AU682197B2 - Single-component polysiloxane compounds - Google Patents
Single-component polysiloxane compounds Download PDFInfo
- Publication number
- AU682197B2 AU682197B2 AU71572/94A AU7157294A AU682197B2 AU 682197 B2 AU682197 B2 AU 682197B2 AU 71572/94 A AU71572/94 A AU 71572/94A AU 7157294 A AU7157294 A AU 7157294A AU 682197 B2 AU682197 B2 AU 682197B2
- Authority
- AU
- Australia
- Prior art keywords
- groups
- polyorganosiloxane
- group
- composition according
- adhesion promoter
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Ceased
Links
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
- C08K5/5406—Silicon-containing compounds containing elements other than oxygen or nitrogen
-
- 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
- C08G77/14—Polysiloxanes containing silicon bound to oxygen-containing groups
- C08G77/16—Polysiloxanes containing silicon bound to oxygen-containing groups to hydroxyl 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
- C08G77/04—Polysiloxanes
- C08G77/14—Polysiloxanes containing silicon bound to oxygen-containing groups
- C08G77/18—Polysiloxanes containing silicon bound to oxygen-containing groups to alkoxy or aryloxy 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
- C08G77/04—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
- C08G77/04—Polysiloxanes
- C08G77/22—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen
- C08G77/24—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen halogen-containing 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
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Description
r Our Ref: 519459 P/00/011 Regulation 3:2
AUSTRALIA
Patents Act 1990
ORIGINAL
COMPLETE SPECIFICATION STANDARD PATENT 0 Applicant(s): Bayer Aktiengesellschaft D-51368 LEVERKUSEN
GERMANY
0* 0 0* 0 0 0 Address for Service: DAVIES COLLISON CAVE Patent Trade Mark Attorneys Level 10, 10 Barrack Street SYDNEY NSW 2000 Single-component polysiloxane compounds Invention Title: The following statement is a full description of this invention, including the best method of performing it known to me:- 5020 Single-component polysiloxane compounds The invention relates to single-component silicone systems, hereinafter identified as 1K-RTV compositions, which can be stored with the exclusion of moisture and which cure at room temperature under the effect of moisture and thereby release alcohols as reaction products.
This type of composition can be prepared from polyorgano-siloxanes with reactive terminal groups, silane cross-linking agents and optional fillers by using condensation catalysts. According to the prior art, organic titanium compounds are suitable as catalysts. Polysiloxane compounds which contain titanium compounds as condensation catalysts are known. A few examples only are mentioned here as being representative of those which are prepared using this type of titanium catalyst and alkoxysilane cross-linking agents of the general formula RSi(OR') 3 US 3,334,067, US 3,294,739, DE-A 3 125 881, DE-A 3 512 337, US 3,499,859 and US 4,438,039.
A prerequisite for the successful use of these 1K-RTV compositions, e.g. as sealing compounds, is good and long-lasting adhesion to the substrate. Therefore the broadest possible adhesion spectrum is desirable for the compositions as this opens up a wide range of applications.
i To improve the adhesive properties of 1K-RTV compounds, adhesion promoters 20 are generally added to the pastes, these preferably being organo-functional silanes 0 of the type (R'O) 3 .,R"nSi-X, wherein X represents any organic group, which is substituted in any position by a functional group such as, for example, an amino, cyano, mercapto, glycidyloxy or methacryloxy group.
*l There are numerous patents which describe the use of such compounds in alkoxy- 25 hardening, titanium catalyzed polysiloxane compounds. For instance, DOS 2 063
S
630 describes adhesives which contain carboxyl groups, such as, for instance, the compound (CH 3
O)
3 Si(CH) 3
S(CH
2 2 COOH. US 4, 460,739, for instance, describes Le A 29 932-FC 1 maleamidylpropyltriethoxy-silane and GB 2 079 745A describes 1,3-bistrimethoxy-silylpropyl-isocyanurate. GB 2 137 217A describes, inter alia, acyloxy, acryloxy, cyano, isocyanato, amino and epoxy functional alkoxysilanes as adhesion promoters. Mercaptosilanes are described in EP-A 345 645 and epoxyalkoxysilanes are described in EP-A 175 134. Combinations of functional silanes such as epoxysilanes and aminotrialkoxysilanes (EP-A 221 644) are also described.
