CA1087344A - Light-stable polyolefin compositions - Google Patents
Light-stable polyolefin compositionsInfo
- Publication number
- CA1087344A CA1087344A CA304,827A CA304827A CA1087344A CA 1087344 A CA1087344 A CA 1087344A CA 304827 A CA304827 A CA 304827A CA 1087344 A CA1087344 A CA 1087344A
- Authority
- CA
- Canada
- Prior art keywords
- hydroxy
- light
- composition
- butyl
- benzotriazole
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/13—Phenols; Phenolates
- C08K5/134—Phenols containing ester groups
- C08K5/1345—Carboxylic esters of phenolcarboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/13—Phenols; Phenolates
- C08K5/132—Phenols containing keto groups, e.g. benzophenones
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3467—Heterocyclic compounds having nitrogen in the ring having more than two nitrogen atoms in the ring
- C08K5/3472—Five-membered rings
- C08K5/3475—Five-membered rings condensed with carbocyclic rings
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Abstract
ABSTRACT OF THE DISCLOSURE
Polyolefins are light-stabilized by mixtures of (a) a 2-hydroxy-4-alkoxybenzophenone or a 2-(2'-hydroxy-5'--alkylphenyl)benzotriazole and (b) an alkyl or alkenyl ester of 3,5-dialkyl-4-hydroxybenzoic acid.
Polyolefins are light-stabilized by mixtures of (a) a 2-hydroxy-4-alkoxybenzophenone or a 2-(2'-hydroxy-5'--alkylphenyl)benzotriazole and (b) an alkyl or alkenyl ester of 3,5-dialkyl-4-hydroxybenzoic acid.
Description
--` 1087344 This invention relates to light-stable polyolefin compositions. More particularly, it relates to polyolefin compositions stabilized against the deteriorative effects of light by the incorporation therein of a light-stabilizing ~ ;
amount of a combination of (a) a 2-hydroxy-4-alkoxybenzo-phenone or a 2-(2'-hydroxy-5'-alkylphenyl)benzotriazole, and ~ -(b) a compound represented by the formula (I):
NO~C ORl wherein Rl represents an alkyl or alkenyl radical having 1-20 carbon atoms; R2 represents an alkyl radical having 1-8 carbon atoms; and R3 represents an alkyl radical branched on ; the alpha carbon atom having 3-8 carbon atoms. Preferably, Rl is alkyl of 6-20 carbon atoms and R2 and R3 are both t-butyl.
It is well-known that sunlight and other sources of ultraviolet radiation cause degradation of polymers as evidenced by embrittlement or yellowing of plastic articles made therefrom. It is also well-known that this degradation can be inhibited by incorporating light stabilizer additives in or on such articles.
Various additives, used alone or in combinations, have been suggested in order to prolong the useful lives of articles made from polyolefins. Since none has been found ; to be completely satisfactory, research continues in order to find new compounds, or combinations of compounds, which will be more satisfactory.
In accordance with the invention there is provided - ` 1087344 a composition of matter stabilized against the deteriorative effects of light comprising in combination a polyolefin, and light-stabilizing amounts of (a) a 2-hydroxy-4-alkoxybenzo-phenone or a 2-(2'-hydroxy-5'-alkylphenyl)benzotriazole, wherein the aIkoxy and alkyl substituents have up to 12 car-bon atoms, and (b) a compound represented by formula (I).
Generally, effective stabilization occurs when the polyolefin compositions contain from about 0.1% to about 4.0% of each of the light stabilizer compounds, based on the weight of the polyolefin.
Preferably, the compositions comprise polypropyl-ene containing from about 0.2% to about 2.0% of each of the light stabilizer compounds, basea on the weight of the poly-propylene. More preferably, the compositions comprise poly-propylene containing about 0.25% by weight of either 2-hy-droxy-4-n-octyloxybenzophenone or 2-(2'-hydroxy-5'-t-octyl-phenyl)benzotriazole, and 0.25% by weight of n-hexadecyl 3,5-di-t-butyl-4-hydroxybenzoate, based on the weight of the polypropylene.
The compositions of this invention have signifi-cantly better resistance to the deteriorative effects of light than similar compositions comprising a polyolefin and equal total amounts of any single one of these known light stabilizer compounds used alone.
The compositions of this invention provide light-stable polyolefins which are useful in films, sheets and fibers, particularly in films and sheets.
