# US 4,399,852 A · Application of ambient temperature cured polymers or prepolymers to a cured elastomer

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- Number: US 4,399,852 A
- Document ID: US4399852A
- Status: Granted
- Kind: A
- Application number: 06/316,023
- Filed: 1981-10-28
- Granted: 1983-08-23
- Earliest claimed: 1979-09-10
- Assignees: The Firestone Tire & Rubber Company
- Inventors: Walter R. Hausch
- Web page: https://patentgrep.com/patent/US4399852A

## CPC

- B29D 30/54: Retreading
- B29C 73/02: using liquid or paste-like material (B29C73/16 takes precedence)
- B29C 73/163: {Sealing compositions or agents, e.g. combined with propellant agents}
- B29D 2030/544: {Applying an intermediate adhesive layer, e.g. cement or cushioning element between carcass and tread}
- B29L 2023/005: {Hoses, i.e. flexible}
- B29L 2030/00: Pneumatic or solid tyres or parts thereof {(conveyor belts B29L2031/7092; drive belts B29L2031/7094; fourdrinier belts B29L2031/733)}
- B29L 2031/7092: {Conveyor belts}
- Y10S 152/12: White sidewalls
- Y10T 428/1386: Natural or synthetic rubber or rubber-like compound containing
- Y10T 428/31569: Next to natural rubber
- Y10T 428/3158: Halide monomer type [polyvinyl chloride, etc.]
- Y10T 428/31583: Nitrile monomer type [polyacrylonitrile, etc.]
- Y10T 428/31587: Hydrocarbon polymer [polyethylene, polybutadiene, etc.]
- B29D: PRODUCING PARTICULAR ARTICLES FROM PLASTICS OR FROM SUBSTANCES IN A PLASTIC STATE (making granules B29B9/00; making preforms B29B11/00)
- B29C: SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING (making preforms B29B11/00; making laminated products by combining previously unconnected layers which become one product whose layers will remain together B32B37/00 - B32B41/00)
- B29L: INDEXING SCHEME ASSOCIATED WITH SUBCLASS B29C, RELATING TO PARTICULAR ARTICLES
- Y10S: TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10T: TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION

## Abstract

A process and composition for applying and bonding a curable polymer or prepolymer, for example, an amine curable polymer or prepolymer, at ambient temperatures to the surface of a cured elastomer substrate. The elastomer article or substrate is treated with an organic oxidant such as one selected, for example, from the group consisting of N-halosulfonamides, N-halohydantoins, N-haloamides, N-haloimides, and the various isomers of mono-, di-, and trichloroisocyanuric acid. A composition of a curable polymer or prepolymer is prepared with a curing agent. To the curing agent and curable polymer or prepolymer composition is added a polar solvent which is mixed with the resulting blend or mixture and added to the treated elastomer surface; said polymer or prepolymer cures at ambient temperature and becomes bonded to said elastomer. The application is relatively easy, since the entire mixture is a liquid and can be applied in situ. The invention is particularly suitable for repairing various damaged elastomer articles such as tires (especially off-the-road), conveyor belts, hoses, preparation of caulking or sealing compounds, and especially in bonding tire lugs or tire treads to a tire carcass.

## Claims

### Claim 1

The process of repairing a cured elastomer tire substrate having an opening in its external surface, comprising the steps of:
cleaning the surface of said opening, applying, from a liquid system, at least one treating agent layer, said treating agent layer selected from the group consisting of an N-halohydantoin, an N-haloamide, and an N-haloimide, said treating agent layer effectively bonding to the surface of said opening, and
filling said opening with a liquid system containing an amine curable polymer or a prepolymer in a polar solvent and an amine curing agent, said amine curable polymer or prepolymer effectively bonding to said treating agent layer at ambient temperature.

### Claim 2 (depends on 1)

A process of repairing a cured elastomer tire according to claim 1, wherein said opening surface is cleaned with acetone,
said treating layer is applied as a solution of trichlorocyanuric acid, and
said amine curable polymer or prepolymer liquid system is polytetramethylene ether glycol, containing about 2.8 percent isocyanate end group by weight, in acetone as polar solvent; said curing agent is a complex of 4,4'-methylene dianiline with sodium chloride salt in a 50 percent by weight solution of tetraethylene glycol bis-2-ethyl hexoate.

