Specified Rate-affecting Material Is Heterocyclic Patents (Class 522/16)
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Patent number: 5731363Abstract: A photopolymerizable composition comprising an addition-polymerizable compound having at least one ethylenic unsaturated double bond, at least one specific sensitizing dye such as the following formula (I), and a titanocene compound: ##STR1## The substituents in formula (I) are defined in the specification.Type: GrantFiled: February 28, 1996Date of Patent: March 24, 1998Assignee: Fuji Photo Film Co., Ltd.Inventors: Yasuo Okamoto, Syunichi Kondo
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Patent number: 5728747Abstract: A free radical polymerization process for the preparation of polymer comprising:a first heating and photoinitiating with ultraviolet light of a mixture comprised of a stable free radical agent, and at least one polymerizable monomer compound;optionally cooling said mixture;a second heating of said mixture at a temperature of from about 100.degree. C. to about 160.degree. C.;isolating the polymer product formed; andoptionally washing and drying said polymer.Type: GrantFiled: August 8, 1996Date of Patent: March 17, 1998Assignee: Xerox CorporationInventors: Peter M. Kazmaier, Barkev Keoshkerian, Rafik O. Loutfy, Karen A. Moffat, Michael K. Georges, Gordon K. Hamer, Richard P. N. Veregin
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Patent number: 5721288Abstract: A photopolymerizable composition is described, comprising components (i) a compound having at least one addition-polymerizable ethylenically unsaturated bond, (ii) a compound represented by the following formula (I): ##STR1## and (iii) an activating agent which generates an active radical upon light irradiation in the co-presence of component (ii). The substituents in formula (I) are defined in the specification.Type: GrantFiled: February 9, 1996Date of Patent: February 24, 1998Assignee: Fuji Photo Film Co., Ltd.Inventors: Yoshimasa Aotani, Tadahiro Sorori
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Patent number: 5700849Abstract: A photopolymerizable composition is disclosed, which comprises an addition-polymerizable compound having at least one ethylenically unsaturated double bond, a sensitizing dye represented by the following formula (I): ##STR1## wherein the all symbols are defined in the disclosure, and a titanocene compound.Type: GrantFiled: February 23, 1996Date of Patent: December 23, 1997Assignee: Fuji Photo Film Co., Ltd.Inventors: Syunichi Kondo, Kazuo Fujita
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Patent number: 5693390Abstract: A surface-coated vessel or a surface-coated product having a hard coating layer is obtained, by coating a substrate of, for example, resin product with a resin composition for hard coating which comprises(a) a poly?(meth)acryloyloxyalkyl!(iso)cyanurate represented by the following general formula (1) or (2): ##STR1## wherein X.sup.1, X.sup.2 and X.sup.3 are each an acryloyl group, methacryloyl group, hydrogen atom or an alkyl group, with a proviso that at least two of them are (meth)acryloyl groups, and R.sup.1, R.sup.2 and R.sup.3 are each an oxyalkylene group or a polyoxyalkylene group;(b) a poly(meth)acrylated polyoxyalkane polyol;(c) a photopolymerization initiator consisting of 2-methyl-1-?4-(methylthio)phenyl!-2-morpholino-1-propanone;(d) a photopolymerization initiator based on thioxanthone;(e) a UV-absorber based on monohydroxybenzophenone;(f) an organic solvent.Type: GrantFiled: September 20, 1996Date of Patent: December 2, 1997Assignee: Mitsui Petrochemical Industries, Ltd.Inventors: Hajime Inagaki, Koji Yoshii
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Patent number: 5691394Abstract: A photopolymerizable composition is disclosed, comprising an addition polymerizable compound having at least one ethylenically unsaturated double bond, a sensitizing dye represented by formula (I) and a titanocene compound. The photopolymerizable composition exhibits high sensitivity to active light rays over a wide region of from ultraviolet light to visible light.Type: GrantFiled: February 7, 1996Date of Patent: November 25, 1997Assignee: Fuji Photo Film Co., Ltd.Inventor: Syunichi Kondo
