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

Patent metadata

Field	Value
Publication number	US-9688649-B2
Application number	US-201414527877-A
Country	US
Kind code	B2
Filing date	Oct 30, 2014
Priority date	Dec 11, 2008
Publication date	Jun 27, 2017
Grant date	Jun 27, 2017

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.

First claim

We claim:

1. A perfluoropolyether thiol compound comprising (a) a monovalent or divalent perfluoropolyether segment that comprises one or two divalent polyhexafluoropropyleneoxy group, (b) at least one mercapto group, and (c) at least one intervening divalent carbonylimino moiety, —C(═O)—NH—, that is directly or indirectly bonded through its carbon atom to said perfluoropolyether segment and indirectly bonded through its nitrogen atom to said mercapto group; wherein said compound is one of a class that is represented by the following general formula (II):
R f ′—(O[CF(CF 3 )CF 2 O] a CF(CF 3 )—[C(═O)—N(R)-Q—(SH) x ]) y   (II)

wherein R f ′ is a linear or branched perfluoroalkyl or perfluoroalkylene group; a has an average value of 4 to 20; R is hydrogen; Q is a divalent organic linking group selected from —CH 2 CH 2 CH 2 —[NH—C(═O)]—CH 2 CH 2 CH 2 —, —CH 2 CH 2 CH 2 —[N(CH 3 )—C(═O)]—CH 2 CH 2 CH 2 —, —CH 2 CH 2 —[NH—C(═O)]—CH 2 CH 2 CH 2 —, —CH 2 CH 2 —[O—C(═O)]—CH 2 CH 2 —, —(CH 2 CH 2 O) 2 —[C(═O)]—CH 2 CH 2 —, and combinations thereof; x is an integer of 1; and y is an integer of 1 or 2.

2. The compound of claim 1 , wherein said compound is selected from
F[CF(CF 3 )CF 2 O] a CF(CF 3 )—C(═O)—NH—(CH 2 ) 3 —N(CH 3 )C(═O)—(CH 2 ) 3 —SH,
HS—(CH 2 ) 3 —C(═O)—NH—(CH 2 ) 2 —NH—C(═O)—CF(CF 3 )(OCF 2 CF(CF 3 ) b —OCF 2 CF 2 CF 2 CF 2 O(CF(CF 3 )CF 2 O) c —CF(CF 3 )—C(═O)—NH—(CH 2 ) 2 —NHC(═O)—(CH 2 ) 3 —SH,
F[CF(CF 3 )CF 2 O] a CF(CF 3 )—C(═O)NH—CH 2 CH 2 —O—C(═O)—CH 2 CH 2 SH,
F[CF(CF 3 )CF 2 O] a CF(CF 3 )—C(═O)NH—(CH 2 CH 2 O) 2 —C(═O)—CH 2 CH 2 SH,
and mixtures thereof, wherein a has an average value of 4 to 20 and b+c has an average value of 4 to 15.

Assignees

• 3M Innovative Properties Co

Inventors

• Iyer Suresh S
• Pellerite Mark J
• Jariwala Chetan P

Classifications

• C08F2/38

  Polymerisation using regulators, e.g. chain terminating agents {, e.g. telomerisation} · CPC title

• C07C323/41

  Y being a hydrogen or an acyclic carbon atom · CPC title

• G03F7/0002

  Lithographic processes using patterning methods other than those involving the exposure to radiation, e.g. by stamping · CPC title

• C07D303/48 Primary

  with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms, e.g. ester or nitrile radicals · CPC title

• B82Y30/00

  Nanotechnology for materials or surface science, e.g. nanocomposites · CPC title