EP2282988A1 - Tensioactifs fluorés - Google Patents

Tensioactifs fluorés

Info

Publication number
EP2282988A1
EP2282988A1 EP09761370A EP09761370A EP2282988A1 EP 2282988 A1 EP2282988 A1 EP 2282988A1 EP 09761370 A EP09761370 A EP 09761370A EP 09761370 A EP09761370 A EP 09761370A EP 2282988 A1 EP2282988 A1 EP 2282988A1
Authority
EP
European Patent Office
Prior art keywords
compounds
formula
alkyl
tert
butoxy
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Withdrawn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
EP09761370A
Other languages
German (de)
English (en)
Inventor
Eckhard Claus
Fanny SCHOOREN
Martin Seidel
Wolfgang Herse
Peer Kirsch
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 EP2282988A1 publication Critical patent/EP2282988A1/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
    • C07C69/78—Benzoic acid esters
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/15—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings
    • C07C311/16—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to hydrogen atoms or to an acyclic carbon atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
    • C09K23/007—Organic compounds containing halogen

Definitions

  • the present invention relates to compounds of the formulas (I), (II) and (III), the use of compounds containing at least one perfluoro-tert-butoxy group and at least one substituted or unsubstituted aromatic end group as a surface-active agent and a process for Preparation of compounds of the formula (II).
  • Fluorosurfactants have a superior surface tension lowering ability, for example, in the hydrophobization of surfaces e.g. of textiles, paper, glass, building materials or adsorbents.
  • Fluorosurfactants generally contain perfluoroalkyl substituents which are degraded in the environment by biological and / or other oxidation processes to perfluoroalkylcarboxylic acids (PFCA 's ) and sulfonic acids (PFAS 's ).
  • PFCA 's perfluoroalkylcarboxylic acids
  • PFAS 's sulfonic acids
  • PFAS 's in nature cause for concern.
  • PFCA 's and PFAS 's are highly persistent compounds whose long-chain variants (with perfluoroalkyl chains of 8 or more carbon atoms) have a bioaccumulative potential. They are sometimes suspected of causing harm to their health (GL Kennedy, Jr., JL
  • JP-A-2001/133984 discloses surface-active compounds containing perfluoroalkoxy chains, which are suitable for use in antireflection coatings.
  • JP-A-09/111286 discloses the use of perfluoropolyether surfactants in emulsions.
  • a first subject of the present invention are therefore compounds of the formula I,
  • L linear or branched alkyl having at least 2 C atoms, wherein one or more non-adjacent carbon atoms may be replaced by O, S 1 and / or N, and / or one or more double and / or
  • Ar is preferably one with halogen, alkyl, cycloalkyl, aryl, -OH, -OR 1 , -
  • X O (O) C.
  • L is linear alkyl.
  • the compounds according to the invention may contain one or more perfluorot.-butoxy groups, preferably one, two or three such groups.
  • compounds with a perfluoro-tert-butoxy are particularly preferred.
  • the compounds according to the invention preferably contain no further fluorinated groups in addition to the perfluoro-tert-butoxy groups.
  • a preferred variant of the invention are compounds of the formula (II)
  • compounds with the aromatic substituents in the para position are preferred.
  • compounds with the aromatic substituents in ortho or may also be used Meta position, as well as a combination of substituents in ortho, meta and para position can be used.
  • Particularly preferred compounds of the present invention are the compounds of the formula (III)
  • Fluorosulfonic acids such as PFOA (perfluorooctanoic acid) or PFOS (perfluorooctanesulfonate),
  • the fluorosurfactants according to the invention are particularly suitable for use as hydrophobizing agents or oleophobicizing agents.
  • Surface coating preparations such as radiation-curing and high-solid or low-solid coatings, adhesives, printing inks, paints, Paints, lacquers, photographic coatings, special coatings for semiconductor photolithography (resists, top antireflective coatings, bottom antireflective coatings) or in additive formulations for the addition of appropriate preparations.
  • the compounds according to the invention for the application are usually incorporated in appropriately designed preparations.
  • agents which comprise at least one compound according to the invention are likewise provided by the present invention. Such agents preferably contain one for the respective one
  • Preferred carrier and optionally other active ingredients and / or optionally adjuvants.
  • Preferred agents are coatings, printing inks and adhesives.
  • a second object of the present invention is the use of compounds having at least one terminal perfluoro-tert-butoxy group and containing at least one substituted or unsubstituted aromatic end group as surfactants.
  • the compounds according to the invention can preferably be prepared by the following reactions.
  • R H, CH 2 CH 2 CH 3 , SO 2 N (CH 2 CH 3 ) 2 , SO 2 N (CH 2 CH 2 CH 3 ) 2
  • R H 1 CH 2 CH 2 CH 3 , SO 2 N (CH 2 CH j ) 2 , SO 2 N (CH 2 CH 2 CH 3 ) 2 3.: Esterification via the acid chloride
  • R H, CH 2 CH 2 CH 3 , SO 2 N (CH 2 CH 3 ) 2 , SO 2 N (CH 2 CH 2 CH 3 ) 2
  • the crude product is dissolved in a little ethanol and in six times the amount
  • the crude product is dissolved in tert-butyl methyl ether, treated with 1 N sodium hydroxide solution and the phases separated.
  • the organic phase is washed with water and saturated sodium chloride solution and dried over sodium sulfate.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

La présente invention concerne des composés de formules (I), (II) et (III), l'utilisation de composés contenant au moins un groupe perfluoro-tert.-butoxy et au moins un groupe terminal aromatique substitué ou non substitué en tant qu'agent tensioactif, ainsi qu'un procédé de production de composés de formule (II).
EP09761370A 2008-06-12 2009-05-15 Tensioactifs fluorés Withdrawn EP2282988A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102008027930A DE102008027930A1 (de) 2008-06-12 2008-06-12 Fluortenside
PCT/EP2009/003487 WO2009149807A1 (fr) 2008-06-12 2009-05-15 Tensioactifs fluorés

Publications (1)

Publication Number Publication Date
EP2282988A1 true EP2282988A1 (fr) 2011-02-16

Family

ID=40887890

Family Applications (1)

Application Number Title Priority Date Filing Date
EP09761370A Withdrawn EP2282988A1 (fr) 2008-06-12 2009-05-15 Tensioactifs fluorés

Country Status (5)

Country Link
US (1) US20110088594A1 (fr)
EP (1) EP2282988A1 (fr)
JP (1) JP2011522847A (fr)
DE (1) DE102008027930A1 (fr)
WO (1) WO2009149807A1 (fr)

Families Citing this family (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP5902397B2 (ja) * 2010-03-30 2016-04-13 ダイキン工業株式会社 結晶性含フッ素アクリル酸エステル重合体、その製法、および撥水撥油剤
EP2479616A1 (fr) 2011-01-25 2012-07-25 Basf Se Utilisation de tensioactifs dotés d'au moins trois groupes RF perfluorés à courte chaîne pour fabriquer des circuits intégrés ayant des motifs avec des dimensions d'interlignage inférieures à 50 nm
US9236256B2 (en) 2011-01-25 2016-01-12 Basf Se Use of surfactants having at least three short-chain perfluorinated groups RF for manufacturing integrated circuits having patterns with line-space dimensions below 50 NM
MY165866A (en) 2011-03-18 2018-05-18 Basf Se Method for manufacturing integrated circuit devices, optical devices, micromachines and mechanical precision devices having patterned material layers with line-space dimensions of 50 nm and less
EP2500777A1 (fr) 2011-03-18 2012-09-19 Basf Se Procédé de fabrication de dispositifs de circuit intégré, dispositifs optiques, micromachines et de dispositifs de précision mécanique dotés de couches de matériau avec des motifs de dimensions inférieures ou égales à 50 nm
JP6392753B2 (ja) 2012-07-18 2018-09-19 メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツングＭｅｒｃｋ Ｐａｔｅｎｔ Ｇｅｓｅｌｌｓｃｈａｆｔ ｍｉｔ ｂｅｓｃｈｒａｅｎｋｔｅｒ Ｈａｆｔｕｎｇ フッ素化界面活性剤
US10590262B2 (en) 2012-08-06 2020-03-17 Merck Patent Gmbh Surfactant mixtures
CN104871289B (zh) 2012-12-14 2017-10-10 巴斯夫欧洲公司 包含表面活性剂和疏水化剂的组合物在处理线间距尺寸为50nm或更低的图案化材料时避免图案崩塌的用途
WO2014194984A1 (fr) 2013-06-04 2014-12-11 Merck Patent Gmbh Tensio-actifs fluorés dans des pesticides
EP2824511A1 (fr) 2013-07-11 2015-01-14 Basf Se Utilisation de tensioactifs présentant au moins trois groupes perfluorés à chaîne courte dans des formulations de nettoyage de masque photo
WO2015124290A1 (fr) 2014-02-21 2015-08-27 Merck Patent Gmbh Tensioactifs fluorés
JP6669661B2 (ja) 2014-02-21 2020-03-18 メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツングＭｅｒｃｋ Ｐａｔｅｎｔ Ｇｅｓｅｌｌｓｃｈａｆｔ ｍｉｔ ｂｅｓｃｈｒａｅｎｋｔｅｒ Ｈａｆｔｕｎｇ フッ素化界面活性剤
RU2017106261A (ru) 2014-07-28 2018-08-28 Мерк Патент Гмбх Фтортензиды
WO2016142026A1 (fr) 2015-03-06 2016-09-15 Merck Patent Gmbh Tensioactifs fluorés situés dans des émulsions
WO2017008877A1 (fr) 2015-07-14 2017-01-19 Merck Patent Gmbh Compositions d'agents tensioactifs fluorés et d'antioxydants
DE102016013066A1 (de) 2016-11-03 2018-05-03 Merck Patent Gmbh Fluortenside

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3385904A (en) 1962-10-30 1968-05-28 Minnesota Mining & Mfg Decyclization of fluorinated cyclic ethers to perfluorinated tertiary alcohols
US3668233A (en) 1962-10-30 1972-06-06 Minnesota Mining & Mfg Esters of perfluoro-tertiaryalkyl alcohols and hydrocarbyl or holo-hydrocarbyl carboxylic acids
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
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
KR20040029380A (ko) 2001-07-25 2004-04-06 시바 스페셜티 케미칼스 홀딩 인크. 퍼플루오로알킬 치환된 아민, 산, 아미노산 및 티오에테르산
DE102005000858A1 (de) 2005-01-05 2006-07-20 Merck Patent Gmbh Fluortenside
US8252778B2 (en) * 2006-03-24 2012-08-28 University Of Utah Research Foundation Highly fluorinated oils and surfactants and methods of making and using same

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO2009149807A1 *

Also Published As

Publication number Publication date
US20110088594A1 (en) 2011-04-21
WO2009149807A1 (fr) 2009-12-17
JP2011522847A (ja) 2011-08-04
DE102008027930A1 (de) 2009-12-17

Similar Documents

Publication Publication Date Title
WO2009149807A1 (fr) Tensioactifs fluorés
EP1833786B1 (fr) Agents tensioactifs fluores
WO2008003443A1 (fr) Tensioactifs fluorés
DE102008031599A1 (de) Fluortenside
EP2521709A2 (fr) Tensioactifs fluorés
WO2008003447A2 (fr) Tensioactifs fluorés
WO2010149262A1 (fr) Tensioactifs fluorés
WO2008003444A1 (fr) Tensioactifs fluorés
EP2874737B1 (fr) Tensioactifs fluorés
EP3107893B1 (fr) Tensioactifs fluorés
WO2008003446A2 (fr) Tensioactifs fluorés
EP2035130A1 (fr) Tensioactifs fluorés
WO2016015830A1 (fr) Tensioactifs fluorés
DE1668420A1 (de) N-substituierte Perfluoralkylsulfonamide
EP0601418B1 (fr) Esters carboniques fluorinés d'acides phosphono et phosphino carboxyliques et leur utilisation
DE102011114650A1 (de) Oberflächenaktive Substanzen mit terminaler Pentafluorsulfoxy-Gruppe
EP3535241A1 (fr) Tensioactifs fluorés
DE102011114651A1 (de) Oberflächenaktive Substanzen mit terminaler Pentafluorsulfoxy-Gruppe
EP3107894B1 (fr) Tensioactifs fluorés
EP0128489B1 (fr) Procédé de préparation d'esters dialkyliques de l'acide succinylsuccinique

Legal Events

Date Code Title Description
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

17P Request for examination filed

Effective date: 20101029

AK Designated contracting states

Kind code of ref document: A1

Designated state(s): 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 SE SI SK TR

AX Request for extension of the european patent

Extension state: AL BA RS

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

Effective date: 20120229

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: 20120911