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Patent number: 5686220Abstract: A photo-curing composition including an image forming material, an ethylenically unsaturated monomer which is curable by polymerization thereof, a polymerization initiator which initiates the polymerization of the monomer, and two or more photosensitizers each of which absorbs a light and thereby causes the polymerization initiator to initiate the polymerization of the monomer, the photosensitizers having different maximum absorption wavelengths, respectively. A photosensitive capsule including a core material including the photo-curing composition, and a shell material within which the core material is encapsulated.Type: GrantFiled: January 30, 1996Date of Patent: November 11, 1997Assignee: Brother Kogyo Kabushiki KaishaInventor: Masashi Tsuda
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Patent number: 5681685Abstract: The present invention relates to a photopolymerizable composition comprising squarylium compound represented by the formula (I): ##STR1## wherein R represents lower alkyl having 2 to 8 carbon atoms, a radical generator and an addition-polymerizable compound having at least one ethylenic unsaturated double bond.Type: GrantFiled: May 21, 1996Date of Patent: October 28, 1997Assignee: Kyowa Hakko Kogyo Co., Ltd.Inventors: Tsuguo Yamaoka, Kenichi Koseki, Ikuo Shimizu, Hiroshi Toyoda, Hirotaka Kinoshita, Shoshiro Matsushita
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Patent number: 5679719Abstract: Resin compositions useful for filament winding applications comprising an epoxy component including at least one polyepoxide resin curable by heat, an olefinicially unsaturated monomer component including at least one polyolefinically unsaturated monomer curable by actinic radiation, at least one photoinitiator which is not a peroxide, at least one organic peroxide, and a heat activated curing agent for epoxides. The compositions have a viscosity less than about 2000 centipoise (cps) and are capable of retaining this viscosity for at least about 2 hours at a temperature of from about ambient temperature to about 60.degree. C. The resins are capable of being immobilized by actinic radiation exposure and further heat cured without substantial resin drip. One or more organic peroxides are employed, selected from the group of organic peroxides having 10 hour decomposition half lives at temperatures of from about 50.degree. C. to less than about 104.degree. C.Type: GrantFiled: June 7, 1995Date of Patent: October 21, 1997Assignee: Loctite CorporationInventors: Philip T. Klemarczyk, Yoshihisa Okamoto, James P. Moran, Jr., Susan Levandoski, Veronica Hanlon
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Patent number: 5667893Abstract: The present invention relates to an article comprising a substrate which has coated thereon a photopolymerizable epoxy composition containing a plurality of epoxides including at least one selected from the group consisting of bisphenol A epoxides and cycloaliphatic epoxides, and at least one aliphatic epoxide, from about 0.1% to about 2% of at least one organometallic cationic initiator capable of initiating polymerization at wavelengths of from about 200 to about 600 nm, and optionally at least one accelerating agent. The article can be a flexible tape backing or a chip-resistant paint.Type: GrantFiled: February 4, 1994Date of Patent: September 16, 1997Assignee: Minnesota Mining and Manufacturing CompanyInventors: Kevin E. Kinzer, Lowell W. Holland, Krishnamurthy Sridhar, James N. Kellen, Richard W. Pribnow
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Patent number: 5623000Abstract: A pressure-sensitive adhesive having excellent heat resistance, comprising a photopolymerization product of a composition comprising;a) 100 parts by weight of a monomer mixture comprising from 70 to 100% by weight of a (meth)acrylic acid alkyl ester having from 2 to 14 carbon atom on the average in the alkyl moiety and from 30 to 0% by weight of a monoethylenically unsaturated monomer copolymerizable with the (meth)acrylic acid alkyl ester,b) from 0.02 to 5 parts by weight of a polyfunctional (meth)acrylate as a crosslinking agent, andc) from 0.01 to 4 parts by weight of a photopolymerization initiator,wherein a content of the solvent-insoluble components is at least 60% by weight and a remaining amount of the unreacted monomers is less than 5,000 ppm.Type: GrantFiled: June 5, 1995Date of Patent: April 22, 1997Assignee: Nitto Denko CorporationInventors: Takao Yoshikawa, Takaaki Moriyama
