Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Amide-linked perfluoropolyether thiol compounds and processes for their preparation and use

A technology of mercaptan compound and perfluoropolyether, which is applied in the direction of mercaptan preparation, polyether coating, photoplate making process of patterned surface, etc., can solve the problems of surface depletion and depletion, and achieve cost-effective results

Inactive Publication Date: 2012-01-04
3M INNOVATIVE PROPERTIES CO
View PDF16 Cites 6 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] However, when used in coatings or films, many fluorinated polyethers tend to diffuse to the surface of the coating or film and become depleted over time (for example, due to repeated cleaning of the surface)

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Amide-linked perfluoropolyether thiol compounds and processes for their preparation and use
  • Amide-linked perfluoropolyether thiol compounds and processes for their preparation and use
  • Amide-linked perfluoropolyether thiol compounds and processes for their preparation and use

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0064] Preparation of perfluoropolyether thiol compounds

[0065] The perfluoropolyetherthiol compounds of the present invention can be prepared by various methods. For example, perfluoropolyether derivatives such as methyl esters, acid chlorides, or acid fluorides can be reacted with amine-functional alkanethiols (e.g., 2-aminoethanethiol) in water under basic conditions (e.g., NaOH or KOH). ) or the corresponding alkyl ammonium salt (for example, SH-CH 2 CH 2 -NH 3 + Cl - )reaction. However, such methods may provide complex product mixtures containing relatively low yields of the desired amide-linked perfluoropolyetherthiol compound.

[0066] Thus, the preferred method of preparation is the method of the present invention, which provides the desired compound in relatively pure form as the main product of the ring-opening reaction of the thiolactone with the corresponding amine derivative of the perfluoropolyether. The method of the present invention comprises: (a) p...

example

[0090] Objects and advantages of this invention are further illustrated by the following examples, but the particular materials and amounts thereof recited in these examples, as well as other conditions and details, should not be construed to unduly limit this invention. These examples are illustrative only, and are not intended to limit the scope of the appended claims.

[0091] Material

[0092] γ-thiobutyrolactone, mercaptoethanolammonium hydrochloride, triethylamine, N-methyl-1,3-diaminopropane, monoethanolamine, ethylenediamine, diisopropylethylamine and methanesulfonyl chloride From Aldrich Chemical Company, Milwaukee, WI. All solvents were standard reagent grade obtained from commercial sources and were used without further purification unless otherwise specified.

[0093] Unless otherwise indicated, "HFPO-" refers to the methyl ester F(CF(CF 3 ) CF 2 O) a CF(CF 3 )C(=O)OCH 3 The monovalent terminal group F(CF(CF 3 ) CF 2 O) a CF(CF 3 )-, wherein "a" averag...

example 1

[0103] HFPO-C(=O)-NH-(CH 2 ) 3 -N(CH 3 )C(=O)-(CH 2 ) 3 Synthesis of -SH (perfluoropoly Etherthiol compound A)

[0104] A 50 mL round bottom flask equipped with a magnetic stirring bar, oil bath, reflux condenser, and nitrogen inlet was charged with HFPO-C(=O)NH-CH under nitrogen atmosphere. 2 CH 2 CH 2 -N(CH 3 )H (5 g, 0.0039 moles), γ-thiobutyrolactone (4.03 g, 10 molar equivalents) and tetrahydrofuran (THF) (25 g). The resulting mixture was cloudy and it was stirred at room temperature for 5 minutes. Triethylamine (3.985 g, 10 molar equivalents) was added dropwise to the mixture via syringe at room temperature. The mixture became clear after addition of triethylamine and it was stirred at 75°C for 16 hours. Excess unreacted γ-thiobutyrolactone was distilled off under vacuum, and the resulting mixture was poured into ice water. The resulting organic phase was extracted with HFE-7100 and MgSO 4 Dry and filter. The solvent was removed under v...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

PropertyMeasurementUnit
Number average molecular weightaaaaaaaaaa
Number average molecular weightaaaaaaaaaa
Average molecular weightaaaaaaaaaa
Login to View More

Abstract

A perfluoropolyether thiol compound comprises a perfluoropolyether segment, at least one mercapto group (-SH), and at least one intervening divalent carbonylimino moiety (-C(=O)-NR-, wherein R is hydrogen or alkyl). The compound can be produced, for example, by a ring-opening reaction of thiolactones with perfluoropolyether-substituted, primary or secondary amines. The compound can be used, for example, as a polymerization chain transfer agent, as an intermediate for the preparation of functional group-containing fluorochemical derivatives such as disulfides, and as a fluorinated surface treatment.

Description

[0001] priority statement [0002] This patent application claims priority to US Provisional Application Nos. 61 / 121,598 and 61 / 121,605, both filed December 11, 2008, the contents of which are hereby incorporated by reference. technical field [0003] The present invention relates to fluorinated thiol compounds and, in another aspect, to methods for their preparation. Background technique [0004] Fluorinated polyethers (e.g., perfluoropolyethers) have been used to prepare coating compositions applied to substrates (e.g., hard surface and fibrous substrates) to impart low surface energy properties such as oil and and / or water repellency (oleophobicity and / or hydrophobicity). Perfluoropolyether films have also been used in a variety of applications, including for magnetic recording media and / or electrical contacts (e.g., as lubricants to reduce friction and wear, protect surfaces from corrosion, and / or to render electrical conductivity) . [0005] However, when used in co...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
IPC IPC(8): C07C323/52C07C323/25C07C319/02C08G65/00C09D171/02B05D5/00
CPCC07C323/52B82Y40/00B82Y30/00C09D171/02C08G65/334C07C323/41B05D1/185C08G65/007G03F7/0002C07C323/60C07D303/48B82Y10/00C08F2/38
Inventor 苏赖斯·艾耶尔马克·J·佩莱里特凯坦·P·亚里瓦拉
Owner 3M INNOVATIVE PROPERTIES CO
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com