From Monomer Containing A Carbonate Group, I.e., -o-c(=o)-o- Patents (Class 526/314)
  • Patent number: 5336743
    Abstract: 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: Grant
    Filed: October 19, 1992
    Date of Patent: August 9, 1994
    Assignee: NOF Corporation
    Inventors: Toshiaki Takaoka, Katsuyoshi Tanaka, Kenji Kato
  • Patent number: 5310841
    Abstract: 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: Grant
    Filed: September 26, 1990
    Date of Patent: May 10, 1994
    Assignee: Enichem Synthesis S.p.A.
    Inventors: Fiorenzo Renzi, Franco Rivetti, Ugo Romano
  • Patent number: 5298327
    Abstract: 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: Grant
    Filed: January 23, 1989
    Date of Patent: March 29, 1994
    Assignee: Lumenyte International Corporation
    Inventors: Jamshid Zarian, John A. Robbins
  • Patent number: 5286816
    Abstract: 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: Grant
    Filed: April 20, 1993
    Date of Patent: February 15, 1994
    Assignee: Enichem Synthesis S.p.A.
    Inventors: Franco Rivetti, Fiorenzo Renzi, Claudio Gagliardi
  • Patent number: 5276068
    Abstract: 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: Grant
    Filed: January 28, 1992
    Date of Patent: January 4, 1994
    Assignee: Jeneric/Pentron, Inc.
    Inventor: Samuel Waknine
  • Patent number: 5274060
    Abstract: 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: Grant
    Filed: February 27, 1992
    Date of Patent: December 28, 1993
    Assignee: Ciba-Geigy Corporation
    Inventor: Ulrich Schadeli
  • Patent number: 5272230
    Abstract: 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: Grant
    Filed: April 15, 1993
    Date of Patent: December 21, 1993
    Inventor: Bill R. Edwards
  • Patent number: 5262297
    Abstract: 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: Grant
    Filed: April 30, 1992
    Date of Patent: November 16, 1993
    Assignee: Eastman Kodak Company
    Inventors: Richard C. Sutton, Susan J. Danielson, John B. Findlay, Fred. T. Oakes, Marsha D. B. Oenick, Ignazio S. Ponticello, Harold C. Warren, III
  • Patent number: 5252644
    Abstract: 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: Grant
    Filed: July 27, 1992
    Date of Patent: October 12, 1993
    Inventor: Bill R. Edwards
  • Patent number: 5250596
    Abstract: 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: Grant
    Filed: April 15, 1993
    Date of Patent: October 5, 1993
    Inventor: Bill R. Edwards
  • Patent number: 5248805
    Abstract: 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: Grant
    Filed: March 2, 1992
    Date of Patent: September 28, 1993
    Assignee: BASF Aktiengesellschaft
    Inventors: Andreas Boettcher, Gerd Rehmer
  • Patent number: 5243003
    Abstract: 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: Grant
    Filed: June 25, 1992
    Date of Patent: September 7, 1993
    Inventor: Bill R. Edwards
  • Patent number: 5237032
    Abstract: 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: Grant
    Filed: September 30, 1992
    Date of Patent: August 17, 1993
    Assignees: Istituto Guido Donegani S.p.A., Enichem S.p.A.
    Inventors: Mark T. DeMeuse, Charles L. Ryan, Jr., Fabrizio Parodi
  • Patent number: 5204430
    Abstract: 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: Grant
    Filed: May 14, 1991
    Date of Patent: April 20, 1993
    Assignee: Enichem Synthesis, S.p.A.
    Inventors: Fiorenzo Renzi, Franco Rivetti, Ugo Romano, Claudio Gagliardi, Umberto Sgambato
  • Patent number: 5200483
    Abstract: 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: Grant
    Filed: November 7, 1991
    Date of Patent: April 6, 1993
    Assignee: PPG Industries, Inc.
    Inventor: Christopher D. Selvig
  • Patent number: 5196492
    Abstract: 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: Grant
    Filed: August 27, 1991
    Date of Patent: March 23, 1993
    Assignee: Enichem Synthesis S.p.A.
    Inventors: Fiorenzo Renzi, Claudio Gagliardi, Franco Rivetti
  • Patent number: 5187207
    Abstract: A hydrophilic contact lens is disclsoed incorporating melanin that protects the eye from harmful radiation and superoxide.
