Process for the production of organic hydroxy silicate compounds and their resinous products

Claim 2

The process for the production of an epoxy silicate resinous product by the following steps: (a) mixing 1 part by weight of fine granular silica with 1 to 6 parts by weight of an organic polyhydroxy compound; (b) adding 0.25 to 1 part by weight of an alkali metal hydroxide catalyst, selected from the group consisting of sodium hydroxide and potassium, in water; (c) heating the mixture to just below the boiling temperature of the mixture while agitating for 30 to 60 minutes, thereby producing an organic hydroxy silicate compound; (d) adding 2 to 3 mols of an epoxy compound to about 1 mol of said organic hydroxy silicate compound then agitating while heating, at ambient pressure to 60 psig, to just below the boiling temperature of the reactants for 10 to 60 minutes, thereby (e) producing an epoxy organic hydroxy silicate compound; (f) adding a catalytic amount to 1 mol for each mol of the epoxy hydroxide silicate compound of a catalyst selected from the group consisting of a Lewis acid and an amine compound, thereby (g) producing an epoxy silicate resinous product.

Claim 3

The process of claim 1 wherein the epoxy compound is selected from the group consisting of epichlorohydrin, 1 part by weight of epichlorohydrin with 0.5 to 4 parts by weight of an epoxy resin containing 2 or more reactive epoxy groups per molecule, 1 part by weight of epichlorohydrin with 0.5 to 4 parts by weight of an epoxidized olefin compound containing 2 or more reactive epoxy groups per molecule and mixtures thereof.

Claim 4

The process of claim 1 wherein the amine compound is selected from the group consisting of primary aliphatic polyamines, primary aromatic polyamines, polyamides containing 2 or more reactive amine groups per molecule, and mixtures thereof.

Claim 5

The product by the process of claim 1.

Claim 6

The process for the production of an acrylate organic hydroxy silicate resinous product by the following steps: (a) mixing 1 part by weight of fine granular silica with 1 to 6 parts by weight of an organic polyhydroxy compound; (b) adding 0.25 to 1 part by weight of an alkali metal hydroxide catalyst, selected from the group consisting of sodium hydroxide and potassium hydroxide, in water; (c) heating the mixture to just below the boiling temperature of the mixture while agitating for 30 to 60 minutes, thereby producing an organic hydroxy silicate compound; (d) mixing 0.5 to 4 parts by weight of said organic hydroxy silicate compound and an acrylic compound in the amount of 1 to 50 parts by weight and selected from the group consisting of acrylic acid, methacrylic acid, ethyl acrylic acid, crotonic acid, chloroacrylic acid, fluoroacrylic acid, cyclohexyl methacrylic acid, isobutyl methacrylic acid, bromoacrylic acid, hydroacrylic acid, benzyl acrylic acid, methyl methacrylate, methyl acrylate, ethyl acrylate, propyl acrylate, butyl acrylate, pentadecyl acrylate, hexadecyl acrylate, benzyl acrylate, cyclohexyl acrylate, phenyl ethyl acrylate, ethyl methacrylate, methyl α-chloroacrylate, 2-chloroethyl acrylate, 1,1-dihydroperfluorobutyl acrylate, lauryl acrylate, cyclohexyl-cyclohexyl methacrylate, allyl methacrylate and mixtures thereof; then a catalytic amount of an initiator is added, and the mixture is agitated at ambient pressure to 60 psig at a temperature of ambient temperature to just below the boiling point of the reactants for 0.5 to 12 hours, thereby (e) producing an acrylate organic hydroxy silicate resinous product.

Claim 7

The process for the production of an acrylate organic hydroxy silicate resinous product by the following steps: (a) mixing 1 part by weight of fine granular silica with 1 to 6 parts by weight of an organic polyhydroxy compound; (b) adding 0.25 to 1 part by weight of an alkali metal hydroxide catalyst, selected from the group consisting of sodium hydroxide and potassium hydroxide, in water; (c) heating the mixture to just below the boiling temperature of the mixture while agitating for 30 to 60 minutes, thereby producing an organic hydroxy silicate compound; (d) mixing 0.5 to 4 parts by weight of said organic hydroxy silicate compound and an acrylic compound in the amount of 1 to 50 parts by weight and selected from the group consisting of acrylic acid, methacrylic acid, ethyl acrylic acid, crotonic acid, chloroacrylic acid, fluoroacrylic acid, cyclohexyl methacrylic acid, isobutyl methacrylic acid, bromoacrylic acid, hydroacrylic acid, benzyl acrylic acid, methyl methacrylate, methyl acrylate, ethyl acrylate, propyl acrylate, butyl acrylate, pentadecyl acrylate, hexadecyl acrylate, benzyl acrylate, cyclohexyl acrylate, phenyl ethyl acrylate, ethyl methacrylate, methyl α-chloroacrylate, 2-chloroethyl acrylate, 1,1-dihydroperfluorobutyl acrylate, lauryl acrylate, cyclohexyl-cyclohexyl methacrylate, allyl methacrylate and mixtures thereof; then a catalytic amount of an initiator is added, and the mixture is agitated at ambient pressure to 60 psig at a temperature of ambient temperature to just below the boiling point of the reactants for 0.5 to 12 hours, thereby (e) producing an acrylate organic hydroxy silicate resinous product.

