[go: up one dir, main page]

WO2014148474A1 - Agent antimousse, composition de tensioactif, composition de revêtement, et composition de réserve - Google Patents

Agent antimousse, composition de tensioactif, composition de revêtement, et composition de réserve Download PDF

Info

Publication number
WO2014148474A1
WO2014148474A1 PCT/JP2014/057288 JP2014057288W WO2014148474A1 WO 2014148474 A1 WO2014148474 A1 WO 2014148474A1 JP 2014057288 W JP2014057288 W JP 2014057288W WO 2014148474 A1 WO2014148474 A1 WO 2014148474A1
Authority
WO
WIPO (PCT)
Prior art keywords
meth
group
acrylate
carbon atoms
compound
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/JP2014/057288
Other languages
English (en)
Japanese (ja)
Inventor
良平 清水
弘行 濱野
啓 高野
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.)
DIC Corp
Original Assignee
DIC Corp
Dainippon Ink and Chemicals 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 DIC Corp, Dainippon Ink and Chemicals Co Ltd filed Critical DIC Corp
Priority to KR1020157025127A priority Critical patent/KR102241109B1/ko
Priority to CN201480017244.9A priority patent/CN105050681B/zh
Priority to JP2014536032A priority patent/JP5668899B1/ja
Publication of WO2014148474A1 publication Critical patent/WO2014148474A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
    • C07C323/51—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C323/52—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D19/00—Degasification of liquids
    • B01D19/02—Foam dispersion or prevention
    • B01D19/04—Foam dispersion or prevention by addition of chemical substances
    • B01D19/0404—Foam dispersion or prevention by addition of chemical substances characterised by the nature of the chemical substance
    • B01D19/0427—Foam dispersion or prevention by addition of chemical substances characterised by the nature of the chemical substance compounds containing halogen-atoms
    • 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
    • C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
    • 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
    • C09D7/47—Levelling agents
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/0048—Photosensitive materials characterised by the solvents or agents facilitating spreading, e.g. tensio-active agents
    • 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
    • C09D201/00—Coating compositions based on unspecified macromolecular compounds

