US3864324A
Expired / Lapsed
US
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Method for producing hydroxyl functional polymers
Assignee: Bridgestone Corp
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Filing: 1973-08-01
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Granted: 1975-02-04
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Expires: 1993-08-01
Abstract
Abstract Hydroxyl functional polymers having a molecular weight of about 500 to 50,000 are produced by subjecting some of the double bonds in a high polymer containing olefinically unsaturated double bonds to ozone-decomposition using ozone-containing gas and reducing the ozonides by means of a reducing agent having the general formula
Inventors
- 👤 Toshio Yukuta
- 👤 Takashi Ohashi
- 👤 Yoshiko Taniguchi
- 👤 Katsuhiko Arai
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-04 17:58
CPC Classifications
C; C08; C08C; C08C19/00; C08C19/30; C08C19/34; C08C19/04
Claims Analysis
Total Claims: 19
Claim 1
Independent Claim
64 words
A SOLUTION METHOD FOR PRODUCING HYDROXYL FUNCTIONAL POLYMERS HAVING A NUMBER AVERAGE MOLECULAR WEIGHT OF ABOUT 500 TO 50,000 AND CONTAINING HYDROXYL FUNCTIONAL GROUPS AT BOTH ENDS AND/OR ON THE SIDE CHAIN, WHICH COMPRISES OZONIZING SOME OF THE DOUBLE BONDS OF HOMOPOLYMERS OR COPOLYMERS HAVING A HIGH MOLECULAR WEIGHT AND CONTAINING OLEFINICALLY UNSATURATED DOUBLE BONDS REPRESENTTED BY AT LEAST ONE OF THE GENERAL FORMULAE
Claim 2
Dependent Claim
64 words
A SOLUTION METHOD FOR PRODUCING HYDROXYL FUNCTIONAL POLYMERS HAVING A NUMBER AVERAGE MOLECULAR WEIGHT OF ABOUT 500 TO 50,000 AND CONTAINING HYDROXYL FUNCTIONAL GROUPS AT BOTH ENDS AND/OR ON THE SIDE CHAIN, WHICH COMPRISES OZONIZING SOME OF THE DOUBLE BONDS OF HOMOPOLYMERS OR COPOLYMERS HAVING A HIGH MOLECULAR WEIGHT AND CONTAINING OLEFINICALLY UNSATURATED DOUBLE BONDS REPRESENTTED BY AT LEAST ONE OF THE GENERAL FORMULAE
Claim 3
Dependent Claim
35 words
A method as claimed in claim 1 wherein said homopolymer having a high molecular weight and containing the olefinically unsaturated double bonds in the molecule is selected from the group consisting of cis-1,4-polybutadiene and cis-1,4-polyisoprene.
Claim 4
Dependent Claim
15 words
A method as claimed in claim 1 wherein the ozonization temperature is 20*C to 30*C.
Claim 5
Dependent Claim
27 words
A method as claimed in claim 1 wherein sodium bis(2-methoxyethoxy)aluminum hydride is used in an amount of 1.2 to 2.0 equivalents based on equivalent of the ozonides.
Claim 6
Dependent Claim
21 words
A method as claimed in claim 1 wherein reducing the ozonide is effected at a temperature of 0*C to room temperature.
Claim 7
Dependent Claim
42 words
A method as claimed in claim 1 wherein said homopolymer or copolymer is dissolved in at least one solvent selected from the group consisting of halogenated hydrocrbons, linear ethers, cyclic ethers, aromatic hydrocarbons, linear paraffins and cyclic paraffins during said ozonizing step.
Claim 8
Dependent Claim
30 words
A method as claimed in claim 6 wherein said solvent is selected from the group consisting of chloroform, diethyl ether, tetrahydrofuran, dioxane, benzene, toluene, xylene, pentane, hexane, heptane and cyclohexane.
Claim 9
Dependent Claim
27 words
A method as claimed in claim 6 wherein the amount of said homopolymer or copolymer is between 0.1 g and 50 g per 100 ml of solvent.
Claim 10
Dependent Claim
26 words
A method as claimed in claim 8 wherein the amount of said homopolymer or copolymer is between 1 and 10 g per 100 ml of solvent.
Claim 11
Dependent Claim
32 words
A method as claimed in claim 1 wherein said reducing agent is added to said ozonides in a solvent which will not react with said agent and which dissolves said ozonides homogeneously.
Claim 12
Dependent Claim
26 words
A method as claimed in claim 10 wherein said solvent is selected from the group consisting of aromatic hydrocarbons, aliphatic ethers, cyclic ethers and cyclic hydrocarbons.
Claim 13
Dependent Claim
47 words
A method as claimed in claim 11 wherein said solvent is selected from the group consisting of benzene, toluene, xylene, dimethyl ether, diethyl ether, di-n-propyl ether, di-i-propyl ether, di-n-butyl ether, tetrahydrofuran, dioxane, ethylenE glycol dimethyl ether, diethylene glycol dimethyl ether, triethylene glycol dimethyl ether, cyclobutane and cyclohexane.
Claim 14
Dependent Claim
23 words
A method as claimed in claim 1 wherein said reducing step is carried out over a period of between 0.5 and 24 hours.
Claim 15
Dependent Claim
21 words
A method as claimed in claim 1 wherein said ozonizing step and said reducing step are carried out in benzene solution.
Claim 16
Dependent Claim
37 words
A method as claimed in claim 1 further comprising decomposing any excess of said reducing agent by adding water or a dilute solution of an acid to the reaction system after said reducing step has been completed.
Claim 17
Dependent Claim
21 words
A method as claimed in claim 1 further comprising recovering said hydroxyl functional polymers after said reducing step has been completed.
Claim 18
Dependent Claim
22 words
A method as claimed in claim 1 further comprising the step of masticating said homopolymer or copolymer prior to said ozonizing step.
Claim 19
Dependent Claim
23 words
A method as claimed in claim 1 wherein said carrier gas is selected from the group consisting of oxygen, nitrogen, air and argon.
References Cited (Backward Citations)
US3312744A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1978-02-03 | 1978-08-05 | 1979-02-04 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1982-02-03 | 1982-08-05 | 1983-02-04 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1986-02-03 | 1986-08-05 | 1987-02-04 | $7700.00 | Window Closed / Lapsed |