The light stabilizer compounds may be incorporated into or on such plastic materials by any of the various pro-cedures known in the art for such purpose, such as by dry
amount of a combination of (a) a 2-hydroxy-4-alkoxybenzo-phenone or a 2-(2'-hydroxy-5'-alkylphenyl)benzotriazole, and ~ -(b) a compound represented by the formula (I):
NO~C ORl wherein Rl represents an alkyl or alkenyl radical having 1-20 carbon atoms; R2 represents an alkyl radical having 1-8 carbon atoms; and R3 represents an alkyl radical branched on ; the alpha carbon atom having 3-8 carbon atoms. Preferably, Rl is alkyl of 6-20 carbon atoms and R2 and R3 are both t-butyl.
It is well-known that sunlight and other sources of ultraviolet radiation cause degradation of polymers as evidenced by embrittlement or yellowing of plastic articles made therefrom. It is also well-known that this degradation can be inhibited by incorporating light stabilizer additives in or on such articles.
Various additives, used alone or in combinations, have been suggested in order to prolong the useful lives of articles made from polyolefins. Since none has been found ; to be completely satisfactory, research continues in order to find new compounds, or combinations of compounds, which will be more satisfactory.
In accordance with the invention there is provided - ` 1087344 a composition of matter stabilized against the deteriorative effects of light comprising in combination a polyolefin, and light-stabilizing amounts of (a) a 2-hydroxy-4-alkoxybenzo-phenone or a 2-(2'-hydroxy-5'-alkylphenyl)benzotriazole, wherein the aIkoxy and alkyl substituents have up to 12 car-bon atoms, and (b) a compound represented by formula (I).
Generally, effective stabilization occurs when the polyolefin compositions contain from about 0.1% to about 4.0% of each of the light stabilizer compounds, based on the weight of the polyolefin.
Preferably, the compositions comprise polypropyl-ene containing from about 0.2% to about 2.0% of each of the light stabilizer compounds, basea on the weight of the poly-propylene. More preferably, the compositions comprise poly-propylene containing about 0.25% by weight of either 2-hy-droxy-4-n-octyloxybenzophenone or 2-(2'-hydroxy-5'-t-octyl-phenyl)benzotriazole, and 0.25% by weight of n-hexadecyl 3,5-di-t-butyl-4-hydroxybenzoate, based on the weight of the polypropylene.
The compositions of this invention have signifi-cantly better resistance to the deteriorative effects of light than similar compositions comprising a polyolefin and equal total amounts of any single one of these known light stabilizer compounds used alone.
The compositions of this invention provide light-stable polyolefins which are useful in films, sheets and fibers, particularly in films and sheets.
The light stabilizer compounds may be incorporated into or on such plastic materials by any of the various pro-cedures known in the art for such purpose, such as by dry
- 2 -1 blending the additive with the polyolefin in powder or gran-ular form, followed ! byimillih~.Banbury m~xing~ mo(lding, casting;-extrud-ing~, swe~ling,la~a the likeY~by immérsing;the polyolefin as film, sheet, fibers,:etc. ih~a-solution of the additive in an appropriate solvent (as ip a dyeing process), etc.
The amounts of the light-stabilizer compounds needed for effective stabilization of the polyolefin against degradation will depend on the nature of the polyolefin and the amount of exposure to ultraviolet light to which the art-icle will be subjected.
The esters of formula (I) may be prepared by the reaction of a suitable 3,5-dialkyl-4-hydroxybenzoic acid with an appropriate alcohol in the presence of a catalyst such as sulfuric acid. They may also be prepared by react-ing the appropriate alcohol with a suitable 3,5-dialkyl-4--hydroxybenzoyl chloride.
The preparation of many compounds of formula (I) can be found in the literature. For example, Dexter et al., in Examples 1-3 of United States Patent 3,681,431, describe the preparations of the n-octadecyl, n-hexyl and n-dodecyl esters of 3,5-di-t-butyl-4-hydroxybenzoic acid.
