Acidified polyamidoamine adhesives, method of manufacture, and use for creping and ply bond applications

Abstract

A paper adhesive composition includes a cationic non-crosslinked acidified solution of a polyamidoamine with the repeating units wherein n≧1; m=1 or 2; X −m is chloride, bromide, iodide, sulfate, bisulfate, nitrate, oxalate, alkyl carboxylate, aryl carboxylate, hydrogen phosphate, dihydrogen phosphate, alkyl sulfonate, aryl sulfonate, or a combination comprising at least one of the foregoing anions; R 1 is a divalent aliphatic, cycloaliphatic, or araliphatic group having from 1 to 24 carbon atoms; R 2 is hydrogen or a monovalent aliphatic, cycloaliphatic, or araliphatic group having from 1 to 24 carbon atoms; and R 3 is a divalent hydrocarbon radical derived from a dibasic carboxylic acid.

1 . An adhesive composition for paper manufacturing and use of the adhesive composition for paper manufacturing, the adhesive composition comprising an aqueous solution comprising a cationic non-crosslinked polyamidoamine having repeating units of the structure 
       
         
           
           
               
               
           
         
         wherein n≧1; 
         m=1 or 2; 
         X −m  is chloride, bromide, iodide, sulfate, bisulfate, nitrate, oxalate, alkyl carboxylate, aryl carboxylate, hydrogen phosphate, dihydrogen phosphate, alkyl sulfonate, aryl sulfonate, or a combination comprising at least one of the foregoing anions; 
         R 1  is a divalent aliphatic, cycloaliphatic, or araliphatic group having from 1 to 24 carbon atoms; 
         R 2  is hydrogen or a monovalent aliphatic, cycloaliphatic, or araliphatic group having from 1 to 24 carbon atoms; and 
         R 2  is a divalent hydrocarbon radical derived from a dibasic carboxylic acid having from 1 to 24 carbon atoms. 
       
     
     
         2 . The adhesive solution of  claim 1 , having a pH of 1 to 6.9. 
     
     
         3 . The adhesive of  claim 1 , having a weight average molecular weight from 2 thousand to 1 million Daltons. 
     
     
         4 . The adhesive of  claim 1 , wherein n=1, X −m  is bisulfate, R 1  is ethylene, R 2  is hydrogen, and R 3  is butylene. 
     
     
         5 . The adhesive of  claim 1 , further comprising a multivalent metal ion. 
     
     
         6 . The adhesive of  claim 5 , wherein the multivalent metal ion is aluminum, calcium, strontium, barium, titanium, chromium, manganese, iron, cobalt, nickel, zinc, molybdenum, tin, antimony, niobium, vanadium, tungsten, hafnium, zirconium, or a combination comprising at least one of the foregoing metal ions. 
     
     
         7 . The adhesive of  claim 6  wherein the multivalent metal ion is zirconium. 
     
     
         8 . The adhesive of  claim 5 , wherein n=1, X −m  is bisulfate, R 1  is ethylene, R 2  is hydrogen, and R 3  is butylene. 
     
     
         9 . The adhesive of  claim 1 , further comprising a crosslinked epi-polyamide. 
     
     
         10 . The adhesive of  claim 9 , wherein n=1, X −m  is bisulfate, R 1  is ethylene, R 2  is hydrogen, and R 3  is butylene. 
     
     
         11 . The adhesive of  claim 9 , wherein the epi-polyamide is the product formed by the reaction of an epihalohydrin with a condensation polymerization product of diethylenetriamine and adipic acid. 
     
     
         12 . The adhesive of  claim 11  wherein the epihalohydrin is epichlorohydrin. 
     
     
         13 . The adhesive of  claim 9  wherein the weight ratio of cationic non-crosslinked polyamidoamine to crosslinked epi-polyamide is 1:99 to 99:1. 
     
     
         14 . The adhesive of  claim 9  wherein a mole ratio of epichlorohydrin to secondary amine groups is from 0.05:1.0 to 2:1. 
     
