CA1133169A - Curable solventless organopolysiloxane compositions - Google Patents
Curable solventless organopolysiloxane compositionsInfo
- Publication number
- CA1133169A CA1133169A CA322,672A CA322672A CA1133169A CA 1133169 A CA1133169 A CA 1133169A CA 322672 A CA322672 A CA 322672A CA 1133169 A CA1133169 A CA 1133169A
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- Prior art keywords
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- mol
- parts
- silicon hydride
- curable composition
- Prior art date
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/54—Silicon-containing compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
- C08L83/04—Polysiloxanes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/045—Polysiloxanes containing less than 25 silicon atoms
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/12—Polysiloxanes containing silicon bound to hydrogen
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/20—Polysiloxanes containing silicon bound to unsaturated aliphatic groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/70—Siloxanes defined by use of the MDTQ nomenclature
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Abstract
ABSTRACT OF THE DISCLOSURE
What is disclosed is platinum catalyzed mixtures of silicon hydride and CH2=CHSi- containing siloxanes which also contain [CH2=CH(CH3)2SiO]2Si(C6H5)2 as a reactive diluent which give curable products having improved handling properties while retaining essential mechanical properties in the cured composition.
What is disclosed is platinum catalyzed mixtures of silicon hydride and CH2=CHSi- containing siloxanes which also contain [CH2=CH(CH3)2SiO]2Si(C6H5)2 as a reactive diluent which give curable products having improved handling properties while retaining essential mechanical properties in the cured composition.
Description
~33~
The present invention relates to curable organo-polysiloxane resins containing a reactive diluent.
Organopolysiloxane resins in which the substituent organic groups are methyl, phenyl, vinyl and/or similar organic groups are well-known~ These materials cure through a variety of mechanisms, such as peroxide catalyzed vinyl groups on silicon or by the platinum catalyzed addition of silicon hydride to alken~l groups on silicon. The properties of these organopolysiloxane resins such as toughness and retention of strength at high temperatures make them useful in casting resin applications.
The resins that are useful for casting applications are those that have higher viscosities, on the order of 5.0 to 200 Pa-s or higher. These resins, even though they have the desir~d strengths, have one important disadvantage. Because of their high viscosities they are extremely difficult to handle in use. They do not pour rapidly and have slow flow when cast into place.
The problem is, therefore, posed as to how one can use the high viscosit~ resins for their desirable properties and at the same time obtain desirable handling properties.
An obvious solution is to dilute the resins with solvent but this approach leads to bubble entrapment when the casting resin is heated to cure it. It also leads to the time-consuming step of solvent removal ~rom the cast resin.
Most recent attempts to solve the handling problem have been to incorporate a low molecular weight crosslinker in the system. For example, Clark in U.S. Patent 2,894,930 shows a one-part, curable casting resin wherein he sugyests using (CH2-C~(C~3)2SiO)2Si(C6Hs)2 as a portion of the reactive alkenyl containing resin. The materials are cured through the use of peroxide catalysts. These materials have the advantage of being ~33~
one-part, that is, all the essential ingredients can be mixed together and stored without the material curing. The disadvantage r of course, is that fact that the peroxide cured, one-part materials require a long period of time to cure.
Mink et al., in U.S. Patent 3,944/519, overcome the latter problem by increasing the rate of cure oE such resins by changing ~he cure system from the peroxide cured vinyl to the platinum catalysis of the silicon hydride addition to alkenyl groups, i.e. --SiH ~ CH2=CHSi-~ P >
-SiCH2CH2Si--. Thus, Mink et al. utilized low molecular ~eight (low viscosity) silicon hydride crosslin~er organopolysiloxanes in a vinyl containing organopolysiloxane to enhance the cure rate and also to reduce the viscosity of the vinylsiloxane resin so that it could be easily handled. The patent teaches that only specific silicon hydride containing crosslinkers work. The use of low molecular weight vinyl containing diluents is not shown or ; suggested therein.
It has been found that by adding a specific low molecular weight vinyl containing diluent, lower viscosities of the casting resins can be obtained without sacrificing the desirable mechanical properties of the higher viscosity casting resin.