Suitable compounds within the scope of formula (I) include the following: n-octadecyl 3,5-di-t-butyl-4-hydroxy-benzoate, n-hexadecyl 3,5-di-t-butyl-4-hydroxybenzoate, n-octa-decyl 3,5-diisopropyl-4-hydroxybenzoate, isobutyl 3,5-di-t--octyl-4-hydroxybenzoate, methyl 3-methyl-5-isopropyl-4-hy-droxybenzoate, cyclohexyl 3,5-di-t-amyl-4-hydroxybenzoate, allyl 3,5-di-t-butyl-4-hydroxybenzoate, 2-butenyl 3,5-di-isopropyl-4-hydroxybenzoate and n-octadecyl 3-n-octyl-5-t-
The amounts of the light-stabilizer compounds needed for effective stabilization of the polyolefin against degradation will depend on the nature of the polyolefin and the amount of exposure to ultraviolet light to which the art-icle will be subjected.
The esters of formula (I) may be prepared by the reaction of a suitable 3,5-dialkyl-4-hydroxybenzoic acid with an appropriate alcohol in the presence of a catalyst such as sulfuric acid. They may also be prepared by react-ing the appropriate alcohol with a suitable 3,5-dialkyl-4--hydroxybenzoyl chloride.
The preparation of many compounds of formula (I) can be found in the literature. For example, Dexter et al., in Examples 1-3 of United States Patent 3,681,431, describe the preparations of the n-octadecyl, n-hexyl and n-dodecyl esters of 3,5-di-t-butyl-4-hydroxybenzoic acid.
Suitable compounds within the scope of formula (I) include the following: n-octadecyl 3,5-di-t-butyl-4-hydroxy-benzoate, n-hexadecyl 3,5-di-t-butyl-4-hydroxybenzoate, n-octa-decyl 3,5-diisopropyl-4-hydroxybenzoate, isobutyl 3,5-di-t--octyl-4-hydroxybenzoate, methyl 3-methyl-5-isopropyl-4-hy-droxybenzoate, cyclohexyl 3,5-di-t-amyl-4-hydroxybenzoate, allyl 3,5-di-t-butyl-4-hydroxybenzoate, 2-butenyl 3,5-di-isopropyl-4-hydroxybenzoate and n-octadecyl 3-n-octyl-5-t-
- 3 -~1187344 . .
1 -butyl-4-hydroxybenzoate.
Suitable light stabilizers of the 2-hydroxy-4--alkoxybenzophenone class include the following: 2-hydroxy-
1 -butyl-4-hydroxybenzoate.
Suitable light stabilizers of the 2-hydroxy-4--alkoxybenzophenone class include the following: 2-hydroxy-
-4-n-octyloxybenzophenone, 2-hydroxy-4-methoxybenzophenone, 2-hydroxy-4-dodecyloxybenzophenone, 2-hydroxy-4-n-butoxy-benzophenone, 2,2'-dihydroxy-4-n-octyloxybenzophenone, 2,2'--dihydroxy-4,4'-dimethoxybenzophenone, 2-hydroxy-4-n-decyl-oxybenzophenone, 2,2'-dihydroxy-4,4'-di-n-(octyloxy)benzo-phenone, 2,2'-dihydroxy-4-i-butoxybenzophenone, 2,2'-dihydroxy--4-methoxybenzophenone and 2-hydroxy-4-isooctyloxybenzophen-one.
Suitable light stabilizers of the 2-(2'-hydroxy-
Suitable light stabilizers of the 2-(2'-hydroxy-
-5'-alkylphenyl)benzotriazole class include the following:
2-(2'-hydroxy-5'-t-octylphenyl)benzotriazole, 2-(2'-hydroxy--5'-methylphenyl)-benzotriazole, 2-(2'-hydroxy-5'-t-butyl-phenyl)-benzotriazole, 2-(2'-hydroxy-5'-amylphenyl)-benzo-- triazole, 2-(2'-hydroxy-3',5'-dimethylphenyl)-benzotriazole, 2-(2'-hydroxy-5'-t-butylphenyl)-5-chlorobenzotriazole, 2-(2'--hydroxy-5'-t-octylphenyl)-5-methoxybenzotriazole, 2-(2'-20 -hydroxy-5'-t-octylphenyl)-5-methylbenzotriazole, 2-(2'-hy- -~
droxy-5'-dodecylphenyl)-benzotriazole, 2-(2'-hydroxy-3'-t--butyl-5'-methylphenyl)-5-chlorobenzotriazole, and 2-(2'--hydroxy-3',5'-di-t-butylphenyl)-5-chlorobenzotriazole.