     
         15 . The adhesive of  claim 1 , further comprising monoammonium phosphate. 
     
     
         16 . The adhesive of  claim 1 , further comprising a crepe release agent. 
     
     
         17 . The adhesive of  claim 1 , further comprising a plasticizer. 
     
     
         18 . The adhesive of  claim 1 , further comprising a polyvinyl alcohol. 
     
     
         19 . A method of creping paper, comprising:
 applying to a rotating cylinder a polymer solution comprising 0.1 to 10 wt % cationic non-crosslinked polyamidoamine in water, wherein the pH of the polymer prior to dilution is less than 6.9,   pressing the tissue paper web against the creping cylinder to effect adhesion of the tissue paper web to the surface of the cylinder; and   dislodging the tissue paper web from the creping cylinder by contact with a doctor blade.   
     
     
         20 . The method of  claim 19 , wherein the cationic non-crosslinked polyamidoamine has the linear repeating units 
       
         
           
           
               
               
           
         
         wherein n≧1; 
         m=1 or 2; 
         X −m  is chloride, bromide, iodide, sulfate, bisulfate, nitrate, oxalate, alkyl carboxylate, aryl carboxylate, hydrogen phosphate, dihydrogen phosphate, alkyl sulfonate, aryl sulfonate, or a combination comprising at least one of the foregoing anions; 
         R 1  is a divalent aliphatic, cycloaliphatic, or araliphatic group having from 1 to 24 carbon atoms; 
         R 2  is hydrogen or a monovalent aliphatic, cycloaliphatic, or araliphatic group having from 1 to 24 carbon atoms; and 
         R 3  is a divalent hydrocarbon radical derived from a dibasic carboxylic acid. 
       
     
     
         21 . The method of  claim 20  wherein n=1, X −m  is bisulfate, R 1  is ethylene, R 2  is hydrogen, and R 3  is butylene. 
     
     
         22 . The method of  claim 19 , wherein the polymer solution further comprises a multivalent metal ion. 
     
     
         23 . The method of  claim 22  wherein the multivalent metal ion is aluminum, calcium, strontium, barium, titanium, chromium, manganese, iron, cobalt, nickel, zinc, molybdenum, tin, antimony, niobium, vanadium, tungsten, hafnium, zirconium, or a combination comprising at least one of the foregoing. 
     
     
         24 . The method of  claim 23  wherein the multivalent metal ion is zirconium. 
     
     
         25 . The method of  claim 19 , wherein the polymer solution further comprises a crosslinked epi-polyamide. 
     
     
         26 . The method of  claim 25  wherein n=1, X −m  is bisulfate, R 1  is ethylene, R 2  is hydrogen, and R 3  is butylene. 
     
     
         27 . The method of  claim 25  wherein the epi-polyamide is the product formed by the reaction of an epihalohydrin with a condensation polymerization product of diethylenetriamine and adipic acid. 
     
     
         28 . The method of  claim 27  wherein the epihalohydrin is epichlorohydrin. 
     
     
         29 . A creped tissue produced by the process of:
 applying to a rotating cylinder a polymer solution comprising 0.1 to 10 wt % cationic non-crosslinked polyamidoamine in water, wherein the pH of the polymer prior to dilution is less than 6.9,   pressing the tissue paper web against the creping cylinder to effect adhesion of the tissue paper web to the surface of the cylinder; and   dislodging the tissue paper web from the creping cylinder by contact with a doctor blade.   
     
