Antiskinning compound and compositions containing them

Abstract

The invention relates to anti-skinning agents containing combinations of (a) organic or inorganic oxygen scavengers with (b) alkylamines and/or alkyl alkanolamines and also relates to compositions containing the combination, especially oxidatively drying paints or coating compositions and articles coated with such oxidatively drying paints or coating compositions.

1 . A coating material, paint or finish which contains an oxidatively drying film former and, as an antiskinning agent, a combination comprising 
 a) an organic or inorganic oxygen scavenger of, with    b) an alkyl amine of formula (II)                          where R 3 , R 4  and R 5  may be mutually independently hydrogen but all three can not be hydrogen, a linear or branched, saturated or unsaturated C 1 -C 20  aliphatic molecule or radical, which can optionally be mono- or polysubstituted, or a C 6 -C 12  aryl molecule or radical, a C 7 -C 14  araliphatic molecule or radical or a C 5 -C 7  cycloaliphatic molecule or radical, and/or    c) an alkyl alkanol amine of formula (III)                          where R 6  and R 8  may be mutually independently hydrogen but both can not be hydrogen, a linear or branched, saturated or unsaturated C 1 -C 20  aliphatic molecule or radical, which can optionally be mono- or polysubstituted, a C 6 -C 12  aryl molecule or radical, a C 7 -C 14  araliphatic molecule or radical or a C 5 -C 7  cycloaliphatic molecule or radical and R 7  may be a linear or branched, saturated or unsaturated C 1 -C 20  aliphatic molecule or radical, which can optionally be mono- or polysubstituted, a C 6 -C 12  aryl molecule or radical, a C 7 -C 14  araliphatic molecule or radical or a C 5 -C 7  cycloaliphatic molecule or radical.    
   
   
       2 . The coating material, paint or finish of  claim 1  wherein said organic or inorganic oxygen scavenger is a hydroxylamine of the general formula:  
     
       
         
         
             
             
         
       
       where R 1  and R 2  mutually independently hydrogen, a linear or branched, saturated or unsaturated C 1 -C 20  aliphatic molecule or radical, which can optionally be mono- or polysubstituted, or a C 6 -C 12  aryl molecule or radical, a C 7 -C 14  araliphatic radical or a C 5 -C 7  cycloaliphatic.  
     
   
   
       3 . The coating material, paint or finish of  claim 2  wherein the hydroxylamine is selected from hydroxylamine, mono-methylhydroxylamine, dimethylhydroxylamine, methyl ethylhydroxylamine, monoethylhydroxylamine, diethylhydroxylamine, dibutylhydroxylamine, dibenzylhydroxylamine, mono-isopropylhydroxylamine and mixtures thereof.  
   
   
       4 . The coating material, paint or finish of  claim 1  wherein the organic or inorganic oxygen scavenger is selected from hydroquinone, substituted hydroquinones, semi-hydroquinone, catechol, substituted catechols, erythorbic acid, carbohydrazides, methyl ethyl ketoxime and sulfites.  
   
   
       5 . The coating material, paint or finish of  claim 1  wherein the alkyl amine is selected from: monoethyl amine, diethyl amine, triethyl amine, monoisopropyl amine, diisopropyl amine, monobutyl amine, dibutylamine, tributyl amine, monoamyl amine, dimethyl ethyl amine, dimethyl isopropyl amine, ethyl diisopropyl amine, sec-butyl amine, tetramethylpropylenediamine, diethylaminopropylamine, 3-methoxypropylamine, dimethylaminopropylaminopropylamine and 3-isopropoxypropylamine and mixtures thereof.  
   
   
       6 . The coating material, paint or finish of  claim 1  wherein the alkyl alkanolamine is selected from: methylaminoethanol, dimethylaminoethanol, methydiethanolamine, ethylaminoethanol, diethylaminoethanol, dimethylamino-2-propanol, isopropylaminoethanol, disiopropylaminoethanol, butylaminoethanol, dibutylaminoethanol, butyldiethanolamine, tert-butylaminoethanol and mixtures thereof.  
   
   
       7 . The coating material, paint or finish of  claim 1 , which contains the said combination in an amount of from 0.001 to 2% by weight, based on the total surface coating.  
   
