AUTO-ADHERING ONE-COMPONENT RTV SILICONE SEALANT COMPOSITION UTILIZING GLYCIDOXYALKYL SUBSTITUTED ALKOXY-OXIME SILANE AS AN ADHESION PROMOTER

Abstract: An auto-adhering one-component room temperature vulcanizable silicone sealant utilizes a glycidoxyalkyl substituted mixed alkoxy-oxime silane as an adhesion promoter. The sealant bonds to a variety of substrates including glass, metal, ceramics; does not require a primer to be applied to the substrate; has a low odor and is non-corrosive to ferrous substrates. The sealant is useful as a formed-in-place gasket material as for example, an internal combustion engine and has good oil resistance for an RTV silicone gasketing material.

Description: Title: AUTO-ADHERING ONE-COMPONENT RTV SILICONE, SEALANT COMPOSITION UTILIZING GLYCTDOXYALKYL SUBSTITUTED ALKOXY-OXIME SILANE AS AN ADHESION PROMOTER TECHNICAL FIELP ' The present invention relates to a glycidoxy- alkyl substituted alkoxy-oxime silane as an adhesion promoter, which can be used in a silicone sealant. BACKGROUND ART Heretofore, various silicone adhesive sealants applied to an iron containing substrate had a disadvan¬ tage of initially being corrosive. These same sealants also required a silicone resin primer to be initially applied to the substrate before they could be coated thereon. They also tended to have a disagreeable odor and generally did not have good oil resistance, especially at elevated temperatures. U.S. Patent No. 3,189,576 to Sweet relates- to oxi e curatives and to new organosilicone intermediates. U.S. Patent No. 4,323,489 as well as D.S.; Patent No. 3,962,161^ both to Beers, generally relate to oxime curaftle room temperature vulcanizates. More specifically, the '489 patent relates to a vulcanizable silicone rubber composition with very low modulus containing a silanol end-stopped diorganopolysiloxane, a difunctional acetamide coupler as a chain extender and a minor amount of a compound containing an oxime functionality thereon as a trifunctional crosslinker. U.S. Patent No. 4,356,116 to Beers relates to a low volatile room te peraure vulcanizable silicone rubber composition, containing various components including a silanol polymer, a crosslinking agent, and a filler. U.S. Patent No. 3,517,001 to Berger relates to adhesion promoter compositions. U.S. Patent No. 4,100,129 to Beers also relates to adhesion promoter compositions curable in the presence of moisture. U.S. Patent No. 4,395,526 to White et al relates to a stable, substantially acid-free, one-componen t curable polyalk oxy-te r inat ed organosiloxane composition having' a condensation catalyst, such as a tin compound. The material in this patent also serves as an adhesion promoter. Specific patents relating to acetoxy curing room temperature vulcanizable silicones include Ceyzeriat, U.S. Patent No. 3,133,891, Brunner, 3,035,016, and Beers, 3,382,205. More specifically, the Beers' patent relates to orσanopolysiloxane composition comprising a mixture of organetriacyloxysilane and a base mixture containing organosiloxan« having chemically combined organs iloxy units. U.S. Patent No. 3,541,044 to Eeers relates to a substantially anhydrous organopolysiloxane composition curable to the elastomeric state upon exposure to moisture. Another patent by Beers, namely U.S. Patent No. 3,837,878 relates to a two-component room tem e-α uic vulcanizable silicone rubber composition -" suitable for molding applications whereas Patent No. 3,837,878 also to Beers relates to a process for treating silicone " fillers. U.S. Patent No. 3,776,933 to Toporcerer relates to chain extenders with regard to RTV systems. The above patents do not teach or suggest an adhesion promoter composition or compound containing a glycidoxyalkyl substituted mixed alkoxy-oxime silane or such a silane which has low odor, is non-corrosive to iron substrates.,and has goo d adhesion as well as good oil resistance. DISCLOSURE OF INVENTION It is therefore an aspect of the present invention to provide an adhesion promoter comprising a glycidoxyalkyl substituted mixed alkoxy-oxime silane- type compound. It is a yet further aspect of the present invention to provide an adhesion promoter, as above, which is utilized in an auto-adhering one-coirroonent RTV silicone sealant; and which sealant composition is non-corrosive to ferrous and alunir- m substrates, has a low odor and eliminates the need for a primer coat to obtain good adhesion. It is another aspect of the present invention to provide an auto-adhering one-component RTV silicone sealant, as above, which has good oil resistance. It is another aspect of the present invention to provide an auto-adhering one-component RTV silicone sealant, as above, which has good oil resistance. ._ It is yet a further aspect of the present invention to provide an auto-adhering