IP Library Granted Patent US 8,916,065
Granted Patent B2
US 8,916,065 · App. 14/053,489 · Granted Dec 23, 2014

Phosphite compositions

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Quick Facts
Patent No.
US 8,916,065
App. No.
14/053,489
Granted
Dec 23, 2014
Kind
B2
Abstract

Solid phosphite compositions comprising tris(4-t-alkylphenyl)phosphites and selected hydroxyalkyl amines exhibit surprising performance compared with other phosphite stabilizers in the stabilization of polymers, such as polyolefins and the like, particularly in the prevention of color formation during high temperature processing or when exposed to certain gasses during storage, e.g., “gas fading”.

Claims (46)

1. A polymer stabilizing composition, comprising:

(i) a first component comprising one or more phosphite antioxidants,

wherein said one or more phosphite antioxidants comprise one or more solid tris(monoalkylaryl)phosphites, wherein the one or more solid tris(monoalkylaryl)phosphites is present in the composition at 100 wt % with respect to the total amount of alkylaryl phosphite present in the composition; and

(ii) a second component comprising an alkanolamine,

wherein the polymer stabilizing composition is a solid at 25° C.

2. The composition according to claim 1 , wherein

(a) the one or more phosphite antioxidants comprise one or more tris(phenyl)phosphite antioxidants alkylated at the ortho- or para-position relative to the phenoxy-phosphorus bond of tris(4-monoalkylphenyl)phosphite of formula (I):

wherein each R is independently selected from C 1 to C 5 straight or branched chain alkyl;

(b) the alkanolamine comprises one or more amines of formula (II):

wherein x is from 1 to 3; R 1 is selected from the group consisting of hydrogen, and straight or branched C 1 -C 6 alkyl, and R 2 is selected from the group consisting of straight or branched C 1 -C 30 alkyl, wherein the amine is present in an amount of from 0.01 to 5 wt % based on the total weight of phosphite antioxidants, and

the composition comprising (a) and (b) is a solid at 25° C.

3. The composition according to claim 2 , wherein R is selected from the group consisting of methyl, ethyl, propyl, 2-methylpropyl and 2,2-dimethylpropyl.

4. The composition according to claim 2 , wherein the at least one tris(4-monoalkylaryl)phosphite of formula (I) is selected from the group consisting of tris(4-t-butylphenyl)phosphate and tris(4-t-amylphenyl)phosphite.

5. The composition according to claim 2 , wherein in the amine (b) each R 1 is independently selected from the group consisting of hydrogen, straight or branched C 1 -C 3 alkyl and R 2 is a straight or branched C 8 -C 20 alkyl group.

6. The composition according to claim 5 wherein the amine is selected from the group consisting of triethanolamine, tripropanolamine, triisopropanolamine, octyl-bis(2-ethanol)amine, nonyl-bis(2-ethanol)amine, decyl-bis(2-ethanol)amine, undecyl-bis(2-ethanol)amine, dodecyl-bis(2-ethanol)amine, tridecyl-bis(2-ethanol)amine, tetradecyl-bis(2-ethanol)amine, pentadecyl-bis(2-ethanol)amine, hexadecyl-bis(2-ethanol)amine, heptadecyl-bis(2-ethanol)amine, octadecyl-bis(2-ethanol)amine, octyl-bis(2-propanol)amine, nonyl-bis(2-propanol)amine, decyl-bis(2-propanol)amine, undecyl-bis(2-propanol)amine, dodecyl-bis(2-propanol)amine, tridecyl-bis(2-propanol)amine, tetradecyl-bis(2-propanol)amine, pentadecyl-bis(2-propanol)amine, hexadecyl-bis(2-propanol)amine, heptadecyl-bis(2-propanol)amine, octadecyl-bis(2-propanol)amine, and isomers thereof.

7. The composition according to claim 6 wherein the amine (b) is selected from the group consisting of triethanolamine, tripropanolamine, triisopropanolamine,

8. The composition according to claim 2 , wherein the amine is present in an amount of from 0.1 to 3 wt % based on the total weight of phosphate antioxidants.

9. The composition of claim 1 , further comprising a polymer blended with or otherwise incorporating said polymer stabilizing composition, thereby generating a stabilized polymeric composition.

10. The composition of claim 9 , wherein the stabilized polymeric composition comprises from 0.01 to 10% of the polymer stabilizing composition.

11. The composition of claim 9 , wherein the at least one tris(monoalkylaryl)phosphite is selected from the group consisting of tris(4-t-butylphenyl)phosphite and tris(4-t-amylphenyl)phosphite,

wherein the alkanolamine is selected from the group consisting of triethanolamine, tripropanolamine and triisopropanolamine, and

wherein the alkanolamine is present in an amount of from 0.5 to 1.5 wt % based on the total weight of phosphite antioxidants present in the composition.

12. The composition of claim 9 , wherein the polymer comprises a homopolymer, co-polymer, plastomer, elastomer or blend comprising any two or more thereof.