Definitions

  • the (meth) acryloyl group is a generic term for an acryloyl group and a methacryloyl group.
  • the fluorinated alkyl group is one in which all hydrogen atoms in the alkyl group are substituted with fluorine atoms (perfluoroalkyl group), and one in which some hydrogen atoms in the alkyl group are substituted with fluorine atoms ( For example, HCF 2 CF 2 CF 2 CF 2 — and the like.
  • fluorinated alkyl group is one in which all hydrogen atoms in the alkyl group are substituted with fluorine atoms (perfluoroalkyl group), and one in which some hydrogen atoms in the alkyl group are substituted with fluorine atoms ( For example, HCF 2 CF 2 CF 2 CF 2 — and the like.
  • those containing an oxygen atom in the fluorinated alkyl group for example, CF 3 — (OCF 2 CF 2
  • norbornane diisocyanate isophorone diisocyanate, or adamantyl diisocyanate. That is, as urethane (meth) acrylate (a1-2), a hydroxyl group-containing (meth) acrylate (x1) having two or more (meth) acryloyl groups is reacted with an isocyanate compound (x2) having an alicyclic structure. It is preferable that it is urethane (meth) acrylate obtained.
  • the compound (a1) used in the present invention is highly effective in improving antifoaming properties and does not cause repellency or unevenness in the coating film. Therefore, dipentaerythritol hexaacrylate, pentaerythritol triacrylate, pentaerythritol tetraacrylate, ditrimethylolpropane.
  • One or more compounds selected from the group consisting of tetraacrylate, polyoxypropylene diacrylate and polyoxyethylene diacrylate are preferred.
  • Y is an oxygen atom or a sulfur atom
  • p and q are each an integer of 1 to 4
  • Rf and Rf 1 are each —C n F2 n + 1 (n is an integer of 1 to 20).
  • L and L 1 are each a carbonyl group, one or more groups selected from the group consisting of a carbonyl group-containing alkyl group having 1 to 4 carbon atoms and an alkyl group having 1 to 4 carbon atoms.] Are preferred.
  • organic acid ester examples include carboxylic acid esters and sulfonic acid esters.
  • organic acid amide examples include carboxylic acid amides and sulfonic acid amides.
  • organic acid imide examples include carboxylic acid imide and sulfonic acid imide.
  • Examples of the (3) solvent used in the resist composition of the present invention include ketones such as acetone, methyl ethyl ketone, cyclohexanone, cyclopentanone, cycloheptanone, 2-heptanone, methyl isobutyl ketone, and butyrolactone; methanol, ethanol, alcohols such as n-propyl alcohol, iso-propyl alcohol, n-butyl alcohol, iso-butyl alcohol, tert-butyl alcohol, pentanol, heptanol, octanol, nonanol, decanol; ethylene glycol dimethyl ether, ethylene glycol diethyl ether, Ethers such as dioxane;
  • the addition amount of the fluorosurfactant in the coating composition varies depending on the type of resist composition, the coating method, the target film thickness, and the like, but it is 0.00% relative to 100 parts by mass of the solid content of the resist composition.
  • the amount is preferably 0001 to 10 parts by mass, more preferably 0.001 to 5 parts by mass, and still more preferably 0.01 to 2 parts by mass.
  • Example 5 (same as above) In a glass flask equipped with a stirrer, a condenser and a thermometer, 59 g of 3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctanethiol in an air stream And 2 g of triethylamine were added. 41 g of polyoxypropylene diacrylate having 7 repeating units was set in a dropping device and dropped over 1 hour. After completion of dropping, the mixture was stirred at 85 ° C. for 12 hours. After completion of the reaction, the unreacted raw material was distilled off under reduced pressure to obtain the antifoaming agent (5) of the present invention having a solid content of 100%. The number average molecular weight of the defoamer (5) was 1,354, and the weight average molecular weight was 1,393. The fluorine content was 35.9% by mass.
  • the antifoaming agent (7) was found to be 3,3,4,4,5,5,6,6,7,7,8,8 per mole of polyoxybutylene diacrylate having 4 repeating units.
  • 8-Tridecafluorooctanethiol was added in an average of 2.0 moles.
  • Example 12 (same as above) In a glass flask equipped with a stirrer, a condenser and a thermometer, 37 g of 3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctanethiol in an air stream And 1 g of triethylamine was added. 13 g of 1,10-decanediol diacrylate was added dropwise over 1 hour. After completion of dropping, the mixture was stirred at 85 ° C. for 6 hours. After completion of the reaction, the unreacted raw material was distilled off under reduced pressure to obtain the antifoaming agent (12) of the present invention having a solid content of 100%. The defoamer (12) had a number average molecular weight of 1,119 and a weight average molecular weight of 1,123. The fluorine content was 47.4% by mass.
  • Comparative Example 2 (same as above) In a glass flask equipped with a stirrer, a condenser and a thermometer, 20 g of 3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctanethiol in an air stream And 0.1 g of triethylamine was added. 30 g of dipentaerythritol hexaacrylate was set in a dropping device and dropped over 1 hour. After completion of dropping, the mixture was stirred at 85 ° C. for 12 hours. After completion of the reaction, the unreacted raw material was distilled off under reduced pressure to obtain a comparative antifoaming agent (2 ′) having a solid content of 100%. The defoamer (2 ′) had a number average molecular weight of 1,157 and a weight average molecular weight of 1,165. The fluorine content was 25.8% by mass.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Health & Medical Sciences (AREA)
  • Toxicology (AREA)
  • Dispersion Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Paints Or Removers (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Degasification And Air Bubble Elimination (AREA)
  • Materials For Photolithography (AREA)

