US4088630A
Expired / Lapsed
US
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Cyclic acetals of polyols, their production and their use as non-discoloring anti-ozonants
Assignee: Bayer AG
•
Filing: 1976-10-26
•
Granted: 1978-05-09
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Expires: 1996-10-26
Abstract
Abstract Cyclic acetals which may be obtained by reacting tri- to hexa-ols with tetrahydrobenzaldehydes can be used as non-discoloring stabilizers for natural and/or synthetic rubber against ozone attack.
Inventors
- 👤 Ernst Roos
- 👤 Gunter Langner
- 👤 Theo Kempermann
- 👤 Wolfgang Redetzky
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-05 01:09
CPC Classifications
C; C07; C07D; C07D493/00; C07D493/02; C07D493/10; C07D317/00; C07D317/08; C07D317/10; C07D317/14; C07D317/18; C07D317/20; C07D317/22; C07D319/00; C07D319/04; C07D319/06; C08; C08K; C08K5/00; C08K5/04; C08K5/15; C08K5/156; Y; Y10; Y10S; Y10S524/00; Y10S524/925
Claims Analysis
Total Claims: 44
Claim 1
Independent Claim
76 words
A composition comprising a natural and/or synthetic rubber stabilized with an ozone resistant amount of a condensation product of at least one member selected from the group consisting of triols, tetraols, pentaols and hexaols and a compound of the formula ##STR8## wherein R is the same or different and is hydrogen or methyl, said condensation product being in a molar ratio of 1:1 to 1:3 and having all the aldehyde groups thereof present in acetalated form.
Claim 2
Dependent Claim
76 words
A composition comprising a natural and/or synthetic rubber stabilized with an ozone resistant amount of a condensation product of at least one member selected from the group consisting of triols, tetraols, pentaols and hexaols and a compound of the formula ##STR8## wherein R is the same or different and is hydrogen or methyl, said condensation product being in a molar ratio of 1:1 to 1:3 and having all the aldehyde groups thereof present in acetalated form.
Claim 3
Dependent Claim
30 words
The composition of claim 1 wherein the condensation product is the condensation product of a triol with said compound of said formula in a molar ratio of 1:1 or 1:1.5.
Claim 4
Dependent Claim
30 words
The composition of claim 1 wherein the condensation product is the condensation product of a tetraol with said compound of said formula in a molar ratio of 1:1 or 1:2.
Claim 5
Dependent Claim
32 words
The composition of claim 1 wherein the condensation product is the condensation product of a pentaol with said compound of said formula in a molar ratio of 1:1, 1:1.5, 1:2 or 1:2.5.
Claim 6
Dependent Claim
31 words
The composition of claim 1 wherein the condensation product is the condensation product of a hexaol with said compound of said formula in a molar ratio of 1:1, 1:2 or 1:3.
Claim 7
Dependent Claim
30 words
The composition of claim 1 wherein said at least one member is selected from the group consisting of glycerol, 1,1,1-trimethylolethane, 1,1,1-trimethylolpropane, 1,1,1-trimethylolbutane, 1,2,6-hexane triol, pentaerythritol, 2,2,6,6-tetramethylol cyclohexanol, sorbitol and mannitol.
Claim 8
Dependent Claim
39 words
The composition of claim 1 wherein said compound of said formula is selected from the group consisting of tetrahydro-Δ 3 -benzaldehyde; 3-methyl-, 4-methyl- and 3,4-dimethyl-tetrahydro-Δ 3 -benzaldehyde; 2,5-endomethylene tetrahydro-Δ 3 -benzaldehyde and 3-methyl-, 4-methyl- and 3,4-dimethyl-2,5-endomethylene tetrahydro-Δ 3 -benzaldehyde.
Claim 9
Dependent Claim
25 words
The composition of claim 1 wherein said condensation product is the condensation product of pentaerythritol and tetrahydro-Δ 3 -benzaldehyde in a molar ratio of 1:2.
Claim 10
Dependent Claim
19 words
The composition of claim 1 wherein said condensation product is the condensation product of pentaerythritol and 3-methyl-tetrahydro-Δ 3 -benzaldehyde.
Claim 11
Dependent Claim
19 words
The composition of claim 1 wherein said condensation product is the condensation product of pentaerythritol and 4-methyl-tetrahydro-Δ 3 -benzaldehyde.
Claim 12
Dependent Claim
20 words
The composition of claim 1 wherein said condensation product is the condensation product of pentaerythritol and endomethylene tetrahydro-Δ 3 -benzaldehyde.
