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Ion Complex Material Having Ability To Inhibit Adhesion Of Biological Materials And Method For Producing Same

Abstract: The present invention provides a copolymer or the like obtained by polymerizing a monomer mixture including at least compounds represented by formulas (A) (B) and (C) (in the formulas Ta,Tb Tb,Ua1,Ua2,Ub1,Ub2 and Ub3 Qa,Qb and Qc Ra,Rb and Rb An and m are as defined in the description and claims). The copolymer of the present invention can be utilized as an ion complex material having an exceptional ability to inhibit adhesion of biological materials.

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Notices, Deadlines & Correspondence

Patent Information

Application #
Filing Date
04 July 2017
Publication Number
50/2017
Publication Type
INA
Invention Field
POLYMER TECHNOLOGY
Status
Email
Parent Application

Applicants

NISSAN CHEMICAL INDUSTRIES LTD.
7-1, Kanda Nishiki-cho 3-chome Chiyoda-ku Tokyo 101-0054

Inventors

1. HIROI Yoshiomi
c/o Nissan Chemical Industries Ltd. Materials Research Laboratories 635 Sasakura Fuchu machi Toyama-shi Toyama 9392792
2. ABE Natsuki
c/o Nissan Chemical Industries Ltd. Biological Research Laboratories 1470 Shiraoka Shiraoka-shi Saitama 3490294
3. NISHINO Taito
c/o Nissan Chemical Industries Ltd. Biological Research Laboratories 1470 Shiraoka Shiraoka-shi Saitama 3490294
4. KITAHARA Masaki
c/o Nissan Chemical Industries Ltd. Biological Research Laboratories 1470 Shiraoka Shiraoka-shi Saitama 3490294

Specification

1. A copolymer which is obtainable by polymerizing a monomer mixture containing at least compounds of the following formulae (A), (B) and (C):
wherein
T\ Tb, Tc, Ual, If2, Ubl, Ub2 and Ub3 each independently represent a hydrogen atom or
a linear or branched alkyl group having 1 to 5 carbon atoms;
Qa and Qb each independently represent a single bond, an ester bond or an amide bond, 10 Q° represents a single bond, an ether bond or an ester bond;
Ra and Rb each independently represent a linear or branched alkylene group having 1
to 10 carbon atoms which may be substituted by a halogen atom(s), R° represents a
linear or branched alkyl group having 1 to 18 carbon atoms, a cyclic hydrocarbon
group having 3 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, an 15 aralkyl group having 7 to 14 carbon atoms or an aryloxyalkyl group having 7 to 14
carbon atoms, where the above-mentioned aryl portion may be substituted by a linear
or branched alkyl group having 1 to 5 carbon atoms which may be substituted by a
halogen atom(s);
An" represents an anion selected from the group consisting of a halide ion, an 20 inorganic acid ion, a hydroxide ion and an isothiocyanate ion; and
m represents an integer of 0 to 6.
2. The copolymer according to Claim 1, wherein the copolymer is obtainable by polymerizing a monomer mixture further containing a compound of the following 25 formula (D) or (E):

wherein
Td, Te and Ue each independently represent a hydrogen atom or a linear or branched alkyl group having 1 to 5 carbon atoms;
Rd and Re each independently represent a linear or branched alkylene group having 1 to 10 carbon atoms which may be substituted by a halogen atom(s); and n represents an integer of 1 to 6.
3. A composition for forming a coating film which comprises
(i) a copolymer which contains a recurring unit containing an organic group of the
following formula (a), a recurring unit containing an organic group of the following
formula (b) and a recurring unit containing an organic group of the following formula
(c):
wherein
UaI, Uii2, Ubi, Ub2 and Ub3 each independently represent a hydrogen atom or a linear or
branched alkyl group having 1 to 5 carbon atoms;
Rc represents a linear or branched alkyl group having 4 to 18 carbon atoms, a cyclic
hydrocarbon group having 3 to 10 carbon atoms, an aryl group having 6 to 10 carbon
atoms, an aralkyl group having 7 to 14 carbon atoms or an aryloxyaikyl group having

