From Monomer Containing A Carbonate Group, I.e., -o-c(=o)-o- Patents (Class 526/314)
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Patent number: 5336743Abstract: A cast resin for optical use is obtained by polymerizing a diallylphthalate component represented by the formula: ##STR1## wherein --R.sub.1 stands for a hydrogen atom or a methyl group, --OR.sub.2 for a dihydric alcohol residue having 1-5 carbon atoms, and m for an integer of 0-20, with an alkyleneglycol bis-allylcarbonate component represented by the formula: ##STR2## wherein --R.sub.4 stands for a hydrogen atom or a methyl group, --OR.sub.3 for a dihydric alcohol residue having 1-10 carbon atoms, and n for an integer of 1-10. In addition to the above components, there may be added a vinyl compound.Type: GrantFiled: October 19, 1992Date of Patent: August 9, 1994Assignee: NOF CorporationInventors: Toshiaki Takaoka, Katsuyoshi Tanaka, Kenji Kato
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Patent number: 5310841Abstract: A liquid composition, polymerizable by free-radical polymerization to yield organic glasses which are endowed with characteristics of low water absorption and high thermal stability, is constituted by the product of transesterification of diallyl-carbonate with a cycloaliphatic diol or a mixture of cycloaliphatic diols, from among said diols 1,4-cyclohexane-di-methanol and 3(4),8(9)-bis-(hydroxymethyl)tricyclo[5.2.1.0.sup.2.6 ]decane being preferred.Type: GrantFiled: September 26, 1990Date of Patent: May 10, 1994Assignee: Enichem Synthesis S.p.A.Inventors: Fiorenzo Renzi, Franco Rivetti, Ugo Romano
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Patent number: 5298327Abstract: A plastic light conduit of cross-linked polymer material having good light transmitting characteristics, without voids or noticeable bubbles, is disclosed. Also disclosed is a method of manufacture and an apparatus, involving progressive heating of reactive monomer mixture in a tube which is submerged in a progressive reactor utilizing cold oil to maintain a cold, non-reacting zone, and hot water to create a hot zone that causes reaction, while simultaneously carrying away the excess exothermic heat of reaction.Type: GrantFiled: January 23, 1989Date of Patent: March 29, 1994Assignee: Lumenyte International CorporationInventors: Jamshid Zarian, John A. Robbins
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Patent number: 5286816Abstract: An organic glass with improved impact strength and with a refractive index equal or similar to that of mineral glass (crown glass), is composed of the product of the radicalic polymerization of the polymerizable liquid composition obtained by the transesterification of:(A) diallyl carbonate with a mixture of polyols:(B) bis(2-hydroxyethylether) of bisphenol-A,(C) diethylene glycol, and(D) tris(hydroxyethyl) isocyanurate,where for every 100 parts b.w. of the sum of polyols (B), (C) and (D), polyol (B) is present in a quantity of from 20 to 60% b.w., polyol (C) is present in a quantity of from 20 to 60% b.w. and polyol (D) is present in a quantity of from 10 to 40% b.w.; and where the molar ratio between the diallyl carbonate and the sum of polyols (A)/(B)+(C)+(D) is equal to or higher than 3/1.Type: GrantFiled: April 20, 1993Date of Patent: February 15, 1994Assignee: Enichem Synthesis S.p.A.Inventors: Franco Rivetti, Fiorenzo Renzi, Claudio Gagliardi
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Patent number: 5276068Abstract: A polycarbonate dimethacrylate which is the condensation product of 2 parts of hydroxyalkylmethacrylate of the formula ##STR1## in which A is C.sub.1 -C.sub.6 alkylene, and 1 part of a bis(chloroformate) of the formula ##STR2## in which R is C.sub.2 -C.sub.5 alkylene having at least two carbon atoms in its principal chain and n is an integer from 1 to 4, is usable, admixed with a secondary monomer suitable for dental applications, such as BIS-GMA; PUDMA or the like, as an adhesive system for dental restorative materials. Particularly useful is the novel condensation product of 2-hydroxyethylmethacrylate and triethylene glycol bis(chloroformate).Type: GrantFiled: January 28, 1992Date of Patent: January 4, 1994Assignee: Jeneric/Pentron, Inc.Inventor: Samuel Waknine
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Patent number: 5274060Abstract: Copolymers having a molecular weight (Mw) of from 10.sup.3 to 10.sup.6, measured by gel-permeation chromatography, that are crosslinkable by acid catalysis and that consist ofa) 100-80 mol. % of structural repeating units of formulae I and II ##STR1## in a ratio of from 1:1 to 1:9 and b) 0-20 mol. % of structural repeating units of formula III ##STR2## wherein X and X' each independently of the other are ##STR3## R is hydrogen or a protecting group that can be removed by the action of acids, the radicals R.sub.1 each independently of the other are C.sub.1 -C.sub.5 alkyl, phenyl or naphthyl or together are 1,2-phenylene or --[C(R.sub.3)(R.sub.4)].sub.x -- wherein R.sub.3 and/or R.sub.4 =hydrogen or methyl and x is from 2 to 5, the radicals R.sub.2 each independently of the other are hydrogen, C.sub.1 -C.sub.5 alkyl or C.sub.1 -C.sub.5 alkoxy, R.sub.5 and R.sub.7 are each hydrogen, R.sub.6 is hydrogen, halogen or methyl and R.sub.8 is hydrogen, halogen, methyl, --CH.sub.2 halogen, --CH.sub.Type: GrantFiled: February 27, 1992Date of Patent: December 28, 1993Assignee: Ciba-Geigy CorporationInventor: Ulrich Schadeli