Claim 13
Dependent Claim
44 words
The composition of claim 1 wherein said rubber is a polychloroprene rubber with a minimum polychloroprene content of 20% by weight and said condensation product is present in an amount of from 0.1 to 6.0% by weight based on the weight of said rubber.
Claim 14
Dependent Claim
34 words
The composition of claim 1 wherein said rubber is other than polychloroprene and said composition contains a hydrocarbon wax in a ratio by weight of wax to condensation product of between 0.25:1 and 2.5:1.
Claim 15
Dependent Claim
30 words
The composition of claim 13 wherein said condensation product and said wax are present in an amount of from 0.5 to 15% by weight based on the total rubber content.
Claim 16
Dependent Claim
30 words
The composition of claim 13 wherein said condensation product and said wax are present in an amount of from 1 to 10% by weight based on the total rubber content.
Claim 17
Dependent Claim
85 words
A composition comprising (a) a condensation product of at least one member selected from the group consisting of triols, tetraols, pentaols and hexaols and a compound of the formula ##STR9## wherein R is the same or different and is hydrogen or methyl, said condensation product being in a molar ratio of 1:1 to 1:3 and having all the aldehyde groups thereof present in acetalated form and (b) a hydrocarbon wax, the weight ratio of said wax to said condensation product being between 0.25:1 and 2.5:1.
Claim 18
Dependent Claim
85 words
A composition comprising (a) a condensation product of at least one member selected from the group consisting of triols, tetraols, pentaols and hexaols and a compound of the formula ##STR9## wherein R is the same or different and is hydrogen or methyl, said condensation product being in a molar ratio of 1:1 to 1:3 and having all the aldehyde groups thereof present in acetalated form and (b) a hydrocarbon wax, the weight ratio of said wax to said condensation product being between 0.25:1 and 2.5:1.
Claim 19
Dependent Claim
30 words
The composition of claim 16 wherein the condensation product is the condensation product of a triol with said compound of said formula in a molar ratio of 1:1 or 1:1.5.
Claim 20
Dependent Claim
30 words
The composition of claim 16 wherein the condensation product is the condensation product of a tetraol with said compound of said formula in a molar ratio of 1:1 or 1:2.
Claim 21
Dependent Claim
32 words
The composition of claim 16 wherein the condensation product is the condensation product of a pentaol with said compound of said formula in a molar ratio of 1:1, 1:1.5, 1:2 or 1:2.5.
Claim 22
Dependent Claim
31 words
The composition of claim 16 wherein the condensation product is the condensation product of a hexaol with said compound of said formula in a molar ratio of 1:1, 1:2 or 1:3.
Claim 23
Dependent Claim
30 words
The composition of claim 16 wherein said at least one member is selected from the group consisting of glycerol, 1,1,1-trimethylolethane, 1,1,1-trimethylolpropane, 1,1,1-trimethylolbutane, 1,2,6-hexane triol, pentaerythritol, 2,2,6,6-tetramethylol cyclohexanol, sorbitol and mannitol.
Claim 24
Dependent Claim
39 words
The composition of claim 16 wherein said compound of said formula is selected from the group consisting of tetrahydro-Δ 3 -benzaldehyde; 3-methyl-, 4-methyl- and 3,4-dimethyl-tetrahydro-Δ 3 -benzaldehyde; 3,5-endomethylene tetrahydro-Δ 3 -benzaldehyde and 3-methyl-, 4-methyl- and 3,4-dimethyl-2,5-endomethylene tetrahydro-Δ 3 -benzaldehyde.
Claim 25
Dependent Claim
25 words
The composition of claim 16 wherein said condensation product is the condensation product of pentaerythritol and tetrahydro-Δ 3 -benzaldehyde in a molar ratio of 1:2.
Claim 26
Dependent Claim
19 words
The composition of claim 16 wherein said condensation product is the condensation product of pentaerythritol and 3-methyl-tetrahydro-Δ 3 -benzaldehyde.
Claim 27
Dependent Claim
19 words
The composition of claim 16 wherein said condensation product is the condensation product of pentaerythritol and 4-methyl-tetrahydro-Δ 3 -benzaldehyde.
Claim 28
Dependent Claim
20 words
The composition of claim 16 wherein said condensation product is the condensation product of pentaerythritol and endomethylene tetrahydro-Δ 3 -benzaldehyde.
