EP3174843A1 - Tensioactifs fluorés - Google Patents

Tensioactifs fluorés

Info

Publication number
EP3174843A1
EP3174843A1 EP15738275.5A EP15738275A EP3174843A1 EP 3174843 A1 EP3174843 A1 EP 3174843A1 EP 15738275 A EP15738275 A EP 15738275A EP 3174843 A1 EP3174843 A1 EP 3174843A1
Authority
EP
European Patent Office
Prior art keywords
compounds
independently
formula
formulas
same
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Withdrawn
Application number
EP15738275.5A
Other languages
German (de)
English (en)
Inventor
Reiner Friedrich
Gerhard Jonschker
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Merck Patent GmbH
Original Assignee
Merck Patent GmbH
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 Merck Patent GmbH filed Critical Merck Patent GmbH
Publication of EP3174843A1 publication Critical patent/EP3174843A1/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
    • C07C41/01—Preparation of ethers
    • C07C41/02—Preparation of ethers from oxiranes
    • C07C41/03—Preparation of ethers from oxiranes by reaction of oxirane rings with hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
    • C07C213/02—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions involving the formation of amino groups from compounds containing hydroxy groups or etherified or esterified hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
    • C07C217/02—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
    • C07C217/04—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
    • C07C217/28—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having one amino group and at least two singly-bound oxygen atoms, with at least one being part of an etherified hydroxy group, bound to the carbon skeleton, e.g. ethers of polyhydroxy amines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
    • C07C217/02—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
    • C07C217/04—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
    • C07C217/28—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having one amino group and at least two singly-bound oxygen atoms, with at least one being part of an etherified hydroxy group, bound to the carbon skeleton, e.g. ethers of polyhydroxy amines
    • C07C217/40—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having one amino group and at least two singly-bound oxygen atoms, with at least one being part of an etherified hydroxy group, bound to the carbon skeleton, e.g. ethers of polyhydroxy amines having at least two singly-bound oxygen atoms, with at least one being part of an etherified hydroxy group, bound to the same carbon atom of the carbon skeleton, e.g. amino-ketals, ortho esters
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
    • C07C41/01—Preparation of ethers
    • C07C41/05—Preparation of ethers by addition of compounds to unsaturated compounds
    • C07C41/06—Preparation of ethers by addition of compounds to unsaturated compounds by addition of organic compounds only
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
    • C07C41/01—Preparation of ethers
    • C07C41/16—Preparation of ethers by reaction of esters of mineral or organic acids with hydroxy or O-metal groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
    • C07C41/01—Preparation of ethers
    • C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
    • C07C41/26—Preparation of ethers by reactions not forming ether-oxygen bonds by introduction of hydroxy or O-metal groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/02—Ethers
    • C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
    • C07C43/04—Saturated ethers
    • C07C43/13—Saturated ethers containing hydroxy or O-metal groups
    • C07C43/137—Saturated ethers containing hydroxy or O-metal groups containing halogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/02—Ethers
    • C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
    • C07C43/14—Unsaturated ethers
    • C07C43/17—Unsaturated ethers containing halogen
    • 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
    • C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
    • C09D7/40—Additives
    • C09D7/45—Anti-settling agents
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
    • C09J11/02—Non-macromolecular additives
    • C09J11/06—Non-macromolecular additives organic
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/004—Surface-active compounds containing F

