WO2012005166A1 - Solvant non inflammable et agent de traitement de surface - Google Patents

Solvant non inflammable et agent de traitement de surface Download PDF

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Publication number
WO2012005166A1
WO2012005166A1 PCT/JP2011/065047 JP2011065047W WO2012005166A1 WO 2012005166 A1 WO2012005166 A1 WO 2012005166A1 JP 2011065047 W JP2011065047 W JP 2011065047W WO 2012005166 A1 WO2012005166 A1 WO 2012005166A1
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WO
WIPO (PCT)
Prior art keywords
solvent
fluorine
mass
surface treatment
agent
Prior art date
Application number
PCT/JP2011/065047
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English (en)
Japanese (ja)
Inventor
涼 平林
房恵 石渡
彩子 藤江
Original Assignee
Ａｇｃセイミケミカル株式会社
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 Ａｇｃセイミケミカル株式会社 filed Critical Ａｇｃセイミケミカル株式会社
Priority to JP2012523838A priority Critical patent/JP5840610B2/ja
Priority to CN201180033889.8A priority patent/CN102985506B/zh
Publication of WO2012005166A1 publication Critical patent/WO2012005166A1/fr

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Classifications

    • 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
    • C09K3/00—Materials not provided for elsewhere
    • C09K3/18—Materials not provided for elsewhere for application to surfaces to minimize adherence of ice, mist or water thereto; Thawing or antifreeze materials for application to surfaces

