US3996281A
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Fluorinated carboxylic acid amides and polymerization products thereof
Assignee: Novartis Corp
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Filing: 1975-02-06
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Granted: 1976-12-07
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Expires: 1995-02-06
Abstract
Abstract New fluorinated carboxylic acid amides of the formula ##STR1## are provided wherein R f is a perfluoroalkyl radical with 1 to 18 carbon atoms, R is hydrogen or methyl, R 1 is hydrogen or R f CHOHCHR--, if m is 1, and hydrogen, alkyl with 1 to 18 carbon atoms, cycloalkyl with 5 or 6 carbon atoms, hydroxyalkyl with 2 to 6 carbon atoms, alkoxyalkyl with 1 to 4 carbon atoms in the alkoxy moiety or R f CHOHCHR--, if m is 0, A is an ethylenically unsaturated hydrocarbon radical with 2 or 3 carbon atoms, m is 0 or 1, y is 1 or 2 and p is an integer from 2 to 6. The fluorinated carboxylic acid amides are useful e.g. as wetting agents, emulsifiers or dispersants and for producing oil-repellent finishes on porous or nonporous substrates or as intermediates for the manufacture of homo- or copolymers, which show also oil-repellent properties.
Inventors
- 👤 Helmut Huber-Emden
- 👤 Paul Schafer
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-30 00:52
CPC Classifications
C; C08; C08F; C08F20/00; C08F20/02; C08F20/52; C08F20/54; C08F20/60; D; D06; D06M; D06M15/00; D06M15/19; D06M15/21; D06M15/285; C10; C10M; C10M2215/00; C10M2215/08; C10M2215/082; C10M2215/24; C10M2215/28
Claims Analysis
Total Claims: 29
Claim 1
Independent Claim
112 words
Fluorinated carboxylic acid amides of the formula ##STR37## wherein R f is a perfluoroalkyl radical with 4 to 14 carbon atoms, R is hydrogen or methyl, R 1 is hydrogen or R f CHOHCHR--, if m is 1; and hydrogen, alkyl with 1 to 18 carbon atoms, cycloalkyl with 5 or 6 carbon atoms, hydroxylalkyl with 2 to 6 carbon atoms, alkoxyalkyl with 1 to 4 carbon atoms in the alkoxy moiety or R f CHOHCHR--, if m is 0, A is an ethylenically unsaturated hydrocarbon radical with 2 or 3 carbon atoms, m is 0 or 1, y is 1 or 2 and p is an integer from 2 to 6.
Claim 2
Dependent Claim
112 words
Fluorinated carboxylic acid amides of the formula ##STR37## wherein R f is a perfluoroalkyl radical with 4 to 14 carbon atoms, R is hydrogen or methyl, R 1 is hydrogen or R f CHOHCHR--, if m is 1; and hydrogen, alkyl with 1 to 18 carbon atoms, cycloalkyl with 5 or 6 carbon atoms, hydroxylalkyl with 2 to 6 carbon atoms, alkoxyalkyl with 1 to 4 carbon atoms in the alkoxy moiety or R f CHOHCHR--, if m is 0, A is an ethylenically unsaturated hydrocarbon radical with 2 or 3 carbon atoms, m is 0 or 1, y is 1 or 2 and p is an integer from 2 to 6.
Claim 3
Dependent Claim
12 words
Fluorinated carboxylic acid amides according to claim 1, of the formula ##STR38##
Claim 4
Dependent Claim
55 words
wherein R f is a perfluoroalkyl radical with 4 to 14 carbon atoms, R 2 is hydrogen or R f CHOHCHR--, R and R 3 are hydrogen or methyl, R 4 is hydrogen, methyl or (R f CHOHCHR) 2 N(CH 2 ) p NR 2 CO-- and p is an integer from 2 to 6.
Claim 5
Dependent Claim
55 words
wherein R f is a perfluoroalkyl radical with 4 to 14 carbon atoms, R 2 is hydrogen or R f CHOHCHR--, R and R 3 are hydrogen or methyl, R 4 is hydrogen, methyl or (R f CHOHCHR) 2 N(CH 2 ) p NR 2 CO-- and p is an integer from 2 to 6.
