GB928112A - Condensation products - Google Patents

Condensation products

Info

Publication number
GB928112A
GB928112A GB1740260A GB1740260A GB928112A GB 928112 A GB928112 A GB 928112A GB 1740260 A GB1740260 A GB 1740260A GB 1740260 A GB1740260 A GB 1740260A GB 928112 A GB928112 A GB 928112A
Authority
GB
Grant status
Application
Patent type
Prior art keywords
aldehyde
polyamine
condensates
reaction
amino groups
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
GB1740260A
Inventor
John Earnshaw
Gwilym Thomas Jones
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

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G12/00Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen
    • C08G12/02Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes
    • C08G12/04Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with acyclic or carbocyclic compounds
    • C08G12/06Amines
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G12/00Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen
    • C08G12/46Block or graft polymers prepared by polycondensation of aldehydes or ketones on to macromolecular compounds
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G65/00Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/32Polymers modified by chemical after-treatment
    • C08G65/321Polymers modified by chemical after-treatment with inorganic compounds
    • C08G65/325Polymers modified by chemical after-treatment with inorganic compounds containing nitrogen
    • C08G65/3255Ammonia
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06MTREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS, OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M15/00Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/19Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
    • D06M15/37Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/39Aldehyde resins; Ketone resins; Polyacetals
    • D06M15/423Amino-aldehyde resins

Abstract

The invention comprises condensation products of an aliphatic aldehyde having not more than 6 carbon atoms and a polyalkenoxy polyamine which contains at least 2 terminal primary amino groups and varying amounts of secondary and tertiary amino groups and which is obtained from an alkylene oxide condensate having a molecular weight of 200 to 6,000. Specified aldehydes are formaldehyde, acetaldehyde, propionaldehyde, butyraldehyde, pyruvic aldehyde, acrolein, crotonaldehyde, furfural and glyoxal. Condensates suitable for conversion to polyamines include polyethylene glycols, and condensates of ethylene oxide with polyhydroxy compounds such as glycerol, sorbitol and pentaerythritol, amines such as methyl-, ethyl-and cetyl-amine, and amides. Conversion may be effected by chlorination, e.g. with thionyl chloride, followed by reaction with ammonia, or by reacting with acrylonitrile followed by hydrogenation. Reaction with the aldehyde is effected in aqueous or other solution and the polyamine may be partially neutralized with an acid. There is preferably one aldehyde group present for each primary and secondary amine group. A water-soluble pre-condensate may be obtained by using mild conditions or an excess of polyamine; further reaction under stronger conditions or with more aldehyde, optionally in the presence of an acidic catalyst, e.g. zinc nitrate or ammonium thiocyanate, yields an insoluble resin. The products may be applied in this way to textile materials, either alone or with other resins such as urea- or melamine-formaldehyde.ALSO:The invention comprises condensation products of an aliphatic aldehyde having not more than 6 carbon atoms and a polyalkenoxy polyamine which contains at least 2 terminal primary amino groups and varying amounts of secondary and tertiary amino groups and which is obtained from an alkylene oxide condensate having a molecular weight of 200 to 6,000. Specified aldehydes are formaldehyde, acetaldehyde, propionaldehyde, butyraldehyde, pyruvic aldehyde, acrolein, crotonaldehyde, furfural and glyoxal. Condensates suitable for conversion to polyamines include polyethylene glycols, and condensates of ethylene oxide with polyhydroxy compounds such as glycerol, sorbitol and pentaerythritol, amines such as methyl-, ethyl- and cetylamine, and amides. Conversion may be effected by chlorination, e.g. with thionyl chloride, followed by reaction with ammonia, or by reaction with acrylonitrile followed by hydrogenation. Reaction with the aldehyde is effected in aqueous or other solution and the polyamine may be partially neutralised with an acid. There is preferably one aldehyde group present for each primary and secondary amine group. A water-soluble precondensate may be obtained by using mild conditions or an excess of polyamine; further reaction under stronger conditions or with more aldehyde, optionally in the presence of an acidic catalyst, e.g. zinc nitrate or ammonium thiocyanate, yields an insoluble resin. The products may be applied in this way to textile materials (see Group IV(c)).ALSO:A process for treating textile materials, particularly to provide anti-static properties on hydrophobic fibres such as polyacrylonitrile, polyamides and polyesters, comprises applying thereto a water-soluble pre-condensate of an aliphatic aldehyde having not more than 6 carbon atoms and a polyalkenoxy polyamine which contains at least 2 terminal primary amino groups and which is obtained from an alkylene oxide condensate having a molecular weight of 200 to 6,000. Specified aldehydes are formaldehyde, acetaldehyde, pripionaldehyde, butyraldehyde, pyruvic aldehyde, acrolein, crotonaldehyde, furfural and glyoxal. Suitable condensates from which the polyamines may be derived are polyethylene glycols, and condensates of ethylene oxide with polyhydroxy compounds such as glycerol, sorbitol and pentaerythritol, amines such as methyl-, ethyland cetyl-amine, and amides. The aldehyde precondensate may be applied in aqueous or aqueous-alcohol solution which may also contain other resin finishes such as urea- or melamineformaldehyde. A catalyst such as zinc nitrate or ammonium thiocyanate may be added to the bath. The treated textile is dried and baked at temperatures of 100 DEG -210 DEG C. The increase in dry weight is usually 0,1 to 5%.
GB1740260A 1960-05-17 1960-05-17 Condensation products Expired GB928112A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB1740260A GB928112A (en) 1960-05-17 1960-05-17 Condensation products