These known adhesion promoters, however, have a number of disadvantages in practice. The adhesion promoting effect of silanes is sometimes restricted to only a few substrates and frequently, after storage of fully cured test bodies in water, a loss of adhesion is observed. Furthermore, cross-linking distortions and discoloration phenomena occur, especially in titanium-catalyzed 1K-RTV compositions, which are suspected to be due to reactions between the titanium catalysts and the adhesion promoters. Also, the non-cured compositions often have short shelf lives.
Therefore it is the object of the invention to find suitable adhesion promoters which avoid the disadvantages mentioned above and which produce good adhesion of 1K-RTV compounds.
Unexpectedly, it was found that particularly suitable adhesion promoters for the 20 polysiloxane compositions according to the invention are organo-functional alkoxysilanes of the general formula (R'O) 3 in which the functional group X is a halogen atom, especially chlorine, a hydroxyl group or an aminoaryl group, especially an aminophenyl group. Examples of such compounds are 3-chloro-propyltriethoxysilane, 3-chloropropyldimethoxymethylsilane, 3- 25 hydroxypropyltriethoxysilane and 3-(N-phenylamino)-propyltriethoxysilane.
The 1K-RTV compositions produced with the aid of the adhesion promoters according to the invention have a surprisingly wide adhesion spectrum, the cured product has good mechanical properties, full curing takes place rapidly and Le A 29 932-FC 2
I
C
a
S.
a p a op p 4.
p *5 S
C
Sr without distortion, there is no tendency to discolor and the shelf lives are very long.
The invention provides a polyorganosiloxane composition, which cures at ambient temperature under the effect of water or moisture to give an elastomer, and which can be stored with the exclusion of water, prepared with the exclusion of water by mixing a) a polyorganosiloxane with reactive terminal groups and having a viscosity of 1.0 to 1000 Pa.s at b) optionally polyorganosiloxanes with non-reactive terminal groups, c) a silane cross-linking agent of the formula R'4,Si(OR 2 wherein R' and R 2 0 each independently is a mono-valent optionally substituted hydrocarbon group with 2-8 carbon atoms and n is 2, 3 or 4, d) a titanium compound as a condensation catalyst, e) optionally a filler, f) an adhesion promoter of the formula 5 (R0) 3
.,R
4 ,S i-(CH 2
)-X
wherein
R
3 and R 4 each independently is a CI-C20 alkyl or alkoxyalkyl group, X is a halogen atom, an aminoaryl group optionally substituted on the aromatic moiety, Le A 29 932-FC 3 or a hydroxyl group, or a C,-C 20 alkoxyalkyl group which is substituted at one or more carbon atoms at any position by one or more hydroxyl groups, n is 0, 1 or 2, and z is from 1 to and g) optionally other additives and auxiliary agents.
In the preferred embodiment of the present invention the polysiloxane composition which hardens at ambient temperature under the effect of water or moisture and which are obtainable by mixing a) 100 parts by wt. of polyorganosiloxanes with reactive terminal groups, b) 0 to 50 parts by wt. of polyorganosiloxanes with non-reactive terminal groups, c) 0 to 20, preferably 5 to 20 parts by wt. of alkoxysilane cross-linking agents, soe d) 0.01 to 2 parts by wt. of organic titanium compounds as condensation catalysts,
•O
e) 10 to 120 parts by wt. of fillers, Soo: 99:0 f) adhesion promoters according to the invention, and 0* g) optionally, other additives and auxiliary agents, such as, e.g. stabilizers, 2 0 dyes and fungicides, in amounts of up to 5 parts by wt.