Definitions

  • the present invention relates to a non-flammable solvent and a fluorinated surface treatment agent containing the same.
  • various base materials have fluorine-based polymers for imparting IPA repellency to a solvent (2-propanol: IPA) such as water repellency, oil repellency, and flux, and in many cases, have a perfluoroalkyl group in many cases.
  • a surface treatment agent containing a fluoropolymer in a drying solvent is applied.
  • the solvent used for this surface treating agent has good drying properties and can be a solvent for a fluoropolymer. Since the fluorine-based polymer has essentially poor solubility in a normal organic solvent, the solvent of the fluorine-based polymer is substantially a fluorine-based solvent.
  • a typical example of a fluorine-based solvent that has been used so far is a so-called chlorofluorocarbon solvent such as hydrochlorofluorocarbon (HCFC) such as dichloropentafluoropropane and dichlorofluoroethane.
  • HCFC hydrochlorofluorocarbon
  • HCFC hydrochlorofluorocarbon
  • PFC perfluorocarbons
  • hydrofluoroether is one of the recently developed fluorine-based solvents that can be used instead of the above.
  • (perfluorobutoxy) methane C 4 F 9 OCH 3
  • (perfluorobutoxy) ethane C 4 F 9 OC 2 H 5
  • 2-tetrafluoroethane CF 3 CH 2 OCF 2 CF 2 H
  • HFE has advantages such as non-flammability, good drying properties, excellent chemical and thermal stability, zero ozone depletion coefficient and relatively little global warming effect.
  • these HFEs are very expensive.
  • fluorine polymer solvent that can be obtained at low cost
  • a fluorine solvent having a benzene skeleton such as bis (trifluoromethyl) benzene.
  • most of these fluorinated solvents having a benzene skeleton are flammable.
  • a fluorine-based solvent having a flammable benzene skeleton is mixed with a non-flammable fluorine-based solvent to form a solvent for a fluorine-based polymer.
  • 1,3-di (trifluoromethyl) benzene is contained as a mixed solvent with the above HFE, HFC or the like in an amount of 5 wt% or 49.75 wt% in the total solvent (see Patent Document 2). ).
  • the present invention is an inexpensive non-flammable solvent that can be used as a solvent for a fluorine-based polymer and has a low environmental impact. Furthermore, the present invention repels various substrate surfaces that can be provided at low cost. It is an object of the present invention to provide a fluorine-based surface treatment agent that can sufficiently impart water repellency, oil repellency, and IPA repellency to an environment.
  • the mass ratio (1) / (2) is particularly preferably 80/20 to 96.25 / 3.75.
  • the non-flammable solvent may contain a solvent component other than the above (1) and (2) in an amount of 20% by mass or less in the total amount of the solvent.
  • the amount of the flammable solvent component other than (1) in the non-flammable solvent is preferably 1% by mass or less in the total amount of the solvent.
  • the non-flammable solvent component other than (2) is preferably hydrofluoroether.
  • a surface treatment agent comprising a non-flammable solvent as described above and a fluorine-containing compound as a solute.
  • the fluorine-containing compound is preferably a fluorine-containing polymer or a phosphoric acid ester compound containing a polyfluoroalkyl group.
  • the solute concentration of the surface treatment agent is preferably 20% by mass or less.
  • the kinematic viscosity of the surface treatment agent is preferably 1.0 ⁇ 10 ⁇ 5 m 2 / s or less.
  • the surface treatment agent of the present invention can be used as a solder flux creep-up preventive agent, a lubricant ooze-out preventive agent, a waterproof / moisture-proof coating agent, a resin adhesion preventive agent for electronic parts, and a mold release agent.
  • covered with the above surface treating agents can also be provided.
  • the present invention can provide an inexpensive non-flammable solvent as a solvent for the fluoropolymer.
  • water and oil repellency and IPA repellency can be sufficiently imparted to various substrate surfaces, and non-flammable, environmentally and economically superior fluorine-based surface treatment agents can be provided. It was.
  • Bis (trifluoromethyl) benzene used in the present invention is also called as xylene hexafluoride and is available as a commercial product.
  • XHF represents regioisomers o-XHF (1,2-di (trifluoromethyl) benzene), m-XHF (1,3-di (trifluoromethyl) benzene) and p-XHF (1, 4-di (trifluoromethyl) benzene) may be used, or a mixture of two or more of these may be used.
  • m-XHF is preferable as XHF.
  • HFE-347pc CF 3 CH 2 OCF 2 CF 2 H
  • HFE-347pc CF 3 CH 2 OCF 2 CHF 2
  • HFE-347 may be described as CF 3 CH 2 OCF 2 CHF 2 in a product catalog or the like.
  • the mass ratio of (1) / (2) is 50/50 to 97/3, usually 60/40 to 97/3, preferably 70/30 to 97/3.
  • the ratio is preferably 80/20 to 96.25 / 3.75, particularly preferably 85/15 to 96.25 / 3.75.
  • the amount of expensive HFE-347 used can be significantly reduced by the mass ratio of (1) / (2).
  • the total mass of (1) and (2) is preferably 80% by mass or more, more preferably 90% by mass or more, and still more preferably 95% by mass or more in the total amount of the solvent. In these ranges, the solubility of the fluorine-containing compound as the solute of the non-flammable solvent is good, and the amount of other expensive solvent such as HFE used can be suppressed.
  • the other solvent component is a solvent component having flammability other than (1)
  • it is not particularly limited as long as it is 20% by mass or less in the total amount of the solvent and does not affect the flammability. As a range, it is 1 mass% or less in the total amount of the solvent.
  • HFC and HFE which are non-flammable solvents other than (2), are preferably used because of the uniform solubility of the solute fluorine-containing compound.
  • HFE is particularly preferable.
