993Assignee: BASF AktiengesellschaftInventors: Gerd Rehmer, Andreas Boettcher, Michael Portugall
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Patent number: 5262276Abstract: A light-sensitive composition which comprises at least one compound represented by the following general formula (I) as light-free radical generator:S-L-A (I)in formula (I), S represents a light absorbing moiety which absorbs light having a wave length of not less than 300 nm with an absorptivity coefficient of not less than 1000, A represents an active moiety which interacts with the light absorbing moiety S in an excited state to generate free radicals and L represents a group for coupling the moieties S and A; and a photopolymerizable composition which comprises at least one radical polymerizable compound having ethylenically unsaturated group, at least one compound represented by the foregoing general formula (I) as a light-free radical generator and optionally at least one linear organic high molecular weight polymer.Type: GrantFiled: May 10, 1989Date of Patent: November 16, 1993Assignee: Fuji Photo Film Co., Ltd.Inventor: Kouichi Kawamura
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Patent number: 5238782Abstract: A photopolymerizable composition comprises at least one addition polymerizable compound having at least one ethylenically unsaturated bond and at least one photopolymerization initiator represented by the following general formula (I): ##STR1## wherein R.sub.1 to R.sub.4 independently represent hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, hydroxyl group, a substituted or unsubstituted alkoxy group, or a substituted or unsubstituted amino group with the proviso that R.sub.1 to R.sub.4 may form a non-metallic ring together with the carbon atoms bonded thereto; R.sub.5 and R.sub.6 each represents hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a heteroaromatic group, an acyl group, cyano group, an alkoxycarbonyl group, carboxyl group or a substituted alkenyl group with the proviso that R.sub.5 and R.sub.Type: GrantFiled: February 26, 1990Date of Patent: August 24, 1993Assignee: Fuji Photo Film Co., Ltd.Inventors: Koichi Kawamura, Mitsuru Koike
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Patent number: 5235015Abstract: Novel photosensitive compositions based on azlactone derived polymers are described. The polymers have a hydrocarbyl backbone and pendant peptide groups with free-radically polymerizable functionality attached thereto, said polymer further comprising at least one oxyacid group or salt thereof, and optionally quaternary ammonium salt groups. A high speed durable printing plate having a mild pH aqueous developability is disclosed which incorporates these polymers in combination with a photoinitiator. The polymers are also useful as proofing films in graphic arts applications.Type: GrantFiled: February 21, 1991Date of Patent: August 10, 1993Assignee: Minnesota Mining and Manufacturing CompanyInventors: M. Zaki Ali, Mahfuza B. Ali, Dean M. Moren
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Patent number: 5202221Abstract: The present invention relates to a light-sensitive composition comprising (a) a photo-crosslinkable polymer having a maleimido group at a side chain and (b) a sensitizer such as the following compounds: ##STR1## The present invention provides a light-sensitive composition having very high sensitivity; providing excellent images during only a short exposure time; and being sensitive to light of long wave length.Type: GrantFiled: November 9, 1989Date of Patent: April 13, 1993Assignee: Fuji Photo Film Co., Ltd.Inventors: Masanori Imai, Noriaki Watanabe, Kouichi Kawamura
