WO1995010523A1 - Compose d'alcoxysilane, liquide de traitement de surface et lentille de contact - Google Patents

Compose d'alcoxysilane, liquide de traitement de surface et lentille de contact Download PDF

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Publication number
WO1995010523A1
WO1995010523A1 PCT/JP1994/001712 JP9401712W WO9510523A1 WO 1995010523 A1 WO1995010523 A1 WO 1995010523A1 JP 9401712 W JP9401712 W JP 9401712W WO 9510523 A1 WO9510523 A1 WO 9510523A1
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WO
WIPO (PCT)
Prior art keywords
surface treatment
group
contact lens
treatment liquid
alkoxysilane
Prior art date
Application number
PCT/JP1994/001712
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English (en)
Japanese (ja)
Inventor
Tuyoshi Miyazaki
Yasumi Koinuma
Original Assignee
Nof Corporation
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 Nof Corporation filed Critical Nof Corporation
Priority to JP51159295A priority Critical patent/JP3733593B2/ja
Publication of WO1995010523A1 publication Critical patent/WO1995010523A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/06—Phosphorus compounds without P—C bonds
    • C07F9/08—Esters of oxyacids of phosphorus
    • C07F9/09—Esters of phosphoric acids
    • C07F9/091—Esters of phosphoric acids with hydroxyalkyl compounds with further substituents on alkyl
    • C—CHEMISTRY; METALLURGY
    • C03—GLASS; MINERAL OR SLAG WOOL
    • C03C—CHEMICAL COMPOSITION OF GLASSES, GLAZES OR VITREOUS ENAMELS; SURFACE TREATMENT OF GLASS; SURFACE TREATMENT OF FIBRES OR FILAMENTS MADE FROM GLASS, MINERALS OR SLAGS; JOINING GLASS TO GLASS OR OTHER MATERIALS
    • C03C17/00—Surface treatment of glass, not in the form of fibres or filaments, by coating
    • C03C17/28—Surface treatment of glass, not in the form of fibres or filaments, by coating with organic material
    • C03C17/30—Surface treatment of glass, not in the form of fibres or filaments, by coating with organic material with silicon-containing compounds
    • C—CHEMISTRY; METALLURGY
    • C03—GLASS; MINERAL OR SLAG WOOL
    • C03C—CHEMICAL COMPOSITION OF GLASSES, GLAZES OR VITREOUS ENAMELS; SURFACE TREATMENT OF GLASS; SURFACE TREATMENT OF FIBRES OR FILAMENTS MADE FROM GLASS, MINERALS OR SLAGS; JOINING GLASS TO GLASS OR OTHER MATERIALS
    • C03C25/00—Surface treatment of fibres or filaments made from glass, minerals or slags
    • C03C25/10—Coating
    • C03C25/24—Coatings containing organic materials
    • C03C25/40—Organo-silicon compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
    • C07F7/1804—Compounds having Si-O-C linkages

