Carbosiloxane dendrimer and dendrimer-containing organic...

Details Carbosiloxane dendrimer and dendrimer-containing organic... Carbosiloxane dendrimer and dendrimer-containing organic...

2000-07-25

2001-10-23

Dawson, Robert (Department: 1712)

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

Synthetic resins

Polymers from only ethylenic monomers or processes of...

C528S015000, C528S025000, C528S031000, C528S032000

Reexamination Certificate

active

06306992

ABSTRACT:

FIELD OF THE INVENTION
This invention relates to a novel carbosiloxane dendrimer and to organic polymers containing this novel dendrimer. More particularly, this invention relates to a carbosiloxane dendrimer that contains a radically polymerizable group in each molecule and to the dendrimer-containing organic polymers afforded by the polymerization of this novel carbosiloxane dendrimer.
BACKGROUND OF THE INVENTION
Organopolysiloxanes that contain a radically polymerizable group (e.g., acryloxy or methacryloxy) in each molecule are known. Known in this regard are, for example, straight-chain polydimethylsiloxanes in which only a single terminal is endblocked by methacryloxypropyl and the following polydimethylsiloxane having a single branch point in the molecule
are described in Japanese Laid Open (Kokai or Unexamined) Patent Application Numbers Hei 7-196975 (196,975/1995), Hei 1-319518 (319,518/1989), and Hei 1-254719 (254,719/1989)). The use of these straight-chain organopolysiloxanes and branched organopolysiloxanes as co-monomers in the synthesis of various organic resins provides copolymers that have a low surface tension and an excellent surface lubricity. These copolymers, however, have poor compatiblilty with non-silicone-type organic resins.
In response to this problem, the present inventors have already disclosed a carbosiloxane dendrimer in the form of a multibranched siloxane-silalkylene copolymer that contains in each molecule one radically polymerizable group and at least 2 branch points (Japanese Laid Open (Kokai or Unexamined) Patent Application Numbers Hei 11-1485 (1,485/1999) and Hei 11-1530 (1,530/1999)). This carbosiloxane dendrimer can, for example, be reacted with other radically polymerizable monomers to produce a variety of graft copolymers bearing pendant dendrimer structures. However, the radically polymerizablc group and the dendrimer structure in this dendrimer are either directly bonded to each other or are bonded to each other across a lower alkylene group such as the propylene group. As a consequence, when this dendrimer is polymerized by itself or at high concentrations with other organic monomers, the reactivity is lowered by steric hindrance and the reaction does not proceed to completion.
SUMMARY OF THE INVENTION
The object of the present invention is to provide a novel carbosiloxane dendrimer that contains a radically polymerizable group in the molecule and which exhibits excellent polymerization reactivity. Another object of this invention is to provide dendrimer-containing organic polymers as afforded by the polymerization of the novel carbosiloxane dendrimer described herein.
This invention provides a radically polymerizable group-functional carbosiloxane dendrimer having the general formula
in which R
1
is a C
1
to C
10
alkyl group or aryl group; R
2
is a divalent organic group excluding C
1
to C
10
alkylene; b is 1 to 3; X
1
is the silylalkyl group with the following formula at i=1
where R
1
is defined as above; R
3
is C
2
to C
10
alkylene; R
4
is C
1
to C
10
alkyl;
X
i+1
is selected from hydrogen, C
1
to C
10
alkyl and aryl, and the above-defined silylalkyl group; i is an integer with a value from 1 to 10 that specifies the generation of said silylalkyl group; and a
i
is from 0 to 3;
and Y is a radically polymerizable group selected from
C
2
to C
10
alkenyl,
groups with the following general formula in which R
5
is hydrogen or methyl
groups with the following general formula in which R
5
is hydrogen or methyl
and groups with the following general formula
where R
6
is hydrogen or methyl, R
7
is C
1
to C
10
alkyl, and c is 0 to 4.
This invention additionally relates to dendrimer-containing organic polymer prepared by the polymerization of
(A) 100 to 0.1 weight % of the above-described carbosiloxane dendrimer, and