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Patent number: 5198325Abstract: A photopolymerizable mixture for producing relief structures composed of highly heat-resistant polymers is described which is composed essentially of a soluble prepolymer containing photosensitive radicals bound in an ester-like manner to carboxyl groups, monomers and a photoinitiator, wherein the photoinitiator carries at least one trihalomethyl group which reacts when exposed to light. Of advantage is the fact that, even after exposure times which are by a factor of 4 to 5 shorter compared with conventional photopolymerizable mixtures, sharp-edged resist images can be obtained with a resolution of less than 3 .mu.m.Type: GrantFiled: May 26, 1988Date of Patent: March 30, 1993Assignee: Hoechst AktiengesellschaftInventors: Bernd Hupfer, Gerhard Buhr, Charlotte Eckes
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Patent number: 5187045Abstract: Radiation-sensitive organo-halogen compounds having a photo-labile halomethyl-1,3,5-triazine moiety and at least one sensitizer moiety within one molecule. The compounds of this invention are good photoinitiators, and compositions containing them can be used in printing, duplicating, copying, and other imaging systems.Type: GrantFiled: June 4, 1991Date of Patent: February 16, 1993Assignee: Minnesota Mining and Manufacturing CompanyInventors: James A. Bonham, Mitchell A. Rossman
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Patent number: 5145884Abstract: An ultraviolet-hardenable adhesive for bonding a non-water swellable, ophthalmic-lens to a support member, in producing a non-water swellable ophthalmic lens, the adhesive containing at least one photopolymerizing monomer, and at least one photoinitiator, the at least one photopolymerizing monomer being selected from the group consisting of acrylates or methacrylates represented by following general formulas (I) and (II): ##STR1## wherein R.sub.1 is hydrogen or methyl,R.sub.2 is hydrogen or methyl,R.sub.3 is hydrogen or methyl,m is a positive integer from 2 to 20, andn is a positive integer from 1 to 5.A method of bonding a lens blank to a support member with an adhesive, and a processing of manufacturing a lens using an adhesive, are also disclosed.Type: GrantFiled: August 16, 1990Date of Patent: September 8, 1992Assignee: Menicon Co., Ltd.Inventors: Yasuyoshi Yamamoto, Yuzo Kaga, Toshiharu Yoshikawa, Akira Moribe
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Patent number: 5141841Abstract: A radiation-sensitive compound has the general formula ##STR1## wherein A represents the ring members required to complete a 5- or 6-membered heterocyclic ring which may optionally be fused to an optionally substituted aromatic nucleus,B represents H, acyl, aroyl, heterocyclyl carbonyl or ##STR2## R represents an optionally substituted alkyl group, E and G, which may be the same or different, each represents H or CH.sub.p X.sub.3-p,J and K, which may be the same or different, each represents an aryl or heterocyclic group, which may optionally include a substituent additional to E or G,X represents Cl or Br, and m,n and p, which may be the same or different, each represents an integer equal to 0, 1 or 2.The compound can be used to form radiation sensitive compositions for the production of radiation sensitive plates in lithographic printing plate manufacture.Type: GrantFiled: August 17, 1989Date of Patent: August 25, 1992Assignee: Vickers PLCInventor: John R. Wade
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Patent number: 5130227Abstract: A radiation sensitive plate comprises a substrate coated with a photopolymerizable composition. The composition comprises a polymerizable compound containing ethylenic unsaturation, a perester photoinitiator and optionally an optical sensitiser. The substrate may be a sheet of grained and anodized aluminum and the plate is useful in the production of lithographic printing plates.Type: GrantFiled: October 5, 1989Date of Patent: July 14, 1992Assignee: Vickers PlcInventors: John R. Wade, Rodney M. Potts, Michael J. Pratt