one-component RTV silicone sealant, as above, which has good adhesion to substrates such as steel, iron, aluminum, acrylic plastics and paints, polycarbonate, polyester, ABS, glass, ceramics, brick, concrete and the like. These and other aspects of the present invention will become apparent from the following specification. The inventive adhesion promoter is a compound having the wherein R-*- is a hydrocarbyl, or a halohydrocarbyl having from 2 1 to 10 carbon atoms; S. is a divalent hydrocarbyl, or a 3 halohydrocarbyl having from 1 to 10 carbon atoms; R is a hydrocarbyl, a halohydrocarbyl, or a carboxyalkyl having 4 5 from 1 to 10 carbon atoms; m is from 0 to 3, R and R can independently be a hydrocarbyl, halohydrocarbyl or carboxyalkyl having from 1 to 10 carbon atoms; x is 0 ro 3; R is hydrocarbyl, a halohydrocarb:vl, or a carboxyalkyl having from 1 to 10 carbon atoms; p is 0 — 2; and the R groups are indepently hydrogen, hydrocarbyl, halohydrocarbyl, or carboxyalkyl having from 1 to 10 carbon atoms; and x+m÷p=3. The adhesion promoter of the present invention can be utilized in silicone sealants. When so utilized, the sealant sealant composition exhibits very good auto-adhering adhesion even on oil contaminated metal such as aluminum and steel surfaces as encounter¬ ed in the auto industry. Additionally, such composi¬ tions have excellent oil resistance properties, even at high temperatures for example, 300°F, and are particu¬ larly useful as silicone for ed-in-place gasketing. According to the concepts of the present invention an auto adhering one-component RTV silicone sealant is prepared utilizing a glycidoxyalkyl adhesion substituted mixed alkoxy-oxime silane. The adhesion- promoter can be presented by the following formula. R is a hydrocarbyl having from 1 to 10 carbon atoms. Throughout this entire specification, by the term "hy rocarbyl" it is meant that toe hydrocarbon group is an aliphatic or cycloaliphatic ^oup such as an alkyl, an alkenyl, an acetylene group or cycloalkyl, etc. with alkyl being preferred, or an aromatic group including aliphatic substituted aromatic or an aromatic substituted aliphatic. This definition of hydrocarbyl is applicable not only with regard to R 1 but also with regard to R2 through R8 groups with the exception that R3 does not contain aromatic groups. Rl can also be a halohydro¬ carbyl having from 1 to 10 carbon atoms. Generally, an alkylene group is desired with ethylene being preferred. 2 R can be a hydrocarbyl group, or a halohydrocarbyl having from 1 to 10 carbon atoms. An alkylene group is desired, preferably a 3-8 carbon alkylene group. 3 The R group can be a hydrocarbyl group, a halohydrocarbyl group or a carboxyalkyl group having from 1 to 10 carbon atoms. Desirably, an alkyl group is preferred with methyl being highly preferred. The number of "OR " groups or "m" is from 0 to 3, desirably 1 to 2 with 1 being preferred. With regard to the 4 5 substituents on the oxime group, R and R can be the same or different and include a hydrocarbyl, a halohydrocarbyl, or a carboxyalkyl, all having from 1 to 10 carbon atoms. Generally, alkyl groups are desired with methyl or ethyl being highly preferred. The number of oxime groups on the silicon atom, that is "x" is generally from 0 to 3, desirably 1 to 3, with 2 being preferred. R is a hydrocarbyl, a halohydrocarbyl, or a carboxyalkyl having from 1 to 10 carbon atoms. The number of such R groups, that is "p" can be 0 co 2, preferably 0. R can be hyαrogen, hydrocarbyl, halohydrocarbyl, or carboxyalkyl having from 1 to 10 carbon atoms with methyl being desirable, Preferrably, however, both R groups are H. Examples of specific adhesion promoters according to the present invention include the following compounds: (A) >_ / \ H. CH _ CH 2 — 0 - (CE^ - Si-(θ - CH 3 ' ) CH. N- C 2 H 5 (B) (C) 0 N li C 2 H 5 CH. (D) The adhesion promoter of the present invention having the above formulation is prepared in the manner as set forth below involving reaction of a glyciloxy silane compound with an oxime compound. The overall reaction of a glycidoxyalkyl silane compound with an oxime compound can be represented as follows: ~r m + x The oxime crosslinking units are grafted onto the glycidoxyalkyl silane by carrying out the reaction at a temperature from about 45°C. to about 150 C, preferably from about 50 C to aboit 120 C. An inert gas blanket for example nitrogen, is utilized to avoid reaction with moisture. The type of oxime compounds utilized are generally of the type set forth in formulae A and B below or mixtures thereof. As should be apparent from the - reaction set forth above, a large variety of different compounds can be made according to the present invention. In carrying out the reaction of forming the adhesion promoter, an organic tin salt catalyst is generally