  • HFE other than (2) include the following. C 6 F 13 OCH 3 C 6 F 13 OC 2 H 5 C 3 F 7 OCH 3 C 3 F 7 OC 2 H 5 CF 2 HCF 2 CH 2 OCF 2 CF 2 H CF 3 (OCF 2 CF 2 ) n (OCF 2 ) m OCF 2 H C 8 F 17 OCH 3 C 7 F 15 OCH 3 C 4 F 9 OCH 3 C 4 F 9 OC 2 H 5 And mixtures of these.
  • the subscripts m and n each represent an integer of 1 to 20, and the alkyl skeleton group includes a linear or branched embodiment.
  • the non-flammable solvent other than (2) is not particularly limited as long as it is 20% by mass or less based on the total amount of the solvent.
  • flammability is defined as having a flash point by performing flash point measurement according to the following procedure.
  • Each flash point measurement method shall follow the method specified in JIS-K-2265.
  • flash point measurement procedure> (A) Implementation of flash point measurement by tag sealing method. (B) When the flash point cannot be measured at a temperature of 80 ° C. or lower in (a), the flash point is measured by the Cleveland open method.
  • the surface treating agent of the present invention is formed from the non-flammable solvent as described above and a solute.
  • the solvent is defined as a liquid component having a kinematic viscosity of less than 1.0 ⁇ 10 ⁇ 5 m 2 / s at room temperature
  • the solute is a solid or kinematic viscosity at room temperature of 1.0 ⁇ 10 ⁇ 5 m. It is defined as a liquid component of 2 / s or more.
  • the surface treatment agent according to the present invention contains at least a fluorine-containing compound as a solute.
  • This fluorine-containing compound is usually a compound containing a polyfluoroalkyl group, and specific examples thereof include a fluorine-containing polymer or a fluorine-containing phosphate ester containing the group.
  • the fluoropolymer contains at least a structural unit derived from the polyfluoroalkyl group-containing compound (a).
  • This compound (a) is typically a (meth) acrylic acid compound, specifically, (meth) acrylic acid ester or (meth) acrylamide.
  • the following structure is mentioned as a compound (a).
  • CH 2 CR 1 -COX-Q 1 -Rf 1
  • R 1 is a hydrogen atom or a methyl group
  • X is —O— or —NH—
  • Q 1 is a single bond or a divalent linking group
  • Rf 1 has 1 to 20 carbon atoms. It is a polyfluoroalkyl group.
  • the divalent linking group is preferably an alkylene group having 1 to 5 carbon atoms.
  • the term “(meth) acryl” means both or one of acrylic and methacrylic. If such a compound (a) is specifically exemplified by (meth) acrylic acid ester, CH 2 ⁇ CH—COO— (CH 2 ) n — (CF 2 ) m F, CH 2 ⁇ C (CH 3 ) —COO— (CH 2 ) n — (CF 2 ) m F (In the above example, the subscript n is an integer from 0 to 4, and the subscript m is an integer from 1 to 16.) The compound (a) is not limited to these. Of these, those in which m is 1 to 6 are preferred.
  • (meth) acrylic acid ester can be suitably selected by the performance calculated
  • methacrylic acid ester is preferable when water repellency is particularly important, and acrylic acid ester is preferable when oil repellency and IPA repellency are particularly important, or when heat resistance of the film is particularly important.
  • the fluoropolymer usually contains 50 mass% or more, preferably 80 mass% or more, more preferably 90 mass% or more of the structural unit derived from the compound (a).
  • the mass% of the structural unit in a polymer is the value considered that all the raw material compounds used for superposition
  • the fluorinated polymer is a polymer composed solely of the compound (a), it may be a single homopolymer or two or more copolymers of the compound (a).
  • the fluorinated polymer when it is a copolymer, it may contain one or more structural units derived from other compounds (b).
  • the compound (b) is usually a compound that does not contain a polyfluoroalkyl group, such as (meth) acrylic acid, a (meth) acrylic acid ester having an alkyl group having 1 to 18 carbon atoms, a reactive functional group.
  • fluorine-containing phosphate ester examples include the following structures.
  • Rf 2 is a polyfluoroalkyl group having 1 to 20 carbon atoms
  • Q 2 is a single bond or a divalent linking group
  • M is a hydrogen atom, an ammonium group, a substituted ammonium group or an alkali metal atom.
  • r is an integer from 1 to 3
  • s is an integer from 0 to 2
  • r + s is 3.
  • the divalent linking group is preferably an alkylene group having 1 to 5 carbon atoms which may be substituted with an OH group.
  • fluorine-containing phosphate ester examples include the following compounds, but are not limited thereto.
  • the subscript m is an integer of 1 to 16, preferably 1 to 6.
  • the fluorine-containing phosphate ester is particularly suitable for treating a metal surface as a surface treatment agent. It is also particularly suitable when used as a release agent.
  • the surface treatment agent of the present invention can be dissolved or dispersed in the above-mentioned solvent, and does not impair the object of the present invention and does not impair the stability, performance, appearance, etc.
  • other solutes can be contained without particular limitation. Examples thereof include dimethylmethyl silicone and polyethylene glycol alkylamine.
  • diluting pH adjusters, rust inhibitors, and surface treatment agents to prevent coating surface corrosion the purpose is to control the concentration of the polymer in the liquid and to distinguish it from untreated parts.
  • Other components such as dyes, dye stabilizers, flame retardants, antifoaming agents and antistatic agents.
  • the surface treatment agent of the present invention preferably has a solute concentration of 20% by mass or less.
  • This solute means not only the whole solute in the surface treatment agent, that is, not only the fluorine-containing compound but also other solutes and other components.