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Patent number: 5621017Abstract: A photochromic composition which can be polymerized and cured upon irradiation with active energy rays such as ultraviolet rays to exhibit favorable photochromic property. The photochromic composition comprises 100 parts by weight of a radical polymerizable monomer, 0.001 to 0.2 parts by weight of a photochromic compound, and 0.01 to 1 part by weight of a photo polymerization 1.0 initiator. A photochromic cured product is obtained by irradiating the photochromic composition with the light which contains ultraviolet rays.Type: GrantFiled: April 25, 1995Date of Patent: April 15, 1997Assignee: Tokuyama CorporationInventors: Takashi Kobayakawa, Junji Momoda
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Patent number: 5618856Abstract: There are disclosed herein a visible light sensitizer for a photopolymerizing initiator and/or a photocrosslinking agent which comprises a thiobarbituric acid derivative compound of the general formula (A) or (B): ##STR1## a photopolymerizable and/or a photocrosslinkable composition in which the thiobarbituric acid derivative compound is used, and a hologram recording medium in which the composition is used.Type: GrantFiled: June 16, 1995Date of Patent: April 8, 1997Assignee: Canon Kabushiki KaishaInventors: Yoko Yoshinaga, Naosato Taniguchi, Shin Kobayashi
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Patent number: 5609992Abstract: A photopolymerizable composition is disclosed, comprising (i) a compound having at least one addition-polymerizable, ethylenically unsaturated bond; (ii) a compound represented by formula (IA) or (IB): ##STR1## wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.9, R.sup.10, R.sup.11 and R.sup.12 each independently represents a hydrogen atom, a halogen atom, an alkyl group, a substituted alkyl group, an aryl group, a substituted aryl group, a hydroxyl group, a substituted oxy group, a mercapto group, a substituted thio group, an amino group, a substituted amino group, a substituted carbonyl group, a sulfo group, a sulfonato group, a substituted sulfinyl group, a substituted sulfonyl group, a phosphono group, a substituted phosphono group, a phosphonato group, a substituted phosphonato group, a cyano group or a nitro group or R.sup.1 and R.sup.2, R.sup.2 and R.sup.3, R.sup.3 and R.sup.4, R.sup.9 and R.sup.10, R.sup.10 and R.sup.11 or R.sup.11 and R.sup.Type: GrantFiled: October 27, 1995Date of Patent: March 11, 1997Assignee: Fuji Photo Film Co., Ltd.Inventors: Tadahiro Sorori, Yasuo Okamoto, Syunichi Kondo, Hiromichi Kurita
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Patent number: 5593812Abstract: The sensitivity of a photoresist to actinic light is improved by the addition of certain dyes. The photoresist includes a polymer matrix, a photosensitive acid generator and at least one compound selected from the group consisting of dyes containing at least one heterosulphur atom such as 2,2.sup.1,5.sup.1,2"-terthiophene and its derivatives; thianthrene and its derivatives, and 4,6-diphenylthieno(3,4-d)-1,3-dioxol-2-one-5,5-dioxide; phenylsulfone and its derivatives; and 4,5-diphenyl-1,3-dioxol-2-one; 3,4-bis(acetoxymethyl)furan; chelidonic acid and its derivatives; and 5,7,12,14-pentacenetetrone. Resist images on a substrate are formed from the compositions.Type: GrantFiled: February 17, 1995Date of Patent: January 14, 1997Assignee: International Business Machines CorporationInventors: Edward D. Babich, Karen E. Petrillo, John P. Simons, David E. Seeger
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Patent number: 5561029Abstract: The present invention sets forth the incorporation of a substituted 2-phenyl-4,6-bis (trichloromethyl)-1,3,5-triazine in photoresists of lithographic printing plates for the purpose of promoting their shelf-life, room light stability, and developability. The present invention provides a photocurable composition comprising at least a photopolymerizable ethylenically unsaturated monomer having at least one terminal ethylenic group and capable of forming a polymer upon exposure to actinic radiation; and an s-triazine capable of initiating free radical polymerization of the photopolymerizable ethylenically unsaturated monomer and being represented by the following general formula [I]: ##STR1## wherein R.sub.1 is either OR.sub.4 or NR.sub.5 R.sub.6, wherein R.sub.5 and R.sub.6 may or may not be identical with each other, either R.sub.5 or R.sub.6 may represent hydrogen, and wherein R.sub.4 and at least one of R.sub.5 and R.sub.Type: GrantFiled: April 28, 1995Date of Patent: October 1, 1996Assignee: Polaroid CorporationInventors: Maurice J. Fitzgerald, Frederick R. Kearney, Rong-Chang Liang, William C. Schwarzel, Donna J. Guarrera, John M. Hardin, John C. Warner
