U.S. patent application number 15/304254 was filed with the patent office on 2017-02-09 for novel bis (alkoxysilyl-vinylene) group-containing silicon compound and production method of same.
This patent application is currently assigned to SHIN-ETSU CHEMICAL CO., LTD.. The applicant listed for this patent is SHIN-ETSU CHEMICAL CO., LTD.. Invention is credited to Taiki KATAYAMA, Takafumi SAKAMOTO, Takahiro YAMAGUCHI.
Application Number | 20170037066 15/304254 |
Document ID | / |
Family ID | 54332136 |
Filed Date | 2017-02-09 |
United States Patent
Application |
20170037066 |
Kind Code |
A1 |
YAMAGUCHI; Takahiro ; et
al. |
February 9, 2017 |
NOVEL BIS (ALKOXYSILYL-VINYLENE) GROUP-CONTAINING SILICON COMPOUND
AND PRODUCTION METHOD OF SAME
Abstract
Provided is an organic silicon compound represented by the
following general formula (1) ##STR00001## (wherein R.sup.1
represents either an alkyl group that has 1 to 20 carbon atoms and
may have a substituted group or a cycloallcyl group that has 3 to
20 carbon atoms and may have a substituted group; R.sup.2
represents either a hydrogen atom or a monovalent hydrocarbon group
that has 1 to 20 carbon atoms and may have a substituted group, and
R.sup.2 may be either identical or different; and each a
independently represents an integer of 1 to 3). The novel
silicon-containing compound of the present invention provides a
cured product of a room temperature-curable organopolysiloxane
composition that is particularly superior in fast curability.
Inventors: |
YAMAGUCHI; Takahiro;
(Annaka-shi, JP) ; SAKAMOTO; Takafumi;
(Annaka-shi, JP) ; KATAYAMA; Taiki; (Annaka-shi,
JP) |
|
Applicant: |
Name |
City |
State |
Country |
Type |
SHIN-ETSU CHEMICAL CO., LTD. |
Tokyo |
|
JP |
|
|
Assignee: |
SHIN-ETSU CHEMICAL CO.,
LTD.
Tokyo
JP
|
Family ID: |
54332136 |
Appl. No.: |
15/304254 |
Filed: |
February 2, 2015 |
PCT Filed: |
February 2, 2015 |
PCT NO: |
PCT/JP2015/052809 |
371 Date: |
October 14, 2016 |
Current U.S.
Class: |
1/1 |
Current CPC
Class: |
C07B 61/00 20130101;
C07F 7/1804 20130101; C07F 7/18 20130101; C07F 7/1876 20130101 |
International
Class: |
C07F 7/18 20060101
C07F007/18 |
Foreign Application Data
Date |
Code |
Application Number |
Apr 25, 2014 |
JP |
2014-091240 |
Claims
1. An organic silicon compound (A) represented by the following
general formula (1) ##STR00015## (wherein R.sup.1 represents either
an alkyl group that has 1 to 20 carbon atoms and may have a
substituted group or a cycloalkyl group that has 3 to 20 carbon
atoms and may have a substituted group; R.sup.2 represents either a
hydrogen atom or a monovalent hydrocarbon group that has 1 to 20
carbon atoms and may have a substituted group, and R.sup.2 may be
either identical or different; and each a independently represents
an integer of 1 to 3).
2. A production method of the organic silicon compound as set forth
in claim 1, comprising adding two hydrogenalkoxysilanes (3) to one
silane compound (2) having two ethynyl groups on an identical
silicon atom, through a hydrosilylation addition reaction
##STR00016## (wherein R.sup.1 represents either an alkyl group that
has 1 to 20 carbon atoms and may have a substituted group or a
cycloalkyl group that has 3 to 20 carbon atoms and may have a
substituted group; R.sup.2 represents either a hydrogen atom or a
monovalent hydrocarbon group that has 1 to 20 carbon atoms and may
have a substituted group, and R.sup.2 may be either identical or
different; and each a independently represents an integer of 1 to
3).
