Ethylenically unsaturated amine salts of sulfonic, phosphoric and carboxylis acids

Abstract

Disclosed are ethylenically unsaturated amine salts of sulfonic, phosphoric and carboxylic acids. The salts are surface active agents which are useful in a variety of applications as primary and/or secondary surfactants. The salts are especially useful as surfactants in emulsion polymerization reactions.

1 . A composition of matter comprising a polymerizable surface active agent which comprises:
 a) at least one acid selected from the group consisting of a phosphoric acid, a polyphosphoric acid, a phosphinic acid, a polyphosphinic acid, and mixtures thereof, and   b) at least one nitrogenous base, wherein the nitrogenous base contains at least one nitrogen atom and at least one ethylenically unsaturated moiety; wherein the polymerizable surface active agent is a salt or quaternary nitrogen compound.   
     
     
         2 . The composition of matter according to  claim 1 , wherein the acid is selected from the group consisting of phosphoric acids, alkoxylated phosphoric acids, polyphosphoric acids, alkoxylated polyphosphoric acids, fluorinated phosphoric acids, phosphoric acid esters of oils, phosphinic acids, alkylphosphinic acids, aminophosphinic acids, polyphosphinic acids, vinyl phosphinic acids, phosphonic acids, polyphosphonic acids, phosphonic acid alkyl esters, α-phosphono fatty acids, organoamino polymethylphosphonic acids, organoamino dialkylene phosphonic acids, alkanolamine phosphonic acids, trialkylidene phosphonic acids, acylamidomethane phosphonic acids, alkyliminodimethylene diphosphonic acids, polymethylene-bis(nitrilo dimethylene)tetraphosphonic acids, alkyl bis(phosphonoalkylidene)amine oxide acids, esters of substituted aminomethylphosphonic acids, phosphonamidic acids, dendritic polyphosphoric acids, fluorinated phosphonic and phosphinic acids, and mixtures thereof. 
     
     
         3 . The composition of matter according to  claim 1 , wherein the nitrogenous base is selected from the group consisting of allyl amine, diallyl amine, triallyl amine, methallyl amine, N-methyl N-allyl amine, allyldimethyl amine, methyl 3-amino crotonate, 3-amino crotononitrile, 3-amino-1-propanol vinyl ether, 2-(dimethylamino)ethyl acrylate, 1,4-diamino-2-butene, and mixtures thereof. 
     
     
         4 . The composition of matter according to  claim 1 , wherein the nitrogenous base is selected from the group consisting of allyl amine, diallyl amine, triallyl amine, methallyl amine, N-methyl N-allyl amine, 2-(dimethylamino)ethyl acrylate, and mixtures thereof. 
     
     
         5 . The composition of matter according to  claim 1 , wherein the composition of matter further comprises water. 
     
     
         6 . A composition of matter comprising a polymerizable surface active agent of the formula:
   R 1 O(PO 3 ) x− M +   y      
       wherein R 1  is a saturated or unsaturated hydrocarbon group having from about 1-24 carbon atoms, phenyl, polyphenyl, napthyl, polynapthyl, styryl, or polystyryl group, an alkyl/alkoxylate substituted phenyl, an alkyl/alkoxylate substituted or poly-substituted polyphenyl, an alkyl/alkoxylate substituted or poly-substituted napthyl, an alkyl/alkoxylate substituted or poly-substituted polynapthyl, an alkyl/alkoxylate substituted or poly-substituted styryl, or an alkyl/alkoxylate substituted or poly-substituted polystyryl group, and mixtures thereof, M +  is a conjugate acid of a nitrogenous base containing at least one nitrogen atom and at least one ethylenically unsaturated moiety; x=1 or 2; and y=1 or 2. 
     
     
         7 . The composition of matter according to  claim 6 , wherein the nitrogenous base is selected from the group consisting of allyl amine, diallyl amine, triallyl amine, methallyl amine, N-methyl N-allyl amine, allyldimethyl amine, methyl 3-amino crotonate, 3-amino crotononitrile, 3-amino-1-propanol vinyl ether, 2-(dimethylamino)ethyl acrylate, 1,4-diamino-2-butene, and mixtures thereof. 
     
     
         8 . A composition of matter according to  claim 6 , wherein the nitrogenous base is selected from the group consisting of allyl amine, diallyl amine, triallyl amine, methallyl amine, N-methyl N-allyl amine, 2-(dimethylamino)ethyl acrylate, and mixtures thereof. 
     
     
         9 . A composition of matter according to  claim 6 , wherein R 1  is a saturated or unsaturated hydrocarbon group having from about 1-24 carbon atoms. 
     
     
         10 . The composition of matter according to  claim 6 , wherein the composition of matter further comprises water. 
     
     
         11 . A composition of matter comprising a polymerizable surface active agent of the formula:
   [R 1 O(CH 2 CH(R′)O) m ] n P(O) p   x− M +   y      
       wherein R 1  is a saturated or unsaturated hydrocarbon group having from about 1-24 carbon atoms; R′ is methyl or hydrogen; M +  is a conjugate acid of a nitrogenous base containing at least one nitrogen atom and at least one ethylenically unsaturated moiety; m=0-100; n=1 or 2; p=2 or 3; x=1 or 2; and y=1 or 2. 
     
     
         12 . The composition of matter according to  claim 11 , wherein the nitrogenous base is selected from the group consisting of allyl amine, diallyl amine, triallyl amine, methallyl amine, N-methyl N-allyl amine, allyldimethyl amine, methyl 3-amino crotonate, 3-amino crotononitrile, 3-amino-1-propanol vinyl ether, 2-(dimethylamino)ethyl acrylate, 1,4-diamino-2-butene, and mixtures thereof. 
     
     
         13 . The composition of matter according to  claim 11 , wherein the nitrogenous base is selected from the group consisting of allyl amine, diallyl amine, triallyl amine, methallyl amine, N-methyl N-allyl amine, 2-(dimethylamino)ethyl acrylate, and mixtures thereof. 
     
     
         14 . The composition of matter according to  claim 11 , wherein the composition of matter further comprises water. 
     
     
         15 . A composition of matter comprising a polymerizable surface active agent of the formula:
   [(R 1 ) n ArO(CH 2 CH(R′)O) m ] q P(O) p   x− M +   y      
       wherein R 1  is a saturated or unsaturated hydrocarbon group having from about 1-24 carbon atoms; Ar is phenyl; R′ is methyl or hydrogen; M +  is a conjugate acid of a nitrogenous base containing at least one nitrogen atom and at least one ethylenically unsaturated moiety; n=1-4; m=0-100; q=1 or 2; p=2 or 3; x=1 or 2; and y=1 or 2. 
     
     
         16 . The composition of matter according to  claim 15 , wherein the nitrogenous base is selected from the group consisting of allyl amine, diallyl amine, triallyl amine, methallyl amine, N-methyl N-allyl amine, allyldimethyl amine, methyl 3-amino crotonate, 3-amino crotononitrile, 3-amino-1-propanol vinyl ether, 2-(dimethylamino)ethyl acrylate, 1,4-diamino-2-butene, and mixtures thereof. 
     
     
         17 . The composition of matter according to  claim 15 , wherein the nitrogenous base is selected from the group consisting of allyl amine, diallyl amine, triallyl amine, methallyl amine, N-methyl N-allyl amine, 2-(dimethylamino)ethyl acrylate, and mixtures thereof. 
     
     
         18 . The composition of matter according to  claim 15 , wherein the composition of matter further comprises water.