Monomer Or Polymer Contains Initiating Group Patents (Class 522/904)
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Patent number: 5629355Abstract: The invention is a polymeric photoinitiator having the formula: ##STR1## wherein n=10 to 50; each of a and b may be 0-4 while c is 0-5; A is an alkyl or aryl group; X is an anion; and each of R, R', and R" is independently H or one or more groups substituted onto the respective phenyl moieties. The substituted groups are independently selected from various kinds of groups excluding basic groups such as amino groups. Preferably, they are a hydrogen atom, halogen atom (e.g., F, Cl, Br, and I) , nitro group, alkoxy group (e.g. , CH.sub.3 O-- and C.sub.2 H.sub.5 O--) , C.sup.1 -C.sub.18 aliphatic group (e.g., hydrocarbon group such as CH.sub.3 --, C.sub.2 H.sub.5 --, and (CH.sub.3).sub.2 CH--; cyclic hydrocarbon group such as cyclohexyl group; and those which contain a heteroatom in the main chain or substituent group. The substituted groups may also be a C.sub.1 -C.sub.18 aliphatic group having at least one hydroxyl group or a C.sub.3 -C.sub.19 aliphatic group having a group of --OCH.sub.2 CH.sub.2 O--.Type: GrantFiled: May 29, 1996Date of Patent: May 13, 1997Assignee: International Business Machines CorporationInventor: Joseph P. Kuczynski
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Patent number: 5621018Abstract: Compounds of formula I: ##STR1## are disclosed. The compounds are photoinitiators which can be functionalized by means of ethylenic groups or can be bonded to H-active substances, in order, for example, to modify surfaces by means of photopolymerizable substances. The compounds are especially useful in the manufacture of contact lenses.Type: GrantFiled: June 6, 1995Date of Patent: April 15, 1997Assignee: CIBA GEIGY CorporationInventors: Peter Chabrecek, Dieter Lohmann
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Patent number: 5612391Abstract: Contact lenses formed from compounds of formula I: ##STR1## are disclosed. The compounds are photoinitiators which can be functionalized by means of ethylenic groups or can be bonded to H-active substances, in order, for example, to modify surfaces by means of photopolymerizable substances. The compounds are especially useful in the manufacture of contact lenses.Type: GrantFiled: June 6, 1995Date of Patent: March 18, 1997Assignee: Ciba Geigy CorporationInventors: Peter Chabrecek, Dieter Lohmann
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Patent number: 5612389Abstract: Compounds of formula I: ##STR1## are disclosed. The compounds are photoinitiators which can be functionalized by means of ethylenic groups or can be bonded to H-active substances, in order, for example, to modify surfaces by means of photopolymerizable substances. The compounds are especially useful in the manufacture of contact lenses.Type: GrantFiled: June 6, 1995Date of Patent: March 18, 1997Assignee: Ciba Geigy CorporationInventors: Peter Chabrecek, Dieter Lohmann
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Patent number: 5585416Abstract: A lithographic coating and method of framing a lithographic image are disclosed. The method comprises coating at least a portion of a surface of an article with a radiation-crosslinkable polymer, and exposing the coated surface to a pattern of radiation to crosslink the polymer in a lithographic image. The functionalized polymer is a copolymer of an isoolefin of 4 to 7 carbon atoms and para-alkylstyrene, wherein the para-alkylstyrene is functionalized with a radiation reactive group at the para-alkyl group of the para-alkylstyrene.Type: GrantFiled: June 7, 1995Date of Patent: December 17, 1996Assignee: Exxon Chemical Patents Inc.Inventors: Jay D. Audett, Kenneth O. McElrath
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Patent number: 5578419Abstract: Dyes suitable for use in the fabrication of color filters are described which contain one or more photopolymerizable substituents preferably represented by the following formula:D-(A-Yn.sup.1)n.sup.2 (1)where D represents a chromphoric nucleus, A denotes a connecting group, Y means the photopolymerizable group, n.sup.1 is 1-10,000, and n.sup.2 stands for an integer of 1-10. Also described are photosensitive resist resin compositions containing the dyes as well as color filters fabricated by curing the photosensitive resist resin compositions.Type: GrantFiled: April 6, 1994Date of Patent: November 26, 1996Assignee: Mitsui Toatsu Chemicals, IncorporatedInventors: Hisato Itoh, Akio Karasawa, Kenichi Sugimoto
