Contains Compound Containing Keto Group Not Part Of A Ring And A Specified Rate-affecting Material; Or Contains A Specified Rate-affecting Material And A Nonspecified Photoinitiator Or Photosensitizer Patents (Class 522/12)
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Patent number: 7091256Abstract: A reactive paint to be completely cured in air with binders that bear ethylenically-unsaturated groups, that can be cured by radical polymerization either thermally or both thermally and by UV light or high-energy radiation in a dual-cure method. The paint contains a combined initiator system consisting of thermal initiators and UV initiators and reactive oligomers that are formed from addition compounds of a reactant of formula (4) and a reactant of formula (5) In this formula, X=—CO—CH?CH2 or —CnHm or —CO—CnHm. —CnHm is an aliphatic residue with 1 to 3 C atoms, whereby 0, 1, 2 or 3 X substituents are formed by —CnHm, and Y is a hydrocarbon chain of 3 to 8 atoms that can also contain heteroatoms. Also provided is a method for curing by radical polymerization. The polymerization is first started thermally under air and then is continued either thermally or photoinitiated under air or protective gas, and a use in paint systems, especially in automobile manufacturing or as a binder.Type: GrantFiled: June 22, 2004Date of Patent: August 15, 2006Assignee: DaimlerChrysler AGInventors: Markus Bischof, Elisabeth Gemmler, Fritz Mezger, Thomas Raith, Christoph Ruechardt
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Patent number: 6967042Abstract: The present invention discloses an ultraviolet light curable mar resistant composition and method for making such a composition that may be used to produce an mar resistant layer. The disclosed composition does not contain any significant amount of volatile organic solvents that do not become incorporated in the active layer after curing.Type: GrantFiled: November 15, 2002Date of Patent: November 22, 2005Assignee: Allied PhotoChemical, Inc.Inventor: Roy C. Krohn
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Patent number: 6908644Abstract: The present invention discloses a photocurable composition that is combinable with a thermally curable clearcoat composition to form a dual curable composition that is useful for forming clearcoats with improved sag resistance. The photocurable composition of the invention includes at least one photocurable oligomer; a first photoinitiator that absorbs light in a first spectral region such that curing of the photocurable composition preferentially occurs near the surface of the of the coating; and a second photoinitiator that absorbs light in a second spectral region such that curing of the photocurable composition occurs throughout the coating. The present invention also provides a method of coating a substrate with a dual curable composition.Type: GrantFiled: February 4, 2003Date of Patent: June 21, 2005Assignee: Ford Global Technologies, LLCInventor: Timothy P. Weingartz
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Patent number: 6906114Abstract: The present invention discloses an ultraviolet light curable silver chloride compositions and method for making such a composition that may be used to produce a silver coating on a substrate. The disclosed composition does not contain any significant amount of volatile organic solvents that do not become incorporated in the active layer after curing.Type: GrantFiled: September 6, 2001Date of Patent: June 14, 2005Assignee: Allied PhotoChemical, Inc.Inventor: Roy C. Krohn
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Patent number: 6897248Abstract: The present invention discloses an ultraviolet light curable ferromagnetic composition and method for making such a composition that may be used to produce a ferromagnetic coating on a suitable substrate. These coatings may be used to produce printed capacitors and inductors. The disclosed composition does not contain any significant amount of volatile organic solvents that do not become incorporated in the active layer after curing.Type: GrantFiled: February 24, 2004Date of Patent: May 24, 2005Assignee: Allied PhotoChemical, Inc.Inventor: Roy C. Krohn
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Patent number: 6866899Abstract: A two-step method of polymerizing a composition containing a free radical photoinitiator includes the sequential steps of exposing the composition to a first radiation source having a maximum spectral output occurring at a wavelength of greater than 300 nm and, thereafter, exposing the composition to a second radiation source having a maximum spectral output occurring at a wavelength of less than 300 nm.Type: GrantFiled: December 21, 2001Date of Patent: March 15, 2005Assignee: 3M Innovative Properties CompanyInventor: Robin E. Wright
