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Patent 2801643 Summary

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(12) Patent Application: (11) CA 2801643
(54) English Title: ALKOXYLATES AND THE USE THEREOF
(54) French Title: ALCOXYLATES ET LEUR UTILISATION
Status: Deemed Abandoned and Beyond the Period of Reinstatement - Pending Response to Notice of Disregarded Communication
Bibliographic Data
(51) International Patent Classification (IPC):
  • C11D 1/44 (2006.01)
(72) Inventors :
  • KLINGELHOEFER, PAUL (Germany)
  • TROPSCH, JUERGEN (Germany)
  • KAHL, ROLF-DIETER (Germany)
  • SENF, ANDREAS (Germany)
(73) Owners :
  • BASF SE
(71) Applicants :
  • BASF SE (Germany)
(74) Agent: ROBIC AGENCE PI S.E.C./ROBIC IP AGENCY LP
(74) Associate agent:
(45) Issued:
(86) PCT Filing Date: 2011-06-21
(87) Open to Public Inspection: 2012-01-05
Examination requested: 2016-06-20
Availability of licence: N/A
Dedicated to the Public: N/A
(25) Language of filing: English

Patent Cooperation Treaty (PCT): Yes
(86) PCT Filing Number: PCT/EP2011/060360
(87) International Publication Number: WO 2012000845
(85) National Entry: 2012-12-05

(30) Application Priority Data:
Application No. Country/Territory Date
10167459.6 (European Patent Office (EPO)) 2010-06-28

Abstracts

English Abstract

The invention relates to the use of a 2-propyl-heptyl amine-based alkoxylate, which is alkoxylated with ethylene oxide, propylene oxide, butylene oxide, pentylene oxide, styrene oxide, cyclohexylene oxide, and/or decylene oxide, and to the quarternized derivative of said alkoxylate in cleaning agents, as an emulsifier, in the production of fibers, for treating leather, in printing inks, in formulations for construction chemistry or in formulations for flotation. The invention further relates to a mixture containing at least one of said alkoxylates and to at least one surface-active substance and to the use thereof.


French Abstract

La présente invention concerne l'utilisation d'un alcoxylate à base de 2-propyl-heptyl-amine, qui a été alcoxylé avec de l'oxyde d'éthylène, de l'oxyde de propylène, de l'oxyde de butylène, de l'oxyde de pentylène, de l'oxyde de styrène, de l'oxyde de cyclohexylène et/ou de l'oxyde de décylène, ou de son dérivé rendu quaternaire, dans des agents de nettoyage, en tant qu'émulsifiant, lors de la production de fibres, pour le traitement du cuir, dans des encres d'impression, dans des formulations destinées à la chimie du bâtiment ou dans des formulations destinées à la flottation. L'invention a également pour objet un mélange contenant au moins l'un des alcoxylates mentionnés et au moins une substance tensio-active, et son utilisation.

Claims

Note: Claims are shown in the official language in which they were submitted.


14
We claim
1. The use of an alkoxylate of the general formula (A)
<IMG>
or of a quaternized alkoxylate of the general formula (AQ)
<IMG>
where
R1, R2 independently of one another, are selected from the group consisting of
ethylene, propylene, butylene, pentylene, phenylethylene, cyclohexylene,
decylene and mixtures thereof,
R3 is H, -OH, -OR4, -[R5-O]p-R6, C1-C6-alkyl or an oxygen anion,
R4 is C1-C6-alkyl, C2-C6-alkenyl or C2-C6-alkynyl,
R5 independently of one another, is selected from the group consisting of
ethylene, propylene, butylene and mixtures thereof,
R6 independently of one another, is -H, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-
alkynyl, -
SO3R a, -P(O)OR b OR c, -CH2CO2R d or -C(O)R e,
R a, R d independently of one another, are H, organic or inorganic cation,
R b, R c independently of one another, are H, organic or inorganic cation, C1-
C6-alkyl,
C2-C6-alkenyl or C2-C6-alkynyl,
R e is C1-C22-alkyl, C2-C22-alkenyl, C2-C22-alkynyl, C5-C22-aryl, C6-C22-
alkylaryl,
m, n, p independently of one another, are integers from 1 to 30 and
A- is an anion, where, in the case that R3 is an oxygen atom, A is not
present,
in cleaning compositions, as rust remover, as emulsifier, in the manufacture
of fibers, for
leather treatment, in printing inks, in formulations for construction
chemistry or in
formulations for flotation.