(B) 0 to 99.9 weight % of a radically polymerizable organic monomer.
DETAILED DESCRIPTION OF THE INVENTION
The carbosiloxane dendrimer of this invention is defined by the following general formula.
R
1
in this general formula denotes a C
1
to C
10
alkyl group or aryl group. The alkyl groups encompassed by R
1
can be exemplified by methyl, ethyl, propyl, butyl, pentyl, isopropyl, isobutyl, cyclopentyl, and cyclohexyl. The aryl groups encompassed by R
1
can be exemplified by phenyl and naphthyl. Methyl is preferred among the preceding for R
1
. R
2
in the preceding general formula may be any group other than C
1
to C
10
alkylene, but is preferably a divalent organic group composed of a plural number of elements selected from carbon, silicon, hydrogen, oxygen, nitrogen, and sulfur. R
2
is even more preferably a divalent organic group that connects the Y and Si through at least 5 atoms. R
2
can be specifically exemplified by groups with the following structures.
The group Y in the preceding general formula is a radically polymerizable group selected from;
C
2
to C
10
alkenyl,
groups with the following general formula in which R
5
is hydrogen or methyl
groups with the following general formula in which R
5
is hydrogen or methyl
and or groups with the following general formula
where R
6
is hydrogen or methyl, R
7
is C
1
to C
10
alkyl, and c is 0 to 4.
This radically polymerizable group Y can be specifically exemplified by acryloxy, methacryloxy, acrylamide, methacrylamide, 4-vinylphenyl, 3-vinylphenyl, 4-(2-propenyl)phenyl, 3-(2-propenyl)phenyl, 4-methyl-3-vinylphenyl, 2-octyl-4-vinylphenyl, vinyl, and 2-propenyl. The Y—R
2
-moiety comprising Y bonded to the above-described R
2
can be exemplified by the following groups.
Preferred among the preceding are groups that contain an ether linkage, and groups that contain both an ether linkage and a siloxane bond, as shown below.
The subscript b in the preceding general formula has a value from 1 to 3 and is preferably 3. X
1
is the silylalkyl group with the following formula at i=1
R
1
in the preceding formula for X
i
is defined as above, while R
3
is C
2
to C
10
alkylene, for example, straight-chain alkylene such as ethylene, propylene, butylene, and hexylene, or branched alkylene such as methylmethylene, methylethylene, 1-methylpentylene, and 1,4-dimethylbutylene. Preferred for R
3
among the preceding are ethylene, methylmethylene, hexylene, 1-methylpentylene, and 1,4-dimethylbutylene. R
4
is C
1
to C
10
alkyl, for example, methyl, ethyl, propyl, butyl, pentyl, isopropyl, isobutyl, cyclopentyl, and cyclohexyl. Methyl is preferred for R
4
. X
i+1
in the preceding formula for X
i
is selected from hydrogen, a C
1
to C
10
alkyl, a C
1
to C
10
aryl, and the above-defined silylalkyl group. The subscript a
i
is from 0 to 3, and the average of the sum of a
i
in each molecule is preferably no more than 1.5
i
×3. i is an integer with a value from 1 to 10 that specifies the generation of said silylalkyl group, i.e., that indicates the number of repetitions of this silylalkyl group. Thus, the carbosiloxane dendrimer of the present invention has the following general formula when the number of generations is 1:
in the preceding formula, R
1
, R
2
, R
3
, R
4
, Y, and b are defined as above; R
8
is hydrogen or R
1
; and a
1
is from 0 to 3. The inventive carbosiloxane dendrimer has the following general formula when the number of generations is 2:
where R
1
, R
2
, R
3
, R
4
, R
8
, Y, and b are defined as above and a
1
and a
2
are 0 to 3. The inventive carbosiloxane dendrimer has the following general formula when the number of generations is 3:
where in the preceding formula, R
1
, R
2
, R
3
, R
4
, R
8
, Y, and b are defined as above and a
1
, a
2
, and a
3
are 0 to 3.
The inventive carbosiloxane dendrimer can be a single compound or a mixture of the subject compounds. The dispersity index for the molecular weight (polystyrene basis), that is, the weight-average molecular weight divided by the number-average molecular weight (Mw/Mn), is preferably no more than 2. The inventive carbosiloxane dendrimer can be specifically exemplified by polymers with the following average molecular formulas

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