7 to 14 carbon atoms, where the above-mentioned aryl portion may be substituted by a
linear or branched alkyl group having 1 to 5 carbon atoms which may be substituted
by a halogen atom(s); and
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
(ii) a solvent.
4. The composition according to Claim 3, wherein the copolymer contains recurring units of the following formulae (al), (bl) and (cl):
wherein
Ta, Tb, Tc, Ual, Ua2, Ubl, Ub2 and Ub3 each independently represent a hydrogen atom or
a linear or branched alkyl group having 1 to 5 carbon atoms;
Qa and Qb each independently represent a single bond, an ester bond or an amide bond,
Qc represents a single bond, an ether bond or an ester bond;
Ra and Rb each independently represent a linear or branched alkylene group having 1
to 10 carbon atoms which may be substituted by a halogen atom(s), R° represents a
linear or branched alkyl group having 4 to 18 carbon atoms, an alicyclic hydrocarbon
group having 3 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, an
aralkyl group having 7 to 14 carbon atoms or an aryloxyalkyl group having 7 to 14
carbon atoms, where the above-mentioned aryl portion may be substituted by a linear
or branched alkyl group having 1 to 5 carbon atoms which may be substituted by a
halogen atom(s);
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 represents an integer of 0 to 6.
5. A coating film obtainable by a method which comprises a process of coating a composition for forming a coating film which contains a copolymer containing a recurring unit containing an organic group of the following formula (a), a recurring unit containing an organic group of the following formula (b) and a recurring unit containing an organic group of the following formula (c):
wherein
Ual, Ua\ Ubi, Ub2 and Ub3 each independently represent a hydrogen atom or a linear or
branched alkyl group having 1 to 5 carbon atoms;
Rc represents a linear or branched alkyl group having 4 to 18 carbon atoms, an
alicyclic hydrocarbon group having 3 to 10 carbon atoms, an aryl group having 6 to 10
carbon atoms, an aralkyl group having 7 to 14 carbon atoms or an aryloxyalkyl group
having 7 to 14 carbon atoms, where the above-mentioned aryl portion may be
substituted by a linear or branched alkyl group having 1 to 5 carbon atoms which may
be substituted by a halogen atom(s); and
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
a solvent onto a substrate.
6. The coating film according to Claim 5, wherein the copolymer contains recurring units of the following formulae (al), (bl) and (cl):

wherein
Ta, Tb, Tc, Ua\ U!i2, Ubl, Ub2 and Ub3 each independently represent a hydrogen atom or
a linear or branched alkyl group having 1 to 5 carbon atoms;
Qa and Q' each independently represent a single bond, an ester bond or an amide bond,
Qc represents a single bond, an ether bond or an ester bond;
Rcl and R each independently represent a linear or branched alkylene group having 1
to 10 carbon atoms which may be substituted by a halogen atom(s), Rc represents a
linear or branched alkyl group having 4 to 18 carbon atoms, an alicyclic hydrocarbon
group having 3 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, an
aralkyl group having 7 to 14 carbon atoms or an aryloxyalkyl group having 7 to 14
carbon atoms, where the above-mentioned aryl portion may be substituted by a linear
or branched alkyl group having 1 to 5 carbon atoms which may be substituted by a
halogen atom(s);
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 represents an integer of 0 to 6.
7. The coating film according to Claim 5 or 6, wherein the method contains a process of provisionally adjusting a pH of the composition for forming a coating film.
8. The coating film according to any one of Claims 5 to 7, wherein the method further contains a process of washing the film obtained after a drying process by at least one kind of a solvent selected from the group consisting of water and an aqueous solution containing an eleclrolyte(s).

9. The coating film according to any one of Claims 5 to 8, wherein the film has a function of inhibiting adhesion of a biological substance.
5 10. A sol which comprises a copolymer containing a recurring unit containing an organic group of the following formula (a), a recurring unit containing an organic group of the following formula (b) and a recurring unit containing an organic group of the following formula fc):
wherein
Ual, Ua2, Ubl, Ub2 and Ub3 each independently represent a hydrogen atom or a linear or
branched alkyl group having 1 to 5 carbon atoms;
Rc represents a linear or branched alkyl group having 4 to 18 carbon atoms, an
alicyclic hydrocarbon group having 3 to 10 carbon atoms, an aryl group having 6 to 10
carbon atoms, an aralkyl group having 7 to 14 carbon atoms or an aryloxyalkyl group
having 7 to 14 carbon atoms, where the above-mentioned aryl portion may be
substituted by a linear or branched alkyl group having 1 to 5 carbon atoms which may
be substituted by a halogen atom(s);
An" represents an anion selected from the group consisting of a halide ion, an
inorganic acid ion, a hydroxide ion and an isothiocyanate ion.
11. The sol according to Claim 10, wherein an average particle diameter in particle diameter distribution measured by a dynamic light scattering method is 2 nm or more and 500 nm or less.
12. A method for manufacturing a coating film comprising a process of coating a composition for forming a coating film which comprises a copolymer containing a recurring unit containing an organic group of the following formula (a), a recurring