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Patent number: 5118779Abstract: A non-toxic hydrophilic polyurethane elastomer having less than about 0.5% by weight extractables and which is curable in the absence of heat is disclosed. The elastomers are prepared from suitable hydrophilic polyurethane oligomers in combination with suitable ultraviolet light absorbers which become chemically bound into the elastomer during the polymerization (curing) thereof and thus become essentially non-extractable therefrom.Type: GrantFiled: October 10, 1989Date of Patent: June 2, 1992Assignee: PolyMedica Industries, Inc.Inventor: Michael Szycher
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Patent number: 5112881Abstract: A novel photocrosslinkable polymeric system has been developed for processing into films having stable second-order nonlinear optical properties. In the present system, polymers bearing photocrosslinkable chromophores, such as polyvinylcinnamate and are reacted with appropriately designed nonlinear optical molecules with the cinnamate or other photocrosslinkable functionalities for photocrosslinking at one, two or more points. The system can be poled and photocrosslinked in the poled state to yield a material with stable optical nonlinearity and large electro-optic coefficients.Type: GrantFiled: August 24, 1990Date of Patent: May 12, 1992Assignee: University of LowellInventors: Braja K. Mandal, Sukant K. Tripathy, Jan-Chan Huang, Jayant Kumar
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Patent number: 5077402Abstract: Compounds of the formula I, II, III and IIIa ##STR1## in which Ar.sup.1 is an unsubstituted or substituted aromatic radical and at least one of the radicals R.sup.1 and R.sup.2 is an alkenyl, cycloalkenyl or arylmethyl group, are effective photoinitiators for photopolymerization of unsaturated compounds. They are particularly suitable for photocuring of pigmented systems.Type: GrantFiled: March 28, 1990Date of Patent: December 31, 1991Assignee: Ciba-Geigy CorporationInventors: Vincent Desobry, Kurt Dietliker, Rinaldo Husler, Werner Rutsch, Manfred Rembold, Franciszek Sitek
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Patent number: 5073611Abstract: Copolymers which are curable by ultraviolet radiation in the air are prepared by a process in which a mixture of (A) from 80 to 99.9% by weight of olefinically unsaturated monomers, (B) from 0 to 10% by weight of a copolymerizable olefinically unsaturated, photoreactive compound which, in the excited state produced by UV radiation, is capable of abstracting hydrogen and (C) from 0 to 10% by weight of a polymerization-regulating photoreactive compound which, in the excited state, is capable of abstracting hydrogen is subjected to free radical polymerization, the sum of (B) and (C) being not less than 0.1% by weight and the stated percentages by weight being based on the sum of the weights of (A)+(B)+(C).Type: GrantFiled: April 29, 1991Date of Patent: December 17, 1991Assignee: BASF AktiengesellschaftInventors: Gerd Rehmer, Andreas Boettcher
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Patent number: 5071888Abstract: Photopolymerizable prepolymer compositions are provided comprising an unsaturated compound having at least one ethylenic double bond that is photopolymerizable to form a polymer, and a photoinitiator having one of the formulae: ##STR1##Type: GrantFiled: July 8, 1985Date of Patent: December 10, 1991Assignee: Asahi Denka Kogyo K.K.Inventor: Naohiro Kubota
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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: 5032488Abstract: When irradiated, a mixture of (a) a non-volatile substance containing at least one olefinic double bond and (b) a dibenzalacetone palladium complex deposits zero-valent palladium. Electrically non-conductive carrier materials which have been coated with a layer of said mixture can, after irradiation, be metallized by metal deposition without current, with electrically conductive coatings or patterns being obtained.Type: GrantFiled: March 1, 1988Date of Patent: July 16, 1991Assignee: Ciba-Geigy CorporationInventor: Jurgen Finter
