# US 9,796,849 B2 · Polyurethane composites comprising nanocrystalline cellulose and method for improving properties of polyurethanes thereof

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- Number: US 9,796,849 B2
- Document ID: US9796849B2
- Status: Granted
- Kind: B2
- Application number: 14/894,052
- Filed: 2014-05-22
- Published: 2016-04-21
- Granted: 2017-10-24
- Earliest claimed: 2013-05-29
- Assignees: Celluforce Inc.
- Applicants: Celluforce Inc.
- Inventors: Richard Berry; Alain Granger
- Web page: https://patentgrep.com/patent/US9796849B2

## CPC

- C08L 75/08: from polyethers
- C08G 18/4081: {Mixtures of compounds of group C08G18/64 with other macromolecular compounds}
- C08G 18/4829: {Polyethers containing at least three hydroxy groups (C08G18/4833 - C08G18/5096 take precedence)}
- C08G 18/4841: {containing oxyethylene end groups}
- C08G 18/6484: {Polysaccharides and derivatives thereof}
- C08G 18/7621: {being toluene diisocyanate including isomer mixtures}
- C08G 18/7671: {containing only one alkylene bisphenyl group}
- C08L 1/02: Cellulose; Modified cellulose
- C08G 2110/0008: flexible
- C08G 2110/0066: ≥ 150kg/m3
- C08G 2190/00: Compositions for sealing or packing joints
- C08G 2350/00: Acoustic or vibration damping material
- C08G 2380/00: Tyres
- C08K 2201/011: Nanostructured additives
- C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06)
- 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)

## Abstract

A process for preparing polyurethane composites includes (i) providing a dispersion of nanocrystalline cellulose in (a) one or more polyols, (b) one or more isocyanates, or (c) one or more polyols and one or more isocyanate, mixed together; wherein the amount of water in the nanocrystalline cellulose is less than about 1% w/w; (ii) mixing the dispersion of (i)(a) with an isocyanate or (i)(b) with a polyol and a catalyst to allow polymerization; or mixing the dispersion of (i)(c) and a catalyst to allow polymerization; and (iii) isolating the polyurethane composite. A method for improving properties of polyurethanes includes dispersing nanocrystalline cellulose into one or both parts of a two part polyol/isocyanate precursors prior to allowing polymerization of the precursors, wherein the amount of water in the nanocrystalline cellulose is less than about 1% w/w; mixing the dispersion with a catalyst; and polymerizing the precursors to provide the polyurethane.

## Claims

### Claim 1

A process for preparing a polyurethane composite comprising:
(i) providing a dispersion by
(a) dispersing nanocrystalline cellulose into one or more polyols,
(b) dispersing nanocrystalline cellulose into one or more isocyanates, or
(c) dispersing nanocrystalline cellulose into one or more polyols and one or more isocyanates, separately or mixed together;
(ii) mixing the dispersion of (a) with an isocyanate and a catalyst, mixing the dispersion of (b) with a polyol and a catalyst, or mixing the dispersion of (c) with a catalyst, to allow polymerization; and
(iii) isolating said polyurethane composite,
wherein the amount of water in said nanocrystalline cellulose is less than about 1% w/w.

### Claim 2 (depends on 1)

The process of claim 1, wherein the isocyanate is an aromatic isocyanate.

### Claim 3 (depends on 1)

The process of claim 1, wherein the isocyanate is an aliphatic isocyanate.

### Claim 4 (depends on 1)

The process of claim 1, wherein the isocyanate is selected from the group consisting of a polymeric diphenylmethane diisocyanates, diphenylmethane diisocyanate (MDI), toluene diisocyanate (TDI); 1,6-hexamethylene diisocyanate (HDI), 1-isocyanato-3-isocyanatomethyl-3,5,5-trimethyl-cyclohexane (IPDI), 4,4′-diisocyanato dicyclohexylmethane; and a mixture thereof.

### Claim 5 (depends on 1)

The process of claim 1, wherein the polyol for use in the process is comprising polyether polyols and polyester polyols.

### Claim 6 (depends on 1)

The process of claim 1, wherein the catalysts is an amine compound or metal complex.

### Claim 7 (depends on 1)

The process of claim 1, wherein the amount of nanocrystalline cellulose in said polyurethane composite is less than about 5% w/w.

### Claim 8 (depends on 1)

The process of claim 1, wherein the amount of nanocrystalline cellulose in said polyurethane composite is less than about 1% w/w.

### Claim 9

A method for modulating at least one property of a polyurethane, said method comprising:
(i) providing a dispersion by
(a) dispersing nanocrystalline cellulose into a polyol,
(b) dispersing nanocrystalline cellulose into an isocyanate, or
(c) dispersing nanocrystalline cellulose into a polyol and an isocyanate,
(ii) mixing the dispersion of (a) with an isocyanate and a catalyst, mixing the dispersion of (b) with a polyol and a catalyst, or mixing the dispersion of (c) with a catalyst, to form a mixture; and
(iii) polymerizing said mixture to provide said polyurethane,
wherein the amount of water in said nanocrystalline cellulose is less than about 1% w/w.

### Claim 10 (depends on 9)

The method of claim 9, wherein said property is one or more mechanical properties of the polyurethane selected from the group consisting of enhancement of elongation and tensile strength properties.

### Claim 11 (depends on 9)

The method of claim 9 wherein said property is one or more mechanical properties selected from the group consisting of scratch resistance, abrasion resistance, hardness, impact resistance and a combination thereof.

### Claim 12 (depends on 9)

The method of claim 9, wherein said polyurethane is a polyurethane which is used in elastomeric fibres, paints, solid polyurethane plastics thermoplastic and cast elastomers, adhesives and/or binders.