     
         30 . The creped tissue of  claim 29 , wherein the cationic non-crosslinked polyamidoamine has the linear repeating units 
       
         
           
           
               
               
           
         
         wherein n≧1; 
         m=1 or 2; 
         X −m  is chloride, bromide, iodide, sulfate, bisulfate, nitrate, oxalate, alkyl carboxylate, aryl carboxylate, hydrogen phosphate, dihydrogen phosphate, alkyl sulfonate, aryl sulfonate, or a combination comprising at least one of the foregoing anions; 
         R 1  is a divalent aliphatic, cycloaliphatic, or araliphatic group having from 1 to 24 carbon atoms; 
         R 2  is hydrogen or a monovalent aliphatic, cycloaliphatic, or araliphatic group having from 1 to 24 carbon atoms; and 
         R 3  is a divalent hydrocarbon radical derived from a dibasic carboxylic acid. 
       
     
     
         31 . The creped tissue of  claim 30  wherein n=1, X −m  is bisulfate, R 1  is ethylene, R 2  is hydrogen, and R 3  is butylene. 
     
     
         32 . The creped tissue of  claim 29 , further comprising a multivalent metal ion. 
     
     
         33 . The creped tissue of  claim 32  wherein the multivalent metal ion is aluminum, calcium, strontium, barium, titanium, chromium, manganese, iron, cobalt, nickel, zinc, molybdenum, tin, antimony, niobium, vanadium, tungsten, hafnium, zirconium, or a combination comprising at least one of the foregoing. 
     
     
         34 . The creped tissue of  claim 33  wherein the multivalent metal ion is zirconium. 
     
     
         35 . The creped tissue of  claim 29 , wherein the polymer solution further comprises a crosslinked epi-polyamide. 
     
     
         36 . The creped tissue of  claim 35  wherein the epi-polyamide is the product formed by the reaction of an epihalohydrin with a condensation polymerization product of diethylenetriamine and adipic acid. 
     
     
         37 . The creped tissue of  claim 36  wherein the epihalohydrin is epichlorohydrin. 
     
     
         38 . A multi-ply tissue product comprising at least two plies, wherein the plies are bonded by an aqueous polymer solution comprising:
 a cationic non-crosslinked polyamidoamine with the linear repeating units   
       
         
           
           
               
               
           
         
         
           wherein n≧1; 
           m=1 or 2; 
           X −m  is chloride, bromide, iodide, sulfate, bisulfate, nitrate, oxalate, alkyl carboxylate, aryl carboxylate, hydrogen phosphate, dihydrogen phosphate, alkyl sulfonate, aryl sulfonate, or a combination comprising at least one of the foregoing anions; 
           R 1  is a divalent aliphatic, cycloaliphatic, or araliphatic group having from 1 to 24 carbon atoms; 
           R 2  is hydrogen or a monovalent aliphatic, cycloaliphatic, or araliphatic group having from 1 to 24 carbon atoms; and 
           R 3  is a divalent hydrocarbon radical derived from a dibasic carboxylic acid. 
         
       
     
     
         39 . The multi-ply tissue product of  claim 38  further comprising a multivalent metal ion. 
     
     
         40 . The multi-ply tissue product of  claim 39  wherein the multivalent metal ion is aluminum, calcium, strontium, barium, titanium, chromium, manganese, iron, cobalt, nickel, zinc, molybdenum, tin, antimony, niobium, vanadium, tungsten, hafnium, zirconium, or a combination comprising at least one of the foregoing. 
     
     
         41 . The multi-ply tissue product of  claim 40  wherein the multivalent metal ion is zirconium. 
     
     
         42 . The multi-ply tissue product of  claim 38  wherein n=1, X −m  is bisulfate, R 1  is ethylene, R 2  is hydrogen, and R 3  is butylene. 
     
     
         43 . The multi-ply tissue product of  claim 38 , further comprising a crosslinked epi-polyamide. 
     
     
         44 . The multi-ply tissue product of  claim 43  wherein n=1, X −m  is bisulfate, R 1  is ethylene, R 2  is hydrogen, and R 3  is butylene. 
     
     
         45 . The multi-ply tissue product of  claim 43 , wherein the epi-polyamide is the product formed by the reaction of an epihalohydrin with a condensation polymerization product of diethylenetriamine and adipic acid. 
     
