IP Library › Granted Patent US 12,503,612
Granted Patent B2
US 12,503,612 · App. 17/801,869 · Granted Dec 23, 2025

Fluorine-containing alcohol composite

Inventors: Tetsushi Kijima (Ibaraki, JP); Yasuhiko Akatsu (Ibaraki, JP); Hideo Sawada (Aomori, JP)
Assignees: UNIMATEC CO., LTD.; HIROSAKI UNIVERSITY
C09D7/65C09D5/00C09D7/61C09D129/04
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Quick Facts
Patent No.
US 12,503,612
App. No.
17/801,869
Granted
Dec 23, 2025
Kind
B2
Abstract

A fluorine-containing alcohol composite comprising a condensate of a fluorine-containing alcohol represented by the general formula: HO-A-R F -A-OH [I] (wherein R F is a group containing a perfluoroalkylene group or a polyfluoroalkylene group having 6 or less carbon atoms and an ether bond, and A is an alkylene group having 1 to 3 carbon atoms), a hydroxyl group-containing polymer, and a zirconium compound. The fluorine-containing alcohol composite, using a fluorine-containing alcohol, does not produce perfluorooctanoic acid and the like when released into the environment and that has a unit easily decomposed into short chain compounds. And also, it exhibits hydrophilic oil repellency.

Claims (22)

1 . A fluorine-containing alcohol composite comprising a condensate of:

a fluorine-containing alcohol represented by the general formula:

HO-A-R F -A-OH  [I]

wherein R F is a group containing a perfluoroalkylene group or a polyfluoroalkylene group having 6 or less carbon atoms, and an ether bond, and A is an alkylene group having 1 to 3 carbon atoms,

a hydroxyl group-containing polymer, and

a zirconium compound; wherein

the fluorine-containing alcohol, the hydroxyl group-containing polymer, and the zirconium compound are subjected to a condensation reaction in the presence of a basic or acidic catalyst to form the fluorine-containing alcohol composite.

2 . The fluorine-containing alcohol composite according to claim 1 , wherein organic silicon compound is further comprised.

3 . The fluorine-containing alcohol composite according to claim 1 , wherein as the fluorine-containing alcohol represented by the general formula [I], a perfluoroalkylene ether diols represented by the general formula:

HO(CH 2 ) a CF(CF 3 )[OCF 2 CF(CF 3 )] b O(CF 2 ) c O[CF(CF 3 )CF 2 O] d CF(CF 3 )(CH 2 ) a OH  [III]

wherein a is an integer of 1 to 3, b+d is an integer of 0 to 50, and c is an integer of 1 to 6 is used.

4 . The fluorine-containing alcohol composite according to claim 1 , wherein the hydroxyl group-containing polymer is polyvinyl alcohol.

5 . The fluorine-containing alcohol composite according to claim 1 , wherein the zirconium compound is zirconium oxychloride.

6 . The fluorine-containing alcohol composite according to claim 2 ,

wherein the organic silicon compound is tetra lower alkyl orthosilicate.

7 . The method for producing a condensate according to claim 1 , wherein the hydroxyl group-containing polymer is used at a 0.5 to 10 times ratio, and the zirconium compound is used at a 5 times or less ratio, based on the fluorine-containing alcohol.

8 . The method for producing a condensate according to claim 1 , wherein the organic silicon compound is used at a 5 times or less ratio, based on the fluorine-containing alcohol.

9 . The method for producing a condensate according to claim 1 , wherein the basic catalyst is an ammonia aqueous solution.

10 . The method for producing a condensate according to claim 1 , wherein the acidic catalyst is an inorganic acid.

11 . A surface treatment agent, comprising the fluorine-containing alcohol composite according to claim 1 , as an active ingredient.

12 . The surface treatment agent according to claim 11 , which exhibits hydrophilic oil repellency.

13 . A substrate with a coating film formed from the surface treatment agent according to claim 11 .

Assignments (3)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 24, 2022
From: KIJIMA, TETSUSHI; AKATSU, YASUHIKO; SAWADA, HIDEO
To: UNIMATEC CO., LTD.; HIROSAKI UNIVERSITY
Reel/Frame 060884/0917 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 24, 2022
From: KIJIMA, TETSUSHI; AKATSU, YASUHIKO
To: UNIMATEC CO., LTD.
Reel/Frame 060887/0842 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 24, 2022
From: SAWADA, HIDEO
To: HIROSAKI UNIVERSITY
Reel/Frame 060887/0874 →
Priority Claims (1)
JP 2020-031493 · Feb 27, 2020 · national
Continuity (1)
Related Publication 20230093691A1 · Mar 23, 2023
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