Surface-active organosilicon compounds

Details Surface-active organosilicon compounds Surface-active organosilicon compounds

1999-11-23

2001-04-17

Shaver, Paul F. (Department: 1621)

Organic compounds -- part of the class 532-570 series

Organic compounds

Silicon containing

C556S422000, C556S425000, C556S427000, C556S419000, C556S437000, C556S439000, C556S440000, C549S214000, C536S123000, C536S123100, C518S721000, C518S721000, C518S721000, C518S721000, C518S721000, C518S721000, C518S721000

Reexamination Certificate

active

06218560

ABSTRACT:

TECHNICAL FIELD
The invention relates to organosilicon compounds modified with mono- or polyhydroxylated hydrocarbon radicals or carbohydrate derivatives, their preparation and use.
BACKGROUND ART
The term organopolysiloxanes in the following text is understood as meaning dimeric, oligomeric and polymeric siloxanes. For example, carbohydrate-modified organopolysiloxanes are described in DE-A-4306041. In that specification, sugar residues are bonded to Si—H-functional organopolysiloxanes via a Pt-catalyzed hydrosilylation reaction of carbohydrate monomers or oligomers containing unsaturated hydrocarbon radicals. A disadvantage of the process of the latter patent is the use of transition metal catalysts to enable bonding of the corresponding carbohydrate compounds to the siloxane derivative. These transition metal catalysts cannot be removed from the product formed.
U.S. Pat. No. 5,739, 192 describes polysiloxane copolymers which are prepared by Michael addition of acrylates onto amino radicals of organopolysiloxanes. The end groups of the polysiloxane copolymers are hydrocarbon or polyether groups. The polysiloxane copolymers can be used as surfactants.
In the case of a hydrocarbon modification with the aid of hydrocarbon-containing (meth)acrylates, hydrophobic compounds are obtained. If polyalkylene oxide-containing acrylates are used, only slightly hydrophilic compounds are obtained.
Polysiloxanes with sugar residues are also described by JP-A-6268820. They are obtained by reaction of polysiloxanes with lactones which are derived from aldonic and uronic acid, and have surface-active properties. A disadvantage is that only oxidized sugars (sugar lactones) can be employed.
Further processes for the preparation of organosilanes, organosiloxanes or organopolysiloxanes containing carbohydrate radicals via nucleophilic addition reactions are described in DE-A-4318536. A disadvantage is that no keto function which can be made available for secondary reactions is present in the precursor.
DISCLOSURE OF INVENTION
The object of the present invention is to provide highly hydrophilic or highly interface- or surface-active organosilicon compounds without the use of transition metal catalysts, and without the disadvantages described above.
BEST MODE FOR CARRYING OUT THE INVENTION
The invention relates to organosilicon compounds containing units of the general formula (I)
A
a
R
b
SiX
c
O
(4-a-b-c)/2
  (I)
in which
R can be identical or different and is a monovalent hydrocarbon radical which has 1 to 22 carbon atoms and is optionally substituted by halogen, amino, mercapto or ammonium groups,
X is identical or different and is a chlorine atom or a radical of the formula —OR
1
,
R
1
is a hydrogen atom or an alkyl radical having 1 to 8 carbon atoms, which can be substituted by ether-oxygen atoms, or a radical of the general formula (II)
—R
2
{[CH(CH
3
)CH
2
O)
e
[CH
2
CH
2
O]
f
[(CH
2
)
4
O]
g
R
3
}
y-1
  (II),
in which
R
2
is a divalent, trivalent or tetravalent hydrocarbon radical having 2 to 30 carbon atoms, which may be interrupted by one or more groups of the formulae
 and which can be interrupted by oxygen atoms,
y is 2, 3 or 4, according to the valency of the radical R
2
,
R
3
is a hydrogen atom or a hydrocarbon radical which has 1 to 20 carbon atoms and is optionally interrupted by a group —C(O)—,
e, f and g in each case independently of one another are the value 0 or an integer from 1 to 200, with the proviso that the sum of e+f+g≧1,
A is a radical of the general formula (III)
—R
4
{—C(H)C
n
(H
2
O)
n
}
y-1
  (III),
in which
R
4
has a meaning given for R
2
,
y is the value 2, 3 or 4, according to the valency of the radical R
4
,
