Aminosiloxane polyether polymers

Details Aminosiloxane polyether polymers Aminosiloxane polyether polymers

2000-03-06

2001-12-04

Dawson, Robert (Department: 1712)

Coating processes

With post-treatment of coating or coating material

Heating or drying

C528S029000, C528S038000, C556S444000, C556S445000, C442S059000, C442S087000, C427S387000

Reexamination Certificate

active

06326061

ABSTRACT:

The invention relates to a textile treatment process which uses a composition based on aminoalkyl- and (iso)oxyalkyl-containing organopolysiloxane and to novel aminosiloxane-polyether polymers.
A number of recent patents describe modifications to the polyoxyalkylene chain or to the organopolysiloxane for property optimization for a large number of applications. The functional groups and the polyoxyalkylene chains can be linked to the organopolysiloxane by way of Si—O—C or Si—C bonds.
DE 3928867 describes the use of polysiloxane-polyoxyalkylene block copolymers which comprise at least one amino-functional group attached to a silicon atom in the production of polyurethane foams. The polyoxyalkylene group and the amino-functional group can be attached via Si—O or Si—C. The polyoxyalkylene group and the amino-functional group can be located either at the ends or at the sides. The amino-functional group comprises at least two nitrogen atoms, of which that located at the end must be fully substituted by alkyl groups.
There is no description of polysiloxane-polyoxyalkylene block copolymers which comprise an amino-functional group attached to a silicon atom and have only one nitrogen atom, or of those which comprise two or more nitrogen atoms in the side chain and in which the terminal nitrogen atoms are substituted by at least one hydrogen atom. The use of the polymers described in DE 3928867 for fibre finishing is likewise not described.
U.S. Pat. No. 5,075,403 and EP-A-0404698 describe a poly-diorganosiloxane having amino and polyoxyalkylene side groups. The functional groups are attached via Si—C. Preparation is by hydrosilylation. The use of the polymers of the invention as wetting agent and dispersant or as additive in fabric softeners or antifoam powders is described.
Si—O—C-attached polyoxyalkylene groups are not described.
EP-A-0579999 describes a composition for defoaming an aqueous, especially alkaline, formulation based on organofunctionally modified organopolysiloxanes and finely divided silica. The organopolysiloxane used in the formulation is an amino siloxane whose amine groups are connected to the organopolysiloxane by way of Si—C or Si—O—C bond. In addition to the amine groups, the organopolysiloxane may also contain polyether radicals connected to the organopolysiloxane by way of Si—C or Si—O—C bond.
The combination of amino-functional and polyalkylene oxide-containing groups in the organopolysiloxane is also known. Alkylamine-polyalkylene oxidepolydimethylsiloxane terpolymers and polydimethylsiloxaneamino-polyalkylene oxide block copolymers have already been used for the finishing of textiles (cf. A. M. Czech et al., “Modified Silicone Softeners for Fluorocarbon Soil Release Treatments”). In that case the polyalkylene oxide groups are linked to the organopolysiloxane by way of Si—C bond.
A disadvantage of the prior art is that Si—C-bonded polyalkylene oxide groups are available only by way of the hydrosilylation reaction of allylpolyalkylene oxide groups on H-containing silanes and organopolysiloxanes. This process requires relatively expensive raw materials and special safety measures, since elimination of hydrogen must be expected in the case of hydrosilylation reactions. In addition, Si—C-bonded polyalkylene oxide groups cannot readily be eliminated on demand, as is desired in textile finishing in order to improve exhaustion capacity and permanence.
It is an object of the invention to overcome the disadvantages of the prior art.
A subject of the invention is a process for textile treatment in which a composition comprising at least one
(A) silane or organosiloxane having at least one monovalent SiC-bonded radical with primary, secondary and/or tertiary amino groups and at least one