The combination of light-stabilizing compounds of this invention is useful for protecting organic polymeric materials normally subject to deterioration by ultraviolet light, particularly polyolefins. As used herein, the term polyolefins includes homopolymers such as low density poly-ethylene, high density polyethylene, polypropylene, polysty-rene, polybutadiene, polybutylene, polyisoprene, and the 1 like, and copolymers such as ethylene-propylene copolymer, ethylene-butylene copolymer, ethylene-vinyl acetate copoly-mer, styrene-butadiene copolymer, acrylonitrile-styrene-buta-diene copolymer, and the like.
The aforementioned combination of light-stabilizing compounds may also be used in combination with other addi-tives such as antioxidants, fillers, pigments, dyes, anti-static agents, and the like.
The following examples, in which parts and percent-ages are by weight unless otherwise stated, are presented to further illustrate the present invention.
Examples 1 - 6 General Procedure Unstabilized polypropylene (100 parts) was dry blended with 2,6-di-t-butyl-4-methylphenol (0.05 part), octa-decyl 3,5-di-t-butyl-4-hydroxyhydrocinnamate (0.05 part), calcium stearate (0.10 part) and a stabilizer additive (0.50 part), or a combination of two stabilizer additives (0.25 part each), under test. The blended composition was extruded at a maximum temperature of 440F., and pelletized. The pel-lets were then extruded into monofilaments at a maximum temp-erature of 485F. with a draw ratio of 7 to 1. After expos-ure to a xenon arc in a Weather-Ometer for various periods of time, the monofilaments were tested for breaking strength and the results obtained were converted into percent of the original strength of the filament.
The following results were obtained with light-stabilizer compounds and combinations of light-stabilizer compounds, following the procedure described above. The table shows (Examples 1-4) the results obtained using 0.5 _ 5 _ 1~87344 1 part of each of the light-stabilizer compounds alone. Also included are results obtained with combinations of the 2-hy-droxy-4-alkoxybenzophenone of the 2-(2'-hydroxy-5'-alkoxy-phenyl)benzotriazole with the aromatic 3,5-di-alkyl-4-hydroxy-benzoate (Examples 5-6, illustrative of the prior art) or with the alkyl 3,5-di-alkyl-4-hydroxybenzoate (Examples 7-8, illustrative of the present invention).
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1~7344 1 These results show that the combinations of stab-ilizer additives of this invention provide a significant improvement in light stabilization of polypropylene.
In the manner described above, substituting 0.25 part of n-octadecyl 3,5-diisopropyl-4-hydroxybenzoate, iso-butyl 3,5-di-t-octyl-4-hydroxybenzoate, methyl 3-methyl-5--isopropyl-4-hydroxybenzoate, cyclohexyl 3,5-di-t-amyl-4-hy-droxybenzoate, allyl 3,5-di-t-butyl-4-hydroxybenzoate, n-octa- ;
decyl 3,5-di-t-butyl-4-hydroxybenzoate, or n-dodecyl 3,5--di-t-butyl-4-hydroxybenzoate for the additive of Example 4, similar results are obtained.
In the manner described in Example 7, substituting -;
0.1-4.0 parts of 2-hydroxy-4-methoxybenzophenone, 2-hydroxy--4-dodecyloxybenzophenone, 2-hydroxy-4-n-butoxybenzophenone, 2,2'-dihydroxy-4-n-octyloxybenzophenone, 2,2'-dihydroxy-4,4'- -;
-dimethoxybenzophenone, 2,2'-4,4'-n-octyloxybenzophenone, 2,2'-dihydroxy-4-i-butoxybenzophenone or 2,2'-dihydroxy-4--methoxybenzophenone for the 2-hydroxy-4-n-octyloxybenzophen-one, similar results are obtained.
In the manner described in Example 8, substituting 0.1-4.0 parts of 2-(2'-hydroxy-5'-methylphenyl)-benzotriazole, 2-(2'-hydroxy-5'-t-butylphenyl)-benzotriazole, 2-(2'-hy-droxy-5'-amylphenyl)benzotriazole, 2-(2'-hydroxy-3',5'-di-methylphenyl)benzotriazole, 2-(2'-hydroxy-5'-t-butylphenyl)--5-chlorobenzotriazole, 2-(2'-hydroxy-5'-t-octylphenyl)-5--methoxybenzotriazole, 2-(2'-hydroxy-5'-t-octylphenyl)-5--methylbenzotriazole, 2-(2'-hydroxy-5'-n-dodecylphenyl)-benzotriazole, 2-(2'-hydroxy-3'-t-butyl-5'-methylphenyl)-5--chlorobenzotriazole, or 2-(2'-hydroxy-3',5'-di-t-butyl-phenyl)-5-chlorobenzotriazole for 2-(2'-hydroxy-5'-t-octyl-.. , . :. , 1 phenyl)benzotriazole, similar results are obtained.
