# US 12,110,390 B2 · Solid dispersion, preparation method therefor, chain-extended polyurethane using same, and epoxy resin composition comprising same

> Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt

- Number: US 12,110,390 B2
- Document ID: US12110390B2
- Status: Granted
- Kind: B2
- Application number: 17/054,286
- Filed: 2019-05-10
- Published: 2021-08-05
- Granted: 2024-10-08
- Earliest claimed: 2018-05-11
- Assignees: Samyang Corporation
- Applicants: Samyang Corporation
- Inventors: Gwang Seok Song; Hoon Ryu; Jun Seop Im; Seung Hyun Yoo; Won Hyun Jeon
- Web page: https://patentgrep.com/patent/US12110390B2

## CPC

- C08G 18/4854: {Polyethers containing oxyalkylene groups having four carbon atoms in the alkylene group}
- C08L 75/08: from polyethers
- C08G 18/0866: {the dispersing or dispersed phase being an aqueous medium}
- C08G 18/10: Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
- C08G 18/7671: {containing only one alkylene bisphenyl group}
- C08J 3/09: in organic liquids
- C08J 3/095: {Oxygen containing compounds}
- C08K 3/042: {Graphene or derivatives, e.g. graphene oxides}
- C08K 5/053: Polyhydroxylic alcohols
- C08K 5/1535: Five-membered rings
- C08K 5/17: Amines; Quaternary ammonium compounds
- C08K 5/3445: Five-membered rings
- C08L 63/00: Compositions of epoxy resins; Compositions of derivatives of epoxy resins
- C08L 71/02: Polyalkylene oxides
- C09K 23/00: Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
- C09K 23/002: {Inorganic compounds}
- C08J 2301/02: Cellulose; Modified cellulose
- C08J 2363/00: Characterised by the use of epoxy resins; Derivatives of epoxy resins
- C08J 2375/04: Polyurethanes
- C08J 2375/08: from polyethers
- C08J 2401/02: Cellulose; Modified cellulose
- C08J 2463/00: Characterised by the use of epoxy resins; Derivatives of epoxy resins
- C08J 2475/08: from polyethers
- C08L 2205/16: Fibres; Fibrils
- C09K 23/16: Amines or polyamines
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06)
- C08J: WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H (working, e.g. shaping, of plastics B29)
- C08K: Use of inorganic or non-macromolecular organic substances as compounding ingredients (paints, inks, varnishes, dyes, polishes, adhesives C09)
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE

## Abstract

The present invention relates to a solid dispersion, a preparation method therefor, a chain-extended polyurethane using same, and an epoxy resin composition comprising same and, more particularly, to a solid dispersion in which an inorganic or organic material-derived isotropic or anisotropic substance is used as a dispersoid and dispersed at room temperature in a solid-phase dispersion medium such as polyols and sugars, whereby the dispersion can be easily stored and used, reduce transportation cost, prevent or alleviate the aggregation or precipitation caused during the storage of products, with the results of working efficiency improvement and processing cost reduction, and, when applied to polyurethane, can increase strength and provide an improved strength, compared to conventional curing agent, a preparation method therefor, a chain-extended polyurethane using same, and an epoxy resin composition comprising same.