    Type: Grant
    Filed: December 19, 1989
    Date of Patent: February 16, 1993
    Assignee: Photoprotective Technologies, Inc.
    Inventor: James M. Gallas
  • Patent number: 5177165
    Abstract: 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: Grant
    Filed: December 11, 1991
    Date of Patent: January 5, 1993
    Assignee: Bausch & Lomb Incorporated
    Inventors: Paul L. Valint, Jr., Joseph A. McGee
  • Patent number: 5162411
    Abstract: 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: Grant
    Filed: July 11, 1991
    Date of Patent: November 10, 1992
    Assignee: Bayer Aktiengesellschaft
    Inventors: Gerhard Fennhoff, Uwe Westeppe, Werner Nouvertne, Karsten-Josef Idel, Edgar Leitz, Ulrich Grigo
  • Patent number: 5151480
    Abstract: 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: Grant
    Filed: June 3, 1991
    Date of Patent: September 29, 1992
    Assignee: Bayer Aktiengesellschaft
    Inventors: Wolfgang Podszun, Michael Muller, Wilfried Cramer, Bodo Rehbold
  • Patent number: 5147777
    Abstract: 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: Grant
    Filed: June 18, 1990
    Date of Patent: September 15, 1992
    Assignee: Eastman Kodak Company
    Inventors: Richard C. Sutton, Susan J. Danielson, John B. Findlay, Fred T. Oakes, Marsha D. B. Oenick, Ignazio S. Ponticello, Harold C. Warren, III
  • Patent number: 5134210
    Abstract: 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: Grant
    Filed: June 24, 1991
    Date of Patent: July 28, 1992
    Inventor: Bill R. Edwards
  • Patent number: 5130393
    Abstract: 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: Grant
    Filed: November 8, 1989
    Date of Patent: July 14, 1992
    Assignee: Hoya Corporation
    Inventor: Shigeo Nakamura
  • Patent number: 5128386
    Abstract: 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: Grant
    Filed: December 15, 1989
    Date of Patent: July 7, 1992
    Assignee: BASF Aktiengesellschaft
    Inventors: Gerd Rehmer, Andreas Boettchher, Gerhard Auchter
  • Patent number: 5112883
    Abstract: The present invention is directed to a medium incorporating melanin for radiation protection.
    Type: Grant
    Filed: November 9, 1990
    Date of Patent: May 12, 1992
    Assignee: Photoprotective Technologies Incorporated
    Inventor: James M. Gallas
  • Patent number: 5110881
    Abstract: 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: Grant
    Filed: January 10, 1991
    Date of Patent: May 5, 1992
    Assignee: PPG Industries, Inc.
    Inventors: Douglas S. McBain, John C. Crano
  • Patent number: 5100987
    Abstract: 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: Grant
    Filed: October 25, 1990
    Date of Patent: March 31, 1992
    Assignee: Ciba-Geigy Corporation
    Inventors: Kevin B. Hatton, Edward Irving, Josephine M. A. Walshe, Anne Mallaband
  • Patent number: 5095079
    Abstract: 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: Grant
    Filed: June 26, 1990
    Date of Patent: March 10, 1992
    Assignee: Essilor International Cie Generale d'Optique
    Inventors: Leanirith Yean, Georges Wajs, Gerard Martin, Patrick Guerrero
  • Patent number: 5073587
    Abstract: 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: Grant
    Filed: January 16, 1990
    Date of Patent: December 17, 1991
    Inventor: Bill R. Edwards
  • Patent number: 5059663
    Abstract: 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: Grant
    Filed: August 2, 1990
    Date of Patent: October 22, 1991
    Assignee: Enichem Synthesis S.p.A.
    Inventors: Franco Rivetti, Fiorenzo Renzi
  • Patent number: 5047447
    Abstract: The present invention is directed to a medium incorporating melanin for radiation protection.
    Type: Grant
    Filed: December 20, 1989
    Date of Patent: September 10, 1991
    Assignee: Photoprotecive Technologies Incorporated
    Inventor: James M. Gallas
  • Patent number: 5045395
    Abstract: 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: Grant
    Filed: August 15, 1990
    Date of Patent: September 3, 1991
    Assignee: Bayer Aktiengesellschaft
    Inventor: Wolfgang Podszun
  • Patent number: 5045613
    Abstract: 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: Grant
    Filed: August 15, 1990
    Date of Patent: September 3, 1991
    Inventor: Bill R. Edwards
  • Patent number: 5036115
    Abstract: 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: Grant
    Filed: March 19, 1990
    Date of Patent: July 30, 1991
    Assignee: Photoprotective Technologies, Inc.