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Patent number: 5451616Abstract: A liquid composition which on exposure to actinic radiation polymerizes to form a heat-curable solid film adhesive, said composition comprising (A) a heat-curable phenol-aldehyde resol resin, (B) a photopolymerizable polyurethane or polyester having, on average, more than one polymerizable acrylic group per molecule, or a mixture of said polyurethane and said polyester, (C) a photopolymerization initiator for (B) and (D) a polyvinylacetal.Type: GrantFiled: August 2, 1994Date of Patent: September 19, 1995Assignee: Ciba-Geigy CorporationInventors: Margaret R. Haddon, Terence J. Smith, Stuart Mansfield
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Patent number: 5439746Abstract: Disclosed is an epoxy resin-based composite material formed by coating or impregnating a sheet-like reinforcement with an epoxy resin composition, followed by curing the resin composition. The epoxy resin composition comprises a compound having at least one epoxy group, a compound having an active hydrogen, a silicon compound having or generating hydroxy group bonded to silicon atom, and an organometallic compound. The epoxy resin may further comprise a maleimide compound or a powdery and granular material and a short fiber. The composite material ensures the properties of the epoxy resin material in terms of the mechanical strength, corrosion resistance, heat resistance and electrical properties. Besides, the composite material exhibits excellent crack resistance and impact resistance. Further, the epoxy resin composition contained in the composite material exhibits sufficient curing characteristics and, thus, the operation for forming the composite material is facilitated.Type: GrantFiled: March 18, 1994Date of Patent: August 8, 1995Assignee: Kabushiki Kaisha ToshibaInventor: Shuichi Suzuki
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Patent number: 5426131Abstract: An ultraviolet radiation curable silica coating composition containing (a) acrylic monomers, (b) functionalized colloidal silica, (c) acrylated urethanes, (d) an ultraviolet radiation absorber, and (e) a photoinitiator. The coating composition once applied to and cured on a thermoplastic substrate provides a coating which exhibits improved flexibility and weathering. The coatings are useful for providing abrasion resistance and weatherability to thermoplastic, for example polycarbonate, substrates.Type: GrantFiled: October 13, 1993Date of Patent: June 20, 1995Assignee: General Electric CompanyInventor: Dimitris Katsamberis
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Patent number: 5403698Abstract: A negative type photosensitive electrodepositing resin composition comprising (a) a polymer obtained by neutralizing a copolymer of acrylic or methacrylic acid and having an acid number of 20 to 300 with a basic organic compound, (b) a non-water-soluble monomer having two or more photopolymerizable unsaturated bonds in the molecule, (c) a non-water-soluble photoinitiator, and (d) a benzotriazole derivative having one or more carboxyl groups, is effective for giving electrodeposited films with a low voltage or low electric current in a short time, and usable for forming resist patterns with high degree of resolution.Type: GrantFiled: October 11, 1991Date of Patent: April 4, 1995Assignees: Hitachi Chemical Company, Ltd., Dai Nippon Toryo Co., Ltd.Inventors: Sigeo Tachiki, Masahiko Hiro, Toshihiko Akahori, Takuro Kato, Hajime Kakumaru, Yoshitaka Minami, Yuhji Yamazaki, Toshiya Takahashi, Toshihiko Shiotani, Yoshihisa Nagashima
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Patent number: 5358976Abstract: Curable norbornene-thiol compositions are stabilized by addition of a non-acidic Nitroso compound.Type: GrantFiled: December 23, 1992Date of Patent: October 25, 1994Assignee: Loctite (Ireland) LimitedInventors: Joseph P. Dowling, Sarah C. Richardson, Killian Quigley