Claim 8

The process of claim 5 wherein the initiator is selected from the group consisting of a peroxide initiator, alkali persulfate, peroxide initiator utilized in a redox system, peroxide initiator with a metal compound activator and ammonium persulfate.

Claim 9

The process for the production of an organic copolymer-organic hydroxy silicate resinous product by the following steps: (a) mixing 1 part by weight of fine granular silica with 1 to 6 parts by weight of an organic polyhydroxy compound; (b) adding 0.25 to 1 part by weight of an alkali metal hydroxide, selected from the group consisting of sodium hydroxide and potassium hydroxide, in water; (c) heating the mixture to just below the boiling temperature of the mixture while agitating for 30 to 60 minutes, thereby producing an organic hydroxy silicate compound; (d) mixing 0.5 to 4 parts by weight of said organic hydroxy silicate compound with 1 to 10 parts by weight of an acrylic compound and 0.5 to 10 parts by weight of a polymerable organic compound, selected from the group consisting of vinyl monomers, organic dienes, aliphatic allyl compounds, organic oxides, aliphatic hydrocarbons and mixtures thereof; then a catalytic amount of an initiator is added, and the mixture is agitated at a temperature wherein the reactants are in a liquid or compressed state and at ambient pressure to 60 psig for 0.5 to 12 hours, thereby producing an organic copolymer-organic hydroxy silicate resinous product.

Claim 10

The process for the production of an organic copolymer-organic hydroxy silicate resinous product by the following steps: (a) mixing 1 part by weight of fine granular silica with 1 to 6 parts by weight of an organic polyhydroxy compound; (b) adding 0.25 to 1 part by weight of an alkali metal hydroxide, selected from the group consisting of sodium hydroxide and potassium hydroxide, in water; (c) heating the mixture to just below the boiling temperature of the mixture while agitating for 30 to 60 minutes, thereby producing an organic hydroxy silicate compound; (d) mixing 0.5 to 4 parts by weight of said organic hydroxy silicate compound with 1 to 10 parts by weight of an acrylic compound and 0.5 to 10 parts by weight of a polymerable organic compound, selected from the group consisting of vinyl monomers, organic dienes, aliphatic allyl compounds, organic oxides, aliphatic hydrocarbons and mixtures thereof; then a catalytic amount of an initiator is added, and the mixture is agitated at a temperature wherein the reactants are in a liquid or compressed state and at ambient pressure to 60 psig for 0.5 to 12 hours, thereby producing an organic copolymer-organic hydroxy silicate resinous product.

Claim 11

The process of claim 7 wherein the vinyl monomer is selected from the group consisting of styrene, vinyl acetate, vinyl chloride, vinylidene chloride, acrylonitrile, vinyl toluenes and mixtures thereof.

Claim 12

The process of claim 7 wherein the organic diene is selected from the group consisting of isoprene, chloroprene, butadiene and mixtures thereof.

Claim 13

The process of claim 7 wherein the aliphatic allyl compound is selected from the group consisting of allyl alcohol, 3-chloropropene, 3-bromopropene, methallyl chloride and mixtures thereof.

Claim 14

The process of claim 7 wherein the organic oxide is selected from the group consisting of propylene oxide, ethylene oxide, styrene oxide ane mixtures thereof.

Claim 15

The process of claim 7 wherein the organic aliphatic hydrocarbon is selected from the group consisting of ethylene and propylene.

Claim 16

The process of claim 7 wherein the initiator is selected from the group consisting of peroxide initiators, alkali metal persulfates, ammonium persulfate peroxide initiator utilized in a redox system and peroxide initators with a metal compound activator.

Claim 17

The process for the production of an acrylate organic hydroxy silicate resinous product by the following steps: (a) mixing 1 part by weight of fine granular silica with 1 to 6 parts by weight of an organic polyhydroxy compound; (b) adding 0.25 to 1 part by weight of an alkali metal hydroxide, selected from the group consisting of sodium hydroxide and potassium hydroxide, in water; (c) heating the mixture to just below the boiling temperature of the mixture while agitating for 30 to 60 minutes, thereby producing an organic hydroxy silicate compound; (d) mixing about 1 mol of said organic hydroxy silicate with 1 to 2 mols of an acrylic acid compound, then heating to just below the boiling temperature of the reactants while agitating for 20 to 60 minutes, thereby producing an acrylate organic hydroxy silicate compound; then a catalytic amount of an initiator, selected from the group consisting of peroxide initiators, alkali metal persulfate, ammonium persulfate, peroxide initiator utilized in a redox system and a peroxide initiator with a metal compound activator, is added while agitating the mixture at ambient temperature to just below the boiling point of the reactants for 0.5 to 12 hours, thereby producing an acrylate organic hydroxy silicate resinous product.

