JP2023057030A - Fluoropolyether group-containing epoxy compound - Google Patents

Abstract

To provide a fluoropolyether group-containing epoxy compound capable of providing a surface treatment layer with high water repellency.SOLUTION: Specifically, a fluoropolyether group-containing epoxy compound is, e.g., a compound represented by structural formula in the figure and represented by an isocyanurate structure substituted with a perfluoroether polymer and epoxy groups.SELECTED DRAWING: None

Description

The present disclosure relates to fluoropolyether group-containing epoxy compounds and compositions containing the fluoropolyether group-containing epoxy compounds.

Certain fluorine-containing compounds are known to provide excellent water repellency, oil repellency, antifouling properties, etc. when used for surface treatment of substrates. As such a fluorine-containing compound, a fluorine-containing compound having a fluoropolyether group as a functional site and an epoxy group as a reactive site is known (Patent Document 1).

JP 2014-80534 A

Although the fluorine-containing compound described in Patent Document 1 described above can impart water repellency to a substrate, there is a demand for further improvement in water repellency.

An object of the present disclosure is to provide a fluoropolyether group-containing epoxy compound capable of providing a surface treatment layer having high water repellency.

［式中：
Ｒ^Ａは、それぞれ独立して、Ｒ^Ｆ１－Ｘ^ａ－、Ｒ^Ｅ _ｍ－Ｘ^ｂ－、又は１価の基であり、
Ｒ^Ｆ１は、Ｒｆ^１－Ｒ^Ｆ－Ｏ_ｑ－であり、
Ｒ^Ｆ２は、－Ｒｆ^２ _ｐ－Ｒ^Ｆ－Ｏ_ｑ－であり、
Ｒｆ^１は、１個又はそれ以上のフッ素原子により置換されていてもよいＣ_１－１６アルキル基であり、
Ｒｆ^２は、１個又はそれ以上のフッ素原子により置換されていてもよいＣ_１－６アルキレン基であり、
Ｒ^Ｆは、それぞれ独立して、２価のフルオロポリエーテル基であり、
ｐは、０又は１であり、
ｑは、それぞれ独立して、０又は１であり、
Ｘ^ａは、それぞれ独立して、単結合又は２価の有機基であり、
Ｒ^Ｅは、それぞれ独立して、エポキシ基を含有する基であり、
Ｘ^ｂは、それぞれ独立して、シロキサン結合を含む２～９価の基であり、
ｍは、それぞれ独立して、１～８の整数である。］
で表される化合物。
［２］ Ｒ^Ｆは、それぞれ独立して、式：
－（ＯＣ_６Ｆ_１２）_ａ－（ＯＣ_５Ｆ_１０）_ｂ－（ＯＣ_４Ｆ_８）_ｃ－（ＯＣ_３Ｒ^Ｆａ _６）_ｄ－（ＯＣ_２Ｆ_４）_ｅ－（ＯＣＦ_２）_ｆ－
［式中：
Ｒ^Ｆａは、各出現においてそれぞれ独立して、水素原子、フッ素原子又は塩素原子であり、
ａ、ｂ、ｃ、ｄ、ｅ及びｆは、それぞれ独立して、０～２００の整数であって、ａ、ｂ、ｃ、ｄ、ｅ及びｆの和は１以上である。ａ、ｂ、ｃ、ｄ、ｅ又はｆを付して括弧でくくられた各繰り返し単位の存在順序は式中において任意である。］
で表される基である、上記［１］に記載の化合物。
［３］ Ｒ^Ｆａは、フッ素原子である、上記［２］に記載の化合物。
［４］ Ｒ^Ｆは、各出現においてそれぞれ独立して、下記式（ｆ１）、（ｆ２）、（ｆ３）、（ｆ４）、（ｆ５）又は（ｆ６）：
－（ＯＣ_３Ｆ_６）_ｄ－（ＯＣ_２Ｆ_４）_ｅ－ （ｆ１）
［式中、ｄは１～２００の整数であり、ｅは、０又は１である。］、
－（ＯＣ_４Ｆ_８）_ｃ－（ＯＣ_３Ｆ_６）_ｄ－（ＯＣ_２Ｆ_４）_ｅ－（ＯＣＦ_２）_ｆ－ （ｆ２）
［式中、ｃ及びｄは、それぞれ独立して、０～３０の整数であり；
ｅ及びｆは、それぞれ独立して、１～２００の整数であり；
ｃ、ｄ、ｅ及びｆの和は、１０～２００の整数であり；
添字ｃ、ｄ、ｅ又はｆを付して括弧でくくられた各繰り返し単位の存在順序は、式中において任意である。］、
－（Ｒ^６－Ｒ^７）_ｇ－ （ｆ３）
［式中、Ｒ^６は、ＯＣＦ_２又はＯＣ_２Ｆ_４であり；
Ｒ^７は、ＯＣ_２Ｆ_４、ＯＣ_３Ｆ_６、ＯＣ_４Ｆ_８、ＯＣ_５Ｆ_１０及びＯＣ_６Ｆ_１２から選択される基であるか、あるいは、これらの基から選択される２又は３つの基の組み合わせであり；
ｇは、２～１００の整数である。］、
－（Ｒ^６－Ｒ^７）_ｇ－Ｒ^ｒ－（Ｒ^７’－Ｒ^６’）_ｇ’－ （ｆ４）
［式中、Ｒ^６は、ＯＣＦ_２又はＯＣ_２Ｆ_４であり、
Ｒ^７は、ＯＣ_２Ｆ_４、ＯＣ_３Ｆ_６、ＯＣ_４Ｆ_８、ＯＣ_５Ｆ_１０及びＯＣ_６Ｆ_１２から選択される基であるか、あるいは、これらの基から独立して選択される２又は３つの基の組み合わせであり、
Ｒ^６’は、ＯＣＦ_２又はＯＣ_２Ｆ_４であり、
Ｒ^７’は、ＯＣ_２Ｆ_４、ＯＣ_３Ｆ_６、ＯＣ_４Ｆ_８、ＯＣ_５Ｆ_１０及びＯＣ_６Ｆ_１２から選択される基であるか、あるいは、これらの基から独立して選択される２又は３つの基の組み合わせであり、
ｇは、２～１００の整数であり、
ｇ’は、２～１００の整数であり、
Ｒ^ｒは、

（式中、＊は、結合位置を示す。）
である。］；
－（ＯＣ_６Ｆ_１２）_ａ－（ＯＣ_５Ｆ_１０）_ｂ－（ＯＣ_４Ｆ_８）_ｃ－（ＯＣ_３Ｆ_６）_ｄ－（ＯＣ_２Ｆ_４）_ｅ－（ＯＣＦ_２）_ｆ－ （ｆ５）
［式中、ｅは、１以上２００以下の整数であり、ａ、ｂ、ｃ、ｄ及びｆは、それぞれ独立して０以上２００以下の整数であり、また、ａ、ｂ、ｃ、ｄ、ｅ又はｆを付して括弧でくくられた各繰り返し単位の存在順序は式中において任意である。］
－（ＯＣ_６Ｆ_１２）_ａ－（ＯＣ_５Ｆ_１０）_ｂ－（ＯＣ_４Ｆ_８）_ｃ－（ＯＣ_３Ｆ_６）_ｄ－（ＯＣ_２Ｆ_４）_ｅ－（ＯＣＦ_２）_ｆ－ （ｆ６）
［式中、ｆは、１以上２００以下の整数であり、ａ、ｂ、ｃ、ｄ及びｅは、それぞれ独立して０以上２００以下の整数であり、また、ａ、ｂ、ｃ、ｄ、ｅ又はｆを付して括弧でくくられた各繰り返し単位の存在順序は式中において任意である。］
で表される基である、上記［１］～［３］のいずれか１項に記載の化合物。
［５］ Ｒｆ^１は、各出現においてそれぞれ独立して、Ｃ_１－１６パーフルオロアルキル基であり、
Ｒｆ^２は、各出現においてそれぞれ独立して、Ｃ_１－６パーフルオロアルキレン基である、
上記［１］～［４］のいずれか１項に記載の化合物。
［６］ Ｘ^ａは、それぞれ独立して、下記式：
－（ＣＸ^１２１Ｘ^１２２）_ｘ１－（Ｘ^ａ１）_ｙ１－（ＣＸ^１２３Ｘ^１２４）_ｚ１－
［式中、
Ｘ^１２１～Ｘ^１２４は、それぞれ独立して、Ｈ、Ｆ、ＯＨ、又は、－ＯＳｉ（ＯＲ^１２１）_３（式中、３つのＲ^１２１は、それぞれ独立して、炭素数１～４のアルキル基である。）であり、
Ｘ^ａ１は、－Ｃ（＝Ｏ）ＮＨ－、－ＮＨＣ（＝Ｏ）－、－Ｏ－、－Ｃ（＝Ｏ）Ｏ－、－ＯＣ（＝Ｏ）－、－ＯＣ（＝Ｏ）Ｏ－、又は、－ＮＨＣ（＝Ｏ）ＮＨ－であり、
ｘ１は０～１０の整数であり、ｙ１は０又は１であり、ｚ１は１～１０の整数である。］
で表される基である、上記［１］～［５］のいずれか１項に記載の化合物。
［７］ Ｘ^ａは、それぞれ独立して、－（ＣＨ_２）_ｍ２２－（式中、ｍ２２は１～３の整数である。）で表される基である、上記［１］～［６］のいずれか１項に記載の化合物。
［８］ Ｒ^Ｅは、それぞれ独立して、下記式：
－Ｘ^ｃ－Ｒ^Ｅ１
［式中、
Ｘ^ｃは、単結合、又は２価の基であり、
Ｒ^Ｅ１は、エポキシ基、又は脂環式エポキシ基である。］
で表される基である、上記［１］～［７］のいずれか１項に記載の化合物。
［９］ 前記脂環式エポキシ基は、下記式：

［式中、ｎは、１～５の整数である。］
で表される基である、上記［８］に記載の化合物。
［１０］ Ｘ^ｃは、下記式：
－（Ｃ_ａＨ_２ａ）_ｎ１－（Ｒ^５）_ｎ２－
［式中、
ａは、（Ｃ_ａＨ_２ａ）単位毎にそれぞれ独立して、１～６の整数であり、
Ｒ^５は、それぞれ独立して、－Ｏ－、－Ｃ（＝Ｏ）ＮＨ－、－ＮＨＣ（＝Ｏ）－、－Ｃ（＝Ｏ）Ｏ－、－ＯＣ（＝Ｏ）－、－ＯＣ（＝Ｏ）Ｏ－、又は、－ＮＨＣ（＝Ｏ）ＮＨ－であり、
ｎ１は、０～６の整数であり、
ｎ２は、０～６の整数であり、
ｎ１及びｎ２を付して括弧でくくられた各繰り返し単位の存在順序は式中において任意である。］
で表される基である、上記［８］又は［９］に記載の化合物。
［１１］ Ｘ^ｃは、下記式：
－（Ｃ_ａＨ_２ａ）_ｎ３－（Ｒ^５）_ｎ２－（Ｃ_ａＨ_２ａ）_ｎ４－
［式中、
ａは、（Ｃ_ａＨ_２ａ）それぞれ独立して、１～６の整数であり、
Ｒ^５は、－Ｏ－であり、
ｎ２は、０又は１であり、
ｎ３は、０又は１であり、
ｎ４は、０又は１であり、
ｎ２、ｎ３及びｎ４の少なくとも１つは１である。］
で表される基である、上記［８］～［１０］のいずれか１項に記載の化合物。
［１２］ Ｘ^ｂは、それぞれ独立して、下記式：
－Ｘ^ｄ－Ｒ^Ｓ－
［式中、
Ｘ^ｄは、単結合、又は２価の基であり、
Ｒ^Ｓは、２～９価のシロキサン基である。］
で表される基である、上記［１］～［１１］のいずれか１項に記載の化合物。
［１３］ Ｒ^Ｓは、下記式（ｓ１）、（ｓ２）、又は（ｓ３）：

［式中、
Ｒ^３は、それぞれ独立して、水素原子、又はＣ_１－６アルキル基であり、
Ｒ^４は、単結合、水素原子、又はＣ_１－６アルキル基であり、
ｍ１は、１～２０の整数であり、
ｍ２は、１～８の整数であり、
ｍ３は、０～１２の整数であり、
括弧でくくられた各単位の存在順序は式中において任意であり、
＊を付した結合手が、Ｘ^ｄに結合する。］
で表される基である、上記［１２］に記載の化合物。
［１４］ Ｒ^Ｓは、下記式（ｓ１）又は（ｓ３’）：

［式中、
Ｒ^３は、それぞれ独立して、水素原子、又はＣ_１－６アルキル基であり、
ｍ１は、１～２０の整数であり、
ｍ２は、３～５の整数であり、
＊を付した結合手が、Ｘ^ｄに結合する。］
で表される基である、上記［１２］又は［１３］に記載の化合物。
［１５］ Ｘ^ｄは、下記式：
－（Ｃ_ｂＨ_２ｂ）_ｒ１－（Ｒ^１０）_ｒ２－
［式中、
ｂは、（Ｃ_ｂＨ_２ｂ）単位毎にそれぞれ独立して、１～６の整数であり、
Ｒ^１０は、それぞれ独立して、－Ｏ－、－Ｃ（＝Ｏ）ＮＨ－、－ＮＨＣ（＝Ｏ）－、－Ｃ（＝Ｏ）Ｏ－、－ＯＣ（＝Ｏ）－、－ＯＣ（＝Ｏ）Ｏ－、又は、－ＮＨＣ（＝Ｏ）ＮＨ－であり
ｒ１は、０～６の整数であり、
ｒ２は、０～６の整数であり、
ｒ１及びｒ２を付して括弧でくくられた各繰り返し単位の存在順序は式中において任意である。］
で表される基である、上記［１２］～［１４］のいずれか１項に記載の化合物。
［１６］ Ｘ^ｄは、下記式：
－Ｃ_ｂＨ_２ｂ－
［式中、
ｂは、１～６の整数である。］
で表される基である、上記［１２］～［１５］のいずれか１項に記載の化合物。
［１７］ ｍは、それぞれ独立して、１～３の整数である、上記［１］～［１６］のいずれか１項に記載の化合物。
［１８］ Ｒ^Ａは、それぞれ独立して、Ｒ^Ｅ _ｍ－Ｘ^ｂ－である、上記［１］～［１７］のいずれか１項に記載の化合物。
［１９］ １種又はそれ以上の上記［１］～［１８］のいずれか１項に記載の化合物を含む、表面処理剤。
［２０］ 上記［１］～［１８］のいずれか１項に記載の化合物または上記［１９］に記載の表面処理剤；および
マトリックスを形成する組成物
を含む、硬化性組成物。
［２１］ 基材と、該基材の表面に上記［１９］に記載の表面処理剤あるいは上記［２０］に記載の硬化性組成物により形成された層とを含む物品。
［２２］ 上記物品が光学部材である、上記［２１］に記載の物品。 The present disclosure includes the following aspects.
[1] Formula (1) or Formula (2) below:

