Ppg Industries, Inc.

Ppg Industries Ohio, Inc.

John C Crano

Ronald L Haynes

Charles R Wiedrich

Douglas S McBain

Rodney J Hurditch

Patricia L Kwiatkowski

Robert H Tang

Robert A Smith

Randy E Daughenbaugh

Robert D Herold

Michael O Okoroafor

Dennis K Krass

Carol L Knox

Christopher D Selvig

Norman R DeLue

Rifat Tabakovic

Melvin S Newman

Described are photochromic organic resin compositions and the impact resistant polymerizates and coating compositions made therefrom. The organic resin composition comprises the reaction product of at least one polyol having greater than 1.0 hydroxyl groups; at least one polyisocyanate having greater than 1.0 isocyanato groups; and at least one polyamine curing agent having greater than 1.0 amino groups. The polymerizates are made photochromic either by the addition of organic photochromic compounds to the reactants used to form the polymerizate or by methods that imbibe or transfer the photochromic compounds into the polymerizate. Optically clear photochromic and impact resistant articles such as ophthalmic lenses and articles having photochromic coatings prepared from the photochromic organic resin compositions are also described.

Photochromic organic resin composition

Describes polymerizable organic compositions of a major amount of a first monomer component which is a polyol(allyl carbonate), e.g., diethylene glycol bis(allyl carbonate), and from about 2 to 35 weight percent of a second monomer component which is an alkoxylated bisphenol (or hydrogenated bisphenol) having acrylate or methacrylate groups, e.g., dimethacrylate of bisphenol A having 25 to 35 ethoxy units. Substantially completely cured 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.

Polymerizable polyol (allyl carbonate) composition

Describes polymerizable organic resin compositions of from about 70 to 90 weight percent of a polyol(allyl carbonate), e.g., diethylene glycol bis(allyl carbonate), and from about 30 to 70 weight percent of aliphatic polyurethane having terminal allylic unsaturation. The polymerizable compositions have initiated pot life times of at least about 24 hours at 25.degree. C. and castings that have low yellowness (b*) values. 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.

Resin composition of polyol (allyl carbonate) and allyl terminated

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.

Polymerizable organic resin composition

Polyol(allyl carbonate) compositions and polymerizates thereof that have an enhanced resistance to yellowing on exposure to external heating are described. In particular, a polyol(allyl carbonate) composition comprising (a) 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 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 and (b) from about 0.01 to about 0.5 weight percent of a dialkyl pyrocarbonate, e.g., diethyl pyrocarbonate, based on the weight of the polymerizable reactants is described. Polymerizates of such polyol(allyl carbonate) compositions have an enhanced resistance to yellowing when heated at elevated temperatures, e.g., 130.degree. C.

Polyol(allyl carbonate) composition

Variable-transmittance articles, such as an ophthalmic lens, are prepared by applying to or incorporating within the article a combination of two (or more) organic photochromic substances exhibiting different activated absorption maxima within the matrix in which the substances are incorporated. One organic photochromic substance has an absorption maximum within the range of between greater than 590 and about 700 nanometers. The other organic photochromic substance exhibits at least one absorption maximum and preferably two absorption maxima, within the range of between about 400 and less than 590 nanometers. The organic photochromic substances are used in a proportion to achieve a near neutral coloring of the article. The article may also be tinted with a light compatible tint (dye) to achieve a more neutral color when the photochromic substances are activated.

Method for preparing variable-light transmittance article

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.

Polyol(allyl carbonate) compositions and polymerizates prepared therefrom

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.

Photochromic polymeric article

Variable-transmittance articles, such as an ophthalmic lens, are prepared by applying to or incorporating within the article a combination of two (or more) organic photochromic substances exhibiting different activated absorption maxima within the matrix in which the substances are incorporated. One organic photochromic substance has an absorption maximum within the range of between greater than 590 and about 700 nanometers. The other organic photochromic substance exhibits at least one absorption maximum and preferably two absorption maxima, within the range of between about 400 and less than 500 nanometers. The organic photochromic substances are used in a proportion to achieve a near neutral coloring of the article. The article may also be tinted with a light compatible tint (dye) to achieve a more neutral color when the photochromic substances are activated.

Variable-light transmittance article and method for preparing same

Organic peroxydicarbonates such as bis[3-(isobutyryloxy)-2,2,4-trimethylpentyl] peroxydicarbonate are described. The peroxydicarbonates are useful as initiators for the polymerization or copolymerization of vinyl acetate and may be used in combination with the more commonly used peroxydicarbonates such as diisopropyl peroxydicarbonate.

Novel organic peroxydicarbonates

Compound represented by the formula ##STR1## wherein each X is independently chloro or bromo is employed as a pyrolysis promoter in the pyrolysis of 1,2-dichloroethane to vinyl chloride.

Method for producing vinyl chloride

Aldoxime or ketoxime-O-alkanoic acid is prepared by transoximation of an aldehyde or ketone, the reaction being conducted in a liquid phase at a pressure below one atmosphere. Conversion of the aldoxime or ketoxime-O-alkanoic acid to the ester or salt form is also described.

Method for preparing aldoxime or ketoxime-O-alkanoic acid

Disclosed are polymer blends of bis(allyl carbonate) polymers with polymers of olefinically unsaturated monomers, and the precursor blends of bis(allyl carbonate) monomers with polymers of olefinically unsaturated monomers, and fabricable resins prepared therefrom. Also disclosed is a method of fabricating, e.g., molding, injection molding, extruding, and the like, the fabricable resins. The bis(allyl carbonate) polymer blend is taken to a fabricable state, i.e., a fusible pseudoplastic that does not lose liquid on fabrication, either by admixture or admixture and reaction. The fabricable resin is then fabricated, e.g., extruded, molded, or the like, and then polymerized to a hard polymer. Also disclosed are blends of bis(allyl carbonates), monomeric and polymeric, with polymers having olefinic unsaturation.

Blends of bis(allyl carbonate) monomers with polymers and polymer blends

Method of polymerizing blends of bis (allyl carbonate) monomers with

Boron trichloride is prepared by free-radical chlorination of liquid borate ester, e.g., trimethyl borate, at temperatures of between about 20.degree. C. and 100.degree. C. Color bodies which form and accumulate in the liquid reaction mixture are removed by extracting a purge fraction of the reaction mixture from the reactor, distilling such liquid reaction mixture, and recycling distillate obtained from the distillation to the reactor. The volume of the purge fraction can vary between about 4 and about 20 volume percent of the reaction mixture per hour. Borate ester can be added to the distillate before introducing it into the reactor.

Growing community of inventors

Akron, OH, United States of America

John C Crano