WO2001081474A1 - Composition anti-salissure a base de silicone - Google Patents

Composition anti-salissure a base de silicone Download PDF

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Publication number
WO2001081474A1
WO2001081474A1 PCT/JP2001/003292 JP0103292W WO0181474A1 WO 2001081474 A1 WO2001081474 A1 WO 2001081474A1 JP 0103292 W JP0103292 W JP 0103292W WO 0181474 A1 WO0181474 A1 WO 0181474A1
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WO
WIPO (PCT)
Prior art keywords
group
formula
silicone
och
silicone composition
Prior art date
Application number
PCT/JP2001/003292
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English (en)
Japanese (ja)
Inventor
Akira Chida
Kayoko Honda
Yasushi Yonei
Katsuhiko Imoto
Susumu Wada
Haruhiko Mohri
Original Assignee
Daikin Industries, Ltd.
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Daikin Industries, Ltd. filed Critical Daikin Industries, Ltd.
Publication of WO2001081474A1 publication Critical patent/WO2001081474A1/fr

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Classifications

    • 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
    • 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
    • C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
    • C09D175/04—Polyurethanes
    • 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

  • a represents 0 or 1 to 6 in terms of surface concentration, water decomposition, and desorption. It is an integer of 2 to 4, and preferably an integer of 2 to 4.
  • b is an integer of 0 or 1 to 5 in terms of surface density and hydrophilicity, and is preferably an integer of 0 to 1, and
  • c is a surface density. It is an integer of 0 or 1 to 6, and preferably an integer of 0 to 3 from the viewpoint of shrinkage, water-decomposability and desorption.
  • hydrolytic decomposition and surface hydrophilicity are obtained. It is preferable because of its superiority.
  • X is a hydrogen atom, or an oxygen atom, a nitrogen atom, a fluorine atom, and the like as described in (i) to (iii) below. It is a monovalent organic group having 1 to 5000 carbon atoms which may contain a chlorine atom.
  • CH 2 C CH 3 co 2 CH 2 3 Si ⁇ COCF 3 ) 2 (OCH 3 ),
  • the content of the fluorine atom in the organic metal compound represented by the formula (X) is at least 5% by weight, preferably 15 to 60% by weight. Heavy By having the amount%, it is possible to obtain, for example, an effect of excellent surface concentration and reproducibility of surface hydrophilization.
  • Luganopolysiloxane Formula (V):
  • the organosiloxane-containing polymer used in the present invention is: Depending on the type of A in the formula (I), the following three types or mixtures thereof are included.
  • the content of the unit of the formula (III) is 50 mol% or more, preferably 50 to 98 mol%, and more preferably 60 to 98 mol%. If it is less than 50 mol%, various durability such as skin formation, heat resistance, weather resistance, chemical resistance, and water resistance will be reduced.
  • Silicone polymer containing polyether chain Includes silicone-based polymer containing ether bond (_ ⁇ —C-1) It is.
  • the viscosity of the polymer S is 25 to 500,000 cst at 25 ° C, and more preferably 100 to 100: 100 cst.
  • silicone-based elastomers that are hardy (liquids before hardening).
  • one-part or two-part room temperature hardening (RTV) elastomers are particularly preferred.
  • RTV elastomers include, for example, acetic acid-type, alcohol-free type, oxidized type, deamidated type, and deaminated type.
  • Use any type of condensed type such as amide type, deaminoxine type, deaceton type, dehydrogenated type, dewatered type, etc., as well as additional types.
  • it can be used, it is particularly preferable to use a deacetic acid type, a de-alcohol type, a de-oxidized type, an acetate type or an addition type.
  • the solvent may or may not be used.
  • the solvent may be appropriately added according to the intended use.