15
2. The use according to claim 1, wherein R1, R2 and R5, independently of one
another, are
ethylene, ethylene and propylene, ethylene and butylene or ethylene, propylene
and
butylene.
3. The use according to claim 1 or 2, wherein, in the alkoxylate of the
general formula (AQ),
A- is selected from the group consisting of halide, phosphate, sulfate,
carboxylate or a
mixture thereof.
4. The use according to any one of claims 1 to 3, wherein R3 is H.
5. The use according to any one of claims 1 to 4, wherein, in the alkoxylate
of the general
formula (A), the sum of n and m is 2 to 40.
6. The use according to any one of claims 1 to 4, wherein, in the alkoxylate
of the general
formula (AQ), the sum of n, m and p is 3 to 80.
7. A mixture comprising at least the components:
(A) at least one alkoxylate of the general formula (A) and/or (AQ) as defined
in any one
of claims 1 to 6 as component (A),
and
(B) at least one surface-active substance as component (B)
and/or
(C) at least one organic carboxylic acid as component (C).
8. The mixture according to claim 7, wherein at least one anionic surfactant,
at least one
cationic surfactant, at least one nonionic surfactant and/or at least one
amphoteric
surfactant is present as component (B).
9. The mixture according to claim 7 or 8, wherein the at least one organic
carboxylic acid is
selected from the group consisting of fatty acids having 12 to 18 carbon
atoms,
monocarboxylic acids having 1 to 10 carbon atoms, dicarboxylic acids having 2
to 16
carbon atoms and mixtures thereof.

16
10. The mixture according to any one of claims 7 to 9, wherein further
components selected
from the group consisting of organic or inorganic bases, inorganic acids,
silicone oils,
waxes, imidazolium salts and mixtures thereof are present.
11. The mixture according to any one of claims 7 to 10, which is an aqueous
mixture.
12. The use of the mixture according to any one of claims 7 to 11 in cleaning
compositions,
as emulsifier, in the manufacture of fibers, for leather treatment, in
printing inks, in
formulations for construction chemistry or in formulations for flotation.

Description

Note: Descriptions are shown in the official language in which they were submitted.


PF 70102 CA 02801643 2012-12-05
Alkoxylates and the use thereof
Description
The present invention relates to the use of an alkoxylate based on 2-
propylheptylamine which
has been alkoxylated with ethylene oxide, propylene oxide, butylene oxide,
pentylene oxide,
styrene oxide, cyclohexylene oxide and/or decylene oxide, and/or its
quaternized derivative in
cleaning compositions, as emulsifier, in the manufacture of fibers, for
leather treatment, in
printing inks, in formulations for construction chemistry or in formulations
for flotation.
Furthermore, the present invention relates to a mixture comprising at least
one of the specified
alkoxylates and also at least one surface-active substance and use thereof.
Compositions based on alkoxylated alkylamines are already known from the prior
art.
WO 2009/004044 Al discloses asymmetrically alkoxylated alkylamines which can
be used as
surfactants. The asymmetrically alkoxylated alkylamines are based on
corresponding
alkylamines having one to four carbon atoms, or benzylamines. 1 to 30 units of
ethylene oxide,
propylene oxide and/or butylene oxide are added by alkoxylation. WO
2009/004044 Al
furthermore discloses that these compounds can be used in herbicidally
effective compositions.
US 5,668,085 discloses surface-active compounds comprising alkoxylated amines.
These
alkoxylates are based on alkylamines or alkenylamines having 8 to 22 carbon
atoms and are
obtained by alkoxylation of these amines with ethylene oxide or propylene
oxide. In total, 2 to 8
units of the specified alkylene oxides are present in the compounds according
to US 5,668,085.
It was therefore an object of the present invention to provide an alkoxylate
which can be used in
various technical applications and produces advantageous results. Furthermore,
it is an object
of the present invention that corresponding alkoxylates are used which have
lower toxicity,
especially lower aquatoxicity.
These objects are achieved according to the invention through the use of an
alkoxylate of the
general formula (A)
C3H7 ~R? O-{-R6 (A)
C5H11 ThR-O-1 R6
m
or of a quaternized alkoxylate of the general formula (AQ)
C3H' 1 +R1 O~Rs
r A- (AQ)
C 5 H I T R2 -O R s
i ~