[In the formula:
each R ^A is independently R ^F1 —X ^a —, R ^E _m —X ^b —, or a monovalent group;
R ^F1 is Rf ¹ —R ^F —O _q —;
R ^F2 is -Rf ² _p -R ^F -O _q -,
Rf ¹ is a C _1-16 alkyl group optionally substituted by one or more fluorine atoms,
Rf ² is a C _1-6 alkylene group optionally substituted by one or more fluorine atoms,
R ^F is each independently a divalent fluoropolyether group,
p is 0 or 1,
each q is independently 0 or 1;
each X ^a is independently a single bond or a divalent organic group,
each R ^E is independently an epoxy group-containing group;
X ^b are each independently a divalent to 9-valent group containing a siloxane bond,
Each m is independently an integer from 1 to 8. ]
A compound represented by
[2] R ^F is each independently represented by the formula:
- (OC ₆ F ₁₂ ) _a - (OC ₅ F ₁₀ ) _b - (OC ₄ F ₈ ) _c - (OC ₃ R ^Fa ₆ ) _d - (OC ₂ F ₄ ) _e - (OCF ₂ ) _f -
[In the formula:
R ^Fa is independently at each occurrence a hydrogen atom, a fluorine atom, or a chlorine atom;
a, b, c, d, e and f are each independently integers from 0 to 200, and the sum of a, b, c, d, e and f is 1 or more. The order of existence of each repeating unit bracketed with a, b, c, d, e or f is arbitrary in the formula. ]
The compound according to the above [1], which is a group represented by
[3] The compound according to [2] above, wherein R ^Fa is a fluorine atom.
[4] R ^F is independently at each occurrence represented by the following formulas (f1), (f2), (f3), (f4), (f5) or (f6):
-(OC ₃ F ₆ ) _d -(OC ₂ F ₄ ) _e - (f1)
[In the formula, d is an integer of 1 to 200, and e is 0 or 1. ],
-(OC ₄ F ₈ ) _c -(OC ₃ F ₆ ) _d -(OC ₂ F ₄ ) _e -(OCF ₂ ) _f - (f2)
[Wherein, c and d are each independently an integer of 0 to 30;
e and f are each independently an integer from 1 to 200;
the sum of c, d, e and f is an integer from 10 to 200;
The order of existence of each repeating unit bracketed with subscript c, d, e or f is arbitrary in the formula. ],
-(R ⁶ -R ⁷ ) _g - (f3)
[wherein R ⁶ is OCF ₂ or OC ₂ F ₄ ;
R ⁷ is a group selected from OC ₂ F ₄ , OC ₃ F ₆ , OC ₄ F ₈ , OC ₅ F ₁₀ and OC ₆ F ₁₂ , or two or three groups selected from these groups. is a combination of groups;
g is an integer from 2 to 100; ],
—(R ⁶ —R ⁷ ) _g —R ^r —(R ^7′ —R ^6′ ) _g′ − (f4)
[wherein R ⁶ is OCF ₂ or OC ₂ F ₄ ;
R ⁷ is a group selected from OC ₂ F ₄ , OC ₃ F ₆ , OC ₄ F ₈ , OC ₅ F ₁₀ and OC ₆ F ₁₂ or 2 independently selected from these groups or a combination of three groups,
R ^6' is OCF ₂ or OC ₂ F ₄ ;
R ^7′ is a group selected from OC ₂ F ₄ , OC ₃ F ₆ , OC ₄ F ₈ , OC ₅ F ₁₀ and OC ₆ F ₁₂ or independently selected from these groups a combination of two or three groups,
g is an integer from 2 to 100,
g' is an integer from 2 to 100,
^Rr is

(In the formula, * indicates the binding position.)
is. ];
- (OC ₆ F ₁₂ ) _a - (OC ₅ F ₁₀ ) _b - (OC ₄ F ₈ ) _c - (OC ₃ F ₆ ) _d - (OC ₂ F ₄ ) _e - (OCF ₂ ) _f - (f5)
[Wherein, e is an integer of 1 or more and 200 or less, a, b, c, d and f are each independently an integer of 0 or more and 200 or less, and a, b, c, d, The order of existence of each repeating unit bracketed with e or f is arbitrary in the formula. ]
- (OC ₆ F ₁₂ ) _a - (OC ₅ F ₁₀ ) _b - (OC ₄ F ₈ ) _c - (OC ₃ F ₆ ) _d - (OC ₂ F ₄ ) _e - (OCF ₂ ) _f - (f6)
[Wherein, f is an integer of 1 or more and 200 or less, a, b, c, d and e are each independently an integer of 0 or more and 200 or less, and a, b, c, d, The order of existence of each repeating unit bracketed with e or f is arbitrary in the formula. ]
The compound according to any one of [1] to [3] above, which is a group represented by
[5] Rf ¹ is independently at each occurrence a C _1-16 perfluoroalkyl group;
Rf ² is independently at each occurrence a C _1-6 perfluoroalkylene group;
The compound according to any one of [1] to [4] above.
[6] X ^a is each independently represented by the following formula:
-(CX ¹²¹ X ¹²² ) _x1 -(X ^a1 ) _y1 -(CX ¹²³ X ¹²⁴ ) _z1 -
[In the formula,
X ¹²¹ to X ¹²⁴ are each independently H, F, OH or —OSi(OR ¹²¹ ) ₃ (wherein the three R ¹²¹ are each independently an alkyl group having 1 to 4 carbon atoms is.) and
X ^a1 is -C(=O)NH-, -NHC(=O)-, -O-, -C(=O)O-, -OC(=O)-, -OC(=O)O- , or -NHC(=O)NH-,
x1 is an integer of 0-10, y1 is 0 or 1, and z1 is an integer of 1-10. ]
The compound according to any one of [1] to [5] above, which is a group represented by
[7] Each of X ^a is independently a group represented by —(CH ₂ ) _m22 — (wherein m22 is an integer of 1 to 3) in the above [1] to [6] A compound according to any one of
[8] R ^E is each independently represented by the following formula:
-X ^c -R ^E1
[In the formula,
X ^c is a single bond or a divalent group,
R ^E1 is an epoxy group or an alicyclic epoxy group. ]
The compound according to any one of [1] to [7] above, which is a group represented by
[9] The alicyclic epoxy group has the following formula:

[In the formula, n is an integer of 1 to 5. ]
The compound according to [8] above, which is a group represented by
[10] X ^c is the following formula:
-(C _a H _2a ) _n1 -(R ⁵ ) _n2 -
[In the formula,
a is an integer of 1 to 6 independently for each (C _a H _2a ) unit;
R ⁵ each independently represents -O-, -C(=O)NH-, -NHC(=O)-, -C(=O)O-, -OC(=O)-, -OC( =O)O- or -NHC(=O)NH-,
n1 is an integer from 0 to 6,
n2 is an integer from 0 to 6,
The order of existence of each repeating unit bracketed with n1 and n2 is arbitrary in the formula. ]
The compound according to the above [8] or [9], which is a group represented by
[11] X ^c is the following formula:
-(C _a H _2a ) _n3 -(R ⁵ ) _n2 -(C _a H _2a ) _n4 -
[In the formula,
each a (C _a H _2a ) is independently an integer of 1 to 6;
R ⁵ is -O-,
n2 is 0 or 1,
n3 is 0 or 1,
n4 is 0 or 1,
At least one of n2, n3 and n4 is one. ]
The compound according to any one of [8] to [10] above, which is a group represented by
[12] X ^b are each independently represented by the following formula:
-X ^d -R ^S -
[In the formula,
X ^d is a single bond or a divalent group,
R ^s is a 2- to 9-valent siloxane group. ]
The compound according to any one of [1] to [11] above, which is a group represented by
[13] R ^S is represented by the following formula (s1), (s2), or (s3):

[In the formula,
each R ³ is independently a hydrogen atom or a C _1-6 alkyl group;
R ⁴ is a single bond, a hydrogen atom, or a C _1-6 alkyl group;
m1 is an integer from 1 to 20,
m2 is an integer from 1 to 8,
m3 is an integer from 0 to 12,
The order of existence of each unit enclosed in parentheses is arbitrary in the formula,
The bond marked with * is attached to ^Xd . ]
The compound according to the above [12], which is a group represented by
[14] R ^S is represented by the following formula (s1) or (s3′):

[In the formula,
each R ³ is independently a hydrogen atom or a C _1-6 alkyl group;
m1 is an integer from 1 to 20,
m2 is an integer of 3 to 5,
The bond marked with * is attached to ^Xd . ]
The compound according to the above [12] or [13], which is a group represented by
[15] X ^d has the formula:
-(C _b H _2b ) _r1 -(R ¹⁰ ) _r2 -
[In the formula,
b is an integer of 1 to 6 independently for each (C _b H _2b ) unit;
R ¹⁰ each independently represents -O-, -C(=O)NH-, -NHC(=O)-, -C(=O)O-, -OC(=O)-, -OC( =O) O- or -NHC(=O)NH- r1 is an integer of 0 to 6,
r2 is an integer from 0 to 6,
The order of existence of each repeating unit bracketed with r1 and r2 is arbitrary in the formula. ]
The compound according to any one of [12] to [14] above, which is a group represented by
[16] X ^d has the formula:
-C _{b H2b} -
[In the formula,
b is an integer from 1 to 6; ]
The compound according to any one of [12] to [15] above, which is a group represented by
[17] The compound according to any one of [1] to [16] above, wherein each m is independently an integer of 1 to 3.
[18] The compound according to any one of [1] to [17] above, wherein each R ^A is independently R ^E _m -X ^b -.
[19] A surface treatment agent comprising one or more compounds according to any one of [1] to [18] above.
[20] A curable composition comprising the compound according to any one of [1] to [18] above or the surface treating agent according to [19] above; and a matrix-forming composition.
[21] An article comprising a base material and a layer formed on the surface of the base material from the surface treating agent according to [19] or the curable composition according to [20].
[22] The article according to [21] above, wherein the article is an optical member.

The fluoropolyether group-containing epoxy compound of the present disclosure can provide a surface treatment layer with high water repellency.

As used herein, "organic group" means a monovalent group containing carbon. Unless otherwise specified, the monovalent organic group may be a hydrocarbon group or a derivative thereof. Derivatives of hydrocarbon groups have one or more of N, O, S, Si, amide, sulfonyl, sulfoxide, siloxane, carbonyl, carbonyloxy, etc. at the end of the hydrocarbon group or in the molecular chain. means a group. Moreover, a "divalent organic group" means a divalent group containing carbon. Examples of such divalent organic groups include, but are not particularly limited to, divalent groups in which one hydrogen atom is further eliminated from an organic group.

As used herein, "hydrocarbon group" means a group containing carbon and hydrogen from which one hydrogen atom has been removed from a hydrocarbon. Such hydrocarbon groups include, but are not limited to, C _1-20 hydrocarbon groups optionally substituted by one or more substituents, such as aliphatic hydrocarbon groups, aromatic A hydrocarbon group etc. are mentioned. The above "aliphatic hydrocarbon group" may be linear, branched or cyclic, and may be saturated or unsaturated. Hydrocarbon groups may also contain one or more ring structures.

As used herein, the substituent of the "hydrocarbon group" is not particularly limited, but for example, a halogen atom, C _1-6 alkyl optionally substituted by one or more halogen atoms group, C _2-6 alkenyl group, C _2-6 alkynyl group, C _3-10 cycloalkyl group, C _3-10 unsaturated cycloalkyl group, 5-10 membered heterocyclyl group, 5-10 membered unsaturated heterocyclyl groups, C _6-10 aryl groups and 5-10 membered heteroaryl groups.

The fluoropolyether group-containing epoxy compound of the present disclosure will be described below.

［式中：
Ｒ^Ａは、それぞれ独立して、Ｒ^Ｆ１－Ｘ^ａ－、Ｒ^Ｅ _ｍ－Ｘ^ｂ－、又は１価の基であり、
Ｒ^Ｆ１は、Ｒｆ^１－Ｒ^Ｆ－Ｏ_ｑ－であり、
Ｒ^Ｆ２は、－Ｒｆ^２ _ｐ－Ｒ^Ｆ－Ｏ_ｑ－であり、
Ｒｆ^１は、１個又はそれ以上のフッ素原子により置換されていてもよいＣ_１－１６アルキル基であり、
Ｒｆ^２は、１個又はそれ以上のフッ素原子により置換されていてもよいＣ_１－６アルキレン基であり、
Ｒ^Ｆは、それぞれ独立して、２価のフルオロポリエーテル基であり、
ｐは、０又は１であり、
ｑは、それぞれ独立して、０又は１であり、
Ｘ^ａは、それぞれ独立して、単結合又は２価の有機基であり、
Ｒ^Ｅは、それぞれ独立して、エポキシ基を含有する基であり、
Ｘ^ｂは、それぞれ独立して、シロキサン結合を含む２～９価の基であり、
ｍは、それぞれ独立して、１～８の整数である。］
で表される化合物を提供する。 The present disclosure provides the following formula (1) or formula (2):

[In the formula:
each R ^A is independently R ^F1 —X ^a —, R ^E _m —X ^b —, or a monovalent group;
R ^F1 is Rf ¹ —R ^F —O _q —;
R ^F2 is -Rf ² _p -R ^F -O _q -,
Rf ¹ is a C _1-16 alkyl group optionally substituted by one or more fluorine atoms,
Rf ² is a C _1-6 alkylene group optionally substituted by one or more fluorine atoms,
R ^F is each independently a divalent fluoropolyether group,
p is 0 or 1,
each q is independently 0 or 1;
each X ^a is independently a single bond or a divalent organic group,
each R ^E is independently an epoxy group-containing group;
X ^b are each independently a divalent to 9-valent group containing a siloxane bond,
Each m is independently an integer from 1 to 8. ]
to provide a compound represented by

In formula (1) above, R ^F1 is Rf ¹ —R ^F —O _q —.

In the above formula (2), R ^F2 is -Rf ² _p -R ^F -O _q -.

In the above formula, Rf ¹ is a C _1-16 alkyl group optionally substituted by one or more fluorine atoms.

The "C _1-16 alkyl group" in the C _1-16 alkyl group optionally substituted by one or more fluorine atoms may be linear or branched, preferably is a straight or branched C _1-6 alkyl group, especially a C _1-3 alkyl group, more preferably a straight chain C _1-6 alkyl group, especially a C _1-3 alkyl group.

Rf ¹ above is preferably a C _1-16 alkyl group substituted with one or more fluorine atoms, more preferably a CF ₂ H—C _1-15 perfluoroalkylene group, still more preferably It is a C _1-16 perfluoroalkyl group.

Said C _1-16 perfluoroalkyl groups may be linear or branched, preferably linear or branched C _1-6 perfluoroalkyl groups, especially C _1-3 perfluoroalkyl groups. an alkyl group, more preferably a linear C _1-6 perfluoroalkyl group, especially a C _1-3 perfluoroalkyl group, specifically -CF ₃ , -CF ₂ CF ₃ or CF ₂ CF ₂ CF ₃ be.

In the above formula, Rf ² is a C _1-6 alkylene group optionally substituted by one or more fluorine atoms.

The "C _1-6 alkylene group" in the C _1-6 alkylene group optionally substituted by one or more fluorine atoms may be linear or branched, preferably is a linear or branched C _1-3 alkylene group, more preferably a linear C _1-3 alkylene group.

Rf ² above is preferably a C _1-6 alkylene group substituted with one or more fluorine atoms, more preferably a C _1-6 perfluoroalkylene group, still more preferably C _{1- 3} is a perfluoroalkylene group.

The C _1-6 perfluoroalkylene group may be linear or branched, preferably a linear or branched C _1-3 perfluoroalkylene group, more preferably is a linear C _1-3 perfluoroalkylene group, specifically -CF ₂ -, -CF ₂ CF ₂ -, or CF ₂ CF ₂ CF ₂ -.

In the above formula, p is 0 or 1. In one aspect, p is zero. In another aspect, p is 1.

In the above formula, q is 0 or 1. In one aspect, q is zero. In another aspect q is 1.

In the above formulas (1) and (2), each ^RF is independently a divalent fluoropolyether group.

