IP Library Granted Patent US 12692659
Granted Patent B2
US 12692659 · App. 18/134,126 · Granted Jul 28, 2026

Oil-resistant agent and oil-resistant composition

Inventors: Michio Matsuda (Osaka, JP); Hirotoshi Sakashita (Osaka, JP); Nozomi Yamaguchi (Osaka, JP); Tetsuya Uehara (Osaka, JP); Daisuke Noguchi (Osaka, JP); Shun Shibata (Osaka, JP)
Assignee: DAIKIN INDUSTRIES, LTD.
D21H21/16C09D5/00C09D103/02C09D103/06C09D103/10D21H19/12
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Quick Facts
Patent No.
US 12692659
App. No.
18/134,126
Granted
Jul 28, 2026
Kind
B2
Abstract

An oil-resistant agent and an oil-resistant composition, which are capable of imparting excellent oil-resistance to paper. The oil-resistant composition contains a polysaccharide (1) and an oil-resistant polymer (2). The polysaccharide (1) is preferably starch. The oil-resistant polymer (2) preferably has (a) a repeating unit formed from an acrylic monomer that has a long-chain hydrocarbon group having 7-40 carbon atoms, and (b) a repeating unit formed from an acrylic monomer that has a hydrophilic group. A polyvinyl alcohol or glucose may be present as an additive.

Claims (82)

1 . An oil-resistant composition comprising

(1) at least one polysaccharide selected from the group consisting of hydrophobized modified starch having a hydrophobic group that is a hydrocarbon having 3 to 40 carbon atoms, oxidized starch, dextrin, and pregelatinized starch; and

(2) an oil-resistant polymer that is a non-fluorine copolymer having:

(a) a repeating unit formed from an acrylic monomer having a long-chain hydrocarbon group having 7 to 40 carbon atoms, and

(b) a repeating unit formed from an acrylic monomer having a hydrophilic group,

wherein a weight average molecular weight of the non-fluorine copolymer is 900,000 to 10,000,000.

2 . The oil-resistant composition according to claim 1 , wherein a weight ratio of the polysaccharide (1) to the oil-resistant polymer (2) is 10:90 to 98:2.

3 . The oil-resistant composition according to claim 1 , wherein the acrylic monomer having a long-chain hydrocarbon group (a) is a monomer represented by formula:

CH 2 ═C(—X 1 )—C(═O)—Y 1 (R 1 ) k

wherein

R 1 is each independently a hydrocarbon group having 7 to 40 carbon atoms,

X 1 is a hydrogen atom, a monovalent organic group, or a halogen atom,

Y 1 is a divalent to tetravalent group composed of at least one selected from a hydrocarbon group having one carbon atom, —C 6 H 4 —, —O—, —C(═O)—, —S(═O) 2 —, or —NH—, provided that a hydrocarbon group is excluded, and

k is 1 to 3.

4 . The oil-resistant composition according to claim 1 , wherein the acrylic monomer having a long-chain hydrocarbon group (a) is:

(a1) an acrylic monomer represented by formula:

CH 2 ═C(—X 2 )—C(═O)—Y 2 —R 2

wherein

R 2 is a hydrocarbon group having 7 to 40 carbon atoms,

X 2 is a hydrogen atom, a monovalent organic group, or a halogen atom, and

Y 2 is —O— or —NH—, and/or

(a2) an acrylic monomer represented by formula:

CH 2 ═C(—X 3 )—C(═O)—Y 3 —Z(—Y 4 —R 3 ) n

wherein

R 3 is each independently a hydrocarbon group having 7 to 40 carbon atoms,

X 3 is a hydrogen atom, a monovalent organic group, or a halogen atom,

Y 3 is —O— or —NH—,

Y 4 is each independently a group composed of at least one selected from a direct bond, —O—, —C(═O)—, —S(═O) 2 —, —NH—, or —CH 2 —,

Z is a direct bond or a divalent or trivalent hydrocarbon group having 1 to 5 carbon atoms, and

n is 1 or 2; and

the acrylic monomer having a hydrophilic group (b) is an oxyalkylene (meth)acrylate represented by formula:

CH 2 ═CX 11 C(═O)—Y 11 —(RO) n -A

wherein

X 11 is a hydrogen atom or a methyl group,

Y 11 is —O— or —NH—,

R is an alkylene group having 2 to 6 carbon atoms,

A is a hydrogen atom, an unsaturated or saturated hydrocarbon group having 1 to 22 carbon atoms, or CH 2 ═CX 11 C(═O)—, wherein X 11 is a hydrogen atom or a methyl group, and

n is an integer of 1 to 90.

