JPWO2020162324A5 - - Google Patents
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- JPWO2020162324A5 JPWO2020162324A5 JP2020571142A JP2020571142A JPWO2020162324A5 JP WO2020162324 A5 JPWO2020162324 A5 JP WO2020162324A5 JP 2020571142 A JP2020571142 A JP 2020571142A JP 2020571142 A JP2020571142 A JP 2020571142A JP WO2020162324 A5 JPWO2020162324 A5 JP WO2020162324A5
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- ocf
- curable composition
- composition according
- hard coat
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- 239000010702 perfluoropolyether Substances 0.000 claims description 6
- 239000011248 coating agent Substances 0.000 claims description 5
- 238000000576 coating method Methods 0.000 claims description 5
- 239000000758 substrate Substances 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 230000001678 irradiating effect Effects 0.000 claims description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 8
- 239000000178 monomer Substances 0.000 description 6
- 229910044991 metal oxide Inorganic materials 0.000 description 4
- 150000004706 metal oxides Chemical class 0.000 description 4
- 239000002245 particle Substances 0.000 description 4
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 4
- 229910001887 tin oxide Inorganic materials 0.000 description 4
- 239000011787 zinc oxide Substances 0.000 description 4
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 3
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- 229910003437 indium oxide Inorganic materials 0.000 description 2
- PJXISJQVUVHSOJ-UHFFFAOYSA-N indium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[In+3].[In+3] PJXISJQVUVHSOJ-UHFFFAOYSA-N 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 description 1
- 239000002216 antistatic agent Substances 0.000 description 1
- 229910052733 gallium Inorganic materials 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000006353 oxyethylene group Chemical group 0.000 description 1
- -1 poly(oxyalkylene) Polymers 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- 239000011164 primary particle Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
Description
すなわち本発明は、第１観点として、
（ａ）活性エネルギー線硬化性多官能モノマー１００質量部、
（ｂ）ポリ（オキシパーフルオロアルキレン）基を含むパーフルオロポリエーテルであって、その分子鎖の両末端に、ウレタン結合を介して、活性エネルギー線重合性基を有するパーフルオロポリエーテル（但し、前記ポリ（オキシパーフルオロアルキレン）基と前記ウレタン結合との間にポリ（オキシアルキレン）基を有するパーフルオロポリエーテルを除く。）０．０５質量部～１０質量部、
（ｃ）帯電防止剤として金属酸化物粒子５質量部～１００質量部、及び
（ｄ）活性エネルギー線によりラジカルを発生する重合開始剤１質量部～２０質量部、
を含む、硬化性組成物に関する。
第２観点として、前記（ｂ）パーフルオロポリエーテルは、その分子鎖の両末端それぞれにおいてウレタン結合を介して活性エネルギー線重合性基を少なくとも２つ有する、第１観点に記載の硬化性組成物に関する。
第３観点として、前記（ｂ）パーフルオロポリエーテルは、その分子鎖の両末端それぞれにおいてウレタン結合を介して活性エネルギー線重合性基を少なくとも３つ有する、第２観点に記載の硬化性組成物に関する。
第４観点として、前記ポリ（オキシパーフルオロアルキレン）基が、繰り返し単位－［ＯＣＦ２］－及び繰り返し単位－［ＯＣＦ２ＣＦ２］－の双方を有し、これら繰り返し単位をブロック結合、ランダム結合、又は、ブロック結合及びランダム結合にて結合してなる基である、第１観点乃至第３観点のうち何れか一つに記載の硬化性組成物に関する。
第５観点として、前記（ｂ）パーフルオロポリエーテルが下記式［１］で表される部分構造を有する、第４観点に記載の硬化性組成物に関する。
前記繰り返し単位－［ＯＣＦ２ＣＦ２］－及び前記繰り返し単位－［ＯＣＦ２］－は、ブロック結合、ランダム結合、又は、ブロック結合及びランダム結合にて結合してなる。
第６観点として、前記（ａ）多官能モノマーが、オキシエチレン変性多官能モノマーである、第１観点乃至第５観点のうち何れか一つに記載の硬化性組成物に関する。
第７観点として、前記（ａ）多官能モノマーの平均オキシエチレン変性量が、該多官能モノマーの重合性基１ｍｏｌに対し３ｍｏｌ未満である第６観点に記載の硬化性組成物に関する。
第８観点として、前記（ａ）多官能モノマーが、多官能（メタ）アクリレート化合物（但し、後述の多官能ウレタン（メタ）アクリレート化合物を除く）及び多官能ウレタン（メタ）アクリレート化合物からなる群から選ばれる少なくとも１つを含む、第１観点乃至第７観点のうち何れか一つに記載の硬化性組成物に関する。
第９観点として、前記（ｃ）金属酸化物粒子がスズドープ酸化インジウム、フッ素ドープ酸化スズ、アンチモンドープ酸化スズ、リンドープ酸化スズ、ガリウムドープ酸化亜鉛、アルミニウムドープ酸化亜鉛、アンチモンドープ酸化亜鉛、インジウムドープ酸化亜鉛、酸化亜鉛ドープ酸化インジウム、及び酸化インジウムガリウム亜鉛からなる群から選ばれる少なくとも１つを含む、第１観点乃至第８観点のうち何れか一つに記載の硬化性組成物に関する。
第１０観点として、前記（ｃ）金属酸化物粒子がリンドープ酸化スズを含む、第１観点乃至第９観点のうち何れか一つに記載の硬化性組成物に関する。
第１１観点として、前記（ｃ）金属酸化物粒子の一次粒子径が４ｎｍ～１００ｎｍである、第１観点乃至第１０観点のうち何れか一つに記載の硬化性組成物に関する。
第１２観点として、さらに（ｅ）溶媒を含む、第１観点乃至第１１観点のうち何れか一つに記載の硬化性組成物に関する。
第１３観点として、第１観点乃至第１１観点のうち何れか一つに記載の硬化性組成物より得られる硬化膜に関する。
第１４観点として、フィルム基材の少なくとも一方の面にハードコート層を備えるハードコートフィルムであって、該ハードコート層が第１３観点に記載の硬化膜からなる、ハードコートフィルムに関する。
第１５観点として、前記ハードコート層が１μｍ～１５μｍの層厚を有する、第１４観点に記載のハードコートフィルムに関する。