Definitions

  • the present invention is used to hydrophilize the surface of various inorganic or organic materials, and is used in the fields of fibers, optical components, medical materials, diagnostic reagents, etc.
  • the present invention relates to an alkoxysilane compound useful as a protein adsorption control agent, a cell adhesion control agent, an antithrombotic agent, etc., and the surface hydrophilicity of various materials including the alkoxysilane compound and / or an acid-treated reactant thereof.
  • the present invention relates to a surface treatment liquid capable of improving the properties of the contact lens, and in particular, imparting a function such as a feeling of wearing, a protection property, and a fall prevention property to the contact lens, and a contact lens having a surface treated with the surface treatment liquid. .
  • a silane coupling agent having an alkoxysilane group has a surface modification because it has functions such as imparting hydrophobicity to the surface of an inorganic material or an organic material and easily introducing a reactive group. It is used as a filler.
  • an alkoxysilane compound that imparts hydrophilicity is not known.
  • betaine is known as a compound having excellent hydrophilicity.
  • US Pat. No. 3,671,502 discloses that N—methacryloyloxyshethyl-N, N—dimethyl-N- (3-sulfopropyl) ammonium betaine and Hi
  • the copolymer with hydroxyethylmethacrylate is more hydrophilic than poly (2-hydroxyhexylmethacrylate), which is known as a hydrophilic polymer.
  • poly (2-hydroxyhexylmethacrylate) which is known as a hydrophilic polymer.
  • none of these compounds has both an alkoxysilane group and a betaine group.
  • Japanese Patent Publication No. Sho 61-509918 discloses that a phosphatidylcholine group is introduced on the surface of a substance having a hydroxyl group as a compound for improving the biocompatibility surface. It describes how to do this.
  • This phosphatidylcholine group can exhibit excellent hydrophilicity, but has the disadvantage that it has poor hydrolysis resistance and poor long-term stability.
  • Conventional contact lenses include hard contact lenses, which are polymerized mainly with monomers such as methyl methacrylate, and butyl methacrylate.
  • a semi-contact lens that is polymerized as a polymer
  • a 2-contact lens that is polymerized mainly with a hydrophilic monomer such as 2-hydroxyhydrin methacrylate.
  • the node contact lens has superiority in hygiene because it is non-water-containing, but is necessary for good corneal metabolism and continuous wearing.
  • Semi-hard contact lenses have a certain degree of flexibility and are therefore excellent in wearing comfort, but have the problem of low oxygen permeability and lack of shape stability.
  • the soft contact lens is superior to a hard or semi-hard contact lens in terms of mounting properties because of its water content, There is a problem on the raw surface, and there are maintenance problems such as the need to sterilize by boiling every day.
  • Copolymers containing a methacrylate containing methacrylate and a methacrylate containing fluorine as main components have been proposed.
  • US Pat. No. 3,419,634 and US Pat. No. 3,196,335 propose silicone / polycarbonate copolymers.
  • these polymers having oxygen permeability have relatively high strength, they have problems in terms of wearability and wearing feeling.
  • An object of the present invention is to provide a novel material having both an alkoxysilane group and a betaine group, which can impart hydrophilicity to various materials and has excellent hydrolysis resistance after the application.
  • An object of the present invention is to provide an alkoxysilane compound.
  • Another object of the present invention is to improve the hydrophilicity of various material surfaces.
  • Still another object of the present invention is to provide a surface treatment liquid capable of providing a surface treatment layer having excellent hydrolysis resistance. Another object of the present invention is to provide an excellent wearing property and a feeling of wearing. An object of the present invention is to provide a contact lens provided with functions such as heat resistance, fall prevention, and the like.
  • R 1 and R 2 represent methino! S or etino 3 ⁇ 4, X represents -COO- or 1 S 0 3 _, and P and n represent 1-3 fiber, and q represents 0 Or
  • a surface treatment liquid containing the reactant is provided.
  • a contact lens surface-treated with the surface treatment liquid there is provided a contact lens surface-treated with the surface treatment liquid.
  • the alkoxysilane compound of the present invention is an alkoxysilane compound represented by the above general formula (I), and specifically, for example, N-propyl trimethoxysilane-N, N-dimethinole N 1- (3-Sulfopropyl) ammonium betaine, N-Provir trimethoxysilane N, N-Dimethyl N- (2-force ruboxicetyl) Ammonium betaine, N-Propyl methoxymethylsilane N, N-dimethyl N— (3—Sulfopropyl) ammonium betaine, N—Propyl ethoxymethylsilane N, N—Dimethyl N— (2—carboxyethyl) ammonium betaine, N—Provir trimethoxysilane N, N-dimethyl-N- (1-sulfomethyl) ammonium betaine, N-propyl methoxymethyl Lan-NN-Dimethyl-I), and specifically, for example, N-propyl