  • Non-fluorine-based organic solvents include, for example, aromatic carbohydrate-based solvents such as xylene and toluene; Solbesso 100, Solbes Aliphatic hydrocarbon solvents such as vesso 150, hexane, etc .; methyl acetate, ethyl acetate, butyric acetate, ethylene glycol monomonoacetate Methyl ether, ethylenic acetate alcohol monoethyl ether, ethyl acetate, alcoholic alcohol monoethyl ether, acetic acid Diethylene glycol monomethyl ether, diethylene glycol acetate methyl alcohol monoterylate, diethylene glycol acetate Cole monobutyrate, acetate Esters such as polyethylene glycol, diethyl alcohol acetate, etc .; dimethyl ether, dimethyl ether, diethylene glycol, etc .; Butyl ether, ethylene glycol monomethyl ether, ethyl glyco
  • Suitable defoaming agents include, for example, Zeffle GH-200 (manufactured by Daikin Industries, Ltd.), a long-chain fluoroalkyl-modified alkyl group.
  • Siloxane-based antifoaming agents such as xan, and fluorosilicone such as FA-600 and FS-1265 (both manufactured by Shin-Etsu Chemical Co., Ltd.) Examples include silicone-based antifoaming agents, silicone compound-based antifoaming agents, silicone-based antifoaming agents, and acrylic-based antifoaming agents.
  • a known repellent that prevents the access of aquatic organisms without releasing harmful substances such as heavy metals is used as a solid in the polymer (a). 50 parts or less per 100 parts of form, preferably 0.05 to 50 parts may be added.
  • Such biological repellents have the formula:
  • X is H or a halogen atom, preferably C1, Br or F
  • a nitrogen-containing amide-type repellent represented by the formula:
  • Coatings or films formed with the composition of the present invention have a high degree of lipophilicity on the surface easily, and also adhere to lipophilic stains. It is possible to achieve the antifouling adhesion property without having to do so.
  • it has weather resistance, chemical resistance, optical properties (such as transparency), mechanical properties (strength, elongation), adhesion to base materials, heat resistance, It excels in heat resistance and yellowing.
  • the composition may be used in the same manner as ordinary hardening compositions, such as building materials, interior materials, and other indoor or building materials, vehicles, airplanes, and ships.
  • a paint for outdoor use such as exterior equipment, ship bottoms, electric vehicles, etc., directly, or directly, to metal, concrete, plastic, etc.
  • Layered paints such as primers, paints, epoxy resins, acrylic resin paints, polyester resin paints, etc. And can be done. It can also be used as a sealing agent.
  • the film thickness is suitably from 1 to 500 ⁇ , preferably from 5 to 150 m.
  • the base material is a plastic base material
  • the base material used for the metal base material, the cement base material, and the undercoat paint and the intermediate coating material are applied. After mounting, the paint composition of the present invention can be applied.
  • the present invention can provide easily drainable goods.
  • water does not accumulate on the surface or adhere to water droplets, and the water spreads evenly on the surface to form a water film. . Therefore, scales and oily stains do not adhere to streaks or spots, and can be easily removed only by flowing clean water.
  • structures include not only fixed-type structures such as piers and waterways, but also structures that mainly move such as ships.
  • Underwater structures such as piers, concrete blocks, wave-dissipating blocks, breakwaters, etc .;
  • Ship structures or accessories such as the draft or bottom of the ship, the exterior of the submarine, screws, propellers, anchors, etc.
  • AM-712 treated aluminum plate is sprayed with Shin-Etsu Kagaku Kogyo Co., Ltd. silicone primer (Primer C). and Ri under coating and painting Mr. dried (dry film thickness 20 ⁇ ⁇ ).
  • the silicone resin composition obtained above was applied on the undercoating film in the evening, cured at room temperature for 1 hour, and then cured. 80 ° C After drying for 20 minutes, a coated plate (dry film thickness: 25 ⁇ m) for the test was prepared.
  • the lightness before and after the exposure was measured with a color difference meter (CR-300, manufactured by Minoru Yu Co., Ltd.) (10 points per sample, on a blank sheet of paper).
