JPH09165556A - Low-viscosity silicone composition - Google Patents
Low-viscosity silicone compositionInfo
- Publication number
- JPH09165556A JPH09165556A JP22427996A JP22427996A JPH09165556A JP H09165556 A JPH09165556 A JP H09165556A JP 22427996 A JP22427996 A JP 22427996A JP 22427996 A JP22427996 A JP 22427996A JP H09165556 A JPH09165556 A JP H09165556A
- Authority
- JP
- Japan
- Prior art keywords
- composition
- group
- silica
- viscosity
- alkoxysilane
- 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.)
- Withdrawn
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D183/00—Coating compositions based on 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; Coating compositions based on derivatives of such polymers
- C09D183/04—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
- C08G77/18—Polysiloxanes containing silicon bound to oxygen-containing groups to alkoxy or aryloxy groups
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
- C09D5/16—Antifouling paints; Underwater paints
- C09D5/1656—Antifouling paints; Underwater paints characterised by the film-forming substance
- C09D5/1662—Synthetic film-forming substance
- C09D5/1675—Polyorganosiloxane-containing compositions
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Paints Or Removers (AREA)
Abstract
Description
【０００１】[0001]
【産業上の利用分野】本発明は新規組成物に関する。特
に本発明は表面を生物による汚染から保護するために使
用し得る低粘度シリカ充填剤含有組成物に関するもので
ある。FIELD OF THE INVENTION The present invention relates to novel compositions. In particular, the present invention relates to low viscosity silica filler containing compositions that can be used to protect surfaces from biological contamination.
【０００２】[0002]
【従来の技術】水（清水又は海水のいずれであっても）
に暴露されている構造物はしばしば多くの物体及び生物
の外皮で覆われるようになる。代表的なかゝる構造物は
しばしば船体、ブイ、製油プラットフォームのスプラッ
シュ帯域表面及び発電所の取入口及び排出口を包含す
る。これらはたとえば氷のような物体及びフジツボ、チ
ューブウォーム、藻類及びゼブラむらさきいがいのよう
な生物（これらはいずれも構造物の性能に著しい悪影響
を与える）の外皮で覆われるようになる。2. Description of the Related Art Water (whether fresh water or seawater)
Structures that have been exposed to are often covered by the skin of many objects and organisms. Typical such structures often include hulls, buoys, splash zone surfaces on refinery platforms, and power plant intakes and exhausts. They come to be covered, for example, by objects such as ice and the skin of organisms such as barnacles, tubeworms, algae and zebra gargles, both of which have a significant negative effect on the performance of the structure.
【０００３】上述したような構造物が物体及び生物の外
皮で覆われることを阻止するために湿分硬化性、二液型
シリコーン組成物が該構造物に被覆として使用されてい
る。しかしながら、慣用的に使用されるシリコーン組成
物は高分子量ポリシロキサンからなり、未硬化状態で高
い粘度をもち、したがってかゝるシリコーン組成物の取
扱い及び施用をきわめて困難にする。このため、かゝる
シリコーン組成物はしばしば環境に対して不都合な有機
溶剤で希釈され、それによって該組成物の取扱い及び施
用を容易にしているのが実情である。Moisture-curing, two-part silicone compositions have been used as coatings on structures such as those described above to prevent them from being covered by the skin of objects and organisms. However, conventionally used silicone compositions are composed of high molecular weight polysiloxanes and have a high viscosity in the uncured state, thus making handling and application of such silicone compositions extremely difficult. For this reason, such silicone compositions are often diluted with environmentally unfriendly organic solvents, thereby facilitating handling and application of the compositions.
【０００４】有機溶剤の使用を回避するための試みにお
いて、低分子量シラノール末端停止重合体及び非補強用
充填剤を含む低粘度組成物が製造された。しかしなが
ら、これらの組成物は硬化状態で貧弱な物理的性質を示
すので望ましくない。これらの組成物の硬化後の物理的
性質を高めるための試みとして、これらの低粘度組成物
にシリカが混合された。しかしながら、得られる混合物
は硬化前の粘度の劇的な増加を示す；実際、かゝる混合
物の粘度は高分子量ポリオルガノシロキサンを含む組成
物が示す粘度よりも高くなる。In an attempt to avoid the use of organic solvents, low viscosity compositions containing low molecular weight silanol terminated polymers and non-reinforcing fillers have been prepared. However, these compositions are not desirable because they exhibit poor physical properties in the cured state. Silica was incorporated into these low viscosity compositions in an attempt to enhance the post cure physical properties of these compositions. However, the resulting mixture exhibits a dramatic increase in viscosity before cure; in fact, the viscosity of such a mixture is higher than that of the composition containing the high molecular weight polyorganosiloxane.