Description
TECHNICAL FIELD
[0001] The present invention relates to a novel organic silicon
compound, especially a novel organic silicon compound useful as a
curing agent with an effect of imparting a superior fast curability
to a room temperature-curable orgariopolysiloxane composition; and
a production method thereof In each molecule of such organic
silicon compound, provided on an identical silicon atom are two
sets of: a hydrolyzable silyl group such as an alkoxysilyl group;
and a structure where two silicon atoms are bonded to each other
through a carbon-carbon double bond (i.e. silyl-vinylene structure
or silyl-ethenylene structure).
BACKGROUND ART
[0002] Conventionally, there have been known various types of room
temperature-curable compositions capable of being cured into
elastomer-like products at room temperature by coming into contact
with the moisture in the air. Particularly, those releasing
alcohols as they cure are characterized in that they do not produce
unpleasant odors and corrode metals, which is why such a type of
room temperature-curable compositions have been preferably used in
performing sealing, bonding and coating in, for example, electric
and electronic equipments.
[0003] Typical examples of the above type of room
temperature-curable composition include a composition composed of a
hydroxyl group-terminated polyorganosiloxane, alkoxysilane and an
organic titanium compound; a composition composed of an alkoxysilyl
group-terminated polyorganosiloxane, alkoxysilane and alkoxy
titanium, a composition composed of a linear polyorganosiloxane
containing a silethylene group(s) and terminated by alkoxysilyl
groups.sub.; alkoxysilane and alkoxy titanium; and a composition
composed of a hydroxyl group-terminated polyorganosiloxane or an
alkoxy group-terminated polyorganosiloxane and an
alkoxy-u-silylester compound (Patent documents 1 to 4).
[0004] Although these compositions exhibit a storage stability, a
water resistance and a moisture resistance to a certain degree,
these properties are not yet completely satisfactory. Further,
these compositions have so far exhibited an insufficient fast
curability.
[0005] As described above, polymers having reactiv a koxysilyl
groups on their terminal ends are known. Since these polymers have
their polymer terminal ends blocked by alkoxysilyl groups from the
beginning, the curability of a composition containing the same is
less likely to change (deteriorate) with time, and a superior
storage stability can thus be achieved. Further, a workability
(viscosity, thixotropy) of such composition can be arbitrarily
controlled, and superior properties (hardness, tensile strength and
elongation at break) can also be achieved as those polymers form
elastomers through reactions with the moisture in the air and then
through cross-liking reactions.
[0006] However, those of dealcoholization type have exhibited an
insufficient curability, since they are less reactive with the
moisture in the air as compared to those of other known curing
types such as deoximation type, dc-acetic acid type and deacetone
type.
[0007] Here, while developments have been made on a room
temperature-curable polyorganosiloxane composition superior in fast
curability and capable of forming a cured product superior in
moisture resistance, those that can be industrially advantageously
produced have not yet been found.
PRIOR ART DOCUMENT
Patent Document
[0008] Patent document 1: Japanese Examined Patent Publication No.
Sho 39-27643
[0009] Patent document 2: JP-A-Sho 55-43119
[0010] Patent document 3: Japanese Examined Patent Publication No.
Hei 7-39547
[0011] Patent document 4: JP-A-Hei 7-331076
[0012] Patent document 5: Japanese Unexamined Patent Application
Publication (Translation of PCT Application) No, 2012-511607
SUMMARY OF THE INVENTION
Problem to be Solved by the invention
[0013] The present invention was made in view of the above issues,
and it is an object of the present invention to provide a curing
agent for a room temperature-curable organopolysiloxane
composition. The curing agent is especially capable of imparting a
fast curability to the room temperature-curable organopolysiloxane
composition, and can thus provide a cured product superior in
storage stability and durability. Further, the room
temperature-curable organopolysiloxane composition can be
industrially advantageously produced using a highly general
material(s).