Example 9 In the manner described in Examples 7-8 utilizing 0.125 part each of the light stabilizers of Examples l and 2 and 0.25 part of the ester of Example 4, per hundred parts of polypropylene, similar results are obtained.
- Examples 10 - 11 In the manner described in Examples 7-8, substi-tuting a high impact ethylene-butylene copolymer for the polypropylene, similar results are obtained.
.:
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2-(2'-hydroxy-5'-t-octylphenyl)benzotriazole, 2-(2'-hydroxy--5'-methylphenyl)-benzotriazole, 2-(2'-hydroxy-5'-t-butyl-phenyl)-benzotriazole, 2-(2'-hydroxy-5'-amylphenyl)-benzo-- triazole, 2-(2'-hydroxy-3',5'-dimethylphenyl)-benzotriazole, 2-(2'-hydroxy-5'-t-butylphenyl)-5-chlorobenzotriazole, 2-(2'--hydroxy-5'-t-octylphenyl)-5-methoxybenzotriazole, 2-(2'-20 -hydroxy-5'-t-octylphenyl)-5-methylbenzotriazole, 2-(2'-hy- -~
droxy-5'-dodecylphenyl)-benzotriazole, 2-(2'-hydroxy-3'-t--butyl-5'-methylphenyl)-5-chlorobenzotriazole, and 2-(2'--hydroxy-3',5'-di-t-butylphenyl)-5-chlorobenzotriazole.
The combination of light-stabilizing compounds of this invention is useful for protecting organic polymeric materials normally subject to deterioration by ultraviolet light, particularly polyolefins. As used herein, the term polyolefins includes homopolymers such as low density poly-ethylene, high density polyethylene, polypropylene, polysty-rene, polybutadiene, polybutylene, polyisoprene, and the 1 like, and copolymers such as ethylene-propylene copolymer, ethylene-butylene copolymer, ethylene-vinyl acetate copoly-mer, styrene-butadiene copolymer, acrylonitrile-styrene-buta-diene copolymer, and the like.
The aforementioned combination of light-stabilizing compounds may also be used in combination with other addi-tives such as antioxidants, fillers, pigments, dyes, anti-static agents, and the like.
The following examples, in which parts and percent-ages are by weight unless otherwise stated, are presented to further illustrate the present invention.
Examples 1 - 6 General Procedure Unstabilized polypropylene (100 parts) was dry blended with 2,6-di-t-butyl-4-methylphenol (0.05 part), octa-decyl 3,5-di-t-butyl-4-hydroxyhydrocinnamate (0.05 part), calcium stearate (0.10 part) and a stabilizer additive (0.50 part), or a combination of two stabilizer additives (0.25 part each), under test. The blended composition was extruded at a maximum temperature of 440F., and pelletized. The pel-lets were then extruded into monofilaments at a maximum temp-erature of 485F. with a draw ratio of 7 to 1. After expos-ure to a xenon arc in a Weather-Ometer for various periods of time, the monofilaments were tested for breaking strength and the results obtained were converted into percent of the original strength of the filament.
The following results were obtained with light-stabilizer compounds and combinations of light-stabilizer compounds, following the procedure described above. The table shows (Examples 1-4) the results obtained using 0.5 _ 5 _ 1~87344 1 part of each of the light-stabilizer compounds alone. Also included are results obtained with combinations of the 2-hy-droxy-4-alkoxybenzophenone of the 2-(2'-hydroxy-5'-alkoxy-phenyl)benzotriazole with the aromatic 3,5-di-alkyl-4-hydroxy-benzoate (Examples 5-6, illustrative of the prior art) or with the alkyl 3,5-di-alkyl-4-hydroxybenzoate (Examples 7-8, illustrative of the present invention).