(B) (iso)oxyalkyl radical which is attached via Si—O—C is used.
In the composition, preferably, the silane or organosiloxane (A) has a unit of the general formula (I)
R
a
1
⁢
Q
b
⁢
SiO
(
4
-
a
-
b
)
2
(
I
)
and all other siloxane units in an organopolysiloxane have the general formula (II)
R
c
1
⁢
SiO
(
4
-
c
)
2
(
II
)
and have (iso)oxyalkyl radical of the formula
(OC
n
H
n
(−R)
n
)
o
  (III)
where
R can be identical or different and denotes hydrogen or a methyl radical.
The (iso)oxyalkyl radicals of the general formula (OC
n
H
n
(—R)
n
)
o
can also be linked to the organopolysiloxane at one or both ends by way of Si—O—C bonds. The (iso)oxyalkyl radicals are preferably adducts of polyethylene oxide, polypropylene oxide and their copolymers. By altering the polyethylene oxide/polypropylene oxide ratio it is possible to influence the stability of the Si—O—C bond to hydrolysis.
R
1
denotes identical or different, monovalent, unsubstituted or fluorine-, chlorine- or bromine-substituted C
1
to C
18
hydrocarbon radicals, hydrogen atoms, C
1
- to C
12
-alkoxy or hydroxyl radicals or alkyl glycol radicals,
Q denotes a group of the general formula (III)
—R
2
—[NR
3
(CH
2
)
m
]
d
N(R
3
)
2
  (III)
where
R
2
denotes a divalent C
1
to C
18
hydrocarbon radical,
R
3
denotes a hydrogen atom or an unsubstituted or fluorine-, chlorine- or bromine- or C
1
- to C
5
-alkoxy-substituted C
1
to C
18
hydrocarbon radical,
a has the values 0, 1 or 2,
b has the values 1, 2 or 3,
c has the values 0, 1, 2 or 3,
d has the values 0, 1, 2, 3 or 4,
m has the values 2, 3, 4, 5 or 6,
n has the values 2, 3 or 4 and
o has the values from 1 to 100
and the sum of a and b is not more than 4.
Examples of C
1
to C
18
hydrocarbon radicals are alkyl radicals, such as the methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, neopentyl, tert-pentyl radical; 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-trimethylpentyl radical; nonyl radicals, such as the n-nonyl radical; decyl radicals, such as the n-decyl radical; dodecyl radicals, such as the n-dodecyl radical; cycloalkyl radicals, such as cyclopentyl, cyclohexyl, cycloheptyl radicals and methylcyclohexyl radicals; aryl radicals, such as the phenyl and the naphthyl radical; alkaryl radicals, such as o-, m-, p-tolyl radicals, xylyl radicals and ethylphenyl radicals; and aralkyl radicals, such as the benzyl radical, the alpha- or &bgr;-phenylethyl radical.
The above hydrocarbon radicals R
1
may comprise an aliphatic double bond. Examples are alkenyl radicals, such as the vinyl, allyl, 5-hexen-1-yl, E-4-hexen-1-yl, Z-4-hexen-1-yl, 2-(3-cyclohexenyl)ethyl and cyclododeca-4,8-dienyl radical. Preferred radicals R
1
with aliphatic double bond are the vinyl, allyl, and 5-hexen-1-yl radical.
Preferably, however, not more than 1% of the hydrocarbon radicals R
1
contain a double bond.
Examples of C
1
to C
18
hydrocarbon radicals substituted by fluorine, chlorine or bromine atoms are the 3,3,3-trifluoro-n-propyl radical, the 2,2,2,2′,2′,2′-hexa-fluoroisopropyl radical, the heptafluoroisopropyl radical, and the o-, m- and p-chlorophenyl radical.
Examples of the divalent C
1
to C
18
hydrocarbon radicals R
2
are saturated straight- or branched-chain or cyclic alkylene radicals such as the methylene and ethylene radical and also propylene, butylene, pentylene, hexylene, 2-methylpropylene, cyclohexylene and octadecylene radicals or unsaturated alkylene or arylene radicals such as the hexenylene radical and phenylene radicals, particular preference being given to the n-propylene radical and the 2-methylpropylene radical.
The alkoxy radicals are above-described alkyl radicals which are attached by way of an oxygen atom. The examples of alkyl radicals apply fully to the alkoxy radicals R
1
as well.
The alkyl glycol radicals R
1
preferably have the general formula (IV)
—R
2
—[O(CHR
3
)
d
]
n
OR
4
  (IV)
in which R
2
, R
3
and d have the above definitions, n has a value from 1 to 100 and R
4
denotes a hydrogen atom, a radical R
3
or a group of the general formula —(C═O)—R
5
where R
5
denotes the radical R
3
or O—R
3
.

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