Stabilizer compositions and methods for using same for protecting organic materials from uv light and thermal degradation

Patent metadata

Field	Value
Publication number	US-2016145427-A1
Application number	US-201514947163-A
Country	US
Kind code	A1
Filing date	Nov 20, 2015
Priority date	Nov 20, 2014
Publication date	May 26, 2016
Grant date	—

Abstract

Stabilizer compositions having a stabilizing amount of at least one co-active agent; and a stabilizing amount of any one or more ultraviolet light absorber chosen from an ortho-hydroxyphenyl triazine, an ortho-hydroxy benzophenone, or an ortho-hydroxyphenyl benzotriazole, optionally in combination with a stabilizing amount of a hindered amine light stabilizer, are provided herein, along with masterbatch concentrates containing same, and processes for using same for stabilizing organic materials to protect against light and thermal degradation due to exposure to UV irradiation.

First claim

We claim:

1 . A stabilizer composition comprising:
i) a stabilizing amount of an ultraviolet light absorber (UVA) selected from the group consisting of: orthohydroxyphenyl triazine compounds; orthohydroxybenzophenone compounds; orthohydroxyphenyl benzotriazole compounds; benzoxazinone compounds; and mixtures thereof; ii) a stabilizing amount of a co-active agent selected from the group consisting of C 12 -C 60 alcohols; alkoxylated alcohols or monoalkyl ethers thereof; alkoxylated esters of fatty acids; sorbitan esters or ethoxylates thereof; mono- or polyglycerol esters having from 1 to 20 glycerol units or alkoxylates thereof; alkoxylated fatty amines, esters thereof, or salts thereof; sugar esters; alkoxylated fatty amides; ethylene oxide/propylene oxide copolymers; and mixtures thereof, wherein the co-active agent is present at from 1 wt. % to 99 wt. % based on the total weight of the stabilizer composition; and iii) a stabilizing amount of a hindered amine light stabilizer compound (HALS) comprising a functional group according to Formula (II):

wherein R 31 is chosen from: hydrogen; OH; C 1 -C 20 hydrocarbyl; —CH 2 CN; C 1 -C 12 acyl; or C 1 -C 18 alkoxy; R 38 is chosen from: hydrogen; or C 1 -C 8 hydrocarbyl; and each of R 29 , R 30 , R 32 , and R 33 is independently chosen from C 1 -C 20 hydrocarbyl, or R 29 and R 30 and/or R 32 and R 33 taken together with the carbon to which they are attached form a C 5 -C 10 cycloalkyl; or

a functional group according to Formula (IIa):

wherein
m is an integer from 1 to 2;
R 39 is chosen from: hydrogen; OH; C 1 -C 20 hydrocarbyl; —CH 2 CN; C 1 -C 12 acyl; or C 1 -C 18 alkoxy; and
each of G 1 -G 4 is independently chosen from C 1 -C 20 hydrocarbyl; or

mixtures of HALS compounds having functional groups according to Formula (II) and Formula (IIa).

2 . A stabilizer composition according to claim 1 , wherein the co-active agent and the UV absorber combined with HALS (co-active agent: (UVA+HALS)) are present in a weight ratio from 1:20 to 50:1.

3 . A stabilizer composition according to claim 1 , wherein the ortho-hydroxyphenyl triazine compound is a 2-(2′-hydroxyphenyl)-1,3,5-triazine compound according to Formula (I):

wherein
R 34 and R 35 are the same or different and are independently chosen from
a C 6 -C 10 aryl group, wherein the C 6 -C 10 aryl group is optionally substituted at from 1 to 3 substitutable positions with one or more group chosen from OH, halogen, C 1 -C 12 alkyl, C 1 -C 12 alkoxy, C 1-12 alkoxyester, C 2-12 alkanoyl, or phenyl, wherein the phenyl is optionally substituted at from 1 to 3 substitutable positions with one or more group chosen from: hydroxyl, halogen, C 1-12 alkyl, C 1-12 alkoxy, C 1-12 alkoxyester, or C 2-12 alkanoyl;
mono- or di-C 1 -C 12 hydrocarbyl-substituted amino;
C 2 -C 12 alkanoyl;
C 1 -C 12 alkyl;
C 1 -C 10 acyl; or
C 1 -C 10 alkoxyl; and

R 36 is a substituent that is the same or different at from 0 to 4 positions of the phenoxy portion of Formula (I) and is independently chosen from hydroxyl, halogen, C 1 -C 12 alkyl, C 1 -C 12 alkoxy, C 1 -C 12 alkoxyester, C 2 -C 12 alkanoyl; phenyl; or C 1 -C 12 acyl.