This invention consists of an improved curable composition consisting essentially of a mixture of ~a) an organopolysiloxane containing from 67 to 85 mol percent C6H5SiO3/2 units and 33 to 15 mol percent of CH2=CH(CH3)2SiOl/2 units, said organopolysiloxane having an average of at least 8 silicon atoms per molecule; (b) a silicon hydride containing polysiloxane crosslinker for (a), said (b) being present in an amount sufficient to provide about 0.9 to 1.1 mol of silicon hydride per .nol of CH2=CHSi present in (a) and (d); (c) a platinum catalyst in ~3~
an amount sufficient to catalyze the reaction of the silicon hydride with the CH2=CHSi-; the improvement comprising adding a reactive diluent ~d) having the formula [CH2=CH(CH3)2siO]2si(c6H5)2-In this invention, the organopolysiloxane resin (a) isthe base resin. The critical feature of the resin (a) is that it have a sufficiently high viscosity to give the desired mechanical strength to the cured composition. The resin (a) is essentially the same as that described in Mink et al., discussed above~ and ~ 10 consists of monophenylsiloxy units in the range 67 to 85 mol - percent; dimethylvinylsiloxy units in the range of 33 to 15 mol percent. Preferred for the resin (a) are 75 mol percent monophenylsiloxy units and 25 mol percent of the dimethylvinyl-siloxy units.
This resin is easily prepared by conventional hydrolysis of the corresponding chloro or alkoxysllanes and condensation techniques. Although there does not appear to be any upper limit on the molecular weight of the resin ~a), it should have a degree of polymerization of at least 8 silicon atoms per molecule. This is to ensure adequate physical strengths in the final product.
The resin (a) can also be treated, for example, by alkaline condensation catalysts, to reduce the silanol content of the resin.
The silicon hydride containing siloxane (b) serves as a crosslinker and curing agent in the curable composition. This material can be any silicon hydride containing silane or siloxane that is compatible and gives the cured composition the desired properties. This material can be, for example, the polymer found in the Mink et al. patent at column 2, lines 23-25 or [H(CH3)2SiO]2Si(C6H5)2 or ~H(CH3)2SiO~3SiC6H5. The crosslinker ~333L~
must have at least two (2) silicon hydrogens per molecule. There must be enough of (b) present to give from 0.9 to 1.1 mol of silicon hydride per mol of alkenyl groups in the curable composition. Preferred is a ratio of 1 mol of silicon hydride to 1 mol of alkenyl for the best results. The crosslinkers (b) can be prepared by conventional techniques known to those skilled in the art, for example, the cohydrolysis of the corresponding silanes. -The platinum catalyst (c) can be any of the well-known forms of catalytic platinum, ran~ing from finely divided platinum metal to platinum on various carriers to the chloroplatinic acid and complexed platinum compounds. Chloroplatinic acid in a small amount of solvent or [(R3P)2PtCl]2 where R is methyl, ethyl, propyl or butyl are preferred There should be at least 0.1 parts by weight of platinum per million parts by weight of the combined total of components (a), (b) and (d) and 1-20 parts Pt per million parts is preferred.
The unique component of this invention is the component (d), the vinyl containing siloxane diluent, [CH2=CH(cH3)2siO]2si(c6H5)2-On mixing this diluent (d) with the componen~ ~a) in a ratio of (d) to (a) of from 20/80 to 50/50, a solventless material is produced which has a maximum viscosity of about 2.5 Pa-s. The preferred ratio is 25 parts of (d) to 75 parts of (a)~ This specific material is the only one of many similar materials that was effective in this invention. [CH2=CH(CH3)2Si]2O was too volatile while [(C6H5)(CH3)(CH2=CH)Si]2O and [CH2=CH(CH3)2Sio]2SiCH3(C6Hs), although non-volatile, reduced the mechanical properties of the cured resin. This material is easily ~3~
prepared by the same methods as indicated for the component (b) above Generally for a two-component system, the component (d) is mixed, with a small portion of the base resin (a) and the catalyst required for cure, into one package. The remainder of the base resin (a) and the crosslinker (b) are mixed together and form a second package. The means and manner for mixing these individual materials is not critical as long as the materials are homogeneous. The two packages can then be mixed together at the appropriate time for their use and cast into place. Upon heating, the composition cures. If other materials are to be mixed with the composition, they should be incorporated in the individual packages during their preparation rather than adding those materials at the final mixing of the whole composition. Other materials that can be incorporated in ~he resin composition of this invention are the conventional fi:Llers such as glass fibers, inely divided silica, crushed quartz, powdered glass, asbestos, talc, carbon black, iron oxide, titanium oxide, magnesium oxide or mixtures thereof. Also included are pigments, dyes, oxidation inhibitors, cure inhibitors and release a~ents. -The curable composition can be employed in any conventional manner for casting or impregnating.