【０００５】したがって、本発明は硬化後に望ましい物
理的性質及び汚染物剥離性を示す低粘度シリカ充填剤含
有組成物を意図するものである。室温硬化性組成物の製
造については種々の研究が発表されている。本出願人自
身の米国特許第４，９５９，４０７号明細書には無溶剤
オルガノポリシロキサン組成物が記載されており、該組
成物はカップリング剤としてビス（ウレイド）シラン及
び架橋剤としてアミノキシシロキサンを含有してなるも
のである。Accordingly, the present invention contemplates low viscosity silica filler containing compositions which exhibit desirable physical properties and stain release properties after cure. Various studies have been published on the production of room temperature curable compositions. Applicant's own U.S. Pat. No. 4,959,407 describes solventless organopolysiloxane compositions which contain bis (ureido) silane as a coupling agent and aminoxy as a crosslinker. It contains siloxane.
【０００６】さらに、米国特許第４，９６５，３６７号
明細書には、シラシクロブタンの製造法が記載されてお
り、この方法はハロゲン置換シラシクロブタンをシリル
化試薬と反応させる工程を包含する。さらに別の研究者
は硬化性組成物の製造法について研究した。米国特許第
３，６９４，４２７号明細書にはシラシクロブタン及び
オルガノポリシロキサンを含有してなる組成物が記載さ
れている。Further, US Pat. No. 4,965,367 describes a process for preparing silacyclobutane, which process comprises reacting a halogen-substituted silacyclobutane with a silylating reagent. Yet another researcher has studied methods of making curable compositions. U.S. Pat. No. 3,694,427 describes a composition comprising silacyclobutane and an organopolysiloxane.
【０００７】[0007]
【発明の概要】本発明は、つぎの成分： （ａ）アルコキシシラン末端停止重合体； （ｂ）シリカベース充填剤；及び （ｃ）縮合触媒； を含有してなり、しかも揮発性有機化合物（ＶＯＣ）を
含まない噴霧し得る組成物を提供するものである。SUMMARY OF THE INVENTION The present invention comprises the following components: (a) an alkoxysilane end-terminated polymer; (b) a silica-based filler; and (c) a condensation catalyst; and a volatile organic compound ( A VOC) -free sprayable composition is provided.
【０００８】本発明の組成物は、驚くべきことに、低分
子量シラノール末端停止重合体及び炭酸カルシウムのよ
うな非補強用充填剤を含有する組成物のような慣用的な
低粘度組成物と実質的に同等の粘度を示す。さらに、こ
れらの組成物は、驚くべきことに、低分子量シラノール
末端停止重合体及びシリカベース補強用充填剤を含有す
る組成物より低い、少なくとも約１／１０未満、好まし
くは約１／３０未満、もっとも好ましくは約１／６０未
満である粘度を示す。本明細書において使用する用語
“低粘度”は周囲温度において、約３０，０００ｃｐｓ
未満、好ましくは約２０，０００ｃｐｓ未満、もっとも
好ましくは約１０，０００ｃｐｓ未満の粘度を意味する
ものと定義される。本明細書において使用する用語“低
分子量”は約１００，０００未満、好ましくは約６０，
０００未満、もっとも好ましくは約４５，０００未満の
Ｍｗを意味するものと定義される。The compositions of the present invention are surprisingly substantially compatible with conventional low viscosity compositions such as those containing low molecular weight silanol terminated polymers and non-reinforcing fillers such as calcium carbonate. Shows similar viscosity. Moreover, these compositions are surprisingly lower than those containing low molecular weight silanol-terminated polymers and silica-based reinforcing fillers, at least less than about 1/10, preferably less than about 1/30, Most preferably it exhibits a viscosity of less than about 1/60. As used herein, the term "low viscosity" means about 30,000 cps at ambient temperature.
Is defined to mean a viscosity of less than, preferably less than about 20,000 cps, and most preferably less than about 10,000 cps. As used herein, the term "low molecular weight" is less than about 100,000, preferably about 60,
It is defined as meaning an Mw of less than 000, most preferably less than about 45,000.
【０００９】本発明の組成物はさらにまた、驚くべきこ
とに、慣用の低粘度組成物と比較して硬化後にすぐれた
物理的性質を示す。本発明のこれらの予想外の結果は後
記の表のデータによって確認される。The compositions of the present invention also surprisingly exhibit excellent physical properties after curing as compared to conventional low viscosity compositions. These unexpected results of the present invention are confirmed by the data in the table below.
