Synthetic resins or natural rubbers -- part of the class 520 ser – Synthetic resins – From silicon reactant having at least one...
Reexamination Certificate
2000-03-08
2001-07-31
Dawson, Robert (Department: 1712)
Synthetic resins or natural rubbers -- part of the class 520 ser
Synthetic resins
From silicon reactant having at least one...
C528S025000, C568S061000, C568S020000, C556S429000
Reexamination Certificate
active
06268455
ABSTRACT:
BACKGROUND OF THE INVENTION
1. Field of the Invention
The present invention relates to mercaptomethylphenyl group-containing diorganopolysiloxane and a production process for the same. More specifically, the present invention relates to mercaptomethylphenyl group-containing diorganopolysiloxane containing a mercaptomethylphenyl group and having an alkyl group, and a production process for the same.
2. Description of the Related Art
Diorganopolysiloxanes have so far been blended with organic resins for the purposes of providing the organic resins with properties such as a water repellency, a low adhesion, a excellent lubricity ability and the like. However, when diorganopolysiloxanes to be used do not have organic functional groups, caused are elimination of the diorganopolysiloxanes from the organic resins blended with the diorganopolysiloxanes by washing and bleeding-out of the diorganopolysiloxanes from the organic resins attributable to a low compatibility of the diorganopolysiloxanes with various organic resins, and thus the characteristics described above endowed to the organic resins have been temporary and not permanent.
On the other hand, when diorganopolysiloxanes having organic functional groups are used, a reactivity of the organic functional groups can be utilized to allow the diorganopolysiloxanes to be chemically bonded to various organic resins, so that the organic resins to be bonded therewith can be provided with properties (a water repellency, a low adhesion, a excellent lubricity ability and the like) which are inherent to the diorganopolysiloxanes without reducing the intrinsic characteristics of the resins.
This method is not carried out merely by mixing, and therefore a problem of bleeding-out and a reduction in various properties caused by washing are not observed. Accordingly, it can be said that various properties provided by this method are persistent effects. Thus, diorganopolysiloxanes having organic functional groups are useful as a modifier for organic resins.
Known as the diorganopolysiloxane having an organic functional group are amino-modified diorganopolysiloxanes, epoxy-modified diorganopolysiloxanes, alcohol-modified diorganopolysiloxanes, methacryloxy-modified diorganopolysiloxanes and carboxyl-modified diorgahopolysiloxanes.
When these diorganopolysiloxanes are chemically bonded to organic resins, the kinds of the organic functional groups on a diorganopolysiloxane side depend on the kinds of the organic functional groups on an organic resin side. That is, the organic functional groups on the diorganopolysiloxane side had to be organic functional groups which react with the organic functional groups on the organic resin side.
Accordingly, in order to provide organic resins having various organic functional groups with properties such as a water repellency, a low adhesion and a excellent lubricity ability which are inherent to diorganopolysiloxanes, diorganopolysiloxanes having various organic functional groups corresponding thereto have been requested to be developed.
On the other hand, when a block copolymer prepared by using radical polymerization for forming the skeleton is synthesized, a polymerizing method for the same includes (1) polymerization carried out with a high-molecular-weight initiator, (2) living radical polymerization and (3) reaction between end-functional prepolymers. Among them, in order to synthesize a block copolymer by reaction between end-functional prepolymers, suitable end-functional prepolymers are required, so that useful prepolymers have been desired.
SUMMARY OF THE INVENTION
Among a number of organic functional groups, a mercaptomethylphenyl group forms sulfide by reacting with an alkylating agent under a basic condition or reacting with alcohol under an acid condition, and therefore the present inventors considered that if mercaptomethylphenyl group-containing diorganopolysiloxane (hereinafter referred to as mercapto-modified silicone) in which a mercaptomethylphenyl group was introduced into a single end, both ends or a side chain of diorganopolysiloxane would be used, diorganopolysiloxane could be introduced into an organic resin having a hydroxyl residue, for example, polyvinyl alcohol and copolymers of hydroxyethyl methacrylate by making use of the above reaction, whereby a graft copolymer could be prepared.
Further, a mercaptomethylphenyl group has a large chain transfer coefficient and is immediately turned into a radical in the presence of a radical polymerization initiator, so that it can undergo radical polymerization with various monomers. Accordingly, the present inventors considered that mercapto-modified silicone would be useful as an end-functional prepolymer.
For example, when methacrylic esters are polymerized with a radical polymerization initiator, the addition of diorganopolysiloxane having a mercaptomethylphenyl group at a single end turns immediately the mercaptomethylphenyl group into a radical, which becomes a radical polymerization initiator for methacrylic esters. The present inventors considered that this process would make it possible to synthesize an AB type block copolymer of diorganopolysiloxane with poly(methacrylic acid ester).
However, mercapto-modified silicone has not so far been known.
Intensive researches continued by the present inventors based on a point of view that mercapto-modified silicone would be useful as a raw material for a graft copolymer and a block copolymer have resulted in finding that if mercaptomethylphenyl group-containing diorganopolysiloxane containing a mercaptomethylphenyl group and having an alkyl group would be use, diorganopolysiloxane could be introduced into an organic resin having a hydroxyl residue to prepare a graft copolymer and that an AB type block copolymer of the above diorganopolysiloxane with poly(methacrylic ester) would be able to be synthesized, and thus the present invention has been completed based on this knowledge.
The present invention shall be explained below in detail.
The first invention relates to a mercaptomethylphenyl group-containing diorganopolysiloxane compound represented by the following Formula (1):
wherein R
1
represents methyl or phenyl; R
2
represents a linear or branched alkyl group having 1 to 6 carbon atoms, a phenyl group or A; l represents an integer of 0 to 500; m represents an integer of 0 to 1,000; n represents an integer of 0 to 500; p represents an integer of 0 to 2; and A is a group represented by Formula (2):
wherein X represents a linear or branched alkylene group having 2 to 20 carbon atoms; at least one of R
3
, R
4
, R
5
, R
6
and R
7
represents mercaptomethyl, and the remaining groups represent a hydrogen atom or a linear or branched alkyl group having 1 to 20 carbon atoms.
REFERENCES:
patent: 5416230 (1995-05-01), Jung et al.
patent: 5436358 (1995-07-01), Jung et al.
patent: 5844060 (1998-12-01), Furyya et al.
Kimae Youichi
Matsuo Takashi
Chisso Corporation
Dawson Robert
McDermott & Will & Emery
Peng Kuo-Liang
LandOfFree
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