13. A polymer stabilizing composition, comprising:

(i) a first component comprising at least one phosphite antioxidant,

wherein said at least one phosphite antioxidant comprises solid tris(monoalkylaryl)phosphite,

wherein the solid tris(monoalkylaryl)phosphite is present in the composition 100 wt % with respect to the total amount of alkylaryl phosphite present in the composition; and

(ii) a second component comprising an alkanolamine,

wherein the alkanolamine is present in an amount of from 0.1 to 3 wt % based on the total weight of the at least one phosphite antioxidant, and

wherein the polymer stabilizing composition is a solid at 25° C.

14. The polymer stabilizing composition according to claim 13 , wherein the solid tris(monoalkylaryl)phosphite comprises a tris(4-monoalkylphenyl)phosphite of formula (I):

wherein each R is independently selected from C 1 to C 5 straight or branched chain alkyl.

15. The polymer stabilizing composition according to claim 14 ,

further comprising a polymer of a type selected from the group consisting of homopolymers, co-polymers, plastomers, elastomers, and a blend comprising any two or more thereof, and

wherein the polymer is stabilized and exhibits improvements in one or more of melt flow index, yellowness index, and gas fade properties, as compared to a polymer in the absence of the polymer stabilizing composition.

16. A polymer stabilizing composition, comprising:

(i) a first component comprising at least one phosphite antioxidant,

wherein said at least one phosphite antioxidant comprises one or more tris(4-monoalkylphenyl)phosphite of formula (I):

wherein each R is independently selected from C 1 to C 5 straight or branched chain alkyl,

wherein the one or more tris(4-monoalkylphenyl)phosphate of formula (I) is present in the composition at 100 wt % with respect to the total amount of alkylaryl phosphate present in the composition; and

(ii) a second component comprising an alkanolamine,

wherein the alkanolamine is selected from the group consisting of triethanolamine, tripropanolamine and triisopropanolamine, and

wherein the polymer stabilizing composition is a solid at 25° C.

17. The polymer stabilizing composition of claim 16 , wherein the tris(4-monoalkylphenyl)phosphite is solid, and wherein each R in formula (I) is the same.

18. The polymer stabilizing composition of claim 16 , wherein the alkanolamine is triisopropanolamine.

19. The polymer stabilizing composition of claim 16 , wherein the tris(4-monoalkylphenyl)phosphite comprises one or more of tris(4-t-butylphenyl)phosphite and tris(4-t-amylphenyl)phosphite.

Assignments (11)
RELEASE OF SECURITY INTEREST Recorded Dec 30, 2025
From: ALTER DOMUS (US) LLC, AS COLLATERAL AGENT
To: SI GROUP, INC.
Reel/Frame 074136/0039 →
ASSIGNMENT OF SECURITY INTEREST IN PATENTS [REEL 068968/FRAME 0001] Recorded Dec 24, 2024
From: JPMORGAN CHASE BANK, N.A.
To: ALTER DOMUS (US) LLC
Reel/Frame 069770/0736 →
SECURITY INTEREST Recorded Sep 19, 2024
From: SI GROUP, INC.
To: JPMORGAN CHASE BANK, N.A., AS COLLATERAL AGENT
Reel/Frame 068968/0001 →
SECURITY INTEREST Recorded Sep 19, 2024
From: SI GROUP, INC.
To: JPMORGAN CHASE BANK, N.A., AS ADMINISTRATIVE AGENT
Reel/Frame 068968/0024 →
MERGER Recorded Feb 16, 2023
From: SI GROUP USA (USAA), LLC
To: SI GROUP, INC.
Reel/Frame 062719/0326 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 22, 2019
From: SI GROUP SWITZERLAND (CHAA) GMBH
To: SI GROUP USA (USAA), LLC
Reel/Frame 051091/0723 →
CHANGE OF NAME Recorded Nov 22, 2019
From: ADDIVANT SWITZERLAND GMBH
To: SI GROUP SWITZERLAND (CHAA) GMBH
Reel/Frame 051097/0724 →
RELEASE OF SECURITY INTEREST RECORDED AT REEL 037207 FRAME 0959 Recorded Oct 16, 2018
From: CERBERUS BUSINESS FINANCE, LLC
To: ADDIVANT USA, LLC
Reel/Frame 047775/0963 →
PATENT SECURITY AGREEMENT Recorded Dec 3, 2015
From: ADDIVANT USA, LLC
To: CERBERUS BUSINESS FINANCE, LLC, AS AGENT
Reel/Frame 037207/0959 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 28, 2014
From: SMITH, PETER
To: ADDIVANT SWITZERLAND GMBH
Reel/Frame 034053/0972 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 7, 2014
From: ZAHALKA, HAYDER; POWER, MAURICE; HILL, JONATHAN S.
To: ADDIVANT SWITZERLAND GMBH
Reel/Frame 031909/0871 →