IP Library Granted Patent US 8,962,718
Granted Patent B2
US 8,962,718 · App. 13/093,329 · Granted Feb 24, 2015

Chlorine-resistant crosslinkable polyolefin compositions and articles made therefrom

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Quick Facts
Patent No.
US 8,962,718
App. No.
13/093,329
Granted
Feb 24, 2015
Kind
B2
Abstract

The present invention relates to chlorine resistant crosslinkable silane-containing polyolefin compositions and stabilizer masterbatch compositions, their preparation, and articles made therefrom. These crosslinkable silane-containing compositions contain a mixture of antioxidants, light absorbers and stabilizers that provide resistance to the levels of chlorine used in potable water and to light, thereby extending the useful life of said articles made therefrom, such as potable water pipes and valves, bottles, tanks, and the like.

Claims (85)

1. A crosslinkable silane-containing polyolefin composition comprising:

(a) a polyolefin containing at least one hydrolysable silyl group;

(b) a sterically hindered phenol antioxidant;

(c) a phosphite processing stabilizer;

(d) a sterically hindered amine light stabilizer;

(e) a substituted benzotriazol ultraviolet light absorber;

(f) a curing catalyst; and

(g) silicone-polyether copolymer is selected from the group consisting of (CH 3 ) 3 SiO—[Si(CH 3 ) 2 O—] 20 [SiCH 3 ((CH 2 ) 3 O(CH 2 CH 2 O) 10 (CH 2 CH(CH 3 )O) 20 H)O—] 3 Si(CH 3 ) 3 ; (CH 3 ) 3 SiO—[Si(CH 3 ) 2 O—] 50 [SiCH 3 ((CH 2 ) 3 O(CH 2 CH 2 O) 10 (CH 2 CH(CH 3 )O) 20 H)O—] 8 Si(CH 3 ) 3 ; (CH 3 ) 3 SiO—[Si(CH 3 ) 2 O—] 75 [SiCH 3 ((CH 2 ) 3 O(CH 2 CH 2 O) 10 (CH 2 CH(CH 3 )O) 10 H)O—] 8 Si(CH 3 ) 3 ; (CH 3 ) 3 SiO—[Si(CH 3 ) 2 O—] 50 [SiCH 3 ((CH 2 ) 3 O(CH 2 CH 2 O) 5 H)O—] 5 Si(CH 3 ) 3 ; (CH 3 ) 3 SiO—[Si(CH 3 ) 2 O—] 50 [SiCH 3 ((CH 2 ) 3 O(CH 2 CH 2 O) 7 H)O—] 5 Si(CH 3 ) 3 ; (CH 3 ) 3 SiO—[Si(CH 3 ) 2 O—] 50 [SiCH 3 ((CH 2 ) 3 O(CH 2 CH 2 O) 10 H)O—] 5 Si(CH 3 ) 3 ; (CH 3 ) 3 SiO—[Si(CH 3 ) 2 O—] 70 [SiCH 3 ((CH 2 ) 3 O(CH 2 CH 2 O) 5 H)O—] 5 Si(CH 3 ) 3 ; (CH 3 ) 3 SiO—[Si(CH 3 ) 2 O—] 70 [SiCH 3 ((CH 2 ) 3 O(CH 2 CH 2 O) 7 H)O—] 5 Si(CH 3 ) 3 ; (CH 3 ) 3 SiO—[Si(CH 3 ) 2 O—] 70 [SiCH 3 ((CH 2 ) 3 O(CH 2 CH 2 O) 10 H)O—] 5 Si(CH 3 ) 3 ; (CH 3 ) 3 SiO—[Si(CH 3 ) 2 O—] 75 [SiCH 3 ((CH 2 ) 3 O(CH 2 CH 2 O) 7 H)O—] 5 Si(CH 