【００１０】[0010]
【発明の詳細な開示】本発明において使用し得るアルコ
キシシラン末端停止重合体については制限はない。しか
しながら、多くの場合、これらは式：DETAILED DISCLOSURE OF THE INVENTION There is no limitation on the alkoxysilane end-capped polymers that can be used in the present invention. However, in many cases, these are the formulas:
【００１１】[0011]
【化２】 Embedded image
【００１２】（式中、各Ｒは独立的にＣ1-10アルキル
基、Ｃ1-10アルコキシ基、フェニル基を包含する置換又
は非置換芳香族基、シアノエチル基を包含するシアノア
ルキル基、トリフルオルプロピル基を包含するトリハロ
アルキル基又はビニル基であり；各Ｒ1 は独立的にＣ
1-10アルキル基又は置換又は非置換基である）によって
表される。しかしながら、各Ｒはメチル基でありそして
各Ｒ1 はメチル基であることが好ましい。ｎは約２５な
いし５，０００の整数でありそして好ましくはアルコキ
シシラン末端停止重合体の粘度が約１００ないし約２
０，０００、好ましくは約２００ないし約１５，００
０、もっとも好ましくは約１，０００ないし約１０，０
００であるような値をもつ。(Wherein each R is independently a C 1-10 alkyl group, a C 1-10 alkoxy group, a substituted or unsubstituted aromatic group including a phenyl group, a cyanoalkyl group including a cyanoethyl group, and a trifluoro group. A trihaloalkyl group including a propyl group or a vinyl group; each R 1 is independently C
1-10 alkyl group or a substituted or unsubstituted group). However, it is preferred that each R is a methyl group and each R 1 is a methyl group. n is an integer of from about 25 to 5,000 and preferably the viscosity of the alkoxysilane-terminated polymer is from about 100 to about 2.
10,000, preferably about 200 to about 15,000
0, most preferably about 1,000 to about 10.0
It has a value that is 00.
【００１３】かゝるアルコキシシラン末端停止重合体は
商業的に入手可能であり、たとえばシラノール末端停止
ポリオルガノシロキサンと三官能性又は四官能性アルコ
キシシランとをキャッピング触媒の存在下で反応させる
ことによって製造される。本発明において使用し得るシ
リカベース充填剤については本質的に制限はない。しか
しながら、商業的に入手し得るヒュームドシリカがしば
しば好ましい。Such alkoxysilane-terminated polymers are commercially available, for example by reacting a silanol-terminated polyorganosiloxane with a trifunctional or tetrafunctional alkoxysilane in the presence of a capping catalyst. Manufactured. There is essentially no limitation as to the silica-based filler that can be used in the present invention. However, commercially available fumed silica is often preferred.
【００１４】本発明において使用し得る縮合触媒につい
ても本質的に制限はない。多くの場合、これらはセリウ
ム、亜鉛及び鉛の塩、たとえばそれらのカルボン酸塩を
包含する。好ましい触媒はたとえばジブチル錫−ビス−
アセチルアセトネート、ジブチル錫ジラウレート及びジ
イソプロポキシビス−２，４−ビス−ペンタンジオナト
チタン（IV）を包含するチタンまたは錫を含有する触媒
である。There is essentially no limitation as to the condensation catalyst that can be used in the present invention. Often, these include salts of cerium, zinc and lead, such as their carboxylates. A preferred catalyst is, for example, dibutyltin-bis-
Catalysts containing titanium or tin, including acetylacetonate, dibutyltin dilaurate and diisopropoxybis-2,4-bis-pentanedionato titanium (IV).
【００１５】本発明の組成物はたとえばアルコキシシラ
ン末端停止シラノール重合体、シリカベース充填剤及び
縮合触媒を混合できる任意の混合容器中で製造し得る。
反応試薬の混合順序は一般に制限されない。しかしなが
ら、縮合触媒を添加する前にアルコキシシラン末端停止
シラノール重合体及びシリカベース充填剤を含む予備混
合物を形成することがしばしば好ましい。The composition of the present invention may be prepared in any mixing vessel in which, for example, an alkoxysilane-terminated silanol polymer, silica-based filler and condensation catalyst can be mixed.
The mixing order of the reaction reagents is not generally limited. However, it is often preferable to form a premix containing the alkoxysilane-terminated silanol polymer and the silica-based filler before adding the condensation catalyst.
【００１６】本発明の好ましい一実施態様においては、
硬化を促進するために架橋剤を添加することが望まし
い。本発明において使用し得る架橋剤については、それ
らがアルコキシシラン末端停止重合体を架橋して硬化組
成物を製造し得るものであること以外には制限はない。
多くの場合本発明において使用される好ましい架橋剤は 式： Ｘ1 (4-q) −Ｓｉ−Ｚq （式中、各Ｘ1 は独立的にＣ1-10炭化水素基、好ましく
はメチル基でありそして各Ｚは独立的にメトキシ基を包
含するアルコキシ基、アミノキシ基、ジメチルアミノ基
を包含するジアルキルアミノ基、オキシム基又はメトキ
シ基を包含するアルコキシ基でありそしてｑは３又は４
である）をもつ多官能性オルガノポリシロキサンであ
る。In a preferred embodiment of the invention,
It is desirable to add a cross-linking agent to accelerate curing. There is no limitation with respect to the cross-linking agents that can be used in the present invention, except that they are capable of cross-linking alkoxysilane-terminated polymers to produce cured compositions.