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Patent number: 5272230Abstract: An acrylic resin is provided which has excellent weatherability, outstanding transparency and improved heat and solvent resistance, as well as improved impact strength. The acrylic resin comprises an intimate blend of a polymerization syrup and a catalytic amount of a polymerization catalyst capable of effecting polymerization of the syrup. The polymerization syrup, which has an improved shelf life and can be stored at ambient temperature and atmospheric pressure, consists essentially of:(a) from about 300 to about 1000 parts per volume of an acrylic monomer represented by the formula ##STR1## wherein R is an alkyl moiety containing 1 to about 18 carbon atoms; (b) from about 0.1 to about 1000 parts by volume of a non-peroxide oxygen donator, such as 2,2-bis(allyloxymethyl)-butan-1-ol or diallylphthalate;(c) from about 0.5 to about 5 parts by volume of a mercaptan; and(d) from about 0.3 to about 40 parts by volume of a crosslinking agent compatible with the acrylic monomer.Type: GrantFiled: April 15, 1993Date of Patent: December 21, 1993Inventor: Bill R. Edwards
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Patent number: 5262297Abstract: Specific binding methods are used for diagnostic assays and purification separations whereby the specific binding capture reagent is prepared from copolymers having highly reactive carboxy groups. These groups are extended from the polymer surface with a linking group having from 8 to 50 atoms in the chain and two or more alkylene, arylene, alkylenearylene or arylenealkylene groups. To these reactive groups is attached a biologically active substance such as a protein or oligonucleotide which then participates in the diagnostic assays or purification separation methods.Type: GrantFiled: April 30, 1992Date of Patent: November 16, 1993Assignee: Eastman Kodak CompanyInventors: Richard C. Sutton, Susan J. Danielson, John B. Findlay, Fred. T. Oakes, Marsha D. B. Oenick, Ignazio S. Ponticello, Harold C. Warren, III
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Patent number: 5252644Abstract: An acrylic resin is provided which has excellent weatherability, outstanding transparency and improved heat and solvent resistance, as well as improved impact strength. The acrylic resin comprises an intimate blend of a polymerization syrup and a catalytic amount of a polymerization catalyst capable of effecting polymerization of the syrup. The polymerization syrup, which has an improved shelf life and can be stored at ambient temperature and atmospheric pressure, consists essentially of:(a) from about 300 to about 1000 parts per volume of an acrylic monomer represented by the formula ##STR1## wherein R is an alkyl moiety containing 1 to about 18 carbon atoms; (b) from about 0.1 to about 1000 parts by volume of a non-peroxide oxygen donator, such as 2,2-bis(allyloxymethyl)-butan-1-ol or diallylphtha1ate;(c) from about 0.5 to about 5 parts by volume of a mercaptan; and(d) from about 0.3 to about 40 parts by volume of a crosslinking agent compatible with the acrylic monomer.Type: GrantFiled: July 27, 1992Date of Patent: October 12, 1993Inventor: Bill R. Edwards
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Patent number: 5250596Abstract: An acrylic resin is provided which has excellent weatherability, outstanding transparency and improved heat and solvent resistance, as well as improved impact strength. The acrylic resin comprises an intimate blend of a polymerization syrup and a catalytic amount of a polymerization catalyst capable of effecting polymerization of the syrup. The polymerization syrup, which has an improved shelf life and can be stored at ambient temperature and atmospheric pressure, consists essentially of:(a) from about 300 to about 1000 parts per volume of an acrylic monomer represented by the formula ##STR1## wherein R is an alkyl moiety containing 1 to about 18 carbon atoms; (b) from about 0.1 to about 1000 parts by volume of a non-peroxide oxygen donator, such as 2,2-bis(allyloxymethyl)-butan-1-ol or diallylphthalate;(c) from about 0.5 to about 5 parts by volume of a mercaptan; and(d) from about 0.3 to about 40 parts by volume of a crosslinking agent compatible with the acrylic monomer.Type: GrantFiled: April 15, 1993Date of Patent: October 5, 1993Inventor: Bill R. Edwards
