WO2011007723A1 - シリコーン化合物用溶剤組成物 - Google Patents
シリコーン化合物用溶剤組成物 Download PDFInfo
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- WO2011007723A1 WO2011007723A1 PCT/JP2010/061670 JP2010061670W WO2011007723A1 WO 2011007723 A1 WO2011007723 A1 WO 2011007723A1 JP 2010061670 W JP2010061670 W JP 2010061670W WO 2011007723 A1 WO2011007723 A1 WO 2011007723A1
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- WIPO (PCT)
- Prior art keywords
- silicone compound
- silicone
- chloro
- trifluoropropene
- solvent composition
- Prior art date
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C21/00—Acyclic unsaturated compounds containing halogen atoms
- C07C21/02—Acyclic unsaturated compounds containing halogen atoms containing carbon-to-carbon double bonds
- C07C21/18—Acyclic unsaturated compounds containing halogen atoms containing carbon-to-carbon double bonds containing fluorine
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- 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
Definitions
- the present invention relates to a solvent composition used for dissolving and diluting a silicone compound.
- HCFCs hydrochlorofluorocarbons
- ODP ozone depletion potential
- HFCs hydrofluorocarbons
- HFEs hydrofluoroethers
- Patent Document 1 a method of adding 4 to 30% by mass of hexamethyldisiloxane (Patent Document 1), hydrocarbons such as normal hexane, alcohols and the like 15 to A method of adding 60% by mass (Patent Document 2) is disclosed.
- the silicone compound in the solvent is adjusted to a predetermined concentration. However, it is necessary to adjust the concentration of the silicone compound for each article.
- HFEs have been studied as solvents for silicone compounds having little adverse effect on the environment, but the compatibility between HFEs and silicone compounds is not sufficient, so the purpose of use (for example, adjusting the concentration of silicone compounds used) Therefore, it is necessary to add various organic solvents, which causes a problem that handling is not easy from the viewpoint of safety such as deterioration of applicability and flammability of the silicone compound.
- the present invention has been made in view of the above problems, and has a good silicone compound coating property, a non-flammability and low toxicity properties, and a silicone compound solvent composition that is extremely easy to handle.
- the issue is to provide goods.
- the present invention provides the inventions described in [Invention 1] to [Invention 9] below.
- [Invention 2] (A) 1-chloro-3,3,3-trifluoropropene, and (B) 1,1,2,2-tetrafluoro-1-methoxyethane, 1,1,1,3, A silicone compound comprising a compound consisting of at least one selected from the group consisting of 3-pentafluorobutane and 1,1,2,2-tetrafluoro-1- (2,2,2-trifluoroethoxy) ethane Solvent composition.
- Invention 3 As described in Invention 2, comprising 40 to 80% by mass of 1-chloro-3,3,3-trifluoropropene and 60 to 20% by mass of 1,1,2,2-tetrafluoro-1-methoxyethane Solvent composition for silicone compounds.
- Silicone compound according to Invention 2 comprising 60 to 80% by mass of 1-chloro-3,3,3-trifluoropropene and 40 to 20% by mass of 1,1,1,3,3-pentafluorobutane Solvent composition.
- invention 8 The silicone compound coating solution according to Invention 6 or 7 is applied to the surface of the article, and the silicone compound solvent composition in the coating solution is removed by evaporation to form a silicone compound coating on the article surface.
- a method for applying a silicone compound characterized by comprising:
- the solvent composition of the present invention 1-chloro-3,3,3-trifluoropropene having high solubility in a silicone compound, excellent drying properties, nonflammability and low toxicity is used as a solvent for silicone compounds. Used as Therefore, without adding an organic solvent in which problems such as flammability are a concern, the silicone compound has good applicability of the silicone compound, has nonflammability and low toxicity, and is extremely easy to handle. It is possible to provide a solvent composition.
- 1-chloro-3,3,3-trifluoropropene has a boiling point close to room temperature for both the cis form (Z form) and the trans form (E form). Therefore, the solvent composition of the present invention has a feature that it is very easy to handle when the silicone compound is dissolved, and the silicone compound is applied and dried.
- the solvent composition of the present invention has a global warming potential.
