Cleaning compositions for solid surfaces – auxiliary compositions – Auxiliary compositions for cleaning – or processes of preparing – Textile softening or antistatic composition
Reexamination Certificate
2002-04-22
2003-05-13
Hardee, John (Department: 1751)
Cleaning compositions for solid surfaces, auxiliary compositions
Auxiliary compositions for cleaning, or processes of preparing
Textile softening or antistatic composition
C510S504000, C510S499000, C554S107000, C554S110000
Reexamination Certificate
active
06562780
ABSTRACT:
DESCRIPTION
1. Technical Field
The present invention relates to novel esters derived from alkanolamines, dicarboxylic acids and fatty alcohols, and to the cationic surfactants obtainable therefrom, as well as to their use as softening agents for natural and synthetic fibres.
2. Prior Art
Cationic surfactants derived from amines have been used widely for some decades as softening and conditioning agents for natural and synthetic fibres of all types, and are used in fields such as the treatment of textile fibres and of paper and in hair hygiene products.
For ecological reasons, owing to their greater biodegradability, the use of cationic amine derivatives in which the hydrophobic hydrocarbon chains are interrupted by functional ester groups has been usual for several years, those used mostly being the quaternized derivatives of polyalkanolamine esters, generally known as esterquats, amongst which one of the types used most is esterquats derived from triethanolamine, owing to their lower cost.
It is also well known that the above-mentioned esterquats are prepared from alkanolamine esters, produced previously by an esterification reaction of the alkanolamine with fatty acids or functionalized reactive derivatives thereof, by their quaternization with alkylation agents such as alkyl halides or sulphates. There is an abundant bibliography on the subject, amongst which patents or patent applications FR-A-1593921, EP-A-239910, EP-A-295385, WO-A-9101295, DE-C-19539846 and WO-A-9849132, amongst many others, may be mentioned.
However, it is well known that esterquats are less effective softeners than their homologues which do not contain ester groups, and this has led to various technical developments directed towards improving the softening efficacy of these esterquats.
Thus, patent U.S. Pat. No. 5,593,614 describes the improvement of the softening effect of esterquats by mixing them with non-ionic surfactants, patent U.S. Pat. No. 5,501,806 proposes the mixing of esterquats with other cationic surfactants, and patent application EP-A-394133 describes the use of acrylic cationic polymers as additives for improving softness.
British patent GB-602048 describes oligomeric alkanolamine esters based on the esterification reaction of triethanolamine with dicarboxylic acids and fatty acids, as well as their quaternization with methyl chloride or dimethyl sulphate and their use as softening agents for natural and synthetic fibres, and patents U.S. Pat. Nos. 4,719,382 and 4,237,016 describe the use of the esterquats described in the above-mentioned British patent, amongst cationic polymers of many other types, as additives for improving the softening efficacy of cationic surfactants which do not contain ester groups. Moreover, patent application WO-A-9812293 describes the use of the same oligomeric esterquats as additives for incorporation in the aqueous phase of softening compositions which contain esterquats, with the object of improving their softening efficacy.
German patent DE-C-19539846 describes the synthesis of esterquats derived from dicarboxylic acids, fatty acids and triethanolamnine and their use as hair conditioners, and patent DE-C-19715835 describes esterquats based on the reaction of methyl diethanolamine and mixtures of fatty acids and dicarboxylic acids, with subsequent ethoxylation and/or quaternization.
Patent WO-A-9849132 describes the synthesis of esterquats derived from dicarboxylic acid/fatty acid/triethanolamine, within a specific selected range of proportions, and their use in fabric-softening compositions.
Lastly, patent DE-C-19519876 describes esterquats based on the reaction of a trialkanolamine with mixtures of fatty acids, dicarboxylic acids, and sorbitol and the subsequent quaternization and/or ethoxylation of the esters produced.