  • the value obtained by dividing the average brightness before exposure from the average brightness after exposure is defined as the average brightness difference.
  • the coated plate used for the coating film hydrophilicity test (after exposure for 14 days at 30 ° on the south side) was washed with water and then air-dried at room temperature.
  • carbon black As a carbon contamination standard material, carbon black (MA-100, manufactured by Mitsubishi Chemical Co., Ltd.) should be adjusted to a concentration of 8% in water. Using the dispersed aqueous dispersion, the standard carbon soiled aqueous dispersion was sprayed on the test piece, and then dried with a hot air dryer at 60 ° C. Time processing and forcibly attach the carbon. After that, it is washed in running water using a brush, and the difference in brightness before and after washing and the remaining degree of carbon after washing are examined.
  • MA-100 manufactured by Mitsubishi Chemical Co., Ltd.
  • test coated plate is cut into 80 mm width and 80 mm length, and a lipophilic coating is applied to the mouth of a glass bottle (inner diameter 60 mm, depth 70 mm) containing 100 ml of pure water. Make sure that it faces the inside of the device.
  • This bottle was immersed in hot water at a temperature of 40 ° C (tilt angle: about 22 degrees), left for 30 minutes, and then visually checked for cloudiness on the surface using the following criteria. evaluate .
  • Cloudy and water droplets are recognized in the area of less than 10% of the mouth of the bottle.
  • ⁇ Cloudy and water droplets are recognized in the area of 10 to 40% (less than) of the mouth of the bottle. .
  • X Water droplets are observed in an area of 70% or more of the mouth of the bottle. (Condensation prevention) Attach each test piece to the vertical surface of the above-mentioned easy-to-use agricultural housing, and in winter (January-February) at 5:00 a.m. Observe the condition of the wall surface visually (condensation on the inner wall surface). In addition, the ion-exchange water is sprayed on the inner wall surface with a house spray, and the water wettability can be visually inspected (mist spray wettability). The evaluation is performed at each stage.
  • Silicone-based polymer a—2
  • Silicone-based polymer a—5
  • Silicone-based polymer a_7
  • R is CH 3 and CH 2 C 2 in the formula (XI) as a hydrophilizing agent.
  • R is CH 3 and CH 2 CF 2 C in formula (XI) as a hydrophilizing agent.
  • FHCF 3 and CH 2 CF 2 CFHCF 3 Z CH 3 Specific use of 0.5 (hereinafter referred to as “hydrophilizing agent D”) was used.
  • the compositions were prepared in the same manner as in Examples 1 to 8 (however, in Examples 29 to 32, the surface conditioning agent G was used as the surface conditioning agent). The composition is shown in Table 7). This composition was applied in the same manner as in Example 1 to an aluminum plate that had been subjected to a heat treatment treatment with Norco overnight to prepare a test coating plate.
  • Example 1 the compositions were prepared in the same manner as in Examples 1 to 8, respectively, with no addition of a hydrophilizing agent.
  • the surface conditioner G was used as the surface conditioner, and the composition is shown in Table 11). In the same manner as in Example 1, this composition was applied to a chemically treated aluminum plate with Barco overnight to produce a test coated plate.
  • Example 14 The same test as in Example 1 was performed on this test sheet. The results are shown in Table 14.
  • Silicone Elastomer (Chirant 40 manufactured by Shin-Etsu Chemical Co., Ltd.). Solvent-free sealant.
  • Silicone polymer a— 12 :
  • Silicone Elastomer (a pure-silant manufactured by Shin-Etsu Chemical Co., Ltd.). Solvent-free sealant.
  • Silicone Elastoma Co., Ltd. (Shinetsu Chemical Industry Co., Ltd. Co., Ltd., Co., Ltd., 300) Solvent-free sealant.
  • Silicon Elastomer (X-311-1657 manufactured by Shin-Etsu Chemical Co., Ltd.). Antibacterial sealant.
  • Silicone polymer a-16
  • Silicone polymer a-17
  • Dry wiping method ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ Flowing method ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ Antistatic property (Surface resistance value) ( X101 ⁇ )