PF 70102 CA 02801643 2012-12-05
2
where
R1, R2 independently of one another, are selected from the group consisting of
ethylene, propylene, butylene, pentylene, phenylethylene, decylene and
mixtures thereof,
R3 is H, -OH, -OR4, -[R5-O]-R6, C,-C6-alkyl or an oxygen anion,
R4 is C,-C6-alkyl, C2-C6-alkenyl or C2-C6-alkynyl,
R5 independently of one another, is selected from the group consisting of
ethylene, propylene, butylene and mixtures thereof,
R6 independently of one another, is -H, C,-C6-alkyl, C2-C6-alkenyl, C2-C6-
alkynyl, -
SO3Ra, -P(O)OR bORc, -CH2CO2Rd or -C(O)Re,
Re, Rd independently of one another, are H, organic or inorganic cation,
Rb, Rc independently of one another, are H, organic or inorganic cation, C,-C6-
alkyl,
C2-C6-alkenyl or C2-C6-alkynyl,
Re is C,-C22-alkyl, C2-C22-alkenyl, C2-C22-alkynyl, C5-C22-aryl, C6-C22-
alkylaryl,
m, n, p independently of one another, are integers from 1 to 30 and
A" is an anion, where, the case that R3 is an oxygen atom, A is not present,
in cleaning compositions, as rust remover, as emulsifier, in the manufacture
of fibers, for
leather treatment, in printing inks, in formulations for construction
chemistry or in
formulations for flotation.
The objects are furthermore achieved according to the invention by a mixture
comprising at
least the components:
(A) at least one alkoxylate according to the invention of the general formula
(A) and/or (AQ)
as component (A),
and
(B) at least one surface-active substance as component (B)
and/or
(C) at least one organic carboxylic acid as component (C).
The compounds of the general formulae (A) and (AQ) used according to the
invention are
described in detail below.
Preferably, n has a value from 1 to 20, particularly preferably from 1 to 15.
Preferably, m has a
value from 1 to 20, particularly preferably from 1 to 15. Preferably, p has a
value from 1 to 30,
particularly preferably from 1 to 20. The values of n, m and p are normally
average values, as
arise in most cases during the alkoxylation with alkoxides. Consequently, n, m
and p can have
various whole-numbered values and also all values between the whole numbers.

PF 70102 CA 02801643 2012-12-05
3
Preferably, in the amine alkoxylate (A), the sum of n and m is 2 to 40. In a
further preferred
embodiment, in the quaternized amine alkoxylate of the general formula (AQ),
the sum of n, m
and p is 3 to 80.
In the amine alkoxylate (A), the sum of n and m is particularly preferably 3
to 30, very
particularly preferably 5 to 25. In a further, specifically preferred
embodiment, the sum of n and
m is 6 to 9, very particularly preferably 6.5 to 8.5 and in particular 6.9 to
7.9. In a further
specifically preferred embodiment, the sum of n and m is 11 to 40, in
particular 12 to 30 and in
particular 13.5 to 25.
In the alkoxylate of the general formula (AQ), the sum of n, m and p is
particularly preferably 3
to 40 and specifically 5 to 25.
R', R2 and R5 are generally, independently of one another, ethylene,
propylene, butylene,
pentylene, phenylethylene, decylene and mixtures thereof. These meanings for
R1, R2 and R5 in
the general formulae (A) and (AQ) therefore make reference to the fact that
2-propylheptylamine has been reacted with ethylene oxide, propylene oxide,
butylene oxide,
pentylene oxide, styrene oxide, decylene oxide or mixtures thereof.
R', R2 and R5 are preferably, independently of one another, ethylene, ethylene
and propylene,
ethylene and butylene or ethylene, propylene and butylene. In a particularly
preferred
embodiment, R1, R2 and R5 are propylene. In a further preferred embodiment,
R', R2 and R5 are
butylene. Particularly preferably, R1, R2 and R5 are, independently of one
another, ethylene or
ethylene and propylene. Very particularly preferably, R1, R2 and R5 are
ethylene.
If R1, R2 or R5 comprise a butylene radical, this may be present as n-
butylene, isobutylene
and/or 2,3-butylene group, where n-butylene and isobutylene are preferred and
n-butylene is
most preferred.
R1, R2 and R5 can, independently of one another, be a mixture of ethylene,
propylene or
butylene. Here, e.g. one or all radicals R1, R2 and R5 can in each case
comprise a mixture of
these groups in one alkoxylate chain. Such mixtures can be joined together in
any desired
order, for example randomly or blockwise, such as one block of ethylene and
one block of
propylene. It is also possible in each case for one or more radicals R', R2
and R5 to form a
complete alkoxylate chain from different alkylene groups. For example, R1 and
R2 can be
composed of ethylene and R5 of propylene.
R3 is preferably H, C,-C4-alkyl or an oxygen anion, particularly preferably H,
methyl, butyl or an
oxygen anion. In a specifically preferred embodiment, R3 is methyl. In a
further specifically
preferred embodiment, R3 is an oxygen anion. In a further specifically
preferred embodiment, R3
is H.