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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: 5243003Abstract: Acrylic/carbonate resins are provided which have excellent weatherability, outstanding transparency and improved heat and solvent resistance, as well as improved impact strength. The acrylic/carbonate resins comprise an intimate blend of a polymerization syrup and a catalytic amount of a polymerization catalyst capable of effecting polymerization of the syrup. The polymerization syrup, which has an improved shelf life and can be stored at ambient temperature and atmospheric pressure, consists essentially of:(a) from about 10 to about 990 parts per volume of an acrylic monomer represented by the formula ##STR1## wherein R is an alkyl moiety containing 1 to about 10 carbon atoms; (b) from about 990 to about 10 parts by volume diallyl diglycol carbonate monomer;(c) from about 0.1 to about 20 parts by volume of a mercaptan; and(d) from about 0.3 to about 300 parts by volume of a crosslinking agent compatible with the acrylic monomer.The polymerization syrup can further contain from about 0.Type: GrantFiled: June 25, 1992Date of Patent: September 7, 1993Inventor: Bill R. Edwards
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Patent number: 5237032Abstract: Carbonate monomers are polymerized in the presence or absence of a polymerization initiator by irradiation with electromagnetic radiation in the absence of solvent or diluent.Type: GrantFiled: September 30, 1992Date of Patent: August 17, 1993Assignees: Istituto Guido Donegani S.p.A., Enichem S.p.A.Inventors: Mark T. DeMeuse, Charles L. Ryan, Jr., Fabrizio Parodi
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Patent number: 5204430Abstract: A liquid composition comprising:(A) a monomeric, or essentially monomeric, diallyl-carbonate of a possibly halogenated diol containing aromatic groups; or a diallyl-ester of a halogenated aromatic bicarboxy acid;(B) a reactive monomer selected from diallyl orthophthalate, diallyl isophthalate, diallyl terephthalate, triallyl cyanurate and triallyl isocyanurate;(C) an oligomeric, or essentially oligomeric, diallyl-carbonate of diethylene glycolis polymerized under the action of a free-radical initiator, in order to yield optical articles having a high refractive index, low light dispersion, and with enhanced mechanical and color characteristics.Type: GrantFiled: May 14, 1991Date of Patent: April 20, 1993Assignee: Enichem Synthesis, S.p.A.Inventors: Fiorenzo Renzi, Franco Rivetti, Ugo Romano, Claudio Gagliardi, Umberto Sgambato
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Patent number: 5200483Abstract: Describes organic resin compositions of from about 30 to 90 weight percent of a polyol(allyl carbonate), e.g., diethylene glycol bis(allyl carbonate), and from about 10 to 70, e.g., 10 to 30, weight percent of a mixture of aliphatic urethanes, the terminal portions of which contain allyl or acrylyl functional groups. Polymerizable compositions prepared from such compositions produce castings which have low yellowness (b*) values and which do not pre-release from the molds in which they are formed. Polymerizates prepared from such compositions may be used to prepare photochromic articles, e.g., lenses, by incorporating a photochromic substance, e.g., by thermal transfer, into the polymerizate.Type: GrantFiled: November 7, 1991Date of Patent: April 6, 1993Assignee: PPG Industries, Inc.Inventor: Christopher D. Selvig
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Patent number: 5196492Abstract: A liquid composition which can undergo radical polymerization to produce an almost colorless and easily dyeable organic glass, containing (i) at least one poly(allyl carbonate) of a polyhydroxy alcohol having from 2 to 20 carbon atoms and from 2 to 6 hydroxy groups in the molecule, and (ii) at least one aliphatic polyol having from 2 to 5 hydroxy groups in the molecule, in quantities from 0.01 to 1% by weight on the whole composition.Type: GrantFiled: August 27, 1991Date of Patent: March 23, 1993Assignee: Enichem Synthesis S.p.A.Inventors: Fiorenzo Renzi, Claudio Gagliardi, Franco Rivetti
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Patent number: 5187207Abstract: A hydrophilic contact lens is disclsoed incorporating melanin that protects the eye from harmful radiation and superoxide.Type: GrantFiled: December 19, 1989Date of Patent: February 16, 1993Assignee: Photoprotective Technologies, Inc.Inventor: James M. Gallas
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Patent number: 5177165Abstract: A new class of polymerizable surfactants, useful for modifying the surfaces of polymeric objects, which are described by the formula:DC[A.sub.x B.sub.y ]wherein A is at least one ethylenically unsaturated hydrophilic monomer, B is at least one ethylenically unsaturated hydrophobic monomer, C is a functional chain transfer agent, D is an ethylenically unsaturated end group, y is within the range from about 0.1 to about 0.9, and x+y=1. Also disclosed are random copolymer precursors of such polymerizable surfactants.Type: GrantFiled: December 11, 1991Date of Patent: January 5, 1993Assignee: Bausch & Lomb IncorporatedInventors: Paul L. Valint, Jr., Joseph A. McGee
