US4279809A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Stabilized polyolefin compositions
Assignee: El Paso Products Co
•
Filing: 1976-07-14
•
Granted: 1981-07-21
•
Expires: 1996-07-14
Abstract
Abstract Polyolefin resins are rendered stable against degradation caused by exposure to heat and oxygen in the presence of copper by the incorporation of a novel polymeric stabilizer functioning dually as an antioxidant and a chelating agent.
Inventors
- 👤 John L. H. Allan
- 👤 Arnold B. Finestone
- 👤 John J. Roderick
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-02 02:33
CPC Classifications
C; C08; C08G; C08G75/00; C08G75/02; C08G8/00; C08G8/04; C08G8/08; C08G8/18; C08L; C08L23/00; C08L23/02
Claims Analysis
Total Claims: 24
Claim 1
Independent Claim
211 words
The method of imparting stability to a mono-α-olefin polymer composition against copper-activated accelerated oxidative degradation, comprising: incorporating into a mono-α-olefin polymer resin from about 0.1 to about 10 percent by weight based on the weight of the composition of a polymeric compound as the sole copper deactivating agent, which polymeric compound has been prepared by: (a) reacting at least one para-substituted phenol of the formula: ##STR2## wherein R 1 is a C 3 -C 30 group selected from alkyl, cycloalkyl, alkaryl or aryl and R 2 is either hydrogen, a sulfonic acid group or a sulfonic acid salt group, with an aldehyde or ketone of the formula: ##STR3## wherein R 3 and R 4 independently from each other can be either hydrogen or a C 1 -C 36 group selected from alkyl, cycloalkyl, alkaryl or aryl, in a molar ratio of aldehyde or ketone to phenol of at least about 2:1 in the presence of an alkaline catalyst; and (b) reacting the product of step (a) with hydrogen sulfide or a polysulfide of the formula: HS(R.sub.5)SH wherein R 5 is a C 2 -C 20 group selected from alkylene, cycloalkylene, alkarylene or arylene, in about a 1:1 molar ratio of hydrogen sulfide or polysulfide to the phenol used in step (a).
Claim 2
Independent Claim
211 words
The method of imparting stability to a mono-α-olefin polymer composition against copper-activated accelerated oxidative degradation, comprising: incorporating into a mono-α-olefin polymer resin from about 0.1 to about 10 percent by weight based on the weight of the composition of a polymeric compound as the sole copper deactivating agent, which polymeric compound has been prepared by: (a) reacting at least one para-substituted phenol of the formula: ##STR2## wherein R 1 is a C 3 -C 30 group selected from alkyl, cycloalkyl, alkaryl or aryl and R 2 is either hydrogen, a sulfonic acid group or a sulfonic acid salt group, with an aldehyde or ketone of the formula: ##STR3## wherein R 3 and R 4 independently from each other can be either hydrogen or a C 1 -C 36 group selected from alkyl, cycloalkyl, alkaryl or aryl, in a molar ratio of aldehyde or ketone to phenol of at least about 2:1 in the presence of an alkaline catalyst; and (b) reacting the product of step (a) with hydrogen sulfide or a polysulfide of the formula: HS(R.sub.5)SH wherein R 5 is a C 2 -C 20 group selected from alkylene, cycloalkylene, alkarylene or arylene, in about a 1:1 molar ratio of hydrogen sulfide or polysulfide to the phenol used in step (a).
Claim 3
Dependent Claim
12 words
The method of claim 1 wherein R 1 is an alkyl group.
Claim 4
Dependent Claim
13 words
The method of claim 1 wherein R 1 is a tertiary alkyl group.
Claim 5
Dependent Claim
14 words
The method of claim 1 wherein R 3 and R 4 are both hydrogen.
Claim 6
Dependent Claim
27 words
The method of claim 1 wherein the mono-x-olefin polymer resin is selected from homo-polymers and copolymers of mono-x-olefins having 2 to 8 carbon atoms, and mixtures thereof.
Claim 7
Dependent Claim
16 words
The method of claim 1 wherein the product of step (a) is reacted with a polysulfide.
Claim 8
Dependent Claim
14 words
The method of claim 6 wherein R 5 is --CH 2 .CH 2 --.
Claim 9
Dependent Claim
24 words
The method of claim 1 wherein the polymeric compound is incorporated in an amount ranging from about 0.5 to about 5 percent by weight.
Claim 10
Dependent Claim
24 words
The method of claim 5 wherein the mono-x-olefin polymer resin is a polypropylene resin containing at least 60 percent by weight polymerized propylene groups.
Claim 11
Dependent Claim
26 words
The method of claim 9 wherein the polypropylene resin is an ethylene-propylene copolymer resin containing from about 2 to about 25 percent by weight polymerized ethylene.