  • the above alkoxysilane compound is prepared.
  • a method of reacting an alkoxysilane compound having a dimethylamino group with a sulfon ring compound, a lactone ring compound or a monohalogenated carboxylic acid, or a method having the dimethylamino group Acrylic silane compound It can be easily prepared by, for example, a method of oxidizing after addition of ril.
  • alkoxysilane compound having a dimethylamino group examples include N, N-dimethyl-3-aminopropyltrimethoxysilane, N, N-dimethyl-3-aminoamino ""
  • Preferable examples include toxisilane, N, N-dimethyl-3-aminopropylmethylmethoxysilane, N, N-dimethyl-3-aminopropyltriethoxysilane and the like.
  • sultone ring compound examples include propane sultone 1,41-butane sultone.
  • lactone ring compound examples include 3-propyllactone, / 3-butyrolactone and the like.
  • Examples of the monohalogenated carboxylic acids include, for example, monochloroacetic acid, / 3-chloropropionic acid, etc.
  • an alkoxy group having a dimethylamino group The charged mole ratio of the silane compound to the sulfon ring compound, lactone ring compound or monohalogenated carboxylic acid, or the charged mole of the alkoxysilane compound having a dimethylamino group to the acrylonitrile The ratio is preferably 1: 0.5 to 10 and more preferably 1: 0.8 to 1.2.
  • the reaction is carried out in the presence of an organic solvent such as, for example, dried acetonitrile, methanol, ethanol, cross-linked form, and ethyl ether, preferably at a reaction temperature of 100 ° C. It is desirable to react at C to 120 for 30 minutes to 100 hours.
  • an organic solvent such as, for example, dried acetonitrile, methanol, ethanol, cross-linked form, and ethyl ether
  • reaction product when the resulting reaction product precipitates in the organic solvent, it may be filtered or dried to obtain a highly pure alcohol.
  • a lan compound can be obtained.
  • the obtained reaction product When the reaction proceeds in a homogeneous system throughout the reaction, the obtained reaction product may be used as it is, but it may be obtained by a known method such as recrystallization, reprecipitation, adsorbent treatment, column treatment, or distillation. It can be isolated and purified.
  • the alkoxysilane compound of the present invention is a novel compound having an alkoxysilane group and a betain group in the molecule, and has a used hydrophilicity and the like. It is useful as a surface modifier such as a protein adsorption control agent and a cell adhesion control agent.
  • the surface treating solution of the present invention contains the alkoxysilane compound represented by the general formula (I) and a compound of the formula (I) or an acid treatment reactant as essential components.
  • Preferred examples of the alkoxysilane compound include the compounds specifically listed above.
  • Examples of the acid-treated reactant include one of the alkoxysilane groups in the alkoxysilane compound. Examples thereof include a compound in which a part or all of the compound is converted to a highly active silanol group, and a condensate in which a compound converted to the silanol group is further condensed.
  • Such an acid treatment reactant is generated by adding an acid such as acetic acid, hydrochloric acid, sulfuric acid or the like to a surface treatment solution containing the alkoxysilane compound.
  • the amount of the acid to be added may be a desired amount for converting the above-mentioned alkoxysilane group to a silanol group, and is preferably 0.01 to 10% by weight based on the total amount of the surface treatment solution.
  • the surface treatment solution of the present invention further comprises, for example, sodium dodecylbenzenesulfonate and sodium dodecylsulfonate in addition to the essential components.
  • a surfactant such as an anionic surfactant such as tritium; a cationic surfactant such as cetylpyridyl dichloride; and a nonionic surfactant such as polyethylene glycol stearyl ether can also be contained.
  • the mixing ratio of the surfactant is preferably 1 mol or less per 1 mol of the alkoxysilane compound and / or its acid-treated reactant.
  • the surface treatment liquid of the present invention comprises a material containing the essential components, for example, ethanol, methanol, dimethylformamide, dimethylsulfoxide, tetrahydrofuran, 1,4-dioxane and the like. It can be prepared by diluting in an organic solvent, water or a mixture thereof.
