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US4587346A Expired / Lapsed US ⏱️ 0.0 years remaining

Liquid 2-(2-hydroxy-3-higher branched alkyl-5-methyl-phenyl)-2H-benzotriazole mixtures, stabilized compositions and processes for preparing liquid mixtures

Assignee: BASF Corp
•
Filing: 1985-01-22
•
Granted: 1986-05-06
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Expires: 2005-01-22
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Abstract

Abstract Liquid 2-(2-hydroxy-3-higher branched alkyl-5-methylphenyl)-2H-benzotriazole mixtures are prepared by alkylating 2-(2-hydroxy-5-methylphenyl)-2H-benzotriazole with a straight chain alkene or with a branched chain alkene of 8 to 30 carbon atoms in the presence of an acidic catalyst at 100°-200° C. The liquid mixtures exhibit outstanding efficacy in protecting organic substrates from light induced deterioration as well as good resistance to loss by volatilization or exudation during the processing of stabilized compositions at elevated temperatures.

Inventors

  • 👤 Roland A. E. Winter
  • 👤 Robert E. Detlefsen

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-05 16:08
CPC Classifications
C; C08; C08K; C08K5/00; C08K5/16; C08K5/34; C08K5/3467; C08K5/3472; C08K5/3475; C07; C07D; C07D249/00; C07D249/16; C07D249/18; C07D249/20; Y; Y10; Y10S; Y10S430/00; Y10S430/132