5 . The oil-resistant composition according to claim 1 , wherein the long-chain hydrocarbon group has 12 to 30 carbon atoms.

6 . A treatment liquid formed from the oil-resistant composition according to claim 1 and water, and having a viscosity of 200 cps or lower.

7 . An oil-resistant paper having an oil-resistant layer formed from the oil-resistant composition according to claim 1 on a surface of the paper.

8 . A paper treating method comprising treating paper with the oil-resistant composition according to claim 1 by an external treatment or an internal treatment.

9 . The oil-resistant composition according to claim 1 , wherein

a weight ratio of the polysaccharide (1) to the oil-resistant polymer (2) is 80:20 to 93:7.

10 . The oil-resistant composition according to claim 9 , wherein the acrylic monomer having a long-chain hydrocarbon group (a) is:

(a1) an acrylic monomer represented by formula:

CH 2 ═C(—X 2 )—C(—O)—Y 2 —R 2

wherein

R 2 is a hydrocarbon group having 7 to 40 carbon atoms,

X 2 is a hydrogen atom, a monovalent organic group, or a halogen atom, and

Y 2 is —O— or —NH—, and/or

(a2) an acrylic monomer represented by formula:

CH 2 ═C(—X 3 )—C(═O)—Y 3 —Z(—Y 4 —R 3 ) n

wherein

R 3 is each independently a hydrocarbon group having 7 to 40 carbon atoms,

X 3 is a hydrogen atom, a monovalent organic group, or a halogen atom,

Y 3 is —O— or —NH—,

Y 4 is each independently a group composed of at least one selected from a direct bond, —O—, —C(═O)—, —S(═O) 2 —, —NH—, or —CH 2 —,

Z is a direct bond or a divalent or trivalent hydrocarbon group having 1 to 5 carbon atoms, and

n is 1 or 2; and

the acrylic monomer having a hydrophilic group (b) is an oxyalkylene (meth)acrylate represented by formula:

CH 2 ═CX 11 C(═O)—Y 11 —(RO) n -A

wherein

X 11 is a hydrogen atom or a methyl group,

Y 11 is —O— or —NH—,

R is an alkylene group having 2 to 6 carbon atoms,

A is a hydrogen atom, an unsaturated or saturated hydrocarbon group having 1 to 22 carbon atoms, or CH 2 ═CX 11 C(═O)—, wherein X 11 is a hydrogen atom or a methyl group, and

n is an integer of 1 to 90.

11 . The oil-resistant composition according to claim 9 , wherein the long-chain hydrocarbon group has 12 to 30 carbon atoms.

12 . A treatment liquid formed from the oil-resistant composition according to claim 9 and water, and having a viscosity of 200 cps or lower.

13 . An oil-resistant paper having an oil-resistant layer formed from the oil-resistant composition according to claim 9 on a surface of the paper.

14 . A paper treating method comprising treating paper with the oil-resistant composition according to claim 9 by an external treatment or an internal treatment.

15 . The oil-resistant composition according to claim 1 , which is configured for use in an external treatment for paper,

wherein the oil-resistant composition comprises a combination of two or more of starch that is

(i) a combination of two or more of a hydrophobized modified starch, or

(ii) a combination of a hydrophobized modified starch and other starch

wherein the hydrophobized modified starch has a hydrophobic group that is a hydrocarbon having 3 to 40 carbon atoms,

wherein the other starch is selected from the group consisting of hydroxyalkylated starch, oxidized starch, dextrin, cationized starch, pregelatinized starch and etherified starch.

16 . The paper oil-resistant composition according to claim 15 , wherein the combination of two or more of starch is a combination of alkenylsuccinated starch and at least one of starch selected from the group consisting of hydroxyalkylated starch, oxidized starch, dextrin, cationized starch, pregelatinized starch, and etherified starch.

17 . A treatment liquid formed from the oil-resistant composition according to claim 15 and water, and having a viscosity of 200 cps or lower.

18 . The oil-resistant paper having an oil-resistant layer formed from the oil-resistant composition according to claim 15 on a surface of the paper.

19 . A paper treating method comprising treating paper with the oil-resistant composition according to claim 15 on a surface of the paper by an external treatment or an internal treatment.