Compositions: coating or plastic – Coating or plastic compositions – O-containing organic compound
Reexamination Certificate
2001-03-14
2003-09-16
Cooney, Jr., John M. (Department: 1711)
Compositions: coating or plastic
Coating or plastic compositions
O-containing organic compound
C106S287300, C106S287320, C106S638000, C252S008810, C264S165000
Reexamination Certificate
active
06620231
ABSTRACT:
BACKGROUND OF THE INVENTION
1. Field of the Invention
The present invention relates to an antistatic composition and a formed article comprising the same. More particularly, the present invention relates to an antistatic composition which exhibits excellent antistatic properties even at low temperatures, and a formed article comprising the antistatic composition, which can be suitably used as shoe soles for, for instance, safety shoes, working shoes, and the like.
2. Discussion of the Related Art
Conventionally, as methods of giving antistatic properties, there have been known a method of adding carbon black or a conductive filler; a method of applying or adding an ionic surfactant; a method of adding an alkali metal salt of perchloric acid, thiocyanic acid or nitric acid; and the like as disclosed in Japanese Patent Laid-Open No. Sho 63-43951. Also, there has been known a method of employing an alkali metal salt in which the anion of a non-volatile ionic alkali metal salt is trifluoromethanesulfonic acid ion, thiocyanic acid ion, or a tetraorganoboronium ion (Japanese Patent Laid-Open No. Sho 63-154763).
On the other hand, Japanese Patent Laid-Open Nos. Hei 4-298517 and Hei 4-298518 disclose an additive which gives a polyurethane excellent antistatic properties without any problems in molding, and a process for preparing the polyurethane. The additive comprises a quaternary ammonium alkylsulfate or quaternary ammonium perchlorate, and at least one metal salt selected from the group consisting of alkali metal salts and alkaline earth metal salts of perchloric acid, thiocyanic acid and nitric acid.
However, when a usual ionic surfactant is used alone, sufficient antistatic properties cannot be imparted to the polyurethane. Also, when the conductive filler is used in the raw materials of the polyurethane, the viscosity of the raw materials increases, so that there arises a problem in moldability. Also, the metal salts of perchloric acid, thiocyanic acid and trifluoromethanesulfonic acid quickly exhibit antistatic properties. However, those compounds have some defects such that the conductivities of a final product become insufficient. Also, as to the metal salt of perchloric acid, there is a risk of explosion due to its oxidative function, and as to the metal salt of thiocyanic acid, there is a problem in corrosion for metals. Also, as to the metal salt of nitric acid, there is a problem that an urethane becomes yellow.
Also, the use of the quaternary ammonium alkylsulfate or the quaternary ammonium perchlorate cannot satisfy the demands of stable conductivities just after molding and with the passage of time.
An object of the present invention is to provide an antistatic composition which exhibits excellent antistatic properties at low temperatures or room temperature, and a formed article comprising the antistatic composition.
These and other objects of the present invention will be apparent from the following description.
SUMMARY OF THE INVENTION
According to the present invention, there are provided:
(1) in a method for improving antistatic properties, the improvement comprising the use of an antistatic composition comprising an ionic antistatic compound and a polar organic solvent;
(2) an antistatic composition comprising a nonmetallic antistatic compound, a metallic antistatic compound and a polar organic solvent;
(3) a formed article containing an antistatic composition comprising an ionic antistatic compound and a polar organic solvent;
(4) the formed article according to item (3), wherein the formed article is a shoe sole;
(5) a safety shoe having a shoe sole of item (4); and
(6) a process for producing a polyurethane foam comprising reacting a polyol solution comprising a polyol component, a blowing agent and a catalyst, with an isocyanate prepolymer in the presence of an antistatic composition comprising an ionic antistatic compound and a polar organic solvent.
DETAILED DESCRIPTION OF THE INVENTION
Representative examples of the ionic antistatic compound include a nonmetallic antistatic compound and a metallic antistatic compound. Those compounds can be used alone or in admixture of at least two kinds. It is preferable in the present invention to use the nonmetallic antistatic compound together with the metallic antistatic compound, from the viewpoint of exhibiting excellent antistatic properties.