3 ) 3 ; (CH 3 ) 3 SiO—[Si(CH 3 ) 2 O—] 75 [SiCH 3 ((CH 2 ) 3 O(CH 2 CH 2 O) 10 H)O—] 5 Si(CH 3 ) 3 ; (CH 3 ) 3 SiO—[Si(CH 3 ) 2 O—] 75 [SiCH 3 ((CH 2 ) 3 O(CH 2 CH 2 O) 5 H)O—] 5 Si(CH 3 ) 3 ; (CH 3 ) 3 SiO—[Si(CH 3 ) 2 O—] 75 [SiCH 3 ((CH 2 ) 3 O(CH 2 CH 2 O) 7 H)O—] 5 Si(CH 3 ) 3 ; (CH 3 ) 3 SiO—[Si(CH 3 ) 2 O—] 75 [SiCH 3 ((CH 2 ) 3 O(CH 2 CH 2 O) 10 H)O—] 5 Si(CH 3 ) 3 ; (CH 3 ) 3 SiO—[Si(CH 3 ) 2 O—] 75 [SiCH 3 ((CH 2 ) 3 O(CH 2 CH 2 O) 7 H)O—] 10 Si(CH 3 ) 3 ; (CH 3 ) 3 SiO—[Si(CH 3 ) 2 O—] 75 [SiCH 3 ((CH 2 ) 3 O(CH 2 CH 2 O) 7 H)O—] 10 Si(CH 3 ) 3 ; (CH 3 ) 3 SiO—[Si(CH 3 ) 2 O—] 75 [SiCH 3 ((CH 2 ) 3 O(CH 2 CH 2 O) 10 H)O—] 10 Si(CH 3 ) 3 ; (CH 3 ) 3 SiO—[Si(CH 3 ) 2 O—] 75 [SiCH 3 ((CH 2 ) 3 O(CH 2 CH 2 O) 20 H)O—] 10 Si(CH 3 ) 3 ; (CH 3 ) 3 SiO—[Si(CH 3 ) 2 O—] 75 [SiCH 3 ((CH 2 ) 3 O(CH 2 CH 2 O) 22 (CH 2 CH(CH 3 )O) 8 H)O—] 10 Si(CH 3 ) 3 ; (CH 3 ) 3 SiO—[Si(CH 3 ) 2 O—] 100 [SiCH 3 ((CH 2 ) 3 O(CH 2 CH 2 O) 10 (CH 2 CH(CH 3 )O) 20 H)O—] 15 Si(CH 3 ) 3 ; (CH 3 ) 3 SiO—[Si(CH 3 ) 2 O—] 50 [SiCH 3 ((CH 2 ) 3 O(CH 2 CH 2 O) 10 (CH 2 CH(CH 3 )O) 10 CH 3 )O—] 5 Si(CH 3 ) 3 ; (CH 3 ) 3 SiO—[Si(CH 3 ) 2 O—] 70 [SiCH 3 ((CH 2 ) 3 O(CH 2 CH 2 O) 35 (CH 2 CH(CH 3 )O) 40 CH 3 )O—] 5 Si(CH 3 ) 3 ; (CH 3 ) 3 SiO—[Si(CH 3 ) 2 O—] 70 [SiCH 3 ((CH 2 ) 3 O(CH 2 CH 2 O) 15 (CH 2 CH(CH 3 )O) 15 CH 3 )O—] 5 Si(CH 3 ) 3 ; (CH 3 ) 3 SiO—[Si(CH 3 ) 2 O—] 75 [SiCH 3 ((CH 2 ) 3 O(CH 2 CH 2 O) 15 (CH 2 CH(CH 3 )O) 15 CH 3 )O—] 5 Si(CH 3 ) 3 ; (CH 3 ) 3 SiO—[Si(CH 3 ) 2 O—] 100 [SiCH 3 ((CH 2 ) 3 O(CH 2 CH 2 O) 15 (CH 2 CH(CH 3 )O) 20 CH 3 )O—] 15 Si(CH 3 ) 3 ; (CH 3 ) 3 SiO—[Si(CH 3 ) 2 O—] 75 [SiCH 3 ((CH 2 ) 3 O(CH 2 CH 2 O) 15 (CH 2 CH(CH 3 )O) 15 COCH 3 )O—] 5 Si(CH 3 ) 3 ; (CH 3 ) 3 SiO—[Si(CH 3 ) 2 O—] 75 [SiCH 3 ((CH 2 ) 3 O(CH 2 CH 2 O) 13 (CH 2 CH(CH 3 )O) 15 H)O—] 4 —[SiCH 3 ((CH 2 ) 3 O(CH 2 CH 2 O) 35 (CH 2 CH(CH 3 )O) 40 H)O—]Si(CH 3 ) 3 ; and mixtures thereof.

2. The crosslinkable silane-containing polyolefin composition of claim 1 further comprising a metal deactivator of the general formula (XII):

wherein:

each occurrence of R 27 is independently a monovalent alkyl, aryl or aralkyl group containing from 1 to 16 carbon atoms; and

each occurrence of R 28 is independently a hydrogen atom or a monovalent alkyl, aryl or aralkyl group containing from 1 to 16 carbon atoms.