Claim 18

The process for the production of an acrylate organic hydroxy silicate resinous product by the following steps: (a) mixing 1 part by weight of fine granular silica with 1 to 6 parts by weight of an organic polyhydroxy compound; (b) adding 0.25 to 1 part by weight of an alkali metal hydroxide, selected from the group consisting of sodium hydroxide and potassium hydroxide, in water; (c) heating the mixture to just below the boiling temperature of the mixture while agitating for 30 to 60 minutes, thereby producing an organic hydroxy silicate compound; (d) mixing about 1 mol of said organic hydroxy silicate with 1 to 2 mols of an acrylic acid compound, then heating to just below the boiling temperature of the reactants while agitating for 20 to 60 minutes, thereby producing an acrylate organic hydroxy silicate compound; then a catalytic amount of an initiator, selected from the group consisting of peroxide initiators, alkali metal persulfate, ammonium persulfate, peroxide initiator utilized in a redox system and a peroxide initiator with a metal compound activator, is added while agitating the mixture at ambient temperature to just below the boiling point of the reactants for 0.5 to 12 hours, thereby producing an acrylate organic hydroxy silicate resinous product.

Claim 19

The product produced by the process of claim 14.

Claim 20

The process for the production of a cyanoacrylate-organic hydroxy silicate resinous product by the following steps: (a) mixing 1 part by weight of fine granular silica with 1 to 6 parts by weight of an organic polyhydroxy compound; (b) adding 0.25 to 1 part by weight of an alkali metal hydroxide selected from the group consisting of sodium hydroxide and potassium hydroxide, in water; (c) heating the mixture to just below the boiling temperature of the mixture while agitating for 30 to 60 minutes, thereby producing an organic hydroxy silicate compound; (d) adding about 1 to 10 mols of an alkali metal cyanide, selected from the group consisting of sodium cyanide and potassium cyanide, and 10 mols of an acrylic acid compound, selected from the group consisting of acrylic acid, methacrylic acid, ethyl acrylic acid, chloroacrylic acid, hydroacrylic acid, isobutyl methacrylic acid, fluoroacrylic acid, crotonic acid, bromoacrylic acid, benzyl acrylic acid and mixtures thereof, to 0.5 to 5 mols of said organic hydroxy compound, then heating to just below the boiling temperature of the reactants while agitating for 20 to 60 minutes, thereby producing an alkali metal cyanoacrylate organic hydroxy silicate compound; (e) adding a dilute mineral acid in the amount of mols equal to the mols of alkali metal atoms to said alkali metal cyanoacrylate organic hydroxy silicate compound while agitating, and the salt is then filtered off, thereby producing a cyanoacrylate organic hydroxy silicate compound; (f) adding a catalytic amount of an initiator, selected from the group consisting of peroxide initiators, alkali metal persulfates, ammonium persulfates, peroxide initiator utilized in a redox system and peroxide initiators with a metal compound activator, to the cyanoacrylate organic hydroxy silicate compound while agitating at ambient temperature to just below the boiling temperature of the reactants for 0.5 to 12 hours, thereby producing a cyano-acrylate-organic hydroxy silicate resinous product.

Claim 21

The process for the production of a cyanoacrylate-organic hydroxy silicate resinous product by the following steps: (a) mixing 1 part by weight of fine granular silica with 1 to 6 parts by weight of an organic polyhydroxy compound; (b) adding 0.25 to 1 part by weight of an alkali metal hydroxide selected from the group consisting of sodium hydroxide and potassium hydroxide, in water; (c) heating the mixture to just below the boiling temperature of the mixture while agitating for 30 to 60 minutes, thereby producing an organic hydroxy silicate compound; (d) adding about 1 to 10 mols of an alkali metal cyanide, selected from the group consisting of sodium cyanide and potassium cyanide, and 10 mols of an acrylic acid compound, selected from the group consisting of acrylic acid, methacrylic acid, ethyl acrylic acid, chloroacrylic acid, hydroacrylic acid, isobutyl methacrylic acid, fluoroacrylic acid, crotonic acid, bromoacrylic acid, benzyl acrylic acid and mixtures thereof, to 0.5 to 5 mols of said organic hydroxy compound, then heating to just below the boiling temperature of the reactants while agitating for 20 to 60 minutes, thereby producing an alkali metal cyanoacrylate organic hydroxy silicate compound; (e) adding a dilute mineral acid in the amount of mols equal to the mols of alkali metal atoms to said alkali metal cyanoacrylate organic hydroxy silicate compound while agitating, and the salt is then filtered off, thereby producing a cyanoacrylate organic hydroxy silicate compound; (f) adding a catalytic amount of an initiator, selected from the group consisting of peroxide initiators, alkali metal persulfates, ammonium persulfates, peroxide initiator utilized in a redox system and peroxide initiators with a metal compound activator, to the cyanoacrylate organic hydroxy silicate compound while agitating at ambient temperature to just below the boiling temperature of the reactants for 0.5 to 12 hours, thereby producing a cyano-acrylate-organic hydroxy silicate resinous product.