Representative examples of the nonmetallic antistatic compound include quaternary ammonium sulfonates having a substituent such as a hydrocarbon group or an oxyhydrocarbon group (hereinafter referred to as “substituted quaternary ammonium sulfonate”), and the like. Among the substituted quaternary ammonium sulfonates, it is preferable to use a substituted quaternary ammonium sulfonate represented by the formula (I):
wherein R
1
is an alkyl group having 6 to 24 carbon atoms; each of R
2
and R
3
is independently an alkyl group having 1 to 4 carbon atoms, or R
2
is combined with R
3
to form an alkylene group having 4 to 5 carbon atoms or an oxyalkylene group having 3 to 4 carbon atoms, which forms a ring together with the adjacent nitrogen atom; R
4
is an alkyl group having 1 to 4 carbon atoms; and R
5
is a hydrocarbon group having 1 to 24 carbon atoms or an oxyhydrocarbon group having 1 to 24 carbon atoms.
In R
1
, among the alkyl groups having 6 to 24 carbon atoms, decyl group, lauryl group, myristyl group, palmityl group and stearyl group are preferable because the amine which is used as a raw material for the substituted quaternary ammonium shows favorable liquid properties during the preparation of the substituted quaternary ammonium sulfonate, and is less odorous. It is preferable that R
5
is an alkyl group such as methyl group, an alkoxy group such as methoxy group or ethoxy group, or an aryl group such as phenyl group or p-methylphenyl group. In addition, when R
2
forms a ring together with R
3
, each of R
2
and R
3
is preferably butylene group, pentylene group or ethylene oxyethylene group (—C
2
H
4
—O—C
2
H
4
—), from the viewpoint of giving a stable ring structure.
Among the substituted quaternary ammonium sulfonates, favorable ones are, for instance, dialkylsulfates such as
N,N,N-trimethyl-N-laurylammonium methylsulfate,
N,N,N-trimethyl-N-cetylammonium methylsulfate,
N-ethyl-N,N-diethyl-N-stearylammonium ethylsulfate,
N-ethyl-N,N-dimethyl-N-laurylammonium ethylsulfate and
N,N-diethylmorpholinium ethylsulfate; methanesulfonates such as
N,N,N-trimethyl-N-laurylammonium methanesulfonate,
N,N,N-trimethyl-N-cetylammonium methanesulfonate,
N-ethyl-N,N-dimethyl-N-stearylammonium methanesulfonate,
N-ethyl-N,N-dimethyl-N-laurylammonium methanesulfonate and
N,N-diethylmorpholinium methanesulfonate; p-toluenesulfonates such as
N,N,N-trimethyl-N-laurylammonium p-toluenesulfonate,
N,N,N-trimethyl-N-cetylammonium p-toluenesulfonate,
N-ethyl-N,N-dimethyl-N-stearylammonium p-toluenesulfonate,
N-ethyl-N,N-dimethyl-N-laurylammonium p-toluenesulfonate,
N,N-diethylmorpholinium p-toluenesulfonate, N-ethyl-N-methylmorpholinium p-toluenesulfonate; and the like.
The substituted quaternary ammonium sulfonate represented by the formula (I) can be readily prepared by adding a dialkylsulfuric acid dropwise to a tertiary amine corresponding to the substituted quaternary ammonium sulfonate in an amount equivalent to the tertiary amine in a desirable solvent, preferably a glycol, e.g. at least one glycol selected from the group consisting of ethylene glycol, 1,4-butanediol and diethylene glycol, and reacting the dialkylsulfuric acid with the tertiary amine.
Representative examples of the metallic antistatic compound include a metal alkylsulfonate, a metal benzenesulfonate or a metal alkylbenzenesulfonate represented by the formula (II):
[R
6
—SO
3
−
]
n
.M
n+
(II)
wherein R
6
is an alkyl group having 1 to 7 carbon atoms, phenyl group or phenyl group having a substituent such as an alkyl group having 1 to 7 carbon atoms; M is a metal atom; and n is a valence of the metal atom; alkali metal salts or alkaline earth metal salts of acids such as hydrochlo
Fukumoto Kazuo
Okubo Makoto
Birch & Stewart Kolasch & Birch, LLP
Cooney Jr. John M.
Kao Corporation
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