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Patent number: 6867241Abstract: The present invention relates to a radiation-curable composition which includes a cyanoacrylate component or a cyanoacrylate-containing formulation, a metallocene component, a hydrogen abstraction photoinitiator, and hydrogen donor component to enhance the activity of the hydrogen abstraction photoinitiator.Type: GrantFiled: January 31, 2002Date of Patent: March 15, 2005Assignee: Henkel CorporationInventors: Stan Wojciak, Shabbir Attarwala, John T. O'Connor, S. Peter Pappas
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Patent number: 6797740Abstract: The invention relates to a radiation curable colored coating composition for coloring a coated optical fiber wherein the coating, when disposed and cured to surround an optical fiber coated with an internal coating, and when said colored fiber is coated with a matrix material and assembled into an optical fiber ribbon, said colored coating has a degree of adhesion to the internal coating which is higher than the degree of adhesion to the matrix material and said optical fiber assembled into said optical fiber ribbon shows, upon aging for at least two weeks in water at 60° C., an increase in the attenuation of the transmitted signal at 1550 nm of less than 0.05 db/km with respect to the attenuation of the assembled optical fiber measured before aging. The invention also relates to said colored coating composition when used in an optical fiber ribbon.Type: GrantFiled: December 17, 2002Date of Patent: September 28, 2004Assignee: DSM N.V.Inventors: Adrianus G. M. Abel, Albert A Vries De, Gouke D. J. Geus, Johannes C Burg Van Den, Johannes A Eekelen Van, Alessandro Ginocchio, Massimo Pizzorno
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Patent number: 6716893Abstract: The present invention discloses an ultraviolet light curable ferromagnetic composition and method for making such a composition that may be used to produce a ferromagnetic coating on a suitable substrate. These coatings may be used to produce printed capacitors and inductors. The disclosed composition does not contain any significant amount of volatile organic solvents that do not become incorporated in the active layer after curing.Type: GrantFiled: July 11, 2002Date of Patent: April 6, 2004Assignee: UV Specialties, Inc.Inventor: Roy C. Krohn
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Patent number: 6713524Abstract: The invention relates to novel reactive polymers of formula wherein the variables are as defined in the claims. The polymers of the invention are useful for the modification of material surfaces and are particularly suitable for providing biomedical articles such as contact lenses with a hydrophilic coating.Type: GrantFiled: March 9, 2001Date of Patent: March 30, 2004Assignee: Novartis AGInventors: Jörg Leukel, Peter Chabrecek, Dieter Lohmann
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Publication number: 20040013977Abstract: A liquid radiation-curable composition that comprisesType: ApplicationFiled: January 7, 2003Publication date: January 22, 2004Applicant: 3D Systems, Inc.Inventor: Bettina Steinmann
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Publication number: 20030130369Abstract: A two-step method of polymerizing a composition containing a free radical photoinitiator includes the sequential steps of exposing the composition to a first radiation source having a maximum spectral output occurring at a wavelength of greater than 300 nm and, thereafter, exposing the composition to a second radiation source having a maximum spectral output occurring at a wavelength of less than 300 nm.Type: ApplicationFiled: December 21, 2001Publication date: July 10, 2003Applicant: 3M Innovative Properties CompanyInventor: Robin E. Wright
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Patent number: 6583196Abstract: A high refractive index composition comprising a core resin mixture comprising a first compound of formula (I), a second compound of a poly(ethylene glycol) di(meth)acrylate of formula (II) and a reactive diluent to provide enhanced impact resistance and refractive index.Type: GrantFiled: December 27, 2000Date of Patent: June 24, 2003Assignee: Rodenstock North America, Inc.Inventor: Qiang Zheng
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Patent number: 6518326Abstract: The invention relates to open chain alkoxyamine compounds useful as polymerization regulators. The open chain alkoxyamine compounds are useful for the polymerization of ethylenically unsaturated monomers. The compounds of the present invention provide polymeric resin products having low polydispersity. The polymerization process proceeds with enhanced monomer to polymer conversion efficiency. In particular, this invention relates to stable free radical-mediated polymerization processes which provide homopolymers, random copolymer, block copolymers, multiblock copolymers, graft copolymers and the like, at enhanced rates of polymerization and enhanced monomer to polymer conversions.Type: GrantFiled: January 29, 2001Date of Patent: February 11, 2003Assignee: Ciba Specialty Chemicals CorporationInventors: Peter Nesvadba, Andreas Kramer, Marie-Odile Zink, Dario Lazzari
