Abstract: 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.

Abstract: 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.

Abstract: 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.

Abstract: 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.

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.

Abstract: 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.

Abstract: 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.

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.

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.

Abstract: 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.

Abstract: 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.

Abstract: 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.

Abstract: 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.

Abstract: 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.

Abstract: 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.

Abstract: 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.

Abstract: Boron trichloride is prepared in substantially stoichiometric quantities by free-radical chlorination of borate ester, e.g., trimethyl borate, at temperatures of between about 20.degree. C. and 100.degree. C., more preferably between about 40.degree. C. and about 90.degree. C. The mole ratio of chlorine to borate ester is from about 5.5:1 to about 7.5:1. Reactor pressures are moderate, e.g., generally less than 3 atmospheres absolute. Atmospheric pressure can be used. An inert liquid organic solvent, e.g., carbon tetrachloride, can be used as the reaction medium. Gaseous reaction products are removed from the reactor during the chlorination reaction. In addition to boron trichloride, carbon monoxide (rather than phosgene) and hydrogen chloride are the principal products of the chlorination reaction. Phosgene is produced in substantially lower amounts than when chlorination is conducted at autogeneous pressures and the chlorine:trimethyl borate mole ratio is 9:1 or more.

Abstract: Halogenated diaryl hydrogen phosphates having in admixture only a minor proportion of monoaryl and triaryl phosphates are prepared by selectively hydrolyzing a corresponding triaryl phosphate or by reacting 2,6-dihalophenols having bromine or iodine atoms in the 2 and 6 positions with a phosphorous oxyhalide in the presence of an aromatic tertiary amine or carboxylic acid amide and, preferably, an inert organic solvent to form a mixture of diaryl-phosphorohalidate and triaryl phosphate and hydrolyzing the mixture.

Abstract: Halogenated diaryl hydrogen phosphates having in admixture only a minor proportion of monoaryl and triaryl phosphates are prepared by selectively hydrolyzing a corresponding triaryl phosphate or by reacting 2,6-dihalophenols having bromine or iodine atoms in the 2 and 6 positions with a phosphorous oxyhalide in the presence of an aromatic tertiary amine or carboxylic acid amide and, preferably, an inert organic solvent to form a mixture of diarylphosphorohalidate and triaryl phosphate and hydrolyzing the mixture.