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
1999-01-25
2001-01-23
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...
C524S801000, C524S157000, C524S158000, C524S161000, C528S038000, C528S032000, C528S026000
Reexamination Certificate
active
06177511
ABSTRACT:
TECHNICAL FIELD
The present invention relates to emulsions and microemulsions of amino-functional organosiloxanes and di- and/or oligo(meth)acrylates, and their Michael addition products.
BACKGROUND ART
Numerous silicone oil (micro)emulsions containing amino groups bound via Si-C bonds are known from the literature. Crosslinked silicone structures in emulsion are usually prepared by introduction of T or Q moieties (trifunctional or tetrafunctional siloxane units).
The polymerization of cyclopolyorganosiloxanes in emulsion to form polydiorganosiloxane microemulsions is described in EP-B 228 575 (Dow Corning Corporation; published on Feb. 3, 1993). Functional groups can be incorporated by means of appropriate alkoxysilanes, with branching established via T silanes (trifunctional silanes).
Silicone latices are disclosed in EP-A 739 928 (Dow Corning Corporation; published on Oct. 30, 1996). Crosslinking in emulsion occurs by means of a condensation reaction, addition reaction, or free-radical polymerization reaction. Addition reactions occur, for example, by addition of Si-bonded hydrogen onto Si-bonded vinyl groups.
Self-crosslinking silicone emulsions are known from EP-A 739 947 (Dow Corning Corporation; published on Oct. 30, 1996). Crosslinking occurs via acetoxy, aminoxy, acetamido, carboxyl, cycloalkyl, or oxime groups.
EP-A 739 929 (Dow Corning Corporation; published on Oct. 30, 1996) describes silicone latices having good thermal stability. The properties are achieved by means of specific emulsifiers.
Room temperature crosslinkable silicone elastomers are disclosed in U.S. Pat. No. 4,698,406 (Dow Corning Corporation; issued on Oct. 6, 1987). The silicone elastomers are prepared by reaction of amino silicones with silicone acrylates which is similar to a Michael addition.
A process for preparing silicone microcapsules by means of a reaction of silicones containing acryl and amino groups which is similar to a Michael addition is described in EP-B 267 003 (Dow Corning Corporation; published on Jul. 29, 1992).
A reaction of amino-functional polyorganosiloxanes with monoacrylated polyoxyalkylenes which is similar to a Michael addition is disclosed in EP-A 475 363 (Dow Corning Toray Silicone, published on Mar. 18, 1992). When used as textile finishing materials, the polyorganosiloxanes are notable for a low degree of yellowing and a good feel. The preparation is carried out in solution and does not allow a reaction with diacrylates, which would inevitably lead to gelling.
DISCLOSURE OF INVENTION
It is an object of the invention to provide organopolysiloxane compositions which are obtained from amino-functional organopolysiloxanes. A further object is to provide organopolysiloxane emulsions which are obtained by crosslinking aminosilicone oil emulsions or aminosilicone oil microemulsions and, if desired, additionally functionalizing the dispersed phase without the emulsion breaking.
DESCRIPTION OF THE PREFERRED EMBODIMENTS
The invention provides organopolysiloxane compositions comprising
(A) organopolysiloxanes which contain at least one SiC-bonded organic radical containing basic nitrogen, where the basic nitrogen can be present partially as a salt of a water-soluble organic or inorganic acid or water-insoluble organic acid,
(B) anionic, cationic, nonionic or amphoteric surfactants which are insoluble or soluble in (A),
(C) substituted or unsubstituted diacrylates and/or oligoacrylates, if desired (C′) substituted or unsubstituted acrylates and
(D) water.
The invention also provides organopolysiloxane compositions which can be prepared by reacting emulsions comprising
(A) organopolysiloxanes which contain at least one SiC-bonded organic radical containing basic nitrogen, where the basic nitrogen can be present partially as a salt of a water-soluble organic or inorganic acid or water-insoluble organic acid,
(B) anionic, cationic, nonionic or amphoteric surfactants which are insoluble or soluble in (A) and
(D) water with
(C) substituted or unsubstituted diacrylates and/or oligoacrylates and, if desired (C′) substituted or unsubstituted acrylates in a reaction similar to a Michael addition.