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Patent number: 6509389Abstract: The present invention discloses an ultraviolet light curable mar resistant composition and method for making such a composition that may be used to produce an mar resistant layer. The disclosed composition does not contain any significant amount of volatile organic solvents that do not become incorporated in the active layer after curing.Type: GrantFiled: September 25, 2000Date of Patent: January 21, 2003Assignee: UV Specialties, Inc.Inventor: Roy C. Krohn
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Patent number: 6503959Abstract: A photocurable composition comprising (A) an &agr;-cyanoacrylate and (B) a metallocene compound comprising a transition metal of Group VIII of the periodic table and aromatic electron system ligands selected from &pgr;-arenes, indenyl, &eegr;-cyclopentadienyl. The photocurable composition may further comprise (C) a cleavage-type photoinitiator. The photocurability of the photocurable composition can be greatly improved by incorporating a cleavage type photoinitiator into the composition. Even when the composition contains a radical-polymerizable compound such as an acrylic compound, it can be rapidly cured due to the cleavage type photoinitiator contained therein. In the case where the cleavage-type photoinitiator used is a peroxide, heating can also be used to cure the composition. In the case where the cleavage type photoinitiator used is an azo compound, the composition can be foamed by regulating the addition amount of the photoinitiator or the quantity of light with which the composition is irradiated.Type: GrantFiled: October 11, 1996Date of Patent: January 7, 2003Assignee: Three Bond Co., Ltd.Inventors: Yuko Nishiyama, Hiroyuki Mikuni
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Patent number: 6495627Abstract: A conductive composition for a biological electrode is capable of reducing the impedance between the electrode and the skin. A conductive gel composition for a biological electrode which is capable of electrically and physically connecting a living body to an electrode element and is composed of at least the following components: (1) a radical-polymerizable unsaturated compound; (2) a moisturizer serving as a plasticizer and functioning to supplementing and promoting the physiological humidifying function of the horny layer; (3) a polymerization initiator; and (4) a crosslinking agent. This moisturizer serves also as a plasticizer and, furthermore, elevates the moisture content in the horny layer at the application of this composition. The above-mentioned composition may further contain a plasticizer selected from among polyhydric alcohols, amines and ethers.Type: GrantFiled: July 11, 1996Date of Patent: December 17, 2002Assignee: Nihon Kohden CorporationInventors: Shin Suda, Tohru Kurata
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Patent number: 6406913Abstract: Methods are disclosed for determining an analyte in a medium suspected of containing the analyte. One method comprises treating a medium suspected of containing an analyte under conditions such that the analyte, if present, causes a photosensitizer and a chemiluminescent compound to come into close proximity. The photosensitizer generates singlet oxygen and activates the chemiluminescent compound when it is in close proximity. The activated chemiluminescent compound subsequently produces light. The amount of light produced is related to the amount of analyte in the medium. Preferably, at least one of the photosensitizer and chemiluminescent compound is associated with a surface which is usually a suspendible particle, and a specific binding pair member is bound thereto. Compositions and kits are also disclosed.Type: GrantFiled: June 6, 1995Date of Patent: June 18, 2002Assignee: Dade Behring Marburg GmbHInventors: Edwin F. Ullman, Hrair Kirakossian, John S. Pease, Yuri Daniloff, Daniel B. Wagner
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Patent number: 6335382Abstract: An ultraviolet-curable adhesive having an excellent moisture resistance and suitable for bonding optical disks having an information recording layer (vapor deposition layer), particularly optical disks having a thick vapor deposition layer, which contains, as essential components, (A) N-vinylpyrrolidone, (B) a urethane (meth)acrylate oligomer derived from a caprolactone-based polyol, an alicyclic diisocyanate and (meth)acrylic acid, and (C) a photopolymerization initiator containing (C-1) a photopolymerization initiator composed of only a carbon atom, a hydrogen atom and an oxygen atom without containing a nitrogen atom, a sulfur atom and a phosphorus atom and (C-2) a photopolymerization initiator containing a nitrogen atom and/or a sulfur atom in a (C-1)/(C-2) ratio of 70/30 to 100/0 by weight.Type: GrantFiled: January 6, 2000Date of Patent: January 1, 2002Assignee: Nagase-Ciba Ltd.Inventor: Takafumi Iida