第１６観点として、フィルム基材の少なくとも一方の面にハードコート層を備えるハードコートフィルムの製造方法であって、第１観点乃至第１２観点のうち何れか一つに記載の硬化性組成物をフィルム基材上に塗布し塗膜を形成する工程と、該塗膜に活性エネルギー線を照射し硬化する工程とを含む、ハードコートフィルムの製造方法に関する。
That is, the present invention, as a first aspect,
(a) 100 parts by mass of an active energy ray-curable polyfunctional monomer,
(b) A perfluoropolyether containing a poly(oxyperfluoroalkylene) group and having an active energy ray-polymerizable group at both ends of its molecular chain via a urethane bond (provided that 0.05 parts by mass to 10 parts by mass, excluding perfluoropolyethers having a poly(oxyalkylene) group between the poly(oxyperfluoroalkylene) group and the urethane bond;
(c) 5 parts by mass to 100 parts by mass of metal oxide particles as an antistatic agent, and (d) 1 part by mass to 20 parts by mass of a polymerization initiator that generates radicals by active energy rays,
It relates to a curable composition comprising
As a second aspect, the curable composition according to the first aspect, wherein the (b) perfluoropolyether has at least two active energy ray-polymerizable groups via urethane bonds at both ends of its molecular chain. Regarding.
As a third aspect, the curable composition according to the second aspect, wherein the (b) perfluoropolyether has at least three active energy ray-polymerizable groups via urethane bonds at each of both ends of its molecular chain. Regarding.
As a fourth aspect, the poly(oxyperfluoroalkylene) group has both repeating units -[OCF 2 ]- and repeating units -[OCF 2 CF 2 ]-, and these repeating units are block-bonded or random-bonded. , or the curable composition according to any one of the first aspect to the third aspect, which is a group formed by bonding with a block bond and a random bond.
As a fifth aspect, it relates to the curable composition according to the fourth aspect, wherein the (b) perfluoropolyether has a partial structure represented by the following formula [1].
The repeating unit -[OCF 2 CF 2 ]- and the repeating unit -[OCF 2 ]- are bound by block bond, random bond, or block bond and random bond .
As a sixth aspect, the curable composition according to any one of the first to fifth aspects, wherein the (a) polyfunctional monomer is an oxyethylene-modified polyfunctional monomer.
As a seventh aspect, it relates to the curable composition according to the sixth aspect , wherein the average amount of oxyethylene modification of the polyfunctional monomer (a) is less than 3 mol per 1 mol of the polymerizable group of the polyfunctional monomer.
As an eighth aspect, the (a) polyfunctional monomer is from the group consisting of polyfunctional (meth)acrylate compounds (excluding polyfunctional urethane (meth)acrylate compounds described later) and polyfunctional urethane (meth)acrylate compounds It relates to the curable composition according to any one of the first to seventh aspects, including at least one selected.
As a ninth aspect, the (c) metal oxide particles are tin-doped indium oxide, fluorine-doped tin oxide, antimony-doped tin oxide, phosphorus-doped tin oxide, gallium-doped zinc oxide, aluminum-doped zinc oxide, antimony-doped zinc oxide, and indium-doped oxide. The curable composition according to any one of the first to eighth aspects, comprising at least one selected from the group consisting of zinc, zinc oxide-doped indium oxide, and indium gallium zinc oxide.
As a tenth aspect, the curable composition according to any one of the first to ninth aspects, wherein the (c) metal oxide particles contain phosphorus-doped tin oxide.
An eleventh aspect relates to the curable composition according to any one of the first to tenth aspects, wherein the (c) metal oxide particles have a primary particle size of 4 nm to 100 nm.
As a twelfth aspect, it relates to the curable composition according to any one of the first to eleventh aspects, further comprising (e) a solvent.