PF 70102 CA 02801643 2012-12-05
4
R4 is preferably a C,-C6-alkyl, in particular methyl or butyl such as n-butyl,
isobutyl and/or tert-
butyl, specifically methyl.
R6 is preferably H or C,-C6-alkyl, particularly preferably H or methyl, in
particular H.
Ra and Rd are, independently of one another, H+, or inorganic or organic
cations which may
have a single or multiple positive charge. Examples of inorganic cations are
cations of Na+, K+,
Mgt+, Cat+ or Zn2+. Examples of organic cations are ammonium, methylammonium,
dimethylammonium, trimethylammonium, tetramethylammonium, (2-
hydroxyethyl)ammonium,
bis(2-hydroxyethyl)ammonium, tris(2-hydroxyethyl)ammonium, tetra(2-
hydroxyethyl)ammonium.
Preferably, Re and Rd, independently of one another, are H+, or inorganic
cations, particularly
preferably as specified above. The radicals specified above under R6 which
comprise Re and Rd
are overall preferably uncharged.
Rb and R are preferably, independently of one another, H+, inorganic or
organic cations.
Suitable inorganic or organic cations are those specified under Ra and/or Rd.
RB is preferably C1-C12-alkyl, C5-C12-aryl or C6-C12-alkylaryl, particularly
preferably C,-C6-alkyl,
for example methyl, ethyl, propyl, such as n-propyl, isopropyl, butyl, such as
n-butyl, isobutyl,
tert-butyl, pentyl such as n-pentyl, isopentyl, tert-pentyl or hexyl such as n-
hexyl, isohexyl, tert-
hexyl.
K is an anion as are generally known per se to the person skilled in the art.
Preferably A" is a
halide such as chloride or bromide, phosphate, sulfate, carboxylate,
preferably derived from
carboxylic acids having 6 to 20 carbon atoms, or a mixture thereof. Overall,
the compound of
the general formula (AQ) is in this case uncharged.
If R3 is an oxygen anion, an amine oxide is present. In this case, a further
anion A" is not
present , and the compound of the general formula (AQ) is uncharged overall.
In the alkoxylate according to the general formula (A), R1 and R2 are
preferably, independently
of one another, ethylene, ethylene and propylene, ethylene and butylene or
ethylene, propylene
and butylene and the sum of n and m is 2 to 60, preferably 2 to 40,
particularly preferably 3 to
30 and in particular 5 to 25.
In a further preferred embodiment, in the alkoxylate according to the general
formula (A), R1 and
R2 are ethylene, ethylene and propylene, ethylene and butylene or ethylene,
propylene and
butylene and the sum of n and m is 6 to 9, in particular 6.5 to 8.5 and in
particular 6.9 to 7.9.
In a further preferred embodiment, in the alkoxylate according to the general
formula (A), R' and
R2 are ethylene, ethylene and propylene, ethylene and butylene or ethylene,
propylene and
butylene and the sum of n and m is 11 to 40, in particular 12 to 30 and in
particular 13.5 to 25.

PF 70102 CA 02801643 2012-12-05
In the amine alkoxylate of the general formula (A), R1 and R2 are particularly
preferably ethylene
and the sum of n and m is 2 to 60, preferably 2 to 40, particularly 3 to 30
and in particular 5 to
25. In a further particularly preferred embodiment, R1 and R2 are ethylene and
the sum of n and
m is 6 to 9, in particular 6.5 to 8.5 and in particular 6.9 to 7.9. In a
further preferred embodiment,
5 R1 and R2 are ethylene and the sum of n and m is 11 to 40, in particular 12
to 30 and in
particular 13.5 to 25.
The compounds of the general formulae (A) and (AQ) can be present as mixtures
of
stereoisomers or as isolated stereoisomers. Tautomers and betaines are
likewise comprised
according to the invention by the structures (A) and (AQ).
In the compounds of the general formulae (A) and (AQ), the radical C5Hõ can
either be linear or
branched. Examples of branched C5Hõ radicals are, for example, 1-methylbutyl,
2-methylbutyl,
3-methylbutyl, 1,2-dimethylpropyl, 2,3-dimethylpropyl, 1,1-dimethylpropyl or
2,2-dimethylpropyl.
Furthermore, in the compounds of the general formulae (A) and (AQ), the
radical C3H7 can be
either linear or branched. A branched C3H7 radical is, for example, 1-
methylethyl.
A process for the preparation of the compounds of the general formula (Q) or
(AQ) comprises,
for example, the alkoxylation of 2-propylheptylamine with ethylene oxide,
propylene oxide,
butylene oxide or a mixture thereof. The preparation of 2-propylheptylamine is
generally known,
for example by reacting ammonia with 2-propylheptanol as described in US
5,808,158. The
alkoxylation can be catalyzed by strong bases, such as alkali metal hydroxides
and alkaline
earth hydroxides, Bronsted acids or Lewis acids, such as AICI3, BF3. For
alcohol alkoxylates
with a narrow distribution it is possible to use catalysts such as
hydrotalcite or DMC. The
alkoxylation preferably takes place at temperatures in the range from about 80
to 250 C,
preferably about 100 to 220 C. The pressure is preferably between ambient
pressure and 600
bar. If desired, the alkylene oxide can comprise an inert gas admixture, e.g.
of about 5 to 60%.
The quaternized derivative (AQ) of the amine alkoxylate (A) can be prepared in
a further
reaction step from the amine alkoxylate (A) by quaternization. To insert the
radical R3 into the
amine alkoxylate (A), it can be reacted for example with an alkylating reagent
such as methyl
chloride, dimethyl sulfate or butyl chloride. To insert an oxygen anion into
the amine alkoxylate
(A), it can be oxidized, for example by reacting the amino group with hydrogen
peroxide,
peracids such as meta-chloroperbenzoic acid or peracetic acid or
peroxomonosulfuric acid. The
preparation of the quaternized derivatives (AQ) where R3 = H can take place by
simple
protonation of starting compounds of the structure (A). The preparation of the
quaternized
derivatives (AQ) where R3 = OH can take place by simple protonation of
starting compounds
(AQ) where R3 = oxygen anion. For the protonation, suitable acids are organic
acids, e.g. C, to
C20 carboxylic acids, for example the carboxylic acids or inorganic acids
specified as component
(C) of the mixture according to the invention, e.g. hydrochloric acid,
phosphoric acid or sulfuric
acid. The protonation can be carried out in a separate synthesis step so that
the quaternized