Definitions

  • the present invention relates to novel compounds having fluorinated end groups, their use as surface-active
  • Fluorosurfactants are used in various applications and have e.g. for improved wetting of surfaces. So they are e.g. used as an interface mediator or emulsifier or viscosity reducer in paints, varnishes or adhesives.
  • Fluorine-containing nonionic surfactants are usually based on fluorinated alkyl chains and hydrophilic polyethylene glycol units. Due to the chain length of 6 to 8 carbon atoms of the perfluorinated portion, such surfactants are potentially bioaccumulating, persistent and toxic. Shorter perfluorinated alkyl chains of 2-5 carbon atoms are known to be less toxic and bioaccumulating, but have inadequate activity.
  • JP-A-2001/133984 discloses surface-active compounds with
  • Perfluoroalkoxy chains are known which are suitable for use in antireflection coatings.
  • JP-A-09/111286 discloses the use of perfluoropolyether surfactants in emulsions.
  • WO 2006/072401 and WO 2010/003567 surface-active compounds with
  • Fluoroalkyl groups are described in US 7,635,789, US 7,737,307, US 2008/0093582, JP 2004-18394 and WO 2010/002623.
  • the compound CF3-CF2-CF2-O-CH2-CH2-OH is known (CAS 1313023-37-8) and in J. of Supercritical Fluids 55 (2010) 802-816 are theoretical investigations on mixtures of CO2 and perfluoroalkyl surfactants in aqueous solutions described.
  • WO 03/010128 perfluoroalkyl substituted amines, acids, amino acids and thioether acids
  • Break down compounds or preferably as effective in lower dosage as conventional fluorosurfactants are preferably as effective in lower dosage as conventional fluorosurfactants.
  • a first subject of the present invention are compounds of the formula (I)
  • R is H, alkyl, -OH or -CH 2 -O-A "'a - R f",
  • Rf, Rf and Rf are the same independently CF3 -CF2-CF2-O-CF (CF 3) -CH 2, or CF 3 - (CF2) n- (CH2) m- are
  • R 1 - R 4 are each independently hydrogen or a C1-C4
  • R ' H or linear or branched alkyl
  • X is H or linear or branched alkyl.
  • n 1-5.
  • m 1-3.
  • R is H or OH.
  • B is O, CH 2 -O or CH 2 NR ', where R' is preferably H or CH 3, especially H.
  • o and / or p are 1-4, in particular 1-2.
  • Preference is q 1-100, in particular 1-40, particularly preferably 1-20, in particular 5-18.
  • t is preferably 0.
  • the group comprises ((CR 1 R 2 ) 0 - (CR 3 R 4 ) P O) q Polyethylene, polypropylene, polyisobutylene and / or polybutylene glycol units.
  • A, A 'and A can also be -O-CH 2 -CHR" -, with R "being H or CH 3.
  • X is preferably H or CH 3.
  • Rf, Rf and Rf are the same and / or A, A 'and A" are the same.
  • Particularly advantageous compounds of the formula (I) are those in which one or more of the variables have the preferred meanings.
  • Particularly advantageous compounds of the formula (I) in which all the variables mentioned at the same time have the preferred, in particular the particularly preferred, meanings.
  • Particular preference is given here to compounds according to claims 2 and 3.
  • Rf and Rf CF3-CF2-CF2-O-CF (CF 3) -CH 2, C2F5-C3F7-CH2- CH2- or are
  • R is H or OH
  • B is O or CH 2 -NR ⁇ with R 'being H or CH 3 ,
  • Polypropylene glycol unit is,
  • q is 1-40, preferably 1-20, in particular 5-18,
  • Rf and Rf are the same.
  • Preferred compounds of the invention are in the formula (P)
  • Particularly advantageous compounds of the formula ( ⁇ ') are those in which all the variables mentioned at the same time have the meanings described for formula (I), in particular the particularly preferred meanings.
  • R H or -OH
  • B O, CH 2 -O or CH 2 -NR '
  • R' H, Chh or C 2 H 5
  • X H or alkyl, preferably Chh or C2H5
  • the group ((CR 1 R 2 ) 0 - (CR 3 R 4 ) P O) q with q 1-40, preferably 1-20, in particular 5-18, a polyethylene,
  • Polypropylene, polyisobutylene and / or polybutylene glycol unit preferably a polyethylene or polypropylene glycol unit.
  • Preferred compounds are those of the formulas (II), (IIIa) / (IIIb) and (IVa) / (IVb), in particular (IVa):
  • the new compounds preferably correspond to the formulas (IIa), (IIb), (IIIa-1) and (IVa-1):
  • the compounds of the formula (I) according to the invention can be prepared by simple, conventional process steps and starting from commercial starting materials, for. Example, via the intermediates of the formulas (VI) or (VII):