3. The crosslinkable silane-containing polyolefin composition of claim 2 wherein the metal deactivator is selected from the group consisting of 1,2-bis(3,5-di-tert-butyl-4-hydroxyhydrocinnamoyl)hydrazine, 2,2′-oxamidobis(ethyl-3-(3,5-di-tert-4-hydroxyphenyl)-propionate, tris[2-tert-butyl-4-(5-tert-butyl-4-hydroxy-2-methylphenyl)sulfanyl-5-methylphenyl]phosphate, 2-[[2-[2-[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyloxy]ethylamino]-2-oxoacetyl]amino]ethyl 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate, and mixtures thereof.

4. The crosslinkable silane-containing polyolefin composition of claim 1 , wherein the composition comprises:

90 to 99.95 weight percent of the polyolefin containing at least one hydrolysable silyl group (a);

0.01 to 4 weight percent of the sterically hindered phenol antioxidant (b);

0.01 to 2 weight percent of the phosphite processing stabilizer (c);

0.01 to 2 weight percent of the sterically hindered amine light stabilizer (d);

0.01 to 2 weight percent of the substituted benzotriazol ultraviolet light absorber (e); and

0.01 to 2 weight percent of the curing catalyst (f);

wherein said weight percents are based upon the total weight of components (a) through (f).

5. The crosslinkable silane-containing polyolefin composition of claim 4 , comprising:

95 to 99.1 weight percent of the polyolefin containing at least one hydrolysable silyl group (a);

3 to 1 weight percent of the sterically hindered phenol antioxidant (b);

0.05 to 0.15 weight percent of the phosphite processing stabilizer (c);

0.05 to 0.15 weight percent of the sterically hindered amine light stabilizer (d);

0.05 to 0.5 weight percent of the substituted benzotriazol ultraviolet light absorber (e);

and

0.02 to 1.5 weight percent of the curing catalyst (f);

wherein said weight percents are based upon the total weight of components (a) through (f).

6. The crosslinkable silane-containing polyolefin composition of claim 1 wherein the polyolefin containing at least one hydrolysable silyl group (a) comprises at least one repeat unit of Formula (I):

[—CH 2 C(−)(R 1 )[(C═O)O—R 2 ] b Si(OR 3 ) 3-a (R 4 ) a ]  (I)

or at least one pendant group of Formula (II):

[—CH 2 CH(R 1 )[(C═O )O—R 2 ] b Si(OR 3 ) 3-a (R 4 ) a ]  (II)

wherein:

each occurrence of R 1 is independently a hydrogen atom or a methyl group;

each occurrence of R 2 is independently a hydrocarbylene group containing from 1 to 12 carbon atoms and optionally containing at least one oxygen atom;

each occurrence of R 3 is independently selected from the group consisting of an alkyl group of 1 to 6 carbon atoms, an alkyl group of 1 to 6 carbon atoms and containing at least one oxygen atom, and an alkyl group of 1 to 6 carbon atoms in which two R 3 groups are covalently bonded together through a carbon-carbon bond to form a ring containing two oxygen atoms, one silicon atom, and 2 to 12 carbon atoms;

each occurrence of R 4 is an alkyl group of 1 to 4 carbon atoms; and

each occurrence of the subscripts a and b is independently an integer where a is 0 to 2 and b is 0 or 1. with the proviso that when b is 0. the silicon atom is covalently bonded to a carbon atom to form —CH 2 —C(−)(R 1 )Si(OR 3 ) 3-a (R 4 ) a or —CH 2 —CH(R 1 )Si(OR 3 ) 3-a (R 4 ) a group.

7. The crosslinkable silane-containing polyolefin composition of claim 1 wherein the polyolefin containing at least one hydrolysable silyl group (a) is prepared by grafting a silane containing a carbon-carbon double bond onto an already formed homopolymer or by copolymerizing the silane containing a carbon-carbon double bond with one or more comonomers, wherein the monomers and comonomers are selected from the group consisting of ethylene, propylene, 1-butene, 1-hexene, 4-methyl-1-pentene, 1-octene, vinyl acetate, ethyl acrylate, methyl acrylate, methyl methacrylate, t-butyl acrylate, n-butyl acrylate, n-butyl methacrylate, 2-ethylhexyl acrylate, 1,4-pentadiene, 1,3-hexadiene, 1,5-hexadiene, 1,4-octadiene, ethylidene norbornene, styrene, vinyl naphthalene, 4-methylstyrene, alpha-methyl styrene, 4-chlorostyrene, acrylonitrile, methacrylonitrile, alpha-chloroacrylonitrile, vinyl methyl ketone and vinyl ethyl ketone, vinyl chloride, vinylidene chloride, tetrafluoroethylene, chloro-tri-fluoroethylene, acrylic acid, methacrylic acid, maleic acid, and vinyl alcohol.