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Patent number: 5331018Abstract: The present invention is directed to a non-emissive, bimodal cured polymeric network which has an onset degradation temperature that is about 100.degree. C. above the onset degradation temperature of a base polymer. The novel cured polymeric network comprises the cured reaction product of the following ingredients: (a) combination of one or more liquid carrier monomers or prepolymers which combination is reactive to form a base polymer by exposure to ultraviolet (UV) radiation in the presence of a UV photosensitizer at a temperature, T.sub.uv ; and (b) between about 10 and 100 wt-% based on ingredient (a) of a combination of one or more monomers or prepolymers which combination is reactive to form a cured high temperature stable polymer by heating at a temperature, T.sub..DELTA.. Ingredient (b) is soluble or dispersible in ingredient (a) at a temperature, T.sub.s, wherein T.sub.s is equal to or lower than T.sub.uv, and T.sub.uv is at least about 50.degree. C. lower than T.sub..DELTA..Type: GrantFiled: August 26, 1992Date of Patent: July 19, 1994Assignee: Three Bond Co., Ltd.Inventors: Vincent D. McGinniss, James L. White, Hiroyuki Mikuni
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Patent number: 5322762Abstract: A highly stable photopolymerizable composition which is highly photosensitive to visible light, which can be hardened using a visible light laser, such as an argon laser, which provides excellent contrast between non-irradiated portions and the substrate under red light, and, moreover, which provides excellent contrast between the portions irradiated by the laser and the portions not irradiated. The photopolymerizable composition consists of 100 parts by weight of a resin which is hardenable under visible light having an irradiation energy mainly consisting of light rays in the 400 nm to 700 nm visible light region; 0.02 to 0.5 parts by weight of at least one dye selected from the group consisting of Victoria Pure Blue, anthraquinone dyes, monoazo dyes, and merocyanine dyes, these dyes having maximum absorption wavelengths from 550 to 700 nm; 0.1 to 5 parts by weight of the leuco dye 4,4'-(phenylmethylene bis[N,N-diethylbenzene amine]; and 0.1 to 5 parts by weight of tribromomethylphenyl sulphone.Type: GrantFiled: April 13, 1993Date of Patent: June 21, 1994Assignee: Mitsubishi Rayon Co., Ltd.Inventors: Kenji Kushi, Chiho Tokuhara
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Patent number: 5321053Abstract: A dental composition comprising a vinyl monomer containing at least one acidic group in the molecule thereof and an initiator capable of photopolymerizing said monomer by visible light, characterized in that said initiator consisting essentially of:(a) a photosensitizer selected from an .alpha.-diketone, a quinone and a derivative thereof, and,(b) an accelerator selected from a compound containing at least one mercapto group in the molecule thereof is provided by the present invention.Type: GrantFiled: February 6, 1990Date of Patent: June 14, 1994Assignee: Kuraray Co., Ltd.Inventors: Kenichi Hino, Junichi Yamauchi, Koji Nishida
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Patent number: 5304628Abstract: A radiation-curing resin composition comprising (A) a resin having a carboxylic acid group and an unsaturated double bond and (B) a compound containing a cyclocarbonate group. The composition is excellent in stability and curing properties and provides a cured film excellent in water resistance, solvent resistance, chemical resistance, and heat resistance.Type: GrantFiled: August 4, 1992Date of Patent: April 19, 1994Assignee: Dainippon Ink and Chemicals, Inc.Inventors: Masashi Kinoshita, Hidenobu Ishikawa
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Patent number: 5302627Abstract: Adding a dye with a visible color to an ultraviolet radiation curable composition which contains a photoinitiator which generates free radicals upon exposure to ultraviolet radiation produces a composition which changes visible color upon exposure to ultraviolet radiation. This visible color change indicates that the composition has cured. This cure indication is useful for compositions curable by ultraviolet radiation in the electronics and electrical industry.Type: GrantFiled: March 9, 1992Date of Patent: April 12, 1994Assignee: Dow Corning CorporationInventors: Arthur J. Field, Michael R. Strong
