# US 2019/0315909 A1 · Polyurethane comprising graphene nano structure

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- Number: US 2019/0315909 A1
- Document ID: US20190315909A1
- Status: Published application
- Kind: A1
- Application number: 16/348,243
- Filed: 2017-11-09
- Published: 2019-10-17
- Earliest claimed: 2016-11-09
- Assignees: BASF SE
- Applicants: BASF SE
- Inventors: Janine Luesing; Michael Jae Lubitz
- Web page: https://patentgrep.com/patent/US20190315909A1

## CPC

- C08G 18/7671: {containing only one alkylene bisphenyl group}
- C08G 18/10: Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
- C08G 18/12: using two or more compounds having active hydrogen in the first polymerisation step
- C08G 18/1808: {having alkylene polyamine groups}
- C08G 18/4018: {Mixtures of compounds of group C08G18/42 with compounds of group C08G18/48}
- C08G 18/4238: {derived from dicarboxylic acids and dialcohols}
- C08G 18/4277: {Caprolactone and/or substituted caprolactone}
- C08G 18/48: Polyethers
- C08G 18/4854: {Polyethers containing oxyalkylene groups having four carbon atoms in the alkylene group}
- C08G 18/4887: {containing carboxylic ester groups derived from carboxylic acids other than acids of higher fatty oils or other than resin acids}
- C08K 3/042: {Graphene or derivatives, e.g. graphene oxides}
- C08K 5/0025: {Crosslinking or vulcanising agents; including accelerators}
- C08K 5/053: Polyhydroxylic alcohols
- C08K 5/17: Amines; Quaternary ammonium compounds
- C08K 7/00: Use of ingredients characterised by shape
- C08L 75/04: Polyurethanes
- C08K 2201/005: Additives being defined by their particle size in general
- C08K 2201/011: Nanostructured additives
- C08L 2207/04: Thermoplastic elastomer
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08K: Use of inorganic or non-macromolecular organic substances as compounding ingredients (paints, inks, varnishes, dyes, polishes, adhesives C09)
- C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06)

## Abstract

Described herein is a cast elastomer including graphene nano platelets and a process for preparing the same.

## Claims

### Claim 1

A cast elastomer comprising a reaction product of:
(A) 10 wt.-% to 98 wt.-% of at least one isocyanate component,
(B) 2 wt.-% to 90 wt.-% of at least one polyol component,
(C) 0.1 wt.-% to 20 wt.-% of graphene nano platelets having an average lateral dimension (x, y) in a range of 1 μm to 100 μm determined by atomic force microscope, an average through-plane dimension (z) in a range of 5 nm to 100 nm determined by atomic force microscope and an oxygen content in a range of 0.01 wt.-% to 10 wt.-% based on a total weight of the graphene nano platelets, and
(D) 1 wt.-% to 30 wt.-% of at least one cross-linker or a chain extender,
wherein the wt.-% is based on a total weight of the cast elastomer and
wherein the cast elastomer has a hard segment content in a range of 50% to 97%, the hard segment content being defined by a formula:
Hard segment content={Σx=1n[mCE/EWCE]/[mICN/EWICN]}×100%
wherein,
mCE is a mass of the at least one cross linker or the chain extender in g,
EWCE is an equivalent weight of the at least one cross linker or the chain extender in g/eq,
mICN is a mass of the at least one isocyanate component in g,
EWICN is an equivalent weight of the at least one isocyanate component in g/eq, and
n is a number of cross linker or chain extender and the isocyanate.

### Claim 2 (depends on 1)

The cast elastomer according to claim 1, characterized in that the at least one isocyanate component (A) is selected from the group consisting of at least one diisocyanate component (A1), at least one polymeric diisocyanate component (A2) and a mixture thereof.

### Claim 3 (depends on 2)

The cast elastomer according to claim 2, characterized in that the at least one diisocyanate component (A1) comprises an aromatic diisocyanate (A11) having NCO content in a range of 2 wt.-% to 50 wt.-%.

### Claim 4 (depends on 3)

The cast elastomer according to claim 3, characterized in that the aromatic diisocyanate (A11) is selected from the group consisting of tetramethylxylylene diisocyanate (TMXDI), 1,4-diisocyanatobenzene, 1,3-diisocyanato-o-xylene, 1,3-diisocyanato-p-xylene, 1,3-diisocyanato-m-xylene, 2,4-diisocyanato-1-chlorobenzene, 2,4-diisocyanato-1-nitrobenzene, 2,5-diisocyanato-1-nitrobenzene, m-phenylene diisocyanate, p-phenylene diisocyanate, 2,4-toluene diisocyanate, 2,6-toluene diisocyanate, 1,5-naphthalene diisocyanate, 1-methoxy-2,4-phenylene diisocyanate, 2,2′-diphenylmethane diisocyanate, 4,4′-diphenylmethane diisocyanate, 2,4′-diphenylmethane diisocyanate, 4,4′-biphenylene diisocyanate, 3,3′-dimethyl-4,4′-diphenylmethane diisocyanate, 3,3′-dimethyl diphenylmethane-4,4′-diisocyanate and combinations thereof.

### Claim 5 (depends on 2)

The cast elastomer according to claim 2, characterized in that the at least one polymeric diisocyanate component (A2) has NCO content in a range of 15 wt.-% to 35 wt.-%.