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Patent number: 5162411Abstract: A carbonate corresponding to formula (I) ##STR1## in which R is aromatically bound polystyrene moiety and --O--D--O-- is a diphenolate moiety in which --D-- is a divalent group containing 6 to 30 carbon atoms and r is 0 or 1 is disclosed. The carbonate is useful as a flow aid for thermoplastic molding compositions.Type: GrantFiled: July 11, 1991Date of Patent: November 10, 1992Assignee: Bayer AktiengesellschaftInventors: Gerhard Fennhoff, Uwe Westeppe, Werner Nouvertne, Karsten-Josef Idel, Edgar Leitz, Ulrich Grigo
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Patent number: 5151480Abstract: The invention relates to a process for the production of mouldings of crosslinked polymers by processing (moulding) of uncrosslinked copolymers of vinyl compounds and polymerisable silane compounds having 1 to 3 hydrolysable groups to give the desired mouldings and crosslinking of the copolymers in the mouldings by aftertreatment of the mouldings with acidic or alkaline aqueous solutions.Type: GrantFiled: June 3, 1991Date of Patent: September 29, 1992Assignee: Bayer AktiengesellschaftInventors: Wolfgang Podszun, Michael Muller, Wilfried Cramer, Bodo Rehbold
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Patent number: 5147777Abstract: Biologically active reagents are prepared from particles of copolymers having highly reactive carboxy or equivalent groups. The reagents are prepared by covalently attaching biologically active substances, for example antibodies, to the particles, directly or indirectly through highly reactive carboxy groups on the particle surface. These reagents are used to advantage in analytical elements, methods for the detection of specific binding ligands (such as immunological species) and immunoassays, and in purification methods as affinity chromatography reagents.Type: GrantFiled: June 18, 1990Date of Patent: September 15, 1992Assignee: Eastman Kodak CompanyInventors: Richard C. Sutton, Susan J. Danielson, John B. Findlay, Fred T. Oakes, Marsha D. B. Oenick, Ignazio S. Ponticello, Harold C. Warren, III
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Patent number: 5134210Abstract: An acrylic resin is provided which has excellent weatherability, outstanding transparency and improved heat and solvent resistance, as well as improved impact strength. The acrylic resin comprises an intimate blend of a polymerization syrup and a catalytic amount of a polymerization catalyst capable of effecting polymerization of the syrup. The polymerization syrup, which has an improved shelf life and can be stored at ambient temperature and atmospheric pressure, consists essentially of:(a) from about 300 to about 1000 parts per volume of an acrylic monomer represented by the formula ##STR1## wherein R is an alkyl moiety containing 1 to about 18 carbon atoms; (b) from about 0.1 to about 1000 parts by volume of a non-peroxide oxygen donator;(c) from about 0.1 to about 5 parts by volume of mercaptan; and(d) from about 0.3 to about 40 parts by volume of a crosslinking agent compatible with the acrylic monomer.Type: GrantFiled: June 24, 1991Date of Patent: July 28, 1992Inventor: Bill R. Edwards
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Patent number: 5130393Abstract: The plastic lens of the present invention consists of a copolymer obtained by copolymerizing a monomer mixture consisting of given proportions of diethylene glycol bis(allyl carbonate), benzyl methacrylate, diallyl phthalate (these three monomers has been used as a monomer mixture for conventional plastic lenses) and, as an additional monomer, an alkyl methacrylate. This copolymer has excellent adhesion to upper and lower molds and, when immersed in, for example, a cleaning solution such as a methylene chloride-strong alkali mixed cleaning solution or the like, causes no separation from the molds; accordingly in the copolymer, there can be prevented the occurrence of surface roughening, cloudiness and striae which have been problems in conventional plastic lenses.Type: GrantFiled: November 8, 1989Date of Patent: July 14, 1992Assignee: Hoya CorporationInventor: Shigeo Nakamura
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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: 5112883Abstract: The present invention is directed to a medium incorporating melanin for radiation protection.Type: GrantFiled: November 9, 1990Date of Patent: May 12, 1992Assignee: Photoprotective Technologies IncorporatedInventor: James M. Gallas
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Patent number: 5110881Abstract: A photochromic article having improved pohotochromic equilibrium response is described. In particular, a phtochromic compound is incorporation into or applied to an article, e.g., matrix, of a synthetic organic resin prepared from a composition comprising from about 55 to about 90 weight percent of a polyol(allyl carbonate), e.g., diethylene glycol bis(allyl carbonate), from about 10 to about 40 weight percent of an aliphatic polyurethane having terminal ethylenic unsaturation, e.g., an aliphatic polyesterurethane diacrylate, and from about 0 to about 5 weight percent of a difunctional monomer selected from the group consisting of allyl methacrylate and allyl acrylate. Such photochromic articles have an improved photochromic equilibrium response at ambient temperatures compared to the response of a comparable photochromic article prepared from a polyol(allyl carbonate) homopolymer, e.g., homopolymers of diethylene glycol bis(allyl carbonate), at the same ambient temperatures.Type: GrantFiled: January 10, 1991Date of Patent: May 5, 1992Assignee: PPG Industries, Inc.Inventors: Douglas S. McBain, John C. Crano