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB1740260A GB928112A (en) 1960-05-17 1960-05-17 Condensation products

Publications (1)

Publication Number Publication Date
GB928112A true true GB928112A (en) 1963-06-06

Family

ID=10094563

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1740260A Expired GB928112A (en) 1960-05-17 1960-05-17 Condensation products

Country Status (1)

Country Link
GB (1) GB928112A (en)

Cited By (28)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2001098388A1 (en) * 2000-06-23 2001-12-27 Basf Aktiengesellschaft Polymeric aldehyde/polyetheramine networks
US9120897B1 (en) 2014-05-27 2015-09-01 International Business Machines Corporation Preparation of thioether polymers
US9120899B1 (en) 2014-06-02 2015-09-01 International Business Machines Corporation Preparation of functional polysulfones
US9228034B1 (en) 2014-10-09 2016-01-05 International Business Machines Corporation Hexahydrotriazine, dithiazine, and thioether functionalized materials
US9243107B2 (en) 2013-10-10 2016-01-26 International Business Machines Corporation Methods of preparing polyhemiaminals and polyhexahydrotriazines
US9255172B1 (en) 2014-08-05 2016-02-09 International Business Machines Corporation High-performance, filler-reinforced, recyclable composite materials
US9271498B2 (en) 2014-06-19 2016-03-01 International Business Machines Corporation Antimicrobial PHT coatings
US9296863B2 (en) 2014-06-16 2016-03-29 International Business Machines Corporation Preparation of poly(octatriazacane)
US9303186B1 (en) 2014-10-16 2016-04-05 International Business Machines Corporation PHT powder coating materials
US9352045B2 (en) 2014-06-20 2016-05-31 International Business Machines Corporation Methods and materials for therapeutic delivery
US9389181B2 (en) 2014-06-06 2016-07-12 International Business Machines Corporation Methods and apparatus for detecting metals in liquids
US9453108B2 (en) 2014-08-22 2016-09-27 International Business Machines Corporation Flame retardant PHT compositions
US9469660B2 (en) 2014-06-03 2016-10-18 International Business Machines Corporation Sulfur scavenging materials comprising hexahydrotriazine-modified particle
US9512332B2 (en) 2014-06-27 2016-12-06 International Busuiness Machines Corporation Soluble, processable polyhemiaminals and polyhexahydrotriazines
US9522977B2 (en) 2014-07-24 2016-12-20 International Business Machines Corporation Thermoplastic toughening of PHT's
US9592470B2 (en) 2014-05-27 2017-03-14 International Business Machines Corporation Sulfur scavenging materials for filters and coatings
US9656239B2 (en) 2014-06-16 2017-05-23 International Business Machines Corporation Apparatus for controlling metals in liquids
US9676891B2 (en) 2014-08-22 2017-06-13 International Business Machines Corporation Synthesis of dynamic covalent 3D constructs
US9758620B2 (en) 2015-09-03 2017-09-12 International Business Machines Corporation Tailorable viscoelastic properties of PEG-hemiaminal organogel networks
US9765188B2 (en) 2015-11-02 2017-09-19 International Business Machines Corporation High molecular weight polythioaminals from a single monomer
US9777116B2 (en) 2014-10-16 2017-10-03 International Business Machines Corporation Porous/nanoporous PHT
US9873766B2 (en) 2015-11-24 2018-01-23 International Business Machines Corporation Systems chemistry approach to polyhexahydrotriazine polymeric structures
US9879118B2 (en) 2015-10-05 2018-01-30 International Business Machines Corporation Polymers from stabilized imines
US9957345B2 (en) 2014-08-18 2018-05-01 International Business Machines Corporation 3D printing with PHT based materials
US10006936B2 (en) 2015-11-30 2018-06-26 International Business Machines Corporation Poly(thioaminal) probe based lithography
US10023735B2 (en) 2014-08-18 2018-07-17 International Business Machines Corporation 3D printing with PHT/PHA based materials and polymerizable monomers
US10080806B2 (en) 2015-08-19 2018-09-25 International Business Machines Corporation Sulfur-containing polymers from hexahydrotriazine and dithiol precursors as a carrier for active agents
US10113034B2 (en) 2016-10-25 2018-10-30 International Business Machines Corporation Polymers from stabilized imines

