Ion complex material having function of inhibiting adhesion of biological substance and method for manufacturing the same

Patent metadata

Field	Value
Publication number	US-11345827-B2
Application number	US-201414896623-A
Country	US
Kind code	B2
Filing date	Jun 9, 2014
Priority date	Jun 7, 2013
Publication date	May 31, 2022
Grant date	May 31, 2022

Abstract

This is to provide a coating film having a function of inhibiting adhesion of a biological substance, a method for manufacturing the coating film, a copolymer obtainable by polymerizing a specific monomer mixture, a composition for forming a coating film having a specific composition, a method for manufacturing a varnish containing a copolymer to be used as a raw material of the composition for forming a coating film which is used for forming said film, and a sol for forming the coating film. In particular, this is to provide a coating film obtained by the method comprising a process of applying a composition for forming a coating film which comprises a copolymer comprising a recurring unit containing an organic group of the formula (a) and a recurring unit containing an organic group of the formula (b) and a solvent onto a substrate; and a process of drying at a temperature of −200° C. to 200° C. (wherein U a1 , U a2 , U b1 , U b2 and U b3 , and An − are as defined in the present specification and the claims).

First claim

The invention claimed is:

1. A coating film obtained by a method comprising
a process of applying a composition for forming a coating film which comprises
a random copolymer comprising a recurring unit containing an organic group of the following formula (a) and a recurring unit containing an organic group of the following formula (b):

wherein
U a1 and U a2 each independently represent a hydrogen atom or a linear or branched alkyl group having 1 to 5 carbon atoms,
U b1 , U b2 , and U b3 are the same and each represent a hydrogen atom, a methyl group, or an ethyl group,
An − represents an anion selected from the group consisting of a halide ion, an inorganic acid ion, a hydroxide ion and an isothiocyanate ion, and
the recurring unit containing an organic group of the formula (a) in the random copolymer is 20 mol % to 80 mol % relative to the random copolymer, and

a solvent onto a substrate, wherein the composition for forming a coating film is adjusted to a pH of 3.5 to 8.5 by adding a pH adjusting agent prior to applying the composition for forming a coating film onto the substrate; and
a process of drying the coating composition at a temperature of −200° C. to 150° C. to form the coating film,
wherein the thickness of the coating film is 10 to 1,000 Å, and
wherein the film has a function of inhibiting adhesion of a biological substance.

2. The coating film according to claim 1 , wherein the solvent comprises water or an alcohol.

3. The coating film according to claim 1 , wherein a concentration of the random copolymer in the composition for forming a coating film is 0.01% by mass to 4% by mass.

4. The coating film according to claim 1 , wherein the substrate is selected from the group consisting of glass, a metal containing compound, a semi-metal containing compound and a resin.

5. The coating film according to claim 1 , wherein the random copolymer comprises recurring units of the following formula (a1) and the formula (b1):

wherein T a , T b , U a1 , and U a2 each independently represent a hydrogen atom or a linear or branched alkyl group having 1 to 5 carbon atoms, U b1 , U b2 , and U b3 are the same and each represent a hydrogen atom, a methyl group, or an ethyl group, Q a and Q b each independently represent a single bond, an ester bond or an amide bond, R a and R b each independently represent a linear or branched alkylene group having 1 to 10 carbon atoms which may be substituted by a halogen atom, An − represents an anion selected from the group consisting of a halide ion, an inorganic acid ion, a hydroxide ion and an isothiocyanate ion, and m is an integer of 0 to 6.

6. The coating film according to claim 5 , wherein m is 1, and R a and R b each independently represent an ethylene group or a propylene group.

7. The coating film according to claim 1 , wherein the method further comprises a process of washing a film obtained after the process of drying with an aqueous solution containing an electrolyte.

8. A method for manufacturing a coating film comprising
a process of applying a composition for forming a coating film which comprises
a random copolymer comprising a recurring unit containing an organic group of the following formula (a) and a recurring unit containing an organic group of the following formula (b):

wherein U a1 and U a2 each independently represent a hydrogen atom or a linear or branched alkyl group having 1 to 5 carbon atoms, U b1 , U b2 , and U b3 are the same and each represent a hydrogen atom, a methyl group, or an ethyl group, An − represents an anion selected from the group consisting of a halide ion, an inorganic acid ion, a hydroxide ion and an isothiocyanate ion, and
wherein the recurring unit containing an organic group of the formula (a) in the random copolymer is 20 mol % to 80 mol % relative to the random copolymer, and
a solvent

onto a substrate, wherein the composition for forming a coating film is adjusted to a pH of 3.5 to 8.5 by adding a pH adjusting agent prior to applying the composition for forming a coating film onto the substrate; and
a process of drying the composition at a temperature of −200° C. to 150° C. to form the coating film,
wherein the thickness of the coating film is 10 to 1,000 Å.

9. The coating film according to claim 1 , wherein U a1 and U a2 each represent a hydrogen atom.

10. The coating film according to claim 5 , wherein U a1 and U a2 each represent a hydrogen atom.

11. The coating film according to claim 1 , wherein the pH adjusting agent is an organic amine, an alkali metal hydroxide, an alkali metal halide, an inorganic acid, a quaternary ammonium cation, or a mixture thereof.

12. The coating film according to claim 1 , wherein the pH adjusting agent is ammonia, diethanolamine, pyridine, N-methyl-D-glucamine, tris(hydroxymethyl)aminomethane, potassium hydroxide, sodium hydroxide, potassium chloride, sodium chloride, sulfuric acid, phosphoric acid, hydrochloric acid, carbonic acid or an alkali metal salt thereof, choline, or a mixture thereof.

13. The coating film according to claim 1 , wherein the composition for forming a coating film is adjusted to a pH of 4 to 8 by adding a pH adjusting agent prior to applying the composition for forming a coating film onto the substrate.

Assignees

• Nissan Chemical Ind Ltd

Inventors

• Hiroi Yoshiomi
• Otani Ayako
• Kishioka Takahiro
• Nishino Taito
• Ozawa Tomoyuki

Classifications

• C08L43/02

  Homopolymers or copolymers of monomers containing phosphorus · CPC title

• C08F230/02

  containing phosphorus · CPC title

• C09D201/02

  characterised by the presence of specified groups {, e.g. terminal or pendant functional groups} · CPC title

• C08L101/02

  characterised by the presence of specified groups {, e.g. terminal or pendant functional groups} · CPC title

• C09D133/14 Primary

  of esters containing halogen, nitrogen, sulfur or oxygen atoms in addition to the carboxy oxygen · CPC title