Soo* Le A 29 932-FC 4 L I Polydimethylsiloxanes can be used as polydiorganosiloxanes with reactive terminal groups wherein the methyl groups can be partly replaced by vinyl, phenyl, C 2 Cs-alkyl or haloalkyl groups. The polydimethylsiloxanes should be essentially linear. Small proportions of branching organosiloxy units may, however, be present. The viscosity of the polymers is preferably between 1.0 and 1000 Pa.s, preferably less than 100 Pa.s. Suitable reactive terminal groups are trialkoxysiloxy or dialkoxyalkylsiloxy groups, wherein the alkyl group may optionally carry, at any position, halogen atoms or amino, aryl, alkyl or hydioxyl groups, or any other functional groups. In the latter case, diethoxymethylsiloxy, diethoxyvinylsiloxy, dimethoxymethylsiloxy, dimethoxy-3-chloropropylsiloxy (-OSi(OCH 3 )2[(CH 2 )Cl]) or dimethoxy-3-(N-phenylaminopropyl)-siloxy (-OSi(OCH 3 2
[(CH
2 3 NHPh]) groups are preferred. In a preferred embodiment of the present invention the polyorganosiloxane a) preferably carries at least one of hydroxydimethyl, methyldimethoxy, vinyldiethoxy, triethoxysiloxy and 3-chloropropyldimethoxysiloxy terminal groups.
In another embodiment of the present invention wherein the polyorganosiloxane a) preferably carries at least one of hydroxydimethyl, methyldimethoxy, vinyldiethoxy, triethoxysiloxy and 3-chloropropyl-dimethoxysiloxy terminal groups, the adhesion promoter is present in from about 0.01 to 10 wt.% with 20 respect to the amount of polyorganosiloxane and the alkoxysilane cross-linking agent c) comprises a partial hydrolyzate of methyltrimethoxysilane, vinyltriethoxysilane, methyltriethoxysilane or tetraethoxysilane, methyltriethoxysilane or tetraethoxysilane and the number of silicon atoms in the i polyorganosiloxane a) and b) is from 2 to 12.
25 Suitable polyorganosiloxanes with non-reactive terminal groups are all silicone plasticizers known from the prior art. Polydimethylsiloxanes with trimethylsiloxy terminal groups and a viscosity c 0.1 5 Pas are preferably used as component b).
Le A 29 932-FC 5 Alkoxysilanes are suitable as silane cross-linking agents Alkoxysilanes have the general formula R', 4 Si(OR 2 wherein R' and R 2 each independently are a monovalent optionally substituted hydrocarbon groups with 2-8 carbon atoms, and n is 2, 3 or 4. Preferred silane cross-linking agents are alkoxysilanes such as tetraethoxysilane, methyltrimethoxysilane, methyltriethoxysilane or vinyltriethoxysilait. or partial hydrolyzates of such alkoxysilanes.
Any conventional compounds which are partly known from the cited literature are used as organic titanium catalysts such as tetraalkyl titanates, e.g. Ti(OC 2
H
5 4 Ti[OCH(CH) 4 Ti[O(n-C 4
H
9 )1 4 Ti[OCH 2
CH(CH
3 2 4 Ti[OCHCH(C 2
H)-C
4
H
9 4 and complexes of titanium with various chelating agents such as, e.g. f-dicarbonyl compounds such as ethyl acetoacetate or acetylacetone: ethyl diisobutyldiacetoacetate titanate, diisopropyl-titaniumdiacetylaceto titanate, ethyl propane- 1,2-dioxodliacetoacetate titanate, ethyl propane- 1,3-dioxodiacetoacetate titanate or ethyl propane- 1,2-dioxoacetoacetate-triethylcitrate titanate. Tetraisobutyl titanate, V ethyl propane-1,2-dioxod i aceto-acetate titanate, ethyl propane-1,2- .dioxoacetoacetate-triethylcitrate titanate and ethyl diisobutyl-bis-acetoacetate titanate are particularly suitable.
Suitable fillers e) which can be used are reinforcing fillers such as pyrogenic or precipitated silicas and carbon black or weak or non-reinforcing mineral materials S 20 with a carbonate, silicate or oxide composition. The filler surface may be pretreated. Silanized pyrogenic silicas and milled natural chalk or precipitated chalk coated with stearic acid are particularly preferred.
