Cleaning compositions for solid surfaces – auxiliary compositions – Cleaning compositions or processes of preparing – Specific organic component
Reexamination Certificate
2000-02-25
2002-08-13
Boyer, Charles (Department: 1751)
Cleaning compositions for solid surfaces, auxiliary compositions
Cleaning compositions or processes of preparing
Specific organic component
C510S238000, C510S245000, C510S259000, C510S362000, C510S365000, C510S421000, C510S504000
Reexamination Certificate
active
06432907
ABSTRACT:
FIELD OF THE INVENTION
The present invention relates to cationic sugar surfactants with improved biodegradability that can be used as hydrotropes for surfactants, especially for nonionic alkylene oxide adducts in alkaline solutions, and as cleaners for hard surfaces. They are obtained from ethoxylated quaternary ammounium compounds and reducing saccharides or alkyl glycosides.
BACKGROUND OF THE INVENTION
Surface active nonionic alkylene oxide adducts are widely used as essential degreasing and/or dispersing components in alkaline cleaning compositions. Their solubility in cleaning composition concentrates is, however, limited in the presence of high amounts of electrolytes, such as alkali and/or alkaline complexing agents.
It is prior known that cationic surfactants, such as ethoxylated fatty amines (about 14-20 moles ethylene oxide per mol fatty amine) that have been quaternized by an alkylating agent, e.g. methyl chloride or dimethyl sulfate, are excellent hydrotropes for nonionic alkylene oxide adducts and are also good cleaners themselves. However, from an environmental point of view they are less desirable, since they are not readily biodegradable.
The main purpose of the present invention is to provide products that are excellent hydrotropes for surfactants.
Another purpose is to provide hydrotropes with improved biodegradability over the prior used cationic surfactants.
Still another purpose is to provide hydrotropes which contribute to the cleaning performance of the surfactants.
It has now been found that said main purpose is achieved by using, as a hydrotrope a cationic sugar surfactant containing at least one hydrocarbon group with 6-24 carbon atoms and at least one quaternary ammonium group where at least one substituent is an alkyleneoxy containing group which is connected to a saccharide residue by a glycosidic bond.
SUMMARY OF THE INVENTION
The present invention generally relates to a cationic sugar surfactant containing at least one hydrocarbon group with 6-24 carbon atoms and at least one quaternary ammonium group where at least one substituent is an alkyleneoxy containing group which is connected to a saccharide residue by a glycosidic bond, and more particularly, the use of said sugar surfactant as a hydrotrope for surfactants.
DETAILED DESCRIPTION OF THE INVENTION
In accordance with the present invention, new hydrotropes which contribute to the cleaning performance of the surfactants have been found. These hydrotropes comprise a cationic sugar surfactant containing at least one hydrocarbon group with 6-24 carbon atoms and at least one quaternary ammonium group where at least one substituent is an alkyleneoxy containing group which is connected to a saccharide residue by a glycosidic bond.
Preferably the substituent has the formula (AO)
s
(G)
g
where AO is an alkyleneoxy group with 2-4 carbon atoms, G is a saccharide residue, g is a number from 1 to 10 and s is a number from 1 to 12.
The cationic sugar surfactant according to the invention may be produced by reacting
a) an amine compound containing at least one hydrocarbon group with 6-24 carbon atoms and at least one quaternary ammonium group, where at least one substituent is a hydroxyalkyl containing group, and
b) a reducing saccharide or an alkyl glycoside where the alkyl group has 1-8 carbon atoms, at least partially in the presence of an acid. The substituent attached to the quaternary ammonium group has preferably the formula (AO)
s
(G)
g
, where AO is an alkyleneoxy group with 2-4 carbon atoms, G is a saccharide residue, g is a number from 1 to 10 and s is a number from 1 to 12.
