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US-20260125403-A1 - COMPOUND, METHOD FOR MANUFACTURING COMPOUND, COMPOSITION, SURFACE TREATMENT AGENT, ARTICLE, AND METHOD FOR MANUFACTURING ARTICLE

US20260125403A1US 20260125403 A1US20260125403 A1US 20260125403A1US-20260125403-A1

Abstract

A new compound capable of forming a surface-treated layer having excellent abrasion resistance and a method for manufacturing such a compound, a composition and a surface treatment agent comprising such a new compound, and an article including a surface-treated layer having excellent abrasion resistance and a method for manufacturing such an article are provided. A compound represented by below-shown Formula (1) or Formula (2) Note that each symbol in the formulas is the same as that described in the specification.

Inventors

  • Koki Watanabe
  • Yosuke Takeda
  • Shimpei MORITA
  • Kumiko Suwa
  • Ryohei YAMAGUCHI

Assignees

  • AGC Inc.

Dates

Publication Date
20260507
Application Date
20251218
Priority Date
20230623

Claims (20)

  1. 1 . A compound represented by below-shown Formula (1) or Formula (2) where R 1 is each independently (R 11 ) 3 Si—, a monovalent cyclic polysiloxane residue, or a monovalent cage-like polysiloxane residue, R 11 is each independently a hydrocarbon group or a trialkylsilyloxy group, Q 1 is each independently an oxygen atom or an alkylene group, R 2 is each independently a hydrocarbon group, R 3 is each independently a hydrocarbon group, R 4 is each independently a hydrocarbon group or R 1 -Q 1 -(SiR 2 2 —O) p1 —, p1 is each independently a number of 0 to 500, p2 is a number of 0 to 500, q1 is an integer of 1 to 3, q2 is an integer of 0 to 2, q1+q2 is 3, Q 2 is each independently a single bond or a divalent linking group, Z 1 is each independently an alkylene group having a number of carbon atoms of 7 to 100, L 1 is each independently a hydrolyzable group, a group having a hydrolyzable group, or a hydroxyl group, and n is each independently an integer of 0 to 2.
  2. 2 . The compound according to claim 1 , wherein Z 1 is an alkylene group having a number of carbon atoms of 21 to 60.
  3. 3 . The compound according to claim 1 , wherein Q 2 is represented by below-shown Formula (Q1) where: a Q 10 side is connected to Si, a Q 11 side is connected to Z 1 , r1 is 0 or 1, r2 is 0 or 1, r3 is 0 or 1, when r1, r2 and r3 are all 0, Q 2 is a single bond, Q 10 is an oxygen atom or an alkylene group, R 5 is —(SiR 6 2 —O) p3 —SiR 6 2 —, R 6 is each independently a hydrocarbon group, p3 is a number of 0 to 100, Q 11 is a hydrocarbon group which may have a bond selected from —C(═O)NR a1 —, —C(═O)S—, —C(═O)—, —C(═O)O—, —NR a1 —, —O—, and —S— between carbon atoms, at an end on a R 5 side, or at an end on a Z 1 side, and R a1 is each independently a hydrogen atom, a hydrocarbon group having a number of carbon atoms of 1 to 6, or a phenyl group, where there is no alkylene group at an end on the Z 1 side.
  4. 4 . A compound represented by below-shown Formula (11) where R 1 is (R 11 ) 3 Si—, R 11 is each independently a hydrocarbon group or a trialkylsilyloxy group, Q 1 is an oxygen atom or an alkylene group, R 2 is each independently a hydrocarbon group, R 3 is each independently a hydrocarbon group, Q 2 is each independently a single bond or a divalent linking group, Z 1 is each independently an alkylene group having a number of carbon atoms of 7 to 100, L 1 is each independently a hydrolyzable group, a group having a hydrolyzable group, or a hydroxyl group, and n is each independently an integer of 0 to 2.
  5. 5 . The compound according to claim 4 , wherein Z 1 is an alkylene group having a number of carbon atoms of 21 to 60.
  6. 6 . The compound according to claim 4 , wherein Q 2 is represented by below-shown Formula (Q1) where a Q 10 side is connected to Si, a Q 11 side is connected to Z 1 , r1 is 0 or 1, r2 is 0 or 1, r3 is 0 or 1, when r1, r2 and r3 are all 0, Q 2 is a single bond, Q 10 is an oxygen atom or an alkylene group, R 5 is —(SiR 6 2 —O) p3 —SiR 6 2 —, R 6 is each independently a hydrocarbon group, p3 is a number of 0 to 100, Q 11 is a hydrocarbon group which may have a bond selected from —C(═O)NR a1 —, —C(═O)S—, —C(═O)—, —C(═O)O—, —NR a1 —, —O—, and —S— between carbon atoms, at an end on a R 5 side, or at an end on a Z 1 side, and R a1 is each independently a hydrogen atom, a hydrocarbon group having a number of carbon atoms of 1 to 6, or a phenyl group, where there is no alkylene group at an end on the Z 1 side.