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Patent number: 5026740Abstract: The invention relates to the use of a new class of sulphurated derivatives of aromatic-aliphatic or aliphatic ketones as a) polymerization or crosslinking photoinitiators for transparent or pigmented mixtures containing ethylenically unsaturated photopolymerizable compounds, in particular for obtaining polyacrylates, b) photochemically releasable latent acid catalysts, useful for crosslinking systems polycondensable by acid catalysis, of the type comprising etherified aminoplasts together with compounds containing hydroxyl, carboxyl, amido, amino and other functionalities.Said sulphurated derivatives enable manufactured articles to be obtained with exceptionally clear color while maintaining photochemical reactivity at high levels.Type: GrantFiled: July 15, 1988Date of Patent: June 25, 1991Assignee: Fratelli Lamberti S.p.A.Inventors: Giuseppe Li Bassi, Luciano Cadona, Carlo Nicora
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Patent number: 5002853Abstract: The present invention relates to a positive working photosensitive composition having an improved sensitivity due to the use of a sensitizer and having an excellent incandescent light safety. This composition comprises at least 1 molar % of a structural unit derived from at least one of monomers having the following general formulae: ##STR1## wherein: R.sub.1 represents a hydrogen atom, an alkyl group or a substituted alkyl group,R.sub.2 represents a divalent alkylene group or a substituted divalent alkylene group,R.sub.3, R.sub.4 and R.sub.5 may be the same as or different from each other and each represents an alkyl group, a substituted alkyl group, an aryl group or a substituted aryl group,R.sub.6 and R.sub.7 may be the same as or different from each other and each represents a hydrogen atom, an alkyl group, a substituted alkyl group, an aryl group or a substituted aryl group,Ar.sub.1 represents a single bond or Ar.sub.2, andAr.sub.Type: GrantFiled: October 5, 1989Date of Patent: March 26, 1991Assignee: Fuji Photo Film Co., Ltd.Inventors: Toshiaki Aoai, Teruo Nagano
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Patent number: 4977293Abstract: Monoethylenically unsaturated compounds whose polymers are useful as polymeric photoinitiators are of formula Ar.sup.1 COC(R.sup.1)(R.sup.2)R.sup.3 where R.sup.1 is (C.sub.1 -C.sub.10 alkyl or alkoxy, R.sup.2 is C.sub.1 -C.sub.10 alkyl, --X--O--R.sup.4 -OCOC(R.sup.5).dbd.CH.sub.2 (II) --X--NH--R.sup.6 --OCOC(R.sup.5).dbd.CH.sub.2 (III), or --CH.sub.2 [OCH.sub.2 CH(OH)CH.sub.2 ].sub.a OCOC(R.sup.5).dbd.CH.sub.2 (IIIA) or R.sup.1 and R.sup.2, together with the attached carbon, denote C.sub.4 -C.sub.8 cycloalkyl, R.sup.3 is a C.sub.6 -C.sub.20 aromatic group, OH tert. amino,--OCOC(R.sup.5).dbd.CH.sub.2 (VI) or --OCH.sub.2 CH(OH)CH.sub.2 OCOC(R.sup.5).dbd.CH.sub.2 (VIA), R.sup.4 is C.sub.1 14 C.sub.4 alkylene, which may be substituted by --OH or by C.sub.2 -C.sub.20 acyloxy, R.sup.5 is H or C.sub.1 -C.sub.4 alkyl, R.sup.6 is C.sub.1 to C.sub.4 alkylene, X is a group of formula R.sup.7 CO-- or ##STR1## where R.sup.7 is C.sub.1 -C.sub.4 alkylene, R.sup.8 is C.sub.1 to C.sub.4 alkyl, and is 0 or 1, Ar.sup.1 is a C.Type: GrantFiled: January 16, 1990Date of Patent: December 11, 1990Assignee: Ciba-Geigy CorporationInventors: Kevin B. Hatton, Edward Irving, Josephine M. A. Walshe, Anne Mallaband
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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: 4948819Abstract: A compound of general formula ##STR1## in which X.sup.- represents one equivalent of an anion; R.sup.5 represents a hydrogen atom or a methyl group; each R.sup.4 independently represents a methyl or ethyl group; and each of R.sup.1, R.sup.2 and R.sup.3 independently represents a hydrogen or halogen atom, an alkyl, alkoxy or alkylthio group having from 1 to 4 carbon atoms, an arylthio group or a group of formula ##STR2## in which R.sup.4, R.sup.5 and X have the meanings given above, are useful as water soluble co-polymerizable photoinitiators.Type: GrantFiled: February 27, 1989Date of Patent: August 14, 1990Assignee: Ward Blenkinsop & Company LimitedInventors: Peter N. Green, William A. Green