The adhesion promoters f) according to the invention have the following general structure:
(R'O)
3 .,R"Si-(CH 2 )z-X wherein Le A 29 932-FC 6 p i LU "V A represent identical or different linear or branched C,-C 2 0 alkyl groups or alkoxyalkyl groups, X represents a halogen atom, or an aminoaryl group, wherein the aromatic portion may optionally carry C,-
C
20 alkyl groups or alkoxyalkyl groups, halogen atoms or other functional groups on one or more carbon atoms at any position, or a hydrcxyl group or a CI-C 2 0 alkoxyalkyl group which is substituted, at one or more carbon atoms in any position, by one or more hydroxyl groups, n is 0, 1 or 2 and 4 Sz is 1 to 20, particularly preferably to 8, in particular 3.
3-Chloropropyltriethoxysilane, 3-chloropropyltrimethoxy-silane, 3-chloropropyldiethyoxymethyl silane, 2-chloroethyl-triethoxysilane, 3-(N-phenylamino)-propyltrimethoxysilane, 3-(N-(4-methylphenyl)-amino)-propyltriethyoxysilane, 3-hydroxy- 15 propyltriethoxysilane, 3-hydroxypropyltrimethoxysilane and 3-(2-hydroxyethoxy)- :*propyltriethoxysilane are particularly suitable.
The adhesion promoters according to the invention are used in amounts of 0.01 to preferably 0.1 to 6 with respect to the amount of polyorganosiloxane (component a).
The compositions according to the invention, as is usual with 1K-RTV compositions, may be prepared in planetary mixers, butterfly mixers, dissolvers, continuously operating mixing screws or other equipment suitable for preparing pastes. The compositions must be protected from atmospheric moisture during Le A 29 932-FC 7 preparation and storage. Any sequence may be used 1 or mixing the individual compon'ents.
The invention is explained in more detail by the. following examples.
Le A 29 932-FC-8 8 Examples 1 to 7 55.0 parts by weight of a polydimethylsiloxane with -OSi(OCH 3 2
(CH
3 terminal groups, which had a viscosity of 50 Pa.s at 25 0 C, were mixed with 29.0 parts by wt. of a polydimethylsiloxane with -OSi(CH 3 3 terminal groups (viscosity. 0.1 Pa.s at 25C) and 2.5 parts by wt. of methyltrimethoxysilane. Then 9.5 parts by wt. of a hydrophobic, pyrogenic silica were incorporated. Finally the titanium catalyst and the corresponding adhesion promoter were added (see Table 1).
To test the mechanical data, 2 mm thick sheets were applied to a smooth, plane base and tested after curing for 14 days at 25 0 C and 50% relative humidity in accordance with DIN 53504 (standard test piece). In addition, the Shore A hardness of the cured elastomers was determined after 21 days in accordance with DIN 53505. The skin-forming time of the compounds is determined, the time which elapses until a skin forms on the surface of the sample layer. The adhesion is determined by applying the 1K-RTV compositions in the shape of a bead with the approximate dimensions 50x50x10 mm to test plates of various substrates and then, after a curing time of 7 days, testing the adhesion to the corresponding substrate by means of a powerful tug on the cured material. A. .r passing this test, the test specimen are stored for a further 7 days in water at room temperature and subjected to an adhesion test again.
20 Example 8 55.0 parts by weight of a polydimethylsiloxane with -OSi(OCH 3 2
[(CH
2 3
CI])
terminal groups, which had a viscosity of 80 Pa.s at 25 0 C, were mixed with 29.0 parts by weight of a polydimethylsiloxane with -OSi(CH3) 3 terminal groups (viscosity 1.0 Pa.s at 25 0 C) and 2.5 parts by weight of methyltrimethoxysilane in a 25 planetary mixer. Then 9.5 parts by weight of a hydrophobic, pyrogenic silica were incorporated. Finally, the titanium catalyst and adhesion promoter as cited in Table I were added.