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Patent number: 5559162Abstract: The present invention relates to polymeric peroxycarbonates, a process for making the polymeric peroxycarbonates and initiator compositions comprising these polymeric peroxycarbonates. The polymeric peroxycarbonates of the present invention provide significant advantages in the polymerization of vinyl monomers.Type: GrantFiled: February 23, 1995Date of Patent: September 24, 1996Assignee: Akzo Nobel, NVInventors: John Meijer, Petrus J. T. Alferink
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Patent number: 5554485Abstract: An antireflective coating composition for use with chemically amplified photoresist compositions comprising a polymer composition which is highly absorbent to mid and deep UV radiation, which is substantially inert to contact reactions with a chemically amplified photoresist composition, and which is insoluble in the developer for the chemically amplified photoresist composition.Type: GrantFiled: September 29, 1994Date of Patent: September 10, 1996Assignee: International Business Machines CorporationInventors: Robert R. Dichiara, James T. Fahey, Pamela E. Jones, Christopher F. Lyons, Wayne M. Moreau, Ratnam Sooriyakumaran, Gary T. Spinillo, Kevin M. Welsh, Robert L. Wood
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Patent number: 5552452Abstract: The present invention relates generally to the field of biological and medical adhesives and encompasses more specifically the closing of microsurgical wounds and other tissue wounds and defects due to surgical procedures or other causes. A medical adhesive comprising a photosensitizing species and an protein or peptide containing moiety are disclosed which may be applied to various tissues, an adhesive bond being formed by exposure of the adhesive to photoactivating radiation.Type: GrantFiled: March 15, 1993Date of Patent: September 3, 1996Assignee: Arch Development Corp.Inventors: John Khadem, Toan V. Truong
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Patent number: 5550171Abstract: The invention is a polymeric photoinitiator having the formula: ##STR1## wherein n=10 to 50; each of a and b may be 0-4 while c is 0-5; A is an alkyl or aryl group; X is an anion; and each of R, R', and R" is independently H or one or more groups substituted onto the respective phenyl moieties. The substituted groups are independently selected from various kinds of groups excluding basic groups such as amino groups. Preferably, they are a hydrogen atom, halogen atom (e.g., F, Cl, Br, and I), nitro group, alkoxy group (e.g., CH.sub.3 O-- and C.sub.2 H.sub.5 O--), C.sup.1 -C.sub.18 aliphatic group (e.g., hydrocarbon group such as CH.sub.3 --, C.sub.2 H.sub.5 --, and (CH.sub.3).sub.2 CH--; cyclic hydrocarbon group such as cyclohexyl group; and those which contain a heteroatom in the main chain or substituent group. The substituted groups may also be a C.sub.1 -C.sub.18 aliphatic group having at least one hydroxyl group or a C.sub.3 -C.sub.19 aliphatic group having a group of --OCH.sub.2 CH.sub.2 O--.Type: GrantFiled: May 31, 1995Date of Patent: August 27, 1996Assignee: International Business Machines CorporationInventor: Joseph P. Kuczynski
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Patent number: 5536759Abstract: This invention is a hot melt pressure sensitive adhesive formed by copolymerizing acrylic, or a combination of acrylic and vinyl, monomers, at least one of which is a photoinitiator, with the functional monomer, 1-(1-isocyanato-1-methyl ethyl)-3-(1-methyl ethenyl)benzene (m-TMI), to give a saturated polymer with pendant vinyl groups that are crosslinked by UV radiation.Type: GrantFiled: October 13, 1994Date of Patent: July 16, 1996Assignee: National Starch and Chemical Investment Holding CorporationInventors: Roopram Ramharack, Rama Chandran
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Patent number: 5527925Abstract: Compounds of formula I: ##STR1## are disclosed. The compounds are photoinitiators which can be functionalized by means of ethylenic groups or can be bonded to H-active substances, in order, for example, to modify surfaces by means of photopolymerizable substances. The compounds are especially useful in the manufacture of contact lenses.Type: GrantFiled: June 24, 1994Date of Patent: June 18, 1996Assignee: Ciba-Geigy CorporationInventors: Peter Chabrecek, Dieter Lohmann