Cited By (51)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2001098388A1 (en) * 2000-06-23 2001-12-27 Basf Aktiengesellschaft Polymeric aldehyde/polyetheramine networks
US9951184B2 (en) 2013-10-10 2018-04-24 International Business Machines Corporation Methods of preparing polyhemiaminals and polyhexahydrotriazines
US9243107B2 (en) 2013-10-10 2016-01-26 International Business Machines Corporation Methods of preparing polyhemiaminals and polyhexahydrotriazines
US9120897B1 (en) 2014-05-27 2015-09-01 International Business Machines Corporation Preparation of thioether polymers
US9592470B2 (en) 2014-05-27 2017-03-14 International Business Machines Corporation Sulfur scavenging materials for filters and coatings
US9228059B2 (en) 2014-05-27 2016-01-05 International Business Machines Corporation Preparation of thioether polymers
US9610535B2 (en) 2014-05-27 2017-04-04 International Business Machines Corporation Sulfur scavenging materials for filters and coatings
US9388281B2 (en) 2014-05-27 2016-07-12 International Business Machines Corporation Preparation of thioether polymers
US9206289B1 (en) 2014-06-02 2015-12-08 International Business Machines Corporation Preparation of functional polysulfones
US9139698B1 (en) 2014-06-02 2015-09-22 International Business Machines Corporation Preparation of functional polysulfones
US9120899B1 (en) 2014-06-02 2015-09-01 International Business Machines Corporation Preparation of functional polysulfones
US9469660B2 (en) 2014-06-03 2016-10-18 International Business Machines Corporation Sulfur scavenging materials comprising hexahydrotriazine-modified particle
US9389181B2 (en) 2014-06-06 2016-07-12 International Business Machines Corporation Methods and apparatus for detecting metals in liquids
US9599560B2 (en) 2014-06-06 2017-03-21 International Business Machines Corporation Methods and apparatus for detecting metals in liquids
US9656239B2 (en) 2014-06-16 2017-05-23 International Business Machines Corporation Apparatus for controlling metals in liquids
US9296863B2 (en) 2014-06-16 2016-03-29 International Business Machines Corporation Preparation of poly(octatriazacane)
US9770702B2 (en) 2014-06-16 2017-09-26 International Business Machines Corporation Methods and apparatus for controlling metals in liquids
US9296862B2 (en) 2014-06-16 2016-03-29 International Business Machines Corporation Preparation of poly(octatriazacane)
US10015970B2 (en) 2014-06-19 2018-07-10 International Business Machines Corporation Antimicrobial PHT coatings
US9271498B2 (en) 2014-06-19 2016-03-01 International Business Machines Corporation Antimicrobial PHT coatings
US9931409B2 (en) 2014-06-20 2018-04-03 International Business Machines Corporation Methods and materials for therapeutic delivery
US10071161B2 (en) 2014-06-20 2018-09-11 International Business Machines Corporation Methods and materials for therapeutic delivery
US9352045B2 (en) 2014-06-20 2016-05-31 International Business Machines Corporation Methods and materials for therapeutic delivery
US9512332B2 (en) 2014-06-27 2016-12-06 International Busuiness Machines Corporation Soluble, processable polyhemiaminals and polyhexahydrotriazines
US9598608B2 (en) 2014-06-27 2017-03-21 International Business Machines Corporation Soluble, processable polyhemiaminals and polyhexahydrotriazines
US9522977B2 (en) 2014-07-24 2016-12-20 International Business Machines Corporation Thermoplastic toughening of PHT's