Often the preferred crosslinkers used in the present invention are of the formula: X 1 (4-q) -Si-Z q , where each X 1 is independently a C 1-10 hydrocarbon group, preferably a methyl group. And each Z is independently an alkoxy group including a methoxy group, an aminoxy group, a dialkylamino group including a dimethylamino group, an oxime group or an alkoxy group including a methoxy group, and q is 3 or 4
Is a polyfunctional organopolysiloxane having
【００１７】かゝる架橋剤は典型的には上述の予備混合
物又は縮合触媒に添加され、そしてたとえばヒドロキシ
アミン又はアルコールをシリコーンハイドライドと反応
させることによって製造し得る。架橋剤の製造について
のより詳細な開示はこゝに参考文献として引用する米国
特許第４，９５９，４０７号明細書中に与えられてい
る。Such crosslinkers are typically added to the premixes or condensation catalysts described above and may be prepared, for example, by reacting a hydroxyamine or alcohol with a silicone hydride. A more detailed disclosure of making crosslinkers is provided in US Pat. No. 4,959,407, which is incorporated herein by reference.
【００１８】当該技術において既知の任意慣用の添加剤
を使用することも本発明の範囲内である。かゝる添加剤
の例は油、炭酸カルシウム及び硫酸カルシウムのような
周期律表第IIＡ族炭酸塩及び硫酸塩、酸化チタン及び酸
化第二鉄のような遷移金属酸化物、カーボンブラック、
珪藻土、アルミナ、アルミナ水和物、ガラス微小球、石
英、有機充填剤ならびに補強用及び非補強用充填剤を包
含する。It is also within the scope of the present invention to use any conventional additive known in the art. Examples of such additives are oils, Group IIA carbonates and sulfates of the Periodic Table, such as calcium carbonate and calcium sulfate, transition metal oxides such as titanium oxide and ferric oxide, carbon black,
Includes diatomaceous earth, alumina, alumina hydrate, glass microspheres, quartz, organic fillers and reinforcing and non-reinforcing fillers.
【００１９】さらに、当該技術において既知の任意慣用
の接着促進剤を使用することも本発明の範囲内である。
かゝる接着促進剤の例は３−アミノプロピルトリメトキ
シシラン、３−アミノエチルトリエトキシシラン及びＮ
−（２−アミノエチル−３−アミノプロピル）トリメト
キシシランのような含窒素シラン及び３−（グリシドキ
シプロピル）トリメトキシシランのようなエポキシド含
有シラン及び１，３，５−トリス（３−トリメトキシシ
リルプロピル）イソシアヌレートのようなシアヌレート
含有シランを包含する。Further, it is within the scope of the present invention to use any conventional adhesion promoter known in the art.
Examples of such adhesion promoters are 3-aminopropyltrimethoxysilane, 3-aminoethyltriethoxysilane and N.
Nitrogen-containing silanes such as-(2-aminoethyl-3-aminopropyl) trimethoxysilane and epoxide-containing silanes such as 3- (glycidoxypropyl) trimethoxysilane and 1,3,5-tris (3- Cyanurate containing silanes such as trimethoxysilylpropyl) isocyanurate.
【００２０】本発明に述べた新規組成物の用途に関して
は制限はない；実際、これらの組成物はたとえば保護被
覆及び／又はコーキング材／シーラントとして使用し得
る。さらに、本発明の組成物は吹付、刷毛塗及びこて塗
を包含する任意慣用の方法によって塗布し得る。本発明
の組成物におけるアルコキシシラン末端停止シラノール
重合体、シリカベース充填剤及び縮合触媒の使用量は硬
化性組成物が製造されるという範囲でのみ制限される。
しかしながら、アルコキシシラン末端停止シラノール重
合体はシリカベース充填剤１重量部当たりしばしば約２
０重量部を超えない量、好ましくは約１５重量部を超え
ない量、もっとも好ましくは約１０重量部を超えない量
で使用される。There is no limitation as to the use of the novel compositions mentioned in the present invention; in fact, these compositions may be used, for example, as protective coatings and / or caulks / sealants. Further, the compositions of the present invention may be applied by any conventional method including spraying, brushing and troweling. The amount of alkoxysilane-terminated silanol polymer, silica-based filler and condensation catalyst used in the composition of the present invention is limited only to the extent that a curable composition is produced.
However, alkoxysilane-terminated silanol polymers are often about 2 per part by weight of silica-based filler.
It is used in an amount of no more than 0 parts by weight, preferably no more than about 15 parts by weight, and most preferably no more than about 10 parts by weight.
【００２１】さらに、縮合触媒は予備混合物（アルコキ
シシラン末端停止シラノール重合体及びシリカベース充
填剤の混合物）１００重量部当たり約１０重量部を超え
ない量、好ましくは約５重量部を超えない量、もっとも
好ましくは約１重量部を超えない量で使用される。Further, the condensation catalyst is not more than about 10 parts by weight, preferably not more than about 5 parts by weight per 100 parts by weight of the premix (mixture of alkoxysilane-terminated silanol polymer and silica-based filler). Most preferably, it is used in an amount not exceeding about 1 part by weight.