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Patent number: 6326414Abstract: An ultraviolet-curable adhesive for bonding optical disks, which comprises (A) a radical-polymerizable vinyl compound, (B) an &agr;-hydroxyalkylphenone compound as a photopolymerization initiator, and (C) 2-methyl-1-[4-(methylthio)phenyl]-2-morpholino-propane-1-one, and which can provide optical disk products which are small in warping of disks, retain sufficient performances even under high temperature and high humidity and have a good appearance.Type: GrantFiled: February 29, 2000Date of Patent: December 4, 2001Assignee: Nagase Chemtex CorporationInventor: Takafumi Iida
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Patent number: 6284813Abstract: Compounds of the formula I in which R1 is C1-C4alkyl, R2 is hydrogen, C1-C4alkyl or C1-C4alkoxy and R3, R3, R4, R5, R6, and R7 independently of one another are hydrogen, halogen, C1-C20alkyl, cyclopentyl, cyclohexyl, C2-C12alkenyl, C2-C18 alkyl which is interrupted by one or more oxygen atoms, or are phenyl-substituted C1-C4alkyl, or are phenyl which is unsubstituted or is mono- or disubstituted by C1-C4alkyl and/or C1-C4alkoxy, with the provisos that at least one of the radicals R3, R4, R5, R6 and R7 is other than hydrogen and that, if R1 and R2 are methyl, R3 and R6 are not methyl, and mixtures of such compounds with &agr;-hydroxy ketones, benzophenones and &agr;-amino ketones, are suitable as photoinitiators.Type: GrantFiled: January 20, 1998Date of Patent: September 4, 2001Assignee: Ciba Specialty Chemicals Corp.Inventors: David George Leppard, Manfred Köhler, Andreas Valet
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Patent number: 6197422Abstract: Provided is a ribbon assembly having the functional capability of providing break-out of ink coated or colored outer primary coated optical glass fibers from the ribbon assembly. The ink coating or colored outer primary coating is formulated from a benzophenone compound and at least about 1 wt. % of a homolytic photoinitiator to provide a level of adhesion between the ink coating or colored outer primary coating and matrix material which is less than the level of adhesion between the ink coating or colored outer primary coating and an adjacent underlying coating. Also provided are ink coating and colored outer primary coating compositions adapted to form ink coatings and colored outer primary coatings suitable for use on optical glass fibers contained in a ribbon assembly.Type: GrantFiled: September 22, 1998Date of Patent: March 6, 2001Assignee: DSM, N.V.Inventors: Edward J. Murphy, Edward P. Zahora, Johannes C. van den Burg
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Patent number: 6140384Abstract: A photopolymerizable composition comprising i) an addition polymerizable compound having an ethylenically unsaturated double bond, ii) a sensitizing dye represented by the following formula (I) and iii) a titanocene compound: ##STR1## wherein A.sup.1 and A.sup.2 each represents a carbon atom or a hetero atom, Q.sup.1 represents a nonmetallic atom group necessary for forming a heterocyclic ring together with A.sup.1, A.sup.2 and the carbon atoms adjacent thereto, R.sup.1 and R.sup.2 each represents a hydrogen atom, an alkyl group or an aryl group and R.sup.1 and R.sup.2 may be combined with each other to form a ring, X.sup.1 and X.sup.2 each represents a cyano group or a substituted carbonyl group and X.sup.2 and X.sup.2 may be combined with each other to form a ring, and n represents 0, 1 or 2.Type: GrantFiled: October 1, 1997Date of Patent: October 31, 2000Assignee: Fuji Photo Film Co., Ltd.Inventors: Tadahiro Sorori, Yasuo Okamoto
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Patent number: 6096794Abstract: Dye compounds of the formula ##STR1## wherein X is for example CH, C--CH.sub.3 or .sup.+ NOR L.sup.- ; R is inter alia C.sub.1 -C.sub.6 alkyl; R.sub.1 is for example C.sub.1 -C.sub.8 alkoxy or C.sub.1 -C.sub.12 alkyl; s is 0 to 4; R.sub.2 is for example hydrogen; Ar is for example a group ##STR2## Y inter alia is C.sub.1 -C.sub.6 alkyl or C.sub.1 -C.sub.6 alkoxy; r in the formula (A) is 0 to 5, in the formulae (B) and (E) is 0 to 9 and in the formula (D) is 0 to 7; and L is an anion;in combination with an electron donor compound, especially a borate compound, are suitable as photoinitiators for the photopolymerization of radically polymerizable compositions.Type: GrantFiled: October 26, 1998Date of Patent: August 1, 2000Assignee: Ciba Specialty Chemicals CorporationInventors: Allan Francis Cunningham, Martin Kunz