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Patent number: 5100987Abstract: Monethylenically 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 -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: October 25, 1990Date of Patent: March 31, 1992Assignee: Ciba-Geigy CorporationInventors: Kevin B. Hatton, Edward Irving, Josephine M. A. Walshe, Anne Mallaband
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Patent number: 5095079Abstract: To produce a graded index polymer there is diffused into a base material formed of at least one partly polymerized monomer adapted to yield a homopolymer with refractive index N1 in the gel state an additive material formed of at least one monomer adapted to yield a homopolymer with refractive index N2 different from N1. The polymerization of the base material treated in this way is then completed. The additive material comprises a mixture of at least two monomers and the composition of this mixture is varied with time.Type: GrantFiled: June 26, 1990Date of Patent: March 10, 1992Assignee: Essilor International Cie Generale d'OptiqueInventors: Leanirith Yean, Georges Wajs, Gerard Martin, Patrick Guerrero
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Patent number: 5073587Abstract: An acrylic-based particulate filled polymeric composition is provided which is curable at atmospheric pressure and ambient temperature and has a pour to pull time of less than about 4 hours. The acrylic-based particulate filled polymeric composition comprises an intimate blend of a polymerization syrup, a filler, and minor effective amount of crosslinking agent, a polymerization catalyst, a quaternary compound and a polymerization initiator. To enhance and reduce the pour to pull time of articles molded or cast from the acrylic-based particular filled polymeric composition, an effective miner amount of a reaction modifier, such as trimethylpropane triacrylate, can be incorporated into the polymeric composition. The polymerization syrup employed in formulating an acrylic-based particulate filled polymeric composition consist essentially of from about 300 to about 1,000 parts by volume of an acrylic monomer, from about 0.01 to about 1 part by volume of peroxide-free oxygen donator, from about 0.Type: GrantFiled: January 16, 1990Date of Patent: December 17, 1991Inventor: Bill R. Edwards
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Patent number: 5059663Abstract: A liquid composition stable during storage and polymerizable radically into organic glasses having a high refractive index, containing:(A) from 20 to 80% wt of a mixture of monomer and oligomers of a carbonic allyl derivative representable by the formula (I): ##STR1## where: X=halogen (except fluorine);a and be independently assume the values 1 or 2;n assumes values from 1 to 5 on condition that at least 10% by weight of the mixture consists of carbonic allyl oligomer derivatives (n>1); and(B) from 80 to 20% by weight of a liquid monomer copolymerizable with the component (A) and chosen from diallyl isophthalate, diallyl terephthalate, triallyl cyanurate and triallyl isocyanurate.Type: GrantFiled: August 2, 1990Date of Patent: October 22, 1991Assignee: Enichem Synthesis S.p.A.Inventors: Franco Rivetti, Fiorenzo Renzi
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Patent number: 5047447Abstract: The present invention is directed to a medium incorporating melanin for radiation protection.Type: GrantFiled: December 20, 1989Date of Patent: September 10, 1991Assignee: Photoprotecive Technologies IncorporatedInventor: James M. Gallas
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Patent number: 5045395Abstract: Crosslinked bead polymers having an average particle diameter in the range of from 0.5-10 .mu.m and a narrow particle size distribution can be prepared by polymerization of vinyl monomers and silane monomer units which contain a hydrolysable group, the polymerization being carried out in a non-aqueous, polar medium using a free-radical former as the initiator in the presence of a polymer which is soluble in this medium and acts as a dispersant, and furthermore in the presence of a low molecular weight surfactant, and the resulting polymer is then crosslinked by the action of an aqueous acid or base.Type: GrantFiled: August 15, 1990Date of Patent: September 3, 1991Assignee: Bayer AktiengesellschaftInventor: Wolfgang Podszun