R ^F is preferably:
- (OC _h1 R ^Fa _2h1 ) _h3 - (OC _h2 R ^Fa _2h2-2 ) _h4 -
[In the formula:
R ^Fa is independently at each occurrence a hydrogen atom, a fluorine atom, or a chlorine atom;
h1 is an integer from 1 to 6,
h2 is an integer from 4 to 8,
h3 is an integer of 0 or more,
h4 is an integer of 0 or more,
However, the composition of h3 and h4 is 1 or more, preferably 2 or more, more preferably 5 or more, and the order of existence of each repeating unit bracketed with h3 and h4 is Optional. ]
It may contain a group represented by

In one aspect, R ^F can be linear or branched. R ^F preferably has the formula:
- (OC ₆ F ₁₂ ) _a - (OC ₅ F ₁₀ ) _b - (OC ₄ F ₈ ) _c - (OC ₃ R ^Fa ₆ ) _d - (OC ₂ F ₄ ) _e - (OCF ₂ ) _f -
[In the formula:
R ^Fa is independently at each occurrence a hydrogen atom, a fluorine atom, or a chlorine atom;
a, b, c, d, e and f are each independently integers from 0 to 200, and the sum of a, b, c, d, e and f is 1 or more. The order of existence of each repeating unit bracketed with a, b, c, d, e or f is arbitrary in the formula. ]
is a group represented by

^RFa is preferably a hydrogen atom or a fluorine atom, more preferably a fluorine atom.

a, b, c, d, e and f may preferably each independently be an integer from 0 to 100.

The sum of a, b, c, d, e and f is preferably 5 or more, more preferably 10 or more, for example 15 or more or 20 or more. The sum of a, b, c, d, e and f is preferably 200 or less, more preferably 100 or less, still more preferably 60 or less, and may be, for example, 50 or less or 30 or less.

These repeating units may be linear or branched. For example, the repeating units are -(OC ₆ F ₁₂ )-, -(OCF ₂ CF 2 CF ₂ CF ₂ CF ₂ CF ₂ )-, -(OCF(CF ₃ )CF ₂ CF ₂ CF _{2 CF 2} ) -, - (OCF ₂ CF (CF ₃ ) CF ₂ CF ₂ CF ₂ ) -, - (OCF ₂ CF ₂ CF (CF ₃ ) CF ₂ CF ₂ ) -, - (OCF ₂ CF ₂ CF ₂ CF (CF ₃ )CF ₂ )-, -(OCF ₂ CF ₂ CF ₂ CF ₂ CF(CF ₃ ))-, and the like. -( _OC5F10 )- _is -( _{OCF2CF2CF2CF2CF2 ) -} , -(OCF _{( CF3} ) _CF2CF2CF2 )-, _{- ( OCF2CF ( CF3} ) CF ₂ CF ₂ )-, -(OCF ₂ CF ₂ CF(CF ₃ )CF ₂ )-, -(OCF ₂ CF ₂ CF ₂ CF(CF ₃ ))- and the like. -( _OC4F8 )- is -( _{OCF2CF2CF2CF2 ) -} , -(OCF( _CF3 ) _CF2CF2 )- _, -( _OCF2CF ( _CF3 ) _{CF2 ) -} , -( _OCF2CF2CF ( _CF3 ))-, - ₍ OC( _CF3 ) _2CF2 )-, -( _OCF2C ( _CF3 ) ₂ ) _- , -(OCF( _CF3 )CF( CF ₃ ))-, -(OCF(C ₂ F ₅ )CF ₂ )- and (OCF ₂ CF(C ₂ F ₅ ))-. -(OC ₃ F ₆ )- (that is, in the above formula, R 3 ^Fa is a fluorine atom) is -(OCF ₂ CF ₂ CF ₂ )-, -(OCF(CF ₃ )CF ₂ )- and (OCF ₂ CF(CF ₃ ))-. -(OC ₂ F ₄ )- may be either -(OCF ₂ CF ₂ )- or (OCF(CF ₃ ))-.

In one aspect, the repeating unit is linear. By making the repeating unit linear, it is possible to improve the surface lubricity, friction durability, and the like of the surface treatment layer.

In one aspect, the repeat unit is branched. By branching the repeating unit, the dynamic friction coefficient of the surface treatment layer can be increased.

In one aspect, R ^F can include a ring structure.

［式中、＊は、結合位置を示す。］ The ring structure may be the following three-membered ring, four-membered ring, five-membered ring, or six-membered ring.

[In the formula, * indicates a binding position. ]

The ring structure can be preferably a four-, five- or six-membered ring, more preferably a four- or six-membered ring.

［式中、＊は、結合位置を示す。］ The repeating unit having a ring structure can preferably be the following units.

[In the formula, * indicates a binding position. ]

（式中、＊は、結合位置を示す。）
である。］；
－（ＯＣ_６Ｆ_１２）_ａ－（ＯＣ_５Ｆ_１０）_ｂ－（ＯＣ_４Ｆ_８）_ｃ－（ＯＣ_３Ｆ_６）_ｄ－（ＯＣ_２Ｆ_４）_ｅ－（ＯＣＦ_２）_ｆ－ （ｆ５）
［式中、ｅは、１以上２００以下の整数であり、ａ、ｂ、ｃ、ｄ及びｆは、それぞれ独立して０以上２００以下の整数であり、また、ａ、ｂ、ｃ、ｄ、ｅ又はｆを付して括弧でくくられた各繰り返し単位の存在順序は式中において任意である。］
－（ＯＣ_６Ｆ_１２）_ａ－（ＯＣ_５Ｆ_１０）_ｂ－（ＯＣ_４Ｆ_８）_ｃ－（ＯＣ_３Ｆ_６）_ｄ－（ＯＣ_２Ｆ_４）_ｅ－（ＯＣＦ_２）_ｆ－ （ｆ６）
［式中、ｆは、１以上２００以下の整数であり、ａ、ｂ、ｃ、ｄ及びｅは、それぞれ独立して０以上２００以下の整数であり、また、ａ、ｂ、ｃ、ｄ、ｅ又はｆを付して括弧でくくられた各繰り返し単位の存在順序は式中において任意である。］ In one embodiment, each R 1 ^F is independently a group represented by any one of the following formulas (f1) to (f6).
-(OC ₃ F ₆ ) _d -(OC ₂ F ₄ ) _e - (f1)
[Wherein, d is an integer of 1 to 200, and e is 0 or 1. ];
-(OC ₄ F ₈ ) _c -(OC ₃ F ₆ ) _d -(OC ₂ F ₄ ) _e -(OCF ₂ ) _f - (f2)
[Wherein, c and d are each independently an integer of 0 or more and 30 or less, e and f are each independently an integer of 1 or more and 200 or less,
the sum of c, d, e and f is greater than or equal to 2;
The order of existence of each repeating unit bracketed with subscript c, d, e or f is arbitrary in the formula. ];
-(R ⁶ -R ⁷ ) _g - (f3)
[wherein R ⁶ is OCF ₂ or OC ₂ F ₄ ;
R ⁷ is a group selected from OC ₂ F ₄ , OC ₃ F ₆ , OC ₄ F ₈ , OC ₅ F ₁₀ and OC ₆ F ₁₂ or 2 independently selected from these groups or a combination of three groups,
g is an integer from 2 to 100; ];
—(R ⁶ —R ⁷ ) _g —R ^r —(R ^7′ —R ^6′ ) _g′ − (f4)
[wherein R ⁶ is OCF ₂ or OC ₂ F ₄ ;
R ⁷ is a group selected from OC ₂ F ₄ , OC ₃ F ₆ , OC ₄ F ₈ , OC ₅ F ₁₀ and OC ₆ F ₁₂ or 2 independently selected from these groups or a combination of three groups,
R ^6' is OCF ₂ or OC ₂ F ₄ ;
R ^7′ is a group selected from OC ₂ F ₄ , OC ₃ F ₆ , OC ₄ F ₈ , OC ₅ F ₁₀ and OC ₆ F ₁₂ or independently selected from these groups a combination of two or three groups,
g is an integer from 2 to 100,
g' is an integer from 2 to 100,
^Rr is

(In the formula, * indicates the binding position.)
is. ];
- (OC ₆ F ₁₂ ) _a - (OC ₅ F ₁₀ ) _b - (OC ₄ F ₈ ) _c - (OC ₃ F ₆ ) _d - (OC ₂ F ₄ ) _e - (OCF ₂ ) _f - (f5)
[Wherein, e is an integer of 1 or more and 200 or less, a, b, c, d and f are each independently an integer of 0 or more and 200 or less, and a, b, c, d, The order of existence of each repeating unit bracketed with e or f is arbitrary in the formula. ]
- (OC ₆ F ₁₂ ) _a - (OC ₅ F ₁₀ ) _b - (OC ₄ F ₈ ) _c - (OC ₃ F ₆ ) _d - (OC ₂ F ₄ ) _e - (OCF ₂ ) _f - (f6)
[Wherein, f is an integer of 1 or more and 200 or less, a, b, c, d and e are each independently an integer of 0 or more and 200 or less, and a, b, c, d, The order of existence of each repeating unit bracketed with e or f is arbitrary in the formula. ]

In the above formula (f1), d is preferably an integer of 5-200, more preferably 10-100, still more preferably 15-50, for example 25-35. In one aspect, e is one. In another aspect, e is zero. (OC ₃ F ₆ ) in the above formula (f1) is preferably a group represented by (OCF ₂ CF ₂ CF ₂ ), (OCF ₂ CF(CF ₃ )) or (OCF(CF ₃ )CF ₂ ) and more preferably -(OCF ₂ CF ₂ CF ₂ ) _d -. (OC ₂ F ₄ ) in the above formula (f1) is a group represented by (OCF ₂ CF ₂ ) or (OCF(CF ₃ )), preferably represented by (OCF ₂ CF ₂ ) is the base.

In the above formula (f2), e and f are each independently an integer of preferably 5 or more and 200 or less, more preferably 10-200. Also, the sum of c, d, e and f is preferably 5 or more, more preferably 10 or more, and may be, for example, 15 or more or 20 or more. In one aspect, the above formula (f2) is preferably -(OCF ₂ CF ₂ CF ₂ CF ₂ ) _c -(OCF ₂ CF ₂ CF ₂ ) _d -(OCF ₂ CF ₂ ) _e -(OCF ₂ ) It is a group represented by _f- . In another embodiment, formula (f2) may be a group represented by -(OC ₂ F ₄ ) _e -(OCF ₂ ) _f -.

In formula (f3) above, R ⁶ is preferably OC ₂ F ₄ . In (f3) above, R ⁷ is preferably a group selected from OC ₂ F ₄ , OC ₃ F ₆ and OC ₄ F ₈ , or 2 independently selected from these groups, or A combination of three groups, more preferably a group selected from OC ₃ F ₆ and OC ₄ F ₈ . The combination of two or three groups independently selected from OC ₂ F ₄ , OC ₃ F ₆ and OC ₄ F ₈ is not particularly limited, but for example -OC ₂ F ₄ OC ₃ F ₆ -, -OC _{2F4OC4F8- , -OC3F6OC2F4- , -OC3F6OC3F6- , -OC3F6OC4F8- , -OC4F8OC4F _ _ _ _ _ _ _ _ _ _ 8- , -OC4F8OC3F6- , -OC4F8OC2F4- , -OC2F4OC2F4OC3F6- , -OC2F4OC2F4OC _ _ _ _ _ _ _ _ _ _ 4F8- , -OC2F4OC3F6OC2F4- , -OC2F4OC3F6OC3F6- , -OC2F4OC4F8OC2F4- , _ _ _ _ _ _ _ _ _ _ _ _ -OC3F6OC2F4OC2F4- , -OC3F6OC2F4OC3F6- , -OC3F6OC3F6OC2F4- , and OC4F8 _ _ _ _ _ _ _ _ _ _ _ _} OC ₂ F ₄ OC ₂ F ₄ - and the like. In the above formula (f3), g is an integer of preferably 3 or more, more preferably 5 or more. Said g is preferably an integer of 50 or less. In formula (f3) above, OC ₂ F ₄ , OC ₃ F ₆ , OC ₄ F ₈ , OC ₅ F ₁₀ and OC ₆ F ₁₂ may be linear or branched, preferably linear. is a chain. In this aspect, the above formula (f3) is preferably -(OC ₂ F ₄ -OC ₃ F ₆ ) _g - or (OC ₂ F ₄ -OC ₄ F ₈ ) _g -.

［式中、＊は、結合位置を示す。］
であり、より好ましくは

［式中、＊は、結合位置を示す。］
である。 In formula (f4) above, R ⁶ , R ⁷ and g have the same meanings as in formula (f3) above, and have the same aspects. R ^6′ , R ^7′ and g′ have the same meanings as R ⁶ , R ⁷ and g in formula (f3) above, respectively, and have the same aspects. R ^r is preferably

[In the formula, * indicates a binding position. ]
and more preferably

[In the formula, * indicates a binding position. ]
is.

In the above formula (f5), e is preferably an integer of 1 or more and 100 or less, more preferably 5 or more and 100 or less. The sum of a, b, c, d, e and f is preferably 5 or more, more preferably 10 or more, for example 10 or more and 100 or less.

In the above formula (f6), f is preferably an integer of 1 or more and 100 or less, more preferably 5 or more and 100 or less. The sum of a, b, c, d, e and f is preferably 5 or more, more preferably 10 or more, for example 10 or more and 100 or less.

In one aspect, R ^F is a group represented by the formula (f1).

In one aspect, R ^F is a group represented by the formula (f2).

In one aspect, R ^F is a group represented by the formula (f3).

In one aspect, R ^F is a group represented by the formula (f4).

In one aspect, R ^F is a group represented by the formula (f5).

In one aspect, R ^F is a group represented by the formula (f6).

In the above ^RF , the ratio of e to f (hereinafter referred to as “e/f ratio”) is 0.1 to 10, preferably 0.2 to 5, more preferably 0.2 to 2. Yes, more preferably 0.2 to 1.5, still more preferably 0.2 to 0.85. By setting the e/f ratio to 10 or less, the slipperiness, friction durability and chemical resistance (for example, durability against artificial perspiration) of the surface treatment layer obtained from this compound are further improved. The smaller the e/f ratio, the more improved the sliding property and friction durability of the surface treatment layer. On the other hand, by setting the e/f ratio to 0.1 or more, the stability of the compound can be further enhanced. The higher the e/f ratio, the more stable the compound.

In one aspect, the e/f ratio is preferably 0.2 to 0.95, more preferably 0.2 to 0.9.

In one aspect, from the viewpoint of heat resistance, the e/f ratio is preferably 1.0 or more, more preferably 1.0 to 2.0.

In the fluoropolyether group-containing compound, the number average molecular weights of R ^F1 and R ^F2 are not particularly limited, but are for example 500 to 30,000, preferably 1,500 to 30,000, more preferably 2 ,000 to 10,000. In this specification, the number average molecular weights of R ^F1 and R ^F2 are values measured by ¹⁹ F-NMR.

In another embodiment, R ^F1 and R ^F2 have a number average molecular weight of 500 to 30,000, preferably 1,000 to 20,000, more preferably 2,000 to 15,000, even more preferably 2,000. It may be -10,000, such as 3,000 to 6,000.

In another aspect, the number average molecular weight of R ^F1 and R ^F2 can be from 4,000 to 30,000, preferably from 5,000 to 10,000, more preferably from 6,000 to 10,000.

In formulas (1) and (2) above, X ^a at each occurrence is independently a single bond or a divalent organic group.

X ^a is a single bond or a divalent linking group that bonds to the isocyanuric rings of formulas (1) and (2). X ^a is preferably a single bond, an alkylene group, or a divalent group containing at least one bond selected from the group consisting of an ether bond and an ester bond, and is a single bond or an alkylene group having 1 to 10 carbon atoms. , or a divalent hydrocarbon group having 1 to 10 carbon atoms containing at least one bond selected from the group consisting of an ether bond and an ester bond is more preferable.