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Patent number: 5268255Abstract: A printed circuit board has a resist layer made from a photo-setting resist composition containing:(A) a polyfunctional unsaturated compound which is solid at room temperature,(B) a polyfunctional unsaturated compound which is liquid at room temperature,(C) a photopolymerization initiator,(D) an epoxy resin,(E) at least one member selected from the group consisting of:(i) a curing agent for the epoxy resin and either melamine or the derivative thereof, and(ii) a compound having a 2,4-diamino-s-triazine ring and an imidazole ring in the molecule.Type: GrantFiled: September 30, 1991Date of Patent: December 7, 1993Assignee: Hitachi, Ltd.Inventors: Hiroshi Kikuchi, Makio Watanabe, Shinichiro Imabayashi, Reiko Yano, Isamu Tanaka, Hitoshi Oka, Yukihiro Taniguchi, Shigeru Fujita
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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: 5230986Abstract: A Photohardenable composition consisting essentially of a free radical polymerizable compound, an electron donating coinitiator, and a benzospiropyran, wherein the benzospiropyran undergoes ring opening to form a merocyanine upon exposure to a actinic radiation or heat and exposure to a second 296 radiation causes the composition to harden.Type: GrantFiled: February 1, 1991Date of Patent: July 27, 1993Assignee: StereoGraphics Limited PartnershipInventor: Douglas C. Neckers
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Patent number: 5218009Abstract: Compounds of the formula I ##STR1## in which at least one of the radicals R.sub.1, R.sub.2 and R.sub.3 is a substituted alkyl radical or cycloalkyl radical, or R.sub.1 and R.sub.2 together with the phosphorus atom form a monocyclic or tricyclic ring, are effective photoinitiators for the photopolymerization of ethylenically unsaturated compounds.Type: GrantFiled: August 28, 1991Date of Patent: June 8, 1993Assignee: Ciba-Geigy CorporationInventors: Werner Rutsch, Kurt Dietliker, Roger G. Hall
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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: 5212271Abstract: A process for texturing a coating via exposing a photocurable composition comprising a multifunctional urea compound, an ethylenically unsaturated compound, and an aromatic ketone photosensitizer that functions through a hydrogen abstraction mechanism when exposed to ultraviolet light.Type: GrantFiled: December 22, 1989Date of Patent: May 18, 1993Assignee: Texaco Chemical CompanyInventors: Alison D. Beckett, Joseph V. Koleske, Richard M. Gerkin
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Patent number: 5207577Abstract: A dental adhesive comprising a (meth)acryloylaminoalkyl carboxylate of the formula ##STR1## in which R.sup.1 represents hydrogen or methyl;R.sup.2 represents methylene or ethylene; andR.sup.3 represents hydrogen, methyl, or ethyl;and at least one of an initiator, a non-toxic solvent, and a filler. The dental adhesive is useful to effect a strong adhesive bonding of dental materials to collagen-containing materials.Type: GrantFiled: January 25, 1991Date of Patent: May 4, 1993Assignee: Bayer AktiengesellschaftInventors: Michael Muller, Wolfgang Podszun
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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: 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: 5147938Abstract: Pressure-sensitive acrylate-based adhesive copolymers comprising polymerized acrylate units and polymerized fluorochemical surfactant units and a process for preparing same. Also prepolymeric compositions comprising the monomeric components of an acrylate-based pressure-sensitive adhesive and a polymerizable fluorochemical surfactant. The prepolymeric compositions generally have surface energy lower than that of the monomeric components of the acrylate-based pressure sensitive adhesive alone. Also, the adhesive compositions better maintain adhesive properties when aged when compared to corresponding adhesive compositions involving non-polymerizable fluorochemical surfactants.Type: GrantFiled: April 2, 1991Date of Patent: September 15, 1992Assignee: Minnesota Mining and Manufacturing CompanyInventor: Douglas H. Kuller