【００２２】[0022]
【実施例の記載】つぎに本発明の理解をより容易にする
一助として本発明を実施例によってさらに具体的に説明
する。得られる生成物は 1Ｈ及び13Ｃ核磁気共鳴スペク
トル分析、質量スペクトル分析、赤外スペクトル分析及
びＧＰＣ分析のような慣用の技術によって確認し得る。DESCRIPTION OF THE PREFERRED EMBODIMENTS Next, the present invention will be described in more detail with reference to the examples, in order to facilitate the understanding of the present invention. The resulting product may be identified by conventional techniques such as 1 H and 13 C nuclear magnetic resonance spectroscopy, mass spectroscopy, infrared spectroscopy and GPC analysis.
【００２３】実施例１ シラノール末端停止ポリジメチルシロキサン（周囲温度
において３０００センチポイズの粘度）５００ｇ、メチ
ルトリメトキシシラン２０ｇ、第２級ブチルアミン１．
０ｇ及び酢酸０．５ｇを混合容器に装入した。得られる
混合物を６０℃に１時間加熱し、ついで約４５℃に冷却
し、その時点でヘキサメチルジシラザン２．５ｇをメタ
ノール掃去剤として添加した。得られる重合体はアルコ
キシシラン末端停止重合体であり、収率は約９５％であ
った。 Example 1 500 g of silanol-terminated polydimethylsiloxane (viscosity of 3000 centipoise at ambient temperature), 20 g of methyltrimethoxysilane, secondary butylamine 1.
0 g and 0.5 g acetic acid were charged to the mixing vessel. The resulting mixture was heated to 60 ° C for 1 hour, then cooled to about 45 ° C, at which point 2.5 g of hexamethyldisilazane was added as a methanol scavenger. The obtained polymer was an alkoxysilane end-terminated polymer, and the yield was about 95%.
【００２４】実施例２ 実施例１で製造されたアルコキシシラン末端停止重合体
１０．０ｇ及びジブチル錫ジラウレート０．１ｇを混合
容器に装入した。得られる混合物を周囲条件下で大気湿
分に暴露すると１時間以内に指触乾燥性になりそして１
０時間後にはエラストマー状態に硬化した。 Example 2 10.0 g of the alkoxysilane end-terminated polymer prepared in Example 1 and 0.1 g of dibutyltin dilaurate were placed in a mixing vessel. Exposure of the resulting mixture to atmospheric moisture under ambient conditions rendered it dry to the touch within 1 hour and
After 0 hours, it was cured into an elastomer state.
【００２５】実施例３ 実施例３は実施例２に述べたと同様の方法で、たゞしジ
ブチル錫ジラウレートの代わりにジイソプロポキシビス
−２，４−ビス−ペンタンジオナトチタン（IV）を使用
して実施した。得られる組成物は１時間以内に指触乾燥
性となり、１０時間後にはエラストマー状態に硬化し
た。 Example 3 Example 3 is a method similar to that described in Example 2, except that diisopropoxybis-2,4-bis-pentanedionate titanium (IV) is used instead of dibutyltin dilaurate. It was carried out. The resulting composition became dry to the touch within an hour and cured into an elastomer after 10 hours.
【００２６】実施例４ メチルトリメトキシシラン末端停止ポリジメチルシロキ
サン（周囲温度において３０００センチポイズの粘度）
４３４．５ｇ及びヘキサメチルジシラザン及びオクタメ
チルシクロテトラシロキサンで処理されたシリカ１３１
ｇを混合容器に装入した。上記のシリカは攪拌しつゝ５
回に分けて添加した。シリカの全量を添加した後、メチ
ルトリメトキシシラン末端停止ポリジメチルシロキサン
の別量４３４．５ｇを添加した。得られる混合物を約５
分間真空吸引し、ついで高剪断ミキサーで約２０００サ
イクル処理した。得られた組成物はシリカベース補強用
充填剤を含む低粘度組成物（周囲温度で約７０００セン
チポイズの粘度）であった。 Example 4 Methyltrimethoxysilane end-capped polydimethylsiloxane (viscosity of 3000 centipoise at ambient temperature)
Silica 131 treated with 434.5 g and hexamethyldisilazane and octamethylcyclotetrasiloxane
g was charged to the mixing vessel. The above silica is stirred 5
It was added in portions. After all the silica was added, another 434.5 g of methyltrimethoxysilane end-capped polydimethylsiloxane was added. The resulting mixture is approximately 5
Vacuum was applied for a minute and then processed in a high shear mixer for about 2000 cycles. The resulting composition was a low viscosity composition with a silica-based reinforcing filler (viscosity of about 7000 centipoise at ambient temperature).
