Organic compounds -- part of the class 532-570 series – Organic compounds – Oxygen containing
Reexamination Certificate
2002-10-07
2004-01-20
Rotman, Alan L. (Department: 1625)
Organic compounds -- part of the class 532-570 series
Organic compounds
Oxygen containing
C510S443000, C510S535000, C510S360000, C510S413000, C510S422000, C510S506000
Reexamination Certificate
active
06680412
ABSTRACT:
BACKGROUND OF THE INVENTION
1. Field of the Invention
The invention relates to alcohol alkoxylates and mixtures thereof which can be used as low-foam or foam-suppressing surfactants, for example in detergents and cleaners and in formulations for chemicotechnological applications, and to detergents and cleaners comprising them.
2. Description of the Background
Low-foam or foam-suppressing surfactants from ethoxylated and propoxylated alcohols are known per se. U.S. Pat. No. 5,766,371 relates to biodegradable low-foam surfactants which can be used as rinse aids in dishwashing detergents. It describes C
4-18
-alkanols reacted firstly with propylene oxide and then with ethylene oxide and finally with a C
4-8
-alkylene oxide.
U.S. Pat. No. 5,294,365 relates to hydroxypolyethers which can be used as low-foam surfactants. Here, C
1-18
-alcohols are firstly reacted with ethylene oxide, then with propylene oxide and then with glycidyl ethers.
U.S. Pat. No. 4,827,028 relates to anionic surfactants obtained by reacting C
1-8
-alcohols with ethylene oxide, then propylene oxide and then an alkylene oxide having at least 8 carbon atoms. The order of the reaction with propylene oxide and ethylene oxide can also be reversed.
WO 96/12001 relates to biodegradable surfactants which can be used as rinse aids. The surfactants are predominantly obtained by reacting C
4-18
-alcohols with propylene oxide, then ethylene oxide and then C
4-18
-alkylene oxides. The examples also describe the reaction of C
6-10
-alcohols with at least 20 mol of ethylene oxide and then butylene oxide or decylene oxide.
The known low-foam surfactants do not have a suitable combination of properties of foam suppression, wetting action and ability to be formulated which is suitable for all applications.
The known surfactants sometimes also have a relatively high ecotoxicological hazard potential, in particular toward aquatic organisms.
SUMMARY OF THE INVENTION
It is an object of the present invention, therefore, to provide alcohol alkoxylates which have an improved spectrum of properties and can, in particular, be used as low-foam and foam-suppressing surfactants. They should be suitable, in particular, for use in detergents and cleaners and for chemicotechnological applications.
We have found that this object is achieved according to the invention by alcohol alkoxylates of the formula (I)
R
1
—O—(CH
2
—CHR
5
—O—)
r
(CH
2
—CH
2
—O—)
n
(CH
2
—CHR
6
—O—)
s
(CH
2
—CHR
2
—O—)
m
H (I)
where
R
1
is an at least singly branched C
4-22
-alkyl
R
2
is C
3-4
-alkyl
R
5
is C
1-4
-alkyl
R
6
is methyl or ethyl
n is an average value from 1 to 50
m is an average value from 0 to 20, preferably 0.5 to 20
r is an average value from 0 to 50
s is an average value from 0 to 50,
where m is at least 0.5 if R
5
is methyl or ethyl or r is 0.
The object is also achieved according to the invention by a mixture comprising 20 to 95% by weight, preferably 30 to 95% by weight, of at least one of the above alcohol alkoxylates and 5 to 80% by weight, preferably 5 to 70% by weight, of a corresponding alcohol alkoxylate but in which R
1
is an unbranched alkyl radical with the same number of carbon atoms.
The object is also achieved by alcohol alkoxylates of the formula (II)
R
3
—(CH
2
—CH
2
—O—)
p
(CH
2
—CHR
4
—)
q
H (II)
where
R
3
is branched or unbranched C
4-22
-alkyl
R
4
is C
3-4
-alkyl
p is an average value of from 1 to 50, preferably 4 to 15
q is an average value of from 0.5 to 20, preferably 0.5 to 4, more preferably 0.5 to 2.
DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS
The object is also achieved by mixtures comprising 5 to 95% by weight of at least one branched alcohol alkoxylate (II), as described immediately above, and 5 to 95% by weight of a corresponding alcohol alkoxylate but in which an unbranched alkyl radical is present instead of a branched alkyl radical.
In the alcohol alkoxylates of the formula (I), R
2
is preferably propyl, in particular n-propyl.
In the alcohol alkoxylates of the formula (I), n preferably has an average value of from 4 to 15, particularly preferably 6 to 12, in particular 7 to 10.
m preferably has an average value of from 0.5 to 4, particularly preferably 0.5 to 2, in particular 1 to 2. The expression “average value” refers to technical-grade products in which differing numbers of alkylene oxide units may be present in the individual molecules. It describes the proportion of corresponding alkylene oxide units which are on average present in technical-grade products. A value of 0.5 therefore means that, on average, every second molecule carries a corresponding unit. Instead of the lower limit of 0.5, according to a preferred embodiment of the invention, the lower limit for the indices n, m, p and q is 1.
r is preferably 0. s is preferably 0.
The radical R
1
is preferably a C
8-15
—, particularly preferably a C
8-13
—, in particular a C
8-12
-alkyl radical which is at least singly branched. Two or more branches may also be present.
R
5
is preferably methyl or ethyl, in particular methyl.
R
6
is preferably ethyl.
The mixtures contain compounds with unbranched and with branched alcohol radicals R
1
. This is the case, for example, in the case of oxo alcohols which have a proportion of linear alcohol chains and a proportion of branched alcohol chains. For example, a C
13/15
-oxo alcohol frequently has about 60% by weight of completely linear alcohol chains, but in addition also about 40% by weight of &agr;-methyl-branched and C
≧2
-branched alcohol chains.
In the alcohol alkoxylates of the formula (II), R
3
is preferably a branched or unbranched C
8-5
-alkyl radical, particularly preferably a branched or unbranched C
8-13
-alkyl radical and in particular a branched or unbranched C
8-12
-alkyl radical.
R
4
is preferably propyl, in particular n-propyl. p preferably has an average value of from 4 to 15, particularly preferably an average value of from 6 to 12 and in particular an average value of from 7 to 10. q preferably has an average value of from 0.5 to 4, particularly preferably 0.5 to 2, in particular 1 to 2.
Analogously to the alcohol alkoxylates of the formula (I), the alcohol alkoxylates of the formula (II) can also be present as mixtures containing unbranched and branched alcohol radicals.
Suitable alcohol components on which the alcohol alkoxylates according to the invention are based are not only pure alkanols, but also homologous mixtures with a range of carbon atoms. Examples are C
8/10
-alkanols, C
10/12
-alkanols, C
13/15
-alkanols, C
12/15
-alkanols. Mixtures of two or more alkanols are also possible.
The above alkanol alkoxylates or mixtures according to the invention are preferably prepared by reacting alcohols of the formula R
1
—OH or R
3
—OH or mixtures of corresponding branched and unbranched alcohols optionally firstly with C
3-6
-alkylene oxide, then with ethylene oxide and subsequently optionally with C
3-4
-alkylene oxide and then a corresponding C
5-6
-alkylene oxide. The alkoxylations here are preferably carried out in the presence of alkoxylation catalysts. Use is made here in particular of basic catalysts, such as potassium hydroxide. Using special alkoxylation catalysts, such as modified bentonites or hydrotalcites, as are described, for example, in WO 95/04024, the random distribution of the amounts of incorporated alkylene oxides can be severely restricted, giving “narrow-range” alkoxylates. As a result, the random distribution of the amount of alkylene oxide units in technical-grade mixtures can be severely restricted.
The alcohol alkoxylates or mixtures thereof according to the invention are preferably used in accordance with the invention as low-foam or foam-suppressing surfactants.
The low-foam or foam-suppressing surfactants according to the invention can be used in a large number of applications. They are preferably used as nonionic surfactants, preferably in detergent and cleaner formulations and in surfactant-containing formulations for chemicotechnological applications, for example for industrial and domestic cleaning processes, and for tex
aus dem Kahmen Martin
Gümbel Helmut
Taeger Klaus
Wagner Norbert
BASF - Aktiengesellschaft
Oblon, Spivak, McClelland, Maier & Neustadt PC
Reyes Hector M.
Rotman Alan L.
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