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8 ~ ~, o o ~ luo o ~ ~ 3 ~ ~ ;
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~i .~ ~ ~ N I ~ ~ o ~r ~i a) ~ ~ I o ;~ ar ~ r ~ O 'r N ~U N~ 3 ~o ~ o ~ ~ aJ U~ X U U~ Ul ~ "
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1~7344 1 These results show that the combinations of stab-ilizer additives of this invention provide a significant improvement in light stabilization of polypropylene.
In the manner described above, substituting 0.25 part of n-octadecyl 3,5-diisopropyl-4-hydroxybenzoate, iso-butyl 3,5-di-t-octyl-4-hydroxybenzoate, methyl 3-methyl-5--isopropyl-4-hydroxybenzoate, cyclohexyl 3,5-di-t-amyl-4-hy-droxybenzoate, allyl 3,5-di-t-butyl-4-hydroxybenzoate, n-octa- ;
decyl 3,5-di-t-butyl-4-hydroxybenzoate, or n-dodecyl 3,5--di-t-butyl-4-hydroxybenzoate for the additive of Example 4, similar results are obtained.
In the manner described in Example 7, substituting -;
0.1-4.0 parts of 2-hydroxy-4-methoxybenzophenone, 2-hydroxy--4-dodecyloxybenzophenone, 2-hydroxy-4-n-butoxybenzophenone, 2,2'-dihydroxy-4-n-octyloxybenzophenone, 2,2'-dihydroxy-4,4'- -;
-dimethoxybenzophenone, 2,2'-4,4'-n-octyloxybenzophenone, 2,2'-dihydroxy-4-i-butoxybenzophenone or 2,2'-dihydroxy-4--methoxybenzophenone for the 2-hydroxy-4-n-octyloxybenzophen-one, similar results are obtained.
In the manner described in Example 8, substituting 0.1-4.0 parts of 2-(2'-hydroxy-5'-methylphenyl)-benzotriazole, 2-(2'-hydroxy-5'-t-butylphenyl)-benzotriazole, 2-(2'-hy-droxy-5'-amylphenyl)benzotriazole, 2-(2'-hydroxy-3',5'-di-methylphenyl)benzotriazole, 2-(2'-hydroxy-5'-t-butylphenyl)--5-chlorobenzotriazole, 2-(2'-hydroxy-5'-t-octylphenyl)-5--methoxybenzotriazole, 2-(2'-hydroxy-5'-t-octylphenyl)-5--methylbenzotriazole, 2-(2'-hydroxy-5'-n-dodecylphenyl)-benzotriazole, 2-(2'-hydroxy-3'-t-butyl-5'-methylphenyl)-5--chlorobenzotriazole, or 2-(2'-hydroxy-3',5'-di-t-butyl-phenyl)-5-chlorobenzotriazole for 2-(2'-hydroxy-5'-t-octyl-.. , . :. , 1 phenyl)benzotriazole, similar results are obtained.
Example 9 In the manner described in Examples 7-8 utilizing 0.125 part each of the light stabilizers of Examples l and 2 and 0.25 part of the ester of Example 4, per hundred parts of polypropylene, similar results are obtained.
- Examples 10 - 11 In the manner described in Examples 7-8, substi-tuting a high impact ethylene-butylene copolymer for the polypropylene, similar results are obtained.
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Claims (8)
1. A composition of matter stabilized against the deteriorative effects of light comprising a polyolefin norm-ally subject to deterioration by light, stabilizing amounts of (a) a 2-hydroxy-4-alkoxybenzophenone, or a 2-(2'-hydroxy--5'-alkylphenyl)benzotriazole, wherein the alkoxy and alkyl substituents have up to 12 carbon atoms, inclusive, and (b) a compound of the formula (I):
wherein R1 represents an alkyl or alkenyl radical having 1-20 carbon atoms, inclusive, R2 represents an alkyl radical having 1-8 carbon atoms, inclusive, and R3 represents an alkyl radical branched on the alpha carbon atom having 3-8 carbon atoms, inclusive.
wherein R1 represents an alkyl or alkenyl radical having 1-20 carbon atoms, inclusive, R2 represents an alkyl radical having 1-8 carbon atoms, inclusive, and R3 represents an alkyl radical branched on the alpha carbon atom having 3-8 carbon atoms, inclusive.
2. The composition of Claim 1, comprising about 0.1-4.0% of each of the light-stabilizer compounds, based on the weight of the polyolefin.
3. The composition of Claim 2 comprising about 0.2-2.0% of each of the light-stabilizer compounds, and where-in the polyolefin is polypropylene.