   
       8 . The coating material, paint or finish of  claim 1 , which contains an alkyd resin as the oxidatively drying film former.  
   
   
       9 . A process for the production of a coating material, paint or finish containing an oxidatively drying film former comprising incorporating into the coating material, paint or finish, an antiskinning combination comprising 
 a) an organic or inorganic oxygen scavenger, with    b) an alkyl amine of formula (II)                          where R 3 , R 4  and R 5  may be mutually independently hydrogen but all three can not be hydrogen, a linear or branched, saturated or unsaturated C 1 -C 20  aliphatic molecule or radical, which can optionally be mono- or polysubstituted, or a C 6 -C 12  aryl molecule or radical, a C 7 -C 14  araliphatic molecule or radical or a C 5 -C 7  cycloaliphatic molecule or radical, and/or    c) an alkyl alkanolamine of formula (III)                          where R 6  and R 8  may be mutually independently hydrogen but both can not be hydrogen, a linear or branched, saturated or unsaturated C 1 -C 20  aliphatic molecule or radical, which can optionally be mono- or polysubstituted, a C 6 -C 12  aryl molecule or radical, a C 7 -C 14  araliphatic radical or a C 5 -C 7  cycloaliphatic molecule or radical and R 7  may be a linear or branched, saturated or unsaturated C 1 -C 20  aliphatic molecule or radical, which can optionally be mono- or polysubstituted, a C 6 -C 12  aryl molecule or radical, a C 7 -C 14  araliphatic molecule or radical or a C 5 -C 7  cycloaliphatic molecule or radical.    
   
   
       10 . The process of  claim 9  wherein the said organic or inorganic oxygen scavenger is a hydroxylamine of the general formula I,  
     
       
         
         
             
             
         
       
       where R 1  and R 2  mutually independently hydrogen, a linear or branched, saturated or unsaturated C 1 -C 20  aliphatic molecule or radical, which can optionally be mono- or polysubstituted, or a C 6 -C 12  aryl molecule or radical, a C 7 -C 14  araliphatic molecule or radical or a C 5 -C 7  cycloaliphatic molecule or radical.  
     
   
   
       11 . The process of  claim 9  wherein said hydroxylamine is selected from hydroxylamine, mono-methylhydroxylamine, dimethylhydroxylamine, methyl ethylhydroxylamine, monoethylhydroxylamine, diethylhydroxylamine, dibutylhydroxylamine, dibenzylhydroxylamine, mono-isopropylhydroxylamine and mixtures thereof.  
   
   
       12 . The process of  claim 9  wherein the organic or inorganic oxygen scavenger is selected from hydroquinone, substituted hydroquinones, semi-hydroquinone, catechol, substituted catechols, erythorbic acid, carbohydrazides, methyl ethyl ketoxime and sulfites.  
   
   
       13 . The process of  claim 9  wherein the alkyl amine is selected from: monoethyl amine, diethyl amine, triethyl amine, monoisopropyl amine, diisopropyl amine, monobutyl amine, dibutylamine, tributyl amine, monoamyl amine, dimethyl ethyl amine, dimethyl isopropyl amine, ethyl diisopropyl amine, sec-butyl amine, tetramethylpropylenediamine, diethylaminopropylamine, 3-methoxypropylamine, dimethylaminopropylaminopropylamine and 3-isopropoxypropylamine and mixtures thereof.  
   
   
       14 . The process of  claim 9  wherein the alkyl alkanolamine is selected from: methylaminoethanol, dimethylaminoethanol, methydiethanolamine, ethylaminoethanol, diethylaminoethanol, dimethylamino-2-propanol, isopropylaminoethanol, disiopropylaminoethanol, butylaminoethanol, dibutylaminoethanol, butyldiethanolamine, tert-butylaminoethanol and mixtures thereof.  
   
   
       15 . The process of  claim 9 , wherein said coating material, paint or finish containing an oxidatively drying film former contains said combination in an amount of from 0.001 to 2% by weight, based on the total surface coating.  
   