Means to Solve the Problem
[0014] The inventors of the present invention diligently conducted
a series of studies and completed the invention as follows. That
is, the inventors found that the hydrolyzability of an alkoxy group
in an alkoxysilyl group could be dramatically improved, only when a
linking group adjacent to such alkoxysilyl group was a vinylene
group (ethenylene group). Specifically, the inventors found that by
using a compound that is represented by the following formula (1)
and contains alkoxysilyl-vinylene groups, there could be obtained a
room temperature-curable composition especially superior in fast
curability and capable of forming a cured product with a favorable
storage stability and durability. More specifically, the inventors
were able to arrive at a room temperature-curable
organopolysiloxane composition that can be industrially
advantageously produced due to the fact that a highly general
material(s) (e.g. diorgano dichlorosilane) can be used as a part of
a stalling material(s) for producing the above alkoxysilyl-vinylene
group-containing compound.
[0015] That is, the present invention is to provide an organic
silicon compound represented by the following general formula
(1)
##STR00002##
[0016] (wherein R.sup.1 represents either an alkyl group that has 1
to 20 carbon atoms and may have a substituted group or a cycloalkyl
group that has 3 to 20 carbon atoms and may have a substituted
group; R.sup.2 represents either a hydrogen atom or a monovalent
hydrocarbon group that has 1 to 20 carbon atoms and may have a
substituted group, and R.sup.2 may be either identical or
different; and each a independently represents an integer of 1 to
3). Here, in the present invention, ethenylene group represented by
--CH.dbd.CH-- may be referred to as vinylene group or the like
hereunder.
[0017] Further, the present invention provides a production method
of the organic silicon compound as set forth in <1>,
comprising adding two hydrogenalkoxysilanes (3) to one silane
compound (2) having two ethynyl groups on an identical silicon
atom, through a hydrosilylation addition reaction
##STR00003##
(wherein R.sup.1 represents either an alkyl group that has 1 to 20
carbon atoms and may have a substituted group or a cycloalkyl group
that has 3 to 20 carbon atoms and may have a substituted group;
R.sup.2 represents either a hydrogen atom or a monovalent
hydrocarbon group that has 1 to 20 carbon atoms and may have a
substituted group, and R.sup.2 may be either identical different;
and each a independently represents an integer of 1 to 3).
Effects of the Invention
[0018] The novel silicon-containing compound of the present
invention provides a cured product superior in fast curability, and
allows a composition using the same to be quickly cured when
exposed to the air even after the composition had been stored for
12 months. Here, cured product thus obtained exhibits superior
properties. Therefore, a composition having, as a curing agent, the
novel silicon-containing compound of the present invention (e.g.,
room temperature-curable organopolysiloxane composition) is useful
as a sealing agent, coating material or adhesive agent for use in
certain locations where heat resistance, water resistance and
moisture resistance are required. Particularly, such composition
can be effectively used for construction purposes and applied to an
adhesive agent for electric and electronic pans, where steam
resistance and water resistance are required. Further, since the
silicon-containing compound of the present invention uses a
general-purpose chlorosilane, it can be easily industrialized.
BRIEF DESCRIPTION OF THE DRAWINGS
[0019] FIG. 1 is a diagram showing a .sup.1H-NMR spectrum of a
reaction product ([bis (trimethoxysilyl-vinylene) dimethylsilane])
in a synthesis example 1.
[0020] FIG. 2 is a diagram showing a .sup.1H-NMR spectrum of a
reaction product ([bis (trimethoxysilyl-vinylene) diphenylsilane])
in a synthesis example 2.
MODE FOR CARRYING OUT THE INVENTION
[0021] The present invention is described in greater detail
hereunder.
<Silicon-Containing Compound Terminated by Alkoxysilyl-Vinylene
Group>
[0022] The silicon-containing compound terminated by
alkoxysilyl-vinylene group which is represented by the above
general formula (1) is that having not less than two
alkoxysilyl-vinylene bonds on an identical silicon atom (i.e. bis
(alkoxysilyl-vinylene) silane compound).