PF 70102 CA 02801643 2012-12-05
6
derivative (AQ) can be isolated. It is also possible to carry out the
protonation by mixing the
starting compounds with one or more acids in the mixture according to the
invention.
The present invention relates to the use of the aforementioned alkoxylates of
the general
formula (A) and/or of the general formula (AQ) in cleaning compositions, as
rust remover, as
emulsifier, during the manufacture of fibers, for leather treatment, in
printing inks, in
formulations for construction chemistry or in formulations for flotations.
Examples of cleaning compositions according to the invention are, for example,
cleaning
compositions for hard surfaces, for example glass, metal, plastic, painted
metal or plastic
surfaces such as surfaces of cars or lorries, as all-purpose cleaner or for
metal cleaning. In
these cleaning compositions, the compounds of the general formula (A) or (AQ)
are present in
an amount of, for example, 0.1 to 20% by weight, preferably 0.5 to 10% by
weight, particularly
preferably 0.5 to 5% by weight, in each case based on the total formulation.
Exemplary formulations in which the specified compounds of the general formula
(A) and/or
(AQ) can be used as rust removers, are, for example, formulations for removing
the rust from
metal surfaces, in particular iron surfaces. In these formulations for rust
removal, the
compounds of the general formula (A) or (AQ) are present in an amount of, for
example, 0.1 to
20% by weight, preferably 0.5 to 10% by weight, particularly preferably 0.5 to
5% by weight, in
each case based on the total formulation.
Exemplary formulations in which the specified compounds of the general formula
(A) and/or
(AQ) can be used as emulsifier are, for example, cooling lubricants, waxes,
bitumen emulsions,
silicone emulsions, in particular for textile applications, for example for
improving the feel
(softening/finishing). As emulsifier, the compounds of the general formula (A)
or (AQ) are
present in an amount of, for example 0.1 to 20% by weight, preferably 0.5 to
10% by weight,
particularly preferably 0.5 to 5% by weight, in each case based on the total
formulation.
During the manufacture of fibers, the aforementioned compounds are used for
example as
antistatics. In formulations which are used in the manufacture of fibers, the
compounds of the
general formula (A) or (AQ) are present in an amount of, for example, 0.1 to
20% by weight,
preferably 0.5 to 10% by weight, particularly preferably 0.5 to 5% by weight,
in each case based
on the total formulation.
During leather treatment, the aforementioned compounds are used for example
for degreasing.
In formulations for leather treatment, the compounds of the general formula
(A) or (AQ) are
present in an amount of, for example, 0.1 to 20% by weight, preferably 0.5 to
10% by weight,
particularly preferably 0.5 to 5% by weight, in each case based on the total
formulation.
In printing inks, the aforementioned compounds are used, for example, in water-
based ink-jet
printing inks. In printing inks, the compounds of the general formula (A) or
(AQ) are present in

PF 70102 CA 02801643 2012-12-05
7
an amount of, for example, 0.1 to 20% by weight, preferably 0.5 to 10% by
weight, particularly
preferably 0.5 to 5% by weight, in each case based on the total formulation.
In formulations for construction chemistry, the aforementioned compounds are
used, for
example, in bitumen emulsions. In these formulations used in construction
chemistry, the
compounds of the general formula (A) or (AQ) are present in an amount of, for
example 0.1 to
20% by weight, preferably 0.5 to 10% by weight, particularly preferably 0.5 to
5% by weight, in
each case based on the total formulation.
In formulations for flotations, the aforementioned compounds are used, for
example, for
removing printing inks (deinking). Methods and formulations for flotation are
known per se to the
person skilled in the art. In these formulations for flotation, the compounds
of the general
formula (A) or (AQ) are present in an amount of, for example, 0.1 to 20% by
weight, preferably
0.5 to 10% by weight, particularly preferably 0.5 to 5% by weight, in each
case based on the
total formulation.
The present invention also relates to a mixture comprising at least the
components:
(A) at least one alkoxylate of the general formula (A) and/or (AQ) as defined
above as
component (A),
and
(B) at least one surface-active substance as component (B)
and/or
(C) at least one organic carboxylic acid as component (C).
Component (A):
As regards component (A), in particular as regards the preferred embodiments,
that stated
above with regard to the alkoxylates of the general formula (A) and/or (AQ) is
applicable.
In the mixture according to the invention, the component (A) is generally
present in an amount
of from 0.1 to 20% by weight, preferably 0.5 to 15% by weight, particularly
preferably 0.8 to 12%
by weight, in each case based on the total mixture.
35, If the mixture according to the invention is used, for example, for the
cleaning of metal, the
component (A) is generally present in an amount of from 0.5 to 5% by weight,
preferably 0.8 to
2% by weight, in each case based on the total mixture.
If the mixture according to the invention is used, for example, in the
manufacture of fibers, the
component (A) is generally present in an amount of from 0.1 to 20% by weight,
preferably 0.5 to
5% by weight, in each case based on the total mixture.