utilized. The amount of tin catalyst is generally from about 0.01 to about 0.5 percent by weight and preferably from about 0.02 to about 0.2 by weight based upon the total amount of said silicone sealant compound. Such tin catalysts are generally well known to the art, such as those set forth in U.S. Patent Nos. 4,356,116 and 4,395,526 hereby fully incorporated by reference. Examples of specific tin catalysts include dibutyltindilaurate, dibutyltindiacetate, tin octoate, dimethyltindibutyrate, triethyltintartrate, tin oleate, dibutyltinoxide and dimethyltin bisneodecanoate. The adhesion promoter as discussed above forms a part of " a silicone composition containing various components thereof such as a base polymer, a plasti- cizer, a thixotropic agent, and the like. Considering the base polymer, it is a silanol terminated ciorgano- polysiloxane polymer. This linear polymer may be devolatilized in a manner such as set forth in U.S. Patent No. 4,356,116 and generally has a viscosity of from about 2,000 to about 250,000 centipoise and preferably from about 10,000 to about 120,000 centipoise. The polymer has the formula HO 0 I H 1 2 where n is from about 300 to about 1,000, where R ana R can be 1 2 the same or different, where R and R is an alkyl group having from 1 to 8 carbon atoms with methyl being preferred, a cycloalkyl group having from 4 to 7 carbon atoms such as cyclohexyl, an alkenyl group having from 2 to 8 carbon atoms such as allyl with vinyl being preferred, an aryl or an alkyl substituted aryl group having from 6 to 14 carbon atoms such as phenyl, methylphenyl, or a fluoroalkyl group having from 1 to 8 carbon atoms with 3,3,3-trifluoropropyl being preferred. The amount of the linear polymer generally ranges from about 25 to about 90 percent by weight and preferably from 30 to about 60 percent by weight based upon the total weight of the low modulus RTV silicone composition. Such polymers are commercially available and are manufactured by Mobay, Union Carbide and Wacker Chemie. Generally, the silanol terminated silicone polymer also is reacted with an oxime compound having the formulation set forth in formula A wherein the oxime compound is grafted onto ' the polymer. Simple types of oxime compounds which can be utilized in the present invention is set forth in formulations A and/or B wherein on a molar basis, from 0.0 or 0.05 moles to about 0.4 moles of the formula A oxime is utilized and preferably from about 0.1 to about 0.2 moles of the formulation A oxime compound per 1 -mole of said Formula "A" and "B" compounds. Naturally, the amount of the Formula "B" compound is the difference, that is from 0.6 to 0.95 and preferably from 0.8 to 0.9 moles per 1 mole of said Formula "A" and said "B" compounds. Formula "A' Formula "B 1 R4 and R5 are as set forth above. Similar¬ ly, "x" is the same as set forth above, that is from 0 to 3 with 2 being preferred. It is to be understood that when one of the oxime types has "x" as zero, the remaining type or formula must be more than 2, 9 can be an alkyl having from 1 to 8 carbon atoms with methyl being preferred, an alkεnyl croup having from 2 to 8 carbon atoms with vinyl being preferred, a haioaikyl having from 1 to 6 carbon atoms, a triflucroalkyl having from 1 to 8 carbon atoms, or a haloaikenyl having from 2 to 8 carbon atoms. R8 can be a hydrocarbyl, a halohydrocarbyl, or a carboxyalkyl having from 1 to 10 carbon atoms. Preferably Rδ is methyl or ethyl. Generally, when an oxime compound is utilized as set ' forth in Formulas A or B wherein Α - is methyl, R5 is ethyl, R9 is methyl or vinyl and R8 is methoxy, with x being 2, an unexpected synergistic result is obtained with . regard to adhesion. An enhancement of adhesion results. The enhancement is maximized when R9 is vinyl. Once the adhesion promoter has been formed, the • amount thereof generally utilized in the overall silicone sealant composition is from about 0.5 percent to about 3 percent by weight with from about 0.8 percent to about 2 percent by weight being preferred. Preparation of an oxime type compound as set forth in Formula A is generally well known to- the art and literature, as for example U.S. Patent No. 3,189,576 which is hereby fully incorporated by reference as to the manner and method of preparing such oxime compounds. In order to insure that gellation or viscosity increases do not occur, an excess of the crosslinker containing the oxime group to the silanol in the base polymer, set forth below, is utilized at a ratio of from about 1.2 to about 4.0 with from about 2.0 to about 3.0 being preferred molar ratio of crosslinker to silanol groups. The plasticizer utilized along with the linear base polymer in the sealant composition is a devolatilized triorganosiloxy terminated diorgano- polysiloxane fluid existing in an amount