IP Library Patent Application 18076613
Patent Application
App. No. 18/076,613

FLUORINE-CONTAINING COMPOUND

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Patent No.
US None
App. No.
18/076,613
Abstract

A fluorine-containing compound represented by general formula (1) by which high water-repellency can be obtained despite the small number of fluorine atoms: L-(R 1 —X—Rf—Y—R 2 ) n   (1) wherein L represents an n-valent organic group; n represents an integer of 1 or more; Rf represents a linear or branched fluoroalkylene group containing 1 to 4 of at least any of a CF 2 unit, a CFH unit and a CFRf′ unit, and optionally having an ether bond, wherein Rf′ represents a fluoroalkyl group having 1 carbon atom; R 1 represents a direct bond, or a linear or branched hydrocarbon group having 1 to 4 carbon atoms; R 2 represents a linear or branched hydrocarbon group having 7 to 29 carbon atoms, containing no fluorine atoms, and optionally having an ether bond; and X and Y each independently represent a direct bond or a divalent linking group.

Claims (49)

1 . A compound represented by a general formula (1):

L-(R 1 —X—Rf—Y—R 2 ) n   (1)

wherein L is represented by a general formula (L-1):

CH 2 ═CA-Z—*  (L-1)

wherein A represents a hydrogen atom, a hydrocarbon group having 1 to 4 carbon atoms, a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom,

Z represents a divalent linking group, and

symbol * represents a bonding hand of L; or

L is a carbon-containing linker moiety prepared by a process including reacting

(a) at least one isocyanate group-containing compound selected from the group consisting of isocyanate, diisocyanate and polyisocyanate, and

(b) at least one isocyanate reactive compound selected from the group consisting of compounds represented by general formulae (2a), (2b) and (2c):

wherein, in the general formulae (2a) and (2c),

each R independently represents —H, -*, —C(O)—*, —(CH 2 CH 2 O) p (CH(CH 3 )CH 2 O) q H, —(CH 2 CH 2 O) p (CH(CH 3 )CH 2 O) q —*, or —(CH 2 CH 2 O) p (CH(CH 3 )CH 2 O) q C(O)—*,

each p independently represents 0 to 20,

each q independently represents 0 to 20,

p+q is larger than 0,

symbol * represents a bonding hand of L, and

at least one R represents —H or —(CH 2 CH 2 O) p (CH(CH 3 )CH 2 O) q H, and at least another one R represents -*, —C(O)—*, —(CH 2 CH 2 O) p (CH(CH 3 )CH 2 O) q —*, or —(CH 2 CH 2 O) p (CH(CH 3 )CH 2 O) q C(O)—*, with the proviso that the isocyanate reactive compound is represented by the general formula (2a) or (2c); and

wherein, in the general formula (2b),

each R′ independently represents —H, -*, —C(O)—*, —(CH 2 CH 2 O) p′ (CH(CH 3 )CH 2 O) q′ H, —(CH 2 CH 2 O) p′ (CH(CH 3 )CH 2 O) q —*, or —(CH 2 CH 2 O) p′ (CH(CH 3 )CH 2 O) q′ C(O)—*,

each R″ independently represents —H, -*, —(CH 2 CH 2 O) p′ (CH(CH 3 )CH 2 O) q′ H, —(CH 2 CH 2 O) p′ (CH(CH 3 )CH 2 O) q —*, or —(CH 2 CH 2 O) p′ (CH(CH 3 )CH 2 O) q′ C(O)—*,

each p′ independently represents 0 to 20,

each q′ independently represents 0 to 20,

p′+q′ is larger than 0,

symbol * is a bonding hand of L, and

at least one selected from R′ and R″ represents —H or —(CH 2 CH 2 O) p′ (CH(CH 3 )CH 2 O) q′ H, and at least another one selected from R′ and R″ represents -*, —C(O)—*, —(CH 2 CH 2 O) p′ (CH(CH 3 )CH 2 O) q′ —*, or —(CH 2 CH 2 O) p′ (CH(CH 3 )CH 2 O) q′ C(O)—*, with the proviso that the isocyanate reactive compound is represented by the general formula (2b); and

n represents an integer of 1 or more,

Rf represents a linear or branched fluoroalkylene group containing 1 to 4 of at least any of a CF 2 unit, a CFH unit and a CFRf′ unit, and optionally having an ether bond, wherein Rf′ represents a fluoroalkyl group having 1 carbon atom,