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Patent number: 4917977Abstract: A photosensitive composition comprising:(a) a compound of the formula ##STR1## (b) an ethylenically unsaturated compound capable of free radical initiated addition polymerization;(c) a polymeric binder; and(d) a free radical generating system activatable by actinic radiation which comprises a hexaarylbiimidazole and a chain transfer agent.A single step process for forming a light-stable hologram using this photosensitive composition is also disclosed.Type: GrantFiled: December 23, 1988Date of Patent: April 17, 1990Assignee: E. I. Du Pont de Nemours and CompanyInventor: William K. Smothers
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Patent number: 4910232Abstract: The ultraviolet-curable organoploysiloxane composition of the invention comprises (A) an organopolysiloxane having bonded to a silicon atom thereof a silyl-substituted ethyl group represented by the general formula[CH.sub.2 .dbd.CR.sup.1 --CO--O--(--CH.sub.2 --).sub.a --SiR.sup.2.sub.2 --](R.sup.2 .sub.3 Si--O--).sub.c R.sup.2.sub.2--c Si--C.sub.2 H.sub.4 --,in which R.sup.1 is a hydrogen atom or a methyl group, R.sup.2 is a monovalent hydrocarbon group, a is 1, 2 or 3 and c is 1 or 2, and (B) a photopolymerization initiator. The composition is rapidly cured by ultraviolet irradiation into a gel-like material having adhesiveness without the disadvantages of catalyst poisoning and undue volume shrinkage so that the composition is useful as a potting agent in electronic and electric components.Type: GrantFiled: July 7, 1988Date of Patent: March 20, 1990Assignee: Shin-Etsu Chemical Co., Ltd.Inventor: Masatoshi Arai
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Patent number: 4824765Abstract: Substituted dibenzalketones useful as water-soluble photoinitiators have the formula: ##STR1## wherein R.sup.1 and R.sup.2 are 4, alkyl or, taken together, an aliphatic ring, n=0 or an integer and R.sup.3 and R.sup.4 either are both water-solubilizing groups (a) --X(CH.sub.2).sub.m N.sup.+ R.sup.5.sub.3, (b) --X(CH.sub.2).sub.m COO.sup.- M or (c) --X(CH.sub.2).sub.m SO.sup.-.sub.3 M.sub.5 or one is such a group and the other is (d) a group --NR.sup.5.sub.2, X is --CH.sub.2 --, --O-- or --S--, R.sup.5 is an alkyl group, M is H.sup.+ or a metal cation and m=0. Such a photoinitiator compound is associated with a polymerizable compound in an aqueous photopolymerizable composition.Type: GrantFiled: October 10, 1986Date of Patent: April 25, 1989Inventors: John A. Sperry, Ross A. Balfour
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Patent number: 4795766Abstract: Propiophenones of the formula I ##STR1## in which R.sup.1 is hydrogen or C.sub.1 -C.sub.4 -alkyl, --Si(CH.sub.3).sub.3, allyl or benzyl, R.sup.2 is hydrogen, C.sub.1 -C.sub.8 -alkyl, C.sub.1 -C.sub.4 -alkyl which is substituted by C.sub.1 -C.sub.4 -alkoxy or --OH, --(CH.sub.2 --CH.sub.2 --O).sub.n --R.sup.5 where n is 2 to 20 and R.sup.5 is H or C.sub.1 -C.sub.4 -alkyl, --Si(CH.sub.3).sub.3, benzyl, C.sub.3 -C.sub.6 -alkenyl, C.sub.3 -C.sub.4 -alkynyl or 2-tetrahydrofuranyl, or R.sup.1 and R.sup.2 together are a C.sub.1 -C.sub.6 -alkylidene radical or a C.sub.2 -C.sub.6 -alkylidene radical which is substituted by hydroxyl, C.sub.1 -C.sub.4 -alkoxy or phenyl, a linear or branched C.sub.2 -C.sub.6 -alkanediyl radical, a benzylidene, cyclopentylidene or cyclohexylidene radical or a 2,2,2-trichloroethylidene, 2-furylimethylidene or dimethylsilylidene radical, R.sup.3 is phenyl which is unsubstituted or substituted by one or more --Cl, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy or C.sub.1 -C.sub.Type: GrantFiled: June 30, 1986Date of Patent: January 3, 1989Assignee: Ciba-Geigy CorporationInventors: Werner Rutsch, Rudolf Kirchmayr, Rinaldo Husler, Kurt Dietliker