PF 70102 CA 02801643 2012-12-05
8
Component (B):
As component (B), at least one surface-active substance is present in the
mixture according to
the invention.
In general, all surface-active substances known to the person skilled in the
art can be used as
component (B) in mixtures according to the invention.
In one preferred embodiment, at least one anionic surfactant, at least one
cationic surfactant, at
least one nonionic surfactant and/or at least one amphoteric surfactant is
present as component
(B).
Examples of anionic surfactants suitable according to the invention are
alcohol sulfate/ether
sulfates, alcohol phosphates and ether phosphates, alkylbenzenesulfonates,
alpha-
olefinsulfonates, sulfosuccinates etc.
Examples of cationic surfactants suitable according to the invention are
quaternized ammonium
salts such as N-alkyltrimethylammonium chloride or N,N-dialkyldimethylammonium
chloride,
amine oxides such as N-alkyldimethylamine oxide etc.
Examples of nonionic surfactants suitable according to the invention are
alcohol alkoxylates,
alkylamide ethoxylates, alkyl polyglucosides, PO-EO block copolymers, fatty
acid ethoxylates,
vegetable oil ethoxylates etc.
Examples of amphoteric surfactants suitable according to the invention are
alkylamine oxides,
betaines etc.
Processes for the preparation of the specified surface-active substances are
known to the
person skilled in the art. Furthermore, the specified surface-active
substances are commercially
available.
Surface-active substances which are particularly suitable according to the
invention are
selected from the group consisting of sodium salts of C10-C13-alkyl derivates
of benzenesulfonic
acid, oleylamine ethoxylate with 12 EO, lauryl/mistryl trimethylammonium
methosulfate and
mixtures thereof.
In the mixture according to the invention, the component (B) is generally
present in an amount
of from 0.1 to 50% by weight, preferably 1.0 to 40% by weight, particularly
preferably 1.0 to 30%
by weight, in each case based on the total mixture.

PF 70102 CA 02801643 2012-12-05
9
If the mixture according to the invention is used, for example, for the
cleaning of metal, the
component (B) is generally present in an amount of from 1.0 to 25% by weight,
preferably 1.5 to
20% by weight, in each case based on the total mixture.
Component (C):
As component (C), optionally at least one organic carboxylic acid is present
in the mixture
according to the invention.
In the mixture according to the invention, preferably the components (A) and
(B), (B) and (C) or
the components (A), (B) and (C) are present.
According to the invention, all carboxylic acids known to the person skilled
in the art can be
used as component (C). These are preferably selected from the group consisting
of fatty acids
having for example 12 to 18 carbon atoms, monocarboxylic acids and 1 to 10
carbon atoms,
dicarboxylic acids with 2 to 16 carbon atoms and mixtures thereof.
Fatty acids having 12 to 18 carbon atoms are known per se to the person
skilled in the art.
Examples are saturated or unsaturated fatty acids having 12 to 18 carbon
atoms.
Examples of saturated fatty acids having 12 to 18 carbon atoms are lauric acid
(C11H23COOH),
myristic acid (C13H27COOH), C14H20COOH, palmitic acid (C18H31COOH), margaric
acid
(C76H33COOH), stearic acid (C17H35COOH).
Examples of unsaturated fatty acids having 12 to 18 carbon atoms are
myristoleic acid
(C13H25000H), palmitoleic acid (C15H29COOH), petroselic acid (C17H33COOH),
oleic acid
(C17H33COOH), elaidic acid (C17H33COOH), vaccenic acid (C17H33000H). The
specified
unsaturated fatty acids with the same number of carbons differ by virtue of
the position of the
double bond.
Particularly preferably, fatty acids are present as component (C) in the
mixture according to the
invention if it is used for manufacturing fibers.
Monocarboxylic acids having 1 to 10 carbon atoms are likewise known to the
person skilled in
the art. Examples are formic acid, acetic acid, propionic acid, butyric acid,
pentanoic acid,
hexanoic acid, heptanoic acid, octanoic acid, in particular 2-
ethylhexylcarboxylic acid, nonanoic
acid or decanoic acid.
Particularly preferably, monocarboxylic acids are present in the mixture
according to the
invention if it is used for the cleaning of hard surfaces.