of from 0 jor 1 to about 40 percent by weight and desirably from ' 5 to about 25 percent by weight based upon the total weigh t o f thesiloxanesealant composition. The plasticizer lowers , ' the durometer and - modulus of the cured rubber and lowers the viscosity of the overall system or composition. However, the viscosity of the plasticizer should not be too low inasmuch as it will tend to bleed out of the composition. Accordingly, the viscosity generally ranges from about 50 to about 100,000 centipoise and preferably from about 500 to about 10,000 centipoise. The plasticizer is a diorganopolysiloxane polymer terminated with monofunctional, triorgano siloxy end groups. The organo compounds within the repeating units are the same as Rl and R2 set forth herein above with regard to the base polymer. However, it may contain trace quantities of trifunctional onoorgano- siloxy units originating from impurities in the starting materials. The siloxy units contain an alkyl group having from 1 to 8 carbon atoms with methyl being preferred. The number of repeating units in the plasticizer is generally from about 20 to about 900. As with the linear base polymer, the plasticizer is devolatilized in accordance with any conventional manner or process, well known to the art. A specific example of devolatilization is seth forth in U.S. Patent No. 4,356,116 which is hereby fully incorporated by reference. In order to reinforce the polymer network as well as to impart non-sag properties to the system, a thixotropic agent is added to the overall composition. This agent which also adds physical strength to the system desirably is a treated or an untreated silica filler with a treated fumed silica filler being preferred. Treated or untreated silica fillers are well known to the-- art and generally any such conventional filler can be utilized. Examples cf specific silica fillers are„ set forth in U.S. Patent No. 3,637,578 whuich is hereby full incorporated by reference. Additionally, treated silica as " set forth in Lucas U r .S. Patent No. 2,538,005, Lichtenwainer U.S. Patent Nc. 3,004,859, and Smith U.S. Patent Nc. 3,635,743, all hereby full incorporated by reference, can be utilized. Typically, the silica filler has a very high surface area such as about 200 2/gram. Optionally, from about 0.1 to about 5 percent by weight and preferably from about 0.2 to about 3 percent by weight based upon the total weight of the overall system or composition of a thermal aging add¬ itive can be utilized. This optional component functions to reduce oxidation and thermal rearrangement of polymers at elevated temperatures. These antioxidants may include materials like cerium neodecanoate, rare earth octoates and iron octoates. Representative samples can also usually include thermal aging additives such as carbon black, iron oxide powder, and titanium dioxide. Naturally, other pigments can be utilized. Another optional ingredient is an inert non-reinforcing filler such as ground quartz, calcium carbonate, talc, clay, various silicate compounds and other materials well known in the art. The amount utilized is- from about 5% to about 60% by weight bases upon the total weight of the sealant composition. The sealants of the present invention containing the adhesion promoter therein exhibits numerous improved and desirous properties. For example, a silicone resin primer is no longer needed to obtain - good adhesion, but rather a silicone sealant of the present invention can be directly applied to a metallic or other surface. For example, the sealant composition of the present invention has good adhesion to various substrates such as steel, iron, aluminum, acrylic plastics and paints, polycarbonate, polyester, A3S, glass, ceramics, brick, concrete and the like. More¬ over, the silicone sealants cf the present invention have low odor characteristics as opposed to the sometime nauseating odor of prior art sealants and are generally non-corrosive with regard to iron or aluminum substrates. The silicone sealants of the present invention can be utilized as in-place gasketing sealants due to their good thermal resistance at high temperatures as for example from about 250°F ' to about 500°F and still maintain good flexibility at low temperatures, that is about 85°F. Particu l ar uses include RTV silicone adhesives,- bathtub caulking compounds, masonry joint materials, as a plastic adhesive, and the like. The silicone sealants are particularly suitable for usage in various internal combustion engine for various gasket applications such as oil pan gaskets, valve cover gaskets, water seals, intake seals, and the like. The preparation and incorporation of the aforementioned silane adhesion promoter can be accomplished according to one of two modes. In the first mode, there is a reaction product