- the conversion factor is small and the greenhouse effect is small.
- the solvent composition for a silicone compound of the present invention contains 1-chloro-3,3,3-trifluoropropene.
- 1-Chloro-3,3,3-trifluoropropene Since 1-chloro-3,3,3-trifluoropropene, which is one of fluorine-containing unsaturated hydrocarbons, has a double bond, it has a high reactivity with OH radicals in the atmosphere and has an ozone depletion potential (ODP). ) And global warming potential (GWP) are significantly reduced.
- 1-Chloro-3,3,3-trifluoropropene is non-flammable and is a composition having non-flammability and low GWP characteristics.
- 1-Chloro-3,3,3-trifluoropropene used in the present invention is a known compound described in the literature, for example, addition reaction of hydrogen chloride to 3,3,3-trifluoropropyne, or 3- It can be produced by dehydroiodination reaction of chloro-1,1,1-trifluoro-3-iodopropane with potassium hydroxide.
- 1-chloro-3,3,3-trifluoropropene used in the present invention is a liquid phase fluorine produced by vapor phase fluorination reaction of 1,1,1,3,3-pentachloropropane with a chromium catalyst or without catalyst. It can also be obtained by performing a chemical reaction.
- 1-Chloro-3,3,3-trifluoropropene has cis isomer (Z isomer) and trans isomer (E isomer) as stereoisomers depending on the type of substituent, but both isomers are distilled. Can be separated and purified. The boiling point of the cis form (Z form) is 39.0 ° C., and the boiling point of the trans form (E form) is 21.0 ° C.
- 1-chloro-3,3,3-trifluoropropene can be used alone as a solvent for dissolving the silicone compound, but depending on the application, 1-chloro-3,3,3-trifluoropropene may be used. These solvents can also be added.
- 1-Chloro-3,3,3-trifluoropropene used in the present invention has a very high solubility and is a preferable solvent.
- the resin member may be damaged. Therefore, for the purpose of adjusting the dissolving ability, 1,1,2,2-tetrafluoro-1-to 1-chloro-3,3,3-trifluoropropene is used depending on the type of article to which the silicone compound is applied Methoxyethane (HFE-254pc), 1,1,1,3,3-pentafluorobutane (HFC-365mfc), 1,1,2,2-tetrafluoro-1- (2,2,2-trifluoroethoxy It is preferable to mix ethane (HFE-347pc-f), methyl nonafluoroisobutyl ether (HFE-7100) and the like.
- thermosetting resins such as phenol resin, epoxy resin, and polyurethane
- PE polyethylene
- PP polypropylene
- PVC polyvinyl chloride
- PTFE polytetrafluoroethylene
- acrylic resin PMMA
- PC polycarbonate
- PA polyamide
- PBT polybutylene terephthalate
- thermoplastic resins such as tarate (PET)
- fluororesins such as tetrafluoroethylene / ethylene copolymer (ETFE) and tetrafluoroethylene / hexafluoropropylene copolymer (FEP).
- the rubber member examples include nitrile rubber (NBR), styrene-butadiene rubber (SBR), ethylene-propylene-diene rubber (EPDM), chloroprene rubber (CR), synthetic rubber such as silicon rubber and urethane rubber, or Examples include natural rubber.
- NBR nitrile rubber
- SBR styrene-butadiene rubber
- EPDM ethylene-propylene-diene rubber
- CR chloroprene rubber
- synthetic rubber such as silicon rubber and urethane rubber, or Examples include natural rubber.
- the resin member or rubber member can be obtained by adding the solvent exemplified above to 1-chloro-3,3,3-trifluoropropene.
- the silicone compound can be applied to the surface without damaging the article made of.
- the solvent illustrated above can be mixed 1 type, or 2 or more types.
- the preferable composition ratio of each component is preferably adjusted in consideration of the solubility of the silicone compound and the ease of handling the solvent composition for the silicone compound (flammability, etc.).
- 1,1,2,2-tetrafluoro-1-methoxyethane HFE-254pc
- 40 to 80% by mass of 1-chloro-3,3,3-trifluoropropene is used as the mixing ratio.