PF 70102 CA 02801643 2012-12-05
Dicarboxylic acids having 2 to 16 carbon atoms are likewise known to the
person skilled in the
art.
In the mixture according to the invention, the component (C) is present
generally in an amount
5 of from 0.1 to 20% by weight, preferably 2 to 15% by weight, particularly
preferably 3 to 12% by
weight, in each case based on the total mixture.
If the mixture according to the invention is used for example for the cleaning
of metal, the
component (C) is generally present in an amount of from 1 to 10% by weight,
preferably 3 to 7%
10 by weight, in each case based on the total mixture.
If the mixture according to the invention is used for example for the
manufacture of fibers, the
component (C) is generally present in an amount of from 0.1 to 20% by weight,
preferably 0.5 to
15% by weight, in each case based on the total mixture.
In a preferred embodiment of the present invention, the mixture according to
the invention is an
aqueous formulation. The present invention therefore preferably relates to the
mixture according
to the invention where it is an aqueous mixture. Consequently, in a preferred
embodiment, in
the mixture according to the invention, besides the specified components (A),
(B) and/or (C),
water, preferably demineralized and/or distilled water, is present. The
amounts of components
(A), (B) and/or (C), water and optionally present further components add up in
each case to
100% by weight.
According to the invention, in addition to the preferred solvent water,
organic, preferably polar,
solvents may also be present. Examples thereof are alcohols and mixtures
thereof. For the case
when organic solvents are also present besides water, these are present in an
amount of, for
example, 0.1 to 80% by weight, in each case based on the total mixture. In
this case, the
amounts of components (A), (B) and/or (C), water, organic solvent and
optionally present further
components in each case add up to 100% by weight.
Besides the components (A) and (B) or (A) and (C) or (A), (B) and (C), the
mixture according to
the invention can optionally comprise further components selected from the
group consisting of
inorganic or organic bases, inorganic acids, silicone oils, waxes, imidazolium
salts and mixtures
thereof.
Examples of inorganic bases which can be used according to the invention are
potassium
hydroxide and/or sodium hydroxide. These are present for example in an amount
of from 1 to
5% by weight, based on the total mixture.
Examples of organic bases which can be used according to the invention are
amines. These
are present for example in an amount of from 1 to 5% by weight, based on the
total mixture.

PF 70102 CA 02801643 2012-12-05
11
One example of an inorganic acid which can be used according to the invention
is boric acid.
This is present for example in an amount of from 1 to 5% by weight, based on
the total mixture.
Examples of silicon oils which can be used according to the invention are
those with a viscosity
of from 500 to 50 000 mm2/s at 25 C. These are present for example in an
amount of from 5 to
80% by weight, based on the total mixture.
Examples of waxes which can be used according to the invention are those with
a melting point
greater than 40 C. These are present for example in an amount of from 10 to
80% by weight,
based on the total mixture.
Optionally present alkylimidazolium salts are present for example in an amount
of from 0.4 to
12% by weight, based on the total mixture.
Very particularly preferred mixtures according to the invention are the
following:
Mixture for use as all-purpose cleaner:
1. 3.2% by weight of 2-propylamine, alkoxylated with 7 units of ethylene oxide
(component
(A)),
2. 2% by weight of C12/C14 alkyldimethylhydroxyammonium chloride (49% strength
by
weight solution in water) (component (B)) and
3. 94.8% by weight of water.
Mixture for use for the cleaning of hard surfaces:
1. 5% by weight of 2-propylamine, alkoxylated with 7 units of ethylene oxide
(component
(A)),
2. 5% by weight of ethyihexanoic acid (component (C)) and
3. 90% by weight of water.
Mixture for use for cleaning metal surfaces:
1. 2% by weight of boric acid,
2. 2% by weight of 50% strength KOH,
3. 15% by weight of Mazox LDA (lauramine oxide, 30% strength in water)
(component (B)),
4. 2% by weight of Lutensol ON 30 (component (B)),
5. 1 % by weight of 2-propylamine, alkoxylated with 7 units of ethylene oxide
(component (A))
and
6. 78% by weight of water.

