Patent US5410073A successfully refreshed from Google Patents.
US5410073A
Expired / Lapsed
US
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Manufacture of polyfluoro nitrogen containing organic compounds
Assignee: EIDP Inc
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Filing: 1994-02-04
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Granted: 1995-04-25
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Expires: 2014-02-04
Abstract
Abstract Process comprising (I) reacting (a) at least one polyisocyanate or mixture of polyisocyanates which contains at least three isocyanate groups per molecule with (b) a stoichiometric deficiency of at least one fluorochemical compound which contains per molecule (i) a single functional group having one or more Zerewitinoff hydrogen atoms and (ii) at least two carbon atoms each of which contains at least two fluorine atoms, and (II) thereafter forming one or more urea linkages per mol of said polyisocyanate by reacting the remaining isocyanate groups with water in an amount sufficient to to react with from about 5% to about 60% of the isocyanate groups in said polyisocyanate.
Inventors
- 👤 Jack R. Kirchner
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-31 18:12
CPC Classifications
C; C07; C07C; C07C275/00; C07C275/46; C07C275/58; C07C275/62; Y; Y10; Y10T; Y10T428/00; Y10T428/249921; Y10T428/249953; Y10T428/249987; Y10T428/249991; Y10T442/00; Y10T442/20; Y10T442/2164; Y10T442/2172; Y10T442/2189; Y10T442/2262; Y10T442/2279; Y10T442/2287
Claims Analysis
Total Claims: 30
Claim 1
Independent Claim
154 words
A process for preparing polyfluoro organic compounds which contain at least one urea linkage in which (I) one reacts (a) at least one organic polyisocyanate or mixture of organic polyisocyanates which contains at least three isocyanate groups per molecule with (b) at least one fluorochemical compound which contains per molecule (i) a single functional group having one or more Zerewitinoff hydrogen atoms and (ii) at least two carbon atoms each of which contains at least two fluorine atoms, the amount of said fluorochemical compound being sufficient to react with 95% to 40% of said isocyanate groups, (II) thereafter forming one or more urea linkages per mol of said polyisocyanate by reacting the remaining isocyanate groups with water in an amount sufficient to react with from about 5% to about 60% of said isocyanate groups, and III recovering a polyfluoro organic compound, or mixture of polyfluoro organic compounds, which contains at least one urea linkage.
Claim 2
Dependent Claim
154 words
A process for preparing polyfluoro organic compounds which contain at least one urea linkage in which (I) one reacts (a) at least one organic polyisocyanate or mixture of organic polyisocyanates which contains at least three isocyanate groups per molecule with (b) at least one fluorochemical compound which contains per molecule (i) a single functional group having one or more Zerewitinoff hydrogen atoms and (ii) at least two carbon atoms each of which contains at least two fluorine atoms, the amount of said fluorochemical compound being sufficient to react with 95% to 40% of said isocyanate groups, (II) thereafter forming one or more urea linkages per mol of said polyisocyanate by reacting the remaining isocyanate groups with water in an amount sufficient to react with from about 5% to about 60% of said isocyanate groups, and III recovering a polyfluoro organic compound, or mixture of polyfluoro organic compounds, which contains at least one urea linkage.
Claim 3
Dependent Claim
24 words
The process claim 1 wherein the amount of water is sufficient to react with from about 10% to about 35% of said isocyanate groups.
Claim 4
Dependent Claim
23 words
The process of claim 2 wherein the amount of water is sufficient to react with about 15% to 30% of said isocyanate groups.
Claim 5
Dependent Claim
82 words
The process of claim 1 wherein said fluorochemical compound is represented by the formula: R.sup.f --R.sub.k --X--H in which R f is a monovalent aliphatic group containing at least two carbon atoms each of which contains at least two fluorine atoms; R is a divalent organic radical; k is 0 or 1; and X is --O--, --S--, or --N(R 1 )-- in which R 1 is H, alkyl containing 1 to 6 carbon atoms or a R f --R k -- group.
Claim 6
Dependent Claim
167 words
The process of claim 1 wherein said fluorochemical compound is represented by the formula: R.sup.f --R.sub.k --R.sup.2 --X--H in which R f is a monovalent aliphatic group containing at least two carbon atoms each of which contains at least two fluorine atoms; R is the divalent radical: --C m H 2m SO--; --C m H 2m SO 2 --,--SO 2 N(R 3 )--, or --CON(R 3 )--; m is 1 to 22, and R 3 is H or alkyl of 1 to 6 carbon atoms; R 2 is the divalent linear hydrocarbon radical: --C n H 2n --, ##STR10## n is 0 to 12, p is 1 to 50, and R 4 , R 5 and R 6 are the same or different H or alkyl containing 1 to 6 carbon atoms; k is 0 or 1; and X is --O--, --S--, or --N(R 7 )--; R 7 is H, alkyl containing 1 to 6 carbon atoms or a R f --R k --R 2 -- group.