  7. 7 . A composition comprising two or more compounds represented by below-shown Formula (1), comprising: a compound (1A) in which R 1 is each independently (R 11 ) 3 Si—, and R 11 is each independently a hydrocarbon group, and a compound (1B) in which: R 1 is each independently (R 11 ) 3 Si—; two or more of three R 11 are trialkylsilyloxy groups; and a remainder is a hydrocarbon group, where R 1 is each independently (R 11 ) 3 Si—, R 11 is each independently a hydrocarbon group or a trialkylsilyloxy group, Q 1 is each independently an oxygen atom or an alkylene group, R 2 is each independently a hydrocarbon group, R 3 is each independently a hydrocarbon group, p1 is each independently a number of 0 to 500, q1 is an integer of 1 to 3, q2 is an integer of 0 to 2, q1+q2 is 3, Q 2 is each independently a single bond or a divalent linking group, Z 1 is each independently an alkylene group having a number of carbon atoms of 7 to 100, L 1 is each independently a hydrolyzable group, a group having a hydrolyzable group, or a hydroxyl group, and n is each independently an integer of 0 to 2.
  8. 8 . The composition according to claim 7 , comprising the compound (1A) and the compound (1B) in a mass ratio of from 50 to 99:50 to 1.
  9. 9 . A composition comprising the compound according to claim 1 , and a liquid medium.
  10. 10 . A surface treatment agent comprising the compound according to claim 1 .
  11. 11 . A surface treatment agent comprising the compound according to claim 1 , and a liquid medium.
  12. 12 . A method for manufacturing an article including a surface-treated layer formed on a substrate by performing a surface treatment on the substrate by using a surface treatment agent comprising the compound according to claim 1 .
  13. 13 . An article comprising a substrate, and a surface-treated layer disposed on the substrate, a surface of the surface-treated layer being treated with a surface treatment agent comprising the compound according to claim 1 .
  14. 14 . The article according to claim 13 , wherein the article is an optical member.
  15. 15 . The article according to claim 13 , wherein the article is a display or a touch panel.
  16. 16 . A method for manufacturing a compound according to claim 1 , comprising reacting a compound represented by below-shown Formula (3) or a compound represented by below-shown Formula (4) with a compound represented by below-shown Formula (5) or a compound represented by below-shown Formula (6) in presence of a transition metal compound where R 1 is each independently (R 11 ) 3 Si—, a monovalent cyclic polysiloxane residue, or a monovalent cage-like polysiloxane residue, R 11 is each independently a hydrocarbon group or a trialkylsilyloxy group, Q 1 is each independently an oxygen atom or an alkylene group, R 2 is each independently a hydrocarbon group, R 4 is each independently a hydrocarbon group or R 1 -Q 1 -(SiR 2 2 —O) p1 —, p1 is each independently a number of 0 to 500, p2 is a number of 0 to 500, q1 is an integer of 1 to 3, q2 is an integer of 0 to 2, q1+q2 is 3, Q 2 is each independently a single bond or a divalent linking group, Z 3 is each independently an alkylene group, G 1 is each independently a halogen atom or a sulfonic acid ester group which may be substituted with a halogen atom, R 7 is each independently a hydrocarbon group having a carbon-carbon double bond, X is a halogen atom, and a total number of carbon atoms of Z 3 and R 7 is 7 to 100.
  17. 17 . The method for manufacturing a compound according to claim 16 , wherein a compound represented by above-shown Formula (3) or a compound represented by above-shown Formula (4) is reacted with a compound represented by above-shown Formula (5) or a compound represented by above-shown Formula (6) by using the compound represented by above-shown Formula (5) or (6) in an amount three equivalents or more of an amount of the compound represented by above-shown Formula (3) or (4).
  18. 18 . A compound represented by below-shown Formula (7) or Formula (8), where R 1 is each independently (R 11 ) 3 Si—, a monovalent cyclic polysiloxane residue, or a monovalent cage-like polysiloxane residue, R 11 is each independently a hydrocarbon group or a trialkylsilyloxy group, Q 1 is each independently an oxygen atom or an alkylene group, R 2 is each independently a hydrocarbon group, R 4 is each independently a hydrocarbon group or R 1 -Q 1 -(SiR 2 2 —O) p1 —, R 20 is each independently a vinyl group, p1 is each independently a number of 0 to 500, p2 is a number of 0 to 500, q1 is an integer of 1 to 3, q2 is an integer of 0 to 2, q1+q2 is 3, Q 2 is each independently a single bond or a divalent linking group, and Z 4 is each independently an alkylene group having a number of carbon atoms of 5 to 98.
  19. 19 . A composition comprising the composition according to claim 7 , and a liquid medium.
  20. 20 . A surface treatment agent comprising the composition according to claim 7 .