  • the concentration of the alkoxysilane compound and Z or the acid treatment reactant in the surface treatment solution is not particularly limited, but is preferably 0.01 to 80% by weight, particularly preferably. 0.1 to 50% by weight. If the amount is less than 0.01% by weight, a sufficient hydrophilic effect cannot be obtained, while if it exceeds 80% by weight, the base material is a contact lens or the like. It is not preferable because basic physical properties such as oxygen permeability and mechanical strength of the contact lens may be impaired.
  • Examples of the substrate on which the surface treatment solution of the present invention can be fixed to perform surface treatment include, for example, a substrate material having a silanol group, a hydroxyl group, a carboxy group, or the like, or a substrate having many fine irregularities on the surface.
  • Materials that is, the surface of the organic polymer such as glass, ceramics and other inorganic polymers such as polypropylene, polyethylene, polyethylene terephthalate, polystyrene, polyvinyl chloride, and Teflon, etc. Resin treated by And others.
  • Examples of the base material include oxygen-permeable hard contact lenses, contact lenses such as soft contact lenses, and hemodialysis membranes. .
  • the surface can be efficiently modified.
  • the base material is a contact lens
  • at least the lens surface material is made of a material having a functional group capable of a condensation reaction with an alkoxysilane group or a silanol group.
  • Contact lenses specifically, resins containing silicone such as tris (trimethylsiloxy) silane groups, and hydroxyl groups such as 2-hydroxymethoxy acrylate
  • the contact lens include a resin, a resin having a carboxyl group such as methacrylic acid, or a resin having a mixed group thereof.
  • the surface treatment liquid can be fixed to the substrate by a method utilizing a silane coupling reaction to be described later, or the like.
  • the surface treatment liquid of the present invention improves the hydrophilicity of the surface of various base materials such as contact lenses, and particularly, in the case of contact lenses, improves the wearing property and the wearing feeling, and also improves the antifouling property. Functions such as safety and fall-off prevention can be provided. Further, the obtained surface treatment layer has excellent resistance to water decomposition, and the useful effect can be stably obtained for a long period of time.
  • the contact lens which has been subjected to a surface treatment on the lens surface and is not particularly limited as a contact lens serving as a base material includes, but is not limited to, the contact lenses specifically listed above. Preferably You can do it.
  • the surface treatment may be performed so that the surface treatment liquid adheres to the surface of the contact lens.
  • the contact lens is immersed in the surface treatment liquid or the surface treatment is performed.
  • a silane coupling reaction can be performed.
  • the silane coupling reaction is preferably carried out at a temperature of 0 to 250, especially 20 to 1 to 40, for 30 minutes to 100 hours, particularly for 1 to 24 hours. Desirable.
  • the contact lens after application of the surface treatment liquid is air-dried at about room temperature for 30 minutes to 24 hours. Further, it is preferable to wash with distilled water or the like after the reaction.
  • the contact lens to be surface-treated is preferably washed with an organic solvent such as a surfactant, acetone, methanol, or ethanol, and then the contact lens is known. It is desirable to pre-treat by acid treatment, alkaline treatment, plasma treatment, etc.
  • the thickness of the surface coat layer is preferably from 0.001 to LOOOA * m.
  • the contact lens of the present invention Since the surface of the contact lens of the present invention is treated with the surface treatment liquid, the contact lens has excellent characteristics and functions based on the surface treatment liquid stably for a long period of time.
  • N, N-Dimethinolay 3 Aminoprovir trimethoxysilane, instead of N, N-dimethyl-3-aminopropylmethyljetoxirane, and instead of prono and sodium sultone, / 3 —Reaction was performed according to Example 1 except that propiolactone was used, and N-propylpyroxymethylsilane-N, N-dimethyl-N— (2-nitrophenol) represented by the following structural formula was obtained. Got in. The yield was 99.4%. The results of each analysis are shown below. CH 3 CH 3
  • a 10% ethanol solution of each of the alkoxysilane compounds obtained in Examples 1 to 4 was applied to a glass plate, dried at room temperature, and then heat-treated for 120 hours for 1 hour.
  • a glass plate surface-treated with a lan compound was obtained.
  • the contact angle of the obtained glass plate surface was measured by a water drop method, the contact angle (20) of the glass plate before the treatment was 89 °, while the glass plate after the treatment was However, the angle was about 10 ° in each of the samples, indicating that an excellent hydrophilic surface was formed.
