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US4025486A
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Hydroxyphenylalkyleneyl isocyanurate/pentaerythritol phosphite combinations as ultraviolet light stabilizers for polyolefins
Assignee: Goodrich Corp
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Filing: 1975-09-29
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Granted: 1977-05-24
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Expires: 1995-09-29
Abstract
Abstract Polyolefin polymers subject to degradation on exposure to ultraviolet light are efficiently stabilized using a combination of a hydroxyphenylalkyleneyl isocyanurate compound and a pentaerythritol phosphite compound. The stabilized compositions exhibit exceptional stability to UV light, better than that achieved using known combinations of phenolic and phosphorous-containing stabilizer compounds.
Inventors
- 👤 Jack Conrad Gilles
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-25 14:30
CPC Classifications
C; C08; C08K; C08K5/00; C08K5/16; C08K5/34; C08K5/3467; C08K5/3477; C08K5/3492; C08K5/34924
Claims Analysis
Total Claims: 16
Claim 1
Independent Claim
211 words
As a stabilizer for polyolefin polymers subject to degradation when exposed to ultraviolet light, a combination consisting essentially of (1) a hydroxyphenylalkyleneyl isocyanurate of the formula ##STR15## wherein R' is a hydroxyphenylalkyleneyl radical of the formula ##STR16## where m is 1 to 4, r 1 is an alkyl radical having 1 to 18 carbon atoms and is positioned immediately adjacent to the hydroxyl group on the ring; r 2 , r 3 , and r 4 are hydrogen or an alkyl radical containing 1 to 18 carbon atoms; and R" and R'" are hydrogen, an alkyl radical containing 1 to 18 carbon atoms, or are the same as R', and (2) a pentaerythritol phosphite compound selected from the group consisting of (a) compounds of the formula ##STR17## wherein R is selected from the group consisting of an aliphatic group containing 1 to about 20 carbon atoms, a cycloalkyl radical containing 5 to about 8 carbon atoms in the ring, and an aryl, alkaryl, or aralkyl group of 6 to about 14 carbon atoms in the group, (b) compounds of the formula ##STR18## wherein R is defined as above, and wherein the said hydroxyphenylalkyleneyl isocyanurate compound is used in a weight ratio of about 10:1 to 1:10 to the pentaerythritol phosphite compound.
Claim 2
Dependent Claim
211 words
As a stabilizer for polyolefin polymers subject to degradation when exposed to ultraviolet light, a combination consisting essentially of (1) a hydroxyphenylalkyleneyl isocyanurate of the formula ##STR15## wherein R' is a hydroxyphenylalkyleneyl radical of the formula ##STR16## where m is 1 to 4, r 1 is an alkyl radical having 1 to 18 carbon atoms and is positioned immediately adjacent to the hydroxyl group on the ring; r 2 , r 3 , and r 4 are hydrogen or an alkyl radical containing 1 to 18 carbon atoms; and R" and R'" are hydrogen, an alkyl radical containing 1 to 18 carbon atoms, or are the same as R', and (2) a pentaerythritol phosphite compound selected from the group consisting of (a) compounds of the formula ##STR17## wherein R is selected from the group consisting of an aliphatic group containing 1 to about 20 carbon atoms, a cycloalkyl radical containing 5 to about 8 carbon atoms in the ring, and an aryl, alkaryl, or aralkyl group of 6 to about 14 carbon atoms in the group, (b) compounds of the formula ##STR18## wherein R is defined as above, and wherein the said hydroxyphenylalkyleneyl isocyanurate compound is used in a weight ratio of about 10:1 to 1:10 to the pentaerythritol phosphite compound.
Claim 3
Dependent Claim
52 words
A combination of claim 1 where in (1) R" and R'" are equal to R', r 1 is a tertiary alkyl radical containing 4 to about 12 carbon atoms, r 2 is an alkyl radical containing 1 to about 12 carbon atoms, r 3 and r 4 are hydrogen, and m= 1.
Claim 4
Dependent Claim
17 words
A combination of claim 2 where (1) has the formula ##STR19## where n is 4 to 8.
Claim 5
Dependent Claim
26 words
A combination of claim 3 where in (2) R is an alkyl radical of 1 to about 20 carbon atoms, cyclohexyl, phenyl, or a benzyl radical.
Claim 6
Dependent Claim
25 words
The combination of claim 4 where (1) is 1,3,5-tris-(3,5-di-t-butyl-4-hydroxybenzyl)isocyanurate and (2) is ##STR20## where R is alkyl of about 6 to about 20 carbon atoms.