    Inventor: James M. Gallas
  • Patent number: 5023313
    Abstract: 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: Grant
    Filed: May 23, 1990
    Date of Patent: June 11, 1991
    Inventor: Bill R. Edwards
  • Patent number: 5017666
    Abstract: 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: Grant
    Filed: February 26, 1988
    Date of Patent: May 21, 1991
    Assignee: PPG Industries, Inc.
    Inventors: John C. Crano, Ronald L. Haynes
  • Patent number: 4994208
    Abstract: 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: Grant
    Filed: April 18, 1989
    Date of Patent: February 19, 1991
    Assignee: PPG Industries, Inc.
    Inventors: Douglas S. McBain, John C. Crano
  • Patent number: 4994537
    Abstract: 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: Grant
    Filed: September 18, 1989
    Date of Patent: February 19, 1991
    Assignee: Hercules Incorporated
    Inventors: Daniel H. Craig, Harry J. Goldy
  • Patent number: 4973639
    Abstract: 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: Grant
    Filed: October 25, 1989
    Date of Patent: November 27, 1990
    Assignee: Hoechst Celanese Corporation
    Inventors: Thomas C. Shen, James H. Rea
  • Patent number: 4962163
    Abstract: 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: Grant
    Filed: January 17, 1989
    Date of Patent: October 9, 1990
    Assignee: The Dow Chemical Company
    Inventors: Robert E. Hefner, Jr., Jimmy D. Earls, Paul M. Puckett
  • Patent number: 4959433
    Abstract: 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: Grant
    Filed: March 12, 1987
    Date of Patent: September 25, 1990
    Assignee: PPG Industries, Inc.
    Inventors: Stephanie J. Oates, Edward J. Sare
  • Patent number: 4959429
    Abstract: 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: Grant
    Filed: May 19, 1988
    Date of Patent: September 25, 1990
    Assignee: PPG Industries, Inc.
    Inventors: Michael S. Misura, Edward J. Sare
  • Patent number: 4954591
    Abstract: 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: Grant
    Filed: November 6, 1987
    Date of Patent: September 4, 1990
    Assignee: Pilkington Visioncare Holdings, Inc.
    Inventor: Hector Belmares
  • Patent number: 4948854
    Abstract: 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: Grant
    Filed: October 3, 1989
    Date of Patent: August 14, 1990
    Inventors: Naoyuki Amaya, Keizo Anan, Yoshishige Murata, Takao Mogami, Yoshio Sano, Haruhiro Ikebe, Rumiko Seita
  • Patent number: 4945122
    Abstract: 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: Grant
    Filed: July 27, 1989
    Date of Patent: July 31, 1990
    Inventor: Bill R. Edwards
  • Patent number: 4930879
    Abstract: 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: Grant
    Filed: September 26, 1988
    Date of Patent: June 5, 1990
    Assignees: Nippon Oil and Fats Co., Ltd., Seiko Epson Corp.
    Inventors: Takeaki Iryo, Satoshi Kubota, Yoshio Sano, Yoshishige Murata, Yasumi Koinuma
  • Patent number: 4879318
    Abstract: 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: Grant
    Filed: November 18, 1988
    Date of Patent: November 7, 1989
    Assignee: Ophthalmic Research Group International, Inc.
    Inventors: N. Thornton Lipscomb, Omar M. Buazza
  • Patent number: 4879363
    Abstract: 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: Grant
    Filed: October 12, 1988
    Date of Patent: November 7, 1989
    Assignee: Daiso Co., Ltd.
    Inventors: Yoshiharu Fujio, Kanemasa Matsukuma, Toshihiko Nishimoto
  • Patent number: 4855374
    Abstract: 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: Grant
    Filed: June 22, 1988
    Date of Patent: August 8, 1989
    Assignee: Nippon Oil and Fats Co., Ltd.
    Inventors: Yoshishige Murata, Yasumi Koinuma, Naoyuki Amaya, Takayuki Otsu, Masafumi Nisimura
  • Patent number: 4835233
    Abstract: 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: Grant
    Filed: August 25, 1988
    Date of Patent: May 30, 1989
    Assignee: Enichem Sintesi S.P.A.
    Inventors: Fiorenzo Renzi, Franco Rivetti, Ugo Romano