GB979142A - Polyethers - Google Patents

Polyethers

Info

Publication number
GB979142A
GB979142A GB9989/62A GB998962A GB979142A GB 979142 A GB979142 A GB 979142A GB 9989/62 A GB9989/62 A GB 9989/62A GB 998962 A GB998962 A GB 998962A GB 979142 A GB979142 A GB 979142A
Authority
GB
United Kingdom
Prior art keywords
hydrogen
chr
ammonia
compounds
primary
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
GB9989/62A
Inventor
Dennis Charlton Allport
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.)
Imperial Chemical Industries Ltd
Original Assignee
Imperial Chemical Industries Ltd
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 Imperial Chemical Industries Ltd filed Critical Imperial Chemical Industries Ltd
Priority to GB10591/63A priority Critical patent/GB984510A/en
Priority to GB9989/62A priority patent/GB979142A/en
Publication of GB979142A publication Critical patent/GB979142A/en
Expired 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
    • 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
    • C08G18/5021—Polyethers having heteroatoms other than oxygen having nitrogen
    • C08G18/5024—Polyethers having heteroatoms other than oxygen having nitrogen containing primary and/or secondary amino groups
    • 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
    • C08G65/32—Polymers modified by chemical after-treatment
    • C08G65/321—Polymers modified by chemical after-treatment with inorganic compounds
    • C08G65/322—Polymers modified by chemical after-treatment with inorganic compounds containing hydrogen
    • 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
    • C08G65/32—Polymers modified by chemical after-treatment
    • C08G65/321—Polymers modified by chemical after-treatment with inorganic compounds
    • C08G65/325—Polymers modified by chemical after-treatment with inorganic compounds containing nitrogen
    • C08G65/3255—Ammonia
    • 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
    • C08G65/32—Polymers modified by chemical after-treatment
    • C08G65/329—Polymers modified by chemical after-treatment with organic compounds
    • C08G65/333—Polymers modified by chemical after-treatment with organic compounds containing nitrogen
    • C08G65/33365—Polymers modified by chemical after-treatment with organic compounds containing nitrogen containing cyano group
    • C08G65/33368—Polymers modified by chemical after-treatment with organic compounds containing nitrogen containing cyano group acyclic
    • C08G65/33372—Polymers modified by chemical after-treatment with organic compounds containing nitrogen containing cyano group acyclic acrylonitrile
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Inorganic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Compounds having polyether chains terminated by primary or secondary amine groups are prepared by the reductive amination of the corresponding ketonic compounds X-[-(CHR-CHR-O)m-(CHR-CHR1-O-)n-CHR-COR1]a where R is hydrogen or a hydrocarbon group, R1 is a hydrocarbon group, n is at least one, and m is zero or an integer, and X is the residue of a compound XHa containing 2 hydrogen atoms reactive towards cyclic oxides. The reductive amination involves the simultaneous treatment of the ketonic polyether with ammonia or a primary amine and a ketone-reducing agent, such as sodium amalgam, formic acid or zinc/acetic acid, or, in particular, hydrogen with a catalyst. The preferred catalyst is Raney nickel, but Raney cobalt, or cobalt on kieselguhr may be used. When hydrogen is used temperatures of 40-150 DEG and pressures of 50-250 atmospheres are preferred. Excess of ammonia or amine is used in order to minimize chain linkage by amine groups. Suitable amines include aliphatic, alicyclic, aromatic and heterocyclic primary amines and polyamines, e.g. methylamine, ethanolamine, tolylene diamine. The examples describe the reactions of a ketone ended polypropylene oxide of molecular weight about 1,000 with ammonia, and with ethanolamine under hydrogen in the presence of Raney nickel. Specification 971,173 is referred to.ALSO:Compounds having polyether chains terminated by primary or secondary amine groups are prepared by the reductive amination of the corresponding ketonic compounds X-[-(CHR-CHR-O)m-(CHR-CHR1-O)n-CHR-COR1]a where R is hydrogen or a hydrocarbon group, R1 a hydrocarbon group, n is at least one, and m is zero or an integer, and X is the residue of a compound XHa containing 2 hydrogen atoms reactive towards cyclic oxides. These compounds may be prepared as described in Specification 971,173. The reductive amination involves the simultaneous treatment of the ketonic compound with ammonia or a primary amine and a ketone-reducing agent, such as sodium amalgan, formic acid or zinc/acetic acid, or, preferably, hydrogen with a catalyst, particularly Raney nickel, though e.g. Raney cobalt, or cobalt on kieselguhr may be used. When hydrogen is used temperatures of 40-150 DEG C. and pressures of 50-250 atmospheres are preferred. Excess of ammonia or amine is used in order to minimise chain linkage by amine groups, and suitable amines include aliphatic, alicyclic, aromatic and heterocyclic primary amines and polyamines, e.g. methylamine, ethanolamine, tolylene diamine. The examples describe the reactions of a ketone-ended polypropylene oxide of molecular weight about 1,000 with ammonia and ethanolamine under hydrogen in the presence of Raney nickel.
GB9989/62A 1962-03-15 1962-03-15 Polyethers Expired GB979142A (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
GB10591/63A GB984510A (en) 1962-03-15 1962-03-15 New polyethers
GB9989/62A GB979142A (en) 1962-03-15 1962-03-15 Polyethers

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB10591/63A GB984510A (en) 1962-03-15 1962-03-15 New polyethers
GB9989/62A GB979142A (en) 1962-03-15 1962-03-15 Polyethers

Publications (1)

Publication Number Publication Date
GB979142A true GB979142A (en) 1965-01-01

Family

ID=62527863

Family Applications (2)

Application Number Title Priority Date Filing Date
GB9989/62A Expired GB979142A (en) 1962-03-15 1962-03-15 Polyethers
GB10591/63A Expired GB984510A (en) 1962-03-15 1962-03-15 New polyethers

Family Applications After (1)

Application Number Title Priority Date Filing Date
GB10591/63A Expired GB984510A (en) 1962-03-15 1962-03-15 New polyethers

Country Status (1)

Country Link
GB (2) GB979142A (en)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3446819A (en) * 1966-06-14 1969-05-27 Olin Mathieson 3-alkenoxyoxetanes
JPS59124922A (en) * 1982-12-31 1984-07-19 Nippon Paint Co Ltd Resin for dispersing pigment
WO1997030103A2 (en) * 1996-02-15 1997-08-21 The Dow Chemical Company Preparation of polyetheramines and polyetheramine derivatives

Also Published As

Publication number Publication date
GB984510A (en) 1965-02-24

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