8. The crosslinkable silane-containing polyolefin composition of claim 7 wherein the silane containing a carbon-carbon double bond is selected from the group consisting of trimethoxy-vinyl-silane, dimethoxy-methyl-vinyl-silane, methoxy-dimethyl-vinyl-silane, triethoxy-vinyl-silane, diethoxy-methyl-vinyl-silane, ethoxy-dimethyl-vinyl-silane, tripropoxy-vinyl-silane, dipropoxy-methyl-vinyl-silane, propoxy-dimethyl-vinyl-silane, tributoxy-vinyl-silane, 2,4-dimethyl-2-vinyl-[1,3,2]dioxasilinane, 2-methoxy-4-methyl-2-vinyl-[1,3,2]dioxasilinane, 2-methoxy-4,4,6-trimethyl-2-vinyl-[1,3,2]dioxasilinane, 2,4,4,6-tetramethyl-2-vinyl-[1,3,2]dioxasilinane, 2,5-dimethyl-2-vinyl-[1,3,2]dioxasilinane, 2-methoxy-5-methyl-2-vinyl-[1,3,2]dioxasilinane, acrylic acid 3-(methoxy-dimethyl-silanyl)-propyl ester, acrylic acid 3-(dimethoxy-methyl-silanyl)-propyl ester, acrylic acid 3-(trimethoxy-silanyl)-propyl ester, acrylic acid 3-(dimethoxy-methyl-silanyl)-propyl ester, 2-methyl-acrylic acid 3-(methoxy-dimethyl-silanyl)-propyl ester, 2-methyl-acrylic acid 3-(dimethoxy-methyl-silanyl)-propyl ester, 2-methyl-acrylic acid 3-(trimethoxy-silanyl)-propyl ester, 2-methyl-acrylic acid 3-(triethoxy-silanyl)-propyl ester, 2-methyl-acrylic acid 3-(tripropoxy-silanyl)-propyl ester, acrylic acid 3-(2,4,4,6-tetramethyl-[1,3,2]dioxasilinan-2-yl)-propyl ester, acrylic acid 3-(2,5-dimethyl-[1,3,2]dioxasilinan-2-yl)-propyl ester, acrylic acid 3-(2,4-dimethyl-[1,3,2]dioxasilinan-2-yl)-propyl ester, acrylic acid 3-(2-methoxy-4,4,6-trimethyl-[1,3,2]dioxasilinan-2-yl)-propyl ester, acrylic acid 3-(2-methoxy-5-methyl-[1,3,2]dioxasilinan-2-yl)-propyl ester, acrylic acid 3-(2-methoxy-4-methyl-[1,3,2]dioxasilinan-2-yl)-propyl ester, 2-methyl-acrylic acid 3-(2,4,4,6-tetramethyl-[1,3,2]dioxasilinan-2-yl)-propyl ester, 2-methyl-acrylic acid 3-(2,5-dimethyl-[1,3,2]dioxasilinan-2-yl)-propyl ester, 2-methyl-acrylic acid 3-(2,4-dimethyl-[1,3,2]dioxasilinan-2-yl)-propyl ester, 2-methyl-acrylic acid 3-(2-methoxy-4,4,6-trimethyl-[1,3,2]dioxasilinan-2-yl)-propyl ester, 2-methyl-acrylic acid 3-(2-methoxy-5-methyl-[1,3,2]dioxasilinan-2-yl)-propyl ester, 2-methyl-acrylic acid 3-(2-methoxy-4-methyl-[1,3,2]dioxasilinan-2-yl)-propyl ester, and mixtures thereof.

9. The crosslinkable silane-containing polyolefin composition of claim 1 wherein the sterically hindered phenol antioxidant (b) is of the general formula (IV):

wherein:

R 5 is a monovalent or polyvalent organic radical of from 1 to 50 carbon atoms and optionally containing substituents selected from group consisting of hydroxyl group, amide group, ester group, isocyanurate group, ether group, amine group, hydrazide group, sulfide group, and mixtures thereof.

10. The crosslinkable silane-containing polyolefin composition of claim 1 wherein the sterically hindered phenol antioxidant (b) is of the general formula (V):

wherein:

R 6 is a divalent, trivalent or tetravalent organic group of from 1 to 50 carbon atoms and optionally containing substituents selected from group consisting of hydroxyl group, amide group, ester group, isocyanurate group, ether group, amine group, hydrazide group, sulfide group, and mixtures thereof; and the subscript c is an integer of from 2 to 4.