  • Alkylenoxidpolymerisation eg ethylene oxide or Propylene oxide
  • nonionic surfactants of the formula (II ') are converted to the corresponding nonionic surfactants of the formula (II ').
  • the execution of said processes is familiar to the person skilled in the art (US Pat. No. 5,567,857;
  • the alcohols of the formulas (Va) and (Vb) can also be reacted by reaction with 3-chloro-2-chloromethyl-1-propene to give the branched structures of the formula (VII ') where Rf is the same as the corresponding fluoro-containing groups of the formulas ( Va) or (Vb).
  • the compounds of formula (VII ') can then via the epoxide as an intermediate by reaction with polyethylene glycols or
  • the invention also provides the compounds of the formulas (VI) and (VII) or of the formulas (VI ') and (VII') which can be prepared as described, where the variables are those described for formula (I), especially the preferred meanings.
  • a preferred subject of the invention are the compounds of the formulas (VI ') and (VII').
  • the alcohols used are commercially available and / or their
  • the new compounds may have low environmental toxicity and good surface activity at the same time.
  • the compounds according to the invention preferably have a particular surface activity.
  • the compounds of the formula of the invention preferably have a particular surface activity.
  • a further subject of the present invention is the use of the compounds according to the invention and the preferred embodiments described above as surfactants,
  • Fluorosurfactants of the formula ( ⁇ '), in particular of the formulas (II), (III) and (IV), are preferably used, in particular the abovementioned particularly preferred
  • the mixtures according to the invention may also contain solvents, additives, auxiliaries and fillers and non-fluorinated surfactants.
  • solvents include silicone particles, plasticizers and surface-modified pigments.
  • Preferred fields of use are, for example, the use of the fluorosurfactants according to the invention as additives in surface coating preparations, such as paints, varnishes, protective coatings,
  • Specialty coatings in electronic or semiconductor applications e.g., photoresists, top anti-reflective coatings, bottom anti-reflective coatings
  • optical applications e.g., photographic coatings, optical element coatings
  • agrochemicals, polishing agents and waxes e.g. for furniture, floors and automobiles, in particular in floor polishes, in fire extinguishing agents, lubricants, in
  • Immersion photolithography method e.g. in developer solutions, rinse solutions, immersion oils and / or in the photoresists themselves, especially for the production of printed circuits or in
  • Additive preparations for the addition of appropriate preparations.
  • the compounds useful according to the invention as surfactant for washing and cleaning applications, as well as for use as additives / surfactants in cosmetic products such.
  • Hair and body care products eg shampoos, hair conditioners and hair conditioners
  • bubble baths creams or lotions having one or more of the following functions: emulsifiers, wetting agents,
  • Adjuvants foam inhibitor, dispersing agent, emulsion stabilizer.
  • the compounds according to the invention can also be used as additives in deicing or anti-icing agents.
  • the fluorosurfactants according to the invention for application are usually incorporated in appropriately designed preparations. Usual use concentrations are 0.01 - 1.0 wt .-% of
  • Surfactants of the invention based on the total preparation.
  • agents containing the fluorosurfactants according to the invention are likewise provided by the present invention.
  • Such agents preferably contain a carrier suitable for the respective intended use, as well as optionally further active ingredients and / or optionally adjuvants.
  • Preferred agents are colored and
  • Preferred agents are dyestuff and lacquer preparations and printing inks.