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Patent number: 4789505Abstract: A part made of a resin-containing composite material, also having at least one insert made of a different material, is hardened by electron beam radiation in zones having a surface mass at the most equal to 4 g/cm.sup.2 and by X-radiation in zones having a surface mass above 4 g/cm.sup.2. The X-radiation, in doses up to 10 Mrad, is produced by action of the electron beam on a target placed between the part and the electron beam.Type: GrantFiled: April 21, 1987Date of Patent: December 6, 1988Assignee: Societe Nationale Industrielle Aerospatiale etInventor: Daniel Beziers
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Patent number: 4767797Abstract: A linear polymer having a recurring unit represented by the formula (I): ##STR1## wherein R.sub.1, R.sub.2, R.sub.3 and R.sub.4 each independently is a hydrogen atom, a C.sub.1-10 alkyl group, a C.sub.6-10 cycloalkyl group, an aryl group, or a halogen atom and the ethynyl group is in either meta position or para position to the main polymer chain;and a weight-average molecular weight of 1,000 to 1,000,000. A resin composition consisting essentially of (i) a polymer having a recurring unit represented by the formula (I) or a polymer having a recurring unit represented by the formula (I) and a recurring unit represented by the formula (II): ##STR2## wherein X and Y each independently is a C.sub.6-20 aryl group, a C.sub.1-10 alkyl group, a C.sub.6-10 cycloalkyl group, a silyl group having a C.sub.1-10 alkyl group or a C.sub.Type: GrantFiled: August 25, 1986Date of Patent: August 30, 1988Assignee: Asahi Kasei Kogyo Kabushiki KaishaInventors: Hideo Ai, Yohsuke Koizumi, Naohiro Tsuruta
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Patent number: 4755450Abstract: Spectral sensitizing dyes which sensitize photoinitiators and disperse in aqueous solutions are desirable in photosensitive systems where precise color rendition is important.Type: GrantFiled: April 22, 1986Date of Patent: July 5, 1988Assignee: Minnesota Mining and Manufacturing CompanyInventors: James F. Sanders, David B. Olson
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Patent number: 4740532Abstract: A dielectric coating composition that is screen printable and radiation curable is disclosed. The composition is composed of from about 10 percent to about 50 percent of an unsaturated thiolene prepolymer system, from about 0 percent to about 35 percent of an acrylated prepolymer system, from about 10 percent to about 40 percent of at least one crosslinking diluent monomer, from about 4 percent to about 18 percent of at least one plasticizer and from about 3 percent to about 12 percent of at least one nonshrinking monomer. The cured coating is sufficiently compliant at normal temperatures to avoid cracking upon flexure of thermal expansion of the substrate.Type: GrantFiled: December 9, 1986Date of Patent: April 26, 1988Assignee: AMP IncorporatedInventors: Clifton C. May, Jr., Steven G. Wentink
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Patent number: 4702990Abstract: The present invention provides a photosensitive resin composition used to form a top resist layer of a multilayer resist system, the composition comprising a photosensitive polyphenylsilsesquioxane represented by the following general formula (I) of: ##STR1## wherein X is selected from the group consisting of acryloyloxymethyl, methacryloyloxymethyl, and cinnamoyloxymethyl; and l, m and n are zero or positive integers but l and m do not take the value of zero simultaneously; and a bisazide compound added to act as a cross-linking agent.The photosensitive resin composition has high sensitivity to UV light and excellent resistance to reactive ion etching under oxygen gas (O.sub.2 RIE).Type: GrantFiled: May 10, 1985Date of Patent: October 27, 1987Assignee: Nippon Telegraph and Telephone CorporationInventors: Akinobu Tanaka, Masao Morita, Saburo Imamura, Toshiaki Tamamura, Osamu Kogure