  • Example 4 In Examples 41 to 49, the silicone-based polymer used in each of Examples 41 to 41 was replaced by the lyophilic agent C instead of the lyophilic agent A.
  • a sealant was prepared in the same manner as in Examples 49 to 49 (the composition is shown in Table 15), and the sealant was kneaded and hardened in the same manner as in Example 41. The test sheet was made.
  • the hydrophilizing agent E was used in place of the hydrating agent A to obtain a hydrolytic catalyst ( Aluminium D made by Fine Chemical Co., Ltd. was added to a PHR with 1 PHR. [1] The same as in Examples 41 to 49, respectively.
  • a sealant was prepared (the composition is shown in Table 19), and the sealant was kneaded and hardened in the same manner as in Example 41 to obtain a test sheet. It was made.
  • Dry wiping method ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ Flowing water method ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ Antistatic property (Surface resistance value) ( X101 ⁇ )
  • Example 41 to 49 the sealant was prepared in the same manner as in Examples 41 to 49, except that the lyophilic agent was not added to the water. (The composition is shown in Table 21). This sheet was kneaded and hardened in the same manner as in Example 41 to produce a test sheet.
  • This compound was rolled with a spatula to form a sheet with a thickness of about 2 mm, left at room temperature for 2 hours, and then at 150 ° C for 30 minutes. Heat treatment was performed to produce a test sheet.
  • Silicon Elastomer (KE1 manufactured by Shin-Etsu Chemical Co., Ltd.) 950). Molding materials.
  • Silicone polymer a-20
  • Silicon Elastomer (KE1 990-40 manufactured by Shin-Etsu Chemical Co., Ltd.). Molding materials.
  • Silicone polymer a-21
  • Silicon gel (X-32-1342 manufactured by Shin-Etsu Kagaku Kogyo Co., Ltd.) A molding material.
  • Silicone polymer a- 22 :
  • Silicone polymer a- 23 :
  • Silicone Elastomer (X- 30-2776U manufactured by Shin-Etsu Chemical Co., Ltd.). Conductive rubber material.
  • Silicone polymer a— 24
  • Silicon Elastomer (X-32-1346 manufactured by Shin-Etsu Chemical Co., Ltd.). Molding material.
  • Silicon Elastomer (X-32- 1709 manufactured by Shin-Etsu Chemical Co., Ltd.). Material for vacuum injection.
  • the hydrophilizing agent is preliminarily added to the exclusive hardener solution, and this is added to the silicone gel. D. Then, it was poured into a mold and allowed to harden at room temperature for 2 hours and then at 150 ° C for 30 minutes to produce a sheet-like test piece.
  • a hydrophilic agent and an additive are mixed with the silicone oligomer and a primer is applied. Spray coated aluminum sheet, cured for 2 hours at room temperature, and then cured for 3 days at room temperature to produce a test coated plate.
  • Dry wiping method ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ Flowing water method ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ Antistatic property (Surface resistance value) ( X10 1 ⁇ )
  • Example 77 to 83 For the silicone-based polymer used in Examples 77 to 83, the use of the hydrating agent C in place of the hydrating agent A was carried out, respectively.
  • a composition was prepared in the same manner as in Examples 77 to 83 (the composition is shown in Table 25), and a sample was prepared in the same manner as in Examples 77 to 83 using the composition. Was made.
  • Example 77 to 83 the use of no lyophilizing agent was the same as in Examples 77 to 83, respectively.
  • a composition was prepared in the same manner (the composition is shown in Table 29), and a test sample was prepared from this composition in the same manner as in Examples 77 to 83.
  • a sealant having the composition shown in Table 31 was prepared in the same manner as in Example 41. This sealant was constructed at the joint of the outer wall of a house in Osaka City, Japan, and was exposed for 12 months, followed by the same procedure as in Example 1. The joints were tested for low-contamination adhesion and easy-cleaning. The results are shown in Table 31.
  • silicone weight is excellent in ease of cleaning, easy drainage, anti-fog, anti-condensation, anti-static, bio-compatibility, etc.