【００２７】実施例５ 実施例５は実施例４に述べたと同様の方法で、たゞしシ
リカの代わりに炭酸カルシウムを使用して実施した。得
られる組成物は周囲温度で約７０００センチポイズの粘
度を有していた。実施例６ 実施例４で製造したアルコキシシラン末端停止重合体１
００ｇ、テトラエチルオルトシリケート３．０ｇ及びジ
ブチル錫−ビス−アセチルアセトネート０．６５ｇを混
合容器に装入した。混合後、得られる組成物を遠心分離
によって脱ガスし、金型中に注入しそして硬化して分析
に供した。 Example 5 Example 5 was carried out in the same manner as described in Example 4, using calcium carbonate instead of silica. The resulting composition had a viscosity of about 7000 centipoise at ambient temperature. Example 6 Alkoxysilane end-capped polymer 1 prepared in Example 4
00 g, tetraethyl orthosilicate 3.0 g and dibutyltin-bis-acetylacetonate 0.65 g were charged to a mixing vessel. After mixing, the resulting composition was degassed by centrifugation, poured into a mold and cured for analysis.
【００２８】実施例７ 実施例７は実施例４に述べたと同様の方法で、たゞし組
成物の約１０重量％シリコーン油（周囲温度で２０セン
チポイズの粘度をもつポリジメチルシロキサン）を含ま
せて実施した。この組成物を固体基材上に吹付塗布しそ
して硬化させて望ましいフィルム性能を示すエラストマ
ーを得た。 Example 7 Example 7 was prepared in the same manner as described in Example 4, except that about 10% by weight of the silicone composition (polydimethylsiloxane having a viscosity of 20 centipoise at ambient temperature) was added. It was carried out. This composition was spray coated onto a solid substrate and cured to give an elastomer exhibiting desirable film performance.
【００２９】表Ｉのデータはシラノール末端停止重合体
を含む慣用の組成物と比較して本発明の組成物が低粘度
を示すことを実証するために提示するものである。すべ
ての組成物は上記の実施例に述べたと同様の方法で製造
した。 表 Ｉ 試料番号 重合体a 重合体粘度b 充填剤 組成物粘度b １ ｘ ３，０００ ＣａＣＯ3 ７，０００ ２ ｘ ３，０００ シリカ ４６０，０００ ３ ｙ ３，０００ シリカ ７，０００ 注 a ｘ＝シラノール末端停止ポリジメチルシロキサン； ｙ＝アルコキシシラン末端停止ポリジメチルシロキサン； b 周囲温度における粘度、センチポイズ。The data in Table I is presented to demonstrate that the compositions of the present invention exhibit low viscosity as compared to conventional compositions containing silanol terminated polymers. All compositions were prepared in a manner similar to that described in the above examples. Table I Sample Number Polymer a Polymer viscosity b Filler composition viscosity b 1 x 3,000 CaCO 3 7,000 2 x 3,000 Silica 460,000 3 y 3,000 Silica 7,000 Note a x = silanol End-terminated polydimethylsiloxane; y = alkoxysilane end-terminated polydimethylsiloxane; b viscosity at ambient temperature, centipoise.
【００３０】表IIのデータは本発明の組成物の硬化後の
すぐれた性質を実証するために提示するものである。す
べての組成物は上記の実施例に述べたと同様の方法で製
造した。 表 II 試料 引裂強さf 引張応力f 引張歪f 番号 a 充填剤の量b lbs/in psi % ショアＡ硬度f 1 なし 4.4 24.2 23.7 15 2 CaCO3 5% 7.70±0.4 48.5 69.5 18 3 CaCO3 9% 8.07±1.96 82.0 130.0 18 4 CaCO3 13% 9.73±0.85 94.2 131.0 18 5 CaCO3 29% 13.7±0.61 175.9 154.0 30 6 シリカ 5% 11.5 102.9 120.0 21 7 シリカ 9% 14.7±0.99 306.0 214.0 27 8 シリカ 13% 21±0.91 396.4 203.0 30 9 シリカ 13%c 1.23±0.53 206.0 163.0 23 10 シリカ 13%d 25.3±1.4 296.0 204.0 32 11 シリカ 13%c 28.4±3.73 296.0 196.0 28 注 a すべての試料は実施例１で製造されたアルコキシ
シラン末端停止シラノール重合体を用いて製造した。The data in Table II are for the cured compositions of the present invention.
It is presented to demonstrate its superior properties. You
All compositions were prepared in the same manner as described in the above examples.
