Monomers mono-substituted fluorinated oxetane

Details Monomers mono-substituted fluorinated oxetane Monomers mono-substituted fluorinated oxetane

1995-10-05

1997-08-05

Wilson, D. R.

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C07D30500

Patent

active

056544502

ABSTRACT:
This application is directed to novel fluorinated polymers and prepolymers derived from mono-substituted oxetane monomers having fluorinated alkoxymethylene side-chains and the method of making these compositions. The mono-substituted fluorinated oxetane monomers having fluorinated alkoxymethylene side-chains are prepared in high yield by the reaction of a fluorinated alkoxides with either 3-halomethyl-3-methyloxetane premonomers or aryl sulfonate derivative of 3-hydroxymethyl-3-methyloxetane premonomers. Preparation of a mono-substituted 3-bromomethyl-3-methyloxetane premonomer via a simple, high yield process amenable to commercial scaleup is also disclosed. The fluorinated oxetane monomers of this invention can be readily homo/co-polymerized in the presence of a Lewis acid and polyhydroxy compounds to obtain hydroxy-terminated polyether prepolymers having fluorinated alkoxymethylene side chains. Additionally, the fluorinated oxetane monomers can be copolymerized with non-fluorinated monomers such as tetrahydrofuran to give polyether prepolymers with improved hydrocarbon compatibility. These prepolymers are polydisperse and exhibit number average molecular weights from 5,000 to about 50,000. These prepolymers are amorphous oils with primary hydroxy end-groups and thus function efficiently as the soft block for the synthesis of a variety of thermoset/thermoplastic elastomers and plastics having the characteristics of very low surface energy, high hydrophobicity, low glass transition temperature and low coefficient of friction. The polyurethanes derived from the prepolymers of this invention are elastomeric and, in addition to the above characteristics, exhibit high moisture resistance, high tear strength and excellent adhesion to a variety of substrates.

REFERENCES:
patent: 2895921 (1959-07-01), Price
patent: 2895924 (1959-07-01), Hudy
patent: 2895931 (1959-07-01), Klug
patent: 2905647 (1959-09-01), Goddu
patent: 2909492 (1959-10-01), Schilling
patent: 3096344 (1963-07-01), Case
patent: 3210298 (1965-10-01), Weissermerl et al.
patent: 3347801 (1967-10-01), Stogryn
patent: 4097048 (1978-06-01), Falk et al.
patent: 4393199 (1983-07-01), Manser
patent: 4414384 (1983-11-01), Berkowitz et al.
patent: 4483978 (1984-11-01), Manser
patent: 4675452 (1987-06-01), Lagow et al.
patent: 4707540 (1987-11-01), Manser et al.
patent: 4764586 (1988-08-01), Manser et al.
patent: 4827042 (1989-05-01), Lagow et al.
patent: 4847427 (1989-07-01), Nappa
patent: 4864040 (1989-09-01), Oshaka et al.
patent: 4898981 (1990-02-01), Falk et al.
patent: 4946992 (1990-08-01), Falk et al.
patent: 4965342 (1990-10-01), Vandenberg et al.
patent: 4970295 (1990-11-01), Schuchardt
patent: 4988797 (1991-01-01), Wardle et al.
patent: 5000830 (1991-03-01), Marchionni
patent: 5097048 (1992-03-01), Falk et al.
L. Karam, "Synthese de Diols Telecheliques Halogenes Par Polymerization Cationique D'Oxetanes", Ph.D. Thesis, Ecole Nationale Superieure Chimie, MontPellier, France, pp. 1-22 and 114-147 (1991).
L. Karam, "Thesis Abstract, Ecole Nationale Superieure Chimie", Montpellier, France, pp. 1-4 (1992).
Copies provided in copending 08/371,914 or 08/477,168.

Affiliated with

Also associated with

Rating

Monomers mono-substituted fluorinated oxetane does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Monomers mono-substituted fluorinated oxetane, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Monomers mono-substituted fluorinated oxetane will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-1076128