A thirteenth aspect relates to a cured film obtained from the curable composition according to any one of the first to eleventh aspects.
As a fourteenth aspect, the present invention relates to a hard coat film comprising a hard coat layer on at least one surface of a film substrate, wherein the hard coat layer comprises the cured film according to the thirteenth aspect.
As a fifteenth aspect, it relates to the hard coat film according to the fourteenth aspect, wherein the hard coat layer has a layer thickness of 1 μm to 15 μm.
As a sixteenth aspect, a method for producing a hard coat film comprising a hard coat layer on at least one surface of a film substrate, wherein the curable composition according to any one of the first to twelfth aspects is The present invention relates to a method for producing a hard coat film, comprising the steps of coating a film substrate to form a coating film, and curing the coating film by irradiating it with active energy rays.
Claims (2)
ｎは、繰り返し単位－［ＯＣＦ２ＣＦ２］－の数と、繰り返し単位－［ＯＣＦ２］－の数との総数であって、５～３０の整数を表し、
前記繰り返し単位－［ＯＣＦ２ＣＦ２］－及び前記繰り返し単位－［ＯＣＦ２］－は、ブロック結合、ランダム結合、又は、ブロック結合及びランダム結合にて結合してなる。） 5. The curable composition according to claim 4, wherein the (b) perfluoropolyether has a partial structure represented by the following formula [1].
n is the total number of repeating units -[OCF 2 CF 2 ]- and repeating units -[OCF 2 ]- and represents an integer of 5 to 30;
The repeating unit -[OCF 2 CF 2 ]- and the repeating unit -[OCF 2 ]- are bound by block bond, random bond, or block bond and random bond . )
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2019020177 | 2019-02-06 | ||
| JP2019020177 | 2019-02-06 | ||
| PCT/JP2020/003477 WO2020162324A1 (en) | 2019-02-06 | 2020-01-30 | Curable composition for antistatic hard coating |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPWO2020162324A1 JPWO2020162324A1 (en) | 2021-12-09 |
| JPWO2020162324A5 true JPWO2020162324A5 (en) | 2023-01-31 |
Family
ID=71947053
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2020571142A Pending JPWO2020162324A1 (en) | 2019-02-06 | 2020-01-30 | Curable composition for antistatic hard coat |
Country Status (5)
| Country | Link |
|---|---|
| JP (1) | JPWO2020162324A1 (en) |
| KR (1) | KR20210124271A (en) |
| CN (1) | CN113412190B (en) |
| TW (1) | TWI828851B (en) |
| WO (1) | WO2020162324A1 (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP7367316B2 (en) * | 2019-03-26 | 2023-10-24 | 三菱ケミカル株式会社 | Highly hydrophobic active energy ray-curable composition and resin molded product |
| WO2022209867A1 (en) * | 2021-04-02 | 2022-10-06 | 日産化学株式会社 | Antistatic hardcoat layer, and curable composition |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4779293B2 (en) * | 2003-10-21 | 2011-09-28 | Ｔｄｋ株式会社 | Hard coating agent composition and optical information medium using the same |
| JP5206464B2 (en) * | 2008-03-26 | 2013-06-12 | Ｊｓｒ株式会社 | Compound having perfluoropolyether group, urethane group and (meth) acryloyl group |
| JP2013076029A (en) * | 2011-09-30 | 2013-04-25 | Tdk Corp | Hard coat agent composition and hard coat film using the same |
| JP6203715B2 (en) | 2012-06-22 | 2017-09-27 | ソマール株式会社 | Energy ray curable resin composition, cured product and laminate |
| JP2015054461A (en) * | 2013-09-12 | 2015-03-23 | 富士フイルム株式会社 | Hard coat film |
| KR101813024B1 (en) * | 2013-11-11 | 2017-12-28 | 디아이씨 가부시끼가이샤 | Active energy ray-curable composition, cured product thereof, and article having cured coating film thereof |
| JP6340210B2 (en) * | 2014-02-27 | 2018-06-06 | デクセリアルズ株式会社 | Surface conditioner and article using the same |
| JP6802528B2 (en) * | 2015-04-07 | 2020-12-16 | 日産化学株式会社 | Curable composition for scratch resistant coating |
| JP2017008128A (en) * | 2015-06-16 | 2017-01-12 | ユニマテック株式会社 | Active energy ray curable resin composition |
| JP7041405B2 (en) * | 2017-09-01 | 2022-03-24 | 日産化学株式会社 | Curable Composition for Stretchable Scratch Resistant Coating |
| JP7116171B2 (en) * | 2018-07-05 | 2022-08-09 | 日産化学株式会社 | Curable composition for flexible coating |
-
2020
- 2020-01-30 CN CN202080013211.2A patent/CN113412190B/en active Active
- 2020-01-30 KR KR1020217026126A patent/KR20210124271A/en unknown
- 2020-01-30 JP JP2020571142A patent/JPWO2020162324A1/en active Pending
- 2020-01-30 WO PCT/JP2020/003477 patent/WO2020162324A1/en active Application Filing
- 2020-02-03 TW TW109103131A patent/TWI828851B/en active
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