Le A 29 932-FC 9'- Examples 9 to 35.0 parts by weight of a polydimethylsiloyane with -OSi(CH 3 XO0H terminal groups, which had a viscosity of 80 Pa.s at 250C were mixed with 22.0 parts by weight of a polydimethylsiloxane with -OSi(CH 3 terminal groups (viscQsity 0.01 Pa.s at 2500) and with 30.0 parts by weight of a chalk filler treated with stearic acid. Then the titanium catalyst (see Table 2) was incorporated. The batch was completed by incorporating 2.5 parts by weight of methyltrimethoxysilane and parts by weight of a hydrophilic, pyrogenic silica and the amount of adhesion promoter given in Table 2.
S.
S*
S.
5
SS
S S S. S
S
S.
S
555 S S S
S
S
S. S
S
Le A 29-932-FC 10 Table I Example No. 1* 2 3 4* 5 6 7 8 Ti catalyst A A A B B B C A parts by weight 1.0 1,0 1.0 0.9 0.9 0.9 1.0 Adhesion promoter D E D E F D parts by weight 1.0 1.0 1.0 1.0 0.3 Skin-forming time 10 10 12 5 15 12 17 Shore Ahardness 19 21 20 16 19 18 20 19 after 21 days DIN 53504 standard test piece Tear strength (N/mm 2 1.56 1.60 1.78 1.75 1.70 1.68 1.50 1.77 Elongation 541 482 598 586 536 521 520 643 E-modulus (N/mm 2 0.36 0.35 0.39 0.31 0.35 0.32 0.38 10.35 Adhesion 2 2 Glass 2 2 2 1 2 2 2 2 Tiles 2 2 2 1 2 2 2 2 Aluminum 0 2 2 0 2 2 2 VA steel 2 2 Copper 0 2 2 0 2 2 2 2 PVC 0 2 2 0 2 2 2 2 Plexiglass 1 2 2 0 2 2 2 2 Macrolon 0 2 2 1 2 2 2 2 0* 0*
S
S
*5 S *5 Comparison example A ethyl propane-i ,2-dioxodiacetoacetate titanate B tetraisobutyl titanate C ethyl diisovutyl-bis-acetoacetate titanate 30 D 3-chloropropyltriethoxysilane E 3-chloropropyttriethoxysilane F 3-(N-phenylamino)-propyltrimethoxysilane Adhesion: 0 no adhesion after curing for 7 days I= adhesion after curing for 7 days 2 =adhesion after curing for 7 days followed by 7 days in water at RT Le A29 9327_M -11 Example No. 9* 10 It* 12 13 14* Ti catalyst C C A A A G G parts by weight 1.0 1.0 1.0 1.0 1.0 1.5. Adhesion promoter F D C .D parts by weight 0.5 1.0 0.5 Sin-forming time 10 12 11 9 11 minutes Shore A hardness 27 29 28 30 28 27 29 after 21 days DIN 53504 standard test piece Tear strength (N/mmn 2 1.43 1.46 1.50 1.49 1.51 1.39 1.43 Elongation 424 450 463 475 465 421 420 E-modulus (N/mm 2 10.46 0.45 0.45 10.44 0.43 10.46 0.45 Adhesion/caterpillar track test Glass 2 2 2 2 2 2 2 Tiles 2 2 2 2 2 2 2 Aluminum 2 2 1 2 2 1 2
V
4 A steel 2 2 0 2 1 Copper 0 2 1 2 2 0 2 PVC 0 2 0 2 2 0 2 Plexiglass 0 2 0 2 2 0 2 Macrolon 0 21 2 2 0 2 *Comparison example A ethyl propane- 1,2-dioxodiacetoacetate titanate C ethyl diisobutyl-bis-acetoacetate titanate D chloropropyl triethoxysi lane 30 F =3-(N-phenylamino)-propyltrimethoxysi lane G =ethyl propane- 1,2-dioxo-acetoacetate-tri ethy 1-citrate titanate Adhesion: 0 no adhesion after curing for 7 days I=adhesion after curing for 7 days 2 =adhesion after curing for 7 days followed by 7 days in water at RT 4
*S~SSS
S S S S
S
S
S S
S.
