Stabilizing compositions for stabilizing materials against ultraviolet light and thermal degradation

Patent metadata

Field	Value
Publication number	US-9725579-B2
Application number	US-201514700560-A
Country	US
Kind code	B2
Filing date	Apr 30, 2015
Priority date	May 1, 2014
Publication date	Aug 8, 2017
Grant date	Aug 8, 2017

Abstract

Stabilizer compositions for stabilizing materials against degradation due to thermal and ultraviolet light exposure are disclosed herein. In some instances, the stabilizer compositions include an ortho-hydroxyl tris-aryl-s-triazine compound; a hindered amine light stabilizer compound; a hindered hydroxybenzoate compound; a phosphite compound, an acid scavenger and/or thioester; and a hindered phenol antioxidant compound.

First claim

What is claimed is:

1. A thermal and ultraviolet (UV) light stabilizing composition comprising:
an ortho-hydroxyl tris-aryl-s-triazine compound;
a hindered amine light stabilizer compound;
a hindered hydroxybenzoate compound;
an acid scavenger;
a phosphite compound;
a hindered phenol antioxidant compound; and
a thioester compound.

2. The thermal and UV light stabilizing composition according to claim 1 , wherein:
(a) the ortho-hydroxyl tris-aryl-s-triazine compound is a 2-(2′-hydroxyphenyl)-1,3,5-triazine compound according to Formula (I):

wherein each of R 34 and R 35 in Formula (I) is independently chosen from C 6 -C 10 aryl optionally substituted, C 1 -C 10 hydrocarbyl-substituted amino, C 1 -C 10 acyl or C 1 -C 10 alkoxyl; and R 36 in Formula (I) is present at from 0 to 4 positions of the phenoxy portion of Formula I and in each instance is independently chosen from hydroxyl, C 1 -C 12 hydrocarbyl, C 1 -C 12 alkoxyl, C 1 -C 12 alkoxyester, or C 1 -C 12 acyl,
(b) the hindered amine light stabilizer compound comprises a molecular fragment according to Formula (II):

wherein R 31 in Formula (II) 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 in Formula (II) is chosen from: hydrogen; or C 1 -C 8 hydrocarbyl; and each of R 29 , R 30 , R 32 , and R 33 in Formula (II) is independently chosen from C 1 -C 20 hydrocarbyl, or R 29 and R 30 and/or R 32 and R 33 in Formula (II) taken together with the carbon to which they are attached form a C 5 -C 10 cycloalkyl; or
according to Formula (IIa)

wherein m in Formula (IIa) 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 in Formula (IIa) is independently chosen from C 1 -C 20 hydrocarbyl,
(c) the hindered hydroxybenzoate compound is according to Formula (III):

wherein R 17 in Formula (III) is a C 1 -C 8 alkyl and R 18 in Formula (III) is a C 1 -C 24 alkyl or substituted or unsubstituted C 6 -C 24 aryl,
(d) the acid scavenger is selected from the group consisting of zinc oxide, calcium lactate, natural and synthetic hydrotalcites, natural and synthetic hydrocalumites, alkali metal salts and alkaline earth metal salts of higher fatty acids, calcium stearate, zinc stearate, magnesium behenate, magnesium stearate, sodium stearate, sodium ricinoleate and potassium palmitate, antimony pyrocatecholate, zinc pyrocatecholate; and mixtures thereof,
(e) the hindered phenol antioxidant compound comprises a molecular fragment according to one or more of Formula (IVa), (IVb), or (IVc):

wherein R 18 in Formulae (IVa), (IVb) and (IVc) is chosen from hydrogen or a C 1-4 hydrocarbyl; each of R 19 and R 20 in Formulae (IVa), (IVb) and (IVc) is individually chosen from hydrogen or a C 1 -C 20 hydrocarbyl; and R 37 in Formulae (IVa), (IVb) and (IVc) is chosen from C 1 -C 12 hydrocarbyl, and
(f) the phosphite compound is chosen from a hindered arylalkyl phosphite compound according to Formula (V):

wherein each of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , and R 10 in Formula (V) is individually chosen from hydrogen, C 1 -C 12 alkyl, C 3 -C 12 cycloalkyl, C 4 -C 12 alkyl cycloalkyl, C 6 -C 10 aryl, or C 7 -C 12 alkylaryl, R 1 and R 5 together comprise at least 5 carbons and at least one of R 1 and R 5 comprises a tertiary carbon, R 6 and R 10 together comprise at least 5 carbons and at least one of R 6 and R 10 comprises a tertiary carbon; or

a trisarylphosphite according to Formula (VI):

wherein each of R 16 , R 17 , R 40 , R 41 , and R 42 in Formula (VI) is individually chosen from hydrogen, C 1 -C 20 alkyl, C 3 -C 20 cycloalkyl, C 4 -C 20 alkyl cycloalkyl, C 6 -C 10 aryl, or C 7 -C 20 alkylaryl; or mixtures of Formula (V) an Formula (VI); and
(g) the thioester compound is selected from the group consisting of dilauryl thiodipropionate, distearyl thiodipropionate, pentaerythrithol tetrakis-(3-dodecylthipropionate), tetra-alkyl thioethyl thiodisuccinate, 2,12-dihydroxy-4,10-dithia-7-oxatridecamethylene bis[3-(dodecylthio) propionate], polyalkanol esters of alkylthio-alkanoic acids, and diakyl 3,3′-thiodipropionates; and mixtures thereof.

3. The thermal and UV light stabilizing composition according to claim 2 , 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; 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-hydroxypropylox-y)-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-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; 2-(4,6-Diphenyl-1,3,5-triazin-2-yl)-5-[2-(2-ethylhexanoyloxy)ethoxy]phenol; 2,4,6-tris(2-hydroxy-4-octyloxyphenyl)-1,3,5-triazine; propanoic acid, 2,2′,2″-[1,3,5-triazine-2,4,6-triyltris[(3-hydroxy-4,1-phenylene)oxy]]tris-1,1′,1″-trioctyl ester; propanoic acid, 2-[4-[4,6-bis([1,1′-biphenyl]-4-yl)-1,3,5-triazin-2yl]-3-hydroxyphenoxyl]-isooctyl ester; and mixtures thereof.

4. The thermal and UV light stabilizing composition according to claim 2 , wherein the hindered amine light stabilizer is selected from the group consisting of: bis(2,2,6,6-tetramethylpiperidin-4-

Assignees

• Cytec Ind Inc

Inventors

• Gupta Ram B
• Eng Jerry Mon Hei
• Khawam Fadi
• Kamat Ranjan Kumar

Classifications

• C09K15/30

  containing heterocyclic ring with at least one nitrogen atom as ring member · CPC title

• C08K5/527 Primary

  Cyclic esters · CPC title

• C08K5/132

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

• C08K5/3462

  Six-membered rings · CPC title

• C08K2003/222

  Magnesia, i.e. magnesium oxide · CPC title