X ^a is represented by the following formula:
-(CX ¹²¹ X ¹²² ) _x1 -(X ^a1 ) _y1 -(CX ¹²³ X ¹²⁴ ) _z1 -
(Wherein, X ¹²¹ to X ¹²⁴ are each independently H, F, OH, or —OSi(OR ¹²¹ ) ₃ (Wherein, three R ¹²¹ each independently have 1 to is an alkyl group of 4.),
X ^a1 above is -C(=O)NH-, -NHC(=O)-, -O-, -C(=O)O-, -OC(=O)-, -OC(=O)O -, or -NHC(=O)NH- (the left side of each bond is attached to CX ¹²¹ X ¹²² ),
x1 is an integer of 0-10, y1 is 0 or 1, and z1 is an integer of 1-10. )
A group represented by is more preferable. X ^a is attached to the isocyanuric ring on the left side.

X ^a1 is preferably -O- or C(=O)O-.

X ^a is represented by the following formula:
-(CF ₂ ) _m11 -(CH ₂ ) _m12 -O-(CH ₂ ) _m13 -
(Wherein, m11 is an integer of 1 to 3, m12 is an integer of 1 to 3, and m13 is an integer of 1 to 3.)
A group represented by
-(CF ₂ ) _m14 -(CH ₂ ) _m15 -O-CH ₂ CH(OH)-(CH ₂ ) _m16 -
(Wherein, m14 is an integer of 1 to 3, m15 is an integer of 1 to 3, and m16 is an integer of 1 to 3.)
A group represented by
-(CF ₂ ) _m17 -(CH ₂ ) _m18 -
(Wherein, m17 is an integer of 1 to 3, and m18 is an integer of 1 to 3.)
A group represented by
-(CF ₂ ) _m19 -(CH ₂ ) _m20 -O-CH ₂ CH(OSi(OCH ₃ ) ₃ )-(CH ₂ ) _m21 -
(Wherein, m19 is an integer of 1 to 3, m20 is an integer of 1 to 3, and m21 is an integer of 1 to 3.)
or a group represented by
-( _CH2 ) _m22-
(Wherein, m22 is an integer of 1 to 3.)
A group represented by is particularly preferred.

Although X ^a is not particularly limited, specifically,
—CH ₂ —, —C ₂ H ₄ —, —C ₃ H ₆ —, —C ₄ H ₈ —, —C ₄ H ₈ —O—CH ₂ —, —CO—O—CH ₂ —CH(OH) —CH ₂ —, —(CF ₂ ) _n5 — (n5 is an integer of 0 to 4), —(CF ₂ ) _n5 —(CH ₂ ) _m5 — (n5 and m5 are each independently 0 4), —CF ₂ CF ₂ CH ₂ OCH ₂ CH(OH)CH ₂ —, —CF ₂ CF ₂ CH 2 _{OCH 2} CH(OSi(OCH ₃ ) ₃ )CH ₂ —
etc.

In formulas (1) and (2) above, R ^E is each independently a group containing an epoxy group.

R ^E is preferably each independently represented by the formula:
-X ^c -R ^E1
[In the formula,
X ^c is a single bond or a divalent group,
R ^E1 is an epoxy group or an alicyclic epoxy group. ]
is a group represented by

［式中、ｎは、１～５の整数、好ましくは１～３の整数である。］
で表される基である。 The cycloaliphatic epoxy group preferably has the formula:

[In the formula, n is an integer of 1 to 5, preferably an integer of 1 to 3. ]
is a group represented by

であり、特に好ましくは、

である。 In a preferred embodiment, the cycloaliphatic epoxy group is

and particularly preferably

is.

X ^c above is a single bond or a divalent group.

In one aspect, X ^c is of the formula:
-(C _a H _2a ) _n1 -(R ⁵ ) _n2 -
[In the formula,
a is an integer of 1 to 6 independently for each (C _a H _2a ) unit;
R ⁵ each independently represents -O-, -C(=O)NH-, -NHC(=O)-, -C(=O)O-, -OC(=O)-, -OC( =O)O- or -NHC(=O)NH-,
n1 is an integer from 0 to 6,
n2 is an integer from 0 to 6,
The order of existence of each repeating unit bracketed with n1 and n2 is arbitrary in the formula. ]
is a group represented by Here, X ^c is attached to ^RE1 on the right.

(C _a H _2a ) may be linear or branched, preferably linear.

a is an integer of 1-6, preferably an integer of 1-4.

R ⁵ each independently represents -O-, -C(=O)NH-, -NHC(=O)-, -C(=O)O-, -OC(=O)-, -OC( =O)O- or -NHC(=O)NH-, preferably -O-, -C(=O)NH-, -NHC(=O)-, -C(=O)O -, or -OC(=O)-, more preferably -O-.

n1 is an integer of 0-6, preferably an integer of 1-3, more preferably 1 or 2;

In one aspect, n1 is zero.

In another aspect, n1 is one.

In another aspect, n1 is two.

n2 is an integer of 0-6, preferably an integer of 0-2, more preferably 0 or 1;

In one aspect, n2 is zero.

In another aspect, n2 is one.

In one aspect, n1 is 1 and n2 is 0.

In another aspect, n1 is 2 and n2 is 1.

In a preferred embodiment, X ^c is of the formula:
-(C _a H _2a ) _n3 -(R ⁵ ) _n2 -(C _a H _2a ) _n4 -
[In the formula,
a is (C _a H _2a ) each independently an integer of 1 to 6, preferably an integer of 1 to 4;
R ⁵ is -O-,
n2 is 0 or 1,
n3 is 0 or 1,
n4 is 0 or 1,
At least one of n2, n3 and n4 is one. ]
is a group represented by

In one aspect, n2 is 0, n3 is 1 and n4 is 0.

In another aspect, n2 is 1, n3 is 1 and n4 is 1.

In the above formulas (1) and (2), each X ^b is independently a divalent to 9-valent group containing a siloxane bond.

X ^b are preferably each independently represented by the formula:
-X ^d -R ^S -
[In the formula,
X ^d is a single bond or a divalent group,
R ^s is a 2- to 9-valent siloxane group. ]
is a group represented by

［式中、
Ｒ^３は、それぞれ独立して、水素原子、又はＣ_１－６アルキル基であり、
Ｒ^４は、単結合、水素原子、又はＣ_１－６アルキル基であり、
ｍ１は、１～２０の整数であり、
ｍ２は、１～８の整数であり、
ｍ３は、０～１２の整数であり、
括弧でくくられた各単位の存在順序は式中において任意である。］
で表される基である。Ｒ^ｓは、＊の部分がＸ^ｄに結合し、他の結合手がＲ^Ｅに結合する。 R ^S is preferably the following formula (s1), (s2), or (s3):

[In the formula,
each R ³ is independently a hydrogen atom or a C _1-6 alkyl group;
R ⁴ is a single bond, a hydrogen atom, or a C _1-6 alkyl group;
m1 is an integer from 1 to 20,
m2 is an integer from 1 to 8,
m3 is an integer from 0 to 12,
The order of existence of each unit enclosed in parentheses is arbitrary in the formula. ]
is a group represented by In R ^s , the * part binds to X ^d and the other bond binds to ^RE .

Each R ³ is independently a hydrogen atom or a C _1-6 alkyl group, preferably a C _1-6 alkyl group.

R ⁴ is a single bond, a hydrogen atom, or a C _1-6 alkyl group, preferably a C _1-6 alkyl group. If it is a single bond, the Si to which ^R4 is attached is directly attached to ^RE .

The C _1-6 alkyl group for R ³ and R ⁴ above may be linear or branched, preferably linear.

The C _1-6 alkyl group is preferably a C _1-4 alkyl group, more preferably a methyl group.

m1 is an integer of 1-20, preferably an integer of 1-10, more preferably an integer of 1-6, and still more preferably an integer of 1-3.

In one aspect, m1 is one.

In another aspect, m1 is an integer from 2-10, more preferably an integer from 2-6, more preferably 2 or 3.

m2 is an integer of 1-8, preferably an integer of 1-6, more preferably an integer of 3-5.

In one aspect, m2 is 3 or 4, preferably 3.

m3 is an integer of 0-12, preferably an integer of 0-6, more preferably an integer of 0-4.

In one aspect, m3 is zero.

In another aspect, m3 is an integer from 1-12, preferably an integer from 1-6, more preferably an integer from 1-4.

In one aspect m2 is 3 or 4, preferably 3 and m3 is 0.

［式中、
Ｒ^３は、それぞれ独立して、水素原子、又はＣ_１－６アルキル基、好ましくはＣ_１－６アルキル基、より好ましくはメチル基であり、
ｍ１は、１～２０の整数、好ましくは１～１０の整数、より好ましくは１～６の整数、さらに好ましくは１～３の整数であり、
ｍ２は、３～５の整数、好ましくは３又は４、より好ましくは３である。］
で表される基である。Ｒ^ｓは、＊の部分がＸ^ｄに結合し、他の結合手がＲ^Ｅに結合する。 In a preferred embodiment, R ^S is the following formula (s1) or (s3′):

[In the formula,
each R ³ is independently a hydrogen atom or a C _1-6 alkyl group, preferably a C _1-6 alkyl group, more preferably a methyl group;
m1 is an integer of 1 to 20, preferably an integer of 1 to 10, more preferably an integer of 1 to 6, more preferably an integer of 1 to 3;
m2 is an integer of 3-5, preferably 3 or 4, more preferably 3. ]
is a group represented by In R ^s , the * part binds to X ^d and the other bond binds to ^RE .

X ^d has the formula:
-(C _b H _2b ) _r1 -(R ¹⁰ ) _r2 -
[In the formula,
b is an integer of 1 to 6 independently for each (C _b H _2b ) unit;
R ¹⁰ each independently represents -O-, -C(=O)NH-, -NHC(=O)-, -C(=O)O-, -OC(=O)-, -OC( =O) O- or -NHC(=O)NH- r1 is an integer of 0 to 6,
r2 is an integer from 0 to 6,
The order of existence of each repeating unit bracketed with r1 and r2 is arbitrary in the formula. ]
is a group represented by

(C _b H _2b ) may be linear or branched, preferably linear.

b is an integer of 1-6, preferably an integer of 2-4.

R ¹⁰ each independently represents -O-, -C(=O)NH-, -NHC(=O)-, -C(=O)O-, -OC(=O)-, -OC( =O)O- or -NHC(=O)NH-, preferably -O-, -C(=O)NH-, -NHC(=O)-, -C(=O)O -, or -OC(=O)-, more preferably -O-.

r1 is an integer of 0 to 6, preferably 1 or 2, more preferably 1;

r2 is an integer of 0 to 6, preferably 0 or 1, more preferably 0;

In one aspect, r1 is 1 and r2 is 0.

In a preferred embodiment, X ^d is of the formula:
_{-CbH2d- _}
[In the formula,
b is an integer of 1-6, preferably an integer of 2-4. ]
is a group represented by

In the above formulas (1) and (2), m is an integer of 1-8, preferably an integer of 1-6, more preferably an integer of 1-4.

In one aspect, m is one.

In another aspect, m is an integer from 2 to 4, preferably 3 or 4, more preferably 3.

In formulas (1) and (2) above, each R ^A is independently R ^F1 —X ^a —, R ^E _m —X ^b —, or a monovalent group. Such monovalent groups are groups other than R ^F1 -X ^a - and R ^E _m -X ^b -. When R ^A is R ^F1 -X ^a -, there are two R ^F1 -X ^a - in formulas (1) and (2), which may be the same or different. . Similarly, when R ^A is R ^E _m -X ^b -, there are two or more occurrences of R ^E _m -X ^b - in formulas (1) and (2), which may be the same. , can be different.

The above monovalent group is preferably a hydrogen atom or a monovalent organic group, more preferably a hydrogen atom or a C _1-6 alkyl group.

In one aspect, R ^A is R ^F1 -X ^a -. By setting R ^A to R ^F1 -X ^a -, the initial contact angle of the surface-treated layer obtained from the compound of the present disclosure can be increased.

In another aspect, R ^A is R ^E _m -X ^b -. By setting R ^A to R ^E _m -X ^b -, the durability of the surface treatment layer obtained from the compound of the present disclosure can be enhanced.

In another aspect, R ^A is a monovalent group.

The number average molecular weight of the fluoropolyether group-containing epoxy compounds represented by the above formulas (1) and (2) is not particularly limited, but is for example 1,000 to 30,000, preferably 2,000 to 20,000, more preferably 2,500 to 6,000, still more preferably 2,500 to 5,000. In this specification, the number average molecular weight of the fluoropolyether group-containing epoxy compound is a value measured by ¹⁹ F-NMR. By setting the number average molecular weight of the fluoropolyether group-containing epoxy compound within the above range, the solubility of the fluoropolyether group-containing epoxy compound in solvents is improved. In addition, the initial contact angle and friction durability of the surface treatment layer obtained from the compound can be improved.

In one aspect, the compounds of the present disclosure are compounds represented by Formula (1).

In another aspect, the compounds of the present disclosure are compounds represented by formula (2).

In another aspect, the compounds of the present disclosure are compounds of formula (1) and compounds of formula (2). That is, it is used as a mixture of the compound represented by formula (1) and the compound represented by formula (2).

In the mixture, the compound represented by formula (2) is preferably 0.1 mol% or more with respect to the total of the compound represented by formula (1) and the compound represented by formula (2). mol% or less. The lower limit of the content of the compound represented by formula (2) with respect to the total of the compound represented by formula (1) and the compound represented by formula (2) is preferably 0.1 mol%, more preferably It can be 0.2 mol %, more preferably 0.5 mol %, even more preferably 1 mol %, particularly preferably 2 mol %, especially 5 mol %. The upper limit of the content of the compound represented by formula (2) with respect to the total of the compound represented by formula (1) and the compound represented by formula (2) is preferably 35 mol%, more preferably 30 mol %, more preferably 20 mol %, even more preferably 15 mol % or 10 mol %. The compound represented by formula (2) with respect to the total of the compound represented by formula (1) and the compound represented by formula (2) is preferably 0.1 mol% or more and 30 mol% or less, more preferably 0.1 mol% or more and 20 mol% or less, more preferably 0.2 mol% or more and 10 mol% or less, even more preferably 0.5 mol% or more and 10 mol% or less, particularly preferably 1 mol% or more and 10 mol% or less Hereinafter, for example, it is 2 mol % or more and 10 mol % or less, or 5 mol % or more and 10 mol % or less. By setting the content of the compound represented by formula (2) within this range, the friction durability can be further improved.

The fluoropolyether group-containing epoxy compound of the present disclosure can be synthesized, for example, as follows.