US9587073B2 (en) 2014-07-24 2017-03-07 International Business Machines Corporation Thermoplastic toughening of PHT's
US9586824B2 (en) 2014-08-05 2017-03-07 International Business Machines Corporation High-performance, filler-reinforced, recyclable composite materials
US9598284B2 (en) 2014-08-05 2017-03-21 International Business Machines Corporation High-performance, filler-reinforced, recyclable composite materials
US9255172B1 (en) 2014-08-05 2016-02-09 International Business Machines Corporation High-performance, filler-reinforced, recyclable composite materials
US9403945B2 (en) 2014-08-05 2016-08-02 International Business Machines Corporation High-performance, filler-reinforced, recyclable composite materials
US9695282B2 (en) 2014-08-05 2017-07-04 International Business Machines Corporation High-performance, filler-reinforced, recyclable composite materials
US10023735B2 (en) 2014-08-18 2018-07-17 International Business Machines Corporation 3D printing with PHT/PHA based materials and polymerizable monomers
US9957345B2 (en) 2014-08-18 2018-05-01 International Business Machines Corporation 3D printing with PHT based materials
US9809673B2 (en) 2014-08-22 2017-11-07 International Business Machines Corporation Synthesis of dynamic covalent 3D constructs
US10035882B2 (en) 2014-08-22 2018-07-31 International Business Machines Corporation Flame retardant PHT compositions
US9453108B2 (en) 2014-08-22 2016-09-27 International Business Machines Corporation Flame retardant PHT compositions
US9676891B2 (en) 2014-08-22 2017-06-13 International Business Machines Corporation Synthesis of dynamic covalent 3D constructs
US9422378B2 (en) 2014-10-09 2016-08-23 International Business Machines Corporation Hexahydrotriazine, dithiazine, and thioether functionalized materials
US9228034B1 (en) 2014-10-09 2016-01-05 International Business Machines Corporation Hexahydrotriazine, dithiazine, and thioether functionalized materials
US9890248B2 (en) 2014-10-16 2018-02-13 International Business Machines Corporation Porous/nanoporous PHT
US9777116B2 (en) 2014-10-16 2017-10-03 International Business Machines Corporation Porous/nanoporous PHT
US9644065B2 (en) 2014-10-16 2017-05-09 International Business Machines Corporation PHT powder coating materials
US9303186B1 (en) 2014-10-16 2016-04-05 International Business Machines Corporation PHT powder coating materials
US10080806B2 (en) 2015-08-19 2018-09-25 International Business Machines Corporation Sulfur-containing polymers from hexahydrotriazine and dithiol precursors as a carrier for active agents
US9758620B2 (en) 2015-09-03 2017-09-12 International Business Machines Corporation Tailorable viscoelastic properties of PEG-hemiaminal organogel networks
US9879118B2 (en) 2015-10-05 2018-01-30 International Business Machines Corporation Polymers from stabilized imines
US9765188B2 (en) 2015-11-02 2017-09-19 International Business Machines Corporation High molecular weight polythioaminals from a single monomer
US9873766B2 (en) 2015-11-24 2018-01-23 International Business Machines Corporation Systems chemistry approach to polyhexahydrotriazine polymeric structures
US10006936B2 (en) 2015-11-30 2018-06-26 International Business Machines Corporation Poly(thioaminal) probe based lithography
US10113034B2 (en) 2016-10-25 2018-10-30 International Business Machines Corporation Polymers from stabilized imines

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