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Patent number: 5525422Abstract: Radiation-crosslinkable self-adhesive tape (dicing tape) for the temporary fixing of wafers, having a support comprising a radiation-transparent film and a radiation-crosslinkable self-adhesive composition, characterized in that the polymeric self-adhesive composition contains copolymerized radiation initiators.Type: GrantFiled: October 27, 1994Date of Patent: June 11, 1996Assignee: Beiersdorf AktiengesellschaftInventors: Manfred Spies, Christian Harder, Gunter Guse, Claudia Feldt, Robert Meyer
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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: 5504830Abstract: An optical glass fiber coated with a protective layer of photocurable polyimide coating which can be prepared from the polymeric condensation product of 6FDA, DMDE, and a photosensitizing moiety. More particularly, the present invention relates to a photocurable polyimide coated glass fiber useful for optic applications.Type: GrantFiled: April 11, 1995Date of Patent: April 2, 1996Assignee: Amoco CorporationInventors: David D. Ngo, Paul J. Cahill, John J. Greczek
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Patent number: 5484822Abstract: In a process for cladding an optical fiber, a photoinitiator monomer having both a photoinitiating group and an ethylenically unsaturated group is reacted with a fluorosubstituted monomer having an ethylenically unsaturated group, thereby preparing a copolymer having pendant photoinitiating groups. This copolymer is then mixed with a fluorosubstituted diacrylate, thereby forming a photopolymerizable composition, which is coated on to the optical fiber and exposed to ultraviolet light, thereby curing the photopolymerizable composition to produce a cladding on the optical fiber. Preferred claddings can have refractive indices below 1.35.Type: GrantFiled: June 24, 1991Date of Patent: January 16, 1996Assignee: Polaroid CorporationInventor: Richard A. Minns
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Patent number: 5482817Abstract: An antireflective coating composition (ARC) for use with chemically amplified photoresist compositions comprising a polymer composition which is highly absorbent to mid and deep UV radiation, which is substantially inert to contact reactions with a chemically amplified photoresist composition, and which is insoluble in the developer for the chemically amplified photoresist composition.Type: GrantFiled: September 29, 1994Date of Patent: January 9, 1996Assignee: International Business Machines CorporationInventors: Robert R. Dichiara, Christopher F. Lyons, Ratnasabapathy Sooriyakumaran, Gary T. Spinillo, Kevin M. Welsh, Robert L. Wood
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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: 5468785Abstract: The invention relates to the use of cobaloximes and related cobalt(II) complexes which have essentially planar equatorially coordinated ligands and a pair of axially coordinated ligands which have at least one carbon-cobalt bond, as photoinitiators for free radical polymerizations. By selection of the appropriate cobaloximes and related complexes, it is possible to prepare polymers which have useful terminal functionality at both the head and the tail ends of the growing polymer chain. The process also teaches the photochemical polymerization and copolymerizations whereby the alkyl cobaloximes and related compounds, which are used as the photoinitiators, have alkyl groups, which may in essence, be polymers with carbon-cobalt chain ends, thereby allowing grafting reactions to occur to the polymer backbone.Type: GrantFiled: April 15, 1994Date of Patent: November 21, 1995Assignee: University of AkronInventors: Michael P. Greuel, Labros D. Arvanitopoulos, H. James Harwood
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Patent number: 5468784Abstract: Disclosed is a photopolymerizable resin composition suitable for forming a solder mask layer, for example, on a printed circuit board. The photopolymerizable resin composition of the invention can be prepared in the form of an aqueous solution and is developable with water as the developer liquid so that the problems and disadvantages inherent in the use of organic solvents can be completely solved. The composition comprises, in addition to a photopolymerization initiator and a polyenic compound as a reactive diluent, a unique prepolymer as a resinous ingredient which is a copolymer of, for example, an alkyl (meth)acrylate and glycidyl (meth)acrylate modified at the epoxy groups in the copolymer partly by the reaction with (meth)acrylic acid and partly by the reaction with an onium group-containing compound, e.g. a quaternary ammonium compound, to impart solubility in water.Type: GrantFiled: February 23, 1994Date of Patent: November 21, 1995Assignee: Tamura Kaken CorporationInventors: Makoto Yanagawa, Hiroshi Yamamoto