I made it.Table II Tear strength of samplef Tensile stressf Tensile strainf number a Amount of filler b lbs / in psi % Shore A hardness f 1 None 4.4 24.2 23.7 15 2 CaCOThree 5% 7.70 ± 0.4 48.5 69.5 18 3 CaCOThree 9% 8.07 ± 1.96 82.0 130.0 18 4 CaCOThree 13% 9.73 ± 0.85 94.2 131.0 18 5 CaCOThree 29% 13.7 ± 0.61 175.9 154.0 30 6 Silica 5% 11.5 102.9 120.0 21 7 Silica 9% 14.7 ± 0.99 306.0 214.0 27 8 Silica 13% 21 ± 0.91 396.4 203.0 30 9 Silica 13%c 1.23 ± 0.53 206.0 163.0 23 10 Silica 13%d 25.3 ± 1.4 296.0 204.0 32 11 Silica 13%c 28.4 ± 3.73 296.0 196.0 28 NoteaAll samples were alkoxy prepared in Example 1.
It was prepared using a silane-terminated silanol polymer.
【００３１】b 量＝組成物の全重量に基づく重量％。c 添加したシリコーン油、組成物の全重量に基づいて２
０％。d ジイソプロポキシビス−２，４−ビス−ペンタンジオ
ナトチタン（IV）０．１ｇを実施例２におけるごとく添
加した。e 使用したカップリング剤＝１，１−ジメトキシシラシ
クロペンタン。 B amount = wt% based on the total weight of the composition. c Silicone oil added, 2 based on total weight of composition
0%. d 0.1 g of diisopropoxybis-2,4-bis-pentanedionato titanium (IV) was added as in Example 2. e Coupling agent used = 1,1-dimethoxysilacyclopentane.
【００３２】f すべてＡＳＴＭ試験法に従って測定。 F All measured according to ASTM test method.
───────────────────────────────────────────────────── フロントページの続き (72)発明者 ジュディス・スタイン アメリカ合衆国、ニューヨーク州、スケネ クタデイ、ユニオン・ストリート、1005番 ─────────────────────────────────────────────────── ─── Continuation of the front page (72) Inventor Judith Stein, Union Street, Schenectady, New York, USA No. 1005
Claims (11)
度で約３０，０００センチポイズ未満の粘度をもつ噴霧
し得る組成物。1. A composition comprising: (a) an alkoxysilane end-terminated polymer; (b) a silica-based filler; and (c) a condensation catalyst; containing no volatile organic compound and at ambient temperature. A sprayable composition having a viscosity of less than about 30,000 centipoise.
式： 【化１】 （式中、各Ｒは独立的にＣ1-10アルキル基、アルコキシ
基、置換又は非置換芳香族基、シアノアルキル基、トリ
ハロアルキル基又はビニル基であり；各Ｒ1 は独立的に
Ｃ1-10アルキル基又は置換又は非置換基であり；そして
ｎは約２５ないし５，０００の整数である）をもつ請求
項１記載の組成物。2. The alkoxysilane terminated polymer has the formula: (Wherein each R is independently a C 1-10 alkyl group, an alkoxy group, a substituted or unsubstituted aromatic group, a cyanoalkyl group, a trihaloalkyl group or a vinyl group; each R 1 is independently a C 1 -10 alkyl group or a substituted or unsubstituted group; and n is an integer of about 25 to 5,000).
チル基である請求項２記載の組成物。3. The composition according to claim 2, wherein each R is a methyl group and each R 1 is a methyl group.
カである請求項１記載の組成物。4. The composition of claim 1, wherein the silica-based filler is fumed silica.
る請求項１記載の組成物。5. The composition according to claim 1, wherein the condensation catalyst contains titanium or tin.
ス−２，４−ペンタンジオナトチタン（IV）でありそし
て該錫含有触媒がジブチル錫−ビス−アセチルアセトネ
ート又はジブチル錫ジラウレートである請求項５記載の
組成物。6. The titanium-containing catalyst is diisopropoxybis-2,4-pentanedionato titanium (IV) and the tin-containing catalyst is dibutyltin-bis-acetylacetonate or dibutyltin dilaurate. The composition according to 5.
ンチポイズ未満の粘度をもつ請求項１記載の組成物。7. The composition of claim 1, wherein the composition has a viscosity at ambient temperature of less than about 20,000 centipoise.
請求項１記載の組成物。8. The composition according to claim 1, wherein the composition further comprises a crosslinking agent.
請求項１記載の組成物。9. The composition according to claim 1, wherein the composition further comprises an additive.
塩及び硫酸塩、遷移金属酸化物、カーボンブラック、珪
藻土、アルミナ、アルミナ水和物、ガラス微小球、石英
又は有機充填剤である請求項１０記載の組成物。10. The additive is oil, Group IIA carbonates and sulfates of the Periodic Table, transition metal oxides, carbon black, diatomaceous earth, alumina, alumina hydrates, glass microspheres, quartz or organic fillers. 11. The composition of claim 10, which is certain.
