Surface treatment liquid and surface treatment method

Patent metadata

Field	Value
Publication number	US-11279833-B2
Application number	US-201816495249-A
Country	US
Kind code	B2
Filing date	Feb 2, 2018
Priority date	Mar 23, 2017
Publication date	Mar 22, 2022
Grant date	Mar 22, 2022

Abstract

The purpose of the present invention is to provide: a surface treatment liquid that is capable of favorably hydrophilizing or hydrophobing surfaces of an object to be treated without having to include a film forming resin; and a surface treatment method using the surface treatment liquid. The present invention provides a surface treatment liquid which comprises (A) a resin and (C) a solvent, wherein as (A) the resin, a resin is used which has a weight average molecular weight of 100000 or more and contains a functional group I which comprises one group or more selected from the group consisting of a hydroxyl group, a cyano group, and a carboxyl group, and a functional group II which is a hydrophilic group or a hydrophobic group other than the functional group I.

First claim

The invention claimed is:

1. A surface treatment liquid, comprising:
(A) a resin, and
(C) a solvent,
wherein
(A) the resin comprises a functional group I which is one or more groups selected from the group consisting of a hydroxyl group, a cyano group, and a carboxyl group, and a functional group II being a hydrophilic group or a hydrophobic group other than the functional group I, the hydrophobic group being at least one group selected from the group consisting of a silyl group, a siloxane group, an alkyl group having 6 to 20 carbon atoms and having no fluorine atom, and an aromatic hydrocarbon group having 10 to 20 carbon atoms; or
(A) the resin comprises a functional group II being a hydrophilic group or a hydrophobic group comprising one or more groups selected from a hydroxyl group, a cyano group, and a carboxyl group;

wherein (A) the resin has a weight-average molecular weight of 100,000 or more,
wherein the hydrophilic group of the functional group II comprises no polyoxyalkylene group.

2. The surface treatment liquid according to claim 1 , wherein the hydrophobic group is one or more groups selected from the group consisting of a fluorinated hydrocarbon group, a silyl group, and a siloxane group.

3. The surface treatment liquid according to claim 1 , wherein the functional group II is a hydrophobic group, and is derived from a monomer represented by the following formula (A3):
CH 2 ═CR 2 —(CO—O) b —R 6   (A3)

wherein in the formula (A3), R 2 is a hydrogen atom or a methyl group, b is 0 or 1, and R 6 is a fluorinated hydrocarbon group or a group represented by the following formula (A4):
—SiR 7 R 8 —(—O—SiR 7 R 8 —) n —R 9   (A4)

wherein R 7 , R 8 , and R 9 are, each independently, a hydrocarbon group having 1 to 6 carbon atoms, and n is an integer of 0 or more.

4. A surface treatment method, comprising:
applying a surface treatment liquid to a surface of a treatment target, the surface treatment liquid comprising (A) a resin, and (C) a solvent,
wherein
(A) the resin comprises a functional group I which is one or more groups selected from the group consisting of a hydroxyl group, a cyano group, and a carboxyl group, and a functional group II being a hydrophilic group other than the functional group I;

wherein the hydrophilic group of the functional group II is a group represented by the following formula (A1):
—NH—R 1   (A1)

wherein in the formula (Al), R 1 represents an alkyl group having 1 to 4 carbon atoms substituted with one or more groups selected from the group consisting of an amino group, a sulfonic acid group and a hydroxyl group, or a hydrogen atom,
wherein the hydrophilic group of the functional group II comprises no polyoxyalkylene group,
wherein (A) the resin has a weight-average molecular weight of 100,000 or more,
wherein material on the surface to which the surface treatment liquid is to be applied is an inorganic material, and
wherein, when the functional group I is present, (A) the resin has at least one of a hydroxyl group and a cyano group.

5. A surface treatment liquid, comprising:
(A) a resin, and
(C) a solvent,
wherein
(A) the resin comprises a functional group I which is one or more groups selected from the group consisting of a hydroxyl group, a cyano group, and a carboxyl group, and a functional group II being a hydrophilic group other than the functional group I, or
(A) the resin comprises a functional group II being a hydrophilic group comprising one or more groups selected from a hydroxyl group, a cyano group, and a carboxyl group,

wherein (A) the resin has a weight-average molecular weight of 100,000 or more, and wherein the hydrophilic group of the functional group II comprises no polyoxyalkylene group,
(A) the resin consists of a constituent unit derived from a monomer represented by the following formula (A5) and a constituent unit other than the constituent unit derived from the monomer represented by the formula (A5):
CH 2 ═CR 2 —CO—NH—R 1   (A5)

wherein in the formula (A5), le is an alkyl group having 1 to 4 carbon atoms substituted with one or more groups selected from the group consisting of an amino group, a sulfonic acid group, and a hydroxyl group, or a hydrogen atom; and R 2 is a hydrogen atom or a methyl group.

6. A method of using the surface treatment liquid according to claim 5 , for suppressing adsorption of protein onto a surface of a treatment target.

7. A method of using the surface treatment liquid according to claim 5 , for suppressing adhesion of cells on a surface of a treatment target.

8. A surface treatment method comprising applying the surface treatment liquid according to claim 5 to the surface of a treatment target.

9. The surface treatment method according to claim 8 , wherein the method comprises rinsing a portion of the treatment target to which the surface treatment liquid is applied.

10. The surface treatment method according to claim 8 , wherein the treatment target is a substrate, the applying of the surface treatment liquid is carried out by spin coating.

11. The surface treatment method according to claim 8 , wherein material on the surface to which the surface treatment liquid is to be applied is an organic material, (A) the resin has at least one of a hydroxyl group and a carboxyl group, as the functional group I.

12. The surface treatment method according to claim 8 , wherein material on the surface to which the surface treatment liquid is to be applied is an inorganic material, (A) the resin has at least one of a hydroxyl group and a cyano group, as the functional group I.

13. The surface treatment method according to claim 8 , wherein protein adsorption on the surface of the treatment target is suppressed using the surface treatment liquid.

14. The surface treatment method according to claim 8 , wherein the cell adhesion on the surface of the treatment target is suppressed using the surface treatment liquid.

15. The surface treatment liquid according to claim 5 , wherein the constituent unit other than the constituent unit derived from the monomer represented by the formula (A5) comprises a constituent unit derived from a monomer represented by the following formula (A2):
CH 2 ═CR 2 —(R 3 ) a —CO—R 4   (A2)

wherein in the formula (A2), R 2 is a hydrogen atom or a methyl group, R 3 is a divalent hydrocarbon group, a is 0 or 1, R 4 is —OH, —O—R 5 , or —NH—R 5 , R 5 is a hydrocarbon group substituted with one or more functional groups selected from the group consisting of a hydroxyl group, a cyano group, and a carboxyl group.

Assignees

• Tokyo Ohka Kogyo Co Ltd

Inventors

• Senzaki Takahiro
• Noguchi Takuya
• Ohsaka Takashi

Classifications

• C09D133/24

  Homopolymers or copolymers of amides or imides · CPC title

• C08F220/56

  Acrylamide; Methacrylamide · CPC title

• C09D5/00 Primary

  Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced {(electrically insulating plastics, resins or waxes H01B3/30)}; Filling pastes · CPC title

• C08F220/585

  and containing other heteroatoms, e.g. 2-acrylamido-2-methylpropane sulfonic acid [AMPS] · CPC title

• C09D133/16

  Homopolymers or copolymers of esters containing halogen atoms · CPC title