The components (a), (b), (c) and (d) are mixed together with any of ~he above desired additives and mixed to make homogeneous. It is then fabricated into the desired ~orm and cured, usually at elevated temperatures, for example, 100-150C.
It may be desirable in some cases to post cure the cured material at elevated temperatures, for example, up to 200C.
The following examples are by way of comparison with the systems currently in the prior art. The examples are not intended ~L33:~60~
as limiting the invention delineated in the claims.
Example 1 A base resin was prepared consisting of 75 mol percent monophenylsiloxy units and 25 mol percent of vinyldimethylsiloxy units and was designated "A". Various types of crosslinkers ; designated "B", "C" and "D" were prepared and mixed with A
; according to conventional techniques in the amounts shown in Table I. The mixture of B with A is the example of the prior art shown in Mink et al., U.S. 3,944,519 at Table II, middle columnO B is 10 [H(CH3)2siO72si(c6H5)2; C is [H(cH3)2sio]3sic6Hs and D is 35 mole percent diphenylsiloxy units; 55 mole % HCH3SiO units and 10 mole percent (CH3)3SiOl/2 units. The catalyst was 1% [(C4Hg)3P]2PtC12 in toluene. Runs 1, 2 and 3 are outside the scope of the invention and represent the prior art.
Runs 4, 5 and 6 illustrate the invention and show the effect of the addition of (d) (CH2=CH(CH3)2SiO)2Si(C6H5)2.
Two-part compositions were prepared wherein part one was the base resin (a) and the crosslinker (b) and the second part was the component (d) and the catalyst and, a small amount of component (a) as a carrier. The ratio of part one to part two was 10:1.
The results are shown in Table II helow.
Example 2 This example serves to illustrate the comparison between the prior art diluent (~ViMeSi)2O and the present diluent. As the amount of the prior art diluent is increased, the flex strength of the resulting resin is reduced. The increase in diluent is to decrease the viscosity so that the base resin can be easily handled.
Runs 7, 8 and 9 on Table III show the use of (~ViMeSi)2O
as the reactive diluent wherein 0 is C6Hs-, Vi is CH2=CH- and Me ~L~3~
is CH3~. Two part compositions were again prepared wherein part one was the base resin (a) and the crosslinker (b) and the second part was (~ViMeSi)2O, the catalyst and a small amoun~ of component (a) as a carrier. The ratio of part one to part two was 10:1.
; The catalyst was the same as used in Example 1.
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The present invention relates to curable organo-polysiloxane resins containing a reactive diluent.
Organopolysiloxane resins in which the substituent organic groups are methyl, phenyl, vinyl and/or similar organic groups are well-known~ These materials cure through a variety of mechanisms, such as peroxide catalyzed vinyl groups on silicon or by the platinum catalyzed addition of silicon hydride to alken~l groups on silicon. The properties of these organopolysiloxane resins such as toughness and retention of strength at high temperatures make them useful in casting resin applications.
The resins that are useful for casting applications are those that have higher viscosities, on the order of 5.0 to 200 Pa-s or higher. These resins, even though they have the desir~d strengths, have one important disadvantage. Because of their high viscosities they are extremely difficult to handle in use. They do not pour rapidly and have slow flow when cast into place.
The problem is, therefore, posed as to how one can use the high viscosit~ resins for their desirable properties and at the same time obtain desirable handling properties.
An obvious solution is to dilute the resins with solvent but this approach leads to bubble entrapment when the casting resin is heated to cure it. It also leads to the time-consuming step of solvent removal ~rom the cast resin.
Most recent attempts to solve the handling problem have been to incorporate a low molecular weight crosslinker in the system. For example, Clark in U.S. Patent 2,894,930 shows a one-part, curable casting resin wherein he sugyests using (CH2-C~(C~3)2SiO)2Si(C6Hs)2 as a portion of the reactive alkenyl containing resin. The materials are cured through the use of peroxide catalysts. These materials have the advantage of being ~33~
one-part, that is, all the essential ingredients can be mixed together and stored without the material curing. The disadvantage r of course, is that fact that the peroxide cured, one-part materials require a long period of time to cure.
