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Mixture of fluoroalkyl alcohol-unsaturated carboxylic acid derivatives, polymer of derivatives, and water repellent oil repellent agent containing polymer as active ingredient

A technology of carboxylic acid derivatives and water and oil repellents, which is applied in the field of mixtures of fluoroalkyl alcohol unsaturated carboxylic acid derivatives and water and oil repellents, and can solve the problem of insufficient water and oil repellency and low accumulation And other issues

Active Publication Date: 2010-12-22
UNIMATEC CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, compounds with a perfluoroalkyl group having 6 or less carbon atoms are said to have low bioaccumulation
[0005] Here, in Patent Document 2, the performance of the water and oil repellency of the perfluoroalkyl (meth)acrylate in the surface treatment film of the water and oil repellency treatment substrate is caused by the perfluoroalkyl group ( Orientation of the Rf group), and further, for the orientation of the Rf group, it is required that the Rf group has a melting point of microcrystals with 8 or more carbon atoms. For this reason, (meth)acrylic perfluoroalkane with 8 or more carbon atoms Alkylates have been used all the time. In addition, by using together a monomer having an isocyanate group as a crosslinking group, the performance of a water and oil repellent agent using a perfluoroalkyl (meth)acrylate having 7 or more carbon atoms becomes possible
However, if no isocyanate group-containing monomer is used, sufficient water and oil repellency cannot be exhibited

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment

[0128] Next, the present invention will be described with reference to examples.

reference example 1

[0130] (1) In an autoclave with a capacity of 1200ml equipped with a stirrer and a thermometer, add

[0131] CF 3 (CF 2 ) 3 (CH 2 CF 2 )(CF 2 CF 2 ) 2 I (99GC%)

[0132] 603g (0.99 moles) and 7g of di-tert-butyl peroxide, degas the autoclave with a vacuum pump. After heating the internal temperature to 80°C, ethylene was gradually introduced to make the internal pressure 0.5 MPa. Once the internal pressure dropped to 0.2 MPa, ethylene was introduced again so as to be 0.5 MPa, and this operation was repeated. While maintaining the internal temperature at 80 to 115°C, 41 g (1.45 mol) of ethylene was introduced over about 3 hours. Recover the contents under the condition that the internal temperature is below 50°C,

[0133] get CF 3 (CF 2 ) 3 (CH 2 CF 2 )(CF 2 CF 2 ) 2 (CH 2 CH 2 ) I (98GC%) 637g (98.8% yield).

[0134] (2) In a four-neck flask with a capacity of 300ml equipped with a condenser, a thermometer and a stirrer, add the obtained in the above (1) ...

Embodiment 1

[0152] In a four-neck flask with a capacity of 100 ml equipped with a condenser, a thermometer, and a stirrer, 30.0 g (0.06 mol) of the compound mixture (97.4 GC%) obtained in Reference Example 1 (2), 21 g of toluene, and 6 g of p-toluenesulfonic acid were added. 0.3 g of hydroquinone and 5 g (0.07 mol) of acrylic acid were added after heating the inner temperature to 100° C., and the reaction was carried out by stirring at an inner temperature of 115° C. for 4 hours. After the reaction was completed, the toluene was removed from 61 g of the obtained reaction mixture solution by cooling and an evaporator, and 42 g of the residue was washed with tap water to obtain 34 g of a pale yellow transparent liquid (86.9 GC%) of the reaction product (86.9 GC%) at room temperature (yield 84.1%).

[0153] For the reaction product, vacuum distillation was carried out under the conditions of internal pressure 0.1kPa, internal temperature 128-133°C, and tower top temperature 64-72°C to obtain ...

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PUM

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Abstract

Disclosed are (1) a mixture of fluoroalkyl alcohol-unsaturated carboxylic acid derivatives represented by the following general formula: CF3(CF2)n(CH=CF)a(CF2CF2)b(CH2CH2)cOCOCR=CH2and the following general formula : CF3(CF2)n-1(CF=CH)aCF2(CF2CF2)b(CH2CH2)cOCOCR=CH2 (wherein R represents a hydrogen atom or a methyl group; n represents an integer of 1-5; a represents an integer of 1-4; b represents an integer of 0-3; and c represents an integer of 1-3); (2) a fluorine-containing polymer containing the derivatives as polymerization units; and (3) a water repellent oil repellent agent containingthe fluorine-containing polymer as an active ingredient. The fluoroalkyl alcohol-unsaturated carboxylic acid derivatives are produced by esterifying a mixture of fluoroalkyl alcohols represented by the following general formula: CF3(CF2)n(CH=CF)a(CF2CF2)b(CH2CH2)cOH and the following general formula: CF3(CF2)n-1(CF=CH)aCF2(CF2CF2)b(CH2CH2)cOH with an acrylic acid or a methacrylic acid.

Description

technical field [0001] The present invention relates to a mixture of fluoroalkyl alcohol unsaturated carboxylic acid derivatives, their polymer, and a water and oil repellent agent containing the polymer as an active ingredient. More specifically, it relates to mixtures of fluoroalkyl alcohol unsaturated carboxylic acid derivatives having a perfluoroalkyl group having 6 or less carbon atoms, polymers thereof, and polymers containing the polymers as active ingredients, which are considered to be low in bioaccumulation water and oil repellent. Background technique [0002] Acrylic acid derivatives of perfluoroalkyl alcohols, such as CF 3 (CF 2 ) 7 CH 2 CH 2 OCOCH=CH 2 , It is widely used as a synthetic monomer for fluorine-containing copolymers for forming water and oil repellent agents for fibers. In addition, perfluoroalkyl alcohols, which are precursors of the acrylated products, are also widely used as surfactants and the like. Thus, acrylic acid derivatives having...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C69/653C07C67/08C07C69/007C09K3/18C07B61/00
CPCD06M2200/11C08F20/22C09K3/18D06M15/277C07C67/08D06M2200/12C07C69/653D06M15/263
Inventor 村田清一郎堀内雅可佐藤胜之栗原智
Owner UNIMATEC CO LTD