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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: 5459174Abstract: A radiation curable functionalized polymer is disclosed. The functionalized polymer is a copolymer of an isoolefin of 4 to 7 carbon atoms and para-alkylstyrene, wherein the para-alkylstyrene is functionalized with an acrylate or a mixture of acrylates and/or a photosensitizer and/or other functional groups at the para-alkyl groups of the para-alkylstyrene.Type: GrantFiled: June 24, 1994Date of Patent: October 17, 1995Inventors: Natalie A. Merrill, Hsian-Chang Wang, Anthony J. Dias
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Patent number: 5446074Abstract: New photosensitive polyamic acid precursors are disclosed which have the formula: ##STR1## where Z is a tetravalent organic radical which contains at least one aromatic ring, Z' is a divalent organic radical which contains at least one aromatic ring, and R* is a photosensitive group. Particularly preferred compounds include BPDA-PDA and BPDA-ODA polyamic acid precursors. The precursor compositions within the practice of this invention are i-line, g-line, and i-/g-line active and show good photoresolution. The films formed exhibit excellent self-adhesion and adhesion to glass ceramic and silicon wafer substrates have low internal stress, a very low degree of solvent swelling, high thermal stability, and excellent mechanical properties such as high modulus/tensile strength and high elongation at break.Type: GrantFiled: December 17, 1993Date of Patent: August 29, 1995Assignee: International Business Machines CorporationInventors: George Czornyj, Moonhor Ree, Willi Volksen, Dominic C. Yang
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Patent number: 5438082Abstract: In order to produce a polymer electrolyte membrane from sulfonated, aromatic polyether ketone, an aromatic polyether ketone of the formula (I) ##STR1## in which Ar is a phenylene ring having p- and/or m-bonds,Ar' is a phenylene, naphthylene, biphenylene, anthrylene or another divalent aromatic unit,X, N and M, independently of one another are 0 or 1,Y is 0, 1, 2 or 3,P is 1, 2, 3 or 4,is sulfonated and the sulfonic acid is isolated. At least 5% of the sulfonic groups in the sulfonic acid are converted into sulfonyl chloride groups, and these are reacted with an amine containing at least one crosslinkable substituent or a further functional group, and unreacted sulfonyl chloride groups are subsequently hydrolyzed. The resultant aromatic sulfonamide is isolated and dissolved in an organic solvent, the solution is converted into a film, and the crosslinkable substituents in the film are then crosslinked.In specific cases, the crosslinkable substituents can be omitted.Type: GrantFiled: June 10, 1993Date of Patent: August 1, 1995Assignee: Hoechst AktiengesellschaftInventors: Freddy Helmer-Metzmann, Frank Osan, Arnold Schneller, Helmut Ritter, Konstantin Ledjeff, Roland Nolte, Ralf Thorwirth
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Patent number: 5407971Abstract: Disclosed are radiation-crosslinkable elastomeric compositions containing:(a) an elastomeric polymer containing abstractable hydrogen atoms in an amount sufficient to enable the elastomeric polymer to undergo crosslinking in the presence of a suitable radiation-activatable crosslinking agent; and(b) a radiation-activatable crosslinking agent of the formula: ##STR1## wherein: W represents --O--, --N--, or --S--;X represents CH.sub.3 -- or ##STR2## Y represents a ketone, ester, or amide functionality; Z represents an organic spacer which does not contain hydrogen atoms that are more photoabstractable than hydrogen atoms of the elastomeric polymer;m represents an integer of 0 to 6;a represents 0 or 1; andn represents an integer of 2 or greater.Radiation-crosslinked elastomers are prepared by exposing the radiation-crosslinkable elastomeric compositions to radiation (e.g., UV light) to abstract hydrogen atoms from the elastomeric polymer by the resulting radiation-activated crosslinking agent.Type: GrantFiled: January 26, 1994Date of Patent: April 18, 1995Assignee: Minnesota Mining and Manufacturing CompanyInventors: Albert I. Everaerts, Audrey A. Sherman, Charles M. Leir
