Fluorine-containing copolymer having excellent washing resistance and soil release agent

A technology of copolymer and detergent, which is applied in the direction of textiles and papermaking, chemical instruments and methods, and liquid-repellent fibers, etc., can solve the problems of oil repellency, anti-fouling and low durability of stain-removing washing, etc. Achieve outstanding effect, excellent detergency, and excellent washing durability

Active Publication Date: 2009-12-02
DAIKIN IND LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] However, the fluoropolymers disclosed in JP 2004-526042, U.S. Patent No. 6,326,447, and WO2005 / 090423 have disadvantages of low washing durability in oil repellency, stain resistance, and stain release.

Method used

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  • Fluorine-containing copolymer having excellent washing resistance and soil release agent
  • Fluorine-containing copolymer having excellent washing resistance and soil release agent

Examples

Experimental program
Comparison scheme
Effect test

Embodiment

[0202] Hereinafter, the present invention will be described in detail with reference to Examples, Comparative Examples, and Test Examples. However, these descriptions do not limit the invention.

[0203] Hereinafter, unless otherwise specified, parts or % represent parts by weight or % by weight.

[0204] The test was carried out as follows.

[0205] Decontamination test

[0206] The decontamination test is based on the American AATCC Stain Release Management Performance Test Method. The test soils used corn oil, mineral oil or artificial oil. The artificial oil was prepared by adding 100 ml of Daphne Mechanic Oil (manufactured by Idemitsu Kosan) to 1 g of diamond paste consisting of 16.7% of carbon black, 20.8% of tallow extremely hardened oil, and 62.5% of liquid paraffin.

[0207]On the blotting paper laid out in the horizontal direction, a test cloth with a side length of 20 cm was spread out, and 5 drops (about 0.2 cc) of artificial oil as stains were dropped on the t...

Synthetic example 1

[0214] Synthesis example 1 (9FSO2PA monomer)

[0215] Synthesis of 3-(perfluorobutylsulfonyl)propyl acrylate

[0216]

[0217] Under the condition that a calcium chloride tube is installed, 54.4g (159mmol) of 3-(perfluorobutylsulfonyl) propanol, 33ml (238mmol) of triethylamine, 4-tert-butylcatechol (0.14g), A solution of 520 ml of dichloromethane was cooled to 0°C, and 15.5 ml (191 mmol) of acryloyl chloride was slowly added dropwise over 40 minutes. After stirring at room temperature for 1 hour, the mixture was washed with 600 ml of 15% citric acid water and saturated brine, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure to obtain a crude acrylate. The residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=6:1), and the concentrated clear liquid was vacuum-dried to obtain 3-(perfluorobutylsulfonyl)propyl acrylate 60.0g. The yield was 95.3%.

[0218] 1 H NMR (CDCl 3 , internal standard TMSδppm): 6.45...

Embodiment 1

[0222] In a 100ml four-necked flask, 14g of 2-(perfluorohexyl)ethyl acrylate (13FA), 4.4g of polyethylene glycol monoacrylate (EO 10mol) (AE-400), 2-hydroxyethyl acrylate 0.6 g of ester (HEA), 0.4 g of dimethylaminoethyl methacrylate (DMAEM), 0.6 g of (acetoacetoxyethyl) methacrylate (AAEM) and 30 g of isopropanol were blown with nitrogen for 60 minutes. After raising internal temperature to 75-80 degreeC, 0.12g of azobisisobutyronitrile was added, and it was made to react for 8 hours. The molecular weight of the obtained polymerization solution was directly measured by gel permeation chromatography, and it was confirmed that the peak derived from the monomer almost disappeared and the peak derived from the copolymer appeared. In addition, the weight average molecular weight of a copolymer was 16000 (polystyrene conversion). Finally, 0.153 g of acetic acid was added for neutralization, and diluted with water to obtain a 20% solution of the fluorinated copolymer.

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Abstract

Disclosed is a soil release agent composition essentially containing a fluorine-containing copolymer, which is essentially composed of (a) a fluorine-containing monomer having a fluoroalkyl group, (b) a polyalkyleneglycol(meth)acrylate, (c) a monomer having an acetoacetyl group and (d) a monomer having a cation-donating group, and a crosslinking agent. This soil release agent composition imparts a base material such as a fiber fabric with excellent oil repellency, antifouling property and soil releasing property, while maintaining washing resistance of the base material. The monomer (a) is preferably represented by the following formula: CH2=C(-X)-C(=O)-Y-Z-Rf (1). In the formula, X represents a hydrogen atom, a linear or branched alkyl group having 1-21 carbon atoms, a fluorine atom, a chlorine atom or the like; Y represents -O- or -NH-; Z represents an aliphatic group having 1-10 carbon atoms, an aromatic group having 6-18 carbon atoms, an alicyclic group or the like; and Rf represents a linear or branched fluoroalkyl group having 1-21 carbon atoms.

Description

technical field [0001] The present invention relates to a fluorine-containing copolymer that imparts excellent oil repellency, stain repellency, and stain releasability to articles to be treated such as fiber products, and is excellent in washing durability of the oil repellency, stain repellency, and stain releasability, and a composition thereof. Background technique [0002] As an antifouling finishing agent that can impart water and oil repellency to fiber fabrics and the like, and can easily remove dirt adhering to fibers by washing or the like, (meth)acrylates having a fluoroalkyl group (hereinafter, also referred to as Fluorine-containing copolymer (called fluorine-containing compound) and a compound containing a hydrophilic group (refer to Japanese Patent Application No. 53-134786, Japanese Patent Application No. 59-204980, and Japanese Patent Application No. 62-7782) . [0003] However, fiber fabrics and the like treated with these fluorine-containing copolymers ma...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08F220/22C08F220/26C09K3/18D06M15/277
CPCD06M2200/11D06M15/295D06M15/277D06M2200/12D06M15/27C08F220/22C08F220/26C09K3/18
Inventor 上杉宪正
Owner DAIKIN IND LTD
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