Claim 7
Dependent Claim
30 words
The process of claim 5 wherein R f is a fully-fluorinated straight or branched aliphatic radical of 3 to 20 carbon atoms which is unsubstituted or interrupted by oxygen atoms.
Claim 8
Dependent Claim
49 words
The process of claim 6 wherein said fluorochemical compound is represented by the formula: R.sup.f --(CH.sub.2).sub.q --X--H in which R f is a mixture of perfluoroalkyl groups, CF 3 CF 2 (CF 2 ) r in which r is 2 to 18; and q is 1, 2 or 3.
Claim 9
Dependent Claim
37 words
The process of claim 7 wherein R f is a mixture of said perfluoroalkyl groups, CF 3 CF 2 (CF 2 ) r ; and r is 2, 4, 6, 8, 10, 12, 14, 16, and 18.
Claim 10
Dependent Claim
13 words
The process of claim 8 wherein X is oxygen and q is 2.
Claim 11
Dependent Claim
13 words
The process of claim 8 wherein r is predominately 4, 6 and 8.
Claim 12
Dependent Claim
12 words
The process of claim 8 wherein r is predominately 6 and 8.
Claim 13
Dependent Claim
19 words
The process of claim 8 wherein X is --N(R 7 )--, R 7 is H, and q is 2.
Claim 14
Dependent Claim
28 words
The process of claim 4 wherein said fluorochemical compound is represented by the formula: H(CF 2 CF 2 ) w CH 2 OH in which w is 1-10.
Claim 15
Dependent Claim
19 words
The process of claim 4 wherein said fluorochemical compound is represented by the formula: CF 3 (CF 3 )CHOH.
Claim 16
Dependent Claim
34 words
The process of claim 1 further characterized in that between about 1% and about 60% of said isocyanate groups are reacted with at least one non-fluorinated organic compound which contains one Zerewitinoff hydrogen atom.
Claim 17
Dependent Claim
104 words
The process of claim 15 wherein said non-fluorinated compound is represented by the formula: R.sup.10 --R.sup.11.sub.k --YH in which R 10 is a C 1 -C 18 alkyl, a C 1 -C 18 omega-alkenyl radical or a C 1 -C 18 omega-alkenoyl; R 11 is ##STR11## R 4 , R 5 and R 6 are the same or different H or alkyl radical containing 1 to 6 carbon atoms and p is 1 to 50; and k is 0 or 1; and Y is --O--, --S--, or --N(R 7 )-- in which R 7 is H or alkyl containing 1 to 6 carbon atoms.
Claim 18
Dependent Claim
12 words
The process of claim 16 wherein said non-fluorinated compound is an alkanol.
Claim 19
Dependent Claim
17 words
The process of claim 16 wherein said non-fluorinated compound is a monoalkyl ether of a poly(oxyalkylene) glycol.
Claim 20
Dependent Claim
17 words
The process of claim 18 wherein said non-fluorinated compound is a monomethyl ether of a poly(oxyethylene) glycol.
Claim 21
Dependent Claim
17 words
The process of claim 16 wherein said non-fluorinated compound is a monoalkenyl ether of a poly(oxyalkylene) glycol.
Claim 22
Dependent Claim
17 words
The process of claim 20 wherein said non-fluorinated compound is a monoallyl ether of a poly(oxyethylene) glycol.
Claim 23
Dependent Claim
26 words
The process of claim 1 wherein said polyisocyanate is represented by the formula: ##STR12## in which x is an integer equal to or greater than 1.
Claim 24
Dependent Claim
11 words
The process of claim 22 wherein x is 1 to 8.
Claim 25
Dependent Claim
23 words
The process of claim 1 wherein said polyisocyanate is represented by the formula: ##STR13## in which R 12 is a divalent hydrocarbon group.
Claim 26
Dependent Claim
18 words
The process of claim 24 wherein said divalent hydrocarbon radical is an aliphatic, alicyclic, aromatic or arylaliphatic radical.
Claim 27
Dependent Claim
12 words
The process of claim 25 wherein R 12 is a hexamethylene radical.
Claim 28
Dependent Claim
12 words
The process of claim 25 wherein R 12 is a toluene radical.
Claim 29
Dependent Claim
12 words
The process of claim 25 wherein R 12 is a cyclohexylene radical.
Claim 30
Dependent Claim
26 words
The process of claim 1 wherein said polyisocyanate is represented by the formula: ##STR14## in which R 13 is a methyl or ethyl radicals, and ##STR15##
References Cited (Backward Citations)
US3987227A
Cited
US4877540A
Cited
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| 3.5 Years (Year 4) | 1998-04-24 | 1998-10-24 | 1999-04-25 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 2002-04-24 | 2002-10-24 | 2003-04-25 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2006-04-24 | 2006-10-24 | 2007-04-25 | $7700.00 | Window Closed / Lapsed |