Organic compounds -- part of the class 532-570 series – Organic compounds – Silicon containing
Reexamination Certificate
2002-04-04
2004-07-06
Vollano, Jean F. (Department: 1621)
Organic compounds -- part of the class 532-570 series
Organic compounds
Silicon containing
Reexamination Certificate
active
06759545
ABSTRACT:
This invention relates to novel organosilicon compounds and processes for preparing the same. More particularly, it relates to novel organosilicon compounds having an organooxysilyl group at one end of a molecule and a monovalent hydrocarbon group at the other end thereof and containing a polysulfide group as well as novel organosilicon compounds having organooxysilyl groups at both ends of a molecule and containing a divalent hydrocarbon group flanked with polysulfide groups at a center thereof.
BACKGROUND OF THE INVENTION
Compounds containing alkoxysilyl and polysulfide groups within the molecule are known in the art. These compounds are used as an interfacial binder between inorganic materials such as silica, aluminum hydroxide and talc and organic materials such as thermosetting resins, thermoplastic resins and rubber, an adhesion modifier for organic resins and rubber, a primer composition or the like.
While sulfide group-containing organosilicon compounds are applied to composite materials composed of resins or rubber and inorganic materials as mentioned above, compositions obtained by adding known sulfide group-containing organosilicon compounds to resins or rubber and mixing them with inorganic materials suffer from insufficient abrasion resistance.
SUMMARY OF THE INVENTION
An object of the invention is to provide novel organosilicon compounds having overcome these disadvantages and drawbacks, and processes for preparing the same.
In one aspect, the invention provides an organosilicon compound having the following general formula (1):
(R
1
O)
(3-p)
(R
2
)
p
Si—R
3
—S
m
—R
4
—A (1)
wherein R
1
and R
2
each are a monovalent hydrocarbon group having 1 to 4 carbon atoms, R
3
and R
4
each are a divalent hydrocarbon group having 1 to 10 carbon atoms, A is hydrogen or the moiety: —S
m
—R
3
—Si(OR
1
)
(3-p)
(R
2
)
p
, m is 2 to 10, and p is equal to 0, 1 or 2.
In one embodiment of the process according to the invention, the organosilicon compound of formula (1) is prepared by the step of reacting a haloalkyl group-containing organosilicon compound of the following general formula (2):
(R
1
O)
(3-p)
(R
2
)
p
Si—R
3
—X (2)
wherein R
1
and R
2
each are a monovalent hydrocarbon group having 1 to 4 carbon atoms, R
3
is a divalent hydrocarbon group having 1 to 10 carbon atoms, X is halogen, and p is equal to 0, 1 or 2, and a halogen-containing compound of the following general formula (3):
X—R
4
—Y (3)
wherein R
4
is a divalent hydrocarbon group having 1 to 10 carbon atoms, X is halogen, and Y is hydrogen or halogen, with an anhydrous sodium sulfide or polysulfide having the following general formula (4):
Na
2
S
q
(4)
wherein q is 1 to 4, and optionally, sulfur.
In another embodiment of the process according to the invention, the organosilicon compound of formula (1) is prepared by the step of reacting a mercaptoalkyl group-containing organosilicon compound of the following general formula (5):
(R
1
O)
(3-p)
(R
2
)
p
Si—R
3
—SH (5)
wherein R
1
and R
2
each are a monovalent hydrocarbon group having 1 to 4 carbon atoms, R
3
is a divalent hydrocarbon group having 1 to 10 carbon atoms, and p is equal to 0, 1 or 2, with a sulfenamide group-containing compound of the following general formula (6):
(R
5
)(R
6
)N—S—R
4
—B (6)
wherein R
4
is a divalent hydrocarbon group having 1 to 10 carbon atoms, R
5
and R
6
each are independently hydrogen or a monovalent hydrocarbon group having 1 to 6 carbon atoms, with the proviso that R
5
and R
6
are not hydrogen at the same time, or R
5
and R
6
, taken together, form a divalent hydrocarbon group having 4 to 10 carbon atoms which may contain a nitrogen, oxygen or sulfur atom, and B is hydrogen or the moiety: —S—N(R
5
)(R
6
).
In a further embodiment of the process according to the invention, the organosilicon compound of formula (1) is prepared by the step of reacting a sulfenamide group-containing organosilicon compound of the following general formula (7):
(R
1
O)
(3-p)
(R
2
)
p
Si—R
3
—S—N(R
5
)(R
6
) (7)
wherein R
1
and R
2
each are a monovalent hydrocarbon group having 1 to 4 carbon atoms, R
3
is a divalent hydrocarbon group having 1 to 10 carbon atoms, R
5
and R
6
each are independently hydrogen or a monovalent hydrocarbon group having 1 to 6 carbon atoms, with the proviso that R
5
and R
6
are not hydrogen at the same time, or R
5
and R
6
, taken together, form a divalent hydrocarbon group having 4 to 10 carbon atoms which may contain a nitrogen, oxygen or sulfur atom, and p is equal to 0, 1 or 2, with a mercapto group-containing compound of the following general formula (8):
HS—R
4
—Z (8)
wherein R
4
is a divalent hydrocarbon group having 1 to 10 carbon atoms, and Z is hydrogen or SH.
REFERENCES:
patent: 4709065 (1987-11-01), Yoshioka et al.
patent: 5583245 (1996-12-01), Parker et al.
patent: 5663226 (1997-09-01), Scholl et al.
patent: 5780531 (1998-07-01), Scholl
patent: 5827912 (1998-10-01), Scholl
patent: 6194594 (2001-02-01), Gorl et al.
patent: 6300397 (2001-10-01), Sandstrom et al.
patent: 6423859 (2002-07-01), Alig et al.
patent: 6534668 (2003-03-01), Backer et al.
patent: 2003/0027966 (2003-02-01), Yanagisawa
patent: 2003/0176719 (2003-09-01), Yanagisawa et al.
patent: 2003/0236424 (2003-12-01), Yanagisawa et al.
patent: 44 24 582 (1996-01-01), None
patent: 0 670 347 (1995-09-01), None
patent: 0 748 839 (1996-12-01), None
patent: 0 753 549 (1997-01-01), None
patent: 465 267 (1991-08-01), None
patent: WO 02/20534 (2002-03-01), None
CA:137:263179 abs of EP 1247812 Oct. 2002.*
CA:133:266973 abs of JP2000264891 Sep. 2000.*
CA:114:143510 abs of Tetrahedron Letters by Stjernloef et al 31(40) pp 5773-5774 1990.*
CA:120:177984 abs of Chemistry Letters by Ichinose et al (11) pp 1961-1964 1993.*
CA:123:97953 abs of JP07084371 Mar. 1995.*
CA:114:143510 abs of Tetrahedron Letters by Stjernloef et al 31(40) pp 5773-5774 1990.*
Stjernlöf et al., Tetrahedron Letters, vol. 31, No. 40 (1990) pp. 5773-5774.
Yamaya Masaaki
Yanagisawa Hideyoshi
Shin-Etsu Chemical Co. , Ltd.
Vollano Jean F.
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