CA2100218A1 - Preparation and polymerization of perfluoroalkoxy alkylene oxides to prepare hydrophobic polyethers - Google Patents

Preparation and polymerization of perfluoroalkoxy alkylene oxides to prepare hydrophobic polyethers

Info

Publication number
CA2100218A1
CA2100218A1 CA 2100218 CA2100218A CA2100218A1 CA 2100218 A1 CA2100218 A1 CA 2100218A1 CA 2100218 CA2100218 CA 2100218 CA 2100218 A CA2100218 A CA 2100218A CA 2100218 A1 CA2100218 A1 CA 2100218A1
Authority
CA
Canada
Prior art keywords
carbons
oxetane
monomers
perfluorinated
alkyl
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.)
Granted
Application number
CA 2100218
Other languages
French (fr)
Other versions
CA2100218C (en
Inventor
Aslam Malik
Gerald E. Manser
Thomas G. Archibald
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Aerojet Fine Chemicals LLC
Original Assignee
Aslam Malik
Gerald E. Manser
Thomas G. Archibald
Aerojet-General Corporation
Ampac Fine Chemicals Llc
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
Publication date
Application filed by Aslam Malik, Gerald E. Manser, Thomas G. Archibald, Aerojet-General Corporation, Ampac Fine Chemicals Llc filed Critical Aslam Malik
Publication of CA2100218A1 publication Critical patent/CA2100218A1/en
Application granted granted Critical
Publication of CA2100218C publication Critical patent/CA2100218C/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/04—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers only
    • C08G65/22—Cyclic ethers having at least one atom other than carbon and hydrogen outside the ring
    • C08G65/223—Cyclic ethers having at least one atom other than carbon and hydrogen outside the ring containing halogens
    • C08G65/226—Cyclic ethers having at least one atom other than carbon and hydrogen outside the ring containing halogens containing fluorine
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D305/00—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms
    • C07D305/02—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms not condensed with other rings
    • C07D305/04—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D305/06—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring atoms
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/08—Processes
    • C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40—High-molecular-weight compounds
    • C08G18/48—Polyethers
    • C08G18/50—Polyethers having heteroatoms other than oxygen
    • C08G18/5003—Polyethers having heteroatoms other than oxygen having halogens
    • C08G18/5015—Polyethers having heteroatoms other than oxygen having halogens having fluorine atoms
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/04—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers only
    • C08G65/06—Cyclic ethers having no atoms other than carbon and hydrogen outside the ring
    • C08G65/16—Cyclic ethers having four or more ring atoms
    • C08G65/18—Oxetanes
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/04—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers only
    • C08G65/06—Cyclic ethers having no atoms other than carbon and hydrogen outside the ring
    • C08G65/16—Cyclic ethers having four or more ring atoms
    • C08G65/20—Tetrahydrofuran

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Polyethers (AREA)
  • Epoxy Compounds (AREA)

Abstract

Oxetane monomers having perfluorinated alkoxy side chains; a method for their preparation; a method for their polymerization; and the resultant prepolymers are disclosed. The monomers have the formula: wherein n is 1 to 5, m is 1, R is hydrogen or alkyl having from 1 to 4 carbons; and R f is linear or branched chain perfluorinated alkyl having from 1 to 20 carbons, or an oxaperfluorinated polyether, having from 4 to about 60 carbons, and the resultant prepolymers have the formula:
CA 2100218 1992-07-10 1993-07-09 Preparation and polymerization of perfluoroalkoxy alkylene oxides to prepare hydrophobic polyethers Expired - Lifetime CA2100218C (en)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US911,461 1978-06-01
US91146192A 1992-07-10 1992-07-10
US8061493A 1993-06-21 1993-06-21
US080,614 1993-06-21

Publications (2)

Publication Number Publication Date
CA2100218A1 true CA2100218A1 (en) 1994-01-11
CA2100218C CA2100218C (en) 2007-11-27