The invention further provides a process for preparing organopolysiloxane compositions which comprises reacting emulsions comprising
(A) organopolysiloxanes which contain at least one SiC-bonded organic radical containing basic nitrogen, where the basic nitrogen can be present partially as a salt of a water-soluble organic or inorganic acid or water-insoluble organic acid,
(B) anionic, cationic, nonionic or amphoteric surfactants which are insoluble or soluble in (A) and
(D) water with
(C) substituted or unsubstituted diacrylates and/or oligoacrylates and, if desired (C′) substituted or unsubstituted acrylates in a reaction similar to a Michael addition.
The organopolysiloxanes which contain at least one SiC-bonded organic radical containing basic nitrogen preferably comprise units of the formula
R
a
Y
b
Si
(
OR
1
)
c
O
4
-
(
a
+
b
+
c
)
2
,
(
I
)
where
R can be identical or different and are each a hydrogen atom or a monovalent organic radical containing no basic nitrogen,
R
1
can be identical or different and are each a hydrogen atom, an alkyl radical or an alkoxyalkyl radical,
Y can be identical or different and are each a monovalent, SiC-bonded radical containing basic nitrogen,
a is 0, 1, 2 or 3
b is 0, 1 or 2 and
c is 0, 2 or 3, with the proviso that the sum of a, b and c in the units of the formula (I) is less than or equal to 3 and at least one radical Y is present per molecule.
The radicals R are preferably monovalent hydrocarbon radicals having from 1 to 18 carbon atom(s).
Examples of radicals R are alkyl radicals such as the methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, tert-butyl, n-pentyl, iso-pentyl, neo-pentyl, 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-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, octadecyl radicals such as the n-octadecyl radical; alkenyl radicals such as the vinyl and allyl radicals, cycloalkyl radicals such as cyclopentyl, cyclohexyl, cycloheptyl radicals and methylcyclohexyl radicals, aryl radicals such as the phenyl, naphthyl, anthryl and phenanthryl radicals; alkaryl radicals such as o-, m-, p-tolyl radicals, xylyl radicals and ethylphenyl radicals; aralkyl radicals such as the benzyl radical, the &agr;- and the &bgr;-phenylethyl radical, with preference being given to the methyl radical, ethyl radical, n-propyl radical, isopropyl radical and n-butyl radical and particular preference being given to the methyl radical.
The radicals R
1
are preferably alkyl radicals having from 1 to 4 carbon atom(s). Examples of alkyl radicals R
1
are the methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl and tert-butyl radicals, with preference being given to the methyl and ethyl radicals.
Examples of alkoxyalkyl radicals are the methoxyethyl radical and the ethoxyethyl radical.
The radicals Y preferably have the formula
R
2
2
NR
3
(—NR
2
—R
3
)
x
— (II)
where x is 0 or an integer from 1 to 10, R
2
can be identical or different and are each hydrogen, an alkyl radical, a cycloalkyl radical or a radical of the formula —C(═O)—R or —CH
2
—CH
2
—C(═O)—O—R (where R is as defined above) and R
3
is a divalent hydrocarbon radical having from 1 to 12 carbon atoms per radical.
Examples of alkyl or cycloalkyl radicals R
2
are the same as those given for alkyl and cycloalkyl radicals R.
Preferably, at least one hydrogen atom is bound to each nitrogen atom in the radicals of the formula (II).
Examples of radicals R
3
are the methylene, ethylene, propylene, butylene, cyclohexylene, octadecylene, phenylene and butylene radicals, with preference being given to the n-propylene radical, particularly because of the ready availability.
Examples of radi
Dauth Jochen
Deubzer Bernward
Gratzl Petra
Schrock Robert
Brooks & Kushman P.C.
Dawson Robert
Peng Kuo-Liang
Wacker-Chemie GmbH
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