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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: 5137800Abstract: A polymerizable composition and a method are disclosed. The composition includes a photopolymerizable monomer and a photoinitiator system for the monomer. The system, in one embodiment, is one wherein a ray of activating radiation which enters a body of the composition through a surface thereof activates the photoinitiator system and causes polymerization at each of a succession of points, the first such point being immediately adjacent the surface and subsequent points being successively farther from the surface in the direction of travel of the ray of activating radiation, the distance from the surface to the point of the succession farthest therefrom varying as a function of at least one of(a) the intensity of the activating radiation and(b) the time during which the activating radiation enters the body through the surface.Type: GrantFiled: June 14, 1990Date of Patent: August 11, 1992Assignee: StereoGraphics Limited PartnershipInventors: Douglas C. Neckers, Oscar Valdes-Aguilera, Krishan S. Raghuveer, Darrell G. Watson
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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: 5114831Abstract: These photopolymerizable laminating materials consist of at least one film-forming polymer as a binder, at least one organic compound which is compatible with the binder, has at least two double bonds capable of addition polymerization and may be partially replaced by an organic compound having only one double bond capable of addition polymerization, a photoinitiator or photoinitiator system and an adhesion promoter, with or without conventional additives and assistants, the adhesion promoter used being a tricyclic heteroaromatic compound which is soluble in aqueous alkaline solutions.The said laminating materials are suitable for the production of printed circuits.Type: GrantFiled: August 2, 1990Date of Patent: May 19, 1992Assignee: BASF AktiengesellschaftInventors: Friedrich Seitz, Gerhard Hoffmann, Gerhard Bauer
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Patent number: 5112721Abstract: Combinations of selected photosensitizers produce unexpected increases in the both the photospeed of, and the resolution obtainable from, photopolymerizable compositions. The combinations contain one photosensitizer, known as the sensitizer, and a second photosensitizer, known as the co-sensitizer. The co-sensitizer has an absorbance maximum at a longer wavelength than the sensitizer and is generally present a much lower concentration than the sensitizer.Type: GrantFiled: July 19, 1991Date of Patent: May 12, 1992Assignee: E. I. Du Pont de Nemours and CompanyInventor: August D. Kuchta
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Patent number: 5112723Abstract: In a photosensitive recording element which contains at least one photopolymerizable recording layer (B) consisting ofb.sub.1) at least one partially of virtually completely hydrolyzed poly(vinyl alkanecarboxylate) and/or at least one partially or virtually completely hydrolyzed vinyl alkanecarboxylate/alkylene oxide graft copolymer as a binder,b.sub.2) at least one photopolymerization initiator,b.sub.3) at least one photopolymerizable olefinically unsaturated compound (monomer) which is compatible with the binder (b.sub.1), and/or photopolymerizable olefinically unsaturated radicals which are bonded as side radicals and/or terminal radicals to the binder (b.sub.1), andb.sub.4) at least two assistants, at least one of the said assistants (b.sub.4) has been selected from the group consisting ofb.sub.41) the isoalloxazines and the alloxazines, and at least one of the other assistants has been selected from the group consisting ofb.sub.Type: GrantFiled: February 8, 1990Date of Patent: May 12, 1992Assignee: BASF AktiengesellschaftInventors: Wolfgang Huemmer, Walter Dobler, Dieter Littmann