## Claims

### Claim 1

A solid dispersion comprising a dispersoid and a dispersion medium in which the dispersoid is dispersed,
wherein the dispersoid is an organic particle, an inorganic particle or a mixture thereof,
the dispersion medium is a non-aqueous dispersion medium in a solid state at room temperature,
the solid dispersion does not comprise any dispersant or surfactant,
the inorganic particle is selected from the group consisting of iron, aluminum, chromium, nickel, cobalt, zinc, tungsten, indium, tin, palladium, zirconium, titanium, copper, silver, gold, platinum, kaolin, clay, talc, mica, bentonite, dolomite, calcium silicate, magnesium silicate, asbestos, calcium carbonate, magnesium carbonate, barium carbonate, calcium sulfate, barium sulfate, aluminum sulfate, aluminum hydroxide, iron hydroxide, aluminum silicate, zirconium oxide, magnesium oxide, aluminum oxide, titanium oxide, iron oxide, zinc oxide, antimony trioxide, indium oxide, indium tin oxide, silicon carbide, silicon nitride, boron nitride, barium titanate, diatomite, carbon black, graphite, rock wool, glass wool, glass fiber, graphene, carbon fiber, carbon nanofibers, carbon nanotubes, an alloy of two or more metals of them or a mixture of two or more of them,
the organic particle is selected from the group consisting of azo-based compounds, diazo-based compounds, condensed azo-based compounds, thioindigo-based compounds, indanthrone-based compounds, quinacridone-based compounds, anthraquinone-based compounds, benzimidazolone-based compounds, perylene-based compounds, phthalocyanine-based compounds, anthrapyridine-based compounds, dioxazine-based compounds, polyethylene resin, polypropylene resin, polyester resin, nylon resin, polyamide resin, aramid resin, acrylic resin, vinylon resin, urethane resin, melamine resin, polystyrene resin, polylactic acid, acetate fiber, cellulose, lignin, chitin, chitosan, starch, polyacetal, polycarbonate, polyphenylene ether, polyether ether ketone, polyether ketone, polybutylene terephthalate, polyethylene naphthalate, polybutylene naphthalate, polysulfone, polyphenylene sulfide, polyimide or mixtures thereof, and
the dispersion medium is one or more selected from the group consisting of polyether polyols, polyester polyols, hydrogenated sugars, alkane diols, phenol-based compounds, imidazole-based compounds, acid anhydride-based compounds, anhydrosugar alcohols or combinations thereof.

### Claim 2 (depends on 1)

The solid dispersion according to claim 1, wherein the content of the dispersoid is 0.0001 parts by weight to 95 parts by weight based on 100 parts by weight of the dispersion medium.

### Claim 3 (depends on 1)

The solid dispersion according to claim 1, which is a solid dispersion at room temperature for chain extension.

### Claim 4 (depends on 3)

A chain-extended polyurethane, which is prepared by the reaction of a polyurethane prepolymer and the solid dispersion of claim 3.

### Claim 5 (depends on 3)

A method for preparing a chain-extended polyurethane comprising
(1) a step of adding the solid dispersion of claim 3 to a polyurethane prepolymer; and
(2) a step of reacting the resulting mixture of step (1).

### Claim 6 (depends on 5)

The method of claim 5, wherein the polyurethane prepolymer is obtained by reacting a polyol—which are vacuum-dried at 50 to 100° C. for 12 to 36 hours—and a polyisocyanate at a temperature of 50 to 100° C. for 0.1 to 5 hours under a nitrogen atmosphere.

### Claim 7 (depends on 5)

The method of claim 5, wherein the step of the reacting the resulting mixture of step (1) is conducted by curing the resulting mixture for 10 to 30 hours at a temperature of 80 to 200° C.

### Claim 8 (depends on 1)

The solid dispersion according to claim 1, which is a solid dispersion at room temperature for curing.

### Claim 9 (depends on 8)

An epoxy resin composition comprising an epoxy resin; and the solid dispersion of claim 8.

### Claim 10 (depends on 9)

A cured product obtained by curing the epoxy resin composition of claim 9.

### Claim 11 (depends on 10)

A molded article comprising the cured product of claim 10.

### Claim 12 (depends on 8)

A method for preparing an epoxy resin composition comprising a step of mixing an epoxy resin and the solid dispersion of claim 8.

### Claim 13 (depends on 1)

A dispersion composition comprising the solid dispersion of claim 1.

### Claim 14 (depends on 1)

A method for preparing the solid dispersion according to claim 1 comprising
a step of mixing the dispersoid and the dispersion medium; and
a step of melting the dispersion medium in a mixture.

### Claim 15 (depends on 14)

The method of claim 14, wherein the step of melting the dispersion medium in the mixture is conducted by melting the mixture while removing moisture by applying a vacuum at a temperature equal to or higher than the melting point of the dispersion medium.