4 . A stabilizer composition according to claim 3 , wherein the 2-(2′-hydroxyphenyl)-1,3,5-triazine compound is selected from the group consisting of
4,6-bis-(2,4-dimethylphenyl)-2-(2-hydroxy-4-octyloxyphenyl)-s-triazine;
2-(4,6-Diphenyl-1,3,5-triazin-2-yl-)-5-((hexyl)oxyl-phenol;
4,6-bis-(2,4-dimethylphenyl)-2-(2,4-dihydroxyphenyl)-s-triazine;
2,4-bis(2,4-dihydroxyphenyl)-6-(4-chlorophenyl)-s-triazine;
2,4-bis[2-hydroxy-4-(2-hydroxy-ethoxy)phenyl]-6-(4-chlorophenyl)-s-triazine;
2,4-bis[2-hydroxy-4-(2-hydroxy-4-(2-hydroxy-ethoxy)phenyl]-6-(2,4-dimethylphenyl)-s-triazine;
2,4-bis[2-hydroxy-4-(2-hydroxyethoxy)phenyl]-6-(4-bromophenyl)-s-triazine;
2,4-bis[2-hydroxy-4-(2-acetoxyethoxy)phenyl]-6-(4-chlorophenyl)-s-triazine;
2,4-bis(2,4-dihydroxyphenyl)-6-(2,4-dimethylphenyl)-s-triazine;
2,4-bis(4-biphenylyl)-6-[2-hydroxy-4-[(octyloxycarbonyl)ethylideneoxy]phenyl]-s-triazine;
2,4-bis(4-biphenylyl)-6-[2-hydroxy-4-(2-ethylhexyloxy)phenyl]-s-triazine;
2-phenyl-4-[2-hydroxy-4-(3-sec-butyloxy-2-hydroxypropyloxy)phenyl]-6-[2-hydroxy-4-(3-sec-amyloxy-2-hydroxypropyloxy)phenyl]-s-triazine;
2,4-bis(2,4-dimethylphenyl)-6-[2-hydroxy-4(-3-benzyloxy-2-hydroxypropyloxy)phenyl]-s-triazine;
2,4-bis(2-hydroxy-4-n-butyloxyphenyl)-6-(2,4-di-n-butyloxyphenyl)-s-triazine;
2,4-bis(2,4-dimethylphenyl)-6-[2-hydroxy-4-(3-nonyloxy-2-hydroxypropyloxy)-5-α-cumylphenyl]-s-triazine;
methylenebis-{2,4-bis(2,4-dimethylphenyl)-6-[2-hydroxy-4-(3-butyloxy-2-hydroxypropoxy)phenyl]-s-triazine};
methylene bridged dimer mixture bridged in the 3:5′, 5:5′ and 3:3′ positions in a 5:4:1 ratio;
2,4,6-tris(2-hydroxy-4-isooctyloxycarbonyliso-propylideneoxy-phenyl)-s-triazine;
2,4,6,-tris(2-hydroxy-4-octyloxy-phenyl)-1,3,5-triazine;
2,4-bis(2,4-dimethylphenyl)-6-(2-hydroxy-4-hexyloxy-5-α-cumylphenyl)-s-triazine;
2-(2,4,6-trimethylphenyl)-4,6-bis[2-hydroxy-4-(3-butyloxy-2-hydroxypropyloxy)phenyl]-s-triazine;
2,4,6-tris[2-hydroxy-4-(3-sec-butyloxy-2-hydroxypropyloxy)-phenyl]-s-triazine;
mixture of 4,6-bis-(2,4-dimethylphenyl)-2-(2-hydroxy-4-(3-dodecyloxy-2-hydroxypropoxy)phenyl)-s-triazine and 4,6-bis-(2,4-dimethylphenyl)-2-(2-hydroxy-4-(3-tridecyloxy-2-hydroxypropoxy)phenyl)-s-triazine;
4,6-bis-(2,4-dimethylphenyl)-2-(2-hydroxy-4(3-(2-ethylhexyloxy)-2-hydroxypropoxy)-phenyl)-s-triazine;
4,6-diphenyl-2-(4-hexyloxy-2-hydroxyphenyl)-s-triazine; and
mixtures thereof.