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Patent number: 6057078Abstract: Compounds of the formula I ##STR1## in which n and o are a number from 0 to 50, m is a number from 1 to 50, u and v are 0 or 1, and at least one of the indices u and v is 1, R.sub.1, R.sub.2, R.sub.2a, R.sub.3 and R.sub.4 independently of one another are, for example, aromatic hydrocarbons, R.sub.5, if n and o are 0, is for example C.sub.1 -C.sub.12 alkyl and, if n and/or o are greater than 0, or if n and o are 0 and at the same time only one index u or v is 1, R.sub.5 may additionally, for example, be an aromatic hydrocarbon, at least one of the radicals R.sub.1, R.sub.2, R.sub.2a, R.sub.3, R.sub.4 and R.sub.5 being an aromatic hydrocarbon radical which is sterically hindered ortho to the boron atom, X is, for example, C.sub.1 -C.sub.20 alkylene, phenylene, biphenylene, etc., and Z is a radical which is able to form positive ions, are suitable as photoinitiators, both the compounds per se and their combination with dyes or other electron acceptors.Type: GrantFiled: July 23, 1998Date of Patent: May 2, 2000Assignee: Ciba Specialty Chemicals CorporationInventors: Allan Francis Cunningham, Martin Kunz, Hisatoshi Kura
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Patent number: 6017640Abstract: Opaquely pigmented or thick filmed powder coatings for heat sensitive substrates, such as wood, wood composites, for example, medium density fiber board, and plastics, that can be fully cured, especially near the substrate, through the incorporation of a dual cure system in the powder comprising a thermal initiator, such as a peroxide, along with a UV initiator. The UV initiator cures the surface, while the thermal initiator cures at the substrate. Surprisingly, virtually no pregelation occurs during the heated melt and flow out step prior to UV curing. Consequently, the hardened film finish formed on the surface exhibits exceptional smoothness which is comparable to that of traditional UV curable powders. The hardened film finish is also fully cured throughout and exhibits exceptional adhesion to the substrate which cannot be achieved with traditional UV curable powders that have been pigmented.Type: GrantFiled: April 23, 1999Date of Patent: January 25, 2000Assignee: Morton International, Inc.Inventors: Jeno Muthiah, Andrew T. Daly, Richard P. Haley, Joseph J. Kozlowski
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Patent number: 5994424Abstract: A free-radical curable polish composition is described. The composition can be applied and cured as an ultra thin film on finished surfaces to provide enhanced chemical and mar resistance. The composition comprises an aqueous emulsion including an olefin-functional polymer or an olefin-functional prepolymer, and a silicone or silicone copolymer preferably with photoinitiators for UV and EB cure. The polish/emulsion can be applied, for example, to wet the surface of nitrocellulose lacquer wood finishes. The polish wet surface is first wiped to remove excess polish and thereafter exposed to UV radiation to provide a thin, polymerized protective film.Type: GrantFiled: February 12, 1998Date of Patent: November 30, 1999Assignee: Lilly Industries, Inc.Inventors: Eugen Safta, Frank Chen, Greg Muselman, James V. Mirante, Danny R. Linthicum
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Patent number: 5922473Abstract: Opaquely pigmented or thick filmed powder coatings for heat sensitive substrates, such as wood, wood composites, for example, medium density fiber board, and plastics, that can be fully cured, especially near the substrate, through the incorporation of a dual cure system in the powder comprising a thermal initiator, such as a peroxide, along with a UV initiator. The UV initiator cures the surface, while the thermal initiator cures at the substrate. Surprisingly, virtually no pregelation occurs during the heated melt and flow out step prior to UV curing. Consequently, the hardened film finish formed on the surface exhibits exceptional smoothness which is comparable to that of traditional UV curable powders. The hardened film finish is also fully cured throughout and exhibits exceptional adhesion to the substrate which cannot be achieved with traditional UV curable powders that have been pigmented.Type: GrantFiled: December 26, 1996Date of Patent: July 13, 1999Assignee: Morton International, Inc.Inventors: Jeno Muthiah, Andrew T. Daly, Richard P. Haley, Joseph J. Kozlowski
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Patent number: 5885746Abstract: A photosensitive resin composition comprising a high polymer binder, a monomer, a photopolymerization initiator generating a radical on exposure to visible light of a wavelength of 400 to 700 nm such as triazine compounds, titanocene compounds, or acridine compounds, an optically-activated acid generating agent generating an acid on exposure to light of a wavelength of 200 to 380 nm, and a color former developing a color in the presence of an acid, and a method manufacturing a printing master plate comprising the steps of exposing a photosensitive printing plate which has a laminated layer made from a photosensitive resin composition thereon to visible light of wavelength in the range of 400 to 600 nm selectively in an imagewise configuration in order to harden the resin composition layer, developing the photosensitive printing plate, and further exposing the developed plate to light of a wavelength in the range 200 to 380 nm.Type: GrantFiled: December 28, 1995Date of Patent: March 23, 1999Assignee: Tokyo Ohka Kogyo Co., Ltd.Inventors: Takeshi Iwai, Hiroshi Komano