［式中：
Ｒ^Ｆ１は、Ｒｆ^１－Ｒ^Ｆ－Ｏ_ｑ－であり、
Ｒ^Ｆ２は、－Ｒｆ^２ _ｐ－Ｒ^Ｆ－Ｏ_ｑ－であり、
Ｒｆ^１は、１個又はそれ以上のフッ素原子により置換されていてもよいＣ_１－１６アルキル基であり、
Ｒｆ^２は、１個又はそれ以上のフッ素原子により置換されていてもよいＣ_１－６アルキレン基であり、
Ｒ^Ｆは、それぞれ独立して、２価のフルオロポリエーテル基であり、
ｐは、０又は１であり、
ｑは、それぞれ独立して、０又は１であり、
Ｘ^ａは、それぞれ独立して、単結合又は２価の有機基であり、
Ｒ^Ａａは、Ｒ^Ｆ１－Ｘ^ａ－又はアリル基である。］
で表される化合物に、下記式（ｓ１ａ）、（ｓ２ａ）、又は（ｓ３ａ）：

［式中、
Ｒ^３は、それぞれ独立して、水素原子、又はＣ_１－６アルキル基であり、
Ｒ^４は、水素原子、又はＣ_１－６アルキル基であり、
ｍ１は、１～２０の整数であり、
ｍ２は、１～８の整数であり、
ｍ３は、０～１２の整数であり、
ｍ４は、２～９の整数であり、
括弧でくくられた各単位の存在順序は式中において任意である。］
で表される化合物を反応させて、下記式（１ｂ）又は（２ｂ）：

［式中：
Ｒ^Ｆ１、Ｒ^Ｆ２、及びＸ^ａは、上記と同意義であり、
Ｒ^Ｓａは、下記式：

（式中、
Ｒ^３、Ｒ^４、ｍ１、ｍ２、ｍ３、及びｍ４上記と同意義である。）
で表される基であり、
Ｒ^Ａｂは、Ｒ^Ｆ１－Ｘ^ａ－、Ｒ^Ｓａ－、又はアリル基である。］
で表される化合物を得る。 Formula (1a) or (2a) below:

[In the formula:
R ^F1 is Rf ¹ —R ^F —O _q —;
R ^F2 is -Rf ² _p -R ^F -O _q -,
Rf ¹ is a C _1-16 alkyl group optionally substituted by one or more fluorine atoms,
Rf ² is a C _1-6 alkylene group optionally substituted by one or more fluorine atoms,
R ^F is each independently a divalent fluoropolyether group,
p is 0 or 1,
each q is independently 0 or 1;
each X ^a is independently a single bond or a divalent organic group,
R ^Aa is R ^F1 —X ^a — or an allyl group. ]
to the compound represented by the following formula (s1a), (s2a), or (s3a):

[In the formula,
each R ³ is independently a hydrogen atom or a C _1-6 alkyl group;
R ⁴ is a hydrogen atom or a C _1-6 alkyl group,
m1 is an integer from 1 to 20,
m2 is an integer from 1 to 8,
m3 is an integer from 0 to 12,
m4 is an integer from 2 to 9,
The order of existence of each unit enclosed in parentheses is arbitrary in the formula. ]
By reacting a compound represented by the following formula (1b) or (2b):

[In the formula:
R ^F1 , R ^F2 , and X ^a have the same meanings as above;
R ^Sa is represented by the following formula:

(In the formula,
R ³ , R ⁴ , m1, m2, m3 and m4 have the same meanings as above. )
is a group represented by
R ^Ab is R ^F1 —X ^a —, R ^Sa —, or an allyl group. ]
A compound represented by is obtained.

Then, to the compound represented by the formula (1b) or (2b) obtained above, the following formula (3):
CH═CH ₂ —X ^c′ —R ^E1
[In the formula,
X ^c' is a single bond or a divalent group,
R ^E1 is an epoxy group or an alicyclic epoxy group. ]
can be reacted to obtain a fluoropolyether group-containing epoxy compound represented by formula (1) or (2) of the present disclosure.

Compounds of the disclosure may be used in a variety of applications. Examples of uses of the compounds of the present disclosure are now described.

The compounds of the present disclosure can be used with polymerizable coating monomers. A composition characterized by comprising a compound of the present disclosure and a polymerizable coating agent monomer is also one aspect of the present invention (sometimes referred to herein as composition (a)). Since the composition (a) has the above structure, it has a large static contact angle with water or n-hexadecane, is transparent, has excellent releasability, is resistant to fingerprints, and can be completely wiped off even if fingerprints are attached. A coating film is obtained which can be

As the polymerizable coating agent monomer, a monomer having a carbon-carbon double bond is preferred.

Examples of the polymerizable coating agent monomer include, but are not particularly limited to, monofunctional and/or polyfunctional acrylates and methacrylates (hereinafter, acrylates and methacrylates are collectively referred to as "(meth)acrylates"), It means a composition containing a compound that is a monofunctional and/or polyfunctional urethane (meth)acrylate, a monofunctional and/or polyfunctional epoxy (meth)acrylate. The composition that forms the matrix is not particularly limited, but is a composition that is generally used as a hard coating agent or an antireflection agent, such as a hard coating agent containing a polyfunctional (meth)acrylate. Alternatively, an antireflection agent containing a fluorine-containing (meth)acrylate may be used. The hard coating agent is, for example, Beamset 502H, 504H, 505A-6, 550B, 575CB, 577, 1402 (trade name) from Arakawa Chemical Industries, Ltd., Daicel Cytec Co., Ltd. as EBECRYL40 (trade name), HR300. (trade name) from Yokohama Rubber Co., Ltd. The antireflection agent is commercially available from Daikin Industries, Ltd. as OPTOOL AR-110 (trade name), for example.

Composition (a) further contains an antioxidant, a thickener, a leveling agent, an antifoaming agent, an antistatic agent, an antifogging agent, an ultraviolet absorber, pigments, dyes, inorganic fine particles such as silica, aluminum paste, and talc. , glass frit, fillers such as metal powder, and polymerization inhibitors such as butylated hydroxytoluene (BHT) and phenothiazine (PTZ).

The composition (a) may further contain a urethanization catalyst such as a tin-based catalyst, a titanium-based catalyst, a zirconia-based catalyst, a bismuth-based catalyst, or an organic amine-based catalyst.

Examples of the tin-based catalyst include di-n-butyltin (IV) dilaurate.
Examples of the titanium-based catalyst include titanium diisopropoxybis(ethylacetoacetate), titanium tetra-n-butoxide, titanium tetra-2-ethylhexoxide, and titanium tetraacetylacetonate.
Examples of the zirconia-based catalyst include zirconium tetraacetylacetonate, zirconium tetra-n-butoxide, and zirconium dibutoxybis(ethylacetoacetate).
Examples of the bismuth-based catalyst include bismuth tris(2-ethylhexanoate).
Examples of the organic amine-based catalyst include diazabicycloundecene.

Composition (a) preferably further comprises a solvent. Examples of the solvent include fluorine-containing organic solvents and non-fluorine-containing organic solvents.

Examples of the fluorine-containing organic solvent include perfluorohexane, perfluorooctane, perfluorodimethylcyclohexane, perfluorodecalin, perfluoroalkylethanol, perfluorobenzene, perfluorotoluene, perfluoroalkylamine (Fluorinert (trade name) etc.), perfluoroalkyl ether, perfluorobutyltetrahydrofuran, polyfluoroaliphatic hydrocarbon (Asahiklin AC6000 (trade name)), hydrochlorofluorocarbon (Asahiklin AK-225 (trade name), etc.), hydrofluoroether (Novec (trade name), HFE-7100 (trade name), HFE-7300 (trade name), etc.), 1,1,2,2,3,3,4-heptafluorocyclopentane, fluorine-containing alcohol, perfluoroalkyl bromide , perfluoroalkyl iodide, perfluoropolyether (Krytox (trade name), Demnum (trade name), Fomblin (trade name), etc.), 1,3-bistrifluoromethylbenzene, methacrylic acid 2-(perfluoro alkyl)ethyls, 2-(perfluoroalkyl)ethyl acrylates, perfluoroalkylethylenes, freon 134a, and hexafluoropropene oligomers.

Examples of the fluorine-free organic solvent include acetone, methyl isobutyl ketone, cyclohexanone, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monobutyl ether, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, and propylene glycol. monobutyl ether acetate, dipropylene glycol dimethyl ether pentane, hexane, heptane, octane, dichloromethane, chloroform, carbon tetrachloride, dichloroethane, carbon disulfide, benzene, toluene, xylene, nitrobenzene, diethyl ether, dimethoxyethane, diglyme, triglyme, ethyl acetate , butyl acetate, dimethylformamide, dimethylsulfoxide, 2-butanone, acetonitrile, benzonitrile, butanol, 1-propanol, 2-propanol, ethanol, methanol, and diacetone alcohol.

Among them, the solvent is preferably methyl isobutyl ketone, propylene glycol monomethyl ether, hexadecane, butyl acetate, acetone, 2-butanone, cyclohexanone, ethyl acetate, diacetone alcohol or 2-propanol.

One of the above solvents may be used alone, or two or more thereof may be used in combination.

The above solvent is preferably used in the composition (a) in an amount of 30 to 95% by mass. More preferably, it is 50 to 90% by mass.

For example, an antifouling layer can be formed by applying the composition (a) to a substrate. It is also possible to form an antifouling layer by polymerizing after coating. Examples of the base material include resins (especially non-fluororesins).

The compounds of the present disclosure can be used with curable resins or curable monomers. A composition characterized by containing the above compound and a curable resin or a curable monomer is also one aspect of the present invention (herein sometimes referred to as composition (b)). Since the composition (b) has the above structure, it is possible to obtain a coating film which is resistant to fingerprints and which can be completely wiped off even if fingerprints are attached.

The curable resin may be either a photocurable resin or a thermosetting resin, and is not particularly limited as long as it has heat resistance and strength, but is preferably a photocurable resin, and an ultraviolet curable resin. more preferred.

Examples of the curable resin include epoxy-based polymer, acrylic-based polymer, polycarbonate-based polymer, polyester-based polymer, polyamide-based polymer, polyimide-based polymer, polyethersulfone-based polymer, cyclic polyolefin-based polymer, fluorine-containing polyolefin-based polymer ( PTFE, etc.), fluorine-containing cyclic amorphous polymers (Cytop (registered trademark), Teflon (registered trademark) AF, etc.).

Specific examples of the curable resin or monomers constituting the curable resin include alkyl vinyl ethers such as cyclohexylmethyl vinyl ether, isobutyl vinyl ether, cyclohexyl vinyl ether, ethyl vinyl ether; glycidyl vinyl ether, vinyl acetate, vinyl pivalate; Acrylates: phenoxyethyl acrylate, benzyl acrylate, stearyl acrylate, lauryl acrylate, 2-ethylhexyl acrylate, allyl acrylate, 1,3-butanediol diacrylate, 1,4-butanediol diacrylate, 1,6-hexanediol diacrylate , trimethylol, propane triacrylate, pentaerythritol triacrylate, dipentaerythritol hexaacrylate, ethoxyethyl acrylate, methoxyethyl acrylate, glycidyl acrylate, tetrahydrofurfuryl acrylate, diethylene glycol diacrylate, neopentyl glycol diacrylate, polyoxyethylene glycol Diacrylate, tripropylene glycol diacrylate, 2-hydroxyethyl acrylate, 2-hydroxypropyl acrylate, 4-hydroxybutyl vinyl ether, N,N-diethylaminoethyl acrylate, N,N-dimethylaminoethyl acrylate; N-vinylpyrrolidone, dimethyl Aminoethyl methacrylate Silicon-based acrylate, maleic anhydride, vinylene carbonate, chain side chain polyacrylate, cyclic side chain polyacrylate polynorbornene, polynorbornadiene, polycarbonate, polysulfonic acid amide; bisphenol A diglycidyl ether, bisphenol F diglycidyl ether , bisphenol S diglycidyl ether, 3,4-epoxycyclohexylmethyl-3,4-epoxycyclohexane carboxylate (Celoxide 2021P (registered trademark)), 1,2-hexahydrophthalic acid diglycidyl ester, 4-vinyl-1 -epoxy monomers such as cyclohexanediepoxide, 1,4-cyclohexanedimethanol diglycidyl ether, 4-tert-butylphenyl glycidyl ether, m,p-cresyl glycidyl ether, phenyl glycidyl ether, cresyl glycidyl ether; Cyclic amorphous polymers (Cytop (registered trademark), Teflon (registered trademark) AF, etc.) and the like can be mentioned.

The curable monomer may be either a photocurable monomer or a thermosetting monomer, but an ultraviolet curable monomer is preferred.

Examples of the curable monomer include (a) urethane (meth)acrylate, (b) epoxy (meth)acrylate, (c) polyester (meth)acrylate, (d) polyether (meth)acrylate, (e) silicone (meth)acrylates, (f) (meth)acrylate monomers, and the like.

Specific examples of the curable monomer include the following.
(a) Urethane (meth)acrylates include poly[(meth)acryloyloxyalkyl]isocyanurates typified by tris(2-hydroxyethyl)isocyanurate diacrylate and tris(2-hydroxyethyl)isocyanurate triacrylate. mentioned.
(b) Epoxy (meth)acrylate is obtained by adding a (meth)acryloyl group to an epoxy group, and bisphenol A, bisphenol F, phenol novolak, and alicyclic compounds are generally used as starting materials.
(c) Polyhydric alcohols constituting the polyester portion of polyester (meth)acrylate include ethylene glycol, 1,4-butanediol, 1,6-hexanediol, diethylene glycol, trimethylolpropane, dipropylene glycol, polyethylene glycol, Polypropylene glycol, pentaerythritol, dipentaerythritol, etc., and polybasic acids include phthalic acid, adipic acid, maleic acid, trimellitic acid, itaconic acid, succinic acid, terephthalic acid, alkenylsuccinic acid, and the like.
(d) Polyether (meth)acrylates include polyethylene glycol di(meth)acrylate, polypropylene glycol di(meth)acrylate, polyethylene glycol-polypropylene glycol di(meth)acrylate and the like.
(e) Silicon (meth)acrylate is a dimethylpolysiloxane with a molecular weight of 1,000 to 10,000 modified with (meth)acryloyl groups at one or both ends. exemplified.

(f) (meth)acrylate monomers include methyl (meth)acrylate, ethyl (meth)acrylate, n-propyl (meth)acrylate, isopropyl (meth)acrylate, n-butyl (meth)acrylate, isobutyl (meth)acrylate , sec-butyl (meth)acrylate, t-butyl (meth)acrylate, n-pentyl (meth)acrylate, 3-methylbutyl (meth)acrylate, n-hexyl (meth)acrylate, 2-ethyl-n-hexyl (meth)acrylate ) acrylate, n-octyl (meth) acrylate, cyclohexyl (meth) acrylate, isobornyl (meth) acrylate, benzyl (meth) acrylate, 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 3-hydroxy Propyl (meth)acrylate, 4-hydroxybutyl (meth)acrylate, 5-hydroxypentyl (meth)acrylate, 6-hydroxyhexyl (meth)acrylate, 4-hydroxycyclohexyl (meth)acrylate, neopentyl glycol mono (meth)acrylate , 3-chloro-2-hydroxypropyl (meth)acrylate, (1,1-dimethyl-3-oxobutyl) (meth)acrylate, 2-acetoacetoxyethyl (meth)acrylate, 2-methoxyethyl (meth)acrylate, 2-ethoxyethyl (meth) acrylate, neopentyl glycol mono (meth) acrylate, 3-chloro-2-hydroxypropyl (meth) acrylate, glycerin mono (meth) acrylate, ethylene glycol diacrylate, propylene glycol diacrylate, 1, Examples include 6-hexanediol diacrylate, 1,9-nonanediol diacrylate, 1,10-decanediol diacrylate, trimethylolpropane triacrylate, and pentaerythritol tetraacrylate.

Among the above curable resins and curable monomers, commercially available and preferred ones are listed below.

Examples of the curable resin include silicone resins PAK-01 and PAK-02 (manufactured by Toyo Gosei Chemical Co., Ltd.), nanoimprint resin NIF series (manufactured by Asahi Glass Co., Ltd.), nanoimprint resin OCNL series (manufactured by Tokyo Ohka Kogyo Co., Ltd.), NIAC2310 (Daicel Kagaku Kogyo Co., Ltd.), epoxy acrylate resins EH-1001, ES-4004, EX-C101, EX-C106, EX-C300, EX-C501, EX-0202, EX-0205, EX-5000, etc. (Kyoeisha Chemical Co., Ltd. (manufactured by Sumitomo Bayern Urethane), hexamethylene diisocyanate-based polyisocyanates, Sumidule N-75, Sumidule N3200, Sumidule HT, Sumidule N3300, and Sumidule N3500 (manufactured by Sumitomo Bayern Urethane).

Examples of the curable monomer include silicone acrylate-based resins, polyfunctional acrylates, polyfunctional methacrylates, and alkoxysilane group-containing (meth)acrylates.

Silicone acrylate resins include Silaplane FM-0611, Silaplane FM-0621, Silaplane FM-0625, double-ended (meth)acrylic Silaplane FM-7711, Silaplane FM-7721 and Silaplane FM -7725, etc., Silaplane FM-0411, Silaplane FM-0421, Silaplane FM-0428, Silaplane FM-DA11, Silaplane FM-DA21, Silaplane-DA25, single-ended (meth)acrylic Silaplane Examples include FM-0711, Silaplane FM-0721, Silaplane FM-0725, Silaplane TM-0701 and Silaplane TM-0701T (manufactured by JCN).

