GB579340A - Use of polyester-amide compositions for coating, impregnating, adhesive or like purposes - Google Patents

Use of polyester-amide compositions for coating, impregnating, adhesive or like purposes

Info

Publication number
GB579340A
GB579340A GB2034543A GB2034543A GB579340A GB 579340 A GB579340 A GB 579340A GB 2034543 A GB2034543 A GB 2034543A GB 2034543 A GB2034543 A GB 2034543A GB 579340 A GB579340 A GB 579340A
Authority
GB
United Kingdom
Prior art keywords
diisocyanate
benzene
polyesteramide
solution
phenylene
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
GB2034543A
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
Publication of GB579340A publication Critical patent/GB579340A/en
Expired legal-status Critical Current

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
    • C08G18/00Polymeric products of isocyanates or isothiocyanates
    • C08G18/06Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40High-molecular-weight compounds
    • C08G18/60Polyamides or polyester-amides
    • C08G18/606Polyester-amides
    • 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
    • D06M15/564Polyureas, polyurethanes or other polymers having ureide or urethane links; Precondensation products forming them
    • DTEXTILES; PAPER
    • D21PAPER-MAKING; PRODUCTION OF CELLULOSE
    • D21HPULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
    • D21H17/00Non-fibrous material added to the pulp, characterised by its constitution; Paper-impregnating material characterised by its constitution
    • D21H17/20Macromolecular organic compounds
    • D21H17/33Synthetic macromolecular compounds
    • D21H17/46Synthetic macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • D21H17/54Synthetic macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen
    • D21H17/55Polyamides; Polyaminoamides; Polyester-amides

Landscapes

  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Paints Or Removers (AREA)
  • Polyurethanes Or Polyureas (AREA)
  • Adhesives Or Adhesive Processes (AREA)

Abstract

Compositions which comprise a solution of a polyesteramide in an organic solvent in admixture with an organic diisocyanate are used under conditions which avoid the use of heat for coating, impregnating, adhesive or like purposes. The polyesteramides may already have been slightly modified by treatment with an organic diisocyanate to a point at which they still retain their solubility in organic solvents. Suitable solvents are acetone, mixtures of benzene and acetone, mixtures of benzene and chloroform, mixtures of benzene and methyl ethyl ketone and mixtures of methyl ethyl ketone with trichlorethylene. Water should be avoided. Suitable diisocyanates are ethylene, trimethylene, tetramethylene, hexamethylene, decamethylene, p-phenylene, m-phenylene, diphenyl-4 : 41, diphenylmethane 4 : 41, naphthalene, and adipyl diisocyanates. Usually not more than 10 per cent of diisocyanate on the weight of polyesteramide is employed. Solution of the polyesteramide in organic solvents may be facilitated by mechanical working or by thermal degradation. The compositions may include fillers, e.g. carbon black, clay, blanc fixe, whiting, lithopone or mica; natural or synthetic rubber; plasticisers, e.g. tricresyl phosphate, dibutyl phthalate, butylphthalylbutyl glycollate or N - alkyltoluenesulphonamides; stabilisers or antioxidants, e.g. the diphenyl-o-tolylguanidine salt of dicatechol borate, diphenylamine - acetone condensation products and diphenyl-p-phenylene diamine. Pigments may also be included and oil-soluble metallic driers, e.g. lead or cobalt naphthenates. Other materials reactive with the diisocyanate may also be included, e.g. cellulose acetate, cellulose nitrate, cellulose ethers, viscose, casein, zein, soya-protein, polyvinyl alcohol or wood-flour. If desired two separate compositions may be employed, one containing a solution of polyesteramide and the other a diisocyanate with or without a solvent. These may be mixed together immediately or shortly before use or may be applied separately to the surfaces which are then adhesively united together or consecutively to the surface of the article to be coated or impregnated. The compositions may be used for adhesively uniting fabrics, leather, sheets or shaped articles of various material with themselves or with other materials or articles. Granular or fibrous materials, e.g. cork dust, leather dust, wood dust, asbestos, or wool, cotton or other fibres, loose p or in the form of felts may be fabricated with the compositions as binders into sheets or other shapes. Or the compositions may be used in usual manner for coating or impregnating. Suitable reactants for making the polyesteramides are ethylene, diethylene, trimethylene, pentamethylene, hexamethylene, decamethylene or dodecamethyleneglycol, 1 : 12-octadecanediol or pentaglycol; amino alcohols such as ethanolamine and 3-amino-propanol; dibasic carboxylic acids, e.g. malonic, maleic, fumaric, succinic, glutaric, suberic, azelaic, b -methyladipic, adipic, pimelic, sebasic, undecanedioic, brassylic, isophthalic, hexahydroterephthalic, p-phenylenediacetic, dihydrosuccinic, or acetylene dicarboxylic acid; diamines, e.g. ethylenediamine, hexamethylenediamine, 3-methylhexamethylenediamine, decamethylenediamine, or m-phenylenediamine; monohydroxymonocarboxylic acids, e.g. glycollic, 6-hydroxycaproic, 10-hydroxydecanoic, or 12-hydroxystearic acid; and polymerisable monoaminomonocarboxylic acids, e.g. 6-aminocaproic acid, caprolactam, 9-aminononanoic, 11-aminoundecanoic or 12-aminostearic. In the examples: (1) a polyesteramide from adipic acid, ethylene glycol and monoethanolamine is dissolved in a benzene-chloroform mixture, and modified by boiling with hexamethylene diisocyanate. To the resulting solution m-phenylene diisocyanate dissolved in benzene is added. Air-dried films formed from the mixture are no longer soluble in organic solvents. (2) A similarly modified polyesteramide is lightly milled and dissolved in a benzene-acetone mixture and m-phenylene diisocyanate dissolved in the same solvent is added. The composition may be used for making a composite fabric for fuel or oil containers, or if allowed to stand for 2 hours after mixing it forms a slurry which may be used as a slushing composition for fuel containers made from fabrics, leather, felt or vulcanised film or for making coated fabrics. (3) A composition similar to that of example (2) with p-phenylene diisocyanate instead of the m-compound. (6) The composition of example (2) is mixed with its own weight of cork powder and the mixture dried to form tough sheets which may be shaped by hydraulic pressure. (7) The composition of example (2) is diluted with the mixed solvents and leather dust added to form a thick dough which is formed into sheets. (8) A composition is made as in example (2) using hexamethylene diisocyanate in place of the m-phenylene compound. Cobalt or lead naphthenate in white spirit is added and films formed from the thickened solution. Diphenyl 4.41-diisocyanate may replace the m-phenylene diisocyanate. (9) The polyester amide of example (1) is dissolved in benzeneacetone mixture and carbon black added. The dough is spread on fabric, dried, treated with a benzene solution of m-phenylene diisocyanate and again dried. (10) The diisocyanate modified polyesteramide of example (2) is lightly milled and paddled to a smooth solution with a benzene acetone mixture. Diphenylmethane4 41-diisocyanate dissolved in the same mixture is added to form an adhesive. (11) The diisocyanate modified polyesteramide of example (2) is lightly milled and paddled with acetone to give a smooth solution to which is added a solution of nitrocellulose or cellulose acetate in acetone and di-phenylmethane-4 , 41-diisocyanate. Specifications 553,733, 561,104, 561,108 and 574,134 are referred to.
GB2034543A 1946-10-02 1943-12-06 Use of polyester-amide compositions for coating, impregnating, adhesive or like purposes Expired GB579340A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB2306646A GB614991A (en) 1946-10-02 1946-10-02 Use for polyester-amide compositions for coating, impregnating, adhesive or like purposes

