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US4094911A
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Poly(perfluoroalkylene oxide) derivatives
Assignee: 3M Co
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Filing: 1973-06-25
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Granted: 1978-06-13
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Expires: 1993-06-25
Abstract
Abstract Polyfunctional poly(perfluoroalkylene oxide) compounds, such as compounds of the formula A--CF.sub.2 O(CF.sub.2 CF.sub.2 O).sub.m (CF.sub.2 O).sub.n CF.sub.2 --A' where A and A' are reactive radicals containing a polymerizable functional group, e.g., hydroxyl, are provided, such compounds being useful as monomers in the preparation of polymeric materials, e.g., polyurethanes, possessing unusual low temperature stability and resistance to solvents.
Inventors
- 👤 Ronald A. Mitsch
- 👤 Joseph La Mar Zollinger
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-26 23:32
CPC Classifications
C; C07; C07D; C07D263/00; C07D263/52; C07D263/62; C06; C06B; C06B45/00; C06B45/04; C06B45/06; C06B45/10; C07C; C07C265/00; C07C309/00; C07C309/63; C07C309/64; C07C309/65; C07D271/00; C07D271/02; C07D271/10; C07D303/00; C07D303/02; C07D303/12; C07D303/18; C07D303/20; C07D303/24; C08; C08G; C08G18/00; C08G18/06; C08G18/28; C08G18/40; C08G18/48; C08G18/50; C08G18/5003; C08G18/5015; C08G18/70; C08G18/72; C08G18/77; C08G18/771; C08G18/773; C08G65/00; C08G65/002; C08G65/005; C08G65/007; C08G65/02; C08G65/32; C08G65/329; C08G65/333; C08G65/336; C08G69/00; C08G69/42; C08G77/00; C08G77/42; C08G77/46; C10; C10M; C10M3/00; C10M2211/00; C10M2211/02; C10M2213/00; C10M2213/04; C10M2213/06; C10M2215/00; C10M2215/08; C10M2215/082; C10M2215/14; C10M2215/16; C10M2215/22; C10M2215/221; C10M2215/222; C10M2215/225; C10M2215/226; C10M2215/24; C10M2215/28; C10M2215/30; C10M2217/00; C10M2217/02; C10M2217/04; C10M2221/00; C10M2221/04; C10M2227/00; C10M2227/02; C10M2227/04; C10N; C10N2040/00; C10N2040/08; C10N2040/14; C10N2040/16; C10N2040/17; C10N2040/175; C10N2040/18; C10N2040/185
Claims Analysis
Total Claims: 15
Claim 1
Independent Claim
161 words
Linear functionally-terminated poly(perfluoroalkylene oxide) compounds having the formula A--CF.sub.2 --O--(CF.sub.2 CF.sub.2 O).sub.m (CF.sub.2 O).sub.n CF.sub.2 --A' where A and A' are --X a YZ b or --X' a' Y'Z' b' , X and X' are each a polyvalent linking organic radical, Y and Y' are each a polyvalent linking organic radical free of non-aromatic double bonds, Z and Z' are each a polymerizable functional group, a and a' are zero or one, b and b' are integers of 1 to 3, m and n designate the number of randomly distributed perfluoroethyleneoxy and perfluoromethyleneoxy subunits, respectively, the ratio m/n being 0.2/1 to 5/1, said compounds having a number average molecular weight of 500 to 20,000, a glass transition temperature lower than -78° C, and polymerizable to polymers having recurrent backbone units of the formula --CF 2 O(CF 2 CF 2 O) m (CF 2 O) n --CF 2 -- which impart to the polymers a glass transition temperature lower than -78° C.
Claim 2
Dependent Claim
161 words
Linear functionally-terminated poly(perfluoroalkylene oxide) compounds having the formula A--CF.sub.2 --O--(CF.sub.2 CF.sub.2 O).sub.m (CF.sub.2 O).sub.n CF.sub.2 --A' where A and A' are --X a YZ b or --X' a' Y'Z' b' , X and X' are each a polyvalent linking organic radical, Y and Y' are each a polyvalent linking organic radical free of non-aromatic double bonds, Z and Z' are each a polymerizable functional group, a and a' are zero or one, b and b' are integers of 1 to 3, m and n designate the number of randomly distributed perfluoroethyleneoxy and perfluoromethyleneoxy subunits, respectively, the ratio m/n being 0.2/1 to 5/1, said compounds having a number average molecular weight of 500 to 20,000, a glass transition temperature lower than -78° C, and polymerizable to polymers having recurrent backbone units of the formula --CF 2 O(CF 2 CF 2 O) m (CF 2 O) n --CF 2 -- which impart to the polymers a glass transition temperature lower than -78° C.
Claim 3
Dependent Claim
105 words
Linear hydroxy-terminated poly(perfluoroalkylene oxide) compounds having a number average molecular weight of 500 to 10,000 and the general formula R--CF.sub.2 O--(CF.sub.2 CF.sub.2 O).sub.m (CF.sub.2 O).sub.n OCF.sub.2 --R' where R and R' are hydroxy-substituted organic radicals, where m and n designate randomly distributed perfluoroethyleneoxy and perfluoromethyleneoxy backbone subunits, respectively, the ratio m/n being 0.2/1 to 5/1, said compounds having a glass transition temperature lower than -78° C and polymerizable to polyurethanes having recurrent backbone units of the formula --CF 2 O--(CF 2 CF 2 O) m (CF 2 O) n --CF 2 -- which impart to the polyurethanes a glass transition temperature lower than -78° C.