Mink et al., in U.S. Patent 3,944/519, overcome the latter problem by increasing the rate of cure oE such resins by changing ~he cure system from the peroxide cured vinyl to the platinum catalysis of the silicon hydride addition to alkenyl groups, i.e. --SiH ~ CH2=CHSi-~ P >
-SiCH2CH2Si--. Thus, Mink et al. utilized low molecular ~eight (low viscosity) silicon hydride crosslin~er organopolysiloxanes in a vinyl containing organopolysiloxane to enhance the cure rate and also to reduce the viscosity of the vinylsiloxane resin so that it could be easily handled. The patent teaches that only specific silicon hydride containing crosslinkers work. The use of low molecular weight vinyl containing diluents is not shown or ; suggested therein.
It has been found that by adding a specific low molecular weight vinyl containing diluent, lower viscosities of the casting resins can be obtained without sacrificing the desirable mechanical properties of the higher viscosity casting resin.
This invention consists of an improved curable composition consisting essentially of a mixture of ~a) an organopolysiloxane containing from 67 to 85 mol percent C6H5SiO3/2 units and 33 to 15 mol percent of CH2=CH(CH3)2SiOl/2 units, said organopolysiloxane having an average of at least 8 silicon atoms per molecule; (b) a silicon hydride containing polysiloxane crosslinker for (a), said (b) being present in an amount sufficient to provide about 0.9 to 1.1 mol of silicon hydride per .nol of CH2=CHSi present in (a) and (d); (c) a platinum catalyst in ~3~
an amount sufficient to catalyze the reaction of the silicon hydride with the CH2=CHSi-; the improvement comprising adding a reactive diluent ~d) having the formula [CH2=CH(CH3)2siO]2si(c6H5)2-In this invention, the organopolysiloxane resin (a) isthe base resin. The critical feature of the resin (a) is that it have a sufficiently high viscosity to give the desired mechanical strength to the cured composition. The resin (a) is essentially the same as that described in Mink et al., discussed above~ and ~ 10 consists of monophenylsiloxy units in the range 67 to 85 mol - percent; dimethylvinylsiloxy units in the range of 33 to 15 mol percent. Preferred for the resin (a) are 75 mol percent monophenylsiloxy units and 25 mol percent of the dimethylvinyl-siloxy units.
This resin is easily prepared by conventional hydrolysis of the corresponding chloro or alkoxysllanes and condensation techniques. Although there does not appear to be any upper limit on the molecular weight of the resin ~a), it should have a degree of polymerization of at least 8 silicon atoms per molecule. This is to ensure adequate physical strengths in the final product.
The resin (a) can also be treated, for example, by alkaline condensation catalysts, to reduce the silanol content of the resin.
The silicon hydride containing siloxane (b) serves as a crosslinker and curing agent in the curable composition. This material can be any silicon hydride containing silane or siloxane that is compatible and gives the cured composition the desired properties. This material can be, for example, the polymer found in the Mink et al. patent at column 2, lines 23-25 or [H(CH3)2SiO]2Si(C6H5)2 or ~H(CH3)2SiO~3SiC6H5. The crosslinker ~333L~
must have at least two (2) silicon hydrogens per molecule. There must be enough of (b) present to give from 0.9 to 1.1 mol of silicon hydride per mol of alkenyl groups in the curable composition. Preferred is a ratio of 1 mol of silicon hydride to 1 mol of alkenyl for the best results. The crosslinkers (b) can be prepared by conventional techniques known to those skilled in the art, for example, the cohydrolysis of the corresponding silanes. -The platinum catalyst (c) can be any of the well-known forms of catalytic platinum, ran~ing from finely divided platinum metal to platinum on various carriers to the chloroplatinic acid and complexed platinum compounds. Chloroplatinic acid in a small amount of solvent or [(R3P)2PtCl]2 where R is methyl, ethyl, propyl or butyl are preferred There should be at least 0.1 parts by weight of platinum per million parts by weight of the combined total of components (a), (b) and (d) and 1-20 parts Pt per million parts is preferred.