Polyfunctional acrylates include A-9300, A-9300-1CL, A-GLY-9E, A-GLY-20E, A-TMM-3, A-TMM-3L, A-TMM-3LM-N, A -TMPT, A-TMMT (manufactured by Shin-Nakamura Kogyo Co., Ltd.) and the like.

Examples of polyfunctional methacrylates include TMPT (manufactured by Shin-Nakamura Kogyo Co., Ltd.).

Alkoxysilane group-containing (meth)acrylates include 3-(meth)acryloyloxypropyltrichlorosilane, 3-(meth)acryloyloxypropyltrimethoxysilane, 3-(meth)acryloyloxypropyltriethoxysilane, 3-( meth)acryloyloxypropyltriisopropoxysilane (also known as (triisopropoxysilyl)propyl methacrylate (abbreviation: TISMA) and triisopropoxysilyl)propyl acrylate), 3-(meth)acryloxyisobutyltrichlorosilane, 3-(meth) acryloxyisobutyltriethoxysilane, 3-(meth)acryloxyisobutyltriisopropoxy, 3-(meth)acryloxyisobutyltrimethoxysilane, and the like.

Composition (b) also preferably comprises a cross-linking catalyst. Examples of the cross-linking catalyst include radical polymerization initiators and acid generators.

The radical polymerization initiator is a compound that generates radicals by heat or light, and examples thereof include radical thermal polymerization initiators and radical photopolymerization initiators. In the present invention, the above radical photopolymerization initiator is preferred.

Examples of the radical thermal polymerization initiator include diacyl peroxides such as benzoyl peroxide and lauroyl peroxide, dialkyl peroxides such as dicumyl peroxide and di-t-butyl peroxide, diisopropyl peroxydicarbonate, Peroxycarbonates such as bis (4-t-butylcyclohexyl) peroxydicarbonate, t-butyl peroxyoctoate, peroxide compounds such as alkyl peresters such as t-butyl peroxybenzoate, and azobis iso Radical-generating azo compounds such as butyronitrile and the like are included.

Examples of the radical photopolymerization initiator include -diketones such as benzyl and diacetyl, acyloins such as benzoin, acyloin ethers such as benzoin methyl ether, benzoin ethyl ether, and benzoin isopropyl ether, thioxanthone, 2,4- Thioxanthones such as diethylthioxanthone and thioxanthone-4-sulfonic acid, benzophenones such as benzophenone, 4,4′-bis(dimethylamino)benzophenone, 4,4′-bis(diethylamino)benzophenone, acetophenone, 2-(4- Toluenesulfonyloxy)-2-phenylacetophenone, p-dimethylaminoacetophenone, 2,2′-dimethoxy-2-phenylacetophenone, p-methoxyacetophenone, 2-methyl[4-(methylthio)phenyl]-2-morpholino-1 -propanone, acetophenones such as 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)-butan-1-one, anthraquinone, quinones such as 1,4-naphthoquinone, 2-dimethylaminobenzoic acid aminobenzoic acids such as ethyl, ethyl 4-dimethylaminobenzoate, (n-butoxy)ethyl 4-dimethylaminobenzoate, isoamyl 4-dimethylaminobenzoate, 2-ethylhexyl 4-dimethylaminobenzoate, phenacyl chloride, Examples thereof include halogen compounds such as trihalomethylphenylsulfone, acylphosphine oxides, and peroxides such as di-t-butyl peroxide.

Commercially available products of the radical photopolymerization initiator are exemplified below.
IRGACURE 651: 2,2-dimethoxy-1,2-diphenylethan-1-one,
IRGACURE 184: 1-hydroxy-cyclohexyl-phenyl-ketone,
IRGACURE 2959: 1-[4-(2-hydroxyethoxy)-phenyl]-2-hydroxy-2-methyl-1-propan-1-one,
IRGACURE 127: 2-hydroxy-1-{4-[4-(2-hydroxy-2-methyl-propionyl)-benzyl]phenyl}-2-methyl-propan-1-one,
IRGACURE 907: 2-methyl-1-(4-methylthiophenyl)-2-morpholinopropan-1-one,
IRGACURE 369: 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)-butanone-1,
IRGACURE 379: 2-(dimethylamino)-2-[(4-methylphenyl)methyl]-1-[4-(4-morpholinyl)phenyl]-1-butanone,
IRGACURE 819: bis(2,4,6-trimethylbenzoyl)-phenylphosphine oxide,
IRGACURE 784: bis(η5-2,4-cyclopentadien-1-yl)-bis(2,6-difluoro-3-(1H-pyrrol-1-yl)-phenyl)titanium,
IRGACURE OXE 01: 1,2-octanedione, 1-[4-(phenylthio)-,2-(O-benzoyloxime)],
IRGACURE OXE 02: ethanone, 1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]-, 1-(0-acetyloxime),
IRGACURE261, IRGACURE369, IRGACURE500,
DAROCUR 1173: 2-hydroxy-2-methyl-1-phenyl-propan-1-one,
DAROCUR TPO: 2,4,6-trimethylbenzoyl-diphenyl-phosphine oxide,
DAROCUR1116, DAROCUR2959, DAROCUR1664, DAROCUR4043,
IRGACURE 754 oxyphenylacetic acid: a mixture of 2-[2-oxo-2-phenylacetoxyethoxy]ethyl ester and oxyphenylacetic acid, 2-(2-hydroxyethoxy)ethyl ester,
IRGACURE 500: a mixture of IRGACURE 184 and benzophenone (1
: 1),
IRGACURE 1300: a mixture of IRGACURE 369 and IRGACURE 651 (3:7);
IRGACURE 1800: a mixture of CGI403 and IRGACURE 184 (1:3),
IRGACURE 1870: a mixture of CGI403 and IRGACURE 184 (7:3);
DAROCUR 4265: a mixture of DAROCUR TPO and DAROCUR 1173 (1:1).
IRGACURE is manufactured by BASF, and DAROCUR is manufactured by Merck Japan.

Further, when a radical photopolymerization initiator is used as the crosslinking catalyst, diethylthioxanthone, isopropylthioxanthone, or the like can be used in combination as a sensitizer, and DAROCUR EDB (ethyl-4-dimethylaminobenzoate) can be used as a polymerization accelerator. ), DAROCUR EHA (2-ethylhexyl-4-dimethylaminobenzoate) and the like may be used in combination.

When the sensitizer is used, the amount of the sensitizer to be blended is preferably 0.1 to 5 parts by mass with respect to 100 parts by mass of the curable resin or curable monomer. More preferably, it is 0.1 to 2 parts by mass.

When the polymerization accelerator is used, the amount of the polymerization accelerator to be blended is preferably 0.1 to 5 parts by mass with respect to 100 parts by mass of the curable resin or curable monomer. More preferably, it is 0.1 to 2 parts by mass.

The acid generator is a material that generates acid by applying heat or light, and examples thereof include thermal acid generators and photoacid generators. In the present invention, photoacid generators are preferred.

Examples of the thermal acid generator include benzoin tosylate, nitrobenzyl tosylate (especially 4-nitrobenzyl tosylate), and other alkyl esters of organic sulfonic acids.

The photoacid generator is composed of a chromophore that absorbs light and an acid precursor that becomes an acid after decomposition. The acid generator is excited to generate acid from the acid precursor portion.

Examples of the photoacid generator include diazonium salts, phosphonium salts, sulfonium salts, iodonium salts, CF ₃ SO ₃ , p-CH ₃ PhSO ₃ , p-NO ₂ PhSO ₃ (where Ph is a phenyl group) and the like. Salts, organic halogen compounds, orthoquinone-diazide sulfonyl chlorides, sulfonate esters, and the like can be mentioned. In addition, as photoacid generators, 2-halomethyl-5-vinyl-1,3,4-oxadiazole compounds, 2-trihalomethyl-5-aryl-1,3,4-oxadiazole compounds, 2-trihalo Also included are methyl-5-hydroxyphenyl-1,3,4-oxadiazole compounds. The organic halogen compound is a compound that forms a hydrohalic acid (for example, hydrogen chloride).

Commercially available products of the photoacid generator are exemplified below.
Wako Pure Chemical Industries, Ltd. WPAG-145 [bis (cyclohexylsulfonyl) diazomethane], WPAG-170 [bis (t-butylsulfonyl) diazomethane], WPAG-199 [bis (p-toluenesulfonyl) diazomethane], WPAG-281 [triphenylsulfonium trifluoromethanesulfonate], WPAG-336 [diphenyl-4-methylphenylsulfonium trifluoromethanesulfonate], WPAG-367 [diphenyl-2,4,6-trimethylphenylsulfonium p-toluenesulfonate], Ciba Specialty Chemicals IRGACURE PAG103 [(5-propylsulfonyloximino-5H-thiophen-2-ylidene) -(2-methylphenyl) acetonitrile], IRGACURE PAG108 [(5-octylsulfonyloximino-5H-thiophene-2- ylidene)-(2-methylphenyl)acetonitrile)], IRGACURE PAG121 [5-p-toluenesulfonyloximino-5H-thiophen-2-ylidene-(2-methylphenyl)acetonitrile], IRGACURE PAG203, CGI725, Sanwa Chemical TFE-triazine [2-[2-(furan-2-yl)ethenyl]-4,6-bis(trichloromethyl)-s-triazine], TME-triazine [2-[2-(5-methyl furan-2-yl)ethenyl]-4,6-bis(tri-chloromethyl)-s-triazine]MP-triazine[2-(methoxyphenyl)-4,6-bis(trichloromethyl)-s-triazine] , dimethoxy[2-[2-(3,4-dimethoxyphenyl)ethenyl]-4,6-bis(tri-chloromethyl)-s-triazine].

The amount of the cross-linking catalyst compounded is preferably 0.1 to 10 parts by mass with respect to 100 parts by mass of the curable resin or the curable monomer. Within such a range, a sufficient cured product can be obtained. The blending amount of the crosslinking catalyst is more preferably 0.3 to 5 parts by mass, and still more preferably 0.5 to 2 parts by mass.

When the acid generator is used as the cross-linking catalyst, an acid scavenger may be added as necessary to control the diffusion of the acid generated from the acid generator.

Although the acid scavenger is not particularly limited, basic compounds such as amines (especially organic amines), basic ammonium salts, and basic sulfonium salts are preferred. Among these acid scavengers, organic amines are more preferable from the viewpoint of excellent image performance.

Specific examples of the acid scavenger include 1,5-diazabicyclo[4.3.0]-5-nonene, 1,8-diazabicyclo[5.4.0]-7-undecene, 1,4- diazabicyclo[2.2.2]octane, 4-dimethylaminopyridine, 1-naphthylamine, piperidine, hexamethylenetetramine, imidazoles, hydroxypyridines, pyridines, 4,4'-diaminodiphenyl ether, pyridinium p-toluenesulfonate , 2,4,6-trimethylpyridinium p-toluenesulfonate, tetramethylammonium p-toluenesulfonate, and tetrabutylammonium lactate, triethylamine, tributylamine and the like. Among these, 1,5-diazabicyclo[4.3.0]-5-nonene, 1,8-diazabicyclo[5.4.0]-7-undecene, 1,4-diazabicyclo[2.2.2] Organic amines such as octane, 4-dimethylaminopyridine, 1-naphthylamine, piperidine, hexamethylenetetramine, imidazoles, hydroxypyridines, pyridines, 4,4'-diaminodiphenyl ether, triethylamine and tributylamine are preferred.

The amount of the acid scavenger compounded is preferably 20 parts by mass or less, more preferably 0.1 to 10 parts by mass, and still more preferably 0.5 to 10 parts by mass with respect to 100 parts by mass of the acid generator. 5 parts by mass.

Composition (b) may contain a solvent. Examples of the solvent include water-soluble organic solvents, organic solvents (especially oil-soluble organic solvents), water, and the like.

Examples of the water-soluble organic solvent include acetone, methyl ethyl ketone, methyl amyl ketone, ethyl acetate, propylene glycol, propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate (PGMEA), dipropylene glycol, dipropylene glycol monomethyl ether, dipropylene Glycol dimethyl ether, dipropylene glycol monomethyl ether acetate, dipropylene glycol diacetate, tripropylene glycol, 3-methoxybutyl acetate (MBA), 1,3-butylene glycol diacetate, cyclohexanol acetate, dimethylformamide, dimethyl sulfoxide, methyl cellosolve , cellosolve acetate, butyl cellosolve, butyl carbitol, carbitol acetate, ethyl lactate, isopropyl alcohol, methanol, ethanol and the like.

Examples of the organic solvent include chloroform, HFC141b, HCHC225, hydrofluoroether, pentane, hexane, heptane, octane, cyclohexane, benzene, toluene, xylene, petroleum ether, tetrahydrofuran, 1,4-dioxane, methyl isobutyl ketone, and acetic acid. butyl, 1,1,2,2-tetrachloroethane, 1,1,1-trichloroethane, trichlorethylene, perchlorethylene, tetrachlorodifluoroethane, trichlorotrifluoroethane and the like. These solvents may be used alone or in combination of two or more.

As the solvent, PGMEA and MBA are particularly preferred from the viewpoint of the solubility and safety of the components contained in the resist composition.

The above solvent is preferably used in the composition (b) in an amount of 10 to 95% by mass. More preferably, it is 20 to 90% by mass.

For example, a resist film can be formed by applying the composition (b) to a substrate. Examples of materials for the base material include synthetic resins.

Examples of the synthetic resin include cellulose resins such as triacetyl cellulose (TAC), polyolefins such as polyethylene, polypropylene, ethylene-propylene copolymer, and ethylene-vinyl acetate copolymer (EVA), cyclic polyolefins, modified Polyolefin, polyvinyl chloride, polyvinylidene chloride, polystyrene, polyamide, polyimide, polyamideimide, polycarbonate, poly-(4-methylpentene-1), ionomer, acrylic resin, polymethyl methacrylate, acrylic-styrene copolymer (AS resin), butadiene-styrene copolymer, ethylene-vinyl alcohol copolymer (EVOH), polyester such as polyethylene terephthalate (PET), polybutylene terephthalate (PBT), polycyclohexane terephthalate (PCT), polyether, polyether ketone (PEK), polyetheretherketone (PEEK), polyetherimide, polyacetal (POM), polyphenylene oxide, modified polyphenylene oxide, polyarylate, aromatic polyester (liquid crystal polymer), polytetrafluoroethylene, polyvinylidene fluoride, other fluorine Various thermoplastic elastomers such as styrene-based, polyolefin-based, polyvinyl chloride-based, polyurethane-based, fluororubber-based, and chlorinated polyethylene-based resins, epoxy resins, phenolic resins, urea resins, melamine resins, unsaturated polyesters, silicone resins , polyurethane, etc., or copolymers, blends, polymer alloys, etc. mainly composed of these. can.

The above resist film can be used for nanoimprinting. For example, a step of pressing a mold having a fine pattern formed on its surface against the resist film to transfer the fine pattern, a step of curing the resist film on which the transfer pattern is formed, and obtaining a cured resist having the transfer pattern; And, a pattern-transferred cured resist can be obtained by a production method including the step of releasing the cured resist from the mold.

The compounds of this disclosure can be used with solvents. A composition characterized by containing the above compound and a solvent is also one aspect of the present invention (sometimes referred to herein as composition (c)).

In the composition (c), the concentration of the compound is preferably 0.001 to 5.0% by mass, more preferably 0.005 to 1.0% by mass, and further 0.01 to 0.5% by mass. preferable.