Le A 29 932-FC 12 It is understood that the specification and examples are illustrative but not limitative, of the present invention and that other embodiments within the spirit and scope of the invention will suggest themselves to those skilled in the art.
0 0 .000 0 0000 00 0 0 00 Le A 29 932-FC 13
Claims (9)
1. A polyorganosiloxane composition, which cures at ambient temperature under the effect of water or moisture to give an elastomer, and which can be stored with the exclusion of water, prepared with the exclusion of water by mixing a) a polyorganosiloxane with reactive terminal groups and having a viscosity of 1.0 to 1000 Pa.s at b) optionally polyorganosiloxanes with non-reactive terminal groups, c) a silane cross-linking agent of the formula R'4.,Si(OR 2 wherein R' and R 2 each independently is a mono-valent optionally substituted 10 hydrocarbon group with 2-8 carbon atoms and n is 2, 3 or 4, d) a titanium compound as a condensation catalyst, e) optionally a filler, f) an adhesion promoter of the formula Si-(CH2) -X wherein 0. R 3 and R 4 each independently is a CI-C2 alkyl or alkoxyalkyl group, X is a halogen atom, an aminoaryl group optionally substituted on the aromatic moiety, Le A 29 932-FC 14 or a hydroxyl group, or a C 1 alkoxyalkyl group which is substituted at one or more carbon atoms at any position by one or more hydroxyl groups, n is 0, 1 or 2, and z is from 1 to and g) optionally other additives and auxiliary agents.
2. A composition according to Claim 1, wherein the adhesion promoter f) comprises at least one of 3-chloropropyltriethoxysilane and 3-chloropropyl- trimethoxysilane.
3. A composition according to Claim 1, wherein the adhesion promoter f) comprises at least one of 3-(N-phenylamino)-propyltrimethoxysilane and 3- (N-(4-methylphenyl)-amino)-propyltriethoxysilane.
4. A composition according to Claim 1, wherein the promoter f) comprises 3- hydroxypropyltrimethoxysilane. 15 5. A composition according to Claim 1, wherein the adhesion promoter is present in from about 0.01 to 10 wt.% with respect to the amount of poly- organosiloxane
6. A composition according to Claim 1, wherein the silane cross-linking agent c) comprises at least one of methyltrimethoxysilane, vinyltriethoxysilane, 20 methyltriethoxysilane and tetraethoxysilane. S* Le A 29 932-FC 15
7. A composition according to Claim 1, wherein the silane cross-linking agent c) comprises a partial hydrolyzate of methyltrimethoxysilane, vinyl- triethoxysilane methyltriethoxysilane or tetraethoxysilane, and the number of silicon atom in the polyorganosiloxane a) and b) is from 2 to 12.
8. A composition according to Claim 1, wherein the polyorganosiloxane a) carries at least one of hydroxydimethyl, methyldimethoxy, vinyldiethoxy, triethoxysiloxy and 3-chloropropyl-dimethoxysiloxy terminal groups.