Claim 6
Dependent Claim
74 words
Fluorinated carboxylic acid amides according to claim 1, of the formula ##STR39## wherein R f is a perfluoroalkyl radical with 4 to 14 carbon atoms, R and R 3 are hydrogen or methyl, R 4 is hydrogen, methyl or R f CHOHCHRNR 5 CO-- and R 5 is hydrogen, alkyl with 1 to 12 carbon atoms, hydroxyalkyl with 2 to 6 carbon atoms, cycloalkyl with 5 or 6 carbon atoms or R f CHOHCHR--.
Claim 7
Dependent Claim
60 words
Fluorinated carboxylic acid amides according to claim 2, of the formula ##STR40## wherein R and R 3 are hydrogen or methyl, R 6 is hydrogen or (C n F 2n +1 CHOHCHR) 2 --NCH 2 CH 2 NR 7 CO--, R 7 is hydrogen or C n F 2n +1 CHOHCHR-- and n is an integer from 4 to 14.
Claim 8
Dependent Claim
66 words
Fluorinated carboxylic acid amides according to claim 4, of the formula ##STR41## wherein R 3 is hydrogen or methyl, R 8 is hydrogen or (C n .sbsb.1 F 2n +1 CHOHCH 2 ) 2 --NCH 2 CH 2 NR 9 CO--, R 9 is hydrogen or C n .sbsb.1 F 2n .sbsb.1 +1 CHOHCH 2 -- and n 1 is an integer from 6 to 12.
Claim 9
Dependent Claim
29 words
Fluorinated carboxylic acid amides according to claim 5, of the formula ##STR42## wherein R 3 is hydrogen or methyl an n 1 is an integer from 6 to 12.
Claim 10
Dependent Claim
13 words
A fluorinated carboxylic acid amide according to claim 6, of the formula ##STR43##
Claim 11
Dependent Claim
29 words
Fluorinated carboxylic acid amides according to claim 5, of the formula ##STR44## wherein R 3 is hydrogen or methyl and n 1 is an integer from 6 to 12.
Claim 12
Dependent Claim
75 words
Fluorinated carboxylic acid amides according to claim 3, of the formula ##STR45## wherein R and R 3 are hydrogen or methyl, R 10 is hydrogen, alkyl with 1 to 8 carbon atoms, hydroxyalkyl with 2 to 6 carbon atoms, cycloalkyl with 5 or 6 carbon atoms or C n F 2n +1 CHOHCHR--, R 11 is hydrogen or C n F 2n +1 CHOHCHRNR 10 CO-- and n is an integer from 4 to 14.
Claim 13
Dependent Claim
71 words
Fluorinated carboxylic acid amides according to claim 9, of the formula ##STR46## wherein R and R 3 are hydrogen or methyl, R 12 is hydrogen, alkyl with 1 to 8 carbon atoms, --CH 2 CH 2 OH or C n .sbsb.1 F 2n .sbsb.1 +1 --CHOHCHR--, R 13 is hydrogen or C n .sbsb.1 F 2n .sbsb.1 +1 CHOHCHRNR 12 CO-- and n 1 is an integer from 6 to 12.
Claim 14
Dependent Claim
35 words
Fluorinated carboxylic acid amides according to claim 10, of the formula ##STR47## wherein R 14 is hydrogen or alkyl with 1 to 8 carbon atoms and n 1 is an integer from 6 to 12.
Claim 15
Dependent Claim
14 words
Fluorinated carboxylic acid amides according to claim 11, of the formulae ##STR48## and ##STR49##
Claim 16
Dependent Claim
29 words
Fluorinated carboxylic acid amides according to claim 10, of the formula ##STR50## wherein R 3 is hydrogen or methyl and n 1 is an integer from 6 to 12.
Claim 17
Dependent Claim
13 words
A fluorinated carboxylic acid amide according to claim 13, of the formula ##STR51##
Claim 18
Dependent Claim
29 words
Fluorinated carboxylic acid amides according to claim 10, of the formula ##STR52## wherein R 3 is hydrogen or methyl and n 1 is an integer from 6 to 12.
Claim 19
Dependent Claim
13 words
A fluorinated carboxylic acid amide according to claim 15, of the formula ##STR53##
Claim 20
Dependent Claim
22 words
Polymerisation products of at least one perfluorinated carboxylic acid amide according to claim 1 and, optionally, other copolymerisable, ethylenically unsaturated monomeric compounds.
