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US4025486A Expired / Lapsed US ⏱️ 0.0 years remaining

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
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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 11:47
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##

References Cited (Backward Citations)

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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

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