Claim 29
Dependent Claim
84 words
A process for stabilizing a natural and/or synthetic rubber against ozone attack which comprises adding to said rubber an ozone resistant amount of a condensation product of at least one member selected from the group consisting of triols, tetraols, pentaols, and hexaols and a compound of the formula ##STR10## wherein R is the same or different and is hydrogen or methyl, said condensation product being in a molar ratio of 1:1 to 1:3 and having all the aldehyde groups thereof present in acetalated form.
Claim 30
Dependent Claim
84 words
A process for stabilizing a natural and/or synthetic rubber against ozone attack which comprises adding to said rubber an ozone resistant amount of a condensation product of at least one member selected from the group consisting of triols, tetraols, pentaols, and hexaols and a compound of the formula ##STR10## wherein R is the same or different and is hydrogen or methyl, said condensation product being in a molar ratio of 1:1 to 1:3 and having all the aldehyde groups thereof present in acetalated form.
Claim 31
Dependent Claim
30 words
The process of claim 27 wherein said condensation product is the condensation product of a triol with said compound of said formula in a molar ratio of 1:1 or 1:1.5.
Claim 32
Dependent Claim
30 words
The process of claim 27 wherein said condensation product is the condensation product of a tetraol with said compound of said formula in a molar ratio of 1:1 or 1:2.
Claim 33
Dependent Claim
32 words
The process of claim 27 wherein said condensation product is the condensation product of a pentaol with said compound of said formula in a molar ratio of 1:1, 1:1.5, 1:2 or 1:2.5.
Claim 34
Dependent Claim
31 words
The process of claim 27 wherein the condensation product is the condensation product of a hexaol with said compound of said formula in a molar ratio of 1:1, 1:2 or 1:3.
Claim 35
Dependent Claim
30 words
The process of claim 27 wherein said at least one member is selected from the group consisting of glycerol, 1,1,1-trimethylolethane, 1,1,1-trimethylolpropane, 1,1,1-trimethylolbutane, 1,2,6-hexane triol, pentaerythritol, 2,2,6,6-tetramethylol cyclohexanol, sorbitol and mannitol.
Claim 36
Dependent Claim
39 words
The process of claim 27 wherein said compound of said formula is selected from the group consisting of tetrahydro-Δ 3 -benzaldehyde; 3-methyl-, 4-methyl- and 3,4-dimethyl-tetrahydro-Δ 3 -benzaldehyde; 2,5-endomethylene tetrahydro-Δ 3 -benzaldehyde and 3-methyl-, 4-methyl- and 3,4-dimethyl-2,5-endomethylene tetrahydro-Δ 3 -benzaldehyde.
Claim 37
Dependent Claim
25 words
The process of claim 27 wherein said condensation product is the condensation product of pentaerythritol and tetrahydro-Δ 3 -benzaldehyde in a molar ratio of 1:2.
Claim 38
Dependent Claim
19 words
The process of claim 27 wherein said condensation product is the condensation product of pentaerythritol and 3-methyl-tetrahydro-Δ 3 -benzaldehyde.
Claim 39
Dependent Claim
19 words
The process of claim 27 wherein said condensation product is the condensation product of pentaerythritol and 4-methyl-tetrahydro-Δ 3 -benzaldehyde.
Claim 40
Dependent Claim
20 words
The process of claim 27 wherein said condensation product is the condensation product of pentaerythritol and endomethylene tetrahydro-Δ 3 -benzaldehyde.
Claim 41
Dependent Claim
44 words
The process of claim 27 wherein said rubber is a polychloroprene rubber with a minimum polychloroprene content of 20% by weight and said condensation product is present in an amount of from 0.1 to 6.0% by weight based on the weight of said rubber.
Claim 42
Dependent Claim
34 words
The process of claim 27 wherein said rubber is other than polychloroprene and said composition contains a hydrocarbon wax in a ratio by weight of wax to condensation product of between 0.25:1 and 2.5:1.
Claim 43
Dependent Claim
30 words
The process of claim 27 wherein said condensation product and said wax are present in an amount of from 0.5 to 15% by weight based on the total rubber content.
Claim 44
Dependent Claim
30 words
The process of claim 27 wherein said condensation product and said wax are present in an amount of from 1 to 10% by weight based on the total rubber content.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1981-05-08 | 1981-11-07 | 1982-05-09 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1985-05-08 | 1985-11-07 | 1986-05-09 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1989-05-08 | 1989-11-07 | 1990-05-09 | $7700.00 | Window Closed / Lapsed |