GB1231946A – – Google Patents
GB1231946A – – Google Patents
Info
Publication number
GB1231946A
GB1231946A
GB1231946DA
GB1231946A
GB 1231946 A
GB1231946 A
GB 1231946A
GB 1231946D A
GB1231946D A
GB 1231946DA
GB 1231946 A
GB1231946 A
GB 1231946A
Authority
GB
United Kingdom
Prior art keywords
compound
reaction
give
prepared
group
Prior art date
1969-03-20
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
1969-03-20
Filing date
1969-03-20
Publication date
1971-05-12
1969-03-20
Application filed
filed
Critical
1971-05-12
Publication of GB1231946A
publication
Critical
patent/GB1231946A/en
Status
Expired
legal-status
Critical
Current
Links
Espacenet
Global Dossier
Discuss
Classifications
D—TEXTILES; PAPER
D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
D06M15/564—Polyureas, polyurethanes or other polymers having ureide or urethane links; Precondensation products forming them
D06M15/568—Reaction products of isocyanates with polyethers
C—CHEMISTRY; METALLURGY
C07—ORGANIC CHEMISTRY
C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
C07C271/06—Esters of carbamic acids
C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
C07C271/12—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
C—CHEMISTRY; METALLURGY
C07—ORGANIC CHEMISTRY
C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
C07C317/00—Sulfones; Sulfoxides
C07C317/16—Sulfones; Sulfoxides having sulfone or sulfoxide groups and singly-bound oxygen atoms bound to the same carbon skeleton
C07C317/18—Sulfones; Sulfoxides having sulfone or sulfoxide groups and singly-bound oxygen atoms bound to the same carbon skeleton with sulfone or sulfoxide groups bound to acyclic carbon atoms of the carbon skeleton
C—CHEMISTRY; METALLURGY
C07—ORGANIC CHEMISTRY
C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
C07C43/00—Ethers; Compounds having groups, groups or groups
C07C43/02—Ethers
C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
C07C43/04—Saturated ethers
C07C43/13—Saturated ethers containing hydroxy or O-metal groups
C07C43/137—Saturated ethers containing hydroxy or O-metal groups containing halogen
D—TEXTILES; PAPER
D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
D06M13/402—Amides imides, sulfamic acids
D06M13/425—Carbamic or thiocarbamic acids or derivatives thereof, e.g. urethanes
D—TEXTILES; PAPER
D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
D06M13/402—Amides imides, sulfamic acids
D06M13/425—Carbamic or thiocarbamic acids or derivatives thereof, e.g. urethanes
D06M13/428—Carbamic or thiocarbamic acids or derivatives thereof, e.g. urethanes containing fluorine atoms
D—TEXTILES; PAPER
D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
D06M15/39—Aldehyde resins; Ketone resins; Polyacetals
D06M15/423—Amino-aldehyde resins
Abstract
1,231,946. Perfluoroalkyl carbamates. FMC CORP. 20 March, 1969, No. 14654/69. Heading C2C. [Also in Division D1] Novel compounds of formula and their N-hydroxymethyl or N-C 1-4 -alkoxymethyl derivative, wherein R f is a C 4-16 perfluoroalkyl group and Y is an alkylene bridge optionally interrupted by -S-, -SO-, -SO 2 or -N(R)-, R being a C 1-4 alkyl or C 1-4 hydroxyalkyl group, no interrupting atom being directly connected to the group R f or to the carbamate group and Y having, in the direct linking chain, 2 to 12 carbon atoms in a non-interrupted bridge and 2 to 60 carbon atoms in an interrupted bridge, are prepared by (a) reaction of a compound R f -Y-OH with a compound ROCONH 2 , wherein R is a C 1-4 alkyl group, or (b) deiodination of an iodosubstituted bridge Y by catalytic hydrogenation, followed if desired by methylolation and etherification. Examplified groups Rf are perfluoroheptyl and perfluorooctyl groups. The compounds of the invention are used to impart oil- and water-repelling properties. Compound of formula wherein R f is a perfluoroheptyl or perfluorooctyl group are prepared by reaction of a compound R f I with 2-allyloxyethanol and azobisisobutyronitrile to give a compound of formula followed by deiodination by catalytic hydrogenation. The compound C 7 F 15 CH 2 CH 2 CH 2 N(C 2 H 5 )CH 2 – CH 2 OH is prepared by reaction of C 7 F 15 I with N – allyl – ethylamine and azobisisobutyronitrile to give the compound C 7 F 15 CH 2 CHI CH 2 NHC 2 H 5 , deiodination of this by catalytic hydrogenation to give the compound C 7 F 15 – CH 2 CH 2 CH 2 CH 2 NHC 2 H 5 , and reaction of this with ethylene oxide. The compound C 7 F 15 CH 2 CH(CH 3 )OH is prepared by reaction of C 7 F 15 I, allyl alcohol and azobisisobutyronitrile to give the compound C 7 F 15 CH 2 CHI CH 2 OH, followed by catalytic hydrogenation. The compound C 8 F 17 CH 2 CH 2 SO 2 CH 2 CH 2 OH is prepared by reaction of C 8 F 17 CH 2 CH 2 I with thiourea to give the compound C 8 F 17 CH 2 CH 2 – SH, reacting this with sodium and 2-chloroethanol to give the compound C 8 F 17 CH 2 CH 2 – SCH 2 CH 2 OH, and oxidizing this with hydrogen peroxide. The compound C 8 F 17 CH 2 CHICH 2 OCONH 2 is prepared by reaction of C 8 F 17 I, allyl carbamate and azobisisobutyronitrile.