Publications (1)

Publication Number Publication Date
GB579340A true GB579340A (en) 1946-07-31

Family

ID=10189566

Family Applications (2)

Application Number Title Priority Date Filing Date
GB2034543A Expired GB579340A (en) 1946-10-02 1943-12-06 Use of polyester-amide compositions for coating, impregnating, adhesive or like purposes
GB2306646A Expired GB614991A (en) 1946-10-02 1946-10-02 Use for polyester-amide compositions for coating, impregnating, adhesive or like purposes

Family Applications After (1)

Application Number Title Priority Date Filing Date
GB2306646A Expired GB614991A (en) 1946-10-02 1946-10-02 Use for polyester-amide compositions for coating, impregnating, adhesive or like purposes

Country Status (2)

Country Link
FR (2) FR926378A (en)
GB (2) GB579340A (en)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3223672A (en) * 1960-12-28 1965-12-14 American Can Co Polyurethane solution and method of making same
US3233962A (en) * 1966-01-25 1966-02-08 Dennison Mfg Co Method of treating cellulose fibers and composition resulting therefrom
US3429650A (en) * 1960-04-15 1969-02-25 Us Agriculture Including finishing agents in at least one of two mutually immiscible solutions containing coreactants and serially applying said solutions to fibrous materials
US3481774A (en) * 1966-09-27 1969-12-02 Gen Mills Inc Treatment of wood and resulting treated product
US3506480A (en) * 1969-02-24 1970-04-14 Gen Mills Inc Oil filter paper and process of preparing same
EP1616039A2 (en) * 2003-01-22 2006-01-18 Panolam Industries International, Inc Flexible leather laminate

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3429650A (en) * 1960-04-15 1969-02-25 Us Agriculture Including finishing agents in at least one of two mutually immiscible solutions containing coreactants and serially applying said solutions to fibrous materials
US3223672A (en) * 1960-12-28 1965-12-14 American Can Co Polyurethane solution and method of making same
US3233962A (en) * 1966-01-25 1966-02-08 Dennison Mfg Co Method of treating cellulose fibers and composition resulting therefrom
US3481774A (en) * 1966-09-27 1969-12-02 Gen Mills Inc Treatment of wood and resulting treated product
US3506480A (en) * 1969-02-24 1970-04-14 Gen Mills Inc Oil filter paper and process of preparing same
EP1616039A2 (en) * 2003-01-22 2006-01-18 Panolam Industries International, Inc Flexible leather laminate
EP1616039A4 (en) * 2003-01-22 2008-04-16 Panolam Ind Int Inc Flexible leather laminate

Also Published As

Publication number Publication date
FR57695E (en) 1953-05-04
GB614991A (en) 1948-12-30
FR926378A (en) 1947-09-30

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