   
       16 . The process of  claim 9 , wherein said coating material, paint or finish containing an oxidatively drying film former contains an alkyd resin as the oxidatively drying film former.  
   
   
       17 . An article coated with a coating material, paint or finish containing an oxidatively drying film former, wherein an antiskinning combination comprising 
 a) an organic or inorganic oxygen scavenger; with    b) an alkyl amine of formula (II)                          where R 3 , R 4  and R 5  may be mutually independently hydrogen but all three can not be hydrogen, a linear or branched, saturated or unsaturated C 1 -C 20  aliphatic molecule or radical, which can optionally be mono- or polysubstituted, or a C 6 -C 12  aryl molecule or radical, a C 7 -C 14  araliphatic molecule or radical or a C 5 -C 7  cycloaliphatic molecule or radical, and/or    c) an alkyl alkanolamine of formula (III)                          where R 6  and R 8  may be mutually independently hydrogen but both can not be hydrogen, a linear or branched, saturated or unsaturated C 1 -C 20  aliphatic molecule or radical, which can optionally be mono- or polysubstituted, a C 6 -C 12  aryl molecule or radical, a C 7 -C 14  araliphatic molecule or radical or a C 5 -C 7  cycloaliphatic molecule or radical and R 7  may be a linear or branched, saturated or unsaturated C 1 -C 20  aliphatic molecule or radical, which can optionally be mono- or polysubstituted, a C 6 -C 12  aryl radical, a C 7 -C 14  araliphatic molecule or radical or a C 5 -C 7  cycloaliphatic molecule or radical is incorporated into the coating material, paint or finish.    
   
   
       18 . The article of  claim 17  wherein said organic or inorganic oxygen scavenger is a hydroxylamine of the general formula:  
     
       
         
         
             
             
         
       
       where R 1  and R 2  mutually independently hydrogen, a linear or branched, saturated or unsaturated C 1 -C 20  aliphatic molecule or radical, which can optionally be mono- or polysubstituted, or a C 6 -C 12  aryl molecule or radical, a C 7 -C 14  araliphatic molecule or radical or a C 5 -C 7  cycloaliphatic molecule or radical.  
     
   
   
       19 . The article of  claim 18  wherein said hydroxylamine is selected from hydroxylamine, mono-methylhydroxylamine, dimethylhydroxylamine, methyl ethylhydroxylamine, monoethylhydroxylamine, diethylhydroxylamine, dibutylhydroxylamine, dibenzylhydroxylamine, mono-isopropylhydroxylamine and mixtures thereof.  
   
   
       20 . The article of  claim 17  wherein the organic or inorganic oxygen scavenger is selected from hydroquinone, substituted hydroquinones, semi-hydroquinone, catechol, substituted catechols, erythorbic acid, carbohydrazides, methyl ethyl ketoxime and sulfites.  
   
   
       21 . The article of  claim 17  wherein the alkyl amine is selected from: monoethyl amine, diethyl amine, triethyl amine, monoisopropyl amine, diisopropyl amine, monobutyl amine, dibutylamine, tributyl amine, monoamyl amine, dimethyl ethyl amine, dimethyl isopropyl amine, ethyl diisopropyl amine, sec-butyl amine, tetramethylpropylenediamine, diethylaminopropylamine, 3-methoxypropylamine, dimethylaminopropylaminopropylamine and 3-isopropoxypropylamine and mixtures thereof.  
   
   
       22 . The article of  claim 17  wherein the alkyl alkanolamine is selected from: methylaminoethanol, dimethylaminoethanol, methydiethanolamine, ethylaminoethanol, diethylaminoethanol, dimethylamino-2-propanol, isopropylaminoethanol, disiopropylaminoethanol, butylaminoethanol, dibutylaminoethanol, butyldiethanolamine, tert-butylaminoethanol and mixtures thereof.  
   
   
       23 . The article of  claim 17 , wherein said coating material, paint or finish containing an oxidatively drying film former contains said combination in an amount of from 0.001 to 2% by weight, based on the total surface coating.  
   
   
       24 . The article of  claim 17 , wherein said coating material, paint or finish containing an oxidatively drying film former contains an alkyd resin as the oxidatively drying film former.