PF 70102 CA 02801643 2012-12-05
12
Mixture for manufacturing fibers:
1. 5 to 80% by weight of silicone oil with a viscosity of from 500 to 50 000
mm2/s at 25 C,
2. 10 to 80% by weight of wax with a melting point greater than 40 C,
3. 1 to 10% by weight of fatty acids having 12 to 18 carbon atoms (component
(C)),
4. 0.4 to 12% by weight of alkylimidazolium salt,
5. 1 to 10% by weight of 2-propylamine, alkoxylated with 7 units of ethylene
oxide
(component (A)) and
6. remainder water.
The present invention also relates to a process for the preparation of the
specified mixtures
according to the invention by combining the individual components in the
respective amounts.
Devices for this process according to the invention are known to the person
skilled in the art.
The process according to the invention can be carried out at room temperature
or elevated
temperature.
The present invention also relates to the use of the mixture according to the
invention in
cleaning compositions, as rust remover, as emulsifier, during the manufacture
of fibers, for
leather treatment, in printing inks, in formulations for construction
chemistry or in formulations
for flotation. As regards these uses, that stated in relation to the use of
the compounds of the
general formula (A) and (AQ) is applicable.
The present invention is described in more detail by the examples below.
Examples:
Example 1 (comparative example):
A car washing formulation known from the prior art is used which has the
following composition:
10% by weight of benzenesulfonic acid, C10-13-alkyl derivative, sodium salt in
water (50%)
20% by weight of oleylamine ethoxylate with 12 EO,
12.5% by weight of lauryl/mistryl trimethylammonium methosulfate in water (30%
strength) and
57.5% by weight of demineralized water.
Example 2 (according to the invention):
In the formulation according to example 1, oleylamine ethoxylate having 12 EO
is replaced by
an equivalent amount of 2-propylheptylamine-(EO),o.

PF 70102 CA 02801643 2012-12-05
13
Results:
During the preparation of the formulations, it can be observed that the 2-
propylheptylamine
ethoxylate according to the invention can be incorporated into the formulation
considerably
better. Oleylamine ethoxylate having 12 EO needs longer until it has dissolved
in the
formulation.
Furthermore, the cleaning performance of the formulations according to example
1 and
example 2 is determined in accordance with Sheen (multitrack wiping device).
The cleaning
performance is the same for both formulations; the formulation according to
example 2 foams
more, but after rinsing the test plates, both are assessed the same.
In summary, it can be stated that the formulation according to the invention
as in example 2
exhibits an at least equally good cleaning performance as the formulation
known from the prior
art as in example 1. Furthermore, the formulation according to the invention
exhibits better
formulatability without loss of cleaning performance.

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Administrative Status

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Event History

Description Date
Inactive: IPC expired 2022-01-01
Application Not Reinstated by Deadline 2018-06-21
Time Limit for Reversal Expired 2018-06-21
Deemed Abandoned - Failure to Respond to Maintenance Fee Notice 2017-06-21
Letter Sent 2016-06-28
All Requirements for Examination Determined Compliant 2016-06-20
Request for Examination Requirements Determined Compliant 2016-06-20
Request for Examination Received 2016-06-20
Inactive: Cover page published 2013-02-01
Letter Sent 2013-01-29
Inactive: Notice - National entry - No RFE 2013-01-24
Inactive: IPC assigned 2013-01-24
Application Received - PCT 2013-01-24
Inactive: IPC assigned 2013-01-24
Inactive: First IPC assigned 2013-01-24
Inactive: Single transfer 2013-01-02
National Entry Requirements Determined Compliant 2012-12-05
Application Published (Open to Public Inspection) 2012-01-05

Abandonment History

Abandonment Date Reason Reinstatement Date
2017-06-21

Maintenance Fee

The last payment was received on 2016-06-16

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  • the reinstatement fee;
  • the late payment fee; or
  • additional fee to reverse deemed expiry.

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Fee History

Fee Type Anniversary Year Due Date Paid Date
Basic national fee - standard 2012-12-05
Registration of a document 2013-01-02
MF (application, 2nd anniv.) - standard 02 2013-06-21 2013-05-24
MF (application, 3rd anniv.) - standard 03 2014-06-23 2014-05-23
MF (application, 4th anniv.) - standard 04 2015-06-22 2015-06-12
MF (application, 5th anniv.) - standard 05 2016-06-21 2016-06-16
Request for examination - standard 2016-06-20
Owners on Record

Note: Records showing the ownership history in alphabetical order.

Current Owners on Record
BASF SE
Past Owners on Record
ANDREAS SENF
JUERGEN TROPSCH
PAUL KLINGELHOEFER
ROLF-DIETER KAHL
Past Owners that do not appear in the "Owners on Record" listing will appear in other documentation within the application.
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Document
Description 
Date
(yyyy-mm-dd) 
Number of pages   Size of Image (KB) 
Description 2012-12-05 13 631
Claims 2012-12-05 3 75
Abstract 2012-12-05 1 72
Cover Page 2013-02-01 1 31
Notice of National Entry 2013-01-24 1 193
Courtesy - Certificate of registration (related document(s)) 2013-01-29 1 101
Reminder of maintenance fee due 2013-02-25 1 112
Reminder - Request for Examination 2016-02-23 1 116
Acknowledgement of Request for Examination 2016-06-28 1 176
Courtesy - Abandonment Letter (Maintenance Fee) 2017-08-02 1 172
PCT 2012-12-05 6 192
Request for examination 2016-06-20 2 60