11. The crosslinkable silane-containing polyolefin composition of claim 1 wherein the sterically hindered phenol antioxidant (b) is selected from the group consisting of 4-[[3,5-bis[(3,5-ditert-butyl-4-hydroxyphenyl)methyl]-2,4,6-trimethylphenyl]methyl]- 2,6-ditert-butylphenol; octadecyl 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate; 3-(3,5-ditert-butyl-4-hydroxyphenyl)-N′-[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyl]propanehydrazide; ethylenebis(oxyethylene)bis-3,5-tert-butyl-4-hydroxy-m-tolyl)-propionate; pentaerythritol tetrakis(3-(3,5-di-tert-4-hydroxyphenyl)propionate; thiodiethylene bis[3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate-N,N′-hexane-1,6-diylbis(3-(3,5-di-tert-butyl-4-hydroxylphenylpropionamide); 1,3,5-tris-(3,5-di-tert-butyl-4-hydroxybenzyl)-1,3-5-triazine-2,4,6(1H,3H,5H-)-trione; 3,5-di-tert-buytl-4-hydroxy-toluene; 4,4-methylene-bis(3,5-di-tert-butylphenol); and mixtures thereof.

12. The crosslinkable silane-containing polyolefin composition of claim 1 wherein the phosphite processing stabilizer (c) is of the general formula (VI):

wherein:

R 7 is selected from the group consisting of a monovalent hydrocarbon containing from 1 to 25 carbon atoms, a monovalent hydrocarbon containing from 1 to 25 carbon atoms and at least one heteroatom selected from the group consisting of oxygen, nitrogen and sulfur, and a polyvalent hydrocarbon containing from 1 to 25 carbon atoms in which at least one carbon atom is bonded to the oxygen of the oxygen-phosphorus group and at least one carbon atom is covalently bonded to a carbon atom of the R 8 group;

R 8 is selected from the group consisting of a monovalent hydrocarbon containing from 1 to 25 carbon atoms, a monovalent hydrocarbon containing from 1 to 25 carbon atoms and at least one heteroatom selected from the group consisting of oxygen, nitrogen and sulfur, and a polyvalent hydrocarbon containing from 1 to 25 carbon atoms in which at least one carbon atom is bonded to the oxygen of the oxygen-phosphorus group and at least one carbon atom is covalently bonded to a carbon atom of the R 7 group; and

R 9 is a monovalent hydrocarbon containing 1 to 25 carbon atoms and optionally contains at least one heteroatom selected from the group consisting of oxygen, nitrogen and sulfur.

13. The crosslinkable silane-containing polyolefin composition of claim 12 wherein the phosphite processing stabilizer (c) is selected from the group consisting of tris(2,4-di-tert-butylphenyl)phosphite; 2-(2,4,8,10-tetratert-butylbenzo[d][1,3,2]benzodioxaphosphepin-6-yl)oxy-N,N-bis[2-(2,4,8,10-tetratert-butylbenzo[d][1,3,2]benzodioxaphosphepin-6-yl)oxyethyl]ethanamine; bis(2,4-di-tert-butyl-6-methylphenyl)-ethyl-phosphite; 3,9-bis-(2,4-di-tert-butyl-phenoxy)-2,4,8,10-tetraoxa-3,9-diphospha-spiro[5.5]undecane; and mixtures thereof.

14. The crosslinkable silane-containing polyolefin composition of claim 1 wherein the sterically hindered amine light stabilizer (d) is an organic compound containing at least one occurrence of the structural unit of the general formula (VII):

wherein:

A is a nitrogen atom, a carbon atom, or an oxygen atom, with the proviso that the open valences of the atoms A and nitrogen are filled with a hydrogen, an organic group, or a lone pair of electrons, and each occurrence of R 10 is independently an alkyl group of from 1 to 6 carbon atoms.