  • the presence or absence of nitrogen atoms on the surface of the surface-treated glass plate was measured using an X-ray photoelectron spectrometer (Shimadzu Corporation, SCAK-1). Further, after the surface treatment, the glass plate was immersed in 1 N hydrochloric acid for 24 hours, washed with distilled water, and similarly, the presence or absence of nitrogen atoms was measured.
  • the peak (402.5 eV) attributed to the fourth amine in the sulfobetaine group in the Nls binding energy region did not change before and after the hydrochloric acid treatment. That is, it was found that it had excellent hydrolysis resistance.
  • a phosphatidylcholine derivative was synthesized by the following method, and a surface treatment was similarly performed on a glass plate using the obtained derivative to evaluate hydrophilicity and hydrolysis resistance.
  • each contact after the surface treatment was about 10 °, and had excellent hydrophilicity as in the example.
  • the peak (40.5 eV) attributable to the quaternary amide in the phosphatidylcholine group in the binding energy region of N ls is indicated by the hydrochloric acid treatment. Previously observed, but not after treatment with hydrochloric acid. Therefore, it was found that the surface of the glass plate treated with the phosphatidylcholine derivative was poor in hydrophilicity, but poor in hydrolysis resistance.
  • the resin was cured by heating at 0 ° C for 6 hours to obtain a rod-shaped resin.
  • This resin was cut into a button with a thickness of 2 mm and the surface was polished to a mirror surface.
  • the button-shaped resin can be easily formed into a contact lens by a lace-cut method.
  • the obtained surface treatment solution is applied to a contact lens prepared from the above button-shaped resin, air-dried at room temperature for 30 minutes, and then heated at 90 ° C for 1 hour, and applied to the surface.
  • a contact lens having a surface coat layer with a thickness of 50 ⁇ was obtained.
  • the contact angle was measured to be 9 °, indicating that the contact lens had good hydrophilicity. I understood.
  • surface treatment was carried out in a physiological saline solution containing 0.4% by weight of albumin, 0.2% by weight of lysozyme and 0.1% by weight of globulin. Contact lenses were immersed and held for 35 and 17 days.
  • the contact lens was subjected to surface treatment in the same manner as in Example 5 using the obtained surface treatment solution, and the contact angle was measured to be 10 °. In addition, the protection was measured in the same manner. Table 1 shows the results.
  • N-Provir trimethoxysilane N, N-Dimethinole N- (3-sulfopropyl) ammonium betaine instead of N-propyl methoxymethylsilane synthesized in Example 3, N, N-dimethyl
  • the reaction was carried out according to Example 5 except that N- (2-sulfopropyl) ammonium betaine was used.
  • a surface treatment solution for contact lenses was prepared.
  • the contact lens was subjected to surface treatment in the same manner as in Example 5 using the obtained surface treatment solution, and the contact angle was measured. The result was 9 °.
  • the antifouling property was measured in the same manner. Table 1 shows the results.
  • N-Propyl trimethoxysilane N, N-dimethyl-N- (3-sulfopropyl) ammonium betaine instead of N-propyl methoxymethylsilane N, N-dimethyl-N
  • the reaction was carried out according to Example 5 except that (2-carboxyethyl) ammonium betaine was used, to prepare a surface treatment solution for contact lenses.
  • the contact lens was subjected to a surface treatment in the same manner as in Example 5 using the obtained surface treatment liquid, and the contact angle was measured to be 11 °.
  • the antifouling property was measured in the same manner. Table 1 shows the results.
  • Example 2 The N-propyltrimethoxysilane-NN-dimethyl-N- (3-sulfopropyl) ammonium betaine synthesized in Example 1 was dissolved in ethanol so as to have a concentration of 5% by weight. A surface treatment solution for lens was prepared.
  • the obtained surface treatment solution was applied to a contact lens prepared from the same button-shaped resin as in Example 5, air-dried at room temperature for 30 minutes, and then dried in an oven at 100 ° C for 4 minutes. Heating was carried out for a time to obtain a contact lens having a surface coat layer with a thickness of 50 m formed on the surface.
  • the obtained contact lens was immersed in distilled water for 24 hours. * After washing, the contact angle was measured to be 12 °. It was found to have good hydrophilicity. In addition, the water resistance was measured in the same manner as in Example 5. Table 1 shows the results.
  • Example 5 when the button-shaped resin was used as a contact lens and the contact angle was measured without performing surface treatment, it was found to be 86 °. In addition, the weather resistance was measured in the same manner. Table 1 shows the results. Protein (g c)