- 1,1,2,2-tetrafluoro-1-methoxyethane HFE-254pc
- the mixing ratio if the mixing ratio of 1-chloro-3,3,3-trifluoropropene is larger than 80% by mass, the resin member such as acrylic or polycarbonate may be damaged. If the mixing ratio of 1-chloro-3,3,3-trifluoropropene is less than 40% by mass, the solubility in the silicone compound may be reduced.
- 1,1,1,3,3-pentafluorobutane HFC-365mfc
- the mixing ratio is 1 to 80% by mass of 1-chloro-3,3,3-trifluoropropene.
- 1,1,3,3-pentafluorobutane is preferably 40 to 20% by mass (see Example 4 described later).
- ⁇ Silicone compound coating solution> it uses as a silicone compound application
- silicone compound used in the present invention for example, various silicones used for surface coating can be used.
- straight silicone oils such as dimethyl silicone oil, methyl phenyl silicone oil, and methyl hydrogen silicone oil bonded with methyl, phenyl, and hydrogen atoms as substituents, and components derived secondarily from straight silicone oil
- modified silicone oils such as reactive silicone oils and non-reactive silicone oils.
- solvent composition for silicone compounds of this invention is easy to melt
- a reaction product of a reaction product of a copolymer of aminoalkylsiloxane and dimethylsiloxane a reaction product of an amino group-containing silane and an epoxy group-containing silane, and a polydiorganosiloxane containing a silanol group.
- a main component, a silicone mixture composed of a silicone containing polyaminoorganosiloxane with amino groups in the side chain or terminal, an amino group-containing alkoxysilane and an epoxy group-containing alkoxysilane, and a silicone having silanol groups at both ends are reacted. Examples thereof include a mixture of the obtained silicone and non-reactive silicone.
- the ratio of the silicone compound of the present invention in the coating silicone solution is preferably 0.1 to 80% by mass, particularly 1 to 20% by mass. If it is less than 0.1% by mass, it is difficult to form a coating film having a sufficient film thickness, and if it exceeds 80% by mass, it is difficult to obtain a coating film having a uniform film thickness.
- the silicone compound coating solution described above is applied to the surface of the article, and the silicone compound solvent composition such as 1-chloro-3,3,3-trifluoropropene is removed by evaporation to remove the silicone on the article surface.
- the silicone compound solvent composition such as 1-chloro-3,3,3-trifluoropropene is removed by evaporation to remove the silicone on the article surface.
- Form a film of the compound As an article to which the method of the present invention can be applied, it can be applied to various materials such as a metal member, a resin member, a ceramic member, and a glass member. It is preferable to apply to a spring, a spring part, etc.
- the needle tube portion of the injection needle when applied to the needle tube portion of an injection needle, etc., as a method of applying the silicone compound to the needle tube portion of the injection needle, the needle tube portion of the injection needle is immersed in the silicone compound coating solution and applied to the outer surface of the needle tube portion. Then, it is allowed to stand at room temperature or under heating to evaporate the solvent composition and form a silicone compound film.
- Silicon compound solubility test According to the following method, the solubility test of the silicone compound was performed using the solvent composition of the present invention.
- the silicone compound coating composition and the drying test were performed using the silicone compound solvent composition of the present invention.
- a silicone compound coating solution which is a mixture of the silicone compound solvent composition shown in Tables 1 to 5 and silicone oil, was applied to various stainless steel metal plates (SUS), and the drying property was evaluated. Moreover, the coating film after drying (natural drying) was confirmed visually and evaluated about applicability
- Example 1 (Examples 1-1 to 1-5) and Comparative Example 1-1
- Example 2 (Examples 2-1 and 2-2) and Comparative Example 2-1
- Example 3 (Examples 3-1 to 3-3) and Comparative Example 3-1
- Example 5 (Example 5-1) and Comparative Example 5-1
- Example 2-1 of Table 2 all five test samples (silicone oil addition amount: 0.1 g, 1 g, 5 g, 30 g, 80 g) showed the results of Table 2. Similarly, in each of the other examples, all five test samples gave the results in Tables 2-5.
- the flash point was measured using a tag sealed flash point tester (TAG-E type, manufactured by Yoshida Scientific Instruments).
