W. R. Grace Co.

John Leonard Ohlson

Roger R Gaudette

Patricia M Scanlon

Irving E Isgur

A polyurethane polymer amine salt is used as a dyeing aid by pretreating a woven or non-woven textile material containing at least partially or wholly synthetic textile materials or by incorporating a solution of the polyurethane polymer amine salt into the dyeing bath.

Polyurethane polymer amine salt as a dyeing aid, particularly for

A process for preparing in high yield an isolable orthohydroxydiaminodicarboxylic acid which is useful as a metal chelating agent. The process comprises reacting a phenol (or mixture of phenols), a diaminodicarboxylic acid (or acid source), and a formaldehyde source in a medium having an acidic pH.

Process for preparing chelating agents

A novel chelating agent having the formula ##STR1## (a) each of X.sub.1, X.sub.2, X.sub.3, and X.sub.4 is a member selected from the group consisting of (i) hydrogen; (ii) an alkyl group having 1-4 carbon atoms; (iii) --CN; (iv) --SO.sub.3 M.sub.1 ; (v) --COOM.sub.1 ; (vi) --OM.sub.3 ; (vii) --NO.sub.2 ; (viii) --OH; and ##STR2## in which each of R.sub.1 and R.sub.2 is an alkyl group having 1-4 carbon atoms;

N,N'Di(hydroxybenzyl) 1,3-propanediamine N,N'-diacetonitriles

An iron, copper, cobalt, manganese, chromium, nickel, zinc, cadmium, molybdenum, or lead chelate of a novel chelating agent having the formula ##STR1## in which (A) EACH OF X.sub.1, X.sub.2, X.sub.3, and X.sub.4 is a member selected from the group consisting of (i) hydrogen; (ii) an alkyl group having 1-4 carbon atoms; (iii) --CN; (iv) --SO.sub.3 M.sub.1 ; (v) --COOM.sub.1 ; (vi) --OM.sub.3 ; (vii) --NO.sub.2 ; (viii) --OH; and ##STR2## IN WHICH EACH OF R.sub.1 and R.sub.2 is an alkyl group having 1-4 carbon atoms;

Metal chelates

A novel chelating agent having the formula ##STR1## in whichA. EACH OF X.sub.1, X.sub.2, X.sub.3, and X.sub.4 is a member selected from the group consisting of (i) hydrogen; (ii) an alkyl group having 1-4 carbon atoms; (iii) --CN; (iv) --So.sub.3 M.sub.1 ; (v) --COOM.sub.1 ; (vi) --OM.sub.3 ; (vii) --NO.sub.2 ; (viii) --OH; and (ix) ##STR2## in which each of R.sub.1 and R.sub.2 is an alkyl group having 1-4 carbon atoms;

N,N-di-(hydroxybenzyl)-trimethylene diaminediacetic acids

N,N'-Dicarboxymethyl-1,3-propanediamine (designated PDDA) is prepared by reacting 1,3-propanediamine with formaldehyde and HCN to form hexahydropyrimidine-1,3-diacetonitrile, which is hydrolyzed with an aqueous alkali metal hydroxide to form dialkali metal hexahydropyrimidine-1,3-diacetate which, in turn, is reacted with mineral acid to form the desired PDDA and formaldehyde. N,n'-dicarboxymethyl-2-hydroxy-1,3-propanediamine (designated HYDROXY-PDDA) is prepared by reacting 1,3-diamino-2-propanol with formaldehyde and HCN to form 5-hydroxyhexahydropyrimidine-1,3-diacetonitrile, which is hydrolyzed with an aqueous alkali metal hydroxide to form dialkali metal 5-hydroxyhexahydropyrimidine-1,3-diacetate which, in turn, is reacted with acid to form the desired HYDROXY-PDDA and formaldehyde.

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Bedford, MA, United States of America

John Leonard Ohlson