Family

ID=26763720

Family Applications (1)

Application Number Title Priority Date Filing Date
CA 2100218 Expired - Lifetime CA2100218C (en) 1992-07-10 1993-07-09 Preparation and polymerization of perfluoroalkoxy alkylene oxides to prepare hydrophobic polyethers

Country Status (5)

Country Link
JP (1) JP3335427B2 (en)
CA (1) CA2100218C (en)
DE (1) DE4323307B4 (en)
FR (1) FR2694297B1 (en)
GB (1) GB2269816B (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5543200A (en) * 1994-12-19 1996-08-06 Gencorp Inc. Abrasion-resistant article coated with a coating compositions based on fluorinated monohydric alcohol
US5674951A (en) * 1994-05-20 1997-10-07 Gencorp Inc. Abrasion-resistant and low friction coating compositions

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5807977A (en) 1992-07-10 1998-09-15 Aerojet General Corporation Polymers and prepolymers from mono-substituted fluorinated oxetane monomers
CA2379371A1 (en) * 1999-07-16 2001-01-25 Aerojet-General Corporation Amorphous polyether glycols based on bis-substituted oxetane monomers
JP2001278874A (en) * 2000-03-31 2001-10-10 Daikin Ind Ltd Fluorinated oxetane derivative and method for producing the same
JP2001278875A (en) * 2000-03-31 2001-10-10 Daikin Ind Ltd Method for producing 3-fluoroalkoxymethyl-3- alkyloxetane
US7649030B2 (en) * 2007-01-25 2010-01-19 Hewlett-Packard Development Company, L.P. Polyurethane with fluoro-diols suitable for ink-jet printing
CN106187953B (en) * 2016-07-29 2018-06-29 湖北固润科技股份有限公司 A kind of cationic polymerization monomer and synthesis and application

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1495627A1 (en) * 1960-03-31 1970-03-19 Hoechst Ag Linear polyaethers made from oxacyclobutane derivatives which are disubstituted in the 3-position by halogen-containing groups, and processes for their preparation
SU523910A1 (en) * 1975-01-08 1976-08-05 Пермский политехнический институт Polymer 3,3-bis- (trihydrotetrafluoropropoxymethylene) -oxacyclobutane to produce modified polyurethanes
US4764586A (en) * 1986-10-29 1988-08-16 Morton Thiokol, Inc. Internally-plasticized polyethers from substituted oxetanes
US4898981A (en) * 1988-06-20 1990-02-06 Ciba-Geigy Corporation Heteroatom containing perfluoroalkyl terminated neopentyl glycols and compositions therefrom
US4988797B1 (en) * 1989-03-14 1993-12-28 Cationic polymerization of cyclic ethers
US5097048A (en) * 1989-11-30 1992-03-17 Ciba-Geigy Corporation Heteroatom containing 3,3-bis-perfluoroalkyl oxetanes and polyethers therefrom
US5097067A (en) * 1989-11-30 1992-03-17 Ciba-Geigy Corporation Carboxy acids derived from heteroatom containing 3,3-bis-perfluoroalkyl oxetanes

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5674951A (en) * 1994-05-20 1997-10-07 Gencorp Inc. Abrasion-resistant and low friction coating compositions
US5543200A (en) * 1994-12-19 1996-08-06 Gencorp Inc. Abrasion-resistant article coated with a coating compositions based on fluorinated monohydric alcohol

Also Published As

Publication number Publication date
DE4323307B4 (en) 2012-10-31
GB2269816B (en) 1996-10-30
CA2100218C (en) 2007-11-27
GB9314107D0 (en) 1993-08-18
DE4323307A1 (en) 1994-01-27
FR2694297B1 (en) 1995-07-07
FR2694297A1 (en) 1994-02-04
GB2269816A (en) 1994-02-23
JP3335427B2 (en) 2002-10-15
JPH06263867A (en) 1994-09-20

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