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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: 5096935Abstract: The invention relates 6-acyl-(6H)-dibenz[c,e][1,2]oxaphosphorine-6-oxides of the formula ##STR1## wherein each of R.sup.1, R.sup.2 and R.sup.3 may be present one or more times and R.sup.1, R.sup.2 and R.sup.3 represent halogen having an atomic number of from 9 to 35, alkyl or alkoxy each having from 1 to 6 carbon atoms and wherein Ar represents an aromatic hydrocarbon group having from 6 to 10 carbon atoms.The invention further relates to a process for the preparation of the afore-mentioned compounds and polymerizable compositions containing them as an essential ingredient as a photo-initiator. Finally the invention relates to 6-alkoxy-(6H)-dibenz[c,e][1,2]oxaphosphorin of the formula II ##STR2## wherein each of R.sup.1 and R.sup.2 may be present once or more times and R.sup.1 and R.sup.2 represent halogen having an atomic number of from 9 to 35, alkyl or alkoxy each having from 1 to 6 carbom atoms, at least one R.sup.1 being, however, halogen, and wherein R.sup.Type: GrantFiled: October 16, 1990Date of Patent: March 17, 1992Assignee: Hoechst AGInventors: Hans-Jerg Kleiner, Joachim Gersdorf, Udo Bastian
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Patent number: 5089536Abstract: An energy polymerizable composition and process therefore, comprising a cationically polymerizable material and a catalytically effective amount of an ionic salt of an organometallic complex cation as polymerization initiator, said ionic salt of an organometallic complex cation being capable of adding an intermediate strength nucleophile or upon photolysis capable of liberating at least one coordination site, said metal in said organometallic complex cation being selected from elements of Periodic Groups IVB, VB, VIB, VIIB, and VIIIB are disclosed. Certain of the organometallic metallic polymerization initiators are novel cationic salts.Type: GrantFiled: November 22, 1982Date of Patent: February 18, 1992Assignee: Minnesota Mining and Manufacturing CompanyInventor: Michael C. Palazzotto
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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: 5057398Abstract: A photopolymerizable composition that contains a polymeric binder, a polymerizable compound and photoinitiator combination comprising an N-heterocyclic compound and a halogen compound corresponding to one of the folowing formulas I and II ##STR1## in which X.sup.1 stands for chlorine or bromine,X.sup.2 and X.sup.3 are identical or different and denote X.sup.1, hydrogen or alkyl groups,Y and Z are identical or different and denote X.sup.1, hydrogen, CN or (A).sub.n --(B).sub.n --D,A is a phenylene group,n is 0 or 1,B is CO or SO.sub.2,D is R, OR, NHR, NH.sub.2, NR.sub.2 or CX.sup.1 X.sup.2 X.sup.3,R is an alkyl, cycloalkyl, aryl or heteroyl radical,W is a five or six-membered heterocyclic ring having from 1 to 3 heteroatoms, which optionally carries substituents and optionally a fused aromatic ring, andm is 1 or 2,is distinguished by an improved light sensitivity.Type: GrantFiled: April 26, 1990Date of Patent: October 15, 1991Assignee: Hoechst AktiengesellschaftInventors: Hans-Dieter Frommeld, Hansjoerg Vollmann
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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: 5034429Abstract: A photopolymerizable composition comprising (a) an addition polymerizable compound having a boiling point of 100.degree. C. or high under an atmospheric pressure, (b) a photoinitiator, and (c) a benzene derivative can provide a cured film having high strength suitable for producing, e.g. printed circuit boards.Type: GrantFiled: June 2, 1988Date of Patent: July 23, 1991Assignee: Hitachi Chemical Co., Ltd.Inventors: Makoto Kaji, Nobuyuki Hayashi, Futami Kaneko
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Patent number: RE35135Abstract: Disclosed is a photocurable composition comprising (a) a radical-polymerizable monomer, (b) an .alpha.-ketocarbonyl compound and (c) a derivative of mercaptobenzimidazole, mercaptobenzothiazole or mercaptobenzoxazole or an aromatic amine nucleus-substituted with an electron-attractive group. This composition has a high photocuring speed at a temperature close to normal temperature and gives a cured product excellent in various physical properties. This composition is valuable as a dental adhesive or resin.Type: GrantFiled: March 15, 1994Date of Patent: December 26, 1995Assignee: Mitsui Petrochemical Industries, Ltd.Inventors: Takeshi Sakashita, Takayuki Nakano