Claims Analysis

Total Claims: 24
Claim 1
Independent Claim 203 words
A process for preparing a normally liquid or non-crystalline mixture of benzotriazoles, suitable for stabilizing organic materials against light induced deterioration, which consists essentially of compounds of the formula ##STR11## wherein T 1 is hydrogen or chloro, and T 2 is a random statistical mixture of at least three isomeric branched secondary alkyl groups each having 8 to 30 carbon atoms and having the formula ##STR12## where E 1 is a straight chain alkyl of 1 to 14 carbon atoms and E 2 is a straight chain alkyl of 4 to 15 carbon atoms where the total number of carbon atoms in E 1 plus E 2 is 7 to 29, which process comprises alkylating a benzotriazole of the formula ##STR13## where T 1 is hydrogen or chloro, with a straight chain alkene of 8 to 30 carbon atoms in the presence of an acidic catalyst at a temperature of 100 to 200° C., wherein the equivalent ratio of alkene to 2H-benzotriazole is 1:1 to 6:1, and the equivalents of acidic catalyst selected from the groups consisting of aliphatic, aromatic and substituted aromatic sulfonic acids, sulfuric acid, phosphoric acid, acidic clays and acidic molecular sieves per equivalent of benzotriazole is 0.2 to 3.
Claim 2
Dependent Claim 203 words
A process for preparing a normally liquid or non-crystalline mixture of benzotriazoles, suitable for stabilizing organic materials against light induced deterioration, which consists essentially of compounds of the formula ##STR11## wherein T 1 is hydrogen or chloro, and T 2 is a random statistical mixture of at least three isomeric branched secondary alkyl groups each having 8 to 30 carbon atoms and having the formula ##STR12## where E 1 is a straight chain alkyl of 1 to 14 carbon atoms and E 2 is a straight chain alkyl of 4 to 15 carbon atoms where the total number of carbon atoms in E 1 plus E 2 is 7 to 29, which process comprises alkylating a benzotriazole of the formula ##STR13## where T 1 is hydrogen or chloro, with a straight chain alkene of 8 to 30 carbon atoms in the presence of an acidic catalyst at a temperature of 100 to 200° C., wherein the equivalent ratio of alkene to 2H-benzotriazole is 1:1 to 6:1, and the equivalents of acidic catalyst selected from the groups consisting of aliphatic, aromatic and substituted aromatic sulfonic acids, sulfuric acid, phosphoric acid, acidic clays and acidic molecular sieves per equivalent of benzotriazole is 0.2 to 3.
Claim 3
Dependent Claim 11 words
A process according to claim 1 wherein T 1 is hydrogen.
Claim 4
Dependent Claim 17 words
A process according to claim 1 wherein T 2 is alkyl of 8 to 16 carbon atoms.
Claim 5
Dependent Claim 17 words
A process according to claim 3 wherein T 2 is alkyl of 10 to 12 carbon atoms.
Claim 6
Dependent Claim 14 words
A process according to claim 1 wherein the temperature is 140° to 170° C.
Claim 7
Dependent Claim 12 words
A process according to claim 5 wherein the temperature is 160°-165° C.
Claim 8
Dependent Claim 18 words
A process according to claim 1 wherein the equivalent ratio of alkene to 2H-benzotriazole is 3.5:1 to 4.5:1.
Claim 9
Dependent Claim 15 words
A process according to claim 1 wherein the acidic catalyst is an aliphatic sulfonic acid.
Claim 10
Dependent Claim 13 words
A process according to claim 8 wherein the acidic catalyst is methanesulfonic acid.
Claim 11
Dependent Claim 21 words
A process according to claim 1 wherein the per equivalent of acidic catalyst to equivalents of benzotriazole is 0.3 to 2.
Claim 12
Dependent Claim 21 words
A process according to claim 10 wherein the per equivalent of acidic catalyst to equivalents of benzotriazole is 0.5 to 1.
Claim 13
Dependent Claim 164 words
A process for preparing a normally liquid or non-crystalline mixture of benzotriazoles, suitable for stabilizing organic materials against light induced deterioration, which consists essentially of compounds of the formula ##STR14## wherein R 1 is hydrogen or chloro, and R 2 is a random statistical mixture of at least three isomeric branched alkyl groups each having 8 to 30 carbon atoms and having a multiplicity of alkyl branches along the main alkyl chain, which process comprises alkylating a benzotriazole of the formula ##STR15## where R 1 is hydrogen or chloro, with a branched chain alkene of 8 to 30 carbon atoms in the presence of an acidic catalyst at a temperature of 100° to 200° C., wherein the equivalent ratio of alkene to 2H-benzotriazole is 1:1 to 6:1, and the equivalents of acidic catalyst selected from the groups consisting of aliphatic, aromatic and substituted aromatic sulfonic acids, sulfuric acid, phosphoric acid, acidic clays and acidic molecular sieves per equivalent of benzotriazole is 0.2 to 3.
Claim 14
Dependent Claim 164 words
A process for preparing a normally liquid or non-crystalline mixture of benzotriazoles, suitable for stabilizing organic materials against light induced deterioration, which consists essentially of compounds of the formula ##STR14## wherein R 1 is hydrogen or chloro, and R 2 is a random statistical mixture of at least three isomeric branched alkyl groups each having 8 to 30 carbon atoms and having a multiplicity of alkyl branches along the main alkyl chain, which process comprises alkylating a benzotriazole of the formula ##STR15## where R 1 is hydrogen or chloro, with a branched chain alkene of 8 to 30 carbon atoms in the presence of an acidic catalyst at a temperature of 100° to 200° C., wherein the equivalent ratio of alkene to 2H-benzotriazole is 1:1 to 6:1, and the equivalents of acidic catalyst selected from the groups consisting of aliphatic, aromatic and substituted aromatic sulfonic acids, sulfuric acid, phosphoric acid, acidic clays and acidic molecular sieves per equivalent of benzotriazole is 0.2 to 3.
Claim 15
Dependent Claim 11 words
A process according to claim 12 wherein R 1 is hydrogen.
Claim 16
Dependent Claim 17 words
A process according to claim 12 wherein R 2 is alkyl of 8 to 16 carbon atoms.
Claim 17
Dependent Claim 17 words
A process according to claim 14 wherein R 2 is alkyl of 9 to 12 carbon atoms.
Claim 18
Dependent Claim 14 words
A process according to claim 12 wherein the temperature is 140° to 170° C.
Claim 19
Dependent Claim 12 words
A process according to claim 16 wherein the temperature is 160°-165° C.
Claim 20
Dependent Claim 18 words
A process according to claim 12 wherein the equivalent ratio of alkene to 2H-benzotriazole is 3.5:1 to 4.5:1.
Claim 21
Dependent Claim 15 words
A process according to claim 12 wherein the acidic catalyst is an aliphatic sulfonic acid.
Claim 22
Dependent Claim 13 words
A process according to claim 12 wherein the acidic catalyst is methanesulfonic acid.
Claim 23
Dependent Claim 20 words
A process according to claim 12 wherein the equivalent of acidic catalyst to equivalents of benzotriazole is 0.3 to 2.
Claim 24
Dependent Claim 20 words
A process according to claim 21 wherein the equivalent of acidic catalyst to equivalents of benzotriazole is 0.5 to 1.

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1989-05-05 1989-11-04 1990-05-06 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1993-05-05 1993-11-04 1994-05-06 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1997-05-05 1997-11-04 1998-05-06 $7700.00 Window Closed / Lapsed

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