Patent GB-1422139-A (GB)
Title: Production and use of surface active agents
IPC: C09K23/22
Filed: 1972-12-20
Abstract: 1422139 Polyetheramides CHEMISCHE FABRIK PFERSEE GmbH 20 Dec 1972 [28 Dec 1971 25 Aug 1972] 58959/72 Heading C2C [Also in Divisions C3 and D1-D2] Novel surface-active agents comprise compounds of the formula CHOHCH 2 ) x -B, wherein A denotes x denotes 0 or 1, when x=0 B represents H and when x = 1 B represents -A, -OR<SP>6</SP> or -OH, R<SP>1</SP> denotes a saturated or mono-unsaturated C 9-17  alkyl group optionally substituted by a hydroxyl group, R<SP>2</SP> denotes H when x = 0 and H or -OH when x = 1, R<SP>3</SP> denotes C 1-4  alkyl, -CH 2 CH 2 OH, or R<SP>4</SP> denotes H or -CH 3 , R<SP>5</SP> denotes H or -OH, R<SP>6</SP> denotes C 1-4  alkyl, m denotes 6 to 30 when x = 0 and R<SP>3</SP> denotes C 1-4  alkyl, -CH 2 CH 2 OH or -CH 2 CH(OH)CH 3 , 4 to 16 when x = 0 and R<SP>3</SP> denotes or and 4 to 30 when x = 1, n denotes 0 or 1, p denotes 2 to 14, provided that the sum (m +p) is less than or equal to 32, and q denotes 0 or 1. The above compounds are prepared (a) by reacting a fatty acid amide A-H with an equimolar quantity of a chlorhydrin monoether ClCH 2 CHOHCH 2 -(OC 2 H 4 ) m -OH and optionally with a further mole of such chlorohydrin monoether to convert R<SP>3</SP> = -CH 2 CH 2 OH or -CH 2 CH(OH)CH 3  into or respectively, and (b) by reacting A-H with an equimolar quantity of a bis-chlorohydrin ether followed by reaction with a mole of B-H, where B-H may represent A-H (and in which ease may be reacted simultaneously with the first mole of A-H) as well as the other values given, and the products are optionally further reacted with chlorohydrin monoether to convert R<SP>3</SP> radicals as under (a). In each case final adjustment of the pH to the range 3 to 10 is made by the addition of acid or base. In examples (1) C 17 H 33 CONHCH 2 CH 2 CH 2 NHCH 2 CH 2 OH or C 17 H 33 CONHCH 2 CH 2 NHCH 2 CH 2 OH is reacted with a 1 : 1 adduct of epichlorohydrin and polyglycol 600, the product boiled with KOH and acidified to a pH of 6À8; (2) products analogous to (1) but based on ricinoleic acid instead of oleic acid are prepared; (3) C 11 H 33 CONHCH 2 CH 2 NHCH 2 CH 2 OH or analogous compounds in which the louric acid radical is replaced by a palmitic acid radical are reacted with a 1À2 : 1 adduct of epichlorohydrin and polyglycol 400 and treated as in (1); (4) the recinoleic acid amide of N-ethyl- 1,3-propylene diamine or the stearic acid amide of N-methyl-ethylene diamine are reacted with a 1 : 1 adduct of epichlorohydrin and polyglycol 1000 and treated as in (1); (5) C 11 H 23 CONHCH 2 CH 2 NHCH 2 CH 2 OH is reacted with the bis-chlorohydrin ether of polyglycol 400 and treated with boiling KOH and subsequently ethylene glycol and KOH before adjusting to pH 6À6; (6) as in (5) but starting with C 17 H 33 CONHCH 2 CH 2 NHCH 2 CH 2 OH and treating with polyethylene glycol 300 in place of ethylene glycol; (7) C 11 H 23 -CONHCH 2 CH(OH)CH 2 NHCH 2 CH 2  OH is reacted with the bis-chlorohydrin ether of polyethylene glycol 1000 and treated with NaOH before adjusting to pH 6À5; (8) C 17 H 33 CONHCH 2 CH 2 NHCH 2 CH 2 OH are reacted with the bis-chlorohydrin ether of polyglycol 600 and treated with boiling KOH and subsequently 1,2-propylene glycol and KOH before adjusting to pH 7À5; (9) the ricinoleic acid amide of N-ethyl-1,3-propylene diamine is reacted with the bis-chlorohydrin ether of polyglycol 1350 and treated with NaOH and subsequently 1,3-butylene glycol and NaOH; (10) a mixture of an oleic acid amide starting material as in (6) and the analogous stearic acid amide is reacted with a bis-chlorohydrin ether of polyethylene glycol 200 and treated with KOH and subsequently polyglycol 600 and KOH prior to adjusting to pH 6À5; (11) as in (10) but replacing the polyglycol 600 by glycerol; (12) equimolar quantities of oleic acid and betahydroxyethyl-1,3-propylene diamine are condensed together to provide a starting amide of the formula C 17 H 33 CONHCH 2 CH 2 CH 2 NHCH 2 CH 2 OH which is reacted with the bis-chlorohyrdin ether of polyglycol 800 and treated with KOH prior to adjusting to a pH of 6À0; (13) the palmitic acid amide of N-beta-hydroxypropyl ethylene diamine is reacted with the bischlorohydrin ether of polyglycol 200 and NaOH to provide a product with a chlorohydrin group which is subsequently reacted with ethanol/ NaOH and adjusted to a pH of 5À5; (14) the oleic acid amide of N-methyl ethylene diamine is reacted with the bis-chlorohydrin ether of polyglycol 600 and the residual chlorohydrin groups saponified with KOH prior to adjusting to pH 7À5; (15) and (16) the oleic acid amide of formula C 17 H 33 CONHCH 2 CH 2 NHCH 2 CH 2 OH is reacted with the bis-chlorohydrin ether of polyglycol 600 and treated with KOH and subsequently ethylene glycol and KOH, and the product is then further reacted with the chlorohydrin ether of polyglycol 600 and treated with KOH. Uses.-As pre-cleaning or pro-washing agents for fabrics prior to water-repellent treatment, as waterproofing agents for fabrics in conjunction with crease-resisting agents and other waterproofing agents, as emulsifiers for emulsions based on polyethylene, water and KOH (Example 1), stearamide and water (Example 2), hydrogen methyl polysiloxanes (Example 4) and mixtures of zirconium salts and paraffin (Example 10).