Side chain fluorochemicals with crystallizable spacer groups

A compound and group technology, applied in the field of fluorine-containing compounds, to achieve the effect of easy processing and handling

Inactive Publication Date: 2013-08-21
3M INNOVATIVE PROPERTIES CO
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, in the synthesis of traditional fluorinated polymers, the length of the perfluoroalkyl chain is the only part of the side chains selected to enhance the formation of crystalline domains, and the alignment of the side chains is believed to result in close packing

Method used

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  • Side chain fluorochemicals with crystallizable spacer groups
  • Side chain fluorochemicals with crystallizable spacer groups
  • Side chain fluorochemicals with crystallizable spacer groups

Examples

Experimental program
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Effect test

example

[0067] All chemicals used in the following examples were or could be obtained from Sigma-Aldrich, St. Louis, MO unless otherwise indicated.

example 1

[0069] CH 2 =CH(CH 2 ) m Synthesis of OH, m=15 and 20

[0070] CH was prepared essentially as described in the multistep synthesis of S. Mirviss, J. Org. Chem. 54 1948 (1989) 2 =CH(CH 2 ) 14 COOH and CH 2 =CH(CH 2 ) 19 COOH.

[0071] Under nitrogen atmosphere, 21.9g 0.082mol CH 2 =CH(CH 2 ) 14 A mixture of COOH and 250 ml of anhydrous diethyl ether was added dropwise to 100 ml of a 1M solution of lithium aluminum hydride in stirred diethyl ether in a dry 500 ml round bottom flask. After 30 minutes of adding the mixture to the flask, the exothermic reaction was allowed to raise the temperature of the reaction mixture to reflux temperature. The reaction was allowed to continue to reflux for four hours, then cooled to 7°C with an external ice bath.

[0072] The cooled reaction mixture was then slowly hydrolyzed using 4 mL of water, 4 mL of 15% sodium hydroxide, and 12 mL of water delivered by syringe through the septum port of a 500 mL round bottom flask...

example 2

[0085] C 4 F 9 (CH 2 ) 22 Synthesis of OH

[0086] to synthesize C with the above 4 f 9 (CH 2 ) 17 In a similar fashion to OH, C was treated with zinc in glacial acetic acid 4 f 9 CH 2 CHI(CH 2 ) 20 OH to provide a mixture of reduction products alcohol and acetic acid and their corresponding alkenes. The mixture was treated with potassium hydroxide essentially as above to hydrolyze ethyl acetate, and finally the mixture was treated with hydrogen to remove olefinic impurities and recrystallized from n-hexane. Approximately 16.8 g of white solid C was obtained from this step 4 f 9 (CH 2 ) 22 OH, 98% pure by GC / MS.

[0087] C 4 F 9 (CH 2 ) 22 Synthesis of OAcr

[0088] Then to synthesize C with the above 4 f 9 (CH 2 ) 17 In a similar fashion to OAcr, the C 4 f 9 (CH 2 ) 22 OH is converted to acrylate. The final acrylate product was about 97% pure as measured by GC / MS. Further analysis of the sample by fast atom bombard...

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Abstract

A fluorochemical derived from monomers with a side chain, wherein the side chain includes a perfluoroalkyl group with 1-6 carbon atoms and a hydrocarbon spacer group attached to the perfluoroalkyl group, wherein the spacer group has 15-50 carbon atoms. The perfluoroalkyl group is non-crystallizable at room temperature and the spacer group is crystallizable at room temperature.

Description

[0001] Cross References to Related Applications [0002] This application claims priority to US Provisional Patent Application No. 60 / 824,187, filed August 31, 2006, the disclosure of which is incorporated herein by reference in its entirety. technical field [0003] The present invention relates to fluorochemicals (e.g., fluorinated polymers and fluorinated polyurethanes) comprising one or more monomer units having perfluoroalkyl side chains, to coating compositions comprising the fluorochemicals, and Involves the substrate (and coating method) to which it is coated. In another aspect, the present invention is directed to a process for preparing monomers containing perfluoroalkyl side chains. Background technique [0004] Fluorinated polymers are generally composed of repeating monomeric units, each monomeric unit comprising a monomeric backbone moiety attached to a perfluoroalkyl side chain. The side chain typically includes a hydrocarbon spacer connecting the side chai...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C69/653C08F20/24C08F120/24
CPCC07C67/14C07C69/653C07C29/58C07C29/62C08F220/24Y10T428/3154C07C29/147C07C33/025C07C31/34C07C31/38
Inventor 理查德·M·弗林迈克尔·A·扬德拉希茨
Owner 3M INNOVATIVE PROPERTIES CO
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