As the solvent, a fluorine-based solvent is preferable. Examples of the fluorine-based inert solvent include perfluorohexane, perfluoromethylcyclohexane, perfluoro-1,3-dimethylcyclohexane, and dichloropentafluoropropane (HCFC-225).

Composition (c) also preferably contains a fluorine-containing oil. As the fluorine-containing oil,
Formula: R ¹¹¹ -(R ¹¹² O) _m -R ¹¹³
(R ¹¹¹ and R ¹¹³ are independently F, an alkyl group having 1 to 16 carbon atoms, a fluorinated alkyl group having 1 to 16 carbon atoms, —R ¹¹⁴ —X ¹¹¹ (R ¹¹⁴ is a single bond or X ¹¹¹ is -NH ₂ , -OH, -COOH, -CH=CH ₂ , -OCH ₂ CH=CH ₂ , halogen, phosphoric acid, phosphoric acid ester, carboxylic acid ester, thiol, thioether, alkyl Ether (which may be substituted with fluorine), aryl, aryl ether, amide), R ¹¹² is a fluorinated alkylene group having 1 to 4 carbon atoms, and m is an integer of 2 or more) are more preferred.

R ¹¹¹ and R ¹¹³ are independently F, an alkyl group having 1 to 3 carbon atoms, a fluorinated alkyl group having 1 to 3 carbon atoms, or R ¹¹⁴ -X ¹¹¹ (R ¹¹⁴ and X ¹¹¹ are as described above). Preferably, F, a fully fluorinated alkyl group having 1 to 3 carbon atoms or R ¹¹⁴ -X ¹¹¹ (R ¹¹⁴ is a single bond or an alkylene group having 1 to 3 carbon atoms, X ¹¹¹ is —OH or OCH ₂ CH═CH ₂ ) is more preferred.

As m, an integer of 300 or less is preferable, and an integer of 100 or less is more preferable.

R ¹¹² is preferably a fully fluorinated alkylene group having 1 to 4 carbon atoms. —R ¹¹² O— is, for example,
Formula: -(CX ¹¹² ₂ CF ₂ CF ₂ O) _n111 (CF(CF ₃ )CF ₂ O) _n112 (CF ₂ CF ₂ O) _n113 (CF ₂ O) _n114 (C ₄ F ₈ O) _n115 -
(n111, n112, n113, n114 and n115 are independently integers of 0 or 1 or more, X ¹¹² is H, F or Cl, the order of existence of each repeating unit is arbitrary),
Formula: -(OC ₂ F ₄ -R ¹¹⁸ ) _f -
(R ¹¹⁸ is a group selected from OC ₂ F ₄ , OC ₃ F ₆ and OC ₄ F ₈ , f is an integer of 2 to 100).

Each of n111 to n115 is preferably an integer of 0 to 200. The sum of n111 to n115 is preferably 1 or more, more preferably 5 to 300, even more preferably 10 to 200, and particularly preferably 10 to 100.

R ¹¹⁸ is a group selected from OC ₂ F ₄ , OC ₃ F ₆ and OC ₄ F ₈ or a combination of two or three groups independently selected from these groups. The combination of two or three groups independently selected from OC ₂ F ₄ , OC ₃ F ₆ and OC ₄ F ₈ is not particularly limited, but for example -OC ₂ F ₄ OC ₃ F ₆ -, -OC _{2F4OC4F8- , -OC3F6OC2F4- , -OC3F6OC3F6- , -OC3F6OC4F8- , -OC4F8OC4F _ _ _ _ _ _ _ _ _ _ 8- , -OC4F8OC3F6- , -OC4F8OC2F4- , -OC2F4OC2F4OC3F6- , -OC2F4OC2F4OC _ _ _ _ _ _ _ _ _ _ 4F8- , -OC2F4OC3F6OC2F4- , -OC2F4OC3F6OC3F6- , -OC2F4OC4F8OC2F4- , _ _ _ _ _ _ _ _ _ _ _ _ -OC3F6OC2F4OC2F4- , -OC3F6OC2F4OC3F6- , -OC3F6OC3F6OC2F4- , and OC4F8 _ _ _ _ _ _ _ _ _ _ _ _} OC ₂ F ₄ OC ₂ F ₄ - and the like. f is an integer of 2-100, preferably an integer of 2-50. In the above formula, OC ₂ F ₄ , OC ₃ F ₆ and OC ₄ F ₈ may be linear or branched, preferably linear. In this aspect, the formula -(OC ₂ F ₄ -R ¹¹⁸ ) _f - is preferably the formula -(OC ₂ F ₄ -OC ₃ F ₆ ) _f - or the formula -(OC ₂ F ₄ -OC ₄ F ₈ ) _f −.

The fluoropolyether preferably has a weight average molecular weight of 500 to 100,000, more preferably 50,000 or less, still more preferably 10,000 or less, and particularly preferably 6,000 or less. The weight average molecular weight can be measured by gel permeation chromatography (GPC).

Commercially available fluoropolyethers include Demnum (manufactured by Daikin Industries, Ltd.), Fomblin (manufactured by Solvay Specialty Polymers Japan), Barrierta (manufactured by NOK Klüber), Krytox (manufactured by DuPont), and the like. mentioned.

The fluorine-containing oil is, for example, 50% by mass or less, preferably 30% by mass or less, relative to the compounds represented by formulas (1) and (2) of the present disclosure (the total when two or more are used). obtain. In one aspect, the fluorine-containing oil is, for example, 0.1% by mass or more, preferably may be included in an amount of 1% by weight or more, for example 5% by weight or more.

Composition (c) can be used to form a release layer on a substrate. The release layer can be formed by a method of immersing the substrate in the composition (c), a method of exposing the substrate to the vapor of the composition (c) for vapor deposition, or printing the composition (c) on the substrate. and a method of applying the composition (c) to the base material using an inkjet method. After the immersion, vapor deposition, printing, and application, drying may be performed. A mold having an uneven pattern formed thereon can be used as the substrate, and the mold having a release layer formed thereon can be used for nanoimprinting.

Examples of the base material include resins such as polymer resins such as silicone.

The present disclosure also provides an antifouling agent characterized by comprising a compound as described above or a composition as described above.

The antifouling agent can be used by applying it to a resin (especially non-fluororesin).

The above-mentioned antifouling agent can be used in a variety of articles (especially optical materials) that require surface antifouling properties and swelling properties. Examples of articles include front protective plates for displays such as PDP and LCD, antireflection plates, polarizing plates, and anti-glare plates; cover windows for foldable displays, rollable displays and bending displays; devices such as mobile phones and personal digital assistants; Touch panel sheet; DVD disc, CD-R, optical disc such as MO; Spectacle lens; Optical fiber; board and its lower part, panels around the driver's seat, switches, levers, etc., inside the trunk), etc.

Optical materials such as optical discs contain a carbon-carbon double bond-containing composition, a polymer comprising a carbon-carbon double bond-containing composition, a carbon-carbon double bond-containing composition and a carbon-carbon double bond. It is preferable that the surface is coated with a film formed by adding perfluoropolyether (PFPE) to the polymerized product of the contained monomer so that the content is 0.01% by weight to 10% by weight. At 0.01% by weight to 10% by weight, the characteristic physical properties of PFPE addition (antifouling, etc.) appear, the surface hardness is high, and the transmittance is high.

The present disclosure is also a release agent characterized by comprising a compound of the present disclosure or a composition of the present disclosure.

A release layer can be formed on the substrate from the release agent. The release layer can be formed by a method of immersing the base material in the release agent, a method of exposing the base material to the vapor of the release agent for vapor deposition, a method of printing the composition on the base material, or an inkjet method. and a method of applying the composition to the base material using the above method. After the immersion, vapor deposition, printing, and application, drying may be performed. A mold having an uneven pattern formed thereon can be used as the substrate, and the mold having a release layer formed thereon can be used for nanoimprinting.

Examples of the substrate include metals, metal oxides, quartz, polymeric resins such as silicone, semiconductors, insulators, and composites thereof.

The thickness of the surface treatment layer is not particularly limited. In the case of optical members, the thickness of the surface treatment layer is in the range of 0.05 to 60 μm, preferably 0.1 to 30 μm, more preferably 0.5 to 20 μm. It is preferable in terms of durability and antifouling properties.

As described above, the compositions (a) to (c) of the present disclosure are used as so-called surface treatment agents.

The article obtained using the surface treatment agent of the present disclosure has been described in detail above. The application, method of use, method of manufacturing an article, etc. of the surface treatment agent of the present disclosure are not limited to those exemplified above.

Hereinafter, the present disclosure will be described in Examples, but the present disclosure is not limited to the following Examples. In the present examples, the chemical formulas of the polymers shown below all show the average composition, and the repeating units ((CF ₂ CF ₂ CF ₂ O), (CF ₂ CF ₂ O), ( The order of existence of CF ₂ O)) is arbitrary.

Synthesis Example 1: Production of PFPE-containing compound (A) Using CF ₃ CF ₂ CF ₂ O—(CF ₂ CF ₂ CF ₂ O) ₂₅ —CF ₂ CF ₂ CH ₂ OH as a starting material, the method described in WO2018/056413A1 The following perfluoropolyether (PFPE)-containing compound (A) was synthesized according to.

PFPE-containing compound (A):

Synthesis Example 2: Production of PFPE-Containing Compound (B) 10.2 g of PFPE-containing compound (A) was dissolved in 20 g of m-hexafluoroxylene, 1.16 g of tetramethyldisiloxane was added, and the mixture was stirred at 25° C. for 30 minutes. Subsequently, 0.10 ml of a xylene solution containing 2% Pt complex of 1,3-divinyl-1,1,3,3-tetramethyldisiloxane was added, followed by heating and stirring at 60° C. for 5 hours. After that, activated carbon treatment was performed, and 10.1 g of the following PFPE-containing compound (B) was obtained by distilling off low-boiling volatile matter under reduced pressure.

PFPE-containing compound (B):

Synthesis Example 3: Production of PFPE-containing compound (C) 10.0 g of the PFPE-containing compound (B) obtained above was dissolved in 25 g of m-hexafluoroxylene, and 0.96 g of allyl glycidyl ether was added. Stir for a minute. Subsequently, 0.10 ml of a xylene solution containing 2% Pt complex of 1,3-divinyl-1,1,3,3-tetramethyldisiloxane was added, and the mixture was heated and stirred at 70° C. for 5 hours. After that, the following PFPE-containing compound (C) 9.4 g was obtained by performing an activated carbon treatment and distilling off the low boiling point volatile matter under reduced pressure. A 20 wt % solution was prepared using a mixed solvent of heptafluorocyclopentane and 2-butanone.

PFPE-containing compound (C):

Synthesis Example 4: Production of PFPE-containing compound (D) PFPE-containing compound (D) 9 was prepared in the same manner as in Synthesis Example 3 except that 0.63 g of 1,2-epoxy-5-hexene was charged instead of allyl glycidyl ether. After obtaining .1 g, a 20 wt % solution was prepared using a mixed solvent of 1,1,2,2,3,3,4-heptafluorocyclopentane and 2-butanone.

PFPE-containing compound (D):

Synthesis Example 5: Production of PFPE-containing compound (E) PFPE-containing compound (E) was prepared in the same manner as in Synthesis Example 3 except that 0.80 g of 1,2-epoxy-4-vinylcyclohexane was charged instead of allyl glycidyl ether. After obtaining 9.5 g, a 20 wt % solution was prepared using a mixed solvent of 1,1,2,2,3,3,4-heptafluorocyclopentane and 2-butanone.

PFPE-containing compound (E):

Synthesis Example 6: Production of PFPE-containing compound (F) 10.0 g of PFPE-containing compound (A) was dissolved in 20 g of m-hexafluoroxylene, 4.39 g of tetramethylcyclotetrasiloxane was added, and the mixture was stirred at 45°C for 30 minutes. . Subsequently, 0.14 ml of a xylene solution containing 2% Pt complex of 1,3-divinyl-1,1,3,3-tetramethyldisiloxane was added, followed by heating and stirring at 75° C. for 5 hours. Thereafter, activated carbon treatment was performed, and the solvent and excess tetramethylcyclotetrasiloxane were distilled off under reduced pressure to obtain 10.3 g of the following PFPE-containing compound (F).

PFPE-containing compound (F):

Synthesis Example 7: Production of PFPE-Containing Compound (G) 10.0 g of PFPE-containing compound (F) was dissolved in 20 g of m-hexafluoroxylene, 2.67 g of allyl glycidyl ether was added, and the mixture was stirred at 45° C. for 30 minutes. Subsequently, 0.18 ml of a xylene solution containing 2% Pt complex of 1,3-divinyl-1,1,3,3-tetramethyldisiloxane was added, and the mixture was heated and stirred at 80° C. for 5 hours. Thereafter, activated carbon treatment was performed, and the solvent and excess allyl glycidyl ether were distilled off under reduced pressure. After obtaining 10.1 g of the following PFPE-containing compound (G), a 20 wt % solution was prepared using a mixed solvent of 1,1,2,2,3,3,4-heptafluorocyclopentane and 2-butanone.

PFPE-containing compound (G):

Synthesis Example 8: Production of PFPE-Containing Compound (H) CF ₃ O—(CF ₂ CF ₂ O) _m (CF ₂ O) _n —CF ₂ CH ₂ OH (m=24, n=22) as a starting material, The following perfluoropolyether (PFPE)-containing compound (H) was synthesized according to the method described in WO2018/056413A1.

PFPE-containing compound (H):

Synthesis Example 9: Production of PFPE-containing compound (I) A PFPE-containing compound ( I) 10.2 g was obtained.

PFPE-containing compound (I):

Synthesis Example 10: Production of PFPE-containing compound (J) A PFPE-containing compound (J ), a 20 wt % solution was prepared using a mixed solvent of 1,1,2,2,3,3,4-heptafluorocyclopentane and 2-butanone.

PFPE-containing compound (J):

Synthesis Example 11: Preparation of PFPE-containing compound (K) Using HOCH ₂ CF ₂ CF ₂ O—(CF ₂ CF ₂ CF ₂ O) ₂₅ —CF ₂ CF ₂ CH ₂ OH as a starting material, the method described in WO2018/056413A1 The following perfluoropolyether (PFPE)-containing compound (K) was synthesized according to.

PFPE-containing compound (K):

Synthesis Example 12: Production of PFPE-Containing Compound (L) 9.0 g of PFPE-containing compound (K) was dissolved in 18 g of m-hexafluoroxylene, 1.69 g of tetramethyldisiloxane was added, and the mixture was stirred at 25° C. for 30 minutes. Subsequently, 0.16 ml of a xylene solution containing 2% Pt complex of 1,3-divinyl-1,1,3,3-tetramethyldisiloxane was added, followed by heating and stirring at 70° C. for 5 hours. After that, activated carbon treatment was performed, and 9.1 g of the following PFPE-containing compound (L) was obtained by distilling off low-boiling volatiles under reduced pressure.

PFPE-containing compound (L):

Synthesis Example 13: Production of PFPE-containing compound (M) 9.0 g of the PFPE-containing compound (L) obtained above was dissolved in 18 g of m-hexafluoroxylene, 2.52 g of allyl glycidyl ether was charged, and the mixture was stirred at 25°C for 30 minutes. Stir for a minute. Subsequently, 0.20 ml of a xylene solution containing 2% Pt complex of 1,3-divinyl-1,1,3,3-tetramethyldisiloxane was added, followed by heating and stirring at 75° C. for 5 hours. After that, the following PFPE-containing compound (M) 9.0 g was obtained by performing an activated carbon treatment and distilling off the low boiling point volatile matter under reduced pressure. A 20 wt % solution was prepared using a mixed solvent of heptafluorocyclopentane and 2-butanone.

PFPE-containing compound (M):

Comparative Compound Synthesis Example 1
Preparation of PFPE-containing compound (N) Using CF ₃ CF ₂ CF ₂ O—(CF ₂ CF ₂ CF ₂ O) ₁₁ —CF ₂ CF ₂ CH ₂ OH as a starting material, according to the method described in WO2018/056413A1, The following perfluoropolyether (PFPE)-containing compound (N) was synthesized.