Abstract

L'objet de la présente invention est de pourvoir à un agent antimousse ayant une capacité antimousse considérablement améliorée, sans effet adverse sur la douceur de la surface, et une composition de tensioactif, une composition de revêtement, et une composition de réserve le contenant. L'agent antimousse selon l'invention est caractérisé en ce qu'il est obtenu par addition de Mickael de 2 à k moles d'un composé (a2) contenant un groupe alkyle fluoré et de l'hydrogène actif, à 1 mole d'un composé (a1) ayant un nombre k (k étant égal à 2 ou plus) de groupes (méth)acryloyle par molécule. Une composition de tensioactif contenant l'agent antimousse et un tensioactif à base de fluor; une composition de revêtement contenant l'agent antimousse et un tensioactif à base de fluor; et une composition de réserve contenant l'agent antimousse et un tensioactif à base de fluor sont en outre décrites.
PCT/JP2014/057288 2013-03-21 2014-03-18 Agent antimousse, composition de tensioactif, composition de revêtement, et composition de réserve Ceased WO2014148474A1 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
KR1020157025127A KR102241109B1 (ko) 2013-03-21 2014-03-18 소포제, 계면활성제 조성물, 코팅 조성물 및 레지스트 조성물
CN201480017244.9A CN105050681B (zh) 2013-03-21 2014-03-18 消泡剂、表面活性剂组合物、涂层组合物和抗蚀剂组合物
JP2014536032A JP5668899B1 (ja) 2013-03-21 2014-03-18 消泡剤、界面活性剤組成物、コーティング組成物及びレジスト組成物

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2013058132 2013-03-21
JP2013-058132 2013-03-21

Publications (1)

Publication Number Publication Date
WO2014148474A1 true WO2014148474A1 (fr) 2014-09-25

Family

ID=51580152

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2014/057288 Ceased WO2014148474A1 (fr) 2013-03-21 2014-03-18 Agent antimousse, composition de tensioactif, composition de revêtement, et composition de réserve

Country Status (5)

Country Link
JP (1) JP5668899B1 (fr)
KR (1) KR102241109B1 (fr)
CN (1) CN105050681B (fr)
TW (1) TWI582229B (fr)
WO (1) WO2014148474A1 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2019026707A (ja) * 2017-07-28 2019-02-21 Dic株式会社 粘着剤組成物、及びこれを用いた積層フィルム
JP2022040149A (ja) * 2017-07-28 2022-03-10 Dic株式会社 粘着剤組成物、及びこれを用いた積層フィルム

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP6210309B2 (ja) * 2013-12-25 2017-10-11 Dic株式会社 界面活性剤組成物、コーティング組成物及びレジスト組成物
CN108709861A (zh) * 2018-06-01 2018-10-26 廊坊立邦涂料有限公司 一种树脂混溶性的检测方法
CA3110854C (fr) * 2018-08-29 2025-04-01 Ecolab Usa Inc Composés ioniques à charges multiples dérivés de polyamines et leurs compositions et leur utilisation en tant que briseurs d'émulsion aqueuse dans des opérations pétrolières et gazières
TWI772729B (zh) * 2019-12-30 2022-08-01 林大強 抗泡組成物
CN116546754A (zh) * 2023-07-06 2023-08-04 深圳市锐舞数码科技有限公司 电子设备保护壳及其制造方法
CN117106268B (zh) * 2023-09-07 2024-04-16 杭州管康塑业有限公司 一种高抗冲高耐候pvc增强管材及其制备方法

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2005170936A (ja) * 2003-11-21 2005-06-30 Dainippon Ink & Chem Inc フッ素化アルキル基含有（メタ）アクリレートの製造方法
JP2007246696A (ja) * 2006-03-16 2007-09-27 Dainippon Ink & Chem Inc コーティング用硬化性組成物
JP2007262287A (ja) * 2006-03-29 2007-10-11 Dainippon Ink & Chem Inc コーティング組成物
JP2007262286A (ja) * 2006-03-29 2007-10-11 Dainippon Ink & Chem Inc コーティング組成物
JP2012521472A (ja) * 2009-03-25 2012-09-13 ディーエスエム アイピー アセッツ ビー．ブイ． 改善された生物付着防止コーティング