- the flash point of a solvent composition for a silicone compound of 1-chloro-3,3,3-trifluoropropene and 1,1,2,2-tetrafluoro-1-methoxyethane was measured.
- HFE-254pc 1,1,2,2-tetrafluoro-1-methoxyethane
- the flash point was determined by mixing 1-chloro-3,3,3-trifluoropropene having no flash point with 254 pc having a flash point alone at an appropriate composition ratio. It can be seen that it can be used as a solvent composition for a silicone compound that is easy to handle. For example, it can be seen that when 1-chloro-3,3,3-trifluoropropene is added in an amount of about 30% by mass or more, the flash point is eliminated. Moreover, regarding the flash point, it can be seen that there is no significant difference between the cis body (1233Z) and the trans body (1233E).
- the flash point of a solvent composition for a silicone compound of 1-chloro-3,3,3-trifluoropropene and 1,1,1,3,3-pentafluorobutane was measured.
- the flash point was measured in the case of the cis form (1233Z).
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Abstract
Description
本発明のシリコーン化合物用溶剤組成物は、1-クロロ-3,3,3-トリフルオロプロペンを含むものである。
含フッ素不飽和炭化水素の一つである1-クロロ-3,3,3-トリフルオロプロペンは、二重結合を有するため、大気中のOHラジカルとの反応性が大きく、オゾン破壊係数(ODP)や地球温暖化係数(GWP)が著しく小さくなる。また、1-クロロ-3,3,3-トリフルオロプロペンは不燃性であり、不燃性かつ低GWPの特性を有する組成物である。
本発明において、シリコーン化合物を溶解させる溶剤として、1-クロロ-3,3,3-トリフルオロプロペンを単独でも使用できるが、用途によって、1-クロロ-3,3,3-トリフルオロプロペンに他の溶剤を添加することもできる。
本発明では、上述したシリコーン化合物用溶剤組成物とシリコーン化合物とを混合させることで、シリコーン化合物塗布溶液として使用する。本発明に使用されるシリコーン化合物としては、例えば、表面コーティング用に使用されている各種のシリコーンを使用することができる。
本発明においては、物品表面に上述したシリコーン化合物塗布溶液を塗布し、1-クロロ-3,3,3-トリフルオロプロペン等のシリコーン化合物用溶剤組成物を蒸発除去することにより、物品表面にシリコーン化合物の被膜を形成する。本発明の方法を適用できる物品としては、金属部材、樹脂部材、セラミックス部材、ガラス部材などの各種材質に適用することができ、特に、注射針の針管部や、ディスペンサー(液体定量噴出装置)のスプリングやバネ部分等に適用することが好ましい。
以下の方法に従い、本発明における溶剤組成物を用いてシリコーン化合物の溶解性試験を行った。
以下の方法に従い、本発明におけるシリコーン化合物用溶剤組成物を用いてシリコーン化合物の塗布試験及び乾燥性試験を行った。表1~表5に示すシリコーン化合物用溶剤組成物とシリコーンオイルとの混合物であるシリコーン化合物塗布溶液を各種ステンレス製の金属板(SUS)に塗布し、乾燥性を評価した。また、乾燥(自然乾燥)後の塗布膜を目視で確認し、塗布性について評価した。乾燥性および塗布性について表1~表5に表記した。
本発明におけるシリコーン化合物用溶剤組成物に関して、タグ密閉式引火点試験器(TAG-E型、吉田科学器械製)を用いて、引火点の測定を行った。
Claims (9)
- 1-クロロ-3,3,3-トリフルオロプロペンを含むシリコーン化合物用溶剤。
- (A)1-クロロ-3,3,3-トリフルオロプロペン、と、(B)1,1,2,2-テトラフルオロ-1-メトキシエタン、1,1,1,3,3-ペンタフルオロブタン、及び、1,1,2,2-テトラフルオロ-1-(2,2,2-トリフルオロエトキシ)エタンからなる群より選ばれる少なくとも1種からなる化合物を含む、シリコーン化合物用溶剤組成物。
- 1-クロロ-3,3,3-トリフルオロプロペン40~80質量%と1,1,2,2-テトラフルオロ-1-メトキシエタン60~20質量%からなる、請求項2に記載のシリコーン化合物用溶剤組成物。
- 1-クロロ-3,3,3-トリフルオロプロペン60~80質量%と1,1,1,3,3-ペンタフルオロブタン40~20質量%からなる、請求項2に記載のシリコーン化合物用溶剤組成物。