[0023] Here, in the above general formula (1), examples of R.sup.I
as an alkyl group having 1 to 20 carbon atoms include 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 pentyl
group, a neopentyl group, a hexyl group, a heptyl group, an octyl
group, a nonyl group, a decyl group, an undecyl group, a dodecyl
group, a tridecyl group, a tetradecyl group, a pentadecyl group, a
hexadecyl group, a heptadecyl group, an octadecyl group, a
nonadecyl group and an eicosyl group. Examples of a cycloalkyl
group include a cyclopentyl group and a cyclohexyl group. Examples
of an alkyl group that has 1 to 20 carbon atoms and may have a
substituted group(s), include an aralkyl group such as a benzyl
group, a 2-phenylethyl group and a 3-phenylpropyl group. Further,
all or a part of the hydrogen atoms in any of these (substituted)
alkyl groups may be substituted by, for example, cyano groups
and/or halogen atoms such as F, Cl and Br. Examples of a
substituted group thus obtained include a 3-chlompropyl group, a
3,3,3-trifluoropropyl group and a 2-cyanoethyl group. Among all the
above examples, preferred as R.sup.1 are alkyl groups having 1 to
6, particularly 1 to 4 carbon atoms. A methyl group and an ethyl
group are more preferred as le, where a methyl group is even more
preferred in terms of availability, productivity and cost.
[0024] R.sup.2 represents a substituted or unsubstitutecl
monovalent hydrocarbon group having 1 to 20 carbon atoms. R.sup.2s
may be identical to or different from one another. Examples of such
R.sup.2 include an alkyl group such as 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 pentyl group, a neopentyl
group, a hexyl group, a heptyl group, an octyl group, a nonyl
group, a decyl group, a undecyl group, a dodecyl group, a tridecyl
group, a tetradecyl group, a pentadecyl group, a hexadecyl group, a
heptadecyl group, an octadecyl group, a nonadecyl group and an
eicosyl group; a cycloalkyl group such as a cyclopentyl group and a
cyclohexyl group; an alkenyl group such as a vinyl group, an allyl
group, a butenyl group, a pentenyl group and a hexenyl group; an
aryl group such as a phenyl group, a tolyl group, a xylyl group and
an .alpha.-, .beta.-naphthyl group; and an aralkyl group such as a
benzyl group, a 2-phenylethyl group and a 3-phenylpropyl group.
R.sup.2 may also be a group obtained by substituting a part of or
all the hydrogen atoms in any of these groups with, for example,
cyano groups and/or halogen atoms such as F, Cl and Br. Examples of
such substituted group include a 3-chloropropyl group,
3,3,3-trifluoropropyl group and a 2-cyanoethyl group. Among all the
above examples, preferred are monovalent hydrocarbon groups having
1 to 10. particularly 1 to 6 carbon atoms.
[0025] A methyl group, an ethyl group and a phenyl group are more
preferred, where a methyl group and a phenyl group are even more
preferred in terms of availability, productivity and cost. Each a
independently represents an integer of 1 to 3. However, it is
preferred that a be either 2 or 3, more preferably 3.
[0026] The organic silicon compound represented by the general
formula (1) of the present invention is mainly used as a curing
agent for a (room temperature) curable composition. Particularly,
those having three methoxy groups on an identical silicon atom in a
molecule (six in total per molecule) contain a trifunctional
alkoxysilane site(s), and are thus useful as curing agents
(cross-linking agent) for a dealcoholized silicone RTV (room
temperature-curable organopolysiloxane composition).
<Production Method of Organic Silicon Compound Represented by
General Formula (1)>
[0027] The silicon-containing compound of the invention which has
two alkoxysilyl-vinylene bonds on an identical silicon atom can,
for example, be easily produced through an addition reaction such
as a hydrosilylation reaction between a silane having two ethynyl
groups on an identical silicon atom and two alkoxysilanes
(hydrogenalkoxysilane). This reaction is expressed by the following
formula [1].
##STR00004##
(In the above formula, R.sup.1, R.sup.2 and a are defined as
above.)