  • Fluorosurfactants according to the invention alone or in admixture with additives, subject of the present invention Coating formulations based on the following synthetic film formers are preferably used: polycondensation resins such as alkyd resins, saturated / unsaturated polyesters, polyamides / imides, silicone resins; Phenol resins; Urea resins and melamine resins, polyaddition resins such as polyurethanes and epoxy resins, polymerization resins such as polyolefins, polyvinyl compounds and
  • fluorosurfactants according to the invention are also suitable for use in paints based on natural substances and modified natural products. Preference is given to lacquers based on oils, polysaccharides such as starch and cellulose and also based on natural resins such as cyclic
  • the fluorosurfactants according to the invention can be used both in physically curing (thermoplastics) and in crosslinking (elastomers and duromers) aqueous coating systems.
  • the fluorosurfactants according to the invention preferably improve the flow and
  • fluorine surfactants to be used according to the invention mentioned here are the subject matter of the present invention.
  • fluorosurfactants for the purposes mentioned is the
  • Drying tube, dropping funnel and thermometer are 30 ml absol. Submit Et2O and add 70 ml of 1 M LiAlH4 solution (0.07 mol) in Et2O via a septum. In the dropping funnel 44.30 g (0.12 mol) of methyl perfluoro (2-methyl-3-oxahexanoats) (ABCR, Düsseldorf Germany) in 50 ml absol. Et2O submitted.
  • Reaction process creates a turbid dispersion.
  • the batch is cooled in an ice bath.
  • the decomposition of the excess LiAlhU is carried out by adding 10 ml EtOAc with slight heat of reaction.
  • 10 g of H2O are added, whereupon a flaky aluminum hydroxide precipitate is formed.
  • 78 g of 25% strength sulfuric acid are added dropwise to the suspension over the course of 30 minutes, giving a clear two-phase mixture.
  • the organic phase is separated and the aqueous phase washed with 3x 40 ml Et2O.
  • the organic phases are combined, washed with 3 ⁇ 40 ml H 2 O and dried over Na 2 SO 4.
  • the ether is distilled off and the residue is fractionally distilled.
  • Product 31, 8 g (bp 57 ° C / 100 mbar); Purity 91% (GC-MS); Yield 73% of theory
  • the branched alcohol is reacted according to the prior art with ethylene oxide in the pressure reactor. (Conditions: 140 ° C, maximum 4 bar pressure). The reaction is stopped when the polyethylene oxide chain statistically contains 8, 12 and 17 units.
  • CMC Micelle concentration
  • Example 6 In a pressure reactor, the alcohol prepared in Example 6 is reacted with ethylene oxide at 140 ° C and max 4 bar pressure to the corresponding fluorosurfactant. Depending on the reaction time different chain lengths can be realized. Three materials with a statistically distributed repeat unit of 8, 12 and 17 are realized. The material is freed of low-boiling impurities by vacuum distillation. The static surface tension of the compounds and the CMC are shown in FIG. 1 as measured values B7-8EO, B7-12EO and B7-17EO.
  • the alcohol prepared in Example 8 is reacted with ethylene oxide at 140 ° C and max 4 bar pressure to the corresponding fluorosurfactant. According to the reaction time can
  • Fig. 1 Surface tension of the compounds and the CMC are shown in Fig. 1 as measured values B9-8EO, B9-12EO and B9-17EO.
  • Measuring method used Measurement of the surface tension with the Wilhelmy plate method according to DIN EN 14370.
  • the surface or interfacial tension of the surfactant solution is calculated from the force acting on the wetted length of a plate according to the following formula.
  • the plate consists of roughened platinum and is therefore optimally wetted, so that the contact angle ⁇ is close to 0 °.
  • the term cos ⁇ therefore reaches approximately the value 1, so that only the measured force and the length of the plate must be taken into account.
  • Fig. 1 shows a comparison of the static surface tensions and CMC of the synthesized short-chain fluorosurfactants with commercially available C6 (Capstone TM) and C8 (Zonyl TM) patterns. Measured values (marked by * ) above the bar are the determined CMC in g / l. For B7-12EO and B7-17EO no CMC could be determined. From Fig. 1 it can be seen that especially the materials of Example 3 and 10 cause a very good surface tension reduction. Compared to commercially available C6 compounds cut these

