Organic compounds -- part of the class 532-570 series – Organic compounds – Sulfur containing
Reexamination Certificate
2002-09-12
2004-05-25
Vollano, Jean F (Department: 1621)
Organic compounds -- part of the class 532-570 series
Organic compounds
Sulfur containing
C568S028000, C568S057000, C568S067000, C568S027000
Reexamination Certificate
active
06740782
ABSTRACT:
TECHNICAL FIELD
The present invention relates to a novel sulfur-containing compound and molecular compound comprising the sulfur-containing compound as a component compound.
BACKGROUND ART
Molecular compounds are compounds where two or more compounds are bonded via a comparatively weak interaction other than covalent bonds as typified by a hydrogen bond and by van der Waals force. Because molecular compounds have a quality that allows them to dissociate into original component compounds by a simple manipulation, recently, their application has been anticipated in such spheres as selective separation of useful substances, chemical stabilization, non-volatilization, sustained release formulation, pulverization and the like.
One example of specific molecular compounds includes a clathrate compound and, for example, Japanese Unexamined Patent Publication No. Hei-6-166646 discloses clathrate compounds of tetraxis phenols with various organic compounds.
However, no molecular compound has been found which has satisfactory performance in selective separation, chemical stabilization, non-volatilization, sustained release formulation, pulverization and the like, due to problems in that the compounds are readily disintegrated by changes in external factors such as heat and pH, and compounds are easily dissociated in solutions in the conventional art.
The subject of the present invention is to provide a novel molecular compound which exhibits excellent performance in technical spheres such as selective separation of useful substances, chemical stabilization, non-volatilization, sustained release formation, pulverization and the like.
DISCLOSURE OF THE INVENTION
As a result of intensive research to solve the above problems, it has been found that a novel sulfur-containing compound derivative having triphenyl or tetrakisphenylthio skeleton exhibits excellent performance in technical spheres such as selective separation of useful substances, chemical stabilization, non-volatilization, sustained release formulation, pulverization, and the like, thereby the present invention has been completed.
That is, the present invention relates to a sulfur-containing compound represented by formula (I):
wherein each R independently represents a hydrogen atom, a C1 to C6 alkyl group which may have substituents, an alkenyl group which may have substituents, an aryl group which may have substituents, a chlorine atom or a bromine atom; m represents an integer of 0, 1, or 2; Z represents formulae (II) through (V):
wherein R and m are the same as defined in the above; W represents a hydrogen atom, or a C1 to C6 alkyl group which may be substituted; and Y represents a direct bond, an alkylene group having 1 to 3 carbons, or a phenylene group.
The invention further relates to molecular compounds such as clathrate compounds comprising the sulfur-containing compound represented by the above formula (I) as a component compound, and to molecular compounds such as the above-mentioned clathrate compounds comprising as component compounds the sulfur-containing component as well as an anti-microbial agent, anti-fungal agent, insecticide, insect repellent agent, perfume, deodorant/anti-odor agent, anti-foulant, curing agent and curing accelerator for painting, resins and adhesives, natural essential oil, anti-oxidant agent, vulcanization accelerator or organic solvent which reacts with the sulfur-containing compound to form a molecular compound.
The molecular compound of the present invention is a compound where two or more component compounds which can each exist in a stable and independent manner are bonded through a comparatively weak interaction by other than covalent bonds as typified by a hydrogen bond and Van der Waals force, and includes hydrates, solvates, addition compounds, clathrate compounds and the like.
In the sulfur-containing compound represented by formula (I), the substituents represented by R can specifically include, for example, a hydrogen atom, straight-chain, branched or cyclic C1 to C6 alkyl groups such as methyl, n-propyl, isopropyl, n-butyl, isobutyl, t-butyl, n-hexyl, cyclohexyl groups and the like, alkenyl groups such as allyl, vinyl, 2-butenyl, 1-methylallyl groups and the like, aryl groups such as phenyl, 2-pyrizyl, 1,3-dimethyl-5-pyrazole groups and the like, a chlorine atom, a bromine atom, and the like.
The above C1 to C6 alkyl, C2 to C6 alkenyl, and aryl groups may be further substituted with a cyano group; a halogen atom such as a fluorine, chlorine and bromine atoms; and an aryl group such as a phenyl group.
In the formulae (II) through (V) which represent Z in the formulae (I), (VI) and (VII), the same substituents as the above can be exemplified as R, and W can specifically include, for example, a hydrogen atom, straight-chain, branched or cyclic C1 to C6 alkyl groups such as methyl, n-propyl, isopropyl, n-butyl, isobutyl, t-butyl, n-hexyl, cyclohexyl groups and the like, which may be further substituted with a fluorine atom, halogen atom and the like.
Y can include a direct bond, alkylene groups having 1 to 3 carbons such as methylene, ethylene, propylene and the like, or a phenylene group. Substituted positions in the phenylene group are not particularly limited, and either the 1,2 position, the 1,3 position or the 1,4 position may be substituted. Also, the phenylene group can have substituents thereon other than the necessary binding positions.
In the formulae (VI) and (VIII) of the present invention, R′ can exemplify the same substituents as the aforementioned R.
And among the sulfur-containing compounds represented by formula (I) of the present invention, the compounds represented by formula (VI), particularly by the general formula (VIII) are preferable in terms of performances such as selective separation of useful substances, chemical stabilization, non-volatilization, sustained release formulation and pulverization. The compound represented by formula (VII) not only has clathrate ability but also is useful as an intermediate of the compound represented by formula (VI).
The compound of the present invention can be yielded by the following process for the production.
(Reaction 1)
Among the compounds represented by formula (I), the compound represented by formula (VII) can be yielded by chlorosulfonating the corresponding phenylalkane or phenylalkene in an organic solvent such as dichloromethane at room temperature. In this case, Z represents the same substituents as those in the aforementioned formulae (II) through (V), but it is unexacting even if there is no substituent S(O)mR on the phenyl group in the formulae (II) through (V).
(Reaction 2)
Among the compounds represented by formula (I), the compound wherein R is represented by a hydrogen atom and m is represented by 0 can be yielded by reducing the compound represented by formula (VII) obtained by Reaction 1 with a reducing agent such as LiAlH
4
, NaBH4 and the like in the organic solvent such as THF.
(Reaction 3)
Among the compounds represented by formula (I), the compound wherein R is represented by a C1 to C6 alkyl group which may have substituents and m is represented by 0 can be yielded by alkylating the compound given in (Reaction 2) with halogenated alkyl and the like in a solvent such as water, alcohol, ether, THF and the like in the presence of a base such as alcoholate, metallic hydride, organic metal, metalhydroxide and the like. When the mercapto group forms disulfide, alkylation can be carried out after treating with a reducing agent such as NaBH
4
.
(Reaction 4)
Among the compounds represented by formula (I), the compound wherein R is a C1 to C6 alkyl group which may have substituents and m is 1 or 2 can be yielded by oxidizing the compound given in (Reaction 3) with an oxidizing agent such as hydrogen peroxide solution or m-chloroperbenzoic acid in the suitable solvent.
(Reaction 5)
Among the compounds wherein Z is represented by formula (V), for the compound wherein Y is a direct bond, the compound wherein Z is represented by formula (IV) may be first synthesized by (Reaction 2) followed by be
Sato Ryu
Suzuki Hiroshi
LaPointe Dennis G.
Mason Law, P.A.
Nippon Soda Co. Ltd.
Vollano Jean F
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