てなる請求項１記載の組成物。11. The composition of claim 1 wherein said composition further comprises an adhesion promoter.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US55161895A | 1995-11-01 | 1995-11-01 | |
| US08/551618 | 1995-11-01 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH09165556A true JPH09165556A (en) | 1997-06-24 |
Family
ID=24202004
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP22427996A Withdrawn JPH09165556A (en) | 1995-11-01 | 1996-08-27 | Low-viscosity silicone composition |
Country Status (4)
| Country | Link |
|---|---|
| JP (1) | JPH09165556A (en) |
| DE (1) | DE19633413A1 (en) |
| FR (1) | FR2740464B1 (en) |
| GB (1) | GB2306491A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2002241695A (en) * | 2000-12-15 | 2002-08-28 | Dow Corning Toray Silicone Co Ltd | Water-repellent silicone coating agent composition |
| WO2005012441A1 (en) * | 2003-08-05 | 2005-02-10 | Shunichi Yamazaki | Additive for ship bottom paint and ship bottom paint comprising the same |
| KR100648563B1 (en) * | 1998-01-27 | 2006-11-24 | 제이에스알 가부시끼가이샤 | Coating Composition and Its Cured Product |
| CN100381509C (en) * | 2003-08-05 | 2008-04-16 | 山崎俊一 | Additive for ship bottom paint and ship bottom paint comprising the same |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5904988A (en) * | 1997-05-27 | 1999-05-18 | General Electric Company | Sprayable, condensation curable silicone foul release coatings and articles coated therewith |
| DE10307762A1 (en) * | 2003-02-16 | 2004-09-09 | Stiftung Alfred-Wegener-Institut Für Polar- Und Meeresforschung | Viscoelastic coating paste for protection against macro growth and process for producing a coating |
| US7048788B2 (en) * | 2003-08-05 | 2006-05-23 | Shunichi Yamazaki | Ship bottom paint using coal ash and diatomaceous earth |
| CA2656603A1 (en) * | 2006-07-07 | 2008-01-10 | Henkel Corporation | Low modulus, humidity resistant silicone rtv compositions and method of preparing same |
| US20150210909A1 (en) | 2012-08-10 | 2015-07-30 | Sika Technology Ag | Weather-resistant silicone mixture having improved green strength |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ZA837557B (en) * | 1982-12-13 | 1984-07-25 | Gen Electric | Alkoxy-functional one-component rtv silicone rubber compositions |
| US4472551A (en) * | 1983-04-01 | 1984-09-18 | General Electric Company | One package, stable, moisture curable, alkoxy-terminated organopolysiloxane compositions |
| US4563498A (en) * | 1984-07-05 | 1986-01-07 | General Electric Company | Curable silicone compositions and processes |
| DE3523206A1 (en) * | 1985-06-28 | 1987-01-02 | Bayer Ag | METHOD FOR PRODUCING POLY (DIORGANOSILOXANES) WITH ALKOXY END GROUPS |
| GB8803458D0 (en) * | 1988-02-15 | 1988-03-16 | Int Paint Plc | Inhibition of marine fouling |
| GB9014564D0 (en) * | 1990-06-29 | 1990-08-22 | Courtaulds Coatings Holdings | Coating compositions |
| US5213899A (en) * | 1990-12-17 | 1993-05-25 | General Electric Company | Room temperature vulcanizable silicone compositions |
| JPH04359058A (en) * | 1991-06-03 | 1992-12-11 | Shin Etsu Chem Co Ltd | Room temperature curing organopolysiloxane composition and its production |
| US5266631A (en) * | 1991-06-13 | 1993-11-30 | Shin-Etsu Chemical Co., Ltd. | Process of producing room temperature curable organopolysiloxane composition |
-
1996
- 1996-08-20 DE DE1996133413 patent/DE19633413A1/en not_active Withdrawn
- 1996-08-21 GB GB9617490A patent/GB2306491A/en not_active Withdrawn
- 1996-08-23 FR FR9610389A patent/FR2740464B1/en not_active Expired - Fee Related
- 1996-08-27 JP JP22427996A patent/JPH09165556A/en not_active Withdrawn
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100648563B1 (en) * | 1998-01-27 | 2006-11-24 | 제이에스알 가부시끼가이샤 | Coating Composition and Its Cured Product |
| JP2002241695A (en) * | 2000-12-15 | 2002-08-28 | Dow Corning Toray Silicone Co Ltd | Water-repellent silicone coating agent composition |
| WO2005012441A1 (en) * | 2003-08-05 | 2005-02-10 | Shunichi Yamazaki | Additive for ship bottom paint and ship bottom paint comprising the same |
| CN100381509C (en) * | 2003-08-05 | 2008-04-16 | 山崎俊一 | Additive for ship bottom paint and ship bottom paint comprising the same |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2740464A1 (en) | 1997-04-30 |
| GB9617490D0 (en) | 1996-10-02 |
| FR2740464B1 (en) | 1999-03-05 |
| DE19633413A1 (en) | 1997-05-07 |
| GB2306491A (en) | 1997-05-07 |
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