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  • 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)
  • Paints Or Removers (AREA)

Abstract

Cette invention concerne une composition à base de polymère de silicone comprenant un polymère de silicone et un agent hydrophilisant qui renferme un composé organométallique avec groupe hydrolysable éliminable, un oligomère de ce composé et/ou un co-oligomère d'au moins deux composés organométalliques de ce type. Cette composition est remarquable en termes de nettoyage, de facilité d'écoulement, de prévention de la condensation de la rosée, de propriétés antistatiques, de biocompatibilité. Est également décrit un article moulé.
PCT/JP2001/003292 2000-04-20 2001-04-17 Composition anti-salissure a base de silicone WO2001081474A1 (fr)

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JP2000-120088 2000-04-20
JP2000120088 2000-04-20

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Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2004360039A (ja) * 2003-06-06 2004-12-24 Konica Minolta Holdings Inc 薄膜形成方法及び薄膜形成体
JP2005023381A (ja) * 2003-07-03 2005-01-27 Konica Minolta Holdings Inc 薄膜形成方法、薄膜形成装置及びそれを用いて作製した薄膜形成体
JP2005171100A (ja) * 2003-12-11 2005-06-30 Daikin Ind Ltd ミクロ相分離構造形成剤
WO2006077751A1 (fr) * 2005-01-19 2006-07-27 Daikin Industries, Ltd. Composition de revêtement faiblement teintant et film de revêtement faiblement teintant produit à partir de celle-ci
JP2006291045A (ja) * 2005-04-11 2006-10-26 Ricoh Co Ltd エレクトレットおよびその製造法
JP2007520588A (ja) * 2003-12-05 2007-07-26 バイオシグナル リミテッド 抗微生物性化合物と表面およびポリマーとの結合
WO2008044765A1 (fr) * 2006-10-12 2008-04-17 Daikin Industries, Ltd. Composition de polymère fluoré durcissable
JP2010121111A (ja) * 2008-10-23 2010-06-03 Mie Univ ポリオルガノシロキサン組成物およびその硬化体
US20160024314A1 (en) * 2013-03-20 2016-01-28 Hempel A/S Novel polysiloxane-based fouling control coating systems
CN111448267A (zh) * 2017-12-14 2020-07-24 阿克佐诺贝尔国际涂料股份有限公司 污损脱附涂料组合物、涂有此涂料组合物的基材及此涂料组合物的用途
JPWO2019139171A1 (ja) * 2018-01-12 2021-01-14 日東電工株式会社 水生生物付着防止用フィルム
JPWO2019139170A1 (ja) * 2018-01-12 2021-01-14 日東電工株式会社 水没型センサーユニット
JP2021021733A (ja) * 2020-08-04 2021-02-18 岡山ガード工機有限会社 水中物質及び水生生物の付着を許さない量水標。

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JP4506104B2 (ja) * 2003-06-06 2010-07-21 コニカミノルタホールディングス株式会社 薄膜形成方法
JP2004360039A (ja) * 2003-06-06 2004-12-24 Konica Minolta Holdings Inc 薄膜形成方法及び薄膜形成体
JP2005023381A (ja) * 2003-07-03 2005-01-27 Konica Minolta Holdings Inc 薄膜形成方法、薄膜形成装置及びそれを用いて作製した薄膜形成体
JP4506112B2 (ja) * 2003-07-03 2010-07-21 コニカミノルタホールディングス株式会社 薄膜形成方法及び薄膜形成装置
JP2007520588A (ja) * 2003-12-05 2007-07-26 バイオシグナル リミテッド 抗微生物性化合物と表面およびポリマーとの結合
JP2005171100A (ja) * 2003-12-11 2005-06-30 Daikin Ind Ltd ミクロ相分離構造形成剤
WO2006077751A1 (fr) * 2005-01-19 2006-07-27 Daikin Industries, Ltd. Composition de revêtement faiblement teintant et film de revêtement faiblement teintant produit à partir de celle-ci
JP2006291045A (ja) * 2005-04-11 2006-10-26 Ricoh Co Ltd エレクトレットおよびその製造法
US9127114B2 (en) 2006-10-12 2015-09-08 Daikin Industries, Ltd. Curable fluorine-containing polymer composition
WO2008044765A1 (fr) * 2006-10-12 2008-04-17 Daikin Industries, Ltd. Composition de polymère fluoré durcissable
JP2010121111A (ja) * 2008-10-23 2010-06-03 Mie Univ ポリオルガノシロキサン組成物およびその硬化体
US20210261793A1 (en) * 2013-03-20 2021-08-26 Hempel A/S Novel polysiloxane-based fouling control coating systems
US20160024314A1 (en) * 2013-03-20 2016-01-28 Hempel A/S Novel polysiloxane-based fouling control coating systems
US11787953B2 (en) 2013-03-20 2023-10-17 Hempel A/S Polysiloxane-based fouling control coating systems
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