of various oxime type products and thus the exact end product or type is not known. In the second mode, a specific oxime product is produced. In the first mode of preparation from about 0.5 to 4 parts of a glycidoxyalkyl trialkoxysilane is added to the crosslinker mixture consisting of about 12 parts of the oxime curing agent set forth above and this mix¬ ture is heated at 50°C for about -20 hours in a closed container or about 4 hours at 120°C in a sealed container. The silicone sealant compound is then prepared by charging the various ingredients into a mixer under dry conditions as through the use of dry nitrogen to prevent hydrolysis cf the oxime crosslinking compound. Generally, the polymer is added first with the plas¬ ticizer. The oxime crosslinker and adhesion promoter composition is then added followed by the fumed si.lica, as well as any thermal stabilizing agent. The treated calcium carbonate filler is then added. The composition is mixed under high speed or agitation as well as under a vacuum for several minutes or even hours to remove the entrapped nitrogen bubbles. The resulting paste formed can be placed or extruded into a desirable container and the like. The invention will be better understood by reference to the following example: Example 1 Weight ____!__ 1. 10,000 cps. viscosity silanol terminated polydimethylsiloxane 40.06 2. 1000 cps tri ethylsilyl termin¬ ated polydimethylsiloxane 15.46 3. Stearic acid treated calcium carbonate 34.05 4. Polydimethylsiloxane treated fumed silica having a surface area of approximately 200mV gram 3.61 5. Iron oxide 1.40 6. Methyltris-methylethylketoximos- ilane 4.81 7. Di ethyltinbisneodecanoate 0.08 δ. Gamma-glycidoxypropyltrimethoxy- silane 0.53 This composition was prepared by charging the ingredients into the mixing can of a vertical laboratory change can mixer which had been flushed with dry nitrogen to prevent the hydrolysis of the oxime crosslinker. Ingredients (6), (7) and (8) were heated in a closed glass jar in a 50°C oven for ic hours and allowed to cool before incorporation into the sealant formula¬ tion. The ingredients were subsequently added as follows: (1), (2), (3), (4), and (5), then the mixture of (β) , (7) and (8). Then mixed at high speed under vacuum for approximately two hours and afterwards the resulting paste was transferred to a pressure Semco mixer. It was then extruded from the pressure Semco into six ounce polyethylene cartridges. It was found that the 180°F. peel adhesion of this sealant to Alclad aluminum after curing for 14 days was 8 to 10 pounds per linear inch with 100% cohesive failure versus 0 to 2 pounds per linear inch with 100% adhesive failure for a sealant without (8) and also for a sealant with (8) but excluding in the preparation of said sealant the step of heating at 50°C for 16 hours the mixture of (6), (7) and (8). In the second mode of preparation a glycidoxyalkyl trialkoxysilane is heated with a sufficient amount of a ketoxime compound such as methyl ethylketoxime to cause a partial substitution of the ketoxime on the silicon atom by displacing the alkoxy moiety. The sealant is prepared as described for the first mode of preparation. This mode of preparation can be better understood by reference to the following examples. —,-*._-.._.•_-. __ 47.2δg (0.2 mole) of gamma-glycidcxypropy tri- methoxv silane land 15.18 (0.22 mole of methvl ethvi ketoxim . were charged to a glass f ask and heated u der nitrogen at 120 C ,C for 16 hours. The resulting analysis by gas chromatograph indicated partial substitution of the ethcxy moieties by methyl ehty kctcximo moieties en the silicon atom. Mono, ci, and tris bεtit tec species were indicated. 1 9 Example 3 Weight -Λ 1. 10,000 cps. viscosity silanol terminated polydimethylsiloxane 40.06 2. 1000 cps tri ethylsilyl termin¬ ated ' polydimethylsiloxane 15.46 3. Stearic acid treated calcium carbonate 34.05 4. Polydimethylsiloxane treated fumed silica having a surface area of approximately 200m / gram 3.61 5. Iron oxide 1.40 6. Methyltris-methylethylketoxi os- ilane 4.81 7. Dimethyltinbisneodecanoate 0.08 8. The material of Example 2 0.53 This composition was prepared as in Example 1. The ingredients were added in the order: (1), (2), (3), (4), (5), (6), (7), and (8), then mixed at high speed under vacuum for approximately two hours and afterward the resulting paste was transferred to a pressure Semco mixer and extruded into six ounce polyethylene cartridges. The peel adhesion of this sealant to Aiclad aluminum after curing for four weeks was 13 p i (lbs. per linear inch) with 100% cohesive ~aii re« While in accordance with the patent statutes, a best mode and preferred embodiment have been described in detail, the scope of the invention is not limited thereto, but rather by the scope of the attached claims.