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Patent number: 5045613Abstract: An acrylic resin is provided which has excellent weatherability, outstanding transparency and improved heat and solvent resistance, as well as improved impact strength. The acrylic resin comprises an intimate blend of a polymerization syrup and a catalytic amount of a polymerization catalyst capable of effecting polymerization of the syrup. The polymerization syrup, which has an improved shelf life and can be stored at ambient temperature and atmospheric pressure, consists essentially of:(a) from about 300 to about 1000 parts per volume of an acrylic monomer represented by the formula ##STR1## wherein R is an alkyl moiety containing 1 to about 18 carbon atoms; (b) from about 0.1 to about 1 part by volume of diallylphthalate;(c) from about 0.5 to about 5 parts by volume of mercaptan; and(d) from about 0.3 to about 40 parts by volume of a crosslinking agent compatible with the acrylic monomer.The polymerization syrup can further contain from about 1 to about 100 parts by volume of a polycarbonate compound.Type: GrantFiled: August 15, 1990Date of Patent: September 3, 1991Inventor: Bill R. Edwards
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Patent number: 5036115Abstract: Melanin is used as the absorbing pigment for radiation protective eyeware. Thus, a melanin-plastic copolymer was formed by adding a catalyst (benzoyl peroxide) to the liquid monomer, diethylene glycol bis allyl carbonate (CR-39), which contained dissolved catechol (a melanin precursor); the solution was heated for one day at 50 degrees celsius and an additional two days at 65 degrees celsius and yielded an optically transparent solid plastic with amber color and with an optical absorption spectrum very close to that associated with melanin.Type: GrantFiled: March 19, 1990Date of Patent: July 30, 1991Assignee: Photoprotective Technologies, Inc.Inventor: James M. Gallas
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Patent number: 5023313Abstract: An acrylic resin is provided which has excellent weatherability, outstanding transparency and improved heat and solvent resistance, as well as improved impact strength. The acrylic resin comprises an intimate blend of a polymerization syrup and a catalytic amount of a polymerization catalyst capable of effecting polymerization of the syrup. The polymerization syrup, which has an improved shelf life and can be stored at ambient temperature and atmospheric pressure, consists essentially of:(a) from about 300 to about 1000 parts per volume of an acrylic monomer represented by the formula ##STR1## wherein R is an alkyl moiety containing 1 to about 18 carbon atoms; (b) from about 0.1 to about 1 parts by volume of 2,2-bis(allyl-oxymethyl)-butan-1-ol;(c) from about 0.5 to about 5 parts by volume of a mercaptan; and(d) from about 0.3 to about 40 parts by volume of a crosslinking agent compatible with the acrylic monomer.Type: GrantFiled: May 23, 1990Date of Patent: June 11, 1991Inventor: Bill R. Edwards
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Patent number: 5017666Abstract: Polyol (allyl carbonate), e.g., diethylene glycol bis(allyl carbonate), are polymerized in solution, i.e., in an organic solvent, until from about 20 to 50 percent of the allylic carbon-carbon linkages are consumed. The solvent is then removed yielding a product that is a gel-free, syrupy viscous liquid of unpolymerized monomer and polymer. This liquid polymer can be polymerized to a hard, transparent material with less shrinkage. Also described is the addition of mono- or polyfunctional acrylates to the liquid polymer to product a polymerizable mixture that can be cured quickly with the addition of a free-radical initiator.Type: GrantFiled: February 26, 1988Date of Patent: May 21, 1991Assignee: PPG Industries, Inc.Inventors: John C. Crano, Ronald L. Haynes
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Patent number: 4994208Abstract: A photochromic article having improved photochromic equilibrium response is described. In particular, a photochromic compound is incorporated into or applied to an article, e.g., matrix, of a synthetic organic resin prepared from a composition comprising from about 55 to about 90 weight percent of a polyol(allyl carbonate), e.g., diethylene glycol bis(allyl carbonate), from about 10 to about 40 weight percent of an aliphatic polyurethan having terminal ethylenic unsaturation, e.g., an aliphatic polyesterurethan diacrylate, and from about 0 to about 5 weight percent of a difunctional monomer selected from the group consisting of allyl methacrylate and allyl acrylate. Such photochromic articles have an improved photochromic equilibrium response at ambient temperatures compared to the response of a comparable photochromic article prepared from a polyol(allyl carbonate) homopolymer, e.g., homopolymers of diethylene glycol bis(allyl carbonate), at the same ambient temperatures.Type: GrantFiled: April 18, 1989Date of Patent: February 19, 1991Assignee: PPG Industries, Inc.Inventors: Douglas S. McBain, John C. Crano