R 1 represents a linear or branched hydrocarbon group having 1 to 4 carbon atoms,

R 2 represents a linear or branched hydrocarbon group having 7 to 29 carbon atoms, containing no fluorine atoms, and optionally having an ether bond, and

X and Y each independently represent a direct bond or a divalent linking group.

2 . The compound according to claim 1 , wherein in the general formula (1), X and Y represent direct bonds, and Rf is a linear or branched fluoroalkylene group containing 1 to 2 of at least any of a CF 2 unit, a CFH unit and a CFRf′ unit.

3 . The compound according to claim 1 , wherein in the general formula (1), X and Y each independently represent a divalent linking group selected from the group consisting of —SO 2 —, —SO 2 NR 3 —, —NR 3 SO 2 —, —O—, —C(═O)—O—, —O—C(═O)—, —C(═O)—N(—R 3 )—, —N(—R 3 )—C(═O)—, —N(—R 3 )—C(═O)—N(—R 3 )—, —O—C(═O)—N(—R 3 )—, —N(—R 3 )—C(═O)O—, and —C 6 H 4 —, wherein R 3 represents a hydrogen atom or a hydrocarbon group having 1 to 4 carbon atoms.

4 . The compound according to claim 1 , wherein said L is represented by the general formula (L-1), and in the general formula (L-1), Z represents a divalent linking group selected from the group consisting of —C(═O)O—* and —C(═O)NR 3 —* wherein R 3 represents a hydrogen atom, or a hydrocarbon group having 1 to 4 carbon atoms.

5 . The compound according to claim 1 , wherein said L is the carbon-containing linker moiety, and the diisocyanate and the polyisocyanate are at least one selected from the group consisting of hexamethylene diisocyanate homopolymer, 3-isocyanatemethyl-3,4,4-trimethylcyclohexyl isocyanate, bis-(4-isocyanatocyclohexyl)methane, and compounds represented by general formulae (3a), (3b), (3c) and (3d).

6 . A polymer, comprising a repeating unit derived from the compound according to claim 1 , with the proviso that said L is represented by the general formula (L-1).

7 . An article having a surface formed of a material comprising the compound according to claim 1 .

8 . A composition, comprising:

the compound according to claim 1 ; and

a liquid medium.

9 . The composition according to claim 8 , wherein the liquid medium is water or a mixture of water and an organic solvent.

10 . The composition according to claim 8 , which is a water repellent.

11 . A textile product, which is processed with the composition according to claim 8 .

12 . An article having a surface formed of a material comprising the polymer according to claim 6 .

13 . A composition, comprising:

the polymer according to claim 6 ; and

a liquid medium.

14 . The composition according to claim 13 , wherein the liquid medium is water or a mixture of water and an organic solvent.

15 . The composition according to claim 13 , which is a water repellent.

16 . A textile product, which is processed with the polymer according to claim 13 .

Assignments (2)
CHANGE OF ADDRESS Recorded Jan 11, 2023
From: DAIKIN INDUSTRIES LTD.
To: DAIKIN INDUSTRIES LTD.
Reel/Frame 062355/0697 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 7, 2022
From: INAMASU, RENA; HIGASHI, MASAHIRO; YAMAMOTO, IKUO; YOSHIDA, TOMOHIRO; TAKAKUWA, TATSUYA; MATUBAYASI, NOBUYUKI; KOJIMA, HIDEKAZU
To: DAIKIN INDUSTRIES, LTD.
Reel/Frame 062011/0943 →