The unique component of this invention is the component (d), the vinyl containing siloxane diluent, [CH2=CH(cH3)2siO]2si(c6H5)2-On mixing this diluent (d) with the componen~ ~a) in a ratio of (d) to (a) of from 20/80 to 50/50, a solventless material is produced which has a maximum viscosity of about 2.5 Pa-s. The preferred ratio is 25 parts of (d) to 75 parts of (a)~ This specific material is the only one of many similar materials that was effective in this invention. [CH2=CH(CH3)2Si]2O was too volatile while [(C6H5)(CH3)(CH2=CH)Si]2O and [CH2=CH(CH3)2Sio]2SiCH3(C6Hs), although non-volatile, reduced the mechanical properties of the cured resin. This material is easily ~3~
prepared by the same methods as indicated for the component (b) above Generally for a two-component system, the component (d) is mixed, with a small portion of the base resin (a) and the catalyst required for cure, into one package. The remainder of the base resin (a) and the crosslinker (b) are mixed together and form a second package. The means and manner for mixing these individual materials is not critical as long as the materials are homogeneous. The two packages can then be mixed together at the appropriate time for their use and cast into place. Upon heating, the composition cures. If other materials are to be mixed with the composition, they should be incorporated in the individual packages during their preparation rather than adding those materials at the final mixing of the whole composition. Other materials that can be incorporated in ~he resin composition of this invention are the conventional fi:Llers such as glass fibers, inely divided silica, crushed quartz, powdered glass, asbestos, talc, carbon black, iron oxide, titanium oxide, magnesium oxide or mixtures thereof. Also included are pigments, dyes, oxidation inhibitors, cure inhibitors and release a~ents. -The curable composition can be employed in any conventional manner for casting or impregnating.
The components (a), (b), (c) and (d) are mixed together with any of ~he above desired additives and mixed to make homogeneous. It is then fabricated into the desired ~orm and cured, usually at elevated temperatures, for example, 100-150C.
It may be desirable in some cases to post cure the cured material at elevated temperatures, for example, up to 200C.
The following examples are by way of comparison with the systems currently in the prior art. The examples are not intended ~L33:~60~
as limiting the invention delineated in the claims.
Example 1 A base resin was prepared consisting of 75 mol percent monophenylsiloxy units and 25 mol percent of vinyldimethylsiloxy units and was designated "A". Various types of crosslinkers ; designated "B", "C" and "D" were prepared and mixed with A
; according to conventional techniques in the amounts shown in Table I. The mixture of B with A is the example of the prior art shown in Mink et al., U.S. 3,944,519 at Table II, middle columnO B is 10 [H(CH3)2siO72si(c6H5)2; C is [H(cH3)2sio]3sic6Hs and D is 35 mole percent diphenylsiloxy units; 55 mole % HCH3SiO units and 10 mole percent (CH3)3SiOl/2 units. The catalyst was 1% [(C4Hg)3P]2PtC12 in toluene. Runs 1, 2 and 3 are outside the scope of the invention and represent the prior art.
Runs 4, 5 and 6 illustrate the invention and show the effect of the addition of (d) (CH2=CH(CH3)2SiO)2Si(C6H5)2.
Two-part compositions were prepared wherein part one was the base resin (a) and the crosslinker (b) and the second part was the component (d) and the catalyst and, a small amount of component (a) as a carrier. The ratio of part one to part two was 10:1.
The results are shown in Table II helow.
Example 2 This example serves to illustrate the comparison between the prior art diluent (~ViMeSi)2O and the present diluent. As the amount of the prior art diluent is increased, the flex strength of the resulting resin is reduced. The increase in diluent is to decrease the viscosity so that the base resin can be easily handled.
Runs 7, 8 and 9 on Table III show the use of (~ViMeSi)2O
as the reactive diluent wherein 0 is C6Hs-, Vi is CH2=CH- and Me ~L~3~
is CH3~. Two part compositions were again prepared wherein part one was the base resin (a) and the crosslinker (b) and the second part was (~ViMeSi)2O, the catalyst and a small amoun~ of component (a) as a carrier. The ratio of part one to part two was 10:1.
; The catalyst was the same as used in Example 1.
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Claims (5)
1. An improved curable composition consisting essentially of a mixture of (a) an organopolysiloxane containing from 67 to 85 mol percent C6H5SiO3/2 units and 33 to 15 mol percent of CH2=CH(CH3)2SiO1/2 units, said organo-polysiloxane having an average of at least 8 silicon atoms per molecule;
(b) a silicon hydride containing polysiloxane crosslinker for (a), said (b) being present in an amount sufficient to provide about 0.9 to 1.1 mol of silicon hydride per mol of CH2=CHSi= present in (a) and (d);
(c) a platinum catalyst in an amount sufficient to catalyze the reaction of the silicon hydride with the CH2=CHSi-; and (d) a reactive diluent having the formula [CH2=CH(CH3)2SiO]2Si(C6H5)2
(b) a silicon hydride containing polysiloxane crosslinker for (a), said (b) being present in an amount sufficient to provide about 0.9 to 1.1 mol of silicon hydride per mol of CH2=CHSi= present in (a) and (d);
(c) a platinum catalyst in an amount sufficient to catalyze the reaction of the silicon hydride with the CH2=CHSi-; and (d) a reactive diluent having the formula [CH2=CH(CH3)2SiO]2Si(C6H5)2
2. A curable composition as claimed in claim 1 wherein (c), the platinum catalyst, is present in an amount sufficient to provide at least 0.1 parts by weight platinum per million parts of the combined weight of (a), (b) and (d).