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Patent number: 5401614Abstract: An antireflective coating composition for use with chemically amplified photoresist compositions comprising a polymer composition which is highly absorbent to mid and deep UV radiation, which is substantially inert to contact reactions with a chemically amplified photoresist composition, and which is insoluble in the developer for the chemically amplified photoresist composition.Type: GrantFiled: February 16, 1993Date of Patent: March 28, 1995Assignee: International Business Machines CorporationInventors: Robert R. Dichiara, James T. Fahey, Pamela E. Jones, Christopher F. Lyons, Wayne M. Moreau, Ratnam Sooriyakumaran, Gary T. Spinillo, Kevin M. Welsh, Robert L. Wood
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Patent number: 5395733Abstract: An image forming layer comprising a polymer which has a component showing UV absorption at 320 nm or higher and a component containing the carboxylic acid (carboxylate) group represented by the following general formula I:--(Y).sub.1 --X--(CH.sub.2).sub.k --COOT (I)wherein X represents sulfur, oxygen, single bond, C.dbd.W or N--U where W represents oxygen or sulfur and U represents an optionally substituted aryl, alkyl group or hydrogen, Y represents an optionally substituted alkylene, arylene, aralkylene group or divalent heterocyclic ring, and T represents a hydrogen, alkali metal, alkaline earth metal or HN(R.sup.1)(R.sup.2)(R.sup.3) where R.sup.1, R.sup.2 and R.sup.3, which may be identical or different, independently represent a hydrogen atom, optionally substituted alkyl or aryl group and R.sup.1, R.sup.2 and R.sup.3 may join together to form a ring structure, k represents 0 or 1 and 1 is 0 or 1, provided that X represents C.dbd.W when k is 0.Type: GrantFiled: May 10, 1991Date of Patent: March 7, 1995Assignee: Fuji Photo Film Co., Ltd.Inventors: Kazuo Maemoto, Kouichi Kawamura
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Patent number: 5380621Abstract: An antireflective coating composition (ARC) for use with chemically amplified photoresist compositions comprising a polymer composition which is highly absorbent to mid and deep UV radiation, which is substantially inert to contact reactions with a chemically amplified photoresist composition, and which is insoluble in the developer for the chemically amplified photoresist composition.Type: GrantFiled: May 3, 1993Date of Patent: January 10, 1995Assignee: International Business Machines CorporationInventors: Robert R. Dichiara, Christopher F. Lyons, Ratnasabapathy Sooriyakumaran, Gary T. Spinillo, Kevin M. Welsh, Robert L. Wood
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Patent number: 5376503Abstract: A lithographic coating and method of framing a lithographic image are disclosed. The method comprises coating at least a portion of a surface of an article with a radiation-crosslinkable polymer, and exposing the coated surface to a pattern of radiation to crosslink the polymer in a lithographic image. The functionalized polymer is a copolymer of an isoolefin of 4 to 7 carbon atoms and para-alkylstyrene, wherein the para-alkylstyrene is functionalized with a radiation reactive group at the para-alkyl group of the para-alkylstyrene.Type: GrantFiled: November 24, 1992Date of Patent: December 27, 1994Assignee: Exxon Chemical Patents Inc.Inventors: Jay D. Audett, Kenneth O. McElrath
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Patent number: 5361616Abstract: A coating composition having photopolymerizability and heat curability, which comprises, as main components,(A) a vinyl copolymer having polymerizable double bonds and crosslinkable hydroxyl groups,(B) a condensation polymerizable compound of the following formula (i) or a condensation polymer thereof, and(C) a photopolymerization initiator: ##STR1## wherein each of the plurality of R which may be the same or different, is --H, --CH.sub.2 OH, --CH.sub.2 OCH.sub.3, --CH.sub.2 OC.sub.4 H.sub.Type: GrantFiled: June 9, 1992Date of Patent: November 8, 1994Assignee: Dai Nippon Toryo Co., Ltd.Inventors: Toshiya Takahashi, Norio Uriya, Yoshihisa Nagashima