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Patent number: 4994537Abstract: Acrylate copolymers comprising (a) repeating units derived from at least one acrylic or methacrylic ester and, by weight of the total copolymer, (b) about 0.1 to 3% of repeating units derived from at least one water-soluble monomer possessing conjugated unsaturation and (c) about 0.1 to 3% of repeating units derived from at least one water-soluble allyl monomer; aqueous polyacrylate dispersions comprising such polymers; and a process of preparing the same. Optionally, the copolymers contain other free-radical polymerizable monomers.Type: GrantFiled: September 18, 1989Date of Patent: February 19, 1991Assignee: Hercules IncorporatedInventors: Daniel H. Craig, Harry J. Goldy
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Patent number: 4973639Abstract: In one embodiment this invention provides a novel polymerizable quaternary ammonium carbonate corresponding to the formula: ##STR1## In another embodiment this invention provides a novel copolymer of the above represented methacrylamidopropyltrimethylammonium methyl carbonate and acrylamide, which exhibits a high level clay flocculation efficiency.Type: GrantFiled: October 25, 1989Date of Patent: November 27, 1990Assignee: Hoechst Celanese CorporationInventors: Thomas C. Shen, James H. Rea
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Patent number: 4962163Abstract: Thermosettable vinyl ester compositions are prepared from an advanced epoxy resin containing a mesogenic or rodlike moiety and a monounsaturated monocarboxylic acid and, optionally, a monoepoxide compound. These vinyl ester compounds can be mixed with polymerizable ethylenically unsaturated monomers which can, if desired, contain a mesogenic or rigid rodlike moiety.Type: GrantFiled: January 17, 1989Date of Patent: October 9, 1990Assignee: The Dow Chemical CompanyInventors: Robert E. Hefner, Jr., Jimmy D. Earls, Paul M. Puckett
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Patent number: 4959433Abstract: Polymerizable, liquid, substantially gel-free, partially polymerized monomer compositions having allylic utilizations greater than 50 percent can be prepared if the monomer which has been partially polymerized is bis(allylic carbonate) monomer of at least one 4,4'-(alkylidene)-bis[phenol], bis(allylic carbonate) monomer of at least one 4,4'-[phenylenebis(alkylidene)]bis [phenol], or a mixture thereof.Type: GrantFiled: March 12, 1987Date of Patent: September 25, 1990Assignee: PPG Industries, Inc.Inventors: Stephanie J. Oates, Edward J. Sare
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Patent number: 4959429Abstract: The yellowness of polymerizates formed form polymerizable compositions containing bisphenol bis(allylic carbonate)-functional material is reduced by inclusion of one or more cyclohexenic compounds in the polymerizable compositions.Type: GrantFiled: May 19, 1988Date of Patent: September 25, 1990Assignee: PPG Industries, Inc.Inventors: Michael S. Misura, Edward J. Sare
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Patent number: 4954591Abstract: Polymerizable and cross-linkable, radiation curable coating compositions particularly designed for deposition as an abrasion resistant, tintable coating poly (bis phenyl A) carbonates. The formulation is a mixture including:(a) 25-94% by weight of a polyfunctional acrylate or methacrylate monomer having at least three acrylate functional groups per molecule or a mixture of such monomers;(b) 3-50% by weight of a monomer selected from N-vinyl derivatives of linear or cyclic secondary amides, tetrahydrofurfuryl acrylate or methacrylate, N,N-di(lower alkyl) acrylamide ethylenically unsaturated monosilane, or a mixture of such monomers; and(c) 3-40% by weight of an ethylenically unsaturated monomer having a Tg less than 80.degree. C. or 3-30% of an ethylenically unsaturated copolymer with a Tg less than 100.degree. C.Type: GrantFiled: November 6, 1987Date of Patent: September 4, 1990Assignee: Pilkington Visioncare Holdings, Inc.Inventor: Hector Belmares
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Patent number: 4948854Abstract: A transparent optical article is constituted of an optical resin. The optical resin in obtained by polymerizing a feed monomer containing at least a diester of unsaturated dicarboxylic acid selected from the group consisting of itaconic acid, citraconic acid and mesaconic acid. The ester group forming the diester is ##STR1## or R, wherein X represents a halogen atom, m represents zero or an integer of 1 to 5 and R represents an alkyl group having 1 to 12 carbon atoms, an alkenyl group having 1 to 12 carbon atoms or a cycloalkyl group having 3 to 12 carbon atoms. At least one of the ester groups has an aromatic ring defined above.Type: GrantFiled: October 3, 1989Date of Patent: August 14, 1990Inventors: Naoyuki Amaya, Keizo Anan, Yoshishige Murata, Takao Mogami, Yoshio Sano, Haruhiro Ikebe, Rumiko Seita
