Acylated polymeric polyamines

Details Acylated polymeric polyamines Acylated polymeric polyamines

1999-12-30

2003-06-17

Boyer, Charles (Department: 1751)

Cleaning compositions for solid surfaces, auxiliary compositions

Cleaning compositions or processes of preparing

Specific organic component

C510S470000, C510S480000, C510S130000

Reexamination Certificate

active

06579846

ABSTRACT:

The present invention relates to acylated polymeric polyamines, to their use as thickeners, and to aqueous compositions which comprise these polyamines.
Thickeners are used widely to increase the viscosity of aqueous preparations, for example in the field of pharmacy and cosmetics. Examples of common thickeners are fatty acid polyethylene glycol monoesters, fatty acid polyethylene glycol diesters, fatty acid alkanolamides, ethoxylated fatty alcohols, ethoxylated glycerol fatty acid esters, cellulose ethers, sodium alginate, polyacrylic acids, and neutral salts.
The use of the known thickeners is, however, associated with disadvantages, depending on the preparation to be thickened. For example, it is possible that the thickening action and the salt stability of the thickener are unsatisfactory, that their use is undesired, and that their incorporation into the preparation to be thickened is hindered.
EP-A-0 336 901 describes a two-phase medicinal skincare composition for increasing the moisture content of the skin. As a nonionic surface-active agent, this can have an acylated polyethyleneimine containing C
12
- to C
18
-acyl radicals.
FR-A-2 164 801 describes a polyethyleneimine which has been partially formylated with ethyl formate, and its use in cosmetic compositions.
JP-A-09 157 113 describes polyethyleneimines acylated with fatty acids and their use as bacteriostatics, e. g. in cosmetic formulations.
An object of the present invention is to provide a novel thickener. This should be suitable for aqueous formulations, preferably for cosmetic compositions. Preferably, it should be useful for surfactant-containing compositions, in particular for compositions which comprise an alkyl or alkenyl polyglycoside.
Surprisingly, we have found that this object is achieved by acylated polymeric polyamines in which some of the polyamine nitrogen atoms have at least one long-chain C
8
- to C
28
-acyl radical, and some of the other polyamine nitrogen atoms have at least one short-chain C
1
- to C
7
-acyl radical.
The present invention therefore relates to acylated polymeric polyamines, where
a) some of the polyamine nitrogen atoms carry acyl radicals of the formula I
R
1
—CO—  (I)
 in which
R
1
is selected from C
7
- to C
27
-alkyl, C
7
- to C
27
-alkenyl and C
7
- to C
27
-hydroxyalkyl, and
b) some of the polyamine nitrogen atoms carry acyl radicals of the formula II
R
2
—CO—  (II)
 in which
R
2
is selected from hydrogen, C
1
- to C
6
-alkyl and C
1
- to C
6
-hydroxyalkyl.
For the purposes of the present invention, the term C
1
- to C
6
-alkyl includes straight-chain and branched alkyl groups. These include, in particular, methyl, ethyl, n-propyl, isopropyl, n-butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, n-hexyl. Preference is given to straight-chain and branched C
1
- to C
3
-alkyl groups.
C
1
- to C
6
-hydroxyalkyl is a C
1
- to C
6
-alkyl radical being substituted with 1 or 2 hydroxyl groups, e. g. 1-, 2- or 3-hydroxypropyl, 1-, 2-, 3- or 4-hydroxybutyl or 1-, 2-, 3-, 4- or 5-hydroxypentyl, especially 3-hydroxypropyl or 5-hydroxypentyl.
The term C
7
- to C
27
-alkyl includes straight-chain and branched alkyl groups. These are preferably straight-chain and branched C
9
- to C
25
-alkyl, particularly preferably C
10
- to C
22
-, and especially C
11
- to C
19
-alkyl groups. Preference is given in this connection to predominantly linear alkyl radicals, as also occur in natural or synthetic fatty acids and fatty alcohols, and also oxo alcohols. These include, in particular, n-octyl, ethylhexyl, 1,1,3,3-tetramethylbutyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl, n-tridecyl, myristyl, pentadecyl, palmityl (═cetyl), heptadecyl, octadecyl, nonadecyl, arachidyl, behenyl, lignocerenyl, cerotinyl, melissinyl etc.
C
7
- to C
27