Claim 7
Dependent Claim
13 words
The combination of claim 4 where (1) is 1,3,5-tris-(3,5-di-t-butyl-4-hydroxybenzyl)isocyanurate and (2) is ##STR21##
Claim 8
Dependent Claim
209 words
A composition comprising (A) a polyolefin polymer and (B) as the only ultraviolet light stabilizer, a combination of (1) a hydroxyphenylalkyleneyl isocyanurate of the formula ##STR22## wherein R' is a hydroxyphenylalkyleneyl radical of the formula ##STR23## where m is 1 to 4, r 1 is an alkyl radical having 1 to 18 carbon atoms and is positioned immediately adjacent to the hydroxyl group on the ring; r 2 , r 3 , and r 4 are hydrogen or an alkyl radical containing 1 to 18 carbon atoms; and R" and R'" are hydrogen, an alkyl radical containing 1 to 18 carbon atoms, or are the same as R', and (2) a pentaerythritol phosphite compound selected from the group consisting of (a) compounds of the formula ##STR24## wherein R is selected from the group consisting of an aliphatic group containing 1 to about 20 carbon atoms, a cycloalkyl radical containing 5 to about 8 carbon atoms in the ring, and an aryl, alkaryl, or aralkyl group of 6 to about 14 carbon atoms in the group, (b) compounds of the formula ##STR25## wherein R is defined as above, and wherein the said hydroxyphenylisocyanurate compound is used in a weight ratio of about 10:1 to 1:10 to the pentaerythritol phosphite compound.
Claim 9
Dependent Claim
209 words
A composition comprising (A) a polyolefin polymer and (B) as the only ultraviolet light stabilizer, a combination of (1) a hydroxyphenylalkyleneyl isocyanurate of the formula ##STR22## wherein R' is a hydroxyphenylalkyleneyl radical of the formula ##STR23## where m is 1 to 4, r 1 is an alkyl radical having 1 to 18 carbon atoms and is positioned immediately adjacent to the hydroxyl group on the ring; r 2 , r 3 , and r 4 are hydrogen or an alkyl radical containing 1 to 18 carbon atoms; and R" and R'" are hydrogen, an alkyl radical containing 1 to 18 carbon atoms, or are the same as R', and (2) a pentaerythritol phosphite compound selected from the group consisting of (a) compounds of the formula ##STR24## wherein R is selected from the group consisting of an aliphatic group containing 1 to about 20 carbon atoms, a cycloalkyl radical containing 5 to about 8 carbon atoms in the ring, and an aryl, alkaryl, or aralkyl group of 6 to about 14 carbon atoms in the group, (b) compounds of the formula ##STR25## wherein R is defined as above, and wherein the said hydroxyphenylisocyanurate compound is used in a weight ratio of about 10:1 to 1:10 to the pentaerythritol phosphite compound.
Claim 10
Dependent Claim
59 words
A composition of claim 7 wherein (A) is a poly-α-monoolefin polymer, and in (B)(1), R" and R'" are the same as R', r 1 is a tertiary alkyl radical containing 4 to about 12 carbon atoms, r 2 is an alkyl radical containing 1 to about 12 carbon atoms, r 3 and r 4 are hydrogen, and m= 1.
Claim 11
Dependent Claim
31 words
A composition of claim 8 wherein (A) is a poly-α-monoolefin homopolymer and in (B)(2), R is an alkyl radical of 1 to about 20 carbon atoms, cyclohexyl, phenyl or benzyl radical.
Claim 12
Dependent Claim
10 words
A composition of claim 9 wherein (A) is a polypropylene.
Claim 13
Dependent Claim
17 words
A composition of claim 10 wherein (B)(1) has the formula ##STR26## where n is 4 to 8.
Claim 14
Dependent Claim
9 words
A composition of claim 11 wherein (B)(1) is 1,3,5-tris-(3,5-di-t-butyl-4-hydroxybenzyl)isocyanurate.
Claim 15
Dependent Claim
23 words
A composition of claim 12 wherein (B)(2) is the compound ##STR27## where R is alkyl of about 6 to about 20 carbon atoms.
Claim 16
Dependent Claim
11 words
A composition of claim 12 wherein (B)(2) is the compound ##STR28##
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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) | 1980-05-23 | 1980-11-22 | 1981-05-24 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1984-05-23 | 1984-11-22 | 1985-05-24 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1988-05-23 | 1988-11-22 | 1989-05-24 | $7700.00 | Window Closed / Lapsed |