9. A composition according to Claim 1, wherein the polyorganosiloxane a) carries at least one of hydroxydimethyl, methyldimethoxy, vinyldiethoxy, triethoxysiloxy and 3-chloropropyl-dimethoxysiloxy terminal groups, the adhesion promoter is present in from about 0.01 to 10 wt.% with respect to the amount of polyorganosiloxane and the alkoxysilane cross-linking agent c) comprises methyltrimethoxysilane, vinyltriethoxysilane, methyltriethoxysilane, or tetraethoxysilane, and the number of silicon atoms in the polyorganosiloxane a) and b) is from 2 to 12. In a single-component silicone composition, prepared with the exclusion of water, comprising a silicone, a titanium compound, an alkoxysilane cross- linking agent and an adhesion promoter, the improvement wherein such adhesion promoter comprises a compound of the formula 20 (R 3 O) 3 .,R'Si-(CH 2 wherein R 3 and R 4 each independently is a C,-C2o alkyl or alkoxyalkyl group, X is a halogen atom, Le A 29 932-FC 16 I or a hydroxyl group, or a C 1 -C20 alkoxyalkyl group which is substituted at one or more carbon atoms at any position by one or more hydroxyl groups, n is 0, 1or 2,and z is an integer from I to
11. A polyorganosiloxane composition subscantially as hereinbefore described with reference to the examples. DATED this 19th day of October, 1994. BAYER AKTIENGESELLSCHAFT By Its Patent Attorneys DAVIES COLLISON CAVE see* o00 0 0 sees see s Le A 29 932-FC 17 4 A 1* Sin g1e-component- poly si loxane composition A bs tr ac t Compounds of the general formula (R 3 O) 30 R 4 *Si-.(CH 2 wherein R" represent identical or different linear or branched C,-C 2 alkyl groups or alkoxyalkyl groups, X represents a halogen atom, an aminoaryl group, wherein the aromatic group can optionally carry, on one or more carbon atoms at any position, alkyl groups or alkoxyalkyl groups, halogen atoms or other functional groups, or a hydroxyl group or a alkoxyalkyl group, which is substituted at one or more carbon atoms at any position by one or more hydroxyl groups, n 0, 1 or 2 and z an integer between I and 20 are suitable as adhesion promoters in IK-RTV compounds which have titanium compounds as condensation catalysts. 9G C C S we C OS S e.w Ge C B S CGS C C C. C C.. C S CC.. C C 0O C S *9*G C 0*SSCS o a SC C 06 C. C Le A 29 932-F
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE4329263 | 1993-08-31 | ||
| DE4329263A DE4329263A1 (en) | 1993-08-31 | 1993-08-31 | One-component polysiloxane compositions |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU7157294A AU7157294A (en) | 1995-03-16 |
| AU682197B2 true AU682197B2 (en) | 1997-09-25 |
Family
ID=6496424
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU71572/94A Ceased AU682197B2 (en) | 1993-08-31 | 1994-08-30 | Single-component polysiloxane compounds |
Country Status (7)
| Country | Link |
|---|---|
| EP (2) | EP0640657A2 (en) |
| JP (1) | JPH0797518A (en) |
| KR (1) | KR950005909A (en) |
| AU (1) | AU682197B2 (en) |
| DE (1) | DE4329263A1 (en) |
| HU (1) | HU214044B (en) |
| NZ (1) | NZ264321A (en) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3712029B2 (en) * | 1998-01-29 | 2005-11-02 | 信越化学工業株式会社 | Method for producing room temperature curable organopolysiloxane composition |
| JP4249306B2 (en) * | 1998-11-16 | 2009-04-02 | Ｎｓｋワーナー株式会社 | Wet friction material |
| JP4530177B2 (en) * | 2006-12-11 | 2010-08-25 | 信越化学工業株式会社 | Room temperature curable organopolysiloxane composition |
| JP5839463B2 (en) * | 2011-12-16 | 2016-01-06 | モメンティブ・パフォーマンス・マテリアルズ・ジャパン合同会社 | Room temperature curable polyorganosiloxane composition |
| DE202016106073U1 (en) | 2016-10-28 | 2016-11-07 | Wenko-Wenselaar Gmbh & Co. Kg | Mounting system with integrated reservoir clutch for material connection |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5300611A (en) * | 1991-10-21 | 1994-04-05 | Shin-Etsu Chemical Co., Ltd. | Room temperature curable organopolysiloxane compositions |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4315970A (en) * | 1980-02-11 | 1982-02-16 | Dow Corning Corporation | Adhesion of metals to solid substrates |
