Siliconimides containing Si-H groups

Details Siliconimides containing Si-H groups Siliconimides containing Si-H groups

2000-01-19

2002-02-05

Moore, Margaret G. (Department: 1712)

Synthetic resins or natural rubbers -- part of the class 520 ser

Synthetic resins

From silicon reactant having at least one...

C528S015000, C528S031000, C528S026000

Reexamination Certificate

active

06344533

ABSTRACT:

TECHNICAL FIELD
Silicone imides containing Si—H groups
DESCRIPTION OF THE RELATED ART
The invention relates to a process for the preparation of silicone imides containing Si—H groups, silicone imides containing Si—H groups and their uses.
Silicone imides containing Si—H groups are known, for example, from GB-A-2143246. However, these silicone imides have the disadvantage that they contain ethylene groups in the main chain and therefore are not as stable as compounds which have only Si—O units in the main chain. Furthermore, these compounds are prepared such that where they have Si—H groups in the main chain, the formation of branchings which render the total compound insoluble is probable.
Silicone imides which under certain circumstances contain Si—H groups are moreover known, for example, from EP-A-328027. However, these compounds are heated to 160-170° C. during the imidation during the preparation, water being liberated, so that the hydrolysis-sensitive Si—H groups are converted in an uncontrolled manner, at least partly, into Si—OH or Si—O groups.
SUMMARY OF THE INVENTION
U.S. Pat. No. 4,598,135 A describes a process for equilibrating organosiloxanes containing Si—H groups into norbonanedicarboxylic acid anhydride-organo-siloxanes.
There is therefore the object of providing silicone imides containing Si—H groups which contain neither alkylene groups in the main chain nor an uncontrollable number of Si—OH groups.
The invention relates to a process for the preparation of silicone imides containing Si—H groups by equilibrating organosilicon compounds containing Si—H groups into silicone imides.
DESCRIPTION OF THE PREFERRED EMBODIMENTS
Preferably, polymeric silicone imides which contain Si—H groups and are composed of optionally siloxane units of the general formula (I)
R
a
SiO
(4-a)/2
  (I),
at least one siloxane unit of the general formula (II)
H
b
R
c
SiO
(4-b-c)/2
  (II)
and at least one silicone imide unit of the general formula (III)
are prepared by a procedure in which organosilicon compounds which are built up from at least one siloxane unit of the general formula (II) and optionally siloxane units of the general formula (I) are equilibrated into silicone imides which are composed of at least one silicone imide unit of the general formula (III) and optionally siloxane units of the general formula (I),
wherein
R denotes a monovalent radical, namely hydrogen or an unsubstituted or substituted C
1
-C
20
-hydrocarbon radical,
T denotes a trivalent substituted or unsubstituted aliphatic C
1
-C
18
-hydrocarbon radical or a trivalent substituted or unsubstituted aromatic C
6
-C
18
-hydrocarbon radical,
R′ denotes a divalent optionally halogen-substituted aromatic C
6
-C
30
-hydrocarbon radical, C
2
-C
20
-alkylene or cycloalkylene radical or a divalent radical of the general formula (IV)
Q′ denotes a chemical bond or a divalent optionally halogen-substituted organic C
1
-C
20
-radical,
Q denotes a tetravalent aromatic radical which is chosen from the groups
wherein
D is chosen from the groups:
—S(O)—
2
—, —C
x
H
2x
—, —C(O)—O—R′—O—C(O) and —O—R′—O—,
x denotes an integer from 1 to 5,
a denotes the values 0, 1, 2 or 3,
b denotes the values 1, 2 or 3,
c denotes the values 0, 1 or 2,
d denotes the values 0, 1, 2 or 3,
e denotes the values 0, 1, 2 or 3 and
n denotes an integer from 0 to 300.
If d and/or e have the value 3, the particular silicone groups are in the terminal position.