Suitable sugar surfactants according to the invention have the formula
where R is an aliphatic group with 6-24, preferably 8-20 carbon atoms; R
1
is an aliphatic group with 1-4 carbon atoms or (AO)
s
(G)
p
; R
2
, R
3
and R
4
are a group (AO)
s
(G)
p
, an aliphatic group with 1-24 carbon atoms or a hydroxyalkyl group with 2-4 carbon atoms; AO is an alkyleneoxy group with 2-4 carbon atoms; s is 0-12, preferably 1-6 and &Sgr; s=1-25, preferably 3-15; G is a saccharide residue which is connected to the rest of the molecule by a glycosidic bond and p (the degree of polymerisation) is 0-10 and &Sgr; p=1-20; r=0-3; y=2-3; X=CO or COO(AO)
t
(C
q
H
2q
) or O(AO)
t
(C
q
H
2q
); n=0 or 1; n
1
is 0 except when X is CO, then n
1
is 1; q=2-4; t=0-2; u=0 or 1 and v=0 or 1, provided that the sum (v+&Sgr; u) is 1-3, preferably 1; Z is an anion, preferably a monovalent anion, such as Cl
−
or methyl sulphate and z is the charge of the anion Z. The nitrogen atoms where u or v is 1 are quaternary and thus have a permanent positive charge. These cationic sugar surfactants have, in comparison with the prior known cationic hydrotropes, an essentially improved biodegradability. They are also comparable or better hydrotropes for surfactants, especially nonionic alkoxylates, and combine the improved biodegradability and good hydrotropy with a surprisingly large contribution to the cleaning performance of cleaning compositions as well as a valuable dispersing effect.
The product (I) can be produced by reacting a) a reducing saccharide or an alkyl glycoside and b) a quaternary ammonium compound having the formula
where R
6
is independently an aliphatic group with 1-4 carbon atoms or —CH
2
CH
2
OH; R
7
, R
8
and R
9
independently are a group (AO)
s
, an aliphatic group with 1-24 carbon atoms or a hydroxyalkyl group with 2-4 carbon atoms; 1=0 or 1 and k=0 or 1, provided that the sum (k+&Sgr; 1) is 1-3, preferably 1; and R, AO, s, X, n, n
1
, y and r have the same meaning as in formula I. The nitrogen atoms where k or l is 1 are quaternary and thus have a permanent positive charge. Since compounds II are rather hydrophobic due to a limited number of oxyethylene units, they exhibit no or only limited hydrotropic effects. Also the cleaning ability of compounds having the formula II is poor. The obtained reaction mixture contains essential amounts of both the cationic sugar surfactant I and the quaternary ammonium compound II. This product mixture can advantageously be used without any purification as a hydrotrope. Normally the ratio between the cationic sugar surfactant I and the quaternary ammonium compound II is from 1:3 to 9:1.
Suitable examples of the cationic sugar surfactants and the quaternary ammonium compounds are those having the formulae
where R is an aliphatic group with 6-24, preferably 8-20 carbon atoms; R
1
is an aliphatic group with 1-4 carbon atoms or the group C
2
H
4
O(G)
p
; G is a saccharide residue that is connected to the polyethyleneoxy chain by a glycosidic bond and p (the degree of polymerisation) is 0-10, preferably 0-5, &Sgr; p being 1-15, preferably 1-8; EO is an ethyleneoxy group; s is 0-12; &Sgr; s is 2-15, preferably 5-12; Z and z have the meaning mentioned in formula I and
where R, R
1
, EO, z, Z and s have the same meaning as in formula III except that p in the group R
1
is 0, respectively.
Suitable examples of hydrophobic groups R in formula 1-IV are: hexyl, 2-ethylhexyl, octyl, decyl, cocoalkyl, lauryl, oleyl, rape seed alkyl and tallow alkyl.
The cationic sugar surfactants III are easily produced by reacting a reducing saccharide and the quaternary ammonium compound of formula IV. The reaction mixtures containing essential amounts of both compound III and IV are preferably used as hydrotropes without any separation of the compounds, mainly because such a separation is a costly operation. The relation between cationic sugar surfactant and the quaternary ammonium compound could vary between 1:3 and 9:1, preferably between 2:3 and 9:1.
Cationic surfactants containing sugar residues are known by the publications DE 4 413 686 and JP 4-193891. In DE 4 413 686 surfactants containing quaternary ammonium groups are prepared by reacting glycosides with quaternary halogenated compounds or quaternary epoxy compounds. The linkage between the sugar residue and the cationic part is an ether linkage. The products could als
Gustavsson Bodil
Skold Rolf
Akzo Nobel N.V.
Boyer Charles
Mancini Ralph J.
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