unit containing an organic group of the following formula fb) and a recurring unit containing an organic group of the following formula (c):
wherein
Ual, Ua , Ubl, Ub2 and Ub3 each independently represent a hydrogen atom or a linear or
branched alkyl group having 1 to 5 carbon atoms;
Rc represents a linear or branched alkyl group having 4 to 18 carbon atoms, a
cycloalkyl group having 3 to 8 carbon atoms, an aryl group having 6 to 10 carbon
atoms, an aralkyl group having 7 to 14 carbon atoms or an aryloxyalkyl group having
7 to 14 carbon atoms, where, the above-mentioned aryl portion may be substituted by
a linear or branched alkyl group having 1 to 5 carbon atoms which may be substituted
by a halogen atom(s); and
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
a solvent, onto a substrate.
13. A method for producing a varnish containing a copolymer which comprises a process of adding dropwise a mixture containing compounds of the following formulae (A), (B) and (C):

wherein
Ta, Tb, Tc, Ua!, Ua2, Ubl, Ub2 and Ub3 each independently represent a hydrogen atom or
a linear or branched alkyl group having 1 to 5 carbon atoms;
Qa and Q1 each independently represent a single bond, an ester bond or an amide bond,
Qc represents a single bond, an ether bond or an ester bond;
Ra and Rb each independently represent a linear or branched alkylene group having 1
to 10 carbon atoms which may be substituted by a halogen atom(s), Rc represents a
linear or branched alkyl group having 4 to 18 carbon atoms, an alicyclic hydrocarbon
group having 3 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, an
aralkyl group having 7 to 14 carbon atoms or an aryloxyalkyl group having 7 to 14
carbon atoms, where, the above-mentioned aryl portion may be substituted by a linear
or branched alkyl group having 1 to 5 carbon atoms which may be substituted by a
halogen atom(s);
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 represents an integer of 0 to 6,
a solvent and a polymerization initiator
to a solvent which has been maintained at a temperature higher than a 10 hour half-life
temperature of the polymerization initiator, and reacting these.
14. A method for producing a copolymer which comprises a process of polymerizing a monomer mixture containing at least compounds of the following formulae (A), (B) and (C):

wherein
Ta, T\ TC, Ual, Ua2, Ubl, Ub2 and Ub3 each independently represent a hydrogen atom or
a linear or branched alkyl group having 1 to 5 carbon atoms;
Q!l and Qb each independently represent a single bond, an ester bond or an amide bond,
Qc represents a single bond, an ether bond or an ester bond;
Ra and R each independently represent a linear or branched alkylene group having 1
to 10 carbon atoms which may be substituted by a halogen atom(s), Rc represents a
linear or branched alkyl group having 1 to 18 carbon atoms, a cyclic hydrocarbon
group having 3 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, an
aralkyl group having 7 to 14 carbon atoms or an aryloxyalkyl group having 7 to 14
carbon atoms, where the above-mentioned aryl portion may be substituted by a linear
or branched alkyl group having 1 to 5 carbon atoms which may be substituted by a
halogen atom(s);
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 represents an integer of 0 to 6.
15. The producing method according to Claim 14, wherein the copolymer is obtainable by polymerizing a monomer mixture which further contains a compound of the following formula (D) or (E):