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Patent number: 5356947Abstract: The present invention provides controllably curable photoiniferter containing adhesive compositions which are suitable for the mounting of microelectronic devices such as flip chips onto transparent wiring boards, a method of making the adhesive compositions, and a method of using the adhesive compositions in order to bond microelectronic devices to transparent wiring boards by intermittent exposure of the adhesive composition to a radiant energy source. The adhesive compositions can be cured in a stepwise fashion by intermittent controlled exposure to a source of radiation thus providing exactly the amount of cure and hardening desired.Type: GrantFiled: October 29, 1992Date of Patent: October 18, 1994Assignee: Minnesota Mining and Manufacturing CompanyInventors: Mahfuza B. Ali, Jean M. Pujol
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Patent number: 5318999Abstract: The present invention provides a novel dental composition and a method of making shaped dental articles therefrom via photoiniferter polymerization. The dental composition comprises acrylic photoiniferter block polymer, a monomer charge comprising free radically polymerizable acrylic monomer, and a filler and optionally includes pigments, sensitizers, medicaments, stabilizers, accelerators, etc. The dental composition is alternately exposed to a source of radiant energy and shaped in a desired manner in order to form a partially cured dental article. The partially cured dental article is then cured by a final exposure to the radiant energy source, providing a final cured article. The resultant reinforced acrylic copolymer system provides a shaped dental article which can be a denture base, a denture liner or a restorative.Type: GrantFiled: October 8, 1991Date of Patent: June 7, 1994Assignee: Minnesota Mining and Manufacturing CompanyInventors: Sumita B. Mitra, Mahfuza B. Ali
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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: 5298361Abstract: A light-sensitive article comprising (a) at least one layer of photopolymerizable material containing a polymerizable compound having at least one ethylenically unsaturated group, and a chromophore-substituted halomethyl-1,3,5-triazine photopolymerization initiator; (b) at least one layer of thermoplastic resin in contact with the layer of photopolymerizable material, said chromophore-substituted 1,3,5-triazine photopolymerization initiator capable of resisting migration to said layer of thermoplastic resin. The invention eliminates the problem of discoloration of the background resulting from excessive migration of the photoinitiator from the layer of photopolymerizable material to the contiguous layer of resin. The invention is especially useful in the preparation of surprint color proofs.Type: GrantFiled: August 30, 1991Date of Patent: March 29, 1994Assignee: Minnesota Mining and Manufacturing CompanyInventor: James A. Bonham
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Patent number: 5294688Abstract: The invention relates to UV-crosslinkable copolymers built up fromA) from 99.5 to 75% by weight of olefinically unsaturated monomers,B) from 0.5 to 25% by weight of unsaturated compounds of the formula I ##STR1## and C) from 0.01 to 10% by weight of copolymerizable, olefinically unsaturated acetophenone and/or benzophenone derivatives containing no phenyl group having a free hydroxyl group in the ortho-position to the carbonyl group, whereX is O, S or NR.sup.1 andR is unsubstituted or substituted C.sub.2 - to C.sub.6 -alkylene, andR.sup.1 is C.sub.1 - to C.sub.8 -alkyl or phenyl.The copolymers according to the invention are suitable, after crosslinking, as coating agents, impregnants or adhesives and in particular as contact adhesives.Type: GrantFiled: November 16, 1992Date of Patent: March 15, 1994Assignee: BASF AktiengesellschaftInventors: Gerd Rehmer, Gerhard Auchter, Andreas Boettcher, Lothar Franz, Helmut Jaeger
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Patent number: 5276069Abstract: Synthetic resins are obtainable by chemically bonding one or more compounds of the general formula I ##STR1## where R.sup.1 is --OH, --NH.sub.2, ##STR2## --NHR.sup.3 or ##STR3## R.sup.2 is --H, --CH.sub.3 or --C.sub.2 H.sub.5, R.sup.3 is --C.sub.m H.sub.2m+1, where m is from 1 to 6, R.sup.4 is --H or --CH.sub.3 and n is from 1 to 12, via the oxygen or nitrogen atom of R.sup.1 to one or more polymers A which consist ofa) from 50 to 100% by weight of one or more esters of acrylic or methacrylic acid with monohydric alcohols of 1 to 18 carbon atoms or a mixture of these esters (monomers a) andb) from 0 to 50% by weight of other copolymerizable monomers (monomers b) in polymerized form,in amounts such that the synthetic resin contains from 0.01 to 1 mole of double bonds per kg of polymer A.After exposure to ultraviolet light or to electrons, these synthetic resins are suitable as contact adhesives.Type: GrantFiled: May 3, 1991Date of Patent: January 4, 1994Assignee: BASF AktiengesellschaftInventors: Gerd Rehmer, Gerhard Auchter, Helmut Jaeger