-alkenyl preferably stands for straight-chain and branched alkenyl groups which can be mono-, di- or polyunsaturated. Preference is given to C
9
- to C
25
-, in particular C
10
- to C
22
-, and especially C
11
- to C
19
-alkenyl groups. These include, in particular, octenyl, nonenyl, decenyl, undecenyl, dodecenyl, tridecenyl, tetradecenyl, pentadecenyl, hexadecenyl, heptadecenyl, octadecenyl, nonadecenyl, linolyl, linolenyl, elaostearyl etc.
C
1
- to C
27
-hydroxyalkyl is derived from the before mentioned C
1
- to C
27
-alkyl radicals which contain one, two, three or four, especially one or two hydroxyl groups; e. g. 10-hydroxydecyl, 11-hydroxyheptadecyl, 8,9-bishydroxyheptadecyl and 3-hydroxyheptadecyl.
Preferably, the radicals R
1
and R
2
have a difference in the number of carbon atoms of at least 4, in particular at least 6 and especially at least 10.
Preferably, the radical R
1
is a C
7
- to C
27
-alkyl radical or a C
7
- to C
27
-alkenyl radical.
Preferably, the radical R
2
is hydrogen or a C
1
- to C
6
-alkyl radical.
Especially, the radical R
1
is an alkyl radical derived formally from capric acid, lauric acid, myristic acid, palmitic acid, stearic acid, isostearic acid, oleic acid, linoleic acid, arachidonic acid, erucic acid, behenic acid, and mixtures thereof, by removal of the carboxylic acid group.
Especially, the radical R
2
is hydrogen, methyl, ethyl, n-propyl, and mixtures thereof.
Preferably, from about 0.3 to 40%, preferably from 0.6 to 25%, in particular from 1 to 15%, of the polyamine nitrogen atoms have an acyl radical of the formula I. Specifically, at least 1.5%, more specifically at least 2.5%, of the polyamine nitrogen atoms have an acyl radical of the formula I. The percentages refer in this case to the nitrogen atoms of the polyamine overall, i.e. to the total of primary, secondary and, if present, tertiary amine nitrogens.
Preferably, from about 5 to 100%, more preferably from 15 to 90%, in particular from 30 to 85%, specifically from 40 to 80%, of the polyamine nitrogens have been acylated. The degree of acylation refers in this case to the sum of acyl radicals of the formulae I and II.
The acylated polymeric polyamines according to the invention are obtainable by reaction of at least one polyamine, preferably at least one polyalkylenepolyamine, in particular at least one polyethyleneimine, with at least one long-chain carboxylic acid or a derivative thereof, and at least one short-chain carboxylic acid or a derivative thereof.
The invention further relates to a process for the preparation of acylated polymeric polyamines as defined above, where a polymeric polyamine is reacted with
a) at least one carboxylic acid of the formula I.1
R
1
—COOH  (I.1)
 in which
R
1
is selected from C
7
- to C
27
-alkyl, C
7
- to C
27
-alkenyl and C
7
- to C
27
-hydroxyalkyl,
or an ester, anhydride or halide thereof, and
b) at least one carboxylic acid of the formula II.1
R
2
—COOH  (II.1)
 in which
R
2
is selected from hydrogen, C
1
- to C
6
-alkyl and C
1
- to C
6
-hydroxyalkyl,
or an ester, anhydride, lactone or halide thereof.
Suitable polymeric polyamines are linear or branched polymers, preferably branched polymers. These preferably have acylatable secondary amino groups in the polymer chain. Additionally, these polymers can have terminal, primary amino groups and/or tertiary amino groups in the polymer chain.
According to a suitable embodiment, the amidatable polyalkylenepolyamines can have a strictly linear or essentially linear construction. Such polymers then exclusively or essentially have primary and secondary amino groups. Preference is given to using polyalkylenepolyamines which are branched. Here, the polyamine nitrogen atoms include not only primary and secondary, but also tertiary amino groups. The latter are not accessible to a reaction in an amidation reaction. Preference is given to using a polyalkylenepolyamine having a weight-average molecular weight of from about 500 to 1,000,000, preferably from about 1000 to 800,000, more preferably from 1500 to 200,000, in particular from 2000 to 50,000. Preferred polyalkylenepolyamines are, for example, polyethyleneimines.
Suitable polyethyleneimines are obtainable by

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