wherein
T\ T^ and Ue each independently represent a hydrogen atom or a linear or branched
alkyl group having 1 to 5 carbon atoms;
R and Re each independently represent a linear or branched alkylene group having 1
to 10 carbon atoms which may be substituted by a halogen atom(s); and n represents
an integer of 1 to 6.
16. A method for producing a sol which comprises a process of polymerizing a monomer mixture containing at least compounds of the following formulae (A), (B)
wherein
T'1, T\ T°, Ua , Ua~, U , U " and U' each independently represent a hydrogen atom or
a linear or branched alkyl group having 1 to 5 carbon atoms;
Qa and Q1 each independently represent a single bond, an ester bond or an amide bond,
QL represents a single bond, an ether bond or an ester bond;
R'1 and R1 each independently represent a linear or branched alkylene group having 1

to 10 carbon atoms which may be substituted by a halogen atom(s), Rc represents a linear or branched alkyl group having 1 to 18 carbon atoms, a cyclic hydrocarbon group having 3 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, an aralkyl group having 7 to 14 carbon atoms or an aryloxyalkyl group having 7 to 14 carbon atoms, where the above-mentioned aryl portion may be substituted by a linear or branched alkyl group having 1 to 5 carbon atoms which may be substituted by a halogen atom(s);
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 represents an integer of 0 to 6.
17. The copolymer according to Claim 1 or 2, wherein which is for forming a coating film having a function of inhibiting adhesion of a biological substance.
18. The composition according to Claim 3 or 4, which is for forming a coating film having a function of inhibiting adhesion of a biological substance.
19. The sol according to Claim 10 or 11, which is for forming a coating film having a function of inhibiting adhesion of a biological substance.
20. The manufacturing method according to Claim 12, wherein the coating film has a function of inhibiting adhesion of a biological substance.
21. The producing method according to Claim 13, wherein the varnish is for forming a coating film having a function of inhibiting adhesion of a biological substance.
22. The producing method according to Claim 14 or 15, wherein the copolymer is for forming a coating film having a function of inhibiting adhesion of a biological substance.
23. The producing method according to Claim 16, wherein the sol is for forming a coating film having a function of inhibiting adhesion of a biological substance.

Documents

Application Documents

# Name Date
1 Translated Copy of Priority Document [04-07-2017(online)].pdf 2017-07-04
2 Priority Document [04-07-2017(online)].pdf 2017-07-04
3 Power of Attorney [04-07-2017(online)].pdf 2017-07-04
4 Form 5 [04-07-2017(online)].pdf 2017-07-04
5 Form 3 [04-07-2017(online)].pdf 2017-07-04
6 Form 1 [04-07-2017(online)].pdf 2017-07-04
7 Description(Complete) [04-07-2017(online)].pdf_9.pdf 2017-07-04
8 Description(Complete) [04-07-2017(online)].pdf 2017-07-04
9 CLAIMS UNDER RULE 1 (PROVISIO) OF RULE 20 [04-07-2017(online)].pdf 2017-07-04
10 201747023426.pdf 2017-07-11
11 201747023426-Proof of Right (MANDATORY) [22-12-2017(online)].pdf 2017-12-22
12 201747023426-FORM 3 [22-12-2017(online)].pdf 2017-12-22
13 Correspondence by Agent_Form 1_26-12-2017.pdf 2017-12-26
14 201747023426-FORM 18 [26-10-2018(online)].pdf 2018-10-26
15 201747023426-FER.pdf 2019-12-11
16 201747023426-Information under section 8(2) [09-06-2020(online)].pdf 2020-06-09
17 201747023426-FORM 4(ii) [09-06-2020(online)].pdf 2020-06-09
18 201747023426-FORM 3 [09-06-2020(online)].pdf 2020-06-09
19 201747023426-OTHERS [09-09-2020(online)].pdf 2020-09-09
20 201747023426-FER_SER_REPLY [09-09-2020(online)].pdf 2020-09-09
21 201747023426-COMPLETE SPECIFICATION [09-09-2020(online)].pdf 2020-09-09
22 201747023426-CLAIMS [09-09-2020(online)].pdf 2020-09-09
23 201747023426-ABSTRACT [09-09-2020(online)].pdf 2020-09-09
24 201747023426-Response to office action [31-07-2023(online)].pdf 2023-07-31
25 201747023426-US(14)-HearingNotice-(HearingDate-30-11-2023).pdf 2023-10-27
26 201747023426-Correspondence to notify the Controller [21-11-2023(online)].pdf 2023-11-21

Search Strategy

1 Finalsearchstrategy_06-12-2019.pdf