Claims: CLAIMS What is claimed is: 1. An adhesion promoter, comprising; a compound having the formula: wherein R1 is a nydrocarbv] C . f» *_✓ » .__ __. l _5 V v* * ^ . * "I! = *~. . ~ * » _ ^-s ' i"_"» i I :o 10 carbon atoms; ?.3 is a nyc oca oyj a ca: ■ boxya lkyl ιi v * i . o * — i. uu toms : __■ s : - rT.o-. - - - _ J _ ■ < — Ά CT-\ .M~ _/ * _>& _ independently be a hydrocarbyl, halohydrocarbyl or carboxyalkyl having from 1 to 10 carbon atoms; x is 0 to 3; RP is hydrocarbyl, a halohydrocarbyl, or a carboxyalkyl naving from 1 to 10 carbon atoms; p is 0 '-— 2 and the R groups are independently hydrogen, hydrocarbyl, halohydrocarbyl, or carboxyalkyl having from 1 to 10 carbon atoms; and x÷m+p=3. 2. An adhesion promoter according to Claim 1 , wherein R1 and R2 are alkylene groups, R3, R4 and R5 are the same or different alkyl groups, the R7 groups are both hydrogen and p is 0. 3. An adhesion promoter according to Claim 2 wherein R1 is methylene, R2 is propylene and R3 is methyl. 4. An adhesion promoter according to Claim 1, wherein R4 and R5 is selected from the group consisting of methyl or ethyl. 5. An adhesion promoter according to Claim 4, wherein R4 is methyl and R5 is ethyl. 6. A silicone sealant, comprising: from about 25 to about 90 percent Dy weight based upon a total weight of the sealant of a devolatilized silanol terminated diorganosiloxane base polymer having a viscosity from about 2,000 to about 250,000 centipoises at 25°C where said organo groups can be tne same or different and is selected from tne group consisting of an alkyl having from 1 to 5 oareon atoms, a cycloalkyl having from 4 to 7 carbon atoms, an alkyl substituted aryl having from 5 to 14 carbon atoms, or a fiuoroalkyl having from 1 to 8 carbon atoms; from about 0 to 40 percent by weight based upon the total weight of said composition of a- devolatilized diorganopolysiloxane fluid plasticizer terminated with triorganosiloxy groups, said organo groups being a monovalent hydrocarbon radical as set forth above with regard to said base polymer, said plasticizer having a viscosity from about 50 to about 100,000 centipoises at 25°C; and from about 0.5 percent to about 3 percent by weight of an adhesion promoter, of Claim 1. 7. A silicone sealant according to Claim 6, including from about 1 percent to about 20 percent by weight of a thixotropic agent, wherein the viscosity of said base polymer is from about 10,000 to 120,000 centipoises, wherein the amount of said polymer ranges from about 30 percent to about 60 percent, wherein the viscosity of said plasticizer is from 500 to about 10,000 centipoises, and wherein the amount of said plasticizer ranges from about 5 percent to about 25 percent by weight. 8. A silicone sealant according to Claim 7, wherein R1 is methylene, R2 is propylene, R3 is methyl, and r4 and R5 are selected from the group consisting of methyl and ethyl. 9. A silicone sealant according to Claim 8 wherein R4 is methyl and R5 is ethyl.

Inventors: BEERS M DALE, THOMPSON JAMES E, BEERS, M., DALE, THOMPSON, JAMES, E.
Applicants: LOCTITE CORP, LOCTITE CORPORATION
Application year: 1986
Main classification: C08L83
IPC codes: C07F7, C08K5, C08L83, C09K3