Graft copolymer and soil resistant composition

Patent metadata

Field	Value
Publication number	US-11566095-B2
Application number	US-202017085544-A
Country	US
Kind code	B2
Filing date	Oct 30, 2020
Priority date	Oct 31, 2019
Publication date	Jan 31, 2023
Grant date	Jan 31, 2023

Abstract

Provided is a graft copolymer and a treatment method which give excellent antifouling property to a substrate, especially a carpet. The graft copolymer has a trunk polymer having a hydroxyl group; and a branch having a C 7-40 hydrocarbon group bonded to the trunk polymer at a carbon atom substituted with the hydroxyl group, wherein the branch has a repeating unit formed from an acrylic monomer represented by the formula: CH 2 ═C(—X)—C(═O)—Y 1 —Z(—Y 2 —R) n . The treatment method include applying the graft copolymer to the substrate.

First claim

The invention claimed is:

1. A graft copolymer comprising:
a trunk polymer having a hydroxyl group; and
a branch having a C 7-40 hydrocarbon group and bonded to the trunk polymer at a carbon atom substituted with the hydroxyl group,
wherein the branch comprises a repeating unit formed from an acrylic monomer represented by the formula:
CH 2 ═C(—X)—C(═O)—Y 1 —Z(—Y 2 —R) n

wherein R each is independently a hydrocarbon group having 7 to 40 carbon atoms,
X is a hydrogen atom, a monovalent organic group or a halogen atom,
Y 1 is —O— or —NH—,
Y 2 each is independently a direct bond, or a group comprising at least one selected from, —O—, —C(═O)—, —S(═O) 2 — and —NH—, and
Z is a direct bond, or a divalent or trivalent group having 1 to 5 carbon atoms, and
n is 1 or 2.

2. The graft copolymer according to claim 1 , wherein the trunk polymer is a water-soluble polymer, and comprises a homopolymer of vinyl alcohol or a copolymer of vinyl alcohol and vinyl acetate.

3. The graft copolymer according to claim 1 , wherein the trunk polymer has the number-average molecular weight of 3,000 to 100,000.

4. The graft copolymer according to claim 1 , wherein, in the acrylic monomer forming the branch, Y 2 is —Y′—, —Y′—Y′—, —Y′—C(═O)—, —C(═O)—Y′—, —Y′—C(═O)—Y′—, —Y′—R′—, —Y′—R′—Y′—, —Y′—R′—Y′—C(═O)—, —Y′—R′—C(═O)—Y′—, —Y′—R′—Y′—C(═O)—Y′— or —Y′—R′—Y′—R′—,
wherein Y′ is independently a direct bond, —O— or —NH—,
R′ is —(CH 2 ) m — (m is an integer of 1 to 5), a linear hydrocarbon group having an unsaturated bond and 1 to 5 carbon atoms, a hydrocarbon group having a branched structure and having 1 to 5 carbon atoms, or —(CH 2 ) l —C 6 H 4 —(CH 2 ) l — (l is an integer from 0 to 5 independently and —C 6 H 4 — is a phenylene group).

5. The graft copolymer according to claim 1 , wherein the acrylic monomer forming the branch is represented by the formula:
CH 2 ═C(—X)—C(═O)—O—(CH 2 ) m —NH—C(═O)—R,

CH 2 ═C(—X)—C(═O)—O—(CH 2 ) m —O—C(═O)—NH—R,

CH 2 ═C(—X)—C(═O)—O—(CH 2 ) m —NH—C(═O)—O—R, or

CH 2 ═C(—X)—C(═O)—O—(CH 2 ) m —NH—C(═O)—NH—R,

wherein R each is independently a hydrocarbon group having 7 to 40 carbon atoms,
X is a hydrogen atom, a monovalent organic group or a halogen atom,
m is an integer of 1 to 5.

6. The graft copolymer according to claim 1 , wherein, in the acrylic monomer forming the branch, the hydrocarbon group has 18 to 40 carbon atoms.

7. The graft copolymer according to claim 1 , wherein the branch further comprises a repeating unit formed from a fluorine-free vinyl monomer.

8. The graft copolymer according to claim 7 , wherein the fluorine-free vinyl monomer is a monomer wherein a homopolymer of the monomer has a glass transition point or melting point of 80° C. or higher.

9. The graft copolymer according to claim 7 , wherein the fluorine-free vinyl monomer is a compound represented by the formula:
CH 2 ═CA-T

wherein A is a hydrogen atom, a methyl group, a chlorine atom, a bromine atom or an iodine atom,
T is a hydrogen atom, a chain or cyclic hydrocarbon group having 1 to 40 carbon atoms, or a chain or cyclic organic group having 1 to 41 carbon atoms and having an ester bond.

10. The graft copolymer according to claim 1 , wherein a weight ratio of the trunk polymer to the branch is from 10/90 to 90/10.

11. The graft copolymer according to claim 1 , which is a fluorine-free copolymer.

12. A soil resistant composition, comprising:
an aqueous continuous phase which is water or a mixture of water and an organic solvent; and
the graft copolymer according to claim 1 , dispersed in the aqueous continuous phase.

13. A method of treating a substrate, comprising applying the soil resistant composition according to claim 12 to the substrate, and drying the substrate to impart soil resistance to the substrate.

14. A treated substrate which comprises the graft copolymer according to claim 1 adhered to the substrate.

15. The treated substrate according to claim 14 , wherein the substrate is a carpet.

Assignees

• Daikin Ind Ltd

Inventors

• Nakamura Hisako

Classifications

• C09D151/003

  grafted on to macromolecular compounds obtained by reactions only involving unsaturated carbon-to-carbon bonds (C09D151/04, C09D151/06 take precedence) · CPC title

• C08F263/04 Primary

  on to polymers of vinyl acetate · CPC title

• C08F261/04 Primary

  on to polymers of vinyl alcohol · CPC title

• C09D5/1637

  Macromolecular compounds · CPC title