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Abstract

L'invention concerne un composé d'alcoxysilane représenté par la formule générale (I), un liquide de traitement de surface contenant ce dernier ou un produit de traitement acide de ce dernier, et une lentille de contact dont la surface est traitée avec ledit liquide de formule (I), dans laquelle R1 et R2 représentent indépendamment -CH¿3? ou -CH2H5; X représente -COO?-¿ ou -SO¿3?-; p et n représentent chacun un entier de 1 à 3; et q représente 0 ou 1, à condition que p+q=3. Ce composé peut conférer des propriétés entre autres hydrophiles à des surfaces constituées de divers matériaux de base et peut être utilisé dans les domaines de la fibre, des pièces optiques, du matériel médical, des médicaments diagnostiques de laboratoire etc.
PCT/JP1994/001712 1993-10-13 1994-10-13 Compose d'alcoxysilane, liquide de traitement de surface et lentille de contact WO1995010523A1 (fr)

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JP51159295A JP3733593B2 (ja) 1993-10-13 1994-10-13 コンタクトレンズ

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JP5/256070 1993-10-13
JP25607093 1993-10-13

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Cited By (10)

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EP0855372A1 (fr) * 1997-01-23 1998-07-29 Fraunhofer-Gesellschaft Zur Förderung Der Angewandten Forschung E.V. Méthode de hydrophilisation de substrats en verre et leur application
JP2000162556A (ja) * 1998-09-21 2000-06-16 Menicon Co Ltd 眼用レンズ材料およびその製法
KR20120092026A (ko) * 2011-02-10 2012-08-20 신에쓰 가가꾸 고교 가부시끼가이샤 아미노산 변성 실란 화합물 및 그의 제조 방법
CN101812086B (zh) * 2009-11-28 2012-12-26 深圳大学 一种抗菌化合物及其制备方法
JP2016074868A (ja) * 2014-10-06 2016-05-12 セントラル硝子株式会社 親水性被膜形成用薬液及び親水性被膜形成方法
WO2016167097A1 (fr) * 2015-04-15 2016-10-20 株式会社Kri Composé de silicium de bétaïne, procédé de production associé, composition liquide de revêtement hydrophile et film de revêtement
JP2016191053A (ja) * 2009-12-17 2016-11-10 スリーエム イノベイティブ プロパティズ カンパニー スルホネート官能コーティング及び方法
JP2017504709A (ja) * 2013-12-16 2017-02-09 スリーエム イノベイティブ プロパティズ カンパニー 洗剤及びすすぎ助剤組成物及び方法
JP2021046355A (ja) * 2019-09-17 2021-03-25 株式会社Kri 抗菌親水化剤
WO2023113031A1 (fr) * 2021-12-17 2023-06-22 Ａｇｃ株式会社 Filtre, procédé de production de filtre, matériau de revêtement, outil de capture de substance microscopique, dispositif de détection de substance microscopique, procédé de capture d'une substance microscopique, et composé