### Claim 16

A solid dispersion comprising a dispersoid and a dispersion medium in which the dispersoid is dispersed,
wherein the dispersoid is an organic particle, an inorganic particle or a mixture thereof,
the dispersion medium is a non-aqueous dispersion medium in a solid state at room temperature,
the solid dispersion does not comprise any dispersant or surfactant,
the inorganic particle is selected from the group consisting of iron, aluminum, chromium, nickel, cobalt, zinc, tungsten, indium, tin, palladium, zirconium, titanium, copper, silver, gold, platinum, kaolin, clay, talc, mica, bentonite, dolomite, calcium silicate, magnesium silicate, asbestos, calcium carbonate, magnesium carbonate, barium carbonate, calcium sulfate, barium sulfate, aluminum sulfate, aluminum hydroxide, iron hydroxide, aluminum silicate, zirconium oxide, magnesium oxide, aluminum oxide, titanium oxide, iron oxide, zinc oxide, antimony trioxide, indium oxide, indium tin oxide, silicon carbide, silicon nitride, boron nitride, barium titanate, diatomite, carbon black, graphite, rock wool, glass wool, glass fiber, graphene, carbon fiber, carbon nanofibers, carbon nanotubes, an alloy of two or more metals of them or a mixture of two or more of them,
the organic particle is selected from the group consisting of azo-based compounds, diazo-based compounds, condensed azo-based compounds, thioindigo-based compounds, indanthrone-based compounds, quinacridone-based compounds, anthraquinone-based compounds, benzimidazolone-based compounds, perylene-based compounds, phthalocyanine-based compounds, anthrapyridine-based compounds, dioxazine-based compounds, polyethylene resin, polypropylene resin, polyester resin, nylon resin, polyamide resin, aramid resin, acrylic resin, vinylon resin, urethane resin, melamine resin, polystyrene resin, polylactic acid, acetate fiber, cellulose, lignin, chitin, chitosan, starch, polyacetal, polycarbonate, polyphenylene ether, polyether ether ketone, polyether ketone, polybutylene terephthalate, polyethylene naphthalate, polybutylene naphthalate, polysulfone, polyphenylene sulfide, polyimide or mixtures thereof, and
wherein the dispersion medium is one or more selected from the group consisting of tetritan, pentitan, heptitan, sorbitan, mannitan, iditan, galactan, isosorbide, isomannide, isoidide, tetritol, pentitol, heptitol, sorbitol, mannitol, iditol, galactitol, modified polypropylene glycol, polytetramethylene ether glycol, butylene adipate diol, 1,6-hexanadipate diol, 1,4-butanediol, 1,6-hexanediol, 1,9-nonanediol, poly(ethylene glycol)diamine, (R)-(+)-1,1′-binaphthyl-2,2′-diamine, (S)-(−)-1,1′-binaphthyl-2,2′-diamine, 1,1′-binaphthyl-2,2′-diamine, 4-ethoxybenzene-1,2-diamine, (1R,2R)—N,N′-dimethyl-1,2-diphenylethane-1,2-diamine, N,N-bis(4-butylphenyl)benzene-1,4-diamine, 2,3-xylenol, 2,4-xylenol, 2,5-xylenol, 2,6-zylenol, 3,4-zylenol, 3,5-zylenol, 2,5-dimethylphenol, 2,3-dimethylphenol, imidazole, 1-(2-hydroxyethyl)imidazole, imidazole trifluoro methanesulfonate, imidazole-2-carboxylic acid, 4-bromo-1H-imidazole, N-benzyl-2-nitro-1H-imidazole-1-acetamide, 2-chloro-1H-imidazole, imidazole-d, imidazole-N, imidazole-2-C,N, (2-dodecen-1-yl) succinic anhydride, maleic anhydride, succinic anhydride, phthalic anhydride, glutaric anhydride, 3,4,5,6-tetrahydrophthalic anhydride, diglycolic anhydride, itaconic anhydride, trans-1,2-cyclohexanedicarboxylic anhydride, 2,3-dimethylmaleic anhydride, 3,3-tetramethylene glutaric anhydride, stearic anhydride, cis-aconitic anhydride, trimellitic anhydride chloride, phenylsuccinic anhydride, 3,3-dimethylglutaric anhydride, methylsuccinic anhydride or combinations thereof.

### Claim 17 (depends on 16)

A dispersion composition comprising the solid dispersion of claim 16.