15. The crosslinkable silane-containing polyolefin composition of claim 14 wherein the sterically hindered amine light stabilizer (d) is a monomeric, oligomeric or polymeric molecule of the general formula (VIII) or (IX):

wherein:

each occurrence of A 1 is independently selected from the group consisting of alkenylene of 1 to 10 carbon atoms, an oxygen atom, and NR 11 ;

each occurrence of R 10 is independently an alkyl group of from 1 to 6 carbon atoms;

R 11 is selected from the group consisting of hydrogen, a monovalent hydrocarbon group of 1 to 10 carbon atoms, an amino group —NR 10 2 wherein R 10 is an alkyl group of from 1 to 6 carbon atoms, a hydroxyl group, and a mercaptan group;

each occurrence of R 12 is independently a divalent alkylene, alkenylene, arylene or aralkylene group of 1 to 20 carbon atoms or a divalent organic group of 1 to 20 carbon atoms containing at least one ether, ester, ketone, amide, amine, thioether, or thioester group;

R 13 is selected from the group consisting of hydrogen, a monovalent hydrocarbon group of 1 to 10 carbon atoms, an amino group —NR 10 2 wherein R 10 is an alkyl group of from 1 to 6 carbon atoms, a hydroxyl group, and a mercaptan group; and

R 14 is independently selected from the group consisting of hydrogen or monovalent alkyl, alkenyl, aryl, or aralkyl of from 1 to 10 carbon atoms;

G 1 is an organic group of 1 to 1000 carbon atoms and optionally contains at least one triazine, pyrimidine, pyridine, [1,3,5]triazinane-2,4,6-trione, [1,3,5]triazine-2,4,6-triamine ether, ester, ketone, amide, amine, thioether, or thioester group; and

the subscripts d and e are integers where d is from 1 to 100 and e from 1 to 100.

16. The crosslinkable silane-containing polyolefin composition of claim 15 wherein the sterically hindered amine light stabilizer (d) is selected from the group consisting of 3-(2,2,6,6-tetramethyl-piperidin-4-yloxy)-propionic acid, 4-(2,2,6,6-tetramethyl-piperidin-4-yl)-butyric acid, poly-[4-(2,2,6,6-tetramethyl-piperidin-4-yl)-butyric acid] ester, poly[[6-[(1,1,3,3-tetramethybutyl)amino]-1,3,5-triazine-2,4-diyl][(2,2,6,6-tetramethyl-4-piperidinyl)imino]-1,6-hexanediyl[(2,2,6,6-tetramethyl-4-piperidiny)imino]], bis(2,2,6,6-tetramethyl-4-piperidyl)-maleate, bis(2,2,6,6-tetraethyl-4-piperidyl)maleate, bis(2,2,6,6-tetrahexyl-4-piperidyl)sebaceate, bis(1,2,2,6,6-pentamethyl-4-piperidinyl)-2-butyl-2-(4-hydroxy-3,5-di-tert-butylbenzyl)-propanedioate, poly-[7-(4-hydroxy-2,2,6,6-tetramethyl-piperidin-1-yl)-4-oxo-heptanoic acid] ester, poly-[6-(4-hydroxy-2,2,6,6-tetraethyl-piperidin-1-yl)-hexanoic acid] ester, poly-[7-(4-hydroxy-2,2,6,6-tetramethyl-piperidin-1-yl)-4-oxo-heptanoic acid] ester, 7-(4-hydroxy-2,2,6,6-tetramethyl-piperidin-1-yl)-4-oxo-heptanoic acid 1-tert-butyl-2,2,6,6-tetramethyl-piperidin-4-yl ester, 7-(4-hydroxy-2,2,6,6-tetramethyl-piperidin-1-yl)-4-oxo-heptanoic acid, 8-(4-hydroxy-2,2,6,6-tetramethyl-piperidin-1-yl)-5-oxo-octanoic acid, 6-(4-hydroxy-2,2,6,6-tetramethyl-piperidin-1-yl)-hexanoic acid, 4-(4-hydroxy-2,2,6,6-tetramethyl-piperidin-1-yl)-benzoic acid, polymer resulting from the reaction of dimethylbutanedioate with 4-hydroxy-2,2,6,6-tetramethyl-1-piperidine ethanol, and mixtures thereof.

17. The crosslinkable silane-containing polyolefin composition of claim 1 wherein the substituted benzotriazol ultraviolet light absorber (e) is of the general Formula (X):

wherein:

R 15 is a hydrogen atom or fluoride, chloride, iodide, nitrile, hydroxyl, carboxyl, or alkyl group of from 1 to 10 carbon atoms;

R 16 is a hydrogen atom or fluoride, chloride, iodide, nitrile, hydroxyl, carboxyl, or alkyl group of from 1 to 10 carbon atoms;

R 17 is a hydrogen atom or hydroxyl, alkoxy, carboxyl, nitrile, chloride, or alkyl group of from 1 to 10 carbon atoms;

R 18 is a hydrogen atom or a monovalent alkyl group containing from 1 to 10 carbon atoms;

R 19 is a hydrogen atom or hydroxyl, alkoxyl, carboxyl, nitrile, chloride, or alkyl group of from 1 to 10 carbon atoms;

R 20 is a hydrogen atom or a monovalent alkyl group containing from 1 to 100 carbon atoms and optionally contains at least one ether, ester, hydroxyl, amino, or carboxyl group; and

R 21 is a hydrogen atom or hydroxyl, carboxyl, nitrile, chloride, or alkyl group of from 1 to 10 carbon atoms; and

with the proviso that at least one of R 17 or R 19 is a hydroxyl group.

