Ethers

Claim 1

A METHOD FOR MAKING A WATER SOLUBLE CONDENSATION PRODUCT WHICH COMPRISES CONDENSING BY HEATING UNDER ACID CONDITIONS IN AN INERT ORGANIC SOSLVENT WHICH FORMS AN AZEOTROPIC WITHS WATER A MIXTURE OF (1) A COMPOUND CONTAINING AT LEAST TWO TERMINAL GROUPS SELECTED FROM THE CLASS CONSISTING OF N-METHYLOL GROUPS AND ETHERIFICATION PRRODUCTS OF N-METHYLOL GROUPS AND MONOHYDORXY ALCOHOLS HAVING FROM 1 TO 4 CARBON ATOMS AND (2) A POLYHYDRIC ALCOHOL SELECTED FROM THE GROUP CONSISTING OF AN HYDROXYETHYL ETHER OF PROPYLENE GLYCOL, AN HYDROXYETHYL ETHER OF BUTYLENE GLYCOL, AN HYDROXYETHYL ETHER OF PENTAMETHYLENE GLYCOL, AN HYDROXYETHYL ETHER OF HEXAMETHYLENE GLYCOL, AN HYDROXYETHYL ETHER OF GLYCERINE, AN HYDROXYETHYL ETHER OF TRIMETHYLOLPROPANE, AN HYDROXYETHYL ETHER OF PENTAERYTHRITOL, AN HYDROXYETHYL ETHER OF THIODIGLYCOL, AN HYDROXYETHYL ETHER OF 4,4''-DIHYDROXYDIPHENYLDIMETHYLMETHANE, AN HYDROXYPROPYL ETHER OF 4,4''-DIHYDORXYDIPHENYLDIMETHYLMETHANE, AN HYDROXYETHYL ETHER OF 4,4''DIHYDROXYDIPHENYL SULFONE, AN HYDROXYPROPYL ETHER OF 4,4'' DIHYDROXYDIPHENY SULFONE, AND POLYTETRAMETHYLENE ETHER GLYCOL WHILE REMOVING THE WATER OF CONDENSATION AS RAPIDLY AS IT IF FORMED BY AZEOTROPIC DISTILLATION, SAID COMPOUND HAVING N-METHYLOL GROUPS HAVING BEEN PREPARED BY REACTING AT A TEMPERATURE BELOW ABOUT 50*C., FORMALDEHYDE AND A MEMBER SELECTRED FROM THE GROUP CONSISTISNG OF UREA, THIOUREA, DIUREA, DITHIOUREA, HYDRAZODICARBONAMIDE, EHTYLENE UREA, ETHYLENE THIOUREA, AND MELAMIE, SAID COMPOUND (1) BEING SUBSTANTIALLY WATER FREE WHEN MIXED WITH SAID INERT ORGANIC SOLVENT.

Claim 2

A METHOD FOR MAKING A WATER SOLUBLE CONDENSATION PRODUCT WHICH COMPRISES CONDENSING BY HEATING UNDER ACID CONDITIONS IN AN INERT ORGANIC SOSLVENT WHICH FORMS AN AZEOTROPIC WITHS WATER A MIXTURE OF (1) A COMPOUND CONTAINING AT LEAST TWO TERMINAL GROUPS SELECTED FROM THE CLASS CONSISTING OF N-METHYLOL GROUPS AND ETHERIFICATION PRRODUCTS OF N-METHYLOL GROUPS AND MONOHYDORXY ALCOHOLS HAVING FROM 1 TO 4 CARBON ATOMS AND (2) A POLYHYDRIC ALCOHOL SELECTED FROM THE GROUP CONSISTING OF AN HYDROXYETHYL ETHER OF PROPYLENE GLYCOL, AN HYDROXYETHYL ETHER OF BUTYLENE GLYCOL, AN HYDROXYETHYL ETHER OF PENTAMETHYLENE GLYCOL, AN HYDROXYETHYL ETHER OF HEXAMETHYLENE GLYCOL, AN HYDROXYETHYL ETHER OF GLYCERINE, AN HYDROXYETHYL ETHER OF TRIMETHYLOLPROPANE, AN HYDROXYETHYL ETHER OF PENTAERYTHRITOL, AN HYDROXYETHYL ETHER OF THIODIGLYCOL, AN HYDROXYETHYL ETHER OF 4,4''-DIHYDROXYDIPHENYLDIMETHYLMETHANE, AN HYDROXYPROPYL ETHER OF 4,4''-DIHYDORXYDIPHENYLDIMETHYLMETHANE, AN HYDROXYETHYL ETHER OF 4,4''DIHYDROXYDIPHENYL SULFONE, AN HYDROXYPROPYL ETHER OF 4,4'' DIHYDROXYDIPHENY SULFONE, AND POLYTETRAMETHYLENE ETHER GLYCOL WHILE REMOVING THE WATER OF CONDENSATION AS RAPIDLY AS IT IF FORMED BY AZEOTROPIC DISTILLATION, SAID COMPOUND HAVING N-METHYLOL GROUPS HAVING BEEN PREPARED BY REACTING AT A TEMPERATURE BELOW ABOUT 50*C., FORMALDEHYDE AND A MEMBER SELECTRED FROM THE GROUP CONSISTISNG OF UREA, THIOUREA, DIUREA, DITHIOUREA, HYDRAZODICARBONAMIDE, EHTYLENE UREA, ETHYLENE THIOUREA, AND MELAMIE, SAID COMPOUND (1) BEING SUBSTANTIALLY WATER FREE WHEN MIXED WITH SAID INERT ORGANIC SOLVENT.