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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: 5248805Abstract: Radiation-sensitive, ethylenically unsaturated compounds and a process for their preparation. The ethylenically unsaturated organic compounds are of the general formula ##STR1## where R is alkyl, aryl or a radical R.sup.1 andR.sup.1 is a radical ##STR2## where R.sup.2 to R.sup.6 are each H, alkyl, OH, OAlkyl, SH, SAlkyl, halogen, N (Alkyl).sub.2 or N (Alkyl) (Aryl) and at least one but not more than three of the radicals R.sup.2 to R.sup.6 is or are a radical ##STR3## where X is alkylene, cycloalkylene, oxaalkylene or arylene, Y is H or CH.sub.3 -- and Z is O or NY.The novel radiation-sensitive ethylenically unsaturated compounds are suitable for the preparation of polymeric radiation-sensitive compounds.Type: GrantFiled: March 2, 1992Date of Patent: September 28, 1993Assignee: BASF AktiengesellschaftInventors: Andreas Boettcher, Gerd Rehmer
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Patent number: 5215860Abstract: Energy polymerizable compositions comprising at least one cyanate monomer and as curing agent an organometallic compound are disclosed. The compositions are useful in applications requiring high performance, such as high temperature performance; in composites, particularly structural composities; structural adhesives; tooling for structural composities; electronic applications such as printed wiring boards and semiconductor encapsulants; graphic arts; injection molding and prepregs; and high performance binders.Type: GrantFiled: August 19, 1988Date of Patent: June 1, 1993Assignee: Minnesota Mining and Manufacturing CompanyInventors: Fred B. McCormick, Katherine A. Brown-Wensley, Robert J. DeVoe
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Patent number: 5200299Abstract: Compounds of the general formula I ##STR1## are described in which R.sup.1 is a group of the formula ##STR2## and R.sup.2 is a hydrogen atom or a methyl group, orR.sup.1 and R.sup.2 jointly form an optionally substituted 5- or 6-membered ring,R.sup.3 is a hydrogen atom, a methyl group or an optionally substituted phenyl group,R.sup.4 is a hydrogen or halogen atom, a methyl group, an optionally substituted benzoyl group or a group of the formula ##STR3## n is zero or 1, X is a hydrogen or chlorine atom, an alkyl group containing 1 to 4 carbon atoms or one of the groups OA, CH.sub.2 OA, CH.sub.2 NHA or C.sub.2 H.sub.4 OA, andA is an acryloyl or methacryloyl group,the compounds containing in each case at least one group A. The compounds are suitable for the production of photoresists and printing plates as diffusion-resistant photoinitiators in photopolymerizable mixtures.Type: GrantFiled: December 21, 1989Date of Patent: April 6, 1993Assignee: Hoechst AktiengesellschaftInventors: Hartmut Steppan, Hans-Dieter Frommeld
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Patent number: 5128386Abstract: UV-crosslinkable materials based on (meth)acrylate copolymers contain copolymerized monomers of the general formula I ##STR1## where R is a certain alkyl radical, an aryl radical or a radical R.sup.1 and R.sup.1 is a radical ##STR2## where R.sup.2 to R.sup.6 are each H, alkyl, a non-ortho OH group, OCH.sub.3, OC.sub.2 H.sub.3, SH, SCH.sub.3, Cl, F, CN, COOH, COO(C.sub.1 -C.sub.3 -alkyl), CF.sub.3, N(CH.sub.3).sub.2, N(C.sub.2 H.sub.5).sub.2, N(CH.sub.3)C.sub.6 H.sub.5, .sup.+ N(CH.sub.3).sub.3 X.sup.- or .sup.+N(CH.sub.3).sub.X X.sup.-, where X.sup.- is an acid anion, and one or more of the radicals R.sup.2 to R.sup.Type: GrantFiled: December 15, 1989Date of Patent: July 7, 1992Assignee: BASF AktiengesellschaftInventors: Gerd Rehmer, Andreas Boettchher, Gerhard Auchter