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CN104736650B (zh) * 2011-12-29 2017-09-29 3M创新有限公司 可清洁制品及其制备及使用方法
CN110776529A (zh) * 2019-06-17 2020-02-11 深圳市旭生三益科技有限公司 两性离子羧酸铵型硅烷偶联剂、硅氧烷环体及其制备方法
CN110776528A (zh) * 2019-06-25 2020-02-11 深圳市旭生三益科技有限公司 磺酸铵两性离子硅烷偶联剂、硅氧烷环体及其制备方法

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JPH05222064A (ja) * 1992-02-12 1993-08-31 Shin Etsu Chem Co Ltd 含けい素スルホベタイン化合物およびその製造方法
JPH05331455A (ja) * 1992-05-29 1993-12-14 Shin Etsu Chem Co Ltd 親水撥油処理剤

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JPH05222064A (ja) * 1992-02-12 1993-08-31 Shin Etsu Chem Co Ltd 含けい素スルホベタイン化合物およびその製造方法
JPH05331455A (ja) * 1992-05-29 1993-12-14 Shin Etsu Chem Co Ltd 親水撥油処理剤

Cited By (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0855372A1 (fr) * 1997-01-23 1998-07-29 Fraunhofer-Gesellschaft Zur Förderung Der Angewandten Forschung E.V. Méthode de hydrophilisation de substrats en verre et leur application
JP2000162556A (ja) * 1998-09-21 2000-06-16 Menicon Co Ltd 眼用レンズ材料およびその製法
JP4573376B2 (ja) * 1998-09-21 2010-11-04 株式会社メニコン 眼用レンズ材料およびその製法
CN101812086B (zh) * 2009-11-28 2012-12-26 深圳大学 一种抗菌化合物及其制备方法
JP2016191053A (ja) * 2009-12-17 2016-11-10 スリーエム イノベイティブ プロパティズ カンパニー スルホネート官能コーティング及び方法
US9567354B2 (en) 2011-02-10 2017-02-14 Shin-Etsu Chemical Co., Ltd. Amino acid-modified silane compounds and making method
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KR101888691B1 (ko) 2011-02-10 2018-08-14 신에쓰 가가꾸 고교 가부시끼가이샤 아미노산 변성 실란 화합물 및 그의 제조 방법
JP2017504709A (ja) * 2013-12-16 2017-02-09 スリーエム イノベイティブ プロパティズ カンパニー 洗剤及びすすぎ助剤組成物及び方法
JP2016074868A (ja) * 2014-10-06 2016-05-12 セントラル硝子株式会社 親水性被膜形成用薬液及び親水性被膜形成方法
WO2016167097A1 (fr) * 2015-04-15 2016-10-20 株式会社Kri Composé de silicium de bétaïne, procédé de production associé, composition liquide de revêtement hydrophile et film de revêtement
JPWO2016167097A1 (ja) * 2015-04-15 2018-02-08 株式会社Kri ベタイン系ケイ素化合物及びその製造方法並びに親水性コーティング組成液及びコーティング膜
JP2021046355A (ja) * 2019-09-17 2021-03-25 株式会社Kri 抗菌親水化剤
WO2023113031A1 (fr) * 2021-12-17 2023-06-22 Ａｇｃ株式会社 Filtre, procédé de production de filtre, matériau de revêtement, outil de capture de substance microscopique, dispositif de détection de substance microscopique, procédé de capture d'une substance microscopique, et composé

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