GB1231946A - - Google Patents

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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
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GB
United Kingdom
Prior art keywords
compound
reaction
give
prepared
group
Prior art date
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.)
Filing date
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Publication of GB1231946A publication Critical patent/GB1231946A/en
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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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

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

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
CH486669A4 (en) 1971-12-15
CH520813A (en) 1972-03-31
NL6904450A (en) 1970-09-23
FR2034379A1 (en) 1970-12-11
BE730819A (en) 1969-09-01

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Legal Events

Date Code Title Description
PS Patent sealed
PLNP Patent lapsed through nonpayment of renewal fees