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Patent number: 5855837Abstract: A novel method for producing thick composite parts based upon photopolymerizable compositions is disclosed. The constituents of the photopolymerizable mixture comprise a monomer or monomers capable of polymerizing by free radical or cationic mechanisms, and a photoinitiator system which possesses an absorbance characteristic which is effectively reduced, or self-eliminating, upon initiation of the polymerization reaction. Parts having thicknesses up to 2 cm and thicker for varying end use applications are made by photopolymerizing such compositions. In addition, using such compositions composite parts can be made using a reinforcement material such as a glass fiber mat present in an amount by weight of from about 5 to about 70%.Type: GrantFiled: June 6, 1995Date of Patent: January 5, 1999Assignee: Michigan State UniversityInventors: Alec B. Scranton, Bharath Rangarajan, Lindsay S. Coons
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Patent number: 5843576Abstract: Floor coverings include a wear layer made from a coat composition including a multifunctional polyurethane (meth)acrylate oligomer. The multifunctional polyurethane is made by reacting a polyisocyanate with a functionality equal or higher than 3, a polyester polyol, and a hydroxyalkyl(meth)acrylate with a number average molecular weight of about 344 to about 472. The coating composition preferably includes a reactive (meth)acrylate diluent and a photoinitiator.Type: GrantFiled: November 3, 1997Date of Patent: December 1, 1998Assignee: Armstrong World Industries, Inc.Inventors: Angela S. Rosenberry, Claude R.. Rupp, Songvit Setthachayanon
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Patent number: 5837746Abstract: Compounds of the formulaRG--A--INwherein IN is a photoinitiator basic structure A is a spacer group and RG is a functional reactive group can be employed as coreactive photoinitiators for photo-polymerization of systems containing ethylenically unsaturated compounds.Type: GrantFiled: June 23, 1997Date of Patent: November 17, 1998Assignee: Ciba Specialty Chemicals CorporationInventors: Manfred Kohler, Jorg Ohngemach, Eike Poetsch, Rudolf Eidenschink, Gerhard Greber, Dieter Dorsch, Jurgen Gehlhaus, Konrad Dorfner, Hans Ludwig Hirsch
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Patent number: 5807905Abstract: Compounds of the formula I ##STR1## in which n and o are a number from 0 to 50, m is a number from 1 to 50, u and v are 0 or 1, and at least one of the indices u and v is 1, R.sub.1, R.sub.2, R.sub.2a, R.sub.3 and R.sub.4 independently of one another are, for example, aromatic hydrocarbons, R.sub.5, if n and o are 0, is for example C.sub.1 -C.sub.12 alkyl and, if n and/or o are greater than 0, or if n and o are 0 and at the same time only one index u or v is 1, R.sub.5 may additionally, for example, be an aromatic hydrocarbon, at least one of the radicals R.sub.1, R.sub.2, R.sub.2a, R.sub.3, R.sub.4 and R.sub.5 being an aromatic hydrocarbon radical which is sterically hindered ortho to the boron atom, X is, for example, C.sub.1 -C.sub.20 alkylene, phenylene, biphenylene, etc., and Z is a radical which is able to form positive ions, are suitable as photoinitiators, both the compounds per se and their combination with dyes or other electron acceptors.Type: GrantFiled: November 21, 1996Date of Patent: September 15, 1998Assignee: Ciba Specialty Chemicals CorporationInventors: Allan Francis Cunningham, Martin Kunz, Hisatoshi Kura
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Patent number: 5789459Abstract: 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: August 22, 1997Date of Patent: August 4, 1998Assignee: Mitsui Petrochemical Industries, Ltd.Inventors: Hajime Inagaki, Koji Yoshii
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Patent number: 5773485Abstract: Solute polymers in solvent monomers form a coatable syrup that can be cured to a viscoelastomeric material when radiation-sensitive hydrogen abstracting groups in either the polymer or one of the monomers are exposed to ultraviolet radiation. The solute polymers can be formed from the solvent monomers.Type: GrantFiled: August 23, 1995Date of Patent: June 30, 1998Assignee: Minnesota Mining and Manufacturing CompanyInventors: Greggory S. Bennett, Louis E. Winslow, Gaddam N. Babu
