# US 10,245,887 B2 · Methods relating to polyurethane foam-containing and degradable foam-containing tires, and degradable foam-containing tires

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- Number: US 10,245,887 B2
- Document ID: US10245887B2
- Status: Granted
- Kind: B2
- Application number: 15/746,716
- Filed: 2016-07-14
- Published: 2018-07-26
- Granted: 2019-04-02
- Earliest claimed: 2015-07-23
- Assignees: Bridgestrone Americas Tire Operations, LLC
- Applicants: Bridgestone Americas Tire Operations, LLC
- Inventors: Joshua P. Abell
- Web page: https://patentgrep.com/patent/US10245887B2

## CPC

- B60C 1/0016: {Compositions of the tread}
- B60C 1/00: Tyres characterised by the chemical composition or the physical arrangement or mixture of the composition
- B60C 1/0025: {Compositions of the sidewalls}
- B60C 5/002: {filled at least partially with foam material}
- B60C 7/1015: {using foam material}
- C08G 18/72: Polyisocyanates or polyisothiocyanates
- C08J 9/35: Composite foams, i.e. continuous macromolecular foams containing discontinuous cellular particles or fragments
- C08J 11/28: by treatment with organic compounds containing nitrogen, sulfur or phosphorus
- C08K 5/0033: {Additives activating the degradation of the macromolecular compound}
- C08K 5/49: Phosphorus-containing compounds {(C08K5/0091 takes precedence)}
- C08K 5/5317: Phosphonic compounds, e.g. R—P(:O)(OR')2
- C08K 5/5337: containing also halogens
- C08L 75/04: Polyurethanes
- B60C 2001/0091: {Compositions of non-inflatable or solid tyres}
- C08G 2110/0008: flexible
- C08G 2380/00: Tyres
- C08J 2375/04: Polyurethanes
- C08L 2203/14: used for foams
- Y02W 30/62: Plastics recycling; Rubber recycling
- B60C: VEHICLE TYRES; TYRE INFLATION; TYRE CHANGING; CONNECTING VALVES TO INFLATABLE ELASTIC BODIES IN GENERAL; DEVICES OR ARRANGEMENTS RELATED TO TYRES
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- 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)
- C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06)
- Y02W: CLIMATE CHANGE MITIGATION TECHNOLOGIES RELATED TO WASTEWATER TREATMENT OR WASTE MANAGEMENT

## Abstract

Disclosed herein are methods for degrading polyurethane foam from mounted polyurethane foam-containing tires, methods for separating a wheel from a mounted polyurethane foam-containing tire, methods for preparing a degradable foam-containing tire, and degradable foam-containing tires. The methods include applying a solution comprising at least one phosphorous oxoacid or an ester thereof to the polyurethane foam inside of a tire, incorporating a degradant comprising at least one phosphorous oxoacid or an ester thereof into the polyurethane foam, or both, and then heating to degrade the foam. Degradation of the foam allows for separation of the wheel from the rubber carcass of the tire.

## Claims

### Claim 1

A method for degrading polyurethane foam from inside of a mounted polyurethane foam-containing tire, the method comprising:
a. providing a solution comprising at least one phosphorous oxoacid or an ester thereof,
b. providing a mounted tire comprising a wheel and a rubber carcass and having polyurethane foam inside the rubber carcass,
c. applying the solution to the polyurethane foam inside the rubber carcass, and
d. heating to degrade the polyurethane foam.

### Claim 2 (depends on 1)

The method of claim 1, wherein the at least one phosphorous oxoacid or an ester thereof comprises an ester which is optionally halogenated.

### Claim 3 (depends on 2)

The method of claim 2, wherein the ester comprises at least one of:
a. a diester;
b. a monoester; or
c. a triester.

### Claim 4 (depends on 2)

The method of claim 2, wherein an ester functionality comprises an alkyl group each independently selected from C1-C41 optionally substituted with one or more halogen, or an aromatic or heteroaromatic group selected from C5-C53 optionally substituted with one or more halogen.