Claim 22

The product by the process of claim 16.

Claim 23

The process of claim 1 wherein the organic polyhydroxy compound is selected from the group consisting of glycerol, glycerol monochlorohydrin, sorbitol, mannitol, pentaerythritol, di- and tripentaerythritol, ethylene glycol, propylene glycol, butylene glycol, trimeth glycol, tetramethylene glycol, pentamethylene glycol, hexamethylene glycol, diethylene glycol, polyethylene glycols and ether glycol, triethylene glycol, dipropylene glycol, tetraethylene glycol, bis(betahydroxyethyl) terephthalate, trimethylol propane, trimethylol ethane, 2,2'-oxydiethanol, glucose, mannose, fructose, molasses, cane sugar, dextrines, starches, corn syrup, maple syrup and mixtures thereof.

Claim 24

The process of claim 5 wherein the organic polyhydroxy compound is selected from the group consisting of glycerol, glycerol monochlorohydrin, sorbitol, mannitol, pentaerythritol, di- and tripentaerythritol, ethylene glycol, propylene glycol, butylene glycol, trimethylene glycol, tetramethylene glycol, pentamethylene glycol, hexamethylene glycol, diethylene glycol, polyethylene glycols and ether glycol, triethylene glycol, dipropylene glycol, tetraethylene glycol, bis(betahydroxy-ethyl) terephthalate, trimethylol propane, trimethylol ethane, 2,2'-oxydiethanol, glucose, mannose, fructose, molasses, cane sugar, dextrines, starches, corn syrup, maple syrup and mixtures thereof.

Claim 25

The process of claim 7 wherein the organic polyhydroxy compound is selected from the group consisting of glycerol, glycerol monochlorohydrin, sorbitol, mannitol, pentaerythritol, di- and tripentaerythritol, ethylene glycol, propylene glycol, butylene glycol, trimethylene glycol, tetramethylene glycol, pentamethylene glycol, hexamethylene glycol, diethylene glycol, polyethylene glycols and ether glycol, triethylene glycol, dipropylene glycol, tetraethylene glycol, bis(betahydroxyethyl) terephthalate, trimethylol propane, trimethylol ethane, 2,2'-oxydiethanol, glucose, mannose, fructose, molasses, cane sugar, dextrines, starches, corn syrup, maple syrup and mixtures thereof.

Claim 26

The process of claim 14 wherein the organic polyhydroxy compound is selected from the group consisting of glycerol, glycerol monochlorohydrin, sorbitol, mannitol, pentaerythritol, di- and tripentaerythritol, ethylene glycol, propylene glycol, butylene glycol, trimethylene glycol, tetramethylene glycol, pentamethylene glycol, hexamethylene glycol, diethylene glycol, polyethylene glycols and ether glycol, triethylene glycol, dipropylene glycol, tetraethylene glycol, bis(betahydroxyethyl) terephthalate, trimethylol propane, trimethylol ethane, 2,2'-oxydiethanol, glucose, mannose, fructose, molasses, cane sugar, dextrines, starches, corn syrup, maple syrup and mixtures thereof.

Claim 27

The process of claim 16 wherein the organic polyhydroxy compound is selected from the group consisting of glycerol, glycerol monochlorohydrin, sorbitol, mannitol, pentaerythritol, di- and tripentaerythritol, ethylene glycol, propylene glycol, butylene glycol, trimethylene glycol, tetramethylene glycol, pentamethylene glycol, hexamethylene glycol, diethylene glycol, polyethylene glycols and ether glycol, triethylene glycol, dipropylene glycol, tetraethylene glycol, bis(betahydroxyethyl) terephthalate, trimethylol propane, trimethylol ethane, 2,2'-oxydiethanol, glucose, mannose, fructose, molasses, cane sugar, dextrines, starches, corn syrup, maple syrup and mixtures thereof.

Claim 28

The product produced by the process of claim 5.

Claim 29

The product produced by the process of claim 7.