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Patent number: 4945122Abstract: An acrylic resin is provided which has excellent weatherability, outstanding transparency and improved heat and solvent resistance, as well as improved impact strength. The acrylic resin comprises an intimate blend of a polymerization syrup and a catalytic amount of a polymerization catalyst capable of effecting polymerization of the syrup. The polymerization syrup, which has an improved shelf life and can be stored at ambient temperature and atmospheric pressure, consists essentially of:(a) from about 300 to about 1000 parts per volume of an acrylic monomer represented by the formula ##STR1## wherein R is an alkyl moiety containing 1 to about 18 carbon atoms; (b) from about 0.1 to about 1 parts by volume of 2,2-bis(allyl-oxymethyl)-butan-1-ol;(c) from about 0.5 to about 5 parts by volume of a mercaptan; and(d) from about 0.3 to about 40 parts by volume of a crosslinking agent compatible with the acrylic monomer.Type: GrantFiled: July 27, 1989Date of Patent: July 31, 1990Inventor: Bill R. Edwards
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Patent number: 4930879Abstract: A Synthetic resin lens having a surface hard coating comprises a synthetic resin lens body and a surface hard coat deposited on the lens body. The synthetic resin lens body is made of a resin obtained by copolymerizing monomers consisting essentially as synthetic resinous components of 10 to 80 percent by weight of at least one diester of itaconic acid and mesaconic acid, 10 to 80 percent by weight of at least one allyl compound and 5 to 50 percent by weight of diethyleneglycol bis(allylcarbonate). The surface hard coat is formed by curing a coating composition comprising 50 to 800 parts by weight of at least one organic silicon compound, 100 parts by weight of colloidal silica, 50 to 600 parts by weight of a polyfunctional compound such as a polyfunctional epoxy compound, a polyalcohol, a polycarboxylic acid, or a polycarboxylic anhydride and 0.01 to 5.0 percent by weight of a curing catalyst based on the residual solids in the composition after curing.Type: GrantFiled: September 26, 1988Date of Patent: June 5, 1990Assignees: Nippon Oil and Fats Co., Ltd., Seiko Epson Corp.Inventors: Takeaki Iryo, Satoshi Kubota, Yoshio Sano, Yoshishige Murata, Yasumi Koinuma
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Patent number: 4879318Abstract: A method for making a plastic lens and a plastic lens made thereby. The method comprises disposing a liquid monomer or a monomer mixture and a photosensitive initiator into a mold cavity and directing ultraviolet light to act on the lens forming material in the cavity to produce a lens therefrom. The liquid monomer mixture may include one or more of diethylene glycol bis(allyl)-carbonate, bisphenol A diallyl carbonate, 1,6 hexanedioldimethacrylate, trimethylol propane triacrylate, tetraethylene glycol diacrylate, tripropylene glycol diacrylate, tetrahydrofurfurylmethacrylate, tetrahydrofurfuryl acrylate and styrene. The photosensitive initiator may be selected from the group of 2-hydroxy-2-methyl-1- phenyl-propan-1-one and 1-hydroxycyclohexyl phenyl ketone.Type: GrantFiled: November 18, 1988Date of Patent: November 7, 1989Assignee: Ophthalmic Research Group International, Inc.Inventors: N. Thornton Lipscomb, Omar M. Buazza
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Patent number: 4879363Abstract: Novel organic glass comprising a copolymer of (a) a diallyl phthalate monomer, (b) an allyl benzoate monomer and (c) a glycol bis(allylcarbonate) monomer, which has a high refractive index and excellent other physical properties such as high impact resistance, high dimension stability, excellent mechanical processing properties, excellent dyeability, excellent hard coating property, and is useful as a material for optical parts such as lenses and prisms.Type: GrantFiled: October 12, 1988Date of Patent: November 7, 1989Assignee: Daiso Co., Ltd.Inventors: Yoshiharu Fujio, Kanemasa Matsukuma, Toshihiko Nishimoto
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Patent number: 4855374Abstract: According to the invention, there are provided an optical resin and a process for preparing such a resin. The optical resin is obtained by polymerizing a feed monomer comprising at least a diester of dicarboxylic acid represented by the general formula (1) of: ##STR1## wherein R.sub.1 and R.sub.2 each represent the same or different groups and stand for an alkyl or alkenyl group having 1 to 12 carbon atoms, a cycloalkyl group having 3 to 12 carbon atoms or an ester residue having at least one aromatic ring.Type: GrantFiled: June 22, 1988Date of Patent: August 8, 1989Assignee: Nippon Oil and Fats Co., Ltd.Inventors: Yoshishige Murata, Yasumi Koinuma, Naoyuki Amaya, Takayuki Otsu, Masafumi Nisimura
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Patent number: 4835233Abstract: A liquid, fluid composition, comprising:(a) bis(allylcarbonate) of monomer diethylene glycol;(b) bis(allylcarbonate) of oligomer diethylene glycol;(c) tris(allylcarbonate) of monomer tris(hydroxyethyl)isocyanurate;(d) a monofunctional, unsaturated vinyl or methacryl ester monomer,is polymerized inside a mould (casting process), with fast polymerization cycle, to yield optical articles.Type: GrantFiled: August 25, 1988Date of Patent: May 30, 1989Assignee: Enichem Sintesi S.P.A.Inventors: Fiorenzo Renzi, Franco Rivetti, Ugo Romano