Succinic acid derivatives and their use as surfactants

Cleaning compositions for solid surfaces – auxiliary compositions – Cleaning compositions or processes of preparing – Specific organic component

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544 36, C11D 166

Patent

active

057983313

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BRIEF SUMMARY
This invention relates to surfactants and in particular to novel surfactants based on derivatives of substituted succinic acids and to the use of these surfactants particularly as adjuvants in agrochemical formulations and as dispersants and/or emulsifiers in agrochemical, as dispersants for pigments, especially in aqueous dispersions, as emulsifiers in emulsion polymerisation, as surfactants in domestic detergents, particularly heavy duty laundry liquids, especially non-aqueous heavy duty laundry liquids, and other applications.
In recent years there has been an increasing desire to replace well established surfactants with materials of increased biodegradability. There is, however, great practical difficulty in devising alternatives to substances of excellent performance which have maintained an important position in the market for several decades.
EP 0107199 B and published PCT Application No WO 94/00508 A describe surfactants based on alk(en)yl substituted succinic acid alkylene oxide esters and amides.
This invention is based on the discovery of substituted di-amides or amide esters of alkenyl succinic acids, particularly where the amide group is a glucamide group. These compounds have particular utility as surfactants and/or adjuvants in agrochemical formulations; as dispersants for pigments e.g. in aqueous dispersions of pigments, especially TiO.sub.2, particularly for use in paints; and as surfactants in laundry formulations, especially heavy duty laundry formulations.
This invention accordingly provides compounds of the formula (I): ##STR2## where one of R.sup.1 and R.sup.2 in the succinic acid moiety is C.sub.6 to C.sub.22 alkenyl or alkyl and the other is hydrogen; to C.sub.20 alkyl, C.sub.7 to C.sub.12 aralkyl, C.sub.2 to C.sub.20 hydroxyl substituted alkyl e.g. ethanoyl (2-hydroxyethyl), or R.sup.4 is independently as defined above for R.sup.3 ; independently as defined above; or non-integral); and to C.sub.20 alkyl, especially C.sub.1 to C.sub.6 alkyl such as methyl, ethyl, propyl or butyl; or ##STR3## where R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are independently as defined above: or to C.sub.20 alkyl, especially C.sub.1 to C.sub.6 alkyl such as methyl, ethyl, propyl or butyl; C.sub.20 alkyl, especially C.sub.1 to C.sub.6 alkyl such as methyl, ethyl, propyl or butyl; or or a N--(C.sub.1 to C.sub.6 alkyl) piperazino- group; or hydrocarbyl group, particularly an alkyl group; or CH.sub.2.OR.sup.10 C.sub.20 alkyl, especially C.sub.1 to C.sub.6 alkyl such as methyl, ethyl, propyl or butyl; or ##STR4## where R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are independently as defined above.
The following particular sub-groups of compounds of the formula (I) form specific aspects of the invention: ##STR5## where R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are independently as defined above and the respective groups --NR.sup.3 R.sup.4 are desirably, but not necessarily, the same. ##STR6## where R.sup.1, R.sup.2, R.sup.3, R.sup.4, AO, n and R.sup.6 are as defined above. ##STR7## where R.sup.1, R.sup.2, NR.sup.3 R.sup.4, AO and n are as defined above and the respective groups R.sup.1 /R.sup.2 and --NR.sup.3 R.sup.4 are desirably, but not necessarily, the same. ##STR8## where R.sup.1, R.sup.2, R.sup.3, R.sup.4, AO, n and R.sup.9 are as defined above. ##STR9## where R.sup.1, R.sup.2, R.sup.3, R.sup.4, AO and p are as defined above and the respective groups R.sup.1 /R.sup.2 and --NR.sup.3 R.sup.4 are desirably, but not necessarily, the same. ##STR10## where R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.7 and R.sup.8 are as defined above.
Among the compounds of the invention, those where the alk(en)yl group R.sup.1 /R.sup.2 is a C.sub.8 to C.sub.18 alkenyl or alkyl group are especially desirable. Similarly, compounds where the group R.sup.1 or R.sup.2 is an alkenyl group are more desirable than those where the group is alkyl. Compounds where the group R.sup.1 or R.sup.2 is an alkenyl group, particularly a C.sub.8 to C.sub.18 alkenyl group form a specific aspect of the invention. It is desirable that the R.sup.1 /R.sup.2 alkyl

REFERENCES:
patent: 3707511 (1972-12-01), Vincent et al.
patent: 3991056 (1976-11-01), Okamoto et al.
patent: 5559232 (1996-09-01), Ackermann et al.
patent: 5620952 (1997-04-01), Fu et al.
Chemical Abstracts, vol. 119, No. 17, Oct. 25, 1993, Columbus, Ohio, US: Abstract No. 180393, Fujio A. et al. `Preparation of alkyl-or alkenylsuccinic acid ester derivatives as surfactants with low irritability` see abstract & JP,A,93 125 014 (Kao Corp; Japan) May 21, 1993.

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