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Patent number: 5770345Abstract: 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: July 16, 1996Date of Patent: June 23, 1998Assignee: International Business Machines CorporationInventors: Edward Darko Babich, Karen Elizabeth Petrillo, John Patrick Simons, David Earle Seeger
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Patent number: 5753412Abstract: 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-l,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: June 5, 1996Date of Patent: May 19, 1998Assignee: International Business Machines CorporationInventors: Edward Darko Babich, Karen Elizabeth Petrillo, John Patrick Simons, David Earle Seeger
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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: 5719227Abstract: Floor coverings include a wear layer made from a coat composition including a multifunctional polyurethane (meth)acrylate oligomer. The multifunctional polyurethane is made by reacting a polyisocyanate with a functionality equal or higher than 3, a polyester polyol, and a hydroxyalkyl-(meth)acrylate with a number average molecular weight of about 344 to about 472. The coating composition preferably includes a reactive (meth)acrylate diluent and a photoinitiator.Type: GrantFiled: May 9, 1997Date of Patent: February 17, 1998Assignee: Armstrong World Industries, Inc.Inventors: Angela S. Rosenberry, Claude R. Rupp, Songvit Setthachayanon
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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: 5543262Abstract: A light sensitive composition which is capable of photopolymerization which includes a photopolymerizable compound a free radical generating component and a benzanthrone or substituted benzanthrone which substantially prevents photopolymerization when the light sensitive composition is exposed to actinic radiation below a threshold amount but permits photopolymerization when the light sensitive composition is exposed to actinic radiation above a threshold amount. This achieves a gate effect which eliminates or decreases unwanted partial exposure in the nonimage areas and hence improves reproduction quality.Type: GrantFiled: February 24, 1995Date of Patent: August 6, 1996Assignee: International Paper CompanyInventors: Maria T. Sypek, John R. Delude, Paul A. Perron
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Patent number: 5494944Abstract: A hardenable composition containing:a) a material polymerizable by free radical or cationic polymerization,b) at least one iron compound of the formula I ##EQU1## wherein a is 1 or 2 and q is 1, 2 or 3,L is a divalent to heptavalent metal or non-metal,Q is a halogen atom,m is an integer corresponding to the sum of the values of L and q,R.sup.1 is an unsubstituted or substituted .eta..sup.6 -benzene andR.sup.2 is an unsubstituted or substituted cyclopentadienyl anion, andc) at least one sensitizer for the compound of the formula I,and, in the case of materials polymerizable by free radical polymerization, also d) an electron acceptor as an oxidizing agent, which is also advantageously used concomitantly for the material polymerizable by cationic polymerization. The composition is suitable for the production of protective layers and photographic images.Type: GrantFiled: August 18, 1994Date of Patent: February 27, 1996Assignee: Ciba-Geigy CorporationInventors: Kurt Meier, Hans Zweifel
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Patent number: 5378734Abstract: A UV and moisture-curable organopolysiloxane composition comprising (i) an organopolysiloxane terminated with a radical of formula (1): ##STR1## wherein R.sup.1 is a hydrogen atom or monovalent hydrocarbon radical, each of R.sup.2 and R.sup.3 is a divalent hydrocarbon radical which may contain a NH bond or ether bond, each of R.sup.4 and R.sup.5 is a monovalent hydrocarbon radical which may contain an ether bond, and a is equal to 0 or 1, (ii) a photo-polymerization initiator, and (iii) a curing catalyst. The composition readily cures either upon exposure to UV radiation or upon contact with moisture and from the surface to the deep interior within a short time, yielding cured products having satisfactory physical properties.Type: GrantFiled: August 27, 1993Date of Patent: January 3, 1995Assignee: Shin-Etsu Chemical Company, Ltd.Inventor: Yoshio Inoue
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Patent number: 5371115Abstract: A hardenable composition containing:a) a material polymerizable by free radical or cationic polymerization,b) at least one iron compound of the formula I ##EQU1## wherein a is 1 or 2 and q is 1, 2 or 3,L is a divalent to heptavalent metal or non-metal,Q is a halogen atom,m is an integer corresponding to the sum of the values of L and q,R.sup.1 is an unsubstituted or substituted .eta..sup.6 -benzene andR.sup.2 is an unsubstituted or substituted cyclopentadienyl anion, andc) at least one sensitizer for the compound of the formula I,and, in the case of materials polymerizable by free radical polymerization, also d) an electron acceptor as an oxidizing agent, which is also advantageously used concomitantly for the material polymerizable by cationic polymerization. The composition is suitable for the production of protective layers and photographic images.Type: GrantFiled: April 15, 1992Date of Patent: December 6, 1994Assignee: Ciba-Geigy CorporationInventors: Kurt Meier, Hans Zweifel