  • the concentration of the fluorine-containing compound of the surface treatment agent of the present invention is preferably set as appropriate depending on the application.
  • the content is preferably 1 to 20% by mass.
  • the content is preferably 1 to 5% by mass.
  • the concentration is preferably 0.01 to 1% by mass.
  • the content is preferably 0.1 to 10% by mass.
  • the concentration of the fluorine-containing compound may be a final concentration for each application. For use in each application, even if it exceeds the high concentration, for example, 1% by mass in the case of the solder flux scooping-up inhibitor, there is no problem.
  • the fluorine-containing compound is a fluorine-containing polymer
  • a polymerization solution containing the polymer at a high concentration solid content concentration
  • the amount of the fluorine-containing compound in the total amount of the solute may vary depending on the application.
  • a lubricant preventing bleeding agent for example, in a waterproof / moisture-proof coating agent, a lubricant preventing bleeding agent, an electronic component resin adhesion preventing agent, and a solder flux creeping-up preventing agent, it is preferable that 90% by mass or more of the solute component is a fluorine-containing compound.
  • the fluorine-containing compound may be 50% by mass or less of the solute component.
  • the kinematic viscosity of the surface treatment agent of the present invention is preferably less than 1.0 ⁇ 10 ⁇ 5 m 2 / s, more preferably 5.0 ⁇ 10 ⁇ 6 m 2 / s or less. Within these kinematic viscosity ranges, the workability of the surface treatment agent is good.
  • the surface treatment agent of the present invention can be used by forming a film by applying it to a portion to which performance such as water repellency, oil repellency and IPA repellency is desired.
  • the film is formed by removing the solvent from the surface treatment agent of the present invention, and is mainly composed of the solute component of the present invention.
  • a coating method a general coating method can be adopted. For example, there are methods such as dip coating, spray coating, and roller coating.
  • the surface treatment agent of the present invention After applying the surface treatment agent of the present invention, it is preferable to perform drying at a temperature not lower than the boiling point of the solvent.
  • a temperature not lower than the boiling point of the solvent For course, when it is difficult to heat and dry due to the material of the part to be processed, it should be dried while avoiding heating.
  • what is necessary is just to select the conditions of heat processing according to the composition of the surface treating agent to apply
  • the surface treatment agent of the present invention can be applied to the treatment of various materials, among which precision equipment parts, sliding parts (motors, watches, HDDs), electrical parts (electronic circuits, substrates, electronic parts, etc.) and various resins. It is preferable to use it for the processing of molds for production. Among them, it is preferable to use the surface treatment agent of the present invention as a solder flux creeping-up inhibitor, a lubricant oozing-out preventing agent, a waterproof coating agent, a moisture-proof coating agent, an electronic component resin adhesion preventing agent, and a release agent. .
  • the fluoropolymer solution obtained in Synthesis Example 1 was diluted with each predetermined amount of solvent to a polymer concentration of 0.2%.
  • Table 2 shows the solvent composition in each surface treatment agent obtained.
  • the contact angle, kinematic viscosity and density were measured as follows. The results are shown in Table 3.
  • Table 3 [Measurement of contact angle] A glass plate was immersed in each surface treating agent of Examples 1 to 4 at room temperature for 1 minute and then dried at room temperature to obtain each glass plate having a coating of each treating agent. Next, water, IPA or n-hexadecane (n-HD) was dropped onto the coating on each glass plate, and the contact angle was measured.
  • an automatic contact angle meter OCA-20 manufactured by dataphysics
  • kinematic viscosity in 25 degreeC was measured using the Ubbelohde viscometer.
  • specific gravity measurement About each surface treating agent, the specific gravity at room temperature was measured using the standard specific gravity meter (floating).
  • the fluoropolymer solution obtained in Synthesis Example 1 was diluted to a concentration shown in Table 4 with a mixed solvent in which the mass ratio of the solvent components (1) / (2) was 75/25.
  • the contact angle, kinematic viscosity and density were measured in the same manner as in Examples 1 to 4. The results are shown in Table 4.
  • the above-mentioned flash point measurement was performed for the surface treatment agent 8 and the presence or absence of flammability was tested, it was non-flammable.
  • Table 6 shows the structures of the compounds (a1) to (b2) in Table 5.
  • the polymer 2 solution was diluted to a polymer concentration of 0.2% with a mixed solvent having a solvent component (1) / (2) mass ratio of 90/10. This is designated surface treating agent 9.
  • the polymer 3 diluted with the same conditions is used as the surface treatment agent 10.
  • the surface treating agent 11 containing the compound (P1) which is a fluorine-containing phosphate ester, and the compound (Z1) which is an additive was prepared. Table 7 summarizes each surface treatment agent.
  • Compound (P1) (F (CF 2 ) 6 —CH 2 CH (OH) CH 2 O) 2 P (O) (OH)
  • Compound (Z1) C 18 H 37 N ((C 2 H 4 O) x H) (C 2 H 4 O) y H (x + y is 20 on average)
  • the water repellency, oil repellency, and IPA repellency are sufficient for surface treatment on various substrates, have no flammability, and have a low adverse effect on the environment. Nevertheless, it has become possible to provide surface treatment agents with extremely high economic benefits.