### Claim 3 (depends on 1)

A process for repairing a cured elastomer tire according to claim 1, wherein said liquid treating agent is selected from the group consisting of monochloroisocyanuric acid, dichloroisocyanuric acid, trichloroisocyanuric acid, and combinations thereof,
said amine curable polymer or prepolymer is a urethane polymer or prepolymer, wherein said amine curing agent is selected from the group consisting of a complex of 4,4'-methylene dianiline and a salt, said salt being selected from the group consisting of sodium chloride, sodium bromide, sodium iodide, sodium nitrite, lithium chloride, lithium bromide, lithium iodide, lithium nitrite, and sodium cyanide, the ratio of said dianiline to said salt in said complex being 3 moles to 1 mole, the equivalent amount of said curing agent based upon said prepolymer or polymer ranging from about 0.85 to about 1.15 moles,
the amount of said polar solvent ranging from about 2 to about 40 parts per 100 parts of said urethane polymer or said prepolymer,
mixing said solvent, said urethane polymer or prepolymer, and said amine curing agent and applying said mixture to said opening to fill said opening, and
curing at an ambient temperature of from about 10.degree. C. to about 50.degree. C.

### Claim 4

The process of bonding a tread lug laminate to a cured elastomer tire substrate, comprising the steps of:
cleaning the surface of said cured elastomer tire substrate,
applying from a liquid system, at least one treating agent layer, said treating agent layer selected from the group consisting of a N-halohydantoin, an N-haloamide, and an N-haloimide, said treating agent layer effectively bonded to said substrate surface, and
applying to said substrate, in the form of a tread lug, a liquid system containing an amine curable polymer or a prepolymer in a polar solvent and an amine acuring agent, said amine curable polymer or prepolymer effectively bonding to said treating agent layer at ambient temperatures to form a tread lug.

### Claim 5 (depends on 4)

A process of bonding a tread lug laminate to a cured elastomer tire substrate, according to claim 4, wherein
said liquid treating agent is selected from the group consisting of monochloroisocyanuric acid, dichloroisocyanuric acid, trichloroisocyanuric acid, and combinations thereof,
said amine curable polymer or prepolymer is a urethane polymer or prepolymer, wherein said amine curing agent is selected from the group consisting of a complex of 4,4'-methylene dianiline and a salt, said salt being selected from the group consisting of sodium chloride, sodium bromide, sodium iodide, sodium nitrite, lithium chloride, lithium bromide, lithium iodide, lithium nitrite, and sodium cyanide, the ratio of said dianiline to said salt in said complex being 3 moles to 1 mole, the equivalent amount of said curing agent based upon said prepolymer or polymer ranging from about 0.85 to about 1.15 moles,
the amount of said polar solvent ranging from about 2 to about 40 parts per 100 parts of said urethane polymer or said prepolymer,
mixing said solvent, said urethane polymer or prepolymer, and said amine curing agent and applying said mixture to said opening to fill said opening, and
curing at an ambient temperature of from about 10.degree. C. to about 50.degree. C.

### Claim 6

A process of bonding a retread to a cured elastomer tire substrate, comprising the steps of:
cleaning the surface of said elastomer tire substrate,
bonding, from a liquid system, at least one treating agent layer, said treating agent layer selected from the group consisting of an N-halohydantoin, an N-haloamide, and an N-haloimide, said treating layer effectively bonding to said tire substrate surface, and
bonding to said tire, in the form of a retread, a liquid system containing an amine curable polymer or prepolymer in a polar solvent and an amine curing agent, said amine curable polymer or prepolymer effectively bonding to said treating agent layer of said tire substrate at ambient temperature.

### Claim 7 (depends on 6)

A process of bonding a retread to a cured elastomer tire substrate, according to claim 6, wherein said liquid treating agent is selected from the group consisting of monochloroisocyanuric acid, dichloroisocyanuric acid, trichloroisocyanuric acid, and combinations thereof,
said amine curable polymer or prepolymer is a urethane polymer or prepolymer, wherein said amine curing agent is a complex of 4,4'-methylene dianiline and a salt, said salt being selected from the group consisting of sodium chloride, sodium bromide, sodium iodide, sodium nitrite, lithium chloride, lithium bromide, lithium iodide, lithium nitrite, and sodium cyanide, the ratio of said dianiline to said salt in said complex being 3 moles to 1 mole, the equivalent amount of said curing agent based upon said prepolymer or polymer ranging from about 0.85 to about 1.15 moles,
the amount of said polar solvent ranging from about 2 to about 40 parts per 100 parts of said polymer or said prepolymer,
mixing said solvent, said polymer or prepolymer, and said amine curing agent, and applying said mixture to said tire in the form of a retread, and
curing at an ambient temperature of from about 10.degree. C. to about 50.degree. C. so that a retreaded tire is formed.

### Claim 8

The process of repairing a cured elastomer radiator hose substrate having a cavity in its external surface, comprising the steps of:
cleaning the surface of said cavity, applying, from a liquid system, at least one treating agent, said treating agent layer selected from the group consisting of an N-halohydantoin, an N-haloamide, and an N-haloimide, said treating layer effectively bonding to said tire substrate surface, and
filling said cavity with a liquid system containing an amine curable polymer or a prepolymer in a polar solvent and an amine curing agent, said amine curable polymer or prepolymer effectively bonding to said treating agent layer at ambient temperature.