[0028] As an addition reaction catalyst used when adding
alkoxysilane (hydrogenalkoxysilane), platinum group metal-based
catalysts such as a platinum-based catalyst, a palladium-based
catalyst, a rhodium-based catalyst and a ruthenium-based catalyst
are available. Here, a platinum-based catalyst is particularly
preferred. Examples of such platinum-based catalyst include a
platinum black; a catalyst with a solid platinum being supported on
a support such as alumina and silica; a chloroplatinic acid; an
alcohol-modified chloroplatinic acid; a complex of a chloroplatinic
acid and olefin; and a complex of platinum and vinylsiloxane. These
kinds of platinum may be used in a so-called catalytic amount, and
may, for example, be used in an amount of 0.1 to 1,000 ppm,
particularly 0.5 to 100 ppm in terms of platinum group metal, with
respect to alkoxysilanes.
[0029] It is desired that this reaction be performed at a
temperature of 50 to 120.degree. C., particularly 60 to 100.degree.
C., for 0.5 to 12 hours, particularly 1 to 6 hours, and the
reaction can be performed without a solvent. However, an
appropriate solvent such as toluene and xylene may be used,
provided that no adverse impact will be inflicted upon the above
addition reaction or the like.
[0030] In an addition reaction to silyl-acetylene group
(silyl-ethynyl group), a geometric isomer represented by the
following reaction formula [2] will, for example be produced. In
such geometric isomer, the production of E isomer (trans isomer) is
highly selective and highly reactive. Since there will be no
adverse impact on the properties of the silicon-containing compound
of the present invention, these geometric isomers need not be
separated at the time of use.
##STR00005##
[0031] Specific examples of the organic silicon compound
represented by the general formula (1) of the invention include
those represented by the following structural formulae.
##STR00006## ##STR00007##
WORKING EXAMPLE
[0032] The present invention is described in detail hereunder with
reference to working examples (synthesis examples), reference
examples and comparative reference examples. However, the present
invention is not limited to the following working examples.
Further, in the specific examples below, "part" refers to "part by
mass," and viscosity refers to a value measured by a rotary
viscometer at 25.degree. C.
Working Example 1
<Synthesis of Silicon-Containing Compound Having Two
Alkoxysilyl-Vinylene Groups on an Identical Silicon Atom-[Bis
(Trimethoxysilyl-Vinylene) Dimethylsilane]>
[0033] Diethynyldimethylsilane of 35.0 g (0.323 mol), a 0.5 wt %
toluene solution of a chloroplatinic acid
(H.sub.2PtCl.sub.6.6H.sub.2O) of 0.10 g and toluene of 50 mL were
put into a 500 mL four-necked separable flask equipped with a
mechanical stirrer, a thermometer and a dropping funnel, followed
by delivering thereinto 83.01 g (0.678 mol) of trimethoxysilane by
drops. Later, stirring was performed at 85.degree. C. for 6 hours,
followed by performing distillation so as to obtain 106.2 g (yield
90%) of a silicon compound [bis (trimethoxysilyl-ethylene)
dimethylsilane] shown below. Next, a .sup.1HNMR chart of this
silicon compound was analyzed, and it was confirmed that the
silicon compound was the target bis (trimethoxysilyl-vinylene)
dimethylsilane (trans:cis=8:1) (compound shown below). This
reaction is shown in the following formula [3].
##STR00008##
[0034] The .sup.1H-NMR spectrum data of this compound are as
follows.
[0035] .sup.1H-NMR (400 MHz, C.sub.6D.sub.6, .delta. (ppm)):0.00
(s, 6H), 3.36 (s, 18H), 6.47 (d, 2H), 7.10 (d, 2H)
Working Example 2
<Synthesis of Silicon-Containing Compound Having Two
Alkoxysilyl-Vinylene Groups on an Identical Silicon Atom-[Bis
(Trimethoxysilyl-Vinylene) Diphenyl Silane]>
[0036] Diethynyldiphenylsilane of 34.9 g (0.151 mol), a 0.5 wt %
toluene solution of a chloroplatinic acid
(H.sub.2PtCl.sub.6.6H.sub.2O) of 0.10 g and toluene of 50 mL were
put into a 500 mL four-necked separable flask equipped with a
mechanical stirrer, a thermometer and a dropping funnel, followed
by delivering thereinto 38.5 g (0.315 mol) of trimethoxysilane by
drops. Later, stirring was performed at 85.degree. C. for 6 hours,
followed by performing distillation so as to obtain 56.5 g (yield
88%) of a silicon compound [bis (trimethoxysilyl-ethylene
diphenylsilane] shown below. Next, a .sup.1HNMR chart of this
silicon compound was analyzed, and it was confirmed that the
silicon compound was the target his (trimethoxysilyl-vinylene)
diphenylsilane (trans:cis=9:1) (compound shown below). This
reaction is shown in the following formula [4].