| US4460739A (en) * | 1983-07-01 | 1984-07-17 | General Electric Company | Composition for promoting adhesion of curable silicones to substrates |
| JPS63297458A (en) * | 1987-05-29 | 1988-12-05 | Central Glass Co Ltd | Silicone polymer based vibration damping material |
| JP2560557B2 (en) * | 1991-02-26 | 1996-12-04 | 信越化学工業株式会社 | Adhesive silicone rubber composition |
-
1993
- 1993-08-31 DE DE4329263A patent/DE4329263A1/en not_active Withdrawn
-
1994
- 1994-08-18 EP EP94112899A patent/EP0640657A2/en not_active Withdrawn
- 1994-08-26 NZ NZ264321A patent/NZ264321A/en unknown
- 1994-08-30 EP EP94113491A patent/EP0640659A3/en not_active Withdrawn
- 1994-08-30 JP JP6227378A patent/JPH0797518A/en active Pending
- 1994-08-30 HU HU9402496A patent/HU214044B/en not_active IP Right Cessation
- 1994-08-30 KR KR1019940021521A patent/KR950005909A/en active IP Right Grant
- 1994-08-30 AU AU71572/94A patent/AU682197B2/en not_active Ceased
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5300611A (en) * | 1991-10-21 | 1994-04-05 | Shin-Etsu Chemical Co., Ltd. | Room temperature curable organopolysiloxane compositions |
Also Published As
| Publication number | Publication date |
|---|---|
| AU7157294A (en) | 1995-03-16 |
| HU214044B (en) | 1997-12-29 |
| KR950005909A (en) | 1995-03-20 |
| NZ264321A (en) | 1997-01-29 |
| HUT70862A (en) | 1995-11-28 |
| DE4329263A1 (en) | 1995-03-02 |
| EP0640657A2 (en) | 1995-03-01 |
| EP0640659A3 (en) | 1996-07-17 |
| JPH0797518A (en) | 1995-04-11 |
| HU9402496D0 (en) | 1994-11-28 |
| EP0640659A2 (en) | 1995-03-01 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2007238820A (en) | Organopolysiloxane hydrophilic composition, its coating film, its hardened material, and its application | |
| EP0457616B1 (en) | Flame retardant coating compositions and coated articles | |
| JPS6314750B2 (en) | ||
| EP0096424B1 (en) | Room temperature vulcanizable polyorganosiloxane compositions which are paintable following curing | |
| JPH0627162B2 (en) | Photocurable organopolysiloxane composition | |
| US6254811B1 (en) | Organopolysilozane compositions crosslinkable with elimination of alcohols to give elastomer | |
| JPWO2018186167A1 (en) | Room temperature curable organopolysiloxane composition and substrate | |
| US10316149B2 (en) | Crosslinkable organopolysiloxane compositions | |
| US6515094B2 (en) | Silicone amino-epoxy cross-linking system | |
| JPH09506667A (en) | RTV silicone compositions using aminohydrocarbyl substituted ketoximinosilane | |
| KR20170106404A (en) | The room temperature curable organopolysiloxane composition | |
| US5705587A (en) | Room-temperature-curable silicone elastomer composition | |
| US6166121A (en) | Curable organopolysiloxane composition | |
| EP0575863B1 (en) | Modulus controllable room-temperature-curable silicone elastomer composition | |
| AU616947B2 (en) | organopolysiloxane compositions which crosslink at a room temperature to form paint-compatible to overcoatable elastomers | |
| US5567752A (en) | Silicon- and nitrogen- containing adhesion promotors and compositions containing them | |
| US5530082A (en) | Single-component polysiloxane compounds | |
| JPH03203960A (en) | Room temperature curable organopolysiloxane composition | |
| US4358558A (en) | Room temperature curable polyorganosiloxane compositions | |
| AU682197B2 (en) | Single-component polysiloxane compounds | |
| JPH1067935A (en) | Curable organopolysiloxane composition | |
| JP2762206B2 (en) | Curable organopolysiloxane composition and cured product thereof | |
| US5639823A (en) | One-package, room-temperature-vulcanizable, silicone elastomer composition | |
| US6296944B1 (en) | Curable silicone adhesive compositions | |
| JP5106914B2 (en) | Room temperature curable organopolysiloxane composition |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MK14 | Patent ceased section 143(a) (annual fees not paid) or expired |