WO2023204021A1 - Composé, composition, agent de traitement de surface, procédé de fabrication d'article et article - Google Patents

Composé, composition, agent de traitement de surface, procédé de fabrication d'article et article Download PDF

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Publication number
WO2023204021A1
WO2023204021A1 PCT/JP2023/013998 JP2023013998W WO2023204021A1 WO 2023204021 A1 WO2023204021 A1 WO 2023204021A1 JP 2023013998 W JP2023013998 W JP 2023013998W WO 2023204021 A1 WO2023204021 A1 WO 2023204021A1
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WO
WIPO (PCT)
Prior art keywords
group
compound
carbon atoms
surface treatment
chain
Prior art date
Application number
PCT/JP2023/013998
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English (en)
Japanese (ja)
Inventor
弘毅 渡邉
元志 青山
Original Assignee
Ａｇｃ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株式会社 filed Critical Ａｇｃ株式会社
Publication of WO2023204021A1 publication Critical patent/WO2023204021A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic System
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
    • 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
    • C—CHEMISTRY; METALLURGY
    • C23—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
    • C23C—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; SURFACE TREATMENT OF METALLIC MATERIAL BY DIFFUSION INTO THE SURFACE, BY CHEMICAL CONVERSION OR SUBSTITUTION; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL
    • C23C14/00—Coating by vacuum evaporation, by sputtering or by ion implantation of the coating forming material
    • C23C14/06—Coating by vacuum evaporation, by sputtering or by ion implantation of the coating forming material characterised by the coating material
    • C23C14/12—Organic material