##STR00009##
[0037] The .sup.1H-NMR spectrum data of this compound are as
follows.
[0038] .sup.1H-NMR (400 MHz, C.sub.6D.sub.6, .delta. (ppm)): 3.61
(s, 18H), 6.45 (d, 2H), 7.31 (d, 2H), 7.36-7.55 (in, 10H),
Reference Example 1
[0039] Combined were 100 parts of a dimethylpolysiloxane having a
viscosity of 5,000 mPas, and a molecular chain whose two ends are
blocked by hydroxyl groups (or hydroxydimethylsiloxy groups); 4.9
parts of bis (trimethoxysilyl-vinylene) dimethylsilane; and 0.75
parts of tetramethylguanidylpropyltrimethoxysilane, followed by
keeping mixing them under a moisture-blocked condition until a
uniform level had been reached, thus obtaining a composition.
Reference Example 2
[0040] Combined were 100 parts of a dimethylpolysiloxane having a
viscosity of 5,000 mPas, and a molecular chain whose two ends are
blocked by hydroxyl groups (or hydroxydimethylsiloxy groups); 4.9
parts of bis (trimethoxysilyl-vinylene) dimethylsilane; and 1.0
part of an organic aluminum compound which was a mono
(dipivaloylmethane) aluminum bis (ethylacetoacetate) chelate having
an average structure represented by the following structural
formula (2), followed by keeping mixing them under a
moisture-blocked condition until a uniform level had been reached,
thus obtaining a composition.
##STR00010##
Reference Example 3
[0041] Combined were 100 parts of a dimethylpolysiloxane having a
viscosity of 5,000 mPas, and a molecular chain whose two ends are
blocked by hydroxyl groups (or hydroxydimethylsiloxy groups); 4.9
parts of bis (trimethoxysilyl-vinylene) dimethylsilane; and 0.2
parts of a compound which was an N,N,N',N',N'',
N''-hexamethyl-N'''-(trimethylsilylmethyl)- phosphorimidic tri
amide represented by the following structural formula (3), followed
by keeping mixing them under a moisture-blocked condition until a
uniform level had been reached, thus obtaining a composition.
##STR00011##
Reference Example 4
[0042] A composition was obtained in the similar manner as
reference example 1, except that 6,6 parts of bis
(trimethoxysilyl-ethylene) diphenylsilane was used instead of bis
(trimethoxysilyl-vinylene) dimethylsilane.
Comparative Reference Examples 1 to 3
[0043] Compositions were obtained in the similar manners as
reference examples 1 to 3, except that there were used 4.1 parts of
a silicon compo (vinyltrunethoxysilane) represented by the
following structural formula (4) instead of bis (trimethoxy
-vinylene) dimethylsilane.
##STR00012##
Comparative Reference Examples 4 to 6
[0044] Compositions were obtained in the manners as reference
examples 1 to 3, except that there used 3.8 parts of a silicon
compound (methyltrimethoxysilane) represented by the following
structural formula (5) instead of bis (trimethoxysilyl-vinylene)
dimethylsilane.
##STR00013##
Comparative Reference Example 7
[0045] A composition was obtained in the similar manner as
reference example 1, except that there were used 4.5 parts of a
silicon compound (1,6-bis (trimethoxysilyl) hexane) represented by
the following structural formula (6) instead of bis
(trimethoxysilyl-vinylene) dimethylsilane.
##STR00014##
[Measurement of Tack-Free Time]
[0046] There was measured a tack-free time of each of the
compositions obtained in reference examples 1 to 4; and comparative
reference examples 1 to 7.