3. A curable composition as claimed in claim 1, wherein (b) is present in an amount sufficient to provided about 1.0 mol of silicon hydride per mol of CH2=CHSi- in (a) and (d).
4. A curable composition as claimed in claim 1, wherein (d) is present in an amount of 20 to 50 parts by weight based on 80 to 50 parts by weight of (a) present.
5. A curable composition as claimed in claim 4 wherein the amount of (d) present is 25 parts and there is present 75 parts of (a).
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US91279478A | 1978-06-05 | 1978-06-05 | |
| US912,794 | 1978-06-05 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1133169A true CA1133169A (en) | 1982-10-05 |
Family
ID=25432457
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA322,672A Expired CA1133169A (en) | 1978-06-05 | 1979-03-02 | Curable solventless organopolysiloxane compositions |
Country Status (5)
| Country | Link |
|---|---|
| JP (1) | JPS54159459A (en) |
| CA (1) | CA1133169A (en) |
| DE (1) | DE2922296C3 (en) |
| FR (1) | FR2428059A1 (en) |
| GB (1) | GB2022115B (en) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0216376B1 (en) * | 1982-09-10 | 1991-08-07 | General Electric Company | Process for making solventless release diorganopolysiloxane composition |
| JPH08127657A (en) * | 1994-10-31 | 1996-05-21 | Dow Corning Asia Ltd | Production of cured diphenylsiloxane and cured product |
| JP2005162859A (en) | 2003-12-02 | 2005-06-23 | Dow Corning Toray Silicone Co Ltd | Addition reaction curing type organopolysiloxane resin composition and optical member |
| JP4801320B2 (en) | 2003-12-19 | 2011-10-26 | 東レ・ダウコーニング株式会社 | Addition reaction curable organopolysiloxane resin composition |
| JP4840564B2 (en) * | 2005-10-07 | 2011-12-21 | 信越化学工業株式会社 | Photo-curable coating agent and article for forming hard protective film |
| RU2401846C2 (en) * | 2006-04-25 | 2010-10-20 | Учреждение Российской академии наук Институт синтетических полимерных материалов им. Н.С. Ениколопова РАН (ИСПМ РАН) | Functional polyorganosiloxanes and curable composition based on said polyorganosiloxanes |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB797979A (en) * | 1956-04-12 | 1958-07-09 | Midland Silicones Ltd | Improvements in or relating to organo-silicon compositions |
| US2915497A (en) * | 1956-11-29 | 1959-12-01 | Dow Corning | Solventless siloxane resins |
| GB823039A (en) * | 1956-12-19 | 1959-11-04 | Midland Silicones Ltd | Improvements in or relating to organosiloxane resins |
| US3884866A (en) * | 1973-04-13 | 1975-05-20 | Gen Electric | High strength organopolysiloxane compositions |
| US3944519A (en) * | 1975-03-13 | 1976-03-16 | Dow Corning Corporation | Curable organopolysiloxane compositions |
| FR2343779A1 (en) * | 1976-03-10 | 1977-10-07 | Dow Corning | Curable compsns for encapsulating electronic appts - comprising monophenylsiloxy-dimethylvinylsiloxy copolymer-hydrogen functional siloxane compsns, with platinum catalyst |
-
1979
- 1979-03-02 CA CA322,672A patent/CA1133169A/en not_active Expired
- 1979-05-04 JP JP5519479A patent/JPS54159459A/en active Granted
- 1979-05-31 DE DE2922296A patent/DE2922296C3/en not_active Expired
- 1979-06-01 FR FR7914116A patent/FR2428059A1/en active Granted
- 1979-06-05 GB GB7919628A patent/GB2022115B/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE2922296B2 (en) | 1980-09-04 |
| DE2922296A1 (en) | 1979-12-06 |
| JPS5634228B2 (en) | 1981-08-08 |
| GB2022115B (en) | 1982-11-10 |
| GB2022115A (en) | 1979-12-12 |
| DE2922296C3 (en) | 1981-05-21 |
| JPS54159459A (en) | 1979-12-17 |
| FR2428059B1 (en) | 1985-02-01 |
| FR2428059A1 (en) | 1980-01-04 |
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