5 . A stabilizer composition according to claim 1 , wherein the UV absorber includes a orthohydroxybenzophenone compound selected from the group consisting of 2-hydroxy-4-methoxybenzophenone; 2,2′-dihydroxy-4-methoxybenzophenone; 2-hydroxy-4-octyloxybenzophenone; 2,2′-dihydroxy-4,4′-di-methoxybenzophenone; 2,2′-dihydroxybenzophenone; 2,2′,4,4′-tetrahydroxybenzophenone; 2,2′-dihydroxy-4,4′-dimethoxybenzophenone; 2,2′-dihydroxy-4,4′-diethoxybenzophenone; 2,2′-dihydroxy-4,4′-dipropoxybenzophenone; 2,2′-dihydroxy-4,4′-dibutoxybenzophenone; 2,2′-dihydroxy-4-methoxy-4′-ethoxybenzophenone; 2,2′-dihydroxy-4-methoxy-4′-propoxybenzophenone; 2,2′-dihydroxy-4-methoxy-4′-butoxybenzophenone; 2,2′-dihydroxy-4-ethoxy-4′-propoxybenzophenone; 2,2′-dihydroxy-4-ethoxy-4′-butoxybenzophenone; 2,3′-dihydroxy-4,4′-dimethoxybenzophenone; 2,3′-dihydroxy-4-methoxy-4′-butoxybenzophenone; 2-hydroxy-4,4′,5′-trimethoxybenzophenone; 2-hydroxy-4,4′,6′-tributoxybenzophenone; 2-hydroxy-4-butoxy-4′,5′-dimethoxybenzophenone; 2-hydroxy-4-ethoxy-2′,4′-dibutylbenzophenone; 2-hydroxy-4-propoxy-4′,6′-dichlorobenzophenone; 2-hydroxy-4-propoxy-4′,6′-dibromobenzophenone; 2,4-dihydroxybenzophenone; 2-hydroxy-4-ethoxybenzophenone; 2-hydroxy-4-propoxybenzophenone; 2-hydroxy-4-butoxybenzophenone; 2-hydroxy-4-methoxy-4′-methylbenzophenone; 2-hydroxy-4-methoxy-4′-ethylbenzophenone; 2-hydroxy-4-methoxy-4′-propylbenzophenone; 2-hydroxy-4-methoxy-4′-butylbenzophenone; 2-hydroxy-4-methoxy-4′-tertiary butylbenzophenone; 2-hydroxy-4-methoxy-4′-chlorobenzophenone; 2-hydroxy-4-methoxy-2′-chlorobenzophenone; 2-hydroxy-4-methoxy-4′-bromobenzophenone; 2-hydroxy-4,4′-dimethoxybenzophenone; 2-hydroxy-4,4′-dimethoxy-3-methylbenzophenone; 2-hydroxy-4,4′-dimethoxy-2′-ethylbenzophenone; 2-hydroxy-4,4′,5′-trimethoxybenzophenone; 2-hydroxy-4-ethoxy-4′-methyl

Assignees

• Cytec Ind Inc

Inventors

• Eng J Mon Hei
• KOZAKIEWICZ Joseph
• Gupta Ram B
• Cho Jian-Yang
• Ryles Roderick G
• Khawam Fadi

Classifications

• C08K5/132

  Phenols containing keto groups {, e.g. benzophenones} · CPC title

• C08K5/1535

  Five-membered rings · CPC title

• C08K5/34926

  also containing heterocyclic groups other than triazine groups · CPC title

• C08L23/12 Primary

  Polypropene · CPC title

• C08K5/1345

  Carboxylic esters of phenolcarboxylic acids · CPC title