[0047] In addition, each of the compositions obtained in reference
examples 1 to 4; and comparative reference examples 1 to 7 was
pushed out into a sheet-like shape of a thickness of 2 mm,
immediately after they had been produced. The sheet-shaped
composition was then exposed to an air of 23.+-.2.degree. C.,
50.+-.5% RH, and left under the same atmosphere for three days so
as to obtain a cured product whose properties(initial properties)
were then measured in accordance with HS K-6249. Here, a hardness
was measured by a hardness meter which was an A-type durometer
described in JIS K-6249.
[0048] Further, similar measurements were performed on a product
obtained by storing the above cured product in a thermo-hygrostat
of 85.degree. C., 85% RH for 7 days. Furthermore, similar
measurements were also performed on a product obtained by heating
the above cured product in an oven of 150.degree. C. for 10
days.
[0049] Table 1 shows the results of reference examples 1 and d
comparative reference examples 1, 4 and 7. Table 2 shows the
results of reference example 2; and comparative reference examples
2 and 5. Table 3 shows the results of reference example 3; and
comparative reference examples 3 and 6.
TABLE-US-00001 TABLE 1 Comparative Comparative Comparative
Reference Reference Reference Reference Reference Measurement
result Example 1 Example 4 Example 1 Example 4 Example 7 Tack-free
time (min) 5 3 60< 60< 60< Initial Hardness 22 25 16 6 24
RTV (Durometer A) 7 days Elongation (%) 105 130 110 235 0.33
Tensile strength 0.45 0.52 0.27 0.19 100 (MPa) Moisture Hardness 10
16 4 1 8 resistance (Durometer A) 85.degree. C./85% RH Elongation
(%) 155 165 430 365 120 7 days Tensile strength 0.25 0.27 0.22 0.08
0.15 (MPa) Heat Hardness 20 20 15 12 23 resistance (Durometer A)
150.degree. C. Elongation (%) 140 130 105 100 120 10 days Tensile
strength 0.47 0.35 0.23 0.22 0.29 (MPa)
TABLE-US-00002 TABLE 2 Comparative Comparative Reference Reference
Reference Example Example Example Measurement result 2 2 5
Tack-free time (min) 2 10 15< Initial Hardness 12 4 0 RTV
(Durometer A) 7 days Elongation (%) 105 210 430 Tensile strength
0.27 0.15 0.13 (MPa) Moisture Hardness 11 0.5 0 resistance
(Durometer A) 85.degree. C./85% Elongation (%) 150 375 530 RH 7
days Tensile strength 0.33 0.16 0.13 (MPa) Heat Hardness 18 15 14
resistance (Durometer A) 150.degree. C. Elongation (%) 125 190 215
10 days Tensile strength 0.45 0.38 0.38 (MPa)
TABLE-US-00003 TABLE 3 Comparative Comparative Reference Reference
Reference Example Example Example Measurement result 3 3 6
Tack-free time (min) 4 60< 60< Initial Hardness 25 16 8 RTV
(Durometer A) 7 days Elongation (%) 100 105 215 Tensile strength
0.46 .sup. 0.29 0.22 (MPa) Moisture Hardness 15 10 6 resistance
(Durometer A) 85.degree. C./85% Elongation (%) 135 165 260 RH 7
days Tensile strength 0.33 .sup. 0.26 0.25 (MPa) Heat Hardness 26
18 10 resistance (Durometer A) 150.degree. C. Elongation (%) 115
135 100 10 days Tensile strength 0.51 .sup. 0.31 0.16 (MPa)
[0050] As described above, the organic silicon compound of the
present invention provides a cured product superior in fast
curability and durability, and can thus serve as a curing agent
component effective for a room temperature-curable
organopolysiloxane composition.
[0051] However, the present invention is not limited to the above
embodiment. The above embodiment is simply an example; and any
embodiment belongs to the technical scope of the present invention,
if the embodiment has a composition substantially identical to that
of the technical ideas described in the claims of the invention,
and brines about the similar function effects.
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