### Claim 6 (depends on 1)

The cast elastomer according to claim 1, characterized in that the at least one isocyanate component (A) is present in an amount in a range of 15 wt.-% to 85 wt.-% based on a total weight of the cast elastomer.

### Claim 7 (depends on 1)

The cast elastomer according to claim 1, characterized in that the at least one polyol component (B) has a hydroxyl number in a range of 10 mgKOH/g to 1000 mgKOH/g.

### Claim 8 (depends on 1)

The cast elastomer according to claim 1, characterized in that the at least one polyol component (B) is selected from the group consisting of polyether polyol (B1), polyester polyol (B2), natural oil polyol (B3), polydiene polyol (B4), copolymers and combinations thereof.

### Claim 9 (depends on 1)

The cast elastomer according to claim 1, characterized in that the at least one polyol component (B) is present in an amount in a range of 15 wt.-% to 85 wt.-% based on the total weight of the cast elastomer.

### Claim 10 (depends on 1)

The cast elastomer according to claim 1, characterized in that the at least one cross-linker or the chain extender (D) is selected from the group consisting of ethylene glycol, propylene glycol, butylene glycol, 1,4-butanediol (BDO), 1,3-butanediol, butenediol, butynediol, xylylene glycol, amylene glycol, dipropylene glycol, diethylene glycol, unsubstituted, linear or branched C6 to C12 diols, 1,4-phenylene-bis-beta-hydroxy ethyl ether, 1,3-phenylenebis-beta-hydroxy ethyl ether, hydroquinone bis(2-hydroxyethyl)ether (HQEE), bis-(hydroxy-methylcyclohexane), hexanediol, thiodiglycol, ethylene diamine, propylene diamine, butylene diamine, hexamethylene diamine, cyclohexylene diamine, phenylene diamine, tolylene diamine, xylylene diamine, 3,3′-dichlorobenzidine, 3,3′-dinitrobenzidine, ethanol amine, aminopropyl alcohol, 2,2-dimethyl propanol amine, 3-aminocyclohexyl alcohol, p-aminobenzyl alcohol, glycerine, trimethylolpropane (TMP), pentaerythritol, dimethylthiotoluenediamine, 3,5-diethyltoluene-2,4-diamine, 3,5-diethyltoluene-2,6-diamine, 2-methyl-1,3-propanediol, 4,4′-methylenebis(2-chloroanaline), 1,3-propanediol, castor oil, tetrahydroxypropyl ethylenediamine, triisopropanolamine, triethanolamine and a mixture thereof.

### Claim 11 (depends on 1)

The cast elastomer according to claim 1, characterized in that the at least one cross-linker or the chain extender (D) is present in an amount in a range of 1 wt.-% to 30 wt.-% based on a total weight of the cast elastomer.

### Claim 12 (depends on 1)

A process for preparing a cast elastomer according to claim 1, comprising the steps of:
(A′) preparing an isocyanate prepolymer comprising the at least one isocyanate component (A), the at least one polyol component (B) and the graphene nano platelets (C),
wherein the isocyanate prepolymer has an isocyanate index in a range of 1 to 300, and
(B′) reacting the isocyanate prepolymer of step (A′) with the at least one cross-linker or the chain extender (D) to obtain a cast elastomer having a hard segment content in a range of 50% to 97%, the hard segment content being defined by a formula:
Hard segment content={Σx=1n[mCE/EWCE]/[mICN/EWICN]}×100%
wherein,
mCE is a mass of the at least one cross linker or the chain extender in g,
EWCE is an equivalent weight of the at least one cross linker or the chain extender in g/eq,
mICN is a mass of the at least one isocyanate component in g,
EWICN is an equivalent weight of the at least one isocyanate component in g/eq,
n is a number of cross linker or chain extender and the isocyanate,
wherein the graphene nanoplatelets (C) have an average lateral dimension (x, y) in a range of 1 μm to 100 μm determined by atomic force microscope, an average through-plane dimension (z) in a range of 5 nm to 100 nm determined by atomic force microscope and an oxygen content in a range of 0.01 wt.-% to 10 wt.-% based on a total weight of the graphene nano platelets (C).

### Claim 13 (depends on 12)

The process according to claim 12, characterized in that the step (A′) is substantially free of any solvent.

### Claim 14 (depends on 12)

The process according to claim 12, characterized in that in step (A′) the isocyanate prepolymer is obtained by:
(A1′) mixing the at least one polyol component (B) and the graphene nanoplatelets (C) to obtain an isocyanate reactive mixture,
(A2′) adding the isocyanate reactive mixture of step (A1′) and the at least one isocyanate component (A) optionally in the presence of the at least one crosslinker or the chain extender (D) to obtain an isocyanate prepolymer having an NCO content in a range of 2 wt.-% to 50 wt.-%.

### Claim 15 (depends on 12)

The process according to claim 12, characterized in that in step (A′) the graphene nano platelets (C) are first mixed with the at least one isocyanate component (A) to obtain a mixture.

### Claim 16 (depends on 12)

The process according to claim 12, characterized in that the graphene nano platelets (C) are present in the form of a powder or in the form of a dispersion.

### Claim 17 (depends on 1)

A method of using the cast elastomer according to claim 1 in an article.

### Claim 18 (depends on 1)

An article comprising the cast elastomer according to claim 1.

### Claim 19 (depends on 12)

A method of using the cast elastomer obtained by the process according to claim 12 in an article.

### Claim 20 (depends on 12)

An article comprising the cast elastomer obtained by the process according to claim 12.