### Claim 5 (depends on 1)

The method of claim 1, wherein the at least one phosphorous oxoacid or ester thereof comprises dimethyl phosphonate, diethyl phosphonate, or a combination thereof.

### Claim 6 (depends on 1)

The method of claim 1, wherein the solution is applied to the polyurethane foam in a volume/volume ratio of about 10/1 to about 1/1, or an amount of degradant in the polyurethane foam is about 50 to about 300% by weight of the polyurethane foam.

### Claim 7 (depends on 1)

The method of claim 1, wherein the heating comprises at least one of:
a. heating at about 120 to about 250° C.; or
b. heating for about 0.5 to about 10 hours.

### Claim 8 (depends on 1)

The method of claim 1, further comprising exposing at least a portion of the polyurethane foam prior to applying the solution.

### Claim 9 (depends on 1)

The method of claim 1, wherein the mounted tire further comprises a tire stem and applying of the solution comprises adding the solution through the tire stem.

### Claim 10 (depends on 1)

The method of claim 1, wherein the solution comprising at least one phosphorous oxoacid or an ester thereof further comprises at least one catalyst, at least one surfactant, a combination thereof.

### Claim 11

A method for separating a wheel from a mounted polyurethane foam and degradant-containing tire by degrading the polyurethane foam, the method comprising:
a. providing a mounted tire comprising a wheel and a rubber carcass with polyurethane foam inside the rubber carcass wherein the polyurethane foam includes a degradant comprising at least one phosphorous oxoacid or an ester thereof,
b. optionally applying a solution comprising at least one phosphorous oxoacid or an ester thereof to the polyurethane foam inside the rubber carcass,
c. heating to degrade the polyurethane foam, and d. separating the wheel from the rubber carcass.

### Claim 12 (depends on 11)

The method of claim 11, wherein (b) is not optional and the at least one phosphorous oxoacid or an ester thereof comprises an ester which is optionally halogenated.

### Claim 13 (depends on 12)

The method of claim 12, wherein the ester comprises at least one of:
a. a diester;
b. a monoester; or
c. a triester.

### Claim 14 (depends on 12)

The method of claim 12, wherein an ester functionality comprises an alkyl group each independently selected from C1-C41 optionally substituted with one or more halogen, or an aromatic or heteroaromatic group selected from C5-C53 optionally substituted with one or more halogen.

### Claim 15 (depends on 11)

The method of claim 11, wherein (b) is not optional and the at least one phosphorous oxoacid or ester thereof comprises dimethyl phosphonate, diethyl phosphonate, or a combination thereof.

### Claim 16 (depends on 11)

The method of claim 11, wherein (b) is not optional and the solution is applied to the polyurethane foam in a volume/volume ratio of about 10/1 to about 1/1, or the amount of degradant in the polyurethane foam is about 50 to about 300% by weight of the polyurethane foam.

### Claim 17 (depends on 11)

The method of claim 11, wherein the heating comprises at least one of:
a. heating at about 120 to about 250° C.; or
b. heating for about 0.5 to about 10 hours.

### Claim 18 (depends on 11)

The method of claim 11, wherein (b) is not optional and the solution comprising at least one phosphorous oxoacid or an ester thereof further comprises at least one catalyst, at least one surfactant, a combination thereof.

### Claim 19 (depends on 1)

The method of claim 1, wherein the polyurethane foam of (b) comprises a combination of
a. 50-120 parts of at least one di- or polyisocyanate,
b. 100 parts of at least one polyol, and
c. 5-200 parts of a degradant comprising at least one phosphorous oxoacid or an ester thereof.

### Claim 20 (depends on 11)

The method of claim 11, wherein the polyurethane foam of (a) includes 50-120 parts of the at least one di- or polyisocyanate and 5-200 parts of the degradant comprising at least one phosphorous oxoacid or an ester thereof, and further comprises 100 parts of least one polyol.