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Patent number: 5095044Abstract: Compounds of the formula I ##STR1## in which n is 1-30 and X, Y, R, Ar.sup.1 and Ar.sup.2 are as defined in claim 1 can be prepared by reaction of a benzil dialkyl ketal with a diol. Depending on the molar ratio of the two reaction components, products having a different polycondensation degree n are obtained. the compounds can be used as photoinitiators.Type: GrantFiled: April 27, 1990Date of Patent: March 10, 1992Assignee: Ciba-Geigy CorporationInventors: Rinaldo Husler, Rudolf Kirchmayr, Werner Rutsch, Manfred Rembold
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Patent number: 5093223Abstract: The invention provides a method of forming a cured coating film which comprises exposing a coating composition consisting of, or containing as a main component, a resin containing polymerizable unsaturated group and aprotic onium-containing group of the formula ##STR1## wherein R.sub.1 means a hydrogen atom or a hydrocarbon group of 1 to 8 carbon atoms which may optionally be substituted by a hydroxyl, alkoxy or ester group or a halogen atom; ##STR2## where Z means a nitrogen atom or phosphorus atom and Y means a sulfur atom; R.sub.2, R.sub.3 and R.sub.4 are the same or different and respectively mean an organic group of 1 to 14 carbon atoms, provided that R.sub.2 and R.sub.3, or R.sub.2, R.sub.3 and R.sub.4 may jointly form a heterocyclic group taken together with the adjacent nitrogen, phosphorus or sulfur atom, to actinic radiation or electron beams to thereby induce a crosslinking reaction and, then, subjecting the composition to heat treatment at a temperature not less than 80.degree. C.Type: GrantFiled: December 1, 1988Date of Patent: March 3, 1992Assignee: Kansai Paint Company, LimitedInventors: Naozumi Iwasawa, Osamu Isozaki
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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: 5087550Abstract: Radiation-reactive mixtures suitable for producing insulating layers and printed circuits are composed of certain precursors for preparing polyimides, polyisoindoloquinazolinediones, polyoxiazinediones, polyquinazolinediones or polyquinazolones and aryl-containing carbonyl compounds which when excited by UV radiation are capable of hydrogen abstraction, these mixtures undergoing solubility differentiation on irradiation with actinic light.Type: GrantFiled: September 26, 1989Date of Patent: February 11, 1992Assignee: BASF AktiengesellschaftInventors: Rainer Blum, Gerd Rehmer, Hans Schupp
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Patent number: 5071732Abstract: Radiation-curable two-layer systems containing immobilized photoinitiators are suitable for the production of coatings of constant thickness and good adhesion, and relief structures of high resolution and edge steepness.Type: GrantFiled: December 14, 1989Date of Patent: December 10, 1991Assignee: Merck Patent Gesellschaft Mit Beschrankter HaftungInventors: Manfred Kohler, Eike Poetsch, Jorg Ohngemach, Dieter Dorsch, Rudolf Eidenschink, Gerhard Greber
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Patent number: 5070118Abstract: Polysiloxane is produced containing both acrylic or methacrylic and benzoyl functions which is self-sensitized to UV radiation.Type: GrantFiled: January 22, 1991Date of Patent: December 3, 1991Assignee: General Electric CompanyInventor: Richard P. Eckberg
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Patent number: 5043362Abstract: Water-processable screenprinting stencils and resists are based upon photopolymerizable systems in which the hydrogen donor compound is a modified polyvinylalcohol having pendant dialkylamino groups.Type: GrantFiled: June 28, 1988Date of Patent: August 27, 1991Assignee: Autotype International LimitedInventors: Ross A. Balfour, John A. Sperry
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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: 4933398Abstract: A curable composition comprising (a) an epoxy resin, (b) a hardener if necessary, (c) an anthraquinone of formula I ##STR1## wherein R.sup.1 is --COOH or a radical of formula II ##STR2## wherein n is 0 or a number from 1 to 12, R.sup.2 is H, C.sub.1 -C.sub.12 -alkyl or --CN and R.sup.3 is H, --CN or the radical --C.sub.m H.sub.2m X, where m is 0 or a number from 1 to 12 and X is --COOH or --CN, and (d) an amino alcohol. The cured compositions are photosensitive and are suitable for the preparation of metallic coatings and images by electroless metal deposition.Type: GrantFiled: June 20, 1988Date of Patent: June 12, 1990Assignee: Ciba-Geigy CorporationInventors: Walter Fischer, Jurgen Finter