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP3226058B2 (ja) 1992-12-25 2001-11-05 大日本インキ化学工業株式会社 消泡剤、界面活性剤組成物及び洗浄剤組成物
CN100427516C (zh) * 2003-11-21 2008-10-22 大日本油墨化学工业株式会社 含氟光固化性组合物
CN102217042A (zh) * 2008-10-02 2011-10-12 高级技术材料公司 表面活性剂/消泡剂混合物用于增强硅基板的金属负载及表面钝化的应用
CN102949867A (zh) * 2012-09-19 2013-03-06 天津科创医药中间体技术生产力促进有限公司 一种高效消泡剂

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2005170936A (ja) * 2003-11-21 2005-06-30 Dainippon Ink & Chem Inc フッ素化アルキル基含有（メタ）アクリレートの製造方法
JP2007246696A (ja) * 2006-03-16 2007-09-27 Dainippon Ink & Chem Inc コーティング用硬化性組成物
JP2007262287A (ja) * 2006-03-29 2007-10-11 Dainippon Ink & Chem Inc コーティング組成物
JP2007262286A (ja) * 2006-03-29 2007-10-11 Dainippon Ink & Chem Inc コーティング組成物
JP2012521472A (ja) * 2009-03-25 2012-09-13 ディーエスエム アイピー アセッツ ビー．ブイ． 改善された生物付着防止コーティング

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2019026707A (ja) * 2017-07-28 2019-02-21 Dic株式会社 粘着剤組成物、及びこれを用いた積層フィルム
JP2022040149A (ja) * 2017-07-28 2022-03-10 Dic株式会社 粘着剤組成物、及びこれを用いた積層フィルム
JP7251607B2 (ja) 2017-07-28 2023-04-04 Dic株式会社 粘着剤組成物、及びこれを用いた積層フィルム

Also Published As

Publication number Publication date
TWI582229B (zh) 2017-05-11
JPWO2014148474A1 (ja) 2017-02-16
CN105050681A (zh) 2015-11-11
TW201441363A (zh) 2014-11-01
KR20150132158A (ko) 2015-11-25
CN105050681B (zh) 2017-12-05
KR102241109B1 (ko) 2021-04-16
JP5668899B1 (ja) 2015-02-12

Similar Documents

Publication Publication Date Title
JP6198058B2 (ja) 界面活性剤組成物、コーティング組成物及びレジスト組成物
JP5668899B1 (ja) 消泡剤、界面活性剤組成物、コーティング組成物及びレジスト組成物
JP4973966B2 (ja) 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
JP4873107B2 (ja) 含フッ素硬化性樹脂及びそれを用いた活性エネルギー線硬化性組成物
CN103502306B (zh) 含氟固化性树脂、活性能量射线固化性组合物及其固化物
JP5737553B2 (ja) 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
JP6210309B2 (ja) 界面活性剤組成物、コーティング組成物及びレジスト組成物
CN117069891A (zh) 拒液剂、活性能量射线固化性组合物、固化物及显示装置
JP6210295B2 (ja) 界面活性剤組成物、コーティング組成物及びレジスト組成物
JP2014062233A (ja) 界面活性剤、コーティング組成物及びレジスト組成物
JP5516969B2 (ja) 含フッ素硬化性樹脂及びそれを用いた活性エネルギー線硬化型組成物
CN112334501B (zh) 氟系共聚物、滑水性表面改性剂、固化性树脂组合物、和滑水性涂膜
JP2015214640A (ja) 界面活性剤、コーティング組成物及びレジスト組成物
JP2014152286A (ja) 界面活性剤、コーティング組成物及びレジスト組成物

Legal Events

Date Code Title Description
WWE Wipo information: entry into national phase

Ref document number: 201480017244.9

Country of ref document: CN

ENP Entry into the national phase

Ref document number: 2014536032

Country of ref document: JP

Kind code of ref document: A

121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 14769416

Country of ref document: EP

Kind code of ref document: A1

ENP Entry into the national phase

Ref document number: 20157025127

Country of ref document: KR

Kind code of ref document: A

NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 14769416

Country of ref document: EP

Kind code of ref document: A1