Claim 21
Dependent Claim
124 words
Homopolymers according to claim 17 which contain recurring units of the formula ##STR54## wherein R f is a perfluoroalkyl radical with 4 to 14 carbon atoms, R is hydrogen or methyl, R 1 is hydrogen or R f CHOHCHR--, if m is 1, and hydrogen, alkyl with 1 to 18 carbon atoms, cycloalkyl with 5 or 6 carbon atoms, hydroxylalkyl with 2 to 6 carbon atoms, alkoxyalkyl with 1 to 4 carbon atoms in the alkoxy moiety or R f CHOHCHR--, if m is 0, ##STR55## is a recurring radical which is derived from an ethylenically unsaturated hydrocarbon radical with 2 to 3 carbon atoms, m is 0 or 1, y is 1 or 2 and p is an integer from 2 to 6.
Claim 22
Dependent Claim
68 words
Homopolymers according to claim 18 which contain recurring units of the formula ##STR56## wherein R f is a perfluoroalkyl radical with 4 to 14 carbon atoms, R 2 is hydrogen or R f CHOHCHR--, R and R 3 are hydrogen or methyl, R 4 is hydrogen, methyl or (R f CHOHCHR) 2 N(CH 2 ) p NR 2 CO-- and p is an integer from 2 to 6.
Claim 23
Dependent Claim
75 words
Homopolymers according to claim 18 which contain recurring units of the formula ##STR57## wherein R f is a perfluoroalkyl radical with 4 to 14 carbon atoms, R and R 3 are hydrogen or methyl, R 4 is hydrogen, methyl or R f CHOHCHRNR 5 CO-- and R 5 is hydrogen, alkyl with 1 to 12 carbon atoms, hydroxyalkyl with 2 to 6 carbon atoms, cycloalkyl with 5 or 6 carbon atoms or R f CHOHCHR--.
Claim 24
Dependent Claim
22 words
Homopolymers according to claim 18, wherein R f is a straight-chain or a branched perfluoroalkyl radical with 6 to 12 carbon atoms.
Claim 25
Dependent Claim
136 words
Copolymers according to claim 17 which contain recurring units of the formula ##STR58## wherein R f is a perfluoroalkyl radical with 4 to 14 carbon atoms, R is hydrogen or methyl, R 1 is hydrogen or R f CHOHCHR--, if m is 1, and hydrogen, alkyl with 1 to 18 carbon atoms, cycloalkyl with 5 or 6 carbon atoms, hydroxyalkyl with 2 to 6 carbon atoms, alkoxyalkyl with 1 to 4 carbon atoms in the alkoxy moiety or R f CHOHCHR--, if m is 0, A' is a recurring radical which is derived from an ethylenically unsaturated hydrocarbon radical with 2 or 3 carbon atoms, m is 0 or 1, y is 1 or 2 and p is an integer from 2 to 6, and recurring units of at least one other ethylenically unsaturated monomeric compound.
Claim 26
Dependent Claim
68 words
Copolymers according to claim 22 which contain recurring units of the formula ##STR59## wherein R f is a perfluoroalkyl radical with 4 to 14 carbon atoms, R 2 is hydrogen or R f CHOHCHR--, R and R 3 are hydrogen or methyl, R 4 is hydrogen, methyl or (R f CHOHCHR) 2 N(CH 2 ) p NR 2 CO-- and p is an integer from 2 to 6.
Claim 27
Dependent Claim
75 words
Copolymers according to claim 22 which contain recurring units of the formula ##STR60## wherein R f is a perfluoroalkyl radical with 4 to 14 carbon atoms, R and R 3 are hydrogen or methyl, R 4 is hydrogen, methyl or R f CHOHCHRNR 5 CO-- and R 5 is hydrogen, alkyl with 1 to 12 carbon atoms, hydroxyalkyl with 2 to 6 carbon atoms, cycloalkyl with 5 or 6 carbon atoms or R f CHOHCHR--.
Claim 28
Dependent Claim
22 words
Copolymers according to claim 22, wherein R f is a straight-chain or a branched perfluoroalkyl radical with 6 to 12 carbon atoms.
Claim 29
Dependent Claim
30 words
Copolymers according to claim 22 wherein esters, amides or methylolamides of acrylic or methacrylic acid, styrenes, vinyl halides, vinyl esters of organic acids or polymerisable olefins are used as comonomers.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1979-12-07 | 1980-06-07 | 1980-12-07 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1983-12-07 | 1984-06-07 | 1984-12-07 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1987-12-07 | 1988-06-07 | 1988-12-07 | $7700.00 | Window Closed / Lapsed |