Macroazo compounds

Details Macroazo compounds Macroazo compounds

1999-05-28

2001-01-09

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...

C526S219600, C534S588000, C534S595000, C534S558000, C528S029000, C528S033000, C556S450000

Reexamination Certificate

active

06172171

ABSTRACT:

BACKGROUND OF THE INVENTION
This invention relates to novel macroazo compounds containing both of polyorganosiloxane units and polyoxyalkylene units in its molecules.
A silicone compound has such characteristics as excellent water-repellent ability and low coefficient of friction, and thus it has been known that a polysiloxane is added to resins or sprayed over them to give water repellent ability to the resins.
However, in methods of adding or spraying a polysiloxane to resins which has no compatibility or no miscibility with the polysiloxane, there has been found such a defect that the polysiloxane is oozed on the resin surface.
As means for solving this defect, there have been studied such methods as one comprising polymerizing a polymerizable monomer in the presence of a polyorganosilsesquioxane macromonomer or a polydialkylsiloxane macromonomer to form a graft polymer and one comprising polymerizing a polymerizable monomer in the presence of an azo-containing polyorganosiloxane compound to form a block copolymer, whereby a polysiloxane is introduced into a polymer molecule.
However, almost all of thus prepared polysiloxane-containing resins are those containing no polyoxyalkylene unit, or those containing a polyoxyalkylene unit but no polymer unit derived from an ethylenical monomer, and therefore those resins containing polysiloxane have such defects that they show only a poor affinity to polyethylene terephthalate (PET) and acryl type resins and further their hydrophilicity is not sufficient.
Further, though treating methods of mixing or reacting polyethylene glycol which has no compatibility with a polysiloxane resin have been tried, those method are accompanied with such problems that affinity between the resins is low, either one of the resins is oozed on the surface of the other resin which causes reduction of weathering resistance and chemical resistance, or no satisfactory adhesion to a substrate resin is attained which also causes reduction of chemical resistance and abrasion resistance. Thus no practical application has been attained.
SUMMARY OF THE INVENTION
The present invention has been accomplished under the circumstances as mentioned above and it provides a novel macroazo compound which makes it possible, for instance, in a case of using the compound as a polymerization initiator, to produce easily and at high efficiency a block polymer containing both polyorganosiloxane units and polyoxyalkylene units in its molecule.
The present invention relates to a macroazo compound, which comprises a repeating unit composed of a moiety of the formula (a), a moiety of the formula (b) and a moiety of the formula (c)
wherein X, E, Z and T are independently a lower alkylene group, R
1
, R
2
, R
3
and R
4
are independently a lower alkyl group or a cyano group, R
5
, R
6
, R
7
and R
8
are independently a lower alkyl group or an aryl group, and m and n are independently a positive integer, those moieties being bound with one another through a carboxylic acid ester linkage or a carboxylic acid amido linkage.
More particularly, the present invention relates to (A) the macroazo compound, wherein the repeating unit contains a polymerized unit composed of the moiety shown by the formula (a) and the moiety shown by the formula (c), the moieties being bound with each other through a carboxylic acid ester linkage or a carboxylic acid amido linkage, and a polymerized unit composed of the moiety shown by the formula (a) and the moiety shown by the formula (b), the moieties being bound with each other through a carboxylic acid ester linkage or a carboxylic acid amido linkage, and (B) the macroazo compound, wherein the repeating unit contains a polymerized unit composed of the moiety shown by the formula (a) and the moiety shown by the formula (b), the moieties being bound with each other through a carboxylic acid amido linkage, and a polymerized unit composed of the moiety shown by the formula (b) and the moiety shown by the formula (c), the moieties being bound with each other through a carboxylic acid amido linkage.
Further, the present invention relates to a polymerization initiator comprising the said compound.
DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS
The macroazo compound of the present invention includes one shown by the general formula [1]
wherein Q
1
, Q
2
, Q
3
and Q
4
are independently a carboxylic acid ester linkage or a carboxylic acid amido linkage, p, q and r are independently a positive integer and R
1
, R
2
, R
3
, R
4
, R
5
, R
6
, R
7
, R
8
, X, E, Z, T, m and n are the same meaning as above, and one shown by the general formula [2]
wherein Q is a carboxylic acid amido linkage, p′, q′ and r′ are independently a positive integer, and R
1
, R
2
, R
3
, R
4
, R
5
, R
6
, R
7
, R
8
, X, E, Z, T, m and n are the same meaning as above.
The compound shown by the general formula [1] includes one shown by the general formula [11-1
wherein Q′ is a carboxylic acid amido linkage, Q″ is a carboxylic acid ester linkage, and the other symbols have the same meaning as above, one shown by the general formula [1]-2
wherein the symbols have the same meaning as above, one shown by the general formula [1]-3
wherein the symbols have the same meaning as above, and one shown by the general formula [1]-4
wherein the symbols have the same meaning as above.
In the above general formula of (a), (b), (c), 11], [2], [1]-1, [1]-2, [1]-3 and [1]-4, the lower alkyl group shown by R
1
, R
2
, R
3
, R
4
, R
5
, R
6
, R
7
and R
8
may be straight chained or branched and includes one having 1 to 6 carbon atoms, which is specifically exemplified by a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a tert-butyl group, a sec-butyl group, an n-pentyl group, an isopentyl group, a neopentyl group, a tert-pentyl group, a 1-methylpentyl group, an n-hexyl group, an isohexyl group, a 2-methylpentyl group, a 3-methylpentyl group, etc.
The aryl group shown by R
5
, R
6
, R
7
and R
8
includes one having 6 to 10 carbon atoms, which is specifically exemplified by a phenyl group, an o-tolyl group, a m-tolyl group, a p-tolyl group, a 2,3-xylyl group, a 2,4-xylyl group, a 2,5-xylyl group, a naphthyl group, etc.
The lower alkylene group shown by X, E, Z and T may be straight chained, branched or cyclic and includes one having 1 to 10 carbon atoms, preferably 1 to 6 carbon atoms, which is specifically exemplified by a methylene group, an ethylene group, a trimethylene group, a propylene group, a tetramethylene group, a 2-methylpropylene group, a pentamethylene group, a 2-ethylpropylene group, a hexamethylene group, a heptamethylene group, an octamethylene group, a 2-ethylhexamethylene group, a nonamethylene group, a decamethylene group, a cyclopropylene group, a 1,2-cyclopentylene group, a 1,4-cyclohexylene group, etc.
The carboxylic acid ester linkage shown by Q
1
, Q
2
, Q
3,
Q
4
and Q″ is —COO— or —OCO—.
The carboxylic acid amido linkage shown by Q, Q
1
, Q
2
, Q
3
, Q
4
and Q′ is —CONH— or —NHCO—.
In the general formula [1], a ratio of p to q is generally 0.1≦p/(p+q)≦0.9, preferably 0.25≦p/(p+q)≦0.75.
In the general formula [2], a ratio of p′ to q′ is generally 0.1≦p′/(p′+q′)≦0.9, preferably 0.25≦p′/(p′+q′)≦0.75.
The symbols r and r′ are generally 2 or more, preferably 2 to 100, and more preferably 2 to 50.
The symbols m and n are generally 5 to 2,000, preferably 5 to 300.
A number average molecular weight of the compound shown by the general formulas [1] and [2] is generally 5,000 to 300,000, preferably 8,000 to 150,000.
The production of the macroazo compound of the present invention that is shown by the general formula [1] is conducted by reacting for instance, an azodicarboxylic acid shown by the general formula [3]
wher

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