n is an integer from 1 to 1,000,000,
a is the value 0, 1 or 2 and
b and c in each case are the value 0, 1, 2 or 3, and in the case of oligo- and polysaccharides, one molecule of H
2
O is to be subtracted from the empirical formula per carbohydrate monomer or polymer added to the formula, or A is a partly reduced, oxidized or partly dehydrated or organyl-modified derivative of the formula (III), with the proviso that the sum of a+b+c≦4 and the organosilicon compound contains at least one radical A per molecule.
The organosilicon compounds are organosilicon compounds modified with mono- or polyhydroxylated hydrocarbon radicals or carbohydrate derivatives. These can be both silanes, i.e. compounds of the general formula (I) where a+b+c=4, and siloxanes, i.e. compounds containing units of the general formula (I) where a+b+c≦3. The organosilicon compounds are preferably organopolysiloxanes, in particular those which comprise units of the general formula (I).
The organosilicon compounds preferably have an average molecular weight of 200 to 1,000,000 g/mol, particularly preferably 5000 to 150,000 g/mol, and preferably a viscosity of 10 to 1,000,000 mm
2
/S, particularly preferably 20 to 100,000 mm
2
/S, in each case at 25° C.
The organosilicon compounds can be liquid, or else waxy or solid.
Examples of radicals R are alkyl radicals such as the methyl, ethyl, n-propyl, isopropyl, 1-n-butyl, 2-n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, neopentyl or tert-pentyl radicals; hexyl radicals such as the n-hexyl radical; heptyl radicals such as the n-heptyl radical; octyl radicals such as the n-octyl radical and isooctyl radicals such as the 2,2,4-trimethylphenyl radical; nonyl radicals such as the n-nonyl radical; decyl radicals such as the n-decyl radical; octadecyl radicals such as the n-octadecyl radical; cycloalkyl radicals such as the cyclopentyl, cyclohexyl or cycloheptyl radicals and methylcyclohexyl radical; alkenyl radicals such as the vinyl, allyl, 3-butenyl, 5-hexenyl, 1-propenyl and 1-pentenyl radicals; alkynyl radicals such as the ethynyl, propargyl and 1-propynyl radicals; aryl radicals such as the phenyl, naphthyl, anthryl and phenanthryl radical; alkaryl radicals, such as o-, m-, and p-tosyl radicals, xylyl radicals and ethylphenyl radicals; and aralkyl radicals such as the benzyl radical, the phenylethyl radical and the phenylnonyl radical.
Examples of substituted hydrocarbon radicals R are haloalkyl radicals, such as the 3,3,3-trifluoro-n-propyl radical, the 2,2,2,2′,2′,2′-hexafluoroisopropyl radical, the heptafluoroisopropyl radical and haloaryl radicals, such as the o-, m-, and p-chlorophenyl radical.
The radical R is preferably a hydrocarbon radicals which has 1 to 18 carbon atoms, optionally substituted by halogen, amine, mercapto or ammonium groups, the methyl, n-octyl, n-dodecyl and n-octadecyl radicals being particularly preferred.
Examples of alkyl radicals R
1
are the examples of alkyl radicals having up to 8 carbon atoms given for the radical R, and the methoxyethyl and ethoxyethyl radicals. The radical R
1
is preferably a hydrogen atom or a methyl, ethyl, butyl or propyl group, in particular a methyl or ethyl group.
Examples of radicals R
2
are
The radical R
2
is preferably
The methacrylates are also preferred.
Examples of radicals R
3
are the examples of hydrocarbon radicals having 1-20 carbon atoms given for the radical R, and also —CO—CH
3
, —CO—CH
2
—CH
3
and —CO—CH
2
CH
2
CH
2
CH
3
. The radical R
3
is preferably a hydrogen atom or a methyl or butyl group.
Examples of radicals X of the general formula (II) are —CH
2
—CH
2
—CO—[OC
2
H
4
]
9
OCH
3
, —CH
2
—CH
2
—CO—[OC
2
H
4
]
6
OC
6
H
5
and —CH
2
—CH
2
—CO—[OC
2
H
4
]
16
OC
6
H
4
-p-C
9
H
19
. The radicals of the general formula (II) are preferably
—CH
2
—CH
2
—CO—[OC
2
H
4
]
9
OCH
3
.
The value for the sum of e+f+g is preferably 2 to 30, particularly preferably 4 to 20.
X is preferably the radical —OR
1
, where R
1
has the abovementioned meaning, —OCH
3
and —OC
2
H
5
being particularly preferred.
Preferred examples of the radical R
4
are the examples given for the radical R
2
. The methacrylates are also preferred.
The value of n is preferably 2, 4, 5, 6, 7, 8

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