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Patent number: 5340847Abstract: A composition useful as a liquid gasket, having high working efficiency and high initial pressure resistance, is provided. The composition, characterized by being curable by ultraviolet light and by moisture, includes (a) a polysiloxane containing, on at least one molecular end, at least one group selected from the group consisting of (meth)acryl, glycidyl, propenyloxysilyl and thiol; (b) a polyorganosiloxane having silanol groups at both molecular ends; (c) a polyorganosiloxane having, on at least one molecular end, a hydrolyzable group; (d) a photopolymerization catalyst; and (e) a condensation catalyst.Type: GrantFiled: July 23, 1993Date of Patent: August 23, 1994Assignee: Three Bond Co., Ltd.Inventors: Yasuo Hanazuka, Ikuzo Usami, Kazuyuki Chiba, Noriko Mizutani
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Patent number: 5300536Abstract: The present invention relates to a catalytic composition for photopolymerization, which comprises an alpha-diketone and a hydrazone or a silane compound which has a silicon atom carrying a hydrogen, and also relates to a photopolymerizable composition which comprises a vinyl compound capable of radical polymerization and the above catalytic composition. The catalytic composition is markedly improved in photopolymerization activity and the photopolymerizable composition uniformly cures.Type: GrantFiled: September 28, 1992Date of Patent: April 5, 1994Assignee: Toagosei Chemical Industry Co., Ltd.Inventors: Shin Takahashi, Yoshiaki Fujimoto
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Patent number: 5288917Abstract: Liquid highly active photoinitiators are obtained by dissolving a solid photoinitiator of the titanocene type in liquid photoinitiators of the acetal or ketal type. The liquid mixtures have a long dark storage stability.Type: GrantFiled: July 19, 1991Date of Patent: February 22, 1994Assignee: Ciba-Geigy CorporationInventors: Godwin Berner, Franciszek Sitek, Rinaldo Husler
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Patent number: 5212210Abstract: A composition and method provide improved physical properties and cure speed of polyurethane precursors, with or without free radical polymerizable monomers or oligomers present, by use of a two component catalyst system. The resin blend can be activated with a latent organometallic catalyst combined with an organic peroxide which can be a hydroperoxide or an acyl peroxide to decrease the cure time while increasing the break energy and tangent modulus of the system.Type: GrantFiled: March 18, 1992Date of Patent: May 18, 1993Assignee: Minnesota Mining and Manufacturing CompanyInventor: Leo W. Halm
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Patent number: 5180756Abstract: Agents which are curable by ultraviolet radiation are based on a binder formulation of (1) from 99.0 to 20% by weight of a copolymer, (2) from 1.0 to 80% by weight of monoolefinically unsaturated compounds and (3) from 0.0 to 20% by weight of polyolefinically unsaturated compounds. The agents contain copolymers (1) which are obtainable by subjecting 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 photoinitiator and (C) from 0 to 10% by weight of a polymerization-regulating photoinitiator 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 6, 1990Date of Patent: January 19, 1993Assignee: BASF AktiengesellschaftInventors: Gerd Rehmer, Andreas Boettcher
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Patent number: 5124235Abstract: A photopolymerization initiator comprises a borate salt represented by the general formula (I):M.sup.n.sym. (B.sup..crclbar. R.sup.1 R.sup.2 R.sup.3 R.sup.4).sub.nwherein R.sup.1, R.sup.2, R.sup.3, and R.sup.4 are respectively any one of halogen atoms, alkyl radicals, alkenyl radicals, alkynyl radicals, alicyclic radicals, aryl radicals, aryloxyl radicals, alkoxyl radicals, aralkyl radicals, and heterocyclic radicals, and may be the same with or different from each other; R.sup.1 and R.sup.2, or R.sup.2 and R.sup.3 may be linked to form a ring; M is an atom of a metal selected from Groups IB, IIB, IIIA, and IVA of the periodic table; and n is an integer of 1 or 2.A photosensitive composition comprises at least a polymerization compound and a photopolymerization initiator represented by the above general formula (I).Type: GrantFiled: September 9, 1991Date of Patent: June 23, 1992Assignee: Canon Kabushiki KaishaInventors: Tetsuro Fukui, Kyo Miura, Yoshio Takasu