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Patent number: 4672079Abstract: A new class of polymeric or polymerizable aromatic-aliphatic ketones, the preferred of which are: 2-hydroxy-2-methyl(4-vinylpropiophenone), 2-hydroxy-2-methyl-p(1-methylvinyl)propiophenone, p-vinylbenzoylcyclohexanol, p-(1-methylvinyl)benzoyl-cyclohexanol and their oligomerization and polymerization products, they being suitable for use as photoinitiators for the photopolymerization of ethylenically unsaturated monomers and prepolymers.Said ketones are produced by subjecting an aromatic substrate, preferably a monomer or oligomer of styrene type, to the following reaction cycle: polymerization - acylation - alphachlorination - nucleophilic substitution with the formation of epoxyether - hydrolysis of the epoxyether; or to other reactions as modifications or alternatives to this cycle.The ketones according to the present invention have high efficiency as photoinitiators both with regard to the useful concentration to be used and with regard to the polymerization rate.Type: GrantFiled: April 5, 1985Date of Patent: June 9, 1987Assignees: Fratelli Lamberti S.p.A., Consiglio Nazionale Delle RicercheInventors: Giuseppe Li Bassi, Luciano Cadona, Carlo Nicora, Carlo Carlini
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Patent number: 4666953Abstract: Polyorganosiloxanes having an average of more than two siloxane repeat units, at least one of which repeat units includes a photoinitiating group bound to the silicon atom thereof, the photoinitiating group having the formula ##STR1## where R.sup.1 and R.sup.2 are the same or different alkyl groups or R.sup.1 and R.sup.2 are alkylene groups linked to each other so that R.sup.1 and R.sup.2 together with the carbon atom to which both are attached comprise a cycloalkyl group, and R.sup.3 is H or hydrocarbyl.Compositions of these polyorganosiloxanes and silicones or organic monomers with free radical curable groups are readily cured by irradiation with UV light.Type: GrantFiled: March 28, 1985Date of Patent: May 19, 1987Assignee: Loctite CorporationInventors: Philip Klemarczyk, Steven T. Nakos, Samuel Q. S. Lin
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Patent number: 4587276Abstract: Novel polymeric photocleavable photoinitiators are prepared by the hydrosilation reaction of an organosilicon hydride grafting agent which has a photoinitiating aromatic-aliphatic ketone derivative of at least one organo group, with a polymer having a plurality of unsaturated olefinic or acetylenic sites in the presence of a hydrosilation catalyst. Preferred polymers are butadiene or alkyl substituted butadiene polymers and copolymers and vinyl functional polyorganosiloxanes. The grafting agents have the formula (hv)--R.sup.8 --R.sup.5 --H wherein (hv) is a photoinitiating aromatic-aliphatic ketone group, R.sup.8 is selected from alkylene, alkenylene, alkylenoxy and oxy groups, and R.sup.5 is selected from ##STR1## the R.sup.6 groups are the same or different organo or halo groups and n is an integer.Type: GrantFiled: August 31, 1983Date of Patent: May 6, 1986Assignee: Loctite CorporationInventors: Qcheng S. Lien, Robert W. R. Humphreys
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Patent number: 4582862Abstract: Compounds of the formula I, II or III ##STR1## in which Ar is a sulfur-containing aromatic radical, R.sup.1 and R.sup.2 are a monovalent hydrocarbon radical which is substituted or unsubstituted or R.sup.1 and R.sup.2 together form alkylene, oxaalkylene or azaalkylene, R.sup.3 is a direct bond or a divalent hydrocarbon radical, X is a monovalent amino group and X' is a divalent amino or diamino group, are excellent photoinitiators for the photocuring of colored, in particular pigmented, compositions containing an olefinically unsaturated, photopolymerizable binder.Type: GrantFiled: February 22, 1983Date of Patent: April 15, 1986Assignee: Ciba-Geigy CorporationInventors: Godwin Berner, Rinaldo Husler, Rudolf Kirchmayr