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Wood Science & Technology (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Materials Engineering (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Polyethers (AREA)
  • Paints Or Removers (AREA)
  • Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)

Abstract

La présente invention concerne de nouveaux composés comprenant des groupes terminaux fluorés, leur utilisation comme substances tensioactives, et des agents contenant ces composés.
EP15738275.5A 2014-07-28 2015-07-15 Tensioactifs fluorés Withdrawn EP3174843A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP14002621 2014-07-28
PCT/EP2015/001449 WO2016015830A1 (fr) 2014-07-28 2015-07-15 Tensioactifs fluorés

Publications (1)

Publication Number Publication Date
EP3174843A1 true EP3174843A1 (fr) 2017-06-07

Family

ID=51257236

Family Applications (1)

Application Number Title Priority Date Filing Date
EP15738275.5A Withdrawn EP3174843A1 (fr) 2014-07-28 2015-07-15 Tensioactifs fluorés

Country Status (8)

Country Link
US (1) US10392332B2 (fr)
EP (1) EP3174843A1 (fr)
JP (1) JP2017528558A (fr)
KR (1) KR20170040290A (fr)
CN (1) CN106536466A (fr)
RU (1) RU2017106261A (fr)
TW (1) TW201619106A (fr)
WO (1) WO2016015830A1 (fr)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR101911044B1 (ko) * 2016-11-11 2018-12-20 한국화학연구원 짧은 불화알킬기를 포함하는 하이브리드형 불소계 비이온 계면활성제 및 이의 제조방법
CN110585644B (zh) * 2019-09-12 2020-04-21 宁波镇火龙皇环保科技有限公司 具有高效环保抑蒸功能的泡沫灭火剂及其制备方法
EP3824868B1 (fr) 2019-11-20 2023-10-11 Zhermack S.p.a. Composition durcissable pour empreinte dentaire
JPWO2021106468A1 (fr) * 2019-11-26 2021-06-03
CN113527655B (zh) * 2021-08-03 2023-04-18 哈尔滨工业大学无锡新材料研究院 一种含氟非离子型大分子表面活性剂及其制备方法
KR102351564B1 (ko) * 2021-09-03 2022-01-17 (주)미유테크 하이브리드형 불소계 비이온 계면활성제의 제조방법
KR102351563B1 (ko) * 2021-09-03 2022-01-17 (주)미유테크 불화알킬글리세린 유도체 및 계면활성제 용도
KR102446846B1 (ko) * 2022-06-16 2022-09-26 (주)미유테크 불화알킬글리세린 유도체, 이의 제조방법 및 용도

Family Cites Families (26)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB8707032D0 (en) 1987-03-24 1987-04-29 Kodak Ltd Photographic material
GB8817811D0 (en) 1988-07-26 1988-09-01 Kodak Ltd Hydrophilic colloid compositions for photographic materials
US5157159A (en) 1991-06-13 1992-10-20 Minnesota Mining And Manufacturing Company Process for hydroxyalkylation of fluorinated alcohols
US5567857A (en) * 1994-06-21 1996-10-22 E. I. Du Pont De Nemours And Company Fluoroalkylethoxylate compositions having enhanced water solubility
JPH09111286A (ja) * 1995-10-13 1997-04-28 Nikko Chemical Co Ltd エマルション組成物及び洗浄剤組成物並びに洗浄方法
US6340779B1 (en) 1996-11-28 2002-01-22 Asahi Glass Company Ltd. Cement admixture, concrete, and process for producing fluorooxyalylene compounds
JP3801398B2 (ja) 1999-11-01 2006-07-26 信越化学工業株式会社 反射防止膜材料及びパターン形成方法
CN1535260B (zh) 2001-07-25 2011-11-23 西巴特殊化学品控股有限公司 全氟烷基取代的胺、酸、氨基酸和硫醚酸
US6890608B2 (en) 2002-03-29 2005-05-10 Fuji Photo Film Co., Ltd. Optical compensatory sheet, liquid-crystal display and elliptical polarizing plate employing same
JP2004240187A (ja) * 2003-02-06 2004-08-26 Fuji Photo Film Co Ltd 非イオン性フッ素化合物、界面活性剤およびそれを含む水性塗布組成物ならびにハロゲン化銀写真感光材料
JP2004264830A (ja) 2003-02-12 2004-09-24 Oji Paper Co Ltd インジケータ、ラベル及び温度／時間履歴検知方法
EP1762566B1 (fr) 2004-05-20 2011-03-23 Daikin Industries, Ltd. Tensioactif ramifie comportant un groupement fluoroalkyle et un groupement hydrocarbure
DE102005000858A1 (de) 2005-01-05 2006-07-20 Merck Patent Gmbh Fluortenside
JP4772387B2 (ja) * 2005-06-08 2011-09-14 株式会社ネオス ノニオン系含フッ素界面活性剤及びその製造方法
US9000048B2 (en) * 2006-11-28 2015-04-07 Wisconsin Alumni Research Foundation Fluoropolymer-based emulsions for the intravenous delivery of fluorinated volatile anesthetics
US7635789B2 (en) 2007-08-06 2009-12-22 E.I. Du Pont De Nemours And Company Fluoroalkyl acid amide surfactants
US7737307B2 (en) 2007-08-06 2010-06-15 E. I. Du Pont De Nemours And Company Fluorinated nonionic surfactants
DE102008027930A1 (de) 2008-06-12 2009-12-17 Merck Patent Gmbh Fluortenside
US8263800B2 (en) 2008-07-01 2012-09-11 E. I. Du Pont De Nemours And Company Partially fluorinated sulfonated surfactants
DE102008031599A1 (de) * 2008-07-07 2010-01-14 Merck Patent Gmbh Fluortenside
US8058480B2 (en) 2009-04-30 2011-11-15 E. I. Du Pont De Nemours And Company Process for the alkoxylation of alcohols
DE102009030846A1 (de) 2009-06-26 2010-12-30 Merck Patent Gmbh Fluortenside
WO2011082770A2 (fr) 2010-01-07 2011-07-14 Merck Patent Gmbh Tensioactifs fluorés
EP2655324A1 (fr) 2010-12-21 2013-10-30 Merck Patent GmbH Dérivés de sulfosuccinates de perfluoroalcoxy en tant que tensioactifs
JP6066621B2 (ja) * 2012-08-14 2017-01-25 公益財団法人野口研究所 アグリコン転位抑制効果を持つ無臭チオール誘導体
RU2559319C1 (ru) 2014-06-18 2015-08-10 Федеральное государственное бюджетное учреждение науки Институт органического синтеза им. И.Я. Постовского Уральского отделения Российской академии наук Способ получения 1,3-бис-о-(полифторалкил)глицерина

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
ADKINS S S ET AL: "Effect of branching on the interfacial properties of nonionic hydrocarbon surfactants at the airwater and carbon dioxidewater interfaces", JOURNAL OF COLLOID AND INTERFACE SCIENCE, ACADEMIC PRESS,INC, US, vol. 346, no. 2, 15 June 2010 (2010-06-15), pages 455 - 463, XP027030384, ISSN: 0021-9797, [retrieved on 20100426] *

Also Published As

Publication number Publication date
JP2017528558A (ja) 2017-09-28
KR20170040290A (ko) 2017-04-12
RU2017106261A3 (fr) 2019-02-12
RU2017106261A (ru) 2018-08-28
TW201619106A (zh) 2016-06-01
CN106536466A (zh) 2017-03-22
WO2016015830A1 (fr) 2016-02-04
US20170217863A1 (en) 2017-08-03
US10392332B2 (en) 2019-08-27

Similar Documents

Publication Publication Date Title
EP3174843A1 (fr) Tensioactifs fluorés
EP2874737B1 (fr) Tensioactifs fluorés
EP2445871B1 (fr) Tensioactifs fluorés
EP1833786B1 (fr) Agents tensioactifs fluores
WO2012084118A1 (fr) Dérivés de sulfosuccinates de perfluoroalcoxy en tant que tensioactifs
EP3107893B1 (fr) Tensioactifs fluorés
WO2011082770A2 (fr) Tensioactifs fluorés
WO2010003567A2 (fr) Tensio-actifs fluorés
WO2008003443A1 (fr) Tensioactifs fluorés
EP2282988A1 (fr) Tensioactifs fluorés
WO2008003444A1 (fr) Tensioactifs fluorés
EP3535241A1 (fr) Tensioactifs fluorés
EP3687983B1 (fr) Composés fluorés
EP3687966B1 (fr) Procédé de préparation de composés fluorés
EP2879782A2 (fr) Mélanges de tensioactifs
EP3107894B1 (fr) Tensioactifs fluorés
DE2329660B2 (de) Fluorhaltige sulfosuccinate, verfahren zu deren herstellung und deren verwendung
DE102012022441A1 (de) Neue Phosphinsäureamide, deren Herstellung und Verwendung

Legal Events

Date Code Title Description
17P Request for examination filed

Effective date: 20161214

AK Designated contracting states

Kind code of ref document: A1

Designated state(s): AL AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HR HU IE IS IT LI LT LU LV MC MK MT NL NO PL PT RO RS SE SI SK SM TR

AX Request for extension of the european patent

Extension state: BA ME

PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

Free format text: ORIGINAL CODE: 0009012

DAV Request for validation of the european patent (deleted)
DAX Request for extension of the european patent (deleted)
17Q First examination report despatched

Effective date: 20181001

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: THE APPLICATION IS DEEMED TO BE WITHDRAWN

18D Application deemed to be withdrawn

Effective date: 20191219