18. The crosslinkable silane-containing polyolefin composition of claim 17 wherein the substituted benzotriazol ultraviolet light absorber (e) is selected from the group consisting of 2-benzotriazol-2-yl-6-tert-butyl-4-methyl-phenol, 3-(3-3enzotriazol-2-yl-5-tert-butyl-4-hydroxy-phenyl)-propionic acid 2-(2-hydroxy-ethoxy)-ethyl ester, 3-(3-Benzotriazol-2-yl-5-tert-butyl-4-hydroxy-phenyl)-propionic acid 2-[2-(2-hydroxy-ethoxy)-ethoxy]-ethyl ester, 3-(3-benzotriazol-2-yl-5-tert-butyl-4-hydroxy-phenyl)-propionic acid 2-{2-[2-(2-hydroxy-ethoxy)-ethoxy]-ethoxy}-ethyl ester, 3-(3-benzotriazol-2-yl-5-tert-butyl-4-hydroxy-phenyl)-propionic acid, 4-benzotriazol-2-yl-2-tert-butyl-6-methyl-phenol, 4-benzotriazol-2-yl-2,6-di-tert-butyl-phenol, 2-tert-butyl-4-methyl-6-(5-methyl-benzotriazol-2-yl)-phenol, 2-(3-tert-butyl-2-hydroxy-5-methyl-phenyl)-2H-benzotriazole-5-carbonitrile, 2-tert-butyl-6-(5,6-dichloro-benzotriazol-2-yl)-4-methyl-phenol, 2-(5-chloro-benzotriazol-2-yl)-4,6-bis-(1-methyl-1-phenyl-ethyl)-phenol, 2-benzotriazol-2-yl-4,6-bis-(1-methyl-1-phenyl-ethyl)-phenol, and mixtures thereof.

19. The crosslinkable silane-containing polyolefin composition of claim 1 wherein the curing catalyst (f) is selected from the group consisting of mineral acid, organic acid, Lewis acid, group 1A or 1B salts of hydroxide, amines, metal alkoxides, metal oxides, metal carboxylates including tin carboxylates and cobalt carboxylates, metal chelated with organic ligands, and mixtures thereof.

20. The crosslinkable silane-containing polyolefin composition of claim 19 wherein the curing catalyst (f) is selected from the group consisting of dibutyltin diacetate, dibutyl tin dilaurate, dioctyltin dilaurate, dibutyltin dioleate, stannous acetate, cobalt naphthenate, zinc caprylate, iron 2-ethylhexanoate, tetra-butyl titanate, tetra-ethyl titanate, tetra-nonyl titanate, and mixtures thereof.

21. A process for making the crosslinkable silane-containing polyolefin composition of claim 1 comprising mixing a polyolefin containing at least one hydrolysable silyl group (a) with a stabilizer masterbatch comprising a polyolefin, a sterically hindered phenol antioxidant (b), a phosphite processing stabilizer (c), a sterically hindered amine light stabilizer (d), a substituted benzotriazol ultraviolet light absorber (e), a curing catalyst (f) and silicone-polyether copolymer (g).

22. An article made from a cured composition of the crosslinkable silane-containing polyolefin composition of claim 1 .

23. The article of claim 22 wherein the article is selected from the group consisting of potable water pipes, radiant floor heating pipes, central and district heating pipes and ducts, air conditioning pipes and ducts, pipes for transporting gases, compressed air, fluids, valves, bottles, fittings, joints, cylinders, and tanks.

