Synthetic resins or natural rubbers -- part of the class 520 ser – Synthetic resins – At least one aryl ring which is part of a fused or bridged...
Reexamination Certificate
2001-06-21
2003-09-09
Dawson, Robert (Department: 1712)
Synthetic resins or natural rubbers -- part of the class 520 ser
Synthetic resins
At least one aryl ring which is part of a fused or bridged...
C556S444000, C556S445000, C556S413000, C556S424000, C556S460000, C525S477000, C528S034000, C528S038000, C528S037000, C528S012000, C510S122000
Reexamination Certificate
active
06617391
ABSTRACT:
The present invention relates to linear polyalkylorgano-siloxanes having polyoxyalkylene and amino-functional groups which additionally have terminal alkoxy groups, and to the preparation and use thereof.
It is known that aminosiloxanes having primary and secondary nitrogen groups and sometimes reactive silanol groups are incorporated as conditioning agents into hair shampoo formulations. These products are in most cases in the form of a mixture with the aid of surface-active substances in water. Purely in their original form, they are not soluble in water. They are solubilized in water by surface-active substances (emulsifiers, for example primary, multiple, secondary or tertiary surfactant systems) and converted into an aqueous emulsion. These surface-active substances usually consist of ethoxylated fatty alcohols, ethoxylated glycerides, fatty acid esters or similar products. Various products are available commercially, in particular from Dow Corning under the names DC 929, DC 949 and DCQ 2-8220. Products which as such are not soluble in water without the addition of surface-active substances are also available commercially from General Electric, e.g. under the name SME 253.
In order to improve the solubility in water, the aminosiloxanes can additionally be substituted by polyoxyalkylene groups. For example, U.S. Pat. No. 5,075,403 describes polydialkylorganosiloxanes which carry amino and polyoxyalkylene groups. Such products are prepared by cohydrosilylation of allylamines and allyl polyethers to hydridopolydimethylsiloxanes. However, it is observed here that the hydrosilylation reaction often does not achieve the desired conversions and so the desired degree of modification along the polydimethylsiloxane chain cannot be established.
It is also observed that aminosiloxanes which carry additional polyoxyalkylene groups for the most part remain in the aqueous phase upon use and do not attach to the hair in the desired manner.
In addition, in the case of aminosiloxanes, it is generally observed that an unpleasant odor adheres to the products as a result of the liberation of traces of volatile amines. These odors are undesired in the field of cosmetics. If attempts are made to remove the odor by distillation, it is generally observed that the unpleasant odor returns after a short period.
The object of the present invention was to prepare conditioning agents based on hydrophilic polydialkylorganosiloxanes which contain aminosiloxane groups, have a mild odor and exhibit lasting conditioning properties within the hair.
Surprisingly, it has been found that linear polyalkylorgano-siloxanes having polyoxyalkylene and amino-functional groups which additionally have terminal alkoxy groups exhibit a greatly improved hydrophilicity and have excellent conditioning properties.
It has also been found that the synthesis of linear polyalkylorganosiloxanes having polyoxyalkylene and amino-functional groups by alkaline equilibration leads to products having terminal alkoxy groups and problems with incomplete conversions are avoided.
The present invention thus provides linear polydialkylorganosiloxanes having polyoxyalkylene and amino-functional groups which additionally have terminal alkoxy groups, of the general formula (I)
where
a=5 to 500 and
b=1 to 100 and
the radicals
R
1
=identical or different aliphatic or aromatic hydrocarbon radicals having up to 8 carbon atoms,
R
2
=R
1
, R
2a
or R
2b
, with the proviso that on statistical average a radical R
2a
is present in at least every tenth siloxane chain, and at least one radical R
2b
is present in each siloxane chain,
where
the radical R
2a
is chosen from the radicals of an amino-functional group of the general formula (II)
—[(R
4
)
c
—NR
5
]
d
—R
6
where
R
4
=a divalent C
1
to C
12
hydrocarbon radical, an —OCH
2
CH
2
— group or an OCH
2
CH(CH
3
)— group,
R
5
=a monovalent C
1
to C
12
hydrocarbon radical or a hydrogen atom,
R
6
=a monovalent aliphatic or aromatic, optionally substituted C
1
to C
12
hydrocarbon radical or a hydrogen atom,
where
c=1 to 10
d=1 to 5,
the radical R
2b
is a polyoxyalkylene group of the general formula (III)
—(CH
2
)
e
(OC
2
H
4
)
f
(OC
3
H
6
)
g
OR
6
where
e=2 to 10
f2 to 20
g=0 to 20 and
R
3
=R
1
or a group of the general formula (IV)
—OR
1
with the proviso that on statistical average at least one radical of the general formula (IV) is present on the siloxane backbone.