Claim 4
Dependent Claim
105 words
Linear hydroxy-terminated poly(perfluoroalkylene oxide) compounds having a number average molecular weight of 500 to 10,000 and the general formula R--CF.sub.2 O--(CF.sub.2 CF.sub.2 O).sub.m (CF.sub.2 O).sub.n OCF.sub.2 --R' where R and R' are hydroxy-substituted organic radicals, where m and n designate randomly distributed perfluoroethyleneoxy and perfluoromethyleneoxy backbone subunits, respectively, the ratio m/n being 0.2/1 to 5/1, said compounds having a glass transition temperature lower than -78° C and polymerizable to polyurethanes having recurrent backbone units of the formula --CF 2 O--(CF 2 CF 2 O) m (CF 2 O) n --CF 2 -- which impart to the polyurethanes a glass transition temperature lower than -78° C.
Claim 5
Dependent Claim
12 words
The poly(perfluoroalkylene oxides) of claim 2 where R and R' are methylol.
Claim 6
Dependent Claim
24 words
The poly(perfluoroalkylene oxides) of claim 2 wherein said ratio m/n is 0.7/1 to 1.6/1, and said glass transition temperature is lower than -90° C.
Claim 7
Dependent Claim
16 words
The poly(perfluoroalkylene oxides) of claim 2 having a number average molecular weight of 800 to 5,000.
Claim 8
Dependent Claim
14 words
The poly(perfluoroalkylene oxides) of claim 2 wherein R and R' are hydroxy-substituted aliphatic radicals.
Claim 9
Dependent Claim
39 words
The poly(perfluoroalkylene oxides) of claim 2 wherein R and R' are devoid of active hydrogen atoms more reactive with isocyanato than said hydroxy substituent and, in addition to said hydroxy substituent, can contain substituents which are non-reactant with isocyanato.
Claim 10
Dependent Claim
29 words
The poly(perfluoroalkylene oxides) of claim 2 wherein R and R' have less than 12 carbon atoms and are otherwise unsubstituted or contain other substituents which are non-reactive with isocyanato.
Claim 11
Dependent Claim
58 words
Liquid, linear hydroxy-terminated poly(perfluoroalkylene oxides) having a glass transition temperature lower than -78° C., a number average molecular weight of 500 to 10,000, and having the general formula HOCH.sub.2 --CF.sub.2 O--(CF.sub.2 CF.sub.2 O).sub.m (CF.sub.2 O).sub.n --CF.sub.2 --CH.sub.2 OH where m and n designate randomly distributed perfluoroethyleneoxy and perfluoromethyleneoxy backbone subunits, respectively, the ratio m/n being 0.2/1 to 5/1.
Claim 12
Dependent Claim
58 words
Liquid, linear hydroxy-terminated poly(perfluoroalkylene oxides) having a glass transition temperature lower than -78° C., a number average molecular weight of 500 to 10,000, and having the general formula HOCH.sub.2 --CF.sub.2 O--(CF.sub.2 CF.sub.2 O).sub.m (CF.sub.2 O).sub.n --CF.sub.2 --CH.sub.2 OH where m and n designate randomly distributed perfluoroethyleneoxy and perfluoromethyleneoxy backbone subunits, respectively, the ratio m/n being 0.2/1 to 5/1.
Claim 13
Dependent Claim
33 words
The poly(perfluoroalkylene oxides) of claim 9, said ratio m/n is 0.7/1, said glass transition temperature is less than -100° C., said poly(perfluoroalkylene oxides) having a number average molecular weight of 1700 to 2840.
Claim 14
Dependent Claim
106 words
Liquid, linear hydroxy-terminated poly(perfluoroalkylene oxide) compounds having a glass transition temperature lower than -78° C, a number average molecular weight of 500 to 10,000, and having the general formula R--CF.sub.2 O--(CF.sub.2 CF.sub.2 O).sub.m (CF.sub.2 O).sub.n --CF.sub.2 --R' where R and R' are hydroxy-substituted aliphatic radicals, where m and n designate randomly distributed perfluoroethyleneoxy and perfluoromethyleneoxy backbone subunits, respectively, the ratio m/n being 0.2/1 to 5/1, said compounds being polymerizable to polyurethanes having recurrent backbone units of the formula --CF 2 O--(CF 2 CF 2 O) m (CF 2 O) n --CF 2 -- which impart to the polyurethanes a glass transition temperature lower than -78° C.
Claim 15
Dependent Claim
106 words
Liquid, linear hydroxy-terminated poly(perfluoroalkylene oxide) compounds having a glass transition temperature lower than -78° C, a number average molecular weight of 500 to 10,000, and having the general formula R--CF.sub.2 O--(CF.sub.2 CF.sub.2 O).sub.m (CF.sub.2 O).sub.n --CF.sub.2 --R' where R and R' are hydroxy-substituted aliphatic radicals, where m and n designate randomly distributed perfluoroethyleneoxy and perfluoromethyleneoxy backbone subunits, respectively, the ratio m/n being 0.2/1 to 5/1, said compounds being polymerizable to polyurethanes having recurrent backbone units of the formula --CF 2 O--(CF 2 CF 2 O) m (CF 2 O) n --CF 2 -- which impart to the polyurethanes a glass transition temperature lower than -78° C.
References Cited (Backward Citations)
US3419532A
Cited
US3419531A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1981-06-12 | 1981-12-12 | 1982-06-13 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1985-06-12 | 1985-12-12 | 1986-06-13 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1989-06-12 | 1989-12-12 | 1990-06-13 | $7700.00 | Window Closed / Lapsed |