Claim 12
Dependent Claim
23 words
The method of claim 10 wherein the ethylene-propylene copolymer resin is a copolymer containing from about 3 to about 15 percent polymerized ethylene.
Claim 13
Dependent Claim
10 words
The stabilized composition prepared by the method of claim 1.
Claim 14
Dependent Claim
206 words
A mono-α-olefin polymer composition stabilized against copper-activated accelerated oxidative degradation, which comprises: a mono-α-olefin polymer and from about 0.1 to about 10 percent by weight based on the total weight of the composition of a polymeric compound as the sole copper deactivating agent, which polymeric compound has been prepared by: (a) reacting at least one para-substituted phenol of the formula: ##STR4## wherein R 1 is a C 3 -C 30 group selected from alkyl, cycloalkyl, alkaryl or aryl and R 2 is either hydrogen, a sulfonic acid group or a sulfonic acid salt group; with an aldehyde or ketone of the formula: ##STR5## wherein R 3 and R 4 independently from each other can be either hydrogen or a C 1 -C 36 group selected from alkyl, cycloalkyl, alkaryl or aryl, in a molar ratio of aldehyde or ketone to phenol of at least about 2:1 in the presence of an alkaline catalyst; and (b) reacting the product of step (a) with hydrogen sulfide or a polysulfide of the formula: HS(R.sub.5)SH wherein R 5 is a C 2 -C 20 group selected from alkylene, cycloalkylene, alkarylene or arylene, in about a 1:1 molar ratio of hydrogen sulfide or polysulfide to the phenol used in step (a).
Claim 15
Dependent Claim
206 words
A mono-α-olefin polymer composition stabilized against copper-activated accelerated oxidative degradation, which comprises: a mono-α-olefin polymer and from about 0.1 to about 10 percent by weight based on the total weight of the composition of a polymeric compound as the sole copper deactivating agent, which polymeric compound has been prepared by: (a) reacting at least one para-substituted phenol of the formula: ##STR4## wherein R 1 is a C 3 -C 30 group selected from alkyl, cycloalkyl, alkaryl or aryl and R 2 is either hydrogen, a sulfonic acid group or a sulfonic acid salt group; with an aldehyde or ketone of the formula: ##STR5## wherein R 3 and R 4 independently from each other can be either hydrogen or a C 1 -C 36 group selected from alkyl, cycloalkyl, alkaryl or aryl, in a molar ratio of aldehyde or ketone to phenol of at least about 2:1 in the presence of an alkaline catalyst; and (b) reacting the product of step (a) with hydrogen sulfide or a polysulfide of the formula: HS(R.sub.5)SH wherein R 5 is a C 2 -C 20 group selected from alkylene, cycloalkylene, alkarylene or arylene, in about a 1:1 molar ratio of hydrogen sulfide or polysulfide to the phenol used in step (a).
Claim 16
Dependent Claim
12 words
The composition of claim 13 wherein R 1 is an alkyl group.
Claim 17
Dependent Claim
13 words
The composition of claim 13 wherein R 1 is a tertiary alkyl group.
Claim 18
Dependent Claim
14 words
The composition of claim 13 wherein R 3 and R 4 are both hydrogen.
Claim 19
Dependent Claim
27 words
The composition of claim 13 wherein the mono-x-olefin polymer resin is selected from homo-polymers and copolymers of mono-x-olefins having 2 to 8 carbon atoms, and mixtures thereof.
Claim 20
Dependent Claim
14 words
The composition of claim 13 wherein R 5 is --CH 2 .CH 2 --.
Claim 21
Dependent Claim
24 words
The composition of claim 13 wherein the polymeric compound is present in an amount ranging from about 0.5 to about 5 percent by weight.
Claim 22
Dependent Claim
24 words
The composition of claim 17 wherein the mono-x-olefin polymer resin is a polypropylene resin containing at least 60 percent by weight polymerized propylene groups.
Claim 23
Dependent Claim
26 words
The composition of claim 20 wherein the polypropylene resin is an ethylene-propylene copolymer resin containing from about 2 to about 25 percent by weight polymerized ethylene.
Claim 24
Dependent Claim
23 words
The composition of claim 21 wherein the ethylene-propylene copolymer resin is a copolymer containing from about 3 to about 15 percent polymerized ethylene.
References Cited (Backward Citations)
US2445736A
Cited
US2646415A
Cited
US3234176A
Cited
US3385818A
Cited
US3408327A
Cited
US3534119A
Cited
US3856728A
Cited
US3792014A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1984-07-20 | 1985-01-19 | 1985-07-21 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1988-07-20 | 1989-01-19 | 1989-07-21 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1992-07-20 | 1993-01-19 | 1993-07-21 | $7700.00 | Window Closed / Lapsed |