IP Library Granted Patent US 11,634,867
Granted Patent B2
US 11,634,867 · App. 17/132,375 · Granted Apr 25, 2023

Method for producing paper

Inventors: Akihiro Oshima (Suita, JP); Yoshikage Ohmukai (Osaka, JP); Yuko Shiotani (Osaka, JP); Kazuyuki Satou (Osaka, JP); Michio Matsuda (Osaka, JP); Tomohiro Yoshida (Osaka, JP); Ikuo Yamamoto (Osaka, JP)
Assignees: OSAKA UNIVERSITY; DAIKIN INDUSTRIES, LTD.
D21H19/20D21H21/16D21H27/10
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Quick Facts
Patent No.
US 11,634,867
App. No.
17/132,375
Granted
Apr 25, 2023
Kind
B2
Abstract

A method for producing a paper, which includes applying at least one of ionizing radiation and plasma to at least one of a paper base and a compound (A) selected from: a compound having a carbon-carbon unsaturated bond and containing no fluorine atom in a molecular structure, and a compound containing no fluorine atom in a molecular structure in which radicals are generated by irradiation of an electron beam to the compound, to introduce a layer formed from the compound (A) on a surface of the paper base.

Claims (50)

1. A method for producing a paper, wherein the method comprises applying at least one of ionizing radiation and plasma to at least one of a paper base and a compound (A) selected from:

a compound having a carbon-carbon unsaturated bond and containing no fluorine atom in a molecular structure,

to introduce a layer formed from a graft polymer consisting of the compound (A) on a surface of the paper base,

wherein the compound (A) is at least one of compounds represented by the following formulae:

CH 2 =C(−R 1 )—C(═O)—O—R 2 ,

CH 2 =C(−R 1 )—C(═O)—O—(CH 2 ) m —OC(═O)—NH—R 2 ,

CH 2 =C(−R 1 )—C(═O)—O—(CH 2 ) m —NH—C(═O)—R 3 ,

CH 2 =C(−R 1 )—C(═O)—O—(CH 2 ) m —NH—C(═O)—NH—R 2 ,

CH 2 =C(−R 1 )—C(═O)—O—(CH 2 ) m —NH—SO 2 —R 2 ,

CH 2 =C(−R 1 )—C(═O)—O—R 4 —C 6 H 4 —O—R 2 ,

CH 2 =C(−R 1 )—C(═O)—O—(CH 2 CH 2 O) n —R 2

wherein:

R 1 is each independently at each occurrence a hydrogen atom, a —CH 3 group, or a chlorine atom;

R 2 is each independently at each occurrence an alkyl group having 14 to 28 carbon atoms;

R 3 is each independently at each occurrence an alkyl group having 13 to 27 carbon atoms;

R 4 is each independently at each occurrence a single bond or an alkylene group having 1 to 20 carbon atoms;

m is an integer of 1 to 28; and

n is an integer of 1 to 3.

2. The method according to claim 1 , wherein the compound (A) is present at least on the surface of the paper base.

3. The method according to claim 1 , wherein R 2 is an alkyl group having 16 to 27 carbon atoms.

4. The method according to claim 1 , wherein R 3 is an alkyl group having 15 to 26 carbon atoms.

5. The method according to claim 1 , further comprising bringing a solution containing the compound (A) and the paper base into contact with each other.

6. The method according to claim 5 , wherein the contact is provided by coating or spraying the solution containing the compound (A) on the paper base, or immersing the paper base in the solution containing the compound (A).

7. The method according to claim 5 , wherein the solution further contains a solvent.

8. The method according to claim 5 , wherein the solution contains 0.5 to 20 parts by mass of the compound (A) per 100 parts by mass of the solution.

9. The method according to claim 1 , wherein irradiation of the at least one of the ionizing radiation or the plasma is irradiation of the ionizing radiation.

10. The method according to claim 9 , wherein an absorbed dose of the ionizing radiation is 5 to 250 kGy.

11. The method according to claim 1 , wherein irradiation of at least one of the ionizing radiation or the plasma is irradiation of at least one of an α-ray, an electron beam, a γ-ray, a neutron ray, an X-ray, and plasma.

12. The method according to claim 11 , wherein irradiation of the at least one of the ionizing radiation or the plasma is irradiation of at least one of an electron beam and plasma.

13. A paper comprising a layer formed on a surface thereon, wherein the layer comprises a graft chain formed from a compound (A) selected from:

a compound having a carbon-carbon unsaturated bond and containing no fluorine atom in a molecular structure,

and the compound (A) is at least one of compounds represented by the following formulae:

CH 2 =C(−R 1 )—C(═O)—O—R 2 ,

CH 2 =C(−R 1 )—C(═O)—O—(CH 2 ) m —OC(═O)—NH—R 2 ,

CH 2 =C(−R 1 )—C(═O)—O—(CH 2 ) m —NH—C(═O)—R 3 ,

CH 2 =C(−R 1 )—C(═O)—O—(CH 2 ) m —NH—C(═O)—NH—R 2 ,

CH 2 =C(−R 1 )—C(═O)—O—(CH 2 ) m —NH—SO 2 —R 2 ,

CH 2 =C(−R 1 )—C(═O)—O—R 4 —C 6 H 4 —O—R 2 ,

CH 2 =C(−R 1 )—C(═O)—O—(CH 2 CH 2 O) n —R 2

wherein:

R 1 is each independently at each occurrence a hydrogen atom, a —CH 3 group, or a chlorine atom;

R 2 is each independently at each occurrence an alkyl group having 14 to 28 carbon atoms;

R 3 is each independently at each occurrence an alkyl group having 13 to 27 carbon atoms;

R 4 is each independently at each occurrence a single bond or an alkylene group having 1 to 20 carbon atoms;

m is an integer of 1 to 28; and

n is an integer of 1 to 3.

14. The paper according to claim 13 , wherein R 2 is an alkyl group having 16 to 27 carbon atoms.

15. The paper according to claim 13 , wherein R 3 is an alkyl group having 15 to 26 carbon atoms.

16. The paper according to claim 13 , wherein the paper is an oil-resistant paper.

17. The paper according to claim 13 , wherein the paper is a paper used for food packaging applications.

Assignments (2)
CHANGE OF ADDRESS Recorded Jan 11, 2023
From: DAIKIN INDUSTRIES LTD.
To: DAIKIN INDUSTRIES LTD.
Reel/Frame 062355/0740 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 23, 2020
From: OSHIMA, AKIHIRO; OHMUKAI, YOSHIKAGE; SHIOTANI, YUKO; SATOU, KAZUYUKI; MATSUDA, MICHIO; YOSHIDA, TOMOHIRO; YAMAMOTO, IKUO
To: OSAKA UNIVERSITY; DAIKIN INDUSTRIES, LTD.
Reel/Frame 054740/0724 →
Priority Claims (1)
JP JP2018-125353 · Jun 29, 2018 · national
Continuity (2)
Continuation PCTJP2019025890 · Jun 28, 2019
Related Publication 20210108371A1 · Apr 15, 2021