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Reel/Frame 063197/0475 →
FIRST LIEN TERM LOAN PATENT AGREEMENT Recorded Jun 5, 2019
From: MOMENTIVE PERFORMANCE MATERIALS INC.
To: BNP PARIBAS, AS ADMINISTRATIVE AGENT
Reel/Frame 049387/0782 →
ABL PATENT AGREEMENT Recorded Jun 5, 2019
From: MOMENTIVE PERFORMANCE MATERIALS INC.; MOMENTIVE PERFORMANCE MATERIALS GMBH
To: CITIBANK, N.A., AS ADMINISTRATIVE AGENT
Reel/Frame 049388/0252 →
SECOND LIEN TERM LOAN PATENT AGREEMENT Recorded Jun 5, 2019
From: MOMENTIVE PERFORMANCE MATERIALS INC.
To: KOOKMIN BANK, NEW YORK BRANCH, AS ADMINISTRATIVE AGENT
Reel/Frame 049388/0220 →
TERMINATION AND RELEASE OF SECURITY INTEREST IN PATENTS Recorded May 21, 2019
From: JPMORGAN CHASE BANK, N.A.
To: MOMENTIVE PERFORMANCE MATERIALS INC.
Reel/Frame 050304/0555 →
RELEASE OF SECURITY INTEREST Recorded May 15, 2019
From: BOKF, NA
To: MOMENTIVE PERFORMANCE MATERIALS INC.
Reel/Frame 049194/0085 →
RELEASE OF SECURITY INTEREST Recorded May 15, 2019
From: BOKF, NA
To: MOMENTIVE PERFORMANCE MATERIALS INC.
Reel/Frame 049249/0271 →
NOTICE OF CHANGE OF COLLATERAL AGENT - ASSIGNMENT OF SECURITY INTEREST IN INTELLECTUAL PROPERTY Recorded Mar 6, 2015
From: THE BANK OF NEW YORK MELLON TRUST COMPANY, N.A. AS COLLATERAL AGENT
To: BOKF, NA, AS SUCCESSOR COLLATERAL AGENT
Reel/Frame 035136/0457 →
NOTICE OF CHANGE OF COLLATERAL AGENT - ASSIGNMENT OF SECURITY INTEREST IN INTELLECTUAL PROPERTY - SECOND LIEN Recorded Mar 6, 2015
From: THE BANK OF NEW YORK MELLON TRUST COMPANY, N.A. AS COLLATERAL AGENT
To: BOKF, NA, AS SUCCESSOR COLLATERAL AGENT
Reel/Frame 035137/0263 →
TERMINATION AND RELEASE OF SECURITY INTEREST IN PATENT RIGHTS Recorded Oct 30, 2014
From: THE BANK OF NEW YORK MELLON TRUST COMPANY, N.A.
To: MOMENTIVE PERFORMANCE MATERIALS INC.
Reel/Frame 034113/0252 →
TERMINATION AND RELEASE OF SECURITY INTEREST IN PATENT RIGHTS Recorded Oct 30, 2014
From: THE BANK OF NEW YORK MELLON TRUST COMPANY, N.A.
To: MOMENTIVE PERFORMANCE MATERIALS INC.
Reel/Frame 034113/0331 →
SECURITY INTEREST Recorded Oct 27, 2014
From: MOMENTIVE PERFORMANCE MATERIALS INC.
To: THE BANK OF NEW YORK MELLON TRUST COMPANY, N.A., AS COLLATERAL AGENT
Reel/Frame 034066/0662 →
SECURITY INTEREST Recorded Oct 27, 2014
From: MOMENTIVE PERFORMANCE MATERIALS INC.
To: THE BANK OF NEW YORK MELLON TRUST COMPANY, N.A., AS COLLATERAL AGENT
Reel/Frame 034066/0570 →
SECURITY AGREEMENT Recorded Apr 29, 2013
From: MOMENTIVE PERFORMANCE MATERIALS INC.
To: JPMORGAN CHASE BANK, N.A.
Reel/Frame 030311/0343 →
PATENT SECURITY AGREEMENT Recorded Apr 3, 2013
From: MOMENTIVE PERFORMANCE MATERIALS INC.
To: BANK OF NEW YORK MELLON TRUST COMPANY, N.A., THE
Reel/Frame 030185/0001 →
SECURITY AGREEMENT Recorded May 31, 2012
From: MOMENTIVE PERFORMANCE MATERIALS INC
To: BANK OF NEW YORK MELLON TRUST COMPANY, N.A., THE
Reel/Frame 028344/0208 →
SECURITY AGREEMENT Recorded Mar 28, 2012
From: MOMENTIVE PERFORMANCE MATERIALS INC.; MOMENTIVE PERFORMANCE MATERIALS GMBH; MOMENTIVE PERFORMANCE MATERIALS JAPAN LLC
To: JPMORGAN CHASE BANK, N.A.
Reel/Frame 027944/0386 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 25, 2011
From: LACROIX, CHRISTINE; RAMDATT, PHILBERT E.; POHL, ERIC R.
To: MOMENTIVE PERFORMANCE MATERIALS INC.
Reel/Frame 026176/0160 →