# US 6,293,972 B1 · Process for fluorinating cellulosic materials and fluorinated cellulosic materials

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- Number: US 6,293,972 B1
- Document ID: US6293972B1
- Status: Granted
- Kind: B1
- Application number: 09/155,436
- Filed: 1998-09-29
- Granted: 2001-09-25
- Earliest claimed: 1996-03-29
- Assignees: Daikin Industries, Ltd.
- Inventors: Fumihiko Yamaguchi; Eiji Sakamoto
- Web page: https://patentgrep.com/patent/US6293972B1

## CPC

- C08H 8/00: Macromolecular compounds derived from lignocellulosic materials {(pretreatment thereof B27N)}
- C08B 15/00: Preparation of other cellulose derivatives or modified cellulose {, e.g. complexes}
- D06M 14/04: of vegetal origin, e.g. cellulose or derivatives thereof
- D06M 15/256: containing fluorine
- D06M 15/277: containing fluorine
- D06M 23/10: Processes in which the treating agent is dissolved or dispersed in organic solvents; Processes for the recovery of organic solvents thereof
- D21C 9/005: {organic compounds}
- D06M 2101/06: cellulosic
- D06M 2200/10: Repellency against liquids
- D06M 2200/11: Oleophobic properties
- D06M 2200/12: Hydrophobic properties
- D06M 2200/45: Shrinking resistance, anti-felting properties
- C08H: DERIVATIVES OF NATURAL MACROMOLECULAR COMPOUNDS (polysaccharides C08B; natural rubber C08C; natural resins or their derivatives C09F; bituminous materials C10)
- C08B: POLYSACCHARIDES; DERIVATIVES THEREOF (polysaccharides containing less than six saccharide radicals attached to each other by glycosidic linkages C07H; fermentation or enzyme-using processes C12P19/00; sugar industry C13; production of cellulose D21)
- D06M: TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D21C: PRODUCTION OF CELLULOSE BY REMOVING NON-CELLULOSE SUBSTANCES FROM CELLULOSE-CONTAINING MATERIALS; REGENERATION OF PULPING LIQUORS; APPARATUS THEREFOR

## Abstract

In the fluorinated cellulosic material obtained by a method for fluorinating a cellulosic material by reacting a cellulosic material selected from the group consisting of cellulose material and lignocellulose material with at least one fluorine-containing compound selected from the group consisting of fluorine-containing olefin compound, fluorine-containing acrylate compound and fluorine-containing methacrylate compound in an organic solvent in the presence of a catalyst, not only the surface but also the inside of the cellulose and/or lignocellulose materials are modified and high performance of the cellulose and/or lignocellulose materials is realized.

## Claims

### Claim 1

A method for fluorinating a cellulosic material, which comprises reacting a cellulosic material selected from the group consisting of a cellulosic material and a lignocellulose material with at least one fluorine-containing compound selected from the group consisting of a fluorine-containing olefin compound, a fluorine-containing acrylate compound and a fluorine-containing methacrylate compound in an aprotic polar organic solvent in the presence of a catalyst.

### Claim 2 (depends on 1)

The method according to claim 1, wherein the cellulosic material is a cellulose material selected from the group consisting of natural cellulose and regenerated cellulose.

### Claim 3 (depends on 1)

The method according to claim 1, wherein the cellulosic material is a lignocellulose material selected from the group consisting of wood, pulp and paper.

### Claim 4 (depends on 1)

The method according to claim 1, wherein the catalyst is a basic catalyst.

### Claim 5 (depends on 1)

The method according to claim 1, wherein the catalyst is a fluoride salt of an alkali metal or alkaline earth metal.

### Claim 6 (depends on 1)

The method according to claim 1, wherein the catalyst is potassium fluoride.

### Claim 7 (depends on 1)

The method according to claim 1, wherein the fluorine-containing olefin compound is RfCF═CF2, RfCF═CClF, RfCF═CH2, RfCH═CH2, Rf2C═CF2 or Rf2C═CH2, the fluorine-containing acrylate compound is RfOCOCH═CH2, and the fluorine-containing methacrylate compound is RfOCOC(CH3)═CH2 wherein Rf is F, Cl, a C1-30 polyfluoroalkyl group, a C1-30 polyfluoroalkenyl group, a C1-30 polyfluoroalkoxy group, or a C2-300 polyfluoropolyether group.

### Claim 8 (depends on 1)

The method according to claim 1, wherein the fluorine-containing olefin compound is Rf′[CF═CF2]n, Rf′[CF═CClF]n, Rf′[CF═CH2]n, Rf′[CH═CH2]n, Rf′[CF═CF2]n, Rf′[CF═CClF]n or Rf′[CF═CH2]n, the fluorine-containing acrylate compound is Rf′[OCOCH═CH2]n, and the fluorine-containing methacrylate compound is Rf′[OCOC(CH3)═CH2]n wherein n is an integer of 2 to 4; and Rf′ is a C1-30 organic polyfluoro group or a C2-300 polyfluoropolyether group.