PFPE-containing compound (N):

Comparative Compound Synthesis Example 2
Preparation of PFPE-Containing Compound (O) Starting from HOCH ₂ CF ₂ O—(CF ₂ CF ₂ O) _m (CF ₂ O) _n —CF ₂ CH ₂ OH (m=24, n=22), According to the method described in No. 5939712, the following perfluoropolyether (PFPE)-containing compound (O) was synthesized.

PFPE-containing compound (O):

<Evaluation>
(Compatibility test with acetone)
The PFPE-containing compounds (C), (D), (E), (G), (J), and (M) obtained above, and the PFPE-containing compounds (N) and (O) each had a solid concentration of 4. The mixture was mixed with acetone so as to have a concentration of 0 wt %, stirred with a mix rotor for 2 hours, and the state of the mixture was visually confirmed. The evaluation criteria were as follows. The results are shown in Table 1 below.
O: Dissolved transparently and uniformly.
x: Turbidity was observed.

(Creation of coating agent)
Film formation conditions (1) :
Celoxide 2021P (3,4-epoxycyclohexylmethyl-3,4-epoxycyclohexane carboxylate, manufactured by Daicel) was dissolved in 2-butanone, and the solution was added with PFPE-containing compounds (C), (D), and (E). ), (G), (J), (M), and PFPE-containing compounds (N), (O) were added so that the solid concentration was 1.0% with respect to celoxide 2021P, and further light was added. CPI-200K (manufactured by San-Apro Co., Ltd.), which is an acid generator, was similarly added at 2.0% in terms of solid concentration to obtain a coating agent containing 50% by mass of PFPE.
Celoxide 2021P:

Film formation conditions (2) :
Bisphenol A diglycidyl ether was dissolved in 2-butanone, and PFPE-containing compounds (C), (D), (E), (G), (J), (M), and PFPE-containing compound (N ) and (O) are added to the bisphenol A diglycidyl ether so that the solid concentration is 1.0%, and a photoacid generator CPI-200K (manufactured by San-Apro Co., Ltd.) is added. Similarly, 2.0% was added in terms of solid concentration to obtain a 50% by mass PFPE-containing coating agent.

(Creation of cured film and evaluation of properties)
The PFPE-containing coating agents obtained under the film forming conditions (1) and (2) were placed on a PET film (Cosmoshine A4160, manufactured by Toyobo Co., Ltd.), and a uniform coating film was formed using a bar coater. The resulting coating film was dried at 70° C. for 10 minutes and irradiated with light containing UV light of 365 nm in the air at an intensity of 600 mJ/cm ² to obtain a cured film (surface treatment layer). The initial characteristics of each cured film obtained were evaluated as follows.

(Appearance of cured film)
The appearance of the cured film was visually confirmed. Evaluation was based on the following criteria. Table 1 shows the results.
〇: Transparent ×: Whitening

<Evaluation of tactile sensation>
The tactile sensation of the fingertip was evaluated by pressing the index finger against the surface layer of the cured film and repeatedly reciprocating it left and right to rub it. Evaluation was based on the following criteria. Table 1 shows the results.
A: Extremely smooth feel.
O: Smooth feel.
x: When the fingertip is moved, it is caught and there is a sense of resistance.

<Evaluation of antifouling property>
(Static contact angle of water)
The static contact angle of water was measured by the following method using a fully automatic contact angle meter DropMaster 700 (manufactured by Kyowa Interface Science Co., Ltd.).

(Method for measuring static contact angle)
The static contact angle was obtained by dropping 3 μL of water from a microsyringe onto a substrate placed horizontally and taking a still image 1 second after dropping with a video microscope. The static contact angle of water was measured at five different points on the surface treatment layer of the base material, and the average value was calculated and used. Initial values were measured for the cured film of each PFPE-containing coating agent. Table 1 shows the results.

(fingerprint adhesion)
A finger was pressed against the cured film, and the susceptibility to fingerprints was visually determined. Evaluation was based on the following criteria. Table 1 shows the results.
◯: Fingerprints are hard to adhere, or fingerprints are inconspicuous even if adhered.
x: Fingerprints are clearly attached.

(Fingerprint wiping ability)
After the above-mentioned fingerprint adhesion test, the adhered fingerprints were wiped off with a Kimwipe (trade name, manufactured by Jujo Kimberly Co., Ltd.) five times, and the easiness of wiping off the adhered fingerprints was visually evaluated. Evaluation was based on the following criteria. Table 1 shows the results.
O: Fingerprints can be completely wiped off.
x: Wiping traces of fingerprints spread and are difficult to remove.

(Evaluation of releasability)
The releasability of the cured film was evaluated by a tape peeling test. Evaluation was based on the following criteria. Table 1 shows the results.
◯: Easily peeled off or not adhered.
x: The adhesive layer of the tape adheres.

※ＰＦＰＥ含有化合物を未添加で成膜した硬化膜

* Cured film formed without adding PFPE-containing compound

As can be seen from the results of the Examples, obtained from coating agents containing PFPE-containing compounds (C), (D), (E), (G), (J), and (M) of the present disclosure, respectively The treated substrate having a cured film has a clean appearance, good touch feeling, high antifouling properties, that is, particularly excellent water repellency, excellent fingerprint adhesion and fingerprint wiping properties, and excellent mold releasability. rice field. On the other hand, as understood from the comparative examples, the treated substrates having cured films obtained from the coating agents containing the PFPE-containing compounds (N) and (O), respectively, had all the evaluation items shown in the examples. could not be satisfied, and in particular, sufficient performance was not obtained with respect to water repellency.

The fluoropolyether group-containing epoxy compound of the present disclosure can be used for a wide variety of substrates, for example, cover windows of foldable displays, rollable displays and bending displays; devices such as mobile phones and personal digital assistants; touch panel sheets; For surface treatment of interior goods (specifically, the interior of the car seat and its back side, the ceiling, wall and floor of the car, the dashboard and its lower part, the panel around the driver's seat, switches, levers, etc., the inside of the trunk), etc. , can be widely used.

Claims (25)

Formula (1) or Formula (2) below:

[In the formula:
each R ^A is independently R ^F1 —X ^a —, R ^E _m —X ^b —, or a monovalent group;
R ^F1 is Rf ¹ —R ^F —O _q —;
R ^F2 is -Rf ² _p -R ^F -O _q -,
Rf ¹ is a C _1-16 alkyl group optionally substituted by one or more fluorine atoms,
Rf ² is a C _1-6 alkylene group optionally substituted by one or more fluorine atoms,
R ^F is each independently a divalent fluoropolyether group,
p is 0 or 1,
each q is independently 0 or 1;
each X ^a is independently a single bond or a divalent organic group,
each R ^E is independently an epoxy group-containing group;
X ^b are each independently a divalent to 9-valent group containing a siloxane bond,
Each m is independently an integer from 1 to 8. ]
A compound represented by Each R ^F is independently of the formula:
- (OC ₆ F ₁₂ ) _a - (OC ₅ F ₁₀ ) _b - (OC ₄ F ₈ ) _c - (OC ₃ R ^Fa ₆ ) _d - (OC ₂ F ₄ ) _e - (OCF ₂ ) _f -
[In the formula:
R ^Fa is independently at each occurrence a hydrogen atom, a fluorine atom, or a chlorine atom;
a, b, c, d, e and f are each independently integers from 0 to 200, and the sum of a, b, c, d, e and f is 1 or more. The order of existence of each repeating unit bracketed with a, b, c, d, e or f is arbitrary in the formula. ]
The compound according to claim 1, which is a group represented by: 3. The compound of claim 2, wherein ^RFa is a fluorine atom. R ^F is independently at each occurrence the following formula (f1), (f2), (f3), (f4), (f5) or (f6):
-(OC ₃ F ₆ ) _d -(OC ₂ F ₄ ) _e - (f1)
[In the formula, d is an integer of 1 to 200, and e is 0 or 1. ],
-(OC ₄ F ₈ ) _c -(OC ₃ F ₆ ) _d -(OC ₂ F ₄ ) _e -(OCF ₂ ) _f - (f2)
[Wherein, c and d are each independently an integer of 0 to 30;
e and f are each independently an integer from 1 to 200;
the sum of c, d, e and f is an integer from 10 to 200;
The order of existence of each repeating unit bracketed with subscript c, d, e or f is arbitrary in the formula. ],
-(R ⁶ -R ⁷ ) _g - (f3)
[wherein R ⁶ is OCF ₂ or OC ₂ F ₄ ;
R ⁷ is a group selected from OC ₂ F ₄ , OC ₃ F ₆ , OC ₄ F ₈ , OC ₅ F ₁₀ and OC ₆ F ₁₂ , or two or three groups selected from these groups. is a combination of groups;
g is an integer from 2 to 100; ],
—(R ⁶ —R ⁷ ) _g —R ^r —(R ^7′ —R ^6′ ) _g′ − (f4)
[wherein R ⁶ is OCF ₂ or OC ₂ F ₄ ;
R ⁷ is a group selected from OC ₂ F ₄ , OC ₃ F ₆ , OC ₄ F ₈ , OC ₅ F ₁₀ and OC ₆ F ₁₂ or 2 independently selected from these groups or a combination of three groups,
R ^6' is OCF ₂ or OC ₂ F ₄ ;
R ^7′ is a group selected from OC ₂ F ₄ , OC ₃ F ₆ , OC ₄ F ₈ , OC ₅ F ₁₀ and OC ₆ F ₁₂ or independently selected from these groups a combination of two or three groups,
g is an integer from 2 to 100,
g' is an integer from 2 to 100,
^Rr is

(In the formula, * indicates the binding position.)
is. ];
- (OC ₆ F ₁₂ ) _a - (OC ₅ F ₁₀ ) _b - (OC ₄ F ₈ ) _c - (OC ₃ F ₆ ) _d - (OC ₂ F ₄ ) _e - (OCF ₂ ) _f - (f5)
[Wherein, e is an integer of 1 or more and 200 or less, a, b, c, d and f are each independently an integer of 0 or more and 200 or less, and a, b, c, d, The order of existence of each repeating unit bracketed with e or f is arbitrary in the formula. ]
- (OC ₆ F ₁₂ ) _a - (OC ₅ F ₁₀ ) _b - (OC ₄ F ₈ ) _c - (OC ₃ F ₆ ) _d - (OC ₂ F ₄ ) _e - (OCF ₂ ) _f - (f6)
[Wherein, f is an integer of 1 or more and 200 or less, a, b, c, d and e are each independently an integer of 0 or more and 200 or less, and a, b, c, d, The order of existence of each repeating unit bracketed with e or f is arbitrary in the formula. ]
The compound according to claim 1, which is a group represented by: Rf ¹ is independently at each occurrence a C _1-16 perfluoroalkyl group;
Rf ² is independently at each occurrence a C _1-6 perfluoroalkylene group;
A compound according to claim 1 . Each X ^a is independently represented by the following formula:
-(CX ¹²¹ X ¹²² ) _x1 -(X ^a1 ) _y1 -(CX ¹²³ X ¹²⁴ ) _z1 -
[In the formula,
X ¹²¹ to X ¹²⁴ are each independently H, F, OH or —OSi(OR ¹²¹ ) ₃ (wherein the three R ¹²¹ are each independently an alkyl group having 1 to 4 carbon atoms is.) and
X ^a1 is -C(=O)NH-, -NHC(=O)-, -O-, -C(=O)O-, -OC(=O)-, -OC(=O)O- , or -NHC(=O)NH-,
x1 is an integer of 0-10, y1 is 0 or 1, and z1 is an integer of 1-10. ]
The compound according to claim 1, which is a group represented by: 2. The compound according to claim 1, wherein each X ^a is independently a group represented by -(CH ₂ ) _m22 - (wherein m22 is an integer of 1 to 3). Each R ^E is independently represented by the following formula:
-X ^c -R ^E1
[In the formula,
X ^c is a single bond or a divalent group,
R ^E1 is an epoxy group or an alicyclic epoxy group. ]
The compound according to claim 1, which is a group represented by: The cycloaliphatic epoxy group has the formula:

[In the formula, n is an integer of 1 to 5. ]
The compound according to claim 8, which is a group represented by X ^c is the following formula:
-(C _a H _2a ) _n1 -(R ⁵ ) _n2 -
[In the formula,
a is an integer of 1 to 6 independently for each (C _a H _2a ) unit;
R ⁵ each independently represents -O-, -C(=O)NH-, -NHC(=O)-, -C(=O)O-, -OC(=O)-, -OC( =O)O- or -NHC(=O)NH-,
n1 is an integer from 0 to 6,
n2 is an integer from 0 to 6,
The order of existence of each repeating unit bracketed with n1 and n2 is arbitrary in the formula. ]
The compound according to claim 8, which is a group represented by X ^c is the following formula:
-(C _a H _2a ) _n3 -(R ⁵ ) _n2 -(C _a H _2a ) _n4 -
[In the formula,
each a (C _a H _2a ) is independently an integer of 1 to 6;
R ⁵ is -O-,
n2 is 0 or 1,
n3 is 0 or 1,
n4 is 0 or 1,
At least one of n2, n3 and n4 is one. ]
The compound according to claim 8, which is a group represented by Each ^Xb is independently represented by the following formula:
-X ^d -R ^S -
[In the formula,
X ^d is a single bond or a divalent group,
R ^s is a 2- to 9-valent siloxane group. ]
The compound according to claim 1, which is a group represented by: R ^S is the following formula (s1), (s2), or (s3):

[In the formula,
each R ³ is independently a hydrogen atom or a C _1-6 alkyl group;
R ⁴ is a single bond, a hydrogen atom, or a C _1-6 alkyl group;
m1 is an integer from 1 to 20,
m2 is an integer from 1 to 8,
m3 is an integer from 0 to 12,
The order of existence of each unit enclosed in parentheses is arbitrary in the formula,
The bond marked with * is attached to ^Xd . ]
13. The compound according to claim 12, which is a group represented by R ^S is represented by the following formula (s1) or (s3′):

[In the formula,
each R ³ is independently a hydrogen atom or a C _1-6 alkyl group;
m1 is an integer from 1 to 20,
m2 is an integer of 3 to 5,
The bond marked with * is attached to ^Xd . ]
13. The compound according to claim 12, which is a group represented by X ^d has the formula:
-(C _b H _2b ) _r1 -(R ¹⁰ ) _r2 -
[In the formula,
b is an integer of 1 to 6 independently for each (C _b H _2b ) unit;
R ¹⁰ each independently represents -O-, -C(=O)NH-, -NHC(=O)-, -C(=O)O-, -OC(=O)-, -OC( =O) O- or -NHC(=O)NH- r1 is an integer of 0 to 6,
r2 is an integer from 0 to 6,
The order of existence of each repeating unit bracketed with r1 and r2 is arbitrary in the formula. ]
13. The compound according to claim 12, which is a group represented by X ^d has the formula:
-C _{b H2b} -
[In the formula,
b is an integer from 1 to 6; ]
13. The compound according to claim 12, which is a group represented by The compound according to claim 1, wherein each m is independently an integer from 1 to 3. 2. The compound of claim 1, wherein each R ^A is independently R ^E _m -X ^b -. A surface treatment agent comprising one or more compounds according to claim 1. A curable composition comprising a compound of claim 1; and a matrix-forming composition. 20. A curable composition comprising the surface treatment agent of claim 19; and a matrix-forming composition. An article comprising a substrate and a layer formed on the surface of the substrate with the surface treatment agent according to claim 19. An article comprising a substrate and a layer formed from the curable composition of claim 20 on the surface of the substrate. 23. The article according to claim 22, wherein said article is an optical member. 24. The article according to claim 23, wherein said article is an optical member.