Description

INCORPORATION BY REFERENCE This application is based upon and claims the benefit of priority from Japanese Patent Application 2023-103355 filed on Jun. 23, 2023, Japanese Patent Application 2023-150604 filed on Sep. 15, 2023, Japanese Patent Application 2024-60422 filed on Apr. 3, 2024, and PCT application No. PCT/JP2024/022675 filed on Jun. 21, 2024, the disclosure of which are incorporated herein in its entirety by reference. BACKGROUND In recent years, there has been a demand for a technique for preventing the surface of an article from being stained with fingerprints, and a technique for facilitating the removal of dirt in order to improve properties of the article such as its appearance and visibility. As a specific method, a method for treating the surface of an article by using a surface treatment agent is known. Patent Literature 1 discloses, as a surface treatment agent, a specific siloxane group-containing silane compound having a divalent linear organopolysiloxane group and a hydrolyzable silyl group. [Patent Literature 1] International Patent Publication No. WO2023/017830 SUMMARY It has been desired to further improve surface treatment agents in view of abrasion resistance and the like. The present disclosure has been made in view of the above-described circumstances, and an object thereof is to provide a new compound capable of forming a surface-treated layer having excellent abrasion resistance and a method for manufacturing such a compound, a composition and a surface treatment agent containing such a new compound, and an article including a surface-treated layer having excellent abrasion resistance and a method for manufacturing such an article. The present disclosure includes the below-shown aspects. [1] A compound represented by below-shown Formula (1) or Formula (2) whereR1 is each independently (R11)3Si—, a monovalent cyclic polysiloxane residue, or a monovalent cage-like polysiloxane residue,R11 is each independently a hydrocarbon group or a trialkylsilyloxy group,Q1 is each independently an oxygen atom or an alkylene group,R2 is each independently a hydrocarbon group,R3 is each independently a hydrocarbon group,R4 is each independently a hydrocarbon group or R1-Q1-(SiR22—O)p1—,p1 is each independently a number of 0 to 500,p2 is a number of 0 to 500,q1 is an integer of 1 to 3,q2 is an integer of 0 to 2,q1+q2 is 3,Q2 is each independently a single bond or a divalent linking group,Z1 is each independently an alkylene group having a number of carbon atoms of 7 to 100,L1 is each independently a hydrolyzable group, a group having a hydrolyzable group, or a hydroxyl group, andn is each independently an integer of 0 to 2. [2] The compound described in Item [1], wherein Z1 is an alkylene group having a number of carbon atoms of 21 to 60. [3] The compound described in Item [1] or [2], wherein Q2 is represented by below-shown Formula (Q1) where:a Q10 side is connected to Si, a Q11 side is connected to Z′,r1 is 0 or 1,r2 is 0 or 1,r3 is 0 or 1,when r1, r2 and r3 are all 0, Q2 is a single bond,Q10 is an oxygen atom or an alkylene group,R5 is —(SiR62—O)p3—SiR62—,R6 is each independently a hydrocarbon group,p3 is a number of 0 to 100,Q11 is a hydrocarbon group which may have a bond selected from —C(═O)NRa1—, —C(═O)S—, —C(═O)—, —C(═O)O—, —NRa1—, —O—, and —S— between carbon atoms, at an end on a R5 side, or at an end on a Z1 side, andRa1 is each independently a hydrogen atom, a hydrocarbon group having a number of carbon atoms of 1 to 6, or a phenyl group,where there is no alkylene group at an end on the Z1 side. [4] A compound represented by below-shown Formula (11) where R1 is (R11)3Si—,R11 is each independently a hydrocarbon group or a trialkylsilyloxy group,Q1 is an oxygen atom or an alkylene group,R2 is each independently a hydrocarbon group,R3 is each independently a hydrocarbon group,Q2 is each independently a single bond or a divalent linking group,Z1 is each independently an alkylene group having a number of carbon atoms of 7 to 100,L1 is each independently a hydrolyzable group, a group having a hydrolyzable group, or a hydroxyl group, andn is each independently an integer of 0 to 2. [5] The compound described in Item [4], wherein Z1 is an alkylene group having a number of carbon atoms of 21 to 60. [6] The compound described in Item [4] or [5], wherein Q2 is represented by below-shown Formula (Q1) wherea Q10 side is connected to Si, a Q11 side is connected to Z1,r1 is 0 or 1,r2 is 0 or 1,r3 is 0 or 1,when r1, r2 and r3 are all 0, Q2 is a single bond,Q10 is an oxygen atom or an alkylene group,R5 is —(SiR62—O)p3—SiR62—,R6 is each independently a hydrocarbon group,p3 is a number of 0 to 100,Q11 is a hydrocarbon group which may have a bond selected from —C(═O)NRa1—, —C(═O)S—, —C(═O)—, —C(═O)O—, —NRa1—, —O—, and —S— between carbon atoms, at an end on a R5 side, or at an end on a Z1 side, andRa1 is each independently a hydrogen atom, a hydrocarbon group having a number of carbon atoms of 1 to 6,