Organosilicon compounds having urea groups, method for...

Details Organosilicon compounds having urea groups, method for... Organosilicon compounds having urea groups, method for...

1999-05-24

2001-04-17

Moore, Margaret G. (Department: 1712)

Synthetic resins or natural rubbers -- part of the class 520 ser

Synthetic resins

From silicon reactant having at least one...

C556S411000

Reexamination Certificate

active

06218498

ABSTRACT:

TECHNICAL FIELD
The invention relates to organosilicon compounds which contain urea groups linked via Si—N bonds, their preparation and their use.
DESCRIPTION OF THE RELATED ART
Silylation products of urea, such as, for example, N,N′-bis(trimethylsilyl)urea and derivatives thereof, are already known. In this context, reference may be made, for example, to U.S. Pat. No. 3,346,609 (General Electric Co.; published on Oct. 10, 1967). U.S. Pat. No. 3,239,489 (Monsanto Co.; published on Mar. 8, 1966) describes polymers which consist of the sequence -silane unit-urea unit-hydrocarbon chain- which can be prepared by reaction of silazanes with diisocyanates. U.S. Pat. No. 4,959,407 (General Electric Co.; published on Sep. 25, 1990) furthermore discloses siloxane chains which are blocked on the ends by urea units and have a maximum of 10 siloxane units as chain lengtheners.
SUMMARY OF THE INVENTION
The invention pertains to organosilicon compounds having at least three silicon atoms and which contain urea groups bonded via Si—N bonds. The urea group-containing organosilicon compounds are useful in preparing moisture curable RTV-1 compositions, and are useful in diverse processes where scavenging of protic materials, particularly water, is desired. The invention also pertains to processes for the preparation of the Si—N linked, urea group-containing organosilicon compounds.
DESCRIPTION OF THE PREFERRED EMBODIMENTS
The invention relates to organosilicon compounds having at least three silicon atoms, of units of the formula
R
a
Si(NR
1
C═ONR
2
2
)
k
(NR
3
C═ONR
4
)
t/2
Y
m
O
n/2
[(CR
5
2
)
s
]
r/2
  (I)
where Y is units of the formula
—SiR
6
3-p-q
(NR
1
C═ONR
2
2
)
p
(NR
3
C═ONR
4
)
q/2
  (II),
in which R, R
1
, R
2
, R
3
, R
4
, R
5
and R
6
independently of one another can in each case be identical or different and are a hydrogen atom or optionally substituted monovalent hydrocarbon radicals having 1 to 20 carbon atoms,
a is 0, 1, 2 or 3,
k is 0, 1, 2 or 3,
t is 0, 1, 2, 3 or 4,
n is 0, 1, 2, 3 or 4,
m is 0 or 1,
r is 0 or 1,
s is an integer from 1 to 20,
p is 0, 1, 2 or 3 and
q is 0, 1, 2 or 3, with the proviso that
the sum p+q is ≦3,
the sum a+k+t+m+n+r is 4,
the sum m +r is 0 or 1 and
the organosilicon compound according to the invention contains at least one unit of the formula (I) where t is other than 0.
Although expressed by the formulae (I) and (II), it is to be stated again that all the radicals characterized by the indices a, k, t, m, n, r, p and q are Si-bonded radicals, and the radicals —(NR
3
C═ONR
4
)—, —O— and —(CR
5
2
)
s
— in each case have 2 Si bonds.
Preferably, in the units of the formula (I), the sum k+t+n is other than 0.
Examples of hydrocarbon radicals R and R
6
are alkyl radicals, such as the methyl, ethyl, n-propyl, isopropyl, 1-n-butyl, 2-n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, neopentyl or tert-pentyl radical; hexyl radicals, such as the n-hexyl radical; heptyl radicals, such as the n-heptyl radical; octyl radicals, such as the n-octyl radical and iso-octyl radicals, such as the 2,2,4-trimethylpentyl radical; nonyl radicals, such as the n-nonyl radical; decyl radicals, such as the n-decyl radical; dodecyl radicals, such as the n-dodecyl radical; and octadecyl radicals, such as the n-octadecyl radical; alkenyl radicals, such as the vinyl and the allyl radicals; cycloalkyl radicals, such as cyclopentyl, cyclohexyl and cycloheptyl radicals and methylcyclohexyl radicals; aryl radicals, such as the phenyl, naphthyl, anthryl and phenanthryl radical; alkaryl radicals, such as o-, m- and p-tolyl radicals, xylyl radicals and ethylphenyl radicals; and aralkyl radicals, such as the benzyl radical and the &agr;- and the &bgr;-phenylethyl radical.