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  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Combustion & Propulsion (AREA)
  • Materials Engineering (AREA)
  • Organic Chemistry (AREA)
  • Materials Applied To Surfaces To Minimize Adherence Of Mist Or Water (AREA)
  • Paints Or Removers (AREA)

Abstract

L'invention concerne un solvant non inflammable et peu coûteux en tant que solvant de polymère fluoré. L'invention concerne également un agent de traitement de surface à base de fluor qui permet de conférer de manière suffisante à la surface d'un matériau de base des propriétés hydrofuges, oléofuges et d'imperméabilité au propanol-2, qui est non inflammable, et qui se révèle excellent aussi bien du point de vue environnemental qu'économique. Plus précisément, l'invention concerne un solvant non inflammable, et un agent de traitement de surface à base de fluor contenant ce solvant lequel solvant contient (1) un bis(trifluorométhyl)benzène et (2) CF3CH2OCF2CF2H, selon un rapport massique de (1)/(2)=50/50 à 97/3, et dont la quantité de la somme des deux est supérieure ou égale à 80% en masse de la quantité totale de solvant.
PCT/JP2011/065047 2010-07-09 2011-06-30 Solvant non inflammable et agent de traitement de surface WO2012005166A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
JP2012523838A JP5840610B2 (ja) 2010-07-09 2011-06-30 非引火性溶媒および表面処理剤
CN201180033889.8A CN102985506B (zh) 2010-07-09 2011-06-30 不燃性溶剂和表面处理剂

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2010156968 2010-07-09
JP2010-156968 2010-07-09

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WO2012005166A1 true WO2012005166A1 (fr) 2012-01-12

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JP (1) JP5840610B2 (fr)
CN (1) CN102985506B (fr)
WO (1) WO2012005166A1 (fr)

Cited By (5)

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WO2013168763A1 (fr) * 2012-05-11 2013-11-14 ダイキン工業株式会社 Composition de revêtement pour étanchéifier à l'eau et étanchéifier à l'humidité
CN104220541A (zh) * 2012-04-02 2014-12-17 大金工业株式会社 耐久型防水-防湿性涂敷组合物
JP2018177857A (ja) * 2017-04-04 2018-11-15 Ａｇｃセイミケミカル株式会社 混合溶媒および表面処理剤
JP2020029533A (ja) * 2018-08-24 2020-02-27 Ａｇｃセイミケミカル株式会社 非引火性混合溶剤およびこれを含む表面処理剤
JP2021095479A (ja) * 2019-12-16 2021-06-24 Ａｇｃセイミケミカル株式会社 表面処理組成物

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CN106939064B (zh) * 2016-12-28 2019-05-14 衢州氟硅技术研究院 一种包含全氟聚醚活性成分的组合物
CN112045909A (zh) * 2020-06-16 2020-12-08 上海力太化学有限公司 一种环保高闪点聚氨酯脱模剂

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Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN104220541A (zh) * 2012-04-02 2014-12-17 大金工业株式会社 耐久型防水-防湿性涂敷组合物
WO2013168763A1 (fr) * 2012-05-11 2013-11-14 ダイキン工業株式会社 Composition de revêtement pour étanchéifier à l'eau et étanchéifier à l'humidité
JP2013253240A (ja) * 2012-05-11 2013-12-19 Daikin Industries Ltd 防水・防湿用コーティング組成物
CN104271690A (zh) * 2012-05-11 2015-01-07 大金工业株式会社 防水、防湿用涂料组合物
JP2018177857A (ja) * 2017-04-04 2018-11-15 Ａｇｃセイミケミカル株式会社 混合溶媒および表面処理剤
JP2020029533A (ja) * 2018-08-24 2020-02-27 Ａｇｃセイミケミカル株式会社 非引火性混合溶剤およびこれを含む表面処理剤
JP7257119B2 (ja) 2018-08-24 2023-04-13 Ａｇｃセイミケミカル株式会社 非引火性混合溶剤およびこれを含む表面処理剤
JP2021095479A (ja) * 2019-12-16 2021-06-24 Ａｇｃセイミケミカル株式会社 表面処理組成物
JP7416612B2 (ja) 2019-12-16 2024-01-17 Ａｇｃセイミケミカル株式会社 表面処理組成物

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JPWO2012005166A1 (ja) 2013-09-02
CN102985506B (zh) 2014-10-08
JP5840610B2 (ja) 2016-01-06
CN102985506A (zh) 2013-03-20

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