Definitions

  • the two or more chains A When two or more chains A are bonded to a reactive silyl group via a linking group, the two or more chains A may be bonded to the same atom constituting the linking group, or may be bonded to different atoms. good.
  • the two or more reactive silyl groups When two or more reactive silyl groups are bonded to chain Z and chain A via a linking group, the two or more reactive silyl groups may be bonded to the same atom constituting the linking group, or may be different from each other. May be bonded to atoms. From the viewpoint of ease of synthesis, two or more reactive silyl groups are preferably bonded to different atoms constituting the linking group.
  • the number of chains Z in the compound of the present disclosure may be 1 or more, and from the viewpoint of obtaining a surface treated layer with excellent wear resistance, the number is preferably 1 to 3, more preferably 1 to 2, and even more preferably 1.
  • the compound of the present disclosure may have only a polydialkylsiloxane residue as the chain Z, may have only an alkylene chain having 10 or more carbon atoms, or may have a polydialkylsiloxane residue and an alkylene chain having 10 or more carbon atoms. It may have both chains. From the viewpoint of ease of synthesis, it is preferable that the chain Z is only a polydialkylsiloxane residue or only an alkylene chain having 10 or more carbon atoms.
  • the compound of the present disclosure is preferably a compound represented by the following formula (1) from the viewpoint of forming a surface treatment layer that has both water repellency and oil repellency.
  • linking group that is a combination of two or more of the above linking groups include an ester bond, a thioester bond, an amide bond, and a sulfonamide bond.
  • Combinations of the above substituents and linking groups include a combination of a hydroxy group, a carbonyl group, and an alkylene group (for example, a combination of a carboxy group and an alkylene group), a combination of an amino group and a carbonyl group, and a combination of an amino group and a carbonyl group.
  • the divalent linking groups represented by L 3 and L 4 include alkylene groups, carbonyl groups, ether bonds, thioether bonds, sulfonyl groups, -NR 4 -, -SiR 4 2 -, and combinations of two or more of these.
  • the following groups are mentioned.
  • the above R 4 is a hydrogen atom or a hydrocarbon group.
  • examples of the group that is a combination of two or more of the above-mentioned groups include an ester bond, a thioester bond, an amide bond, a sulfonamide bond, a combination of an alkylene group and an ether bond, and the like.
  • the alkylene group represented by L 6 may be either linear or branched, with linear being preferred.
  • the number of carbon atoms in the alkylene group is, for example, 1 to 6, preferably 1 to 4, and more preferably 2 to 3.
  • L 5 is a carbon atom or a group in which the remaining bond is bonded to a hydrogen atom or a substituent
  • L 6 is preferably a single bond or an alkylene group having 1 to 4 carbon atoms, and more preferably a single bond.
  • two or more (-Si(R 1 ) n L 2 3-n ) contained in the compound represented by formula (1) may be the same or different from each other. Good too.
  • Q a is a single bond or a divalent linking group
  • X 31 is a group having a single bond, an alkylene group, a carbon atom, a nitrogen atom, a silicon atom, a 2- to 8-valent organopolysiloxane residue, or a (h+i+1)-valent ring
  • Q b is a single bond or a divalent linking group
  • R 31 is a hydrogen atom, a hydroxyl group or an alkyl group
  • h is an integer of 1 or more
  • i is an integer of 0 or more
  • the definitions and specific examples of R 1 , L 2 , and n are the same as the definitions and specific examples of each symbol in the reactive silyl group.
  • Examples of groups combining two or more of the above include -OC(O)-, -C(O)O-, -C(O)S-, -C(O)N(R d )- , -N(R d )C(O)-, -N(R d )C(O)N(R d )-, -N(R d )C(O)O-, -OC(O)N( R d )-, -SO 2 N(R d )-, -N(R d )SO 2 -, -C(O)N(R d )-, -N(R d )C(O )-, an alkylene group having an etheric oxygen atom, an alkylene group having -OC(O)-, an alkylene group having -C(O)O-, a -C(O)S-alkylene group, - Examples include an alkylene group having SO 2 N(R
  • Q b2 is an alkylene group or a group having a divalent organopolysiloxane residue, an ether oxygen atom, or -NH- between carbon atoms of an alkylene group having 2 or more carbon atoms.
  • the number of carbon atoms in the alkylene group represented by Q b2 is preferably 1 to 30, more preferably 1 to 20, even more preferably 2 to 20, may be 2 to 10, or may be 2 to 6. . Examples include 2, 3, 8, 9, and 11. Further, the number of carbon atoms may be 1 to 10.
  • group (3-1A-5) include the following groups.
  • * represents the bonding position with L 6 in formula (3-1).
  • Z c is a (w3+w4+1)-valent hydrocarbon group.
  • w3 is an integer of 4 or more.
  • w4 is an integer greater than or equal to 0.
  • the definitions and preferred ranges of Q e , s4, Q a4 , t4, Q b4 , and u4 are the same as the definitions of each symbol in group (3-1A-4).
  • the number of carbon atoms in the alkyl group of R e1 , R e2 or R e3 is preferably 1 to 6, more preferably 1 to 3, and even more preferably 1 to 2 from the viewpoint of ease of producing compound (3-2).
  • the number of carbon atoms in the alkyl group portion of the acyloxy group of R e2 is preferably 1 to 6, more preferably 1 to 3, and even more preferably 1 to 2, from the viewpoint of ease of producing compound (3-2).
  • h1 is preferably from 2 to 6, more preferably from 2 to 4, and even more preferably from 2 to 4, from the viewpoint of facilitating the production of compound (3-2) and from the viewpoint of further improving the abrasion resistance of the surface treatment layer.
  • h2 is preferably 2 to 6, more preferably 2 to 4, even more preferably 2 or 3, from the viewpoint of easy production of compound (3-2) and from the viewpoint of further excellent wear resistance of the surface treatment layer. .
  • Examples of the compound (3-2) include compounds of the following formula.
  • the compound of the following formula is preferred from the viewpoints of easy industrial production, ease of handling, and superior abrasion resistance of the surface treatment layer.
  • R t in the compound of the following formula is (T 1 -Z-L 3 ) or (T 2 -AL 4 ) in the above-mentioned formula (3-2), and at least one of the two or more R t One is (T 1 -Z-L 3 ), and at least one other is (T 2 -A-L 4 ).
  • the content of the liquid medium is preferably 60 to 99.999% by mass, more preferably 80 to 99.99% by mass, and even more preferably 90 to 99.9% by mass, based on the total amount of the composition of the present disclosure.
  • the content of the liquid medium may be 90-99.99% by weight, 95-99% by weight, based on the total amount of the composition of the present disclosure. It may be .98% by mass, 97 to 99.97% by mass, or 98 to 99.95% by mass.
  • the composition of the present disclosure may contain only one type of liquid medium, or may contain two or more types.
  • Group 1 elements of the periodic table mean lithium, sodium, potassium, rubidium, and cesium.
  • Group 1 elements lithium, sodium, and potassium are used because they enable the surface treatment layer to be formed more uniformly on the underlayer without defects, and from the viewpoint of suppressing variations in the composition of the underlayer between samples.
  • the underlayer may contain two or more types of Group 1 elements.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Combustion & Propulsion (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Mechanical Engineering (AREA)
  • Metallurgy (AREA)
  • Polyethers (AREA)