GB1231946D
1969-03-20
1969-03-20
Expired
GB1231946A
(en)
Applications Claiming Priority (5)
Application Number
Priority Date
Filing Date
Title
GB1465469
1969-03-20
NL6904450A
NL6904450A
(en)
1969-03-20
1969-03-21
FR6908465A
FR2034379A1
(en)
1969-03-20
1969-03-21
CH486669
1969-03-31
BE730819
1969-03-31
Publications (1)
Publication Number
Publication Date
GB1231946A
true
GB1231946A
(en)
1971-05-12
Family
ID=27507710
Family Applications (1)
Application Number
Title
Priority Date
Filing Date
GB1231946D
Expired
GB1231946A
(en)
1969-03-20
1969-03-20
Country Status (5)
Country
Link
BE
(1)
BE730819A
(en)
CH
(2)
CH520813A
(en)
FR
(1)
FR2034379A1
(en)
GB
(1)
GB1231946A
(en)
NL
(1)
NL6904450A
(en)
Cited By (3)
* Cited by examiner, † Cited by third party
Publication number
Priority date
Publication date
Assignee
Title
EP0048368A2
(en)
*
1980-09-18
1982-03-31
Bayer Ag
Process for the preparation of N- and O-substituted mono- or bis-urethanes
US5866711A
(en)
*
1996-09-13
1999-02-02
E. I. Du Pont De Nemours And Company
Fluorocyanate and fluorocarbamate monomers and polymers thereof
US8754190B2
(en)
2010-05-05
2014-06-17
Prolynx Llc
Controlled release from macromolecular conjugates
Families Citing this family (6)
* Cited by examiner, † Cited by third party
Publication number
Priority date
Publication date
Assignee
Title
GB1415412A
(en)
*
1972-09-15
1975-11-26
Ciba Geigy Ag
Perfluoroalkyl compounds process for their manufacture and their use
FR2516920B1
(en)
*
1981-11-25
1986-03-14
Inst Nat Rech Chimique
NOVEL PERFLUORINATED CHAIN COMPOUNDS, THEIR APPLICATION IN PARTICULAR AS INDUSTRIAL AND / OR BIOLOGICAL CONVEYORS OF DISSOLVED GASES AND THEIR PROCESS FOR OBTAINING SAME
FR2588555B1
(en)
*
1985-10-16
1987-12-11
Atochem
FLUORINATED ACRYLIC MONOMERS, DERIVATIVE POLYMERS THEREOF, AND THEIR APPLICATION TO WATER-REPELLENT AND WATER-REPELLENT TREATMENT OF VARIOUS SUBSTRATES
FR2590895B1
(en)
*
1985-12-03
1988-01-15
Atochem
FLUORINATED ACRYLIC MONOMERS, DERIVATIVE POLYMERS AND THEIR APPLICATION AS HYDROPHOBIC AND OLEOPHOBIC AGENTS
US5144056A
(en)
*
1985-12-03
1992-09-01
Atochem
Fluorinated acrylic monomers as hydrophobic and oleophobic agents
US6537662B1
(en)
1999-01-11
2003-03-25
3M Innovative Properties Company
Soil-resistant spin finish compositions
1969
1969-03-20
GB
GB1231946D
patent/GB1231946A/en
not_active
Expired
1969-03-21
FR
FR6908465A
patent/FR2034379A1/fr
not_active
Withdrawn
1969-03-21
NL
NL6904450A
patent/NL6904450A/xx
unknown
1969-03-31
CH
CH520813D
patent/CH520813A/en
not_active
IP Right Cessation
1969-03-31
CH
CH486669D
patent/CH486669A4/xx
unknown
1969-03-31
BE
BE730819D
patent/BE730819A/xx
unknown
Cited By (5)
* Cited by examiner, † Cited by third party
Publication number
Priority date
Publication date
Assignee
Title
EP0048368A2
(en)
*
1980-09-18
1982-03-31
Bayer Ag
Process for the preparation of N- and O-substituted mono- or bis-urethanes
EP0048368A3
(en)
*
1980-09-18
1982-05-12
Bayer Ag
Process for the preparation of n- and o-substituted mono- or bis-urethanes and their use as starting materials in the preparation of aliphatic isocyanates
US5866711A
(en)
*
1996-09-13
1999-02-02
E. I. Du Pont De Nemours And Company
Fluorocyanate and fluorocarbamate monomers and polymers thereof
US8754190B2
(en)
2010-05-05
2014-06-17
Prolynx Llc
Controlled release from macromolecular conjugates
JP2016145234A
(en)
*
2010-05-05
2016-08-12
プロリンクス リミテッド ライアビリティ カンパニー
Controlled release from macromolecular conjugates
Also Published As
Publication number
Publication date
FR2034379A1
(en)
1970-12-11
BE730819A
(en)
1969-09-01
CH486669A4
(en)
1971-12-15
CH520813A
(en)
1972-03-31
NL6904450A
(en)
1970-09-23
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Legal Events
Date
Code
Title
Description
1971-09-22
PS
Patent sealed
1974-10-16
PLNP
Patent lapsed through nonpayment of renewal fees