However, as far as the authors of the present invention know, the prior art always relates to alkanolamine esters and to their corresponding esterquats in which the hydrophobic chains result directly and mainly from the esterification of fatty acids, so that no descriptions have been found of alkanolamine esters and their corresponding esterquats in which the hydrophobic chains result mainly from fatty alcohols combined with the cationic portion of the molecule by means of a dicarboxylic-acid bridge and which, moreover, have a high degree of biodegradability and a greater softening efficacy than that of conventional esterquats.
SUMMARY OF THE INVENTION
The subject of the present invention is novel esters derived from alkanolamines, dicarboxylic acids and fatty alcohols, and the cationic surfactants obtainable therefrom.
Also included within the subject of the present invention is the use of the cationic surfactants based on the said esters derived from alkanolamines, dicarboxylic acids and fatty alcohols, particularly the esterquats obtainable therefrom, as conditioning and softening agents for natural and synthetic fibres.
Also included within the subject of the present invention are aqueous softening compositions for textile fibres containing, either as the active ingredient or as an additive for improving softening efficacy, cationic surfactants based on the said esters derived from alkanolamines, dicarboxylic acids and fatty alcohols, particularly the esterquats obtainable therefrom.
DESCRIPTION OF THE INVENTION
The alkanolamine esters of the invention are obtained by the esterification reaction of an alkanolamine of general formula (I)
with a dicarboxylic acid or with a reactive derivative thereof, of general formula (II)
HOOC—R
4
—COOH (II)
and with a fatty alcohol, optionally alkoxylated, of general formula (III)
in which formulae R
1
is hydrogen, a C
1
-C
6
alkyl group, or the residue
R
2
is a C
1
-C
6
alkylene group, R
3
is hydrogen or methyl, n is 0 or a whole number between 1 and 20, R
4
is a C
1
-C
36
alkylene group, optionally substituted or unsaturated, or an arylene group, and R
5
is a linear or branched C
2
-C
22
alkyl or alkenyl group.
Optionally, a fatty acid of general formula (IV) may also be incorporated in the reaction mixture
R
6
—COOH (IV)
in which R
6
is a linear or branched C
6
-C
23
alkyl or alkenyl group, an alkyl ester, a glyceride of the fatty acid, and/or a polyol, optionally alkoxylated.
The invention provides a cationic surfactant obtainable by the formation of the addition salt of the alkanolamine ester as above defined with mineral or organic acids.
The invention provides an esterquat obtainable by quaternization of the alkanolamine ester as above defined by the reaction with alkylation agents.
The invention besides provides a method of treating softening and/or conditioning treatment of natural or synthetic fiber, textile, paper fiber or hair fiber with the esterquats as above defined.
The invention further provides an aqueous fabric-softening composition which comprises:
(a) a surfactant or an esterquat thereof as above shown,
(b) one or a plurality of cationic surfactants active as fabric softeners,
(c) one or a plurality of non-ionic fabric-conditioning surfactants,
in which the total amount of components (a), (b) and (c) is between 2% and 60% by weight in a manner such that, with respect to the total amount of the said components (a), (b) and (c),
(i) the proportion by weight of component (a) is between 2% and 99%,
(ii) the proportion by weight of component (a) is between 0% and 98%,
(iii) the proportion by weight of component (c) is between 0% and 40%, and
(iv) the proportion by weight of the total amount of (b) and (c) is between 1% and 98%.
It is preferable that that the total amount of components (a), (b) and (c) is between 3% and 40% by weight,
(i) the proportion by weight of component (a) is between 3% and 80%,
(ii) the proportion by weight of component (b) is between 0% and 97%,
(iii) the proportion by weight of component (c) is between 0% and 30%, and
(iv) the proportion by weight of the total amount of (b) and (c) is between 20% and 97%.
DETAILED DESCRIPTION OF INVENTION
The following may be mentioned as examples of alkanolamines which may be used: tr
Bermejo María José Osés
Mumbr{overscore (u)} Marisa Tomás
Vilaret Josep Ferrer
Hardee John
Kao Corporation
Oblon & Spivak, McClelland, Maier & Neustadt P.C.
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