### Claim 9 (depends on 8)

A process of repairing a cured elastomer radiator hose substrate according to claim 8, wherein said liquid treating agent is selected from the group consisting of monochloroisocyanuric acid, dichloroisocyanuric acid, trichloroisocyanuric acid, and combinations thereof,
said amine curable polymer or prepolymer is a urethane polymer or prepolymer, wherein said amine curing agent is a complex of 4,4'-methylene dianiline and a salt, said salt being selected from the group consisting of sodium chloride, sodium bromide, sodium iodide, sodium nitrite, lithium chloride, lithium bromide, lithium iodide, lithium nitrite, and sodium cyanide, the ratio of said dianiline to said salt in said complex being 3 moles to 1 mole, the equivalent amount of said curing agent based upon said prepolymer or polymer ranging from about 85 to about 1.15 moles,
from about 2 to about 40 parts of a polar solvent per 100 parts of said polymer or prepolymer,
mixing said solvent, said polymer or said prepolymer, and said curing agent, and applying said mixture to said cavity, and
curing at an ambient temperature of from about 10.degree. C. to about 50.degree. C.

### Claim 10

The process of repairing an elastomer conveyor belt substrate having an opening in its external surface, comprising the steps of:
cleaning the surface of said cavity, applying, from a liquid system, at least one treating agent, said treating agent layer selected from the group consisting of an N-halohydantoin, an N-haloamide, and an N-haloimide, said treating layer effectively bonding to said tire substrate surface, and
filling said cavity with a liquid system containing an amine curable polymer or a prepolymer in a polar solvent and an amine curing agent, said amine curable polymer or prepolymer effectively bonding to said treating agent layer at ambient temperature.

### Claim 11 (depends on 10)

A process of repairing an elastomer conveyor belt substrate having an opening in its external surface according to claim 10, wherein said liquid treating agent is selected from the group consisting of monochloroisocyanuric acid, dichloroisocyanuric acid, trichloroisocyanuric acid, and combinations thereof,
said amine curable polymer or prepolymer is a urethane polymer or prepolymer, wherein said amine curing agent is a complex of 4,4'-methylene dianiline and a salt, said salt being selected from the group consisting of sodium chloride, sodium bromide, sodium iodide, sodium nitrite, lithium chloride, lithium bromide, lithium iodide, lithium nitrite, and sodium cyanide, the ratio of said dianiline to said salt in said complex being 3 moles to 1 mole, the equivalent amount of said curing agent based upon said prepolymer or polymer ranging from about 0.85 to about 1.15 moles,
from about 2 to about 40 parts of a polar solvent per 100 parts of said polymer or prepolymer,
mixing said solvent, said polymer or said prepolymer, and said curing agent, and applying said mixture to said opening, and
curing at an ambient temperature of from about 10.degree. C. to about 50.degree. C.

### Claim 12

The process of repairing a composite cured elastomer substrate having an opening in its external surface, comprising the steps of:
cleaning the surface of said cavity, applying, from a liquid system, at least one treating agent, said treating agent layer selected from the group consisting of an N-halohydantoin, an N-haloamide, and an N-haloimide, said treating layer effectively bonding to said tire substrate surface, and
filling said cavity with a liquid system containing an amine curable polymer or a prepolymer in a polar solvent and an amine curing agent, said amine curable polymer or prepolymer effectively bonding to said treating agent layer at ambient temperature.

### Claim 13 (depends on 12)

A process of repairing a composite cured elastomer substrate according to claim 12, wherein said liquid treating agent is selected from the group consisting of monochloroisocyanuric acid, dichloroisocyanuric acid, trichloroisocyanuric acid, and combinations thereof, and
said amine curable polymer or prepolymer is a urethane polymer or prepolymer, wherein said amine curing agent is a complex of 4,4'-methylene dianiline and a salt, said salt being selected from the group consisting of sodium chloride, sodium bromide, sodium iodide, sodium nitrite, lithium chloride, lithium bromide, lithium iodide, lithium nitrite, and sodium cyanide, the ratio of said dianiline to said salt in said complex being 3 moles to 1 mole, the equivalent amount of said curing agent based upon said prepolymer or polymer ranging from about 0.85 to about 1.15 moles,
the amount of said polar solvent ranging from about 2 to about 40 parts per 100 parts of said polymer or said prepolymer,
mixing said solvent, said polymer or prepolymer, and said amine curing agent and applying said mixture to said elastomer substrate, and
curing at an ambient temperature of from about 10.degree. C. to about 50.degree. C.