GB1124271A - Process for treatment of shaped articles - Google Patents

Process for treatment of shaped articles

Info

Publication number
GB1124271A
GB1124271A GB139565A GB139565A GB1124271A GB 1124271 A GB1124271 A GB 1124271A GB 139565 A GB139565 A GB 139565A GB 139565 A GB139565 A GB 139565A GB 1124271 A GB1124271 A GB 1124271A
Authority
GB
United Kingdom
Prior art keywords
acid
diamine
urea
amino
aliphatic
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
GB139565A
Inventor
Gwilym Thomas Jones
James Albert Moyse
Gerald Scott
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 GB139565A priority Critical patent/GB1124271A/en
Priority to US519427A priority patent/US3455734A/en
Priority to DE19661694401 priority patent/DE1694401A1/en
Priority to FR45614A priority patent/FR1469254A/en
Publication of GB1124271A publication Critical patent/GB1124271A/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
    • C08G69/00Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
    • C08G69/44Polyester-amides
    • 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
    • C08G65/34Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives
    • C08G65/38Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives derived from phenols
    • C08G65/44Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives derived from phenols by oxidation of phenols
    • 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
    • D06M15/59Polyamides; Polyimides

Landscapes

  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Polyamides (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)

Abstract

Polyesteramides are prepared by condensing an aliphatic dicarboxylic acid with a mixture of (a) a hydroxypolyoxyalkylene compound and (b) an aliphatic or cycloaliphatic amino-acid or lactam and/or an aliphatic or cycloaliphatic diamine. The dicarboxylic acid may be a C2- 12 polymethylene dicarboxylic acid, e.g. adipic or sebacic acid. The hydroxypolyoxyalkylene compound may have C2- 4 alkylene groups and a molecular weight of 300-6000. It may be prepared by addition of an alkylene oxide, e.g. ethylene or propylene oxide to a diol or higher polyol, a primary amine, a polyamine, a diamide, a polycarboxylic acid, or a po yhydric phenol. Compounds specified include polyoxyethylene glycol and ethylene oxide adducts of glycerol and octadecylamine. The amino-acid or lactam may be a C4- 12 polymethylene amino-acid or the corresponding lactam, e.g. caprolactam. The diamine may be a C2- 12 polymethylene diamine, e.g. hexamethylene diamine or the amine groups may be secondary. The diamine may be replaced by its salt with the carboxylic acid. The ratio of reactants may be such that the number of carboxyl groups present equals the sum of the amino and hydroxyl groups and so that the polyoxyalkylene compound constitutes 10-95% of the total reactants. The condensation may be at 150-300 DEG C., under an inert atmosphere, e.g. N2 and in the presence of antioxidants and stabilizers. A solvent or flux, e.g. o-phenyl phenol, may be added and distilled off after the reaction. The latter stages of the reaction may be carried out under reduced pressure. In Example (6) the reaction is carried out initially in a sealed tube. Finishing compositions for shaped articles, e.g. textiles, may be derived from the products of the invention. The material may be dissolved or dispersed in water or an aqueous or non-aqueous organic solvent, e.g. aqueous isopropanol. The solution or dispersion may also contain other polyesteramides prepared according to the invention, cross-linking agents, resin precondensates and catalyst for these, and antioxidants or thermal stabilizers. Compounds specified include dimethyol ethylene urea as a cross-linking agent, urea/formaldehyde resin and methylated urea/formaldehyde resin as resin precondensates, Zn(NO3)2 and NH4Cl as catalysts and bis-[2-hydroxy-3-(2-methylcyclohexyl) - 6 - methyl - phenyl] methane as anti-oxidant. After application the composition may be dried at up to 120 DEG C. or baked at 120-220 DEG C.ALSO:The invention comprises application of a condensation product of (a) an aliphatic dicarboxylic acid, (b) a hydroxypolyoxyalkylene compound and (c) an aliphatic (including cycloaliphatic) amino-acid or diamine to a shaped article, e.g. a textile fabric, of polymeric material. Each component (a), (b) and (c) may comprise a mixture of compounds and 10-95% of the reaction mixture may be component (b). 0.1 to 5% of the condensate in an aqueous medium may be applied to the textile fabric at room temperature or a temperature up to 50 DEG C. A cross-linking agent, a resin precondensate, a catalyst and/or an anti-oxidant may also be applied in the same aqueous medium or separately. The treated article may be dried at up to 120 DEG C and optionally further heated up to 220 DEG C. It may then be washed in hot detergent solutions and rinsed. This treatment which improves the moisture absorbency, anti-static properties, abrasion resistance and crease recovery of the textile may be carried out together with other treatments, e.g. the addition of optical brighteners. In Examples condensation products are derived from (a) adipic acid and sebacic acid, (b) polyoxyethylene glycol, an ethylene oxide-glycerol adduct and an ethylene oxide-octadecylamine adduct and (c) hexamethylene diamine or caprolactam. These condensates are dispersed in water or an isopropanol-water mixture and applied to polyamide