Abstract

L'invention concerne un composé contenant au moins un élément choisi dans le groupe constitué par les résidus de polydialkylsiloxane et les chaînes alkylène en C10 ou plus, une chaîne polyoxyalkylène et un groupe silyle réactif ; une composition et un agent de traitement de surface contenant ledit composé ; et un article et un procédé de fabrication d'un article dans lequel ledit agent de traitement de surface est utilisé.
PCT/JP2023/013998 2022-04-19 2023-04-04 Composé, composition, agent de traitement de surface, procédé de fabrication d'article et article WO2023204021A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2022-069031 2022-04-19
JP2022069031 2022-04-19

Publications (1)

Publication Number Publication Date
WO2023204021A1 true WO2023204021A1 (fr) 2023-10-26

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WO (1) WO2023204021A1 (fr)

Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4005117A (en) * 1975-04-22 1977-01-25 The Procter & Gamble Company Organosilane compounds
JPH01268609A (ja) * 1988-04-19 1989-10-26 Toshiba Silicone Co Ltd 海棲生物付着防止剤
JP2017058452A (ja) * 2015-09-15 2017-03-23 コニカミノルタ株式会社 静電潜像現像用トナーおよびその製造方法
KR101719340B1 (ko) * 2016-01-27 2017-03-23 제이에스아이실리콘주식회사 지문 돋보임 방지 피막용 친수성 및 친유성 기 실리콘 결합제 및 이의 제조 방법
KR20180015361A (ko) * 2016-08-03 2018-02-13 금호타이어 주식회사 타이어용 고무 조성물
JP2018150530A (ja) * 2017-03-09 2018-09-27 三星電子株式会社Ｓａｍｓｕｎｇ Ｅｌｅｃｔｒｏｎｉｃｓ Ｃｏ．，Ｌｔｄ． 高分子組成物、高分子複合体および光学フィルム
KR20190084741A (ko) * 2018-01-09 2019-07-17 주식회사 쎄코 친수성 다중 코팅필름
JP2021516226A (ja) * 2018-03-19 2021-07-01 エービーシーアール ラボラトリオス，エセ．エレ． 有機官能性シロキサン、その製造方法、ならびに、充填材および表面の処理のためのその使用

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4005117A (en) * 1975-04-22 1977-01-25 The Procter & Gamble Company Organosilane compounds
JPH01268609A (ja) * 1988-04-19 1989-10-26 Toshiba Silicone Co Ltd 海棲生物付着防止剤
JP2017058452A (ja) * 2015-09-15 2017-03-23 コニカミノルタ株式会社 静電潜像現像用トナーおよびその製造方法
KR101719340B1 (ko) * 2016-01-27 2017-03-23 제이에스아이실리콘주식회사 지문 돋보임 방지 피막용 친수성 및 친유성 기 실리콘 결합제 및 이의 제조 방법
KR20180015361A (ko) * 2016-08-03 2018-02-13 금호타이어 주식회사 타이어용 고무 조성물
JP2018150530A (ja) * 2017-03-09 2018-09-27 三星電子株式会社Ｓａｍｓｕｎｇ Ｅｌｅｃｔｒｏｎｉｃｓ Ｃｏ．，Ｌｔｄ． 高分子組成物、高分子複合体および光学フィルム
KR20190084741A (ko) * 2018-01-09 2019-07-17 주식회사 쎄코 친수성 다중 코팅필름
JP2021516226A (ja) * 2018-03-19 2021-07-01 エービーシーアール ラボラトリオス，エセ．エレ． 有機官能性シロキサン、その製造方法、ならびに、充填材および表面の処理のためのその使用

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