- 1-クロロ-3,3,3-トリフルオロプロペン70~80質量%と1,1,2,2-テトラフルオロ-1-(2,2,2-トリフルオロエトキシ)エタン30~20質量%からなる、請求項2に記載のシリコーン化合物用溶剤組成物。
- シリコーン化合物と、請求項1乃至請求項5の何れか1つに記載のシリコーン化合物用溶剤組成物とを含有するシリコーン化合物塗布溶液。
- 前記シリコーン化合物が、ストレートシリコーンであることを特徴とする請求項6に記載のシリコーン化合物塗布溶液。
- 請求項6又は請求項7に記載のシリコーン化合物塗布溶液を物品表面に塗布し、前記塗布溶液中のシリコーン化合物用溶剤組成物を蒸発除去することにより、物品表面にシリコーン化合物の被膜を形成させることを特徴とする、シリコーン化合物の塗布方法。
- 物品が金属又は樹脂であることを特徴とする請求項8に記載のシリコーン化合物の塗布方法。
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CN201080032010.3A CN102471638B (zh) | 2009-07-16 | 2010-07-09 | (聚)硅氧烷化合物用溶剂组合物 |
EP10799781.9A EP2455432B1 (en) | 2009-07-16 | 2010-07-09 | Solvent composition for silicone compound |
US13/378,553 US8846807B2 (en) | 2009-07-16 | 2010-07-09 | Solvent composition for silicone compound |
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JP2009167556 | 2009-07-16 | ||
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JP2009173950 | 2009-07-27 | ||
JP2010152586A JP5648345B2 (ja) | 2009-07-16 | 2010-07-05 | シリコーン化合物用溶剤組成物 |
JP2010-152586 | 2010-07-05 |
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JP2014529656A (ja) * | 2011-08-24 | 2014-11-13 | ハネウェル・インターナショナル・インコーポレーテッド | 低い環境影響を有する蒸発作用性材料 |
JP2018150548A (ja) * | 2011-08-24 | 2018-09-27 | ハネウェル・インターナショナル・インコーポレーテッドHoneywell International Inc. | 低い環境影響を有する蒸発作用性材料 |
JP2020158781A (ja) * | 2011-08-24 | 2020-10-01 | ハネウェル・インターナショナル・インコーポレーテッドHoneywell International Inc. | 低い環境影響を有する蒸発作用性材料 |
JP7042304B2 (ja) | 2011-08-24 | 2022-03-25 | ハネウェル・インターナショナル・インコーポレーテッド | 低い環境影響を有する蒸発作用性材料 |
JP2022078277A (ja) * | 2011-08-24 | 2022-05-24 | ハネウェル・インターナショナル・インコーポレーテッド | 低い環境影響を有する蒸発作用性材料 |
JP7408709B2 (ja) | 2011-08-24 | 2024-01-05 | ハネウェル・インターナショナル・インコーポレーテッド | 低い環境影響を有する蒸発作用性材料 |
US10815452B2 (en) | 2015-09-04 | 2020-10-27 | AGC Inc. | Solvent composition, cleaning method and method of forming a coating film |
US11401486B2 (en) | 2015-09-04 | 2022-08-02 | AGC Inc. | Solvent composition, cleaning method and method of forming a coating film |
WO2023122657A1 (en) | 2021-12-22 | 2023-06-29 | Rohm and Haas Electronic Materials (Shanghai) Ltd. | Coating composition for siliconization application |
Also Published As
Publication number | Publication date |
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EP2455432A1 (en) | 2012-05-23 |
EP2455432A4 (en) | 2012-12-26 |
US20120107513A1 (en) | 2012-05-03 |
US8846807B2 (en) | 2014-09-30 |
EP2455432B1 (en) | 2017-01-25 |
CN102471638B (zh) | 2014-12-10 |
CN102471638A (zh) | 2012-05-23 |
JP5648345B2 (ja) | 2015-01-07 |
JP2011046688A (ja) | 2011-03-10 |
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