Process for preparing water-soluble polyhydroxyaminoether
A water soluble polymer comprising a copolyhydroxyaminoether having side-chains of polyalkylene oxides, an aqueous solution of said polymer and process for preparing the copolyhydroxyaminoether.
1. A process for preparing a water-soluble copolyhydroxyaminoether polymer having a backbone featuring amine linkages, ether linkages, and pendant hydroxyl moieties, and side chains of polyalkylene oxides, said process comprising:
reacting an amine or a mixture thereof with a diglycidyl ether of a bisphenol or a mixture thereof in a solvent including water, optionally in the presence of a nucleophile terminating agent and optionally in the presence of a catalyst;
wherein said amine or amines of said mixture have no greater than two reactive amino protons per molecule; and
wherein said amine or a portion of said amine mixture comprises a monoamino functionalized poly (alkylene oxide).
2. The process according to claim 1 wherein the nucleophile terminating agent is present and is selected from a secondary amine, hydrogen sulfide, ammonia, ammonium hydroxide, a hydroxyarene, an aryloxide salt, a carboxylic acid, a carboxylic acid salt, a mercaptan, or thiolate salt.
3. The process according to claim 2 wherein: the amine mixture, when present, comprises is ethanolamine; the monoamino functionalized poly (alkylene oxide) features the formula:
wherein R 5 is hydrocarbyl, R 6 is hydrogen, methyl, hydrocarbyl or mixtures thereof, and q is about 1 to about 1000; and the diglycidyl ether of a bisphenol or a portion of said mixture of diglycidyl ethers comprises a diglycidyl ether of bisphenol A.
4. The process according to claim 1 wherein the nucleophile terminating agent is present and is selected from diethanolamine, N-(2-hydroxyethyl)piperazine, piperadine, diethylamine, dipropylamine, or dibenzylamine.
5. The process according to claim 4 wherein: the amine mixture, when present, comprises ethanolamine; the monoamino functionalized poly (alkylene oxide) features the formula:
wherein R 5 is hydrocarbyl, R 6 is hydrogen, methyl, hydrocarbyl or mixtures thereof, and q is about 1 to about 1000; and the diglycidyl ether of a bisphenol or a portion of said mixture of diglycidyl ethers comprises a diglycidyl ether of bisphenol A.
6. The process according to claim 1 wherein the nucleophile terminating agent is present and is selected from phenol, acetic acid or propanoic acid, and the catalyst is present and is selected from a quatemary phosphonium salt or a quatemary ammonium salt.
7. The process according to claim 6 wherein: the amine mixture, when present, comprises is ethanolamine; the monoamino functionalized poly (alkylene oxide) features the formula:
wherein R 5 is hydrocarbyl, R 6 is hydrogen, methyl, hydrocarbyl or mixtures thereof, and q is about 1 to about 1000; and the diglycidyl ether of a bisphenol or a portion of said mixture of diglycidyl ethers comprises a is the diglycidyl ether of bisphenol A.
8. The process according to claim 1 wherein: the amine mixture, when present, comprises ethanolamine; the monoamino fuctionalized poly (alkylene oxide) features the formula:
wherein R 5 is hydrocarbyl., R 6 is hydrogen, methyl, hydrocarbyl or mixtures thereof, and q is about 1 to about 1000; and the diglycidyl ether of a bisphenol or a portion of said mixture of diglycidyl ethers comprises a diglycidyl ether of bisphenol A.
9. The process according to claim 1 wherein the nucleophile terminating agent is present and comprises phenol, and the catalyst is present and comprises a quaternary phosphonium salt or a guaternary ammonium salt.
10. The process according to claim 9 wherein: the amine mixture, when present, comprises ethanolamine; the monoamino functionalized poly (alkylene oxide) features the formula:
wherein R 5 is hydrocarbyl, R 6 is hydrogen, methyl, hydrocarbyl or mixtures thereof, and q is about 1 to about 1000; and the diglycidyl ether of a bisphenol or a portion of said mixture of diglycidyl ethers comprises a diglycidyl ether of bisphenol A.