4. The composition of Claim 1 wherein R2 and R3 represent t-butyl.
5. The composition of Claim 1 wherein R1 is alkyl of 6 to 20 carbon atoms.
6. The composition of Claim 1 wherein the poly-olefin is a copolymer of propylene and ethylene.
7. The composition of Claim 1 comprising polypro-pylene and 0.25% by weight each of 2-hydroxy-4-n-octyloxy-benzophenone and n-hexadecyl 3,5-di-t-butyl-4-hydroxybenzo-ate.
8. The composition of Claim 1 comprising poly-propylene and 0.25% by weight each of 2-(2'-hydroxy-5'-t--octylphenyl)benzotriazole and n-hexadecyl 3,5-di-t-butyl--4-hydroxybenzoate.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US81662277A | 1977-07-18 | 1977-07-18 | |
| US816,622 | 1977-07-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1087344A true CA1087344A (en) | 1980-10-07 |
Family
ID=25221162
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA304,827A Expired CA1087344A (en) | 1977-07-18 | 1978-06-06 | Light-stable polyolefin compositions |
Country Status (11)
| Country | Link |
|---|---|
| JP (1) | JPS5421450A (en) |
| AU (1) | AU3642678A (en) |
| BE (1) | BE869003A (en) |
| BR (1) | BR7804592A (en) |
| CA (1) | CA1087344A (en) |
| DE (1) | DE2828363A1 (en) |
| FR (1) | FR2398089A1 (en) |
| NL (1) | NL7806493A (en) |
| PL (1) | PL208485A1 (en) |
| SE (1) | SE7807906L (en) |
| ZA (1) | ZA782930B (en) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1161241A (en) * | 1980-09-18 | 1984-01-31 | Paula A. Paolino | Combination of phenolic antioxidant and stabilizer for use in organic materials |
| JPS5959473U (en) * | 1982-10-13 | 1984-04-18 | 本田技研工業株式会社 | Automotive battery device |
| CA2038179A1 (en) * | 1990-03-26 | 1991-09-27 | Donald Frederick Anderson | Stabilization of phenoxarsine microbiocides |
| JP3987632B2 (en) * | 1998-04-27 | 2007-10-10 | 株式会社Ａｄｅｋａ | Automotive interior and exterior materials |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3681431A (en) * | 1970-02-06 | 1972-08-01 | Ciba Geigy Corp | N-OCTADECYL 3,5-DI-t-BUTYL-4-HYDROXYBENZOATE |
| US3658910A (en) * | 1970-02-11 | 1972-04-25 | Carlisle Chemical Works | Liquid 2-hydroxy-4-alkoxybenzophenones |
| CH527873A (en) * | 1970-08-26 | 1972-09-15 | Ciba Geigy Ag | Use of aryl 4-hydroxy-benzoate as light stabilizers |
-
1978
- 1978-05-22 ZA ZA00782930A patent/ZA782930B/en unknown
- 1978-05-24 AU AU36426/78A patent/AU3642678A/en active Pending
- 1978-06-06 CA CA304,827A patent/CA1087344A/en not_active Expired
- 1978-06-15 NL NL7806493A patent/NL7806493A/en not_active Application Discontinuation
- 1978-06-28 DE DE19782828363 patent/DE2828363A1/en not_active Withdrawn
- 1978-07-14 BE BE189289A patent/BE869003A/en unknown
- 1978-07-17 BR BR7804592A patent/BR7804592A/en unknown
- 1978-07-17 JP JP8621678A patent/JPS5421450A/en active Pending
- 1978-07-17 SE SE787807906A patent/SE7807906L/en unknown
- 1978-07-17 PL PL20848578A patent/PL208485A1/en unknown
- 1978-07-18 FR FR7821307A patent/FR2398089A1/en not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| SE7807906L (en) | 1979-01-19 |
| DE2828363A1 (en) | 1979-02-08 |
| BE869003A (en) | 1979-01-15 |
| NL7806493A (en) | 1979-01-22 |
| BR7804592A (en) | 1979-04-10 |
| ZA782930B (en) | 1979-05-30 |
| FR2398089A1 (en) | 1979-02-16 |
| JPS5421450A (en) | 1979-02-17 |
| AU3642678A (en) | 1979-11-29 |
| PL208485A1 (en) | 1979-03-26 |
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