The present invention further describes the synthesis of hydrophilic polysiloxanes to which amino and polyoxyalkylene chains are linked at the same time via Si—C bonds.
In a preferred embodiment of the present invention, the polyalkylorganosiloxanes are those in which
a=a number in the range from 5 to 100, in particular 10 to 50,
b=a number in the range from 3 to 50, in particular 3 to 30 and
c=a number in the range from 1 to 10, in particular 1 to 6.
For the purposes of the present invention, particular preference is given to polydialkylorganosiloxanes where in the general formula (I) the radical R
1
is a methyl radical.
As stated above, it is a necessary condition that on statistical average at least one of the groups R
2b
and R
3
═—OR
1
is present in each molecule of the polydialkylorganosiloxanes, and a radical R
2a
is present at least in every tenth siloxane chain. For the purposes of the present invention, it is particularly preferred if the molar ratio of the groups R
2a
to R
2b
to R
3
═—OR
1
is 0.5 to 2 to 1.
A further preferred embodiment of the present invention consists in the process for the preparation of the polyalkyldiorganosiloxanes defined above. For the purposes of the present invention, the latter are prepared, for example, by equilibrating a mixture of a suitable polyethersiloxane of the general formula
and/or a cyclic polyethersiloxane of the general formula
where R
1
, R
2b
and b are as defined above and a′ =0 to 500, a suitable dialkoxyaminosilane and/or its partial hydrolyzate, optionally octamethylcyclotetrasiloxane and/or decamethylcyclopentasiloxane using a basic catalyst.
The basic catalysts are, in particular, catalysts, such as alkali metal hydroxides, in particular sodium, potassium and cesium hydroxides, alkali metal alkoxides, quaternary ammonium hydroxides, such as tetramethylammonium hydroxide, benzyltrimethylammonium hydroxide, benzyltriethylammonium hydroxide, benzyltrimethylammonium butoxide, &bgr;-hydroxyethyltrimethylammonium 2-ethylhexoate, quaternary phosphonium hydroxides, such as tetra-n-butylphosphonium hydroxide and tri-n-butyl-3-[tris(trimethylsiloxy)silyl]-n-propylphosphonium hydroxide, alkali metal siloxanolates and ammonium organosiloxanolates, such as benzyltrimethylammonium siloxanolate and tetramethylammonium siloxanolate.
Use is preferably made of 10 ppm to 1% by weight, in particular 50 to 2 000 ppm, of basic catalyst, in each case based on the weight of the total mixture.
The dialkoxyaminosilanes preferably have the general formula
(R
1
)(R
1
O)
2
Si(R
2a
)
in which
R
1
, R
2a
are as defined above.
Examples of dialkoxyaminosilanes are N-aminoethyl-3-aminopropylmethyldimethoxysilane, N-aminoethyl-3-aminopropylmethyldiethoxysilane, 3-aminopropylmethyldimethoxysilane and/or 3-aminopropylmethyldiethoxysilane.
Partial hydrolyzates of the dialkoxyaminosilanes are prepared in a preceding reaction step by condensation of the aminosilanes with water, those partial hydrolyzates having up to 30 silicon atoms being preferred.
Also described is the use of the compounds according to the invention for the preparation of haircare formulations, such as conditioning formulations (“conditioners”), hair rinses, conditioning shampoos, and conditioning agents which remain in the hair following application (“leave-in” products). The present invention likewise relates to the use of the compounds according to the invention for the treatment of textile surfaces and of natural and/or synthetic fibers and/or “nonwoven” materials, in particu
Krakenberg Manfred
Leidreiter Holger
Oestreich Sascha
Stadtmuller Stefan
Walter Akfred
Dawson Robert
Goldschmidt AG
Peng Kuo-Liang
LandOfFree
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