     
         46 . The multi-ply tissue product of  claim 45  wherein the epihalohydrin is epichlorohydrin. 
     
     
         47 . The multi-ply tissue product of  claim 43  wherein the weight ratio of cationic non-crosslinked polyamidoamine to crosslinked epi-polyamide is 1:99 to 99:1. 
     
     
         48 . A composition, comprising the acidified, aqueous reaction product of an aqueous solution comprising
 a dicarboxylic acid of the formula HO 2 C—R 3 —CO 2 H wherein R 3  is a divalent hydrocarbon radical having from 1 to 24 carbon atoms; and   a polyamine of the formula   
       
         
           
           
               
               
           
         
       
       wherein
 n is 1 to 4; 
 R 1  is a divalent aliphatic, cycloaliphatic, or araliphatic group having from 1 to 24 carbon atoms, and 
 R 2  is hydrogen or a monovalent aliphatic, cycloaliphatic, or araliphatic group having from 1 to 24 carbon atoms. 
 
     
     
         49 . An adhesive composition, comprising the acidified, aqueous reaction product of an aqueous solution comprising
 a dicarboxylic acid of the formula HO 2 C—R 3 —CO 2 H wherein R 3  is a divalent hydrocarbon radical having from 1 to 24 carbon atoms; and   a polyamine of the formula   
       
         
           
           
               
               
           
         
       
       wherein
 n is 1 to 4; 
 R 1  is a divalent aliphatic, cycloaliphatic, or araliphatic group having from 1 to 24 carbon atoms, and 
 R 2  is hydrogen or a monovalent aliphatic, cycloaliphatic, or araliphatic group having from 1 to 24 carbon atoms. 
 
     
     
         50 . The composition of  claim 49 , having a pH of 1 to 6.9. 
     
     
         51 . The composition of  claim 49 , wherein the reaction product is acidified with a mineral acid or an organic acid. 
     
     
         52 . The composition of  claim 49 , having a weight average molecular weight from 2 thousand to 1 million Daltons. 
     
     
         53 . The composition of  claim 49 , wherein the dicarboxylic acid is oxalic, L malonic, succinic, glutaric, adipic, pimelic, suberic, azelaic, sebacic, maleic, fumaric, itaconic, phthalic, isophthalic, terephthalic, or a combination comprising at least one of the foregoing acids. 
     
     
         54 . The composition of  claim 49 , wherein n=1, R 2  is ethylene, R 2  is hydrogen, and R 3  is butylene. 
     
     
         55 . The composition of  claim 49 , wherein the adhesive composition further comprises monoammonium phosphate, a crepe release agent, polyvinyl alcohol, and/or a plasticizer. 
     
     
         56 . A cationic polyamidoamine having repeating units of the structure 
       
         
           
           
               
               
           
         
         wherein n≧1; 
         m=1 or 2; 
         X −m  is chloride, bromide, iodide, sulfate, bisulfate, nitrate, oxalate, alkyl carboxylate, aryl carboxylate, hydrogen phosphate, dihydrogen phosphate, alkyl sulfonate, aryl sulfonate, or a combination comprising at least one of the foregoing anions; 
         R 1  is a divalent aliphatic, cycloaliphatic, or araliphatic group having from 1 to 24 carbon atoms; 
         R 2  is hydrogen or a monovalent aliphatic, cycloaliphatic, or araliphatic group having from 1 to 24 carbon atoms; and 
         R 3  is a divalent hydrocarbon radical derived from a dibasic carboxylic acid having from 1 to 24 carbon atoms. 
       
     
     
         57 . The polyamidoamine of  claim 56  wherein n=1, X-m is bisulfate, R 1  is ethylene, R 2  is hydrogen, and R 3  is butylene. 
     
     
         58 . An adhesive composition and use of an adhesive composition for paper manufacturing, comprising a cationic polyamidoamine of the formula P-1, P-2, P-3, or P-4: