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WO2004018535A1 - Tensioactifs fluores - Google Patents

Tensioactifs fluores Download PDF

Info

Publication number
WO2004018535A1
WO2004018535A1 PCT/JP2003/010509 JP0310509W WO2004018535A1 WO 2004018535 A1 WO2004018535 A1 WO 2004018535A1 JP 0310509 W JP0310509 W JP 0310509W WO 2004018535 A1 WO2004018535 A1 WO 2004018535A1
Authority
WO
WIPO (PCT)
Prior art keywords
monomer
mass
surfactant according
surface tension
water
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.)
Ceased
Application number
PCT/JP2003/010509
Other languages
English (en)
Japanese (ja)
Inventor
Shunji Odaka
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.)
Seimi Chemical Co Ltd
Original Assignee
Seimi Chemical Co 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 Seimi Chemical Co Ltd filed Critical Seimi Chemical Co Ltd
Priority to JP2004530578A priority Critical patent/JP4544996B2/ja
Priority to AU2003257623A priority patent/AU2003257623A1/en
Publication of WO2004018535A1 publication Critical patent/WO2004018535A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/22—Esters containing halogen
    • C08F220/24—Esters containing halogen containing perhaloalkyl radicals
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F283/00—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
    • C08F283/06—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to polyethers, polyoxymethylenes or polyacetals
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
    • C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
    • C08F290/06—Polymers provided for in subclass C08G
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
    • C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
    • C08F290/06—Polymers provided for in subclass C08G
    • C08F290/062—Polyethers

Definitions

  • the present invention relates to a novel fluorinated surfactant.
  • Fluorosurfactants which have a high surface tension lowering ability, are widely used in coatings and other coatings for the purpose of improving the uniformity and smoothness of coating films.
  • To reduce the accumulation in the human body it is necessary to improve the solubility in water.However, in this case, there is a problem that the ability to lower the surface tension is reduced, and the surface tension reduction ability is high.
  • An object of the present invention is to provide a fluorine-based surfactant having excellent solubility in water and excellent surface tension lowering ability.
  • the present invention is a fluorosurfactant comprising a copolymer obtained by copolymerizing the following monomers A, B and C as a polymerization component.
  • n an integer of 1 to 3.
  • Ri hydrogen atom or methyl group
  • R f a fluoroalkyl group having 1 to 20 carbon atoms.
  • the fluorine-based surfactant of the present invention has low solubility in water due to its high solubility in water, has a high ability to lower surface tension, and has excellent properties such as leveling properties.
  • R f in monomer A which is a raw material of the copolymer of the present invention, is a fluoroalkyl group
  • R f is a fluoroalkyl group
  • R f preferably has 4 to 18 carbon atoms, particularly preferably 4 to 12 carbon atoms.
  • monomer A having a perfluoroalkyl group having 42 ash atoms include the following.
  • A— 14: C 4 F 9 CH 2 CH 2 OCOC (CH 3 ) CH:
  • the present invention is, of course, not limited by the specific examples.
  • the monomers B and C which are the raw materials of the copolymer of the present invention, are composed of only a polyoxypropylene group.
  • the solubility of the copolymer is significantly reduced, and on the other hand, if it is composed of only polyoxyethylene groups and does not contain, for example, polyoxypropylene groups, there is a problem with the compatibility of the copolymer with other polymers or pigments There is.
  • Both the monomers B and C need to have different types of polyoxyalkylene bonds, that is, need to have two or more types of polyoxyalkylene bonds.
  • 1 i,,, 12 , m 2 , and n 2 are preferably 5 to 60, and particularly preferably 10 to 40. They need not be equal.
  • the monomer B include (meth) acrylates in which 1 i,, and are 4 to 10, 8 to 20, and 4 to 10, respectively.
  • the monomer C which is a raw material of the copolymer of the present invention include di (meth) acrylates in which 12 rrl 2 n 2 is 4 20 840 420.
  • the monomers AB and C having the above structure Any structure such as block, random, alternating, or graft may be used as long as the copolymer is copolymerized within the range of the mixing ratio.
  • the graft ratio of the graft copolymer, the random copolymer There is no particular concern for randomness.
  • the monomers A, B and C can be used alone or in a mixture of two or more as long as they are within the range represented by the structural formulas described above.
  • Preferred combinations of monomers A, B and C are A-1, B-4 and C-4; A-7, B-4 and C-14; A-7, B-5 and C-15; A-1, A-3, A-5, A-7, B-4 and C-14. Particularly preferred combinations are A-1, B-4 and C-4.
  • the copolymerization ratio (mass ratio) of the monomers A, B, and C constituting the copolymer of the present invention may be determined by, for example, the blend in the composition in which the copolymer is blended, the level of the desired physical properties, and the like.
  • AZ (B + C) preferably in the range of 5/95 to 70/30, and more preferably in the range of 10Z90 to 50Z50.
  • the molecular weight of the copolymer according to the present invention is preferably such that the weight average molecular weight Mw in terms of polymethyl methacrylate is 1,000 to 100,000, and 3,000. It is particularly preferable that the number is 100,000. When the Mw is less than 1,000, it is difficult to obtain a sufficient surface tension lowering ability. Conversely, when the Mw exceeds 100,000, the compatibility with the compound in the composition becomes poor. descend.
  • the method for producing the copolymer of the present invention is not limited at all, and is based on known methods, that is, a solution polymerization method, a bulk polymerization method, and an emulsification method based on polymerization mechanisms such as a radical polymerization method, a cationic polymerization method, and an anion polymerization method.
  • a radical polymerization method is particularly simple and industrially preferable.
  • polymerization initiators can be used, for example, peroxides such as benzoyl peroxide, azo compounds such as azobisisobutyl nitrile, and transition metal catalysts that cause living radical polymerization And the like.
  • a chain transfer agent such as octyl mercaptan and 2-mercaptoethanol can be used.
  • the polymerization can be carried out in the presence of a solvent or water, or in the absence of a solvent, but is preferably carried out in the presence of a solvent from the viewpoint of workability.
  • the solvent include alcohols such as ethanol and isopropyl alcohol, ketones such as acetone, methyl ethyl ketone, and methyl isobutyl ketone; esters such as methyl acetate, ethyl acetate, methyl lactate, and butyl lactate; dimethylformamide, dimethyl sulfoxide; Polar solvents such as methylpyrrolidone; ethers such as methylcellulose solvent, butylcellulose solvent, and butylcarbyl; propylene glycols and esters such as propylene glycol, propylene glycol monoethyl ether acetate; Octalogen compounds such as trichlorene, aromatic hydrocarbons such as benzene, toluene, and xylene, and fluorinated initiators
  • the fluorine-based surfactant according to the present invention may be prepared by using only one type of the copolymer, or may be prepared by using two or more types of the copolymer simultaneously.
  • various surfactants such as hydrocarbon-based, fluorine-based, and silicone-based surfactants can be used in combination for the purpose of improving the compatibility with each component in the fluorine-based surfactant.
  • the solubility of the fluorinated surfactant of the present invention in water at room temperature (at 250 is preferably 1% by mass or more.
  • solubility is in the above range, accumulation in the human body is reduced and safety is reduced. Excellent.
  • the fluorine-based surfactant of the present invention preferably has a surface tension of a 1% by mass aqueous solution at room temperature (25 ° C.) of 25 mNZm or less.
  • a surface tension of a 1% by mass aqueous solution at room temperature (25 ° C.) of 25 mNZm or less.
  • the fluorosurfactant of the present invention is used for its excellent surface active effects, such as a leveling agent for inks, paints, resists, curable resins, etc., a dispersant for pigments, a fire extinguisher for agriculture, Examples include an antifog agent for a film, and a dispersant for a medium-viscosity aqueous pole pen pigment ink.
  • Monomer A-1 in a glass flask equipped with a stirrer, condenser and thermometer 20 parts by mass, 60 parts by mass of monomer B-4, 20 parts by mass of monomer C-4, and 200 parts by mass of ethyl acetate, and polymerized at 70 ° C in a nitrogen gas stream.
  • V_65 azopisdimethylpareronitrile
  • octyl mercaptan as a chain transfer agent
  • the weight average molecular weight Mw of the copolymer as determined by gel permeation chromatography (GPC) was 30,000 in terms of methyl methyl acrylate.
  • Table 1 shows the solubility of the obtained copolymer in water, the amount of the copolymer added to water (1% by mass, 0.1% by mass, 0.01% by mass) and the static surface tension. Indicated. Table 1 also shows the static surface tension when no copolymer was added (control example).
  • the sample prepared so that the concentration of the aqueous solution becomes 0.01%, 0.1%, 1%, and 5% by mass is sufficiently stirred, and left at 25 ° C for 1 hour. After this, the presence or absence of insoluble components was visually checked.
  • the static surface tension was measured by a Wilhelmy method using a ground glass plate at 25 ° C using a surface tension meter CBVB-A3 (manufactured by Kyowa Kagaku Co., Ltd.).
  • Example 1 A-7 was used in place of monomer A-1, Under the same conditions, copolymerization of monomer B-4 and monomer C-14 was performed.
  • the weight average molecular weight Mw in terms of polymethyl methacrylate of this copolymer was 20,000.
  • the solubility of the obtained copolymer in water, the amount of the copolymer added to water (1% by mass, 0.1% by mass, 0.01% by mass), and the static surface tension were determined in Example 1. The results were shown in Table 1.
  • Example 1 a mixture of monomer A instead of monomer A-1 (A-7: 2%, A-1: 77%, A-3: 18%, A-5: 3% However, the above-mentioned% represents gas chromatography purity), and the monomers B-4 and C-4 were copolymerized under exactly the same conditions as in Example 1.
  • the weight average molecular weight Mw in terms of polymethyl methacrylate of this copolymer was 22,000.
  • the solubility of the obtained copolymer in water, the amount of the copolymer added to water (1% by mass, 0.1% by mass, 0.01% by mass), and the static surface tension were determined as in Example 1. The measurement was performed similarly, and the results are shown in Table 1.
  • Example 1 copolymerization of monomer B_4 and monomer C-14 was performed under the same conditions as in Example 1 without adding monomer A-1.
  • the weight average molecular weight Mw in terms of polymethyl methacrylate of this copolymer was 50,000.
  • the solubility of the obtained copolymer in water, the amount of the copolymer added to water (1% by mass, 0.1% by mass, 0.01% by mass) and the static surface tension were measured in Example 1. The measurement was carried out in the same manner as in Example 1. The results are shown in Table 1.
  • Example 1 was repeated without adding monomer B-4 and monomer C-14. Polymerization of monomer A-1 was carried out under exactly the same conditions as in 1. The weight average molecular weight Mw in terms of polymethyl methacrylate of this polymer was 20,000. The solubility of the obtained polymer in water, the amount of the copolymer added to water (1% by mass, 0.1% by mass, 0.01% by mass) and the static surface tension were the same as in Example 1. The results are shown in Table 1. Table 1: Solubility of surfactant in water and amount added to water

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
  • Macromonomer-Based Addition Polymer (AREA)

Abstract

L'invention concerne des tensioactifs fluorés présentant une faible tension superficielle statique et une haute solubilité dans l'eau, lesquels tensioactifs sont chacun constitués d'un copolymère obtenu par copolymérisation des monomères (A), (B) et (C) suivants : monomère (A) de formule Rf-Q-OCOC(R1)=CH2, dans laquelle Q est représenté par la formule (CH2)n- ou CH2CH2CH(CH3), n étant un nombre entier de 1 à 3 ; R1 désigne hydrogène ou méthyle et Rf est un alkyle fluoré présentant 1 à 20 atomes de carbone ; monomère (B) de formule HO(C2H4O)l1(C3H6O)m1(C2H4O)n1COC(R2)=CH2 et monomère (C) de formule CH2=C(R3)COO(C2H4O)l2(C3H6O)m2(C2H4O)n2COC(R4)=CH2, dans laquelle R2, R3 et R4 représentent chacun hydrogène ou méthyle et l1, m1, n1, l2, m2 et n2 représentent chacun un nombre entier de 1 à 100.
PCT/JP2003/010509 2002-08-22 2003-08-20 Tensioactifs fluores Ceased WO2004018535A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
JP2004530578A JP4544996B2 (ja) 2002-08-22 2003-08-20 フッ素系界面活性剤
AU2003257623A AU2003257623A1 (en) 2002-08-22 2003-08-20 Fluorosurfactants

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2002241434 2002-08-22
JP2002/241434 2002-08-22

Publications (1)

Publication Number Publication Date
WO2004018535A1 true WO2004018535A1 (fr) 2004-03-04

Family

ID=31943993

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2003/010509 Ceased WO2004018535A1 (fr) 2002-08-22 2003-08-20 Tensioactifs fluores

Country Status (4)

Country Link
JP (1) JP4544996B2 (fr)
AU (1) AU2003257623A1 (fr)
TW (1) TW200404821A (fr)
WO (1) WO2004018535A1 (fr)

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2006249130A (ja) * 2005-03-08 2006-09-21 Dainippon Ink & Chem Inc フッ素化アルキル基含有オリゴマーの製造方法
JP2007186671A (ja) * 2005-12-13 2007-07-26 Agc Seimi Chemical Co Ltd 界面活性剤および表面張力低下方法
JP2008222909A (ja) * 2007-03-14 2008-09-25 Dic Corp メタリック塗料
JP2010055054A (ja) * 2008-03-12 2010-03-11 Fujifilm Corp 感光性樹脂組成物、感光性樹脂転写材料、フォトスペーサー及びその製造方法、表示装置用基板、並びに、表示装置
WO2012002361A1 (fr) * 2010-07-02 2012-01-05 Dic株式会社 Tensioactif à base de fluor, et composition de revêtement et composition de réserve utilisant celui-ci
JP2012062433A (ja) * 2010-09-17 2012-03-29 Dic Corp フッ素系界面活性剤、それを用いたコーティング組成物及びレジスト組成物
WO2012111741A1 (fr) * 2011-02-18 2012-08-23 Ａｇｃセイミケミカル株式会社 Tensioactif, composition contenant un tensioactif, son utilisation et composé contenant du fluor
JP5306815B2 (ja) * 2006-09-07 2013-10-02 国立大学法人豊橋技術科学大学 共重合体およびその製造方法
JP2014051863A (ja) * 2012-09-10 2014-03-20 Asahi Glass Co Ltd 炭化水素含有地層の処理方法、炭化水素の回収方法および炭化水素含有地層処理用組成物

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR101774254B1 (ko) * 2015-12-16 2017-09-04 주식회사 해림엔지니어링 질소산화물 저감용 선택적 무촉매 환원제

Citations (6)

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Publication number Priority date Publication date Assignee Title
JPS6236657A (ja) * 1985-08-10 1987-02-17 Japan Synthetic Rubber Co Ltd 半導体微細加工用レジスト組成物
EP0239082A2 (fr) * 1986-03-27 1987-09-30 Fuji Photo Film Co., Ltd. Composition photosensible
JPH09281636A (ja) * 1996-04-15 1997-10-31 Fuji Photo Film Co Ltd 熱現像感光材料
JPH10168140A (ja) * 1996-12-10 1998-06-23 Shin Etsu Chem Co Ltd 塗料添加剤
US6156860A (en) * 1997-02-18 2000-12-05 Dainippon Ink And Chemicals, Inc. Surface active agent containing fluorine and coating compositions using the same
EP1246012A2 (fr) * 2001-03-30 2002-10-02 Fuji Photo Film Co., Ltd. Précurseur d une plaque lithographique

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH10309455A (ja) * 1997-05-13 1998-11-24 Dainippon Ink & Chem Inc フッ素系界面活性剤及びそれを使用した組成物
JPH11209787A (ja) * 1998-01-28 1999-08-03 Dainippon Ink & Chem Inc フッ素系界面活性剤及びその組成物
JP4055217B2 (ja) * 1997-02-18 2008-03-05 大日本インキ化学工業株式会社 フッ素系界面活性剤及びそれを使用した組成物

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS6236657A (ja) * 1985-08-10 1987-02-17 Japan Synthetic Rubber Co Ltd 半導体微細加工用レジスト組成物
EP0239082A2 (fr) * 1986-03-27 1987-09-30 Fuji Photo Film Co., Ltd. Composition photosensible
JPH09281636A (ja) * 1996-04-15 1997-10-31 Fuji Photo Film Co Ltd 熱現像感光材料
JPH10168140A (ja) * 1996-12-10 1998-06-23 Shin Etsu Chem Co Ltd 塗料添加剤
US6156860A (en) * 1997-02-18 2000-12-05 Dainippon Ink And Chemicals, Inc. Surface active agent containing fluorine and coating compositions using the same
EP1246012A2 (fr) * 2001-03-30 2002-10-02 Fuji Photo Film Co., Ltd. Précurseur d une plaque lithographique

Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2006249130A (ja) * 2005-03-08 2006-09-21 Dainippon Ink & Chem Inc フッ素化アルキル基含有オリゴマーの製造方法
JP2007186671A (ja) * 2005-12-13 2007-07-26 Agc Seimi Chemical Co Ltd 界面活性剤および表面張力低下方法
JP5306815B2 (ja) * 2006-09-07 2013-10-02 国立大学法人豊橋技術科学大学 共重合体およびその製造方法
JP2008222909A (ja) * 2007-03-14 2008-09-25 Dic Corp メタリック塗料
JP2010055054A (ja) * 2008-03-12 2010-03-11 Fujifilm Corp 感光性樹脂組成物、感光性樹脂転写材料、フォトスペーサー及びその製造方法、表示装置用基板、並びに、表示装置
KR101608762B1 (ko) 2008-03-12 2016-04-04 후지필름 가부시키가이샤 감광성 수지 조성물, 감광성 수지 전사 재료, 포토 스페이서와 그 제조 방법, 표시 장치용 기판, 및 표시 장치
JP4973966B2 (ja) * 2010-07-02 2012-07-11 Ｄｉｃ株式会社 フッ素系界面活性剤、それを用いたコーティング組成物及びレジスト組成物
CN102971391A (zh) * 2010-07-02 2013-03-13 Dic株式会社 氟系表面活性剂、使用其的涂层组合物以及抗蚀剂组合物
WO2012002361A1 (fr) * 2010-07-02 2012-01-05 Dic株式会社 Tensioactif à base de fluor, et composition de revêtement et composition de réserve utilisant celui-ci
CN102971391B (zh) * 2010-07-02 2014-10-22 Dic株式会社 氟系表面活性剂、使用其的涂层组合物以及抗蚀剂组合物
JP2012062433A (ja) * 2010-09-17 2012-03-29 Dic Corp フッ素系界面活性剤、それを用いたコーティング組成物及びレジスト組成物
WO2012111741A1 (fr) * 2011-02-18 2012-08-23 Ａｇｃセイミケミカル株式会社 Tensioactif, composition contenant un tensioactif, son utilisation et composé contenant du fluor
JP2014051863A (ja) * 2012-09-10 2014-03-20 Asahi Glass Co Ltd 炭化水素含有地層の処理方法、炭化水素の回収方法および炭化水素含有地層処理用組成物

Also Published As

Publication number Publication date
JPWO2004018535A1 (ja) 2005-12-08
TW200404821A (en) 2004-04-01
JP4544996B2 (ja) 2010-09-15
AU2003257623A1 (en) 2004-03-11

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