The hydrocarbon radicals R can be alkyl, cycloalkyl, alkenyl, aryl, aralkyl or alkylaryl groups. R preferably denotes alkyl radicals having 1 to 10 carbon atoms, such as methyl, ethyl, propyl, isopropyl, butyl, isobutyl, n-pentyl, isopentyl, neopentyl and tert-pentyl; cycloalkyl radicals having 5 to 8 carbon atoms, such as cyclopentyl, cyclohexyl, methylcyclohexyl, ethylcyclohexyl, cycloheptyl and norbornyl radicals; alkenyl radicals having 2 to 15 carbon atoms, such as vinyl, allyl, n-5-hexenyl, 4-vinylcyclohexyl and 3-norbornenyl; aryl radicals having 6 to 30 carbon atoms, such as phenyl, biphenyl, anthryl, phenanthryl and naphthyl; aralkyl radicals, such as benzyl, 1- or 2-phenylethyl, 1-, 2- or 3-phenylpropyl, o-methylphenylethyl, 3,5-dimethylphenylethyl, p-bromophenylethyl, o-bromophenylethyl, 3,5-dibromophenylethyl, p-chlorophenylethyl and 3,5-dichlorophenylethyl; and alkylaryl radicals, such as o-, m- and p-tolyl and xylyl. Examples of substituted hydrocarbon radicals as the radical R are halogenated hydrocarbon radicals, such as the chloromethyl, 3-chloropropyl, 3-bromopropyl, 3,3,3-trifluoropropyl, trifluorotolyl and 5,5,5,4,4,3,3-heptafluoropentyl radical, and the chlorophenyl, dichlorophenyl and trichlorotolyl radical; mercaptoalkyl radicals, such as the 2-mercaptoethyl and 3-mercaptopropyl radical; cyanoalkyl radicals, such as the 2-cyanoethyl and 3-cyanopropyl radical; acyloxyalkyl radicals, such as the 3-acryloxypropyl and 3-methacryloxypropyl radicals; acetoxyalkyl radicals, such as the 3-acetoxypropyl radical; succinic acid anhydride-alkyl radicals, such as the 3-succinic acid anhydride-propyl radical; phthalimidoalkyl radicals; ether radicals, such as the methoxyethylene glycol oxypropyl radical and methoxypolyethylene glycol ether propyl radical and epoxy radicals, such as the glycidyloxypropyl radical, methyl, ethyl, propyl and phenyl being preferred.
The trivalent hydrocarbon radicals T are, for example,
wherein
z denotes the values 0, 1, 2 or 3,
w denotes the values 1 or 2,
y denotes the values 0 or integers from 1 to 16 and
R″ denotes —O—, —CH
2
—, —(CH
2
)
2
— or —CH═CH—.
The divalent hydrocarbon radical R′ preferably denotes the following groups
Q′ is preferably chosen from a chemical bond and the groups —O—, —C(O)—, —S(O)
2
—, —S—, —C
x
H
2x
—, —C(CH
3
)
2
—, —C(CF
3
)
2
—, —C
x
H
x-2
— or —O—C
6
H
4
—Q″—C
6
H
4
—O—.
Q″ is preferably chosen from a chemical bond and the groups —O—, —C(O)—, —S(O)
2
—, —S—, —C
x
H
2x
—, —C(CH
3
)
2
—, —C(CF
3
)
2
— or C
x
H
x-2
.
The following units can be employed, for example, for Q:
The polymeric silicone imides containing Si—H groups can contain predominantly silicone contents, comparable contents of silicone content and imide content or predominantly imide contents.
Preferably, the polymeric silicone imides containing Si—H groups contain 0.001-99.6 mol %, articularly preferably 0.1-25 mol %, in particular 5-20 mol % of the general formula (I), 0.14-99.8 mol %, particularly preferably 60-99.5 mol %, in particular 75-95 mol % of the formula (II) and 0.2-99.5 mol %, particularly preferably 0.5 to 40 mol %, in particular 1-15 mol % of the general formula (III).
The preparation of the starting silicone imides which are composed of units of the general formula (III) and optionally siloxane units of the general formula (I) is described, for example, in U.S. Pat. No. 4,404,350.
The organosilicon compounds containing Si—H groups which are built up from at least one siloxane unit of the general formula (II) and optionally siloxane units of the general formula (I) can be cyclic and/or open-chain polymers. Preferably, the organosilicon compounds containing Si—H groups have at least three Si—H groups per molecule. Examples of the organosilicon compounds containing Si—H groups which can be employed in the process according to the invention are cyclic organohydridosiloxanes, such as siloxanes of the general formula (HSiR
3
)
u
, in which u denotes the values 3 to 10, in particular 3 to 6, and R has the above meanings, preferably methyl, ethyl, propyl and phenyl radicals. Tetramethylcyclotetrasiloxane, pentamethylcyclopentasiloxane and hexamethylcyclohexasiloxane are particularly preferred.
Further examples of the organosilicon compounds containing Si—H groups which can be employed in the process according to the invention are linear organohydridosiloxanes, such as organohydridosiloxanes which are preferably blocked on both ends by triorganosilyl or diorganosilyl groups, diorganosiloxane/organohydridopolysiloxane copolymers, or mixtures of two or more of these compounds. L

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