Examples of substituted hydrocarbon radicals R and R
6
are halogenated radicals, such as the 3-chloro-propyl radical, the 3,3,3-trifluoropropyl radical, chlorophenyl radicals and hexafluoropropyl radicals, such as the 1-trifluoromethyl-2,2,2-trifluoroethyl radical; the 2-(perfluorohexyl)ethyl radical, the 1,1,2,2-tetra-fluoroethyloxypropyl radical, the 1-trifluoromethyl-2,2,2-trifluoroethyloxypropyl radical, the perfluoroiso-propyloxyethyl radical and the perfluoroisopropyloxy-propyl radical; radicals substituted by amino groups, such as the N-(2-aminoethyl)-3-aminopropyl radical, the 3-aminopropyl radical and the 3-(cyclohexylamino)propyl radical, 3-(N,N-diethyl-2-aminoethylamino)propyl radical and 3-(butylamino)propyl radical and 3-(3-methoxypropylamino)propyl radical; ether-functional radicals, such as the 3-methoxypropyl radical and the 3-ethoxypropyl radical; cyano-functional radicals, such as the 2-cyano-ethyl radical; ester-functional radicals, such as the methacryloxypropyl radical; epoxy-functional radicals, such as the glycidoxypropyl radical; sulfur-functional radicals, such as the 3-mercaptopropyl radical; and radicals substituted by (poly)glycol groups, it being possible for the latter to be built up from oxyethylene and/or oxypropylene units.
Preferred radicals R and R
6
are, in each case independently of one another, hydrocarbon radicals having 1 to 10 carbon atoms, hydrocarbon radicals having 1 to 10 carbon atoms which are substituted by amino groups or by fluorine radicals, and optionally substituted amino and glycidoxy groups which are bonded to the silicon atom via alkylene radicals having 2 to 6 carbon atoms.
The radicals R and R
6
are particularly preferably, in each case independently of one another, alkyl radicals and alkenyl radicals having 1 to 4 carbon atoms, such as the methyl and the vinyl radical, and optionally substituted amino and glycidoxy groups which are bonded to the silicon atom via alkylene radicals having 2 to 6 carbon atoms, such as, for example, the 3-(2-aminoethylamino)propyl radical, the 3-(cyclohexylamino)propyl radical or the 3-(glycidoxy)propyl radical.
Both R and R
6
are, in particular, the methyl radical.
Examples of radicals R
1
, R
2
, R
3
and R
4
as optionally substituted hydrocarbon radicals are the examples given above for radical R and R
6
.
Preferred radicals R
1
, R
2
, R
3
and R
4
are, in each case independently of one another, hydrogen and hydrocarbon radicals having 1 to 10 carbon atoms.
The radicals R
1
, R
2
, R
3
and R
4
are particularly preferably, independently of one another, a hydrogen atom or the methyl radical.
Examples of the radical R
5
are the examples given above for radical R and R
6
.
The radical R
5
is preferably a hydrogen atom or hydrocarbon radicals having 1 to 10 carbon atoms, as well as amino-functional and fluorine-substituted hydrocarbon radicals; R
5
particularly preferably being a hydrogen atom.
a is preferably 1, 2 or 3.
k is preferably 0, 1 or 2.
t is preferably 1, 2 or 3.
n is preferably 1 or 2.
s is preferably 2.
p is preferably 0, 1 or 2.
q is preferably 1 or 2.
Examples of the units of the formula (I) are
1a) Me
3
Si(NH—C═O—NH)
1/2
; Me
2
Si(NH—C═O—NH)
2/2
; MeSi(NH—C═O—NH)
3/2
; Si(NH—C═O—NH)
4/2
;
1b) Me
3
Si(NMe—C═O—NMe)
1/2
; Me
2
Si(NMe—C═O—NMe)
2/2
; MeSi(NMe—C═O—NMe)
3/2
; Si (NMe—C═O—NMe)
4/2
;
2) Me
3
SiO
1/2
; Me
2
SiO
2/2
; MeSiO
3/2
; SiO
4/2
;
3) Me
3
Si[SiMe(NH—C═O—NH)
1/2
(NH—C═O—NH
2
)]; Me
3
Si[SiMe(NH—C═O—NH)
2/2
]; Me
3
Si[SiMe
2
(NH—C═O—NH)
1/2
];
4) Me
3
Si[(CMe
2
)s]
1/2
;
5) Me
2
Si(NH—C═O—NH)
1/2
(NH—C═O—NH
2
) MeSi(NH—C═O—NH)
2/2
(NH—C═O—NH
2
); MeSi (NH—C═O—NH)
1/2
(NH—C═O—NH
2
)
2
; Si(NH—C═O—NH)
3/2
(NH—C═O—NH
2
); Si(NH—C═O—NH)
2/2
(NH—C═O—NH
2
)
2
; Si(NH—C═O—NH)
1/2
(NH—C═O—NH
2
)
3
;
6) Me
2
Si(NH—C=O—NH)
1/2
O
1/2
; MeSi(NH—C═O—NH)
2/2
O
1/2
; MeSi(NH—C═O—NH)
1/2
O
2/2
; Si(NH—C═O—NH)
3/2
O
1/2
; Si(NH—C═O—NH)
2/2
O
2/2
; Si(NH—C═O—NH)
1/2
O
3/2
;
7) Me
2
Si[SiMe(NH—C═O—NH)
1/2
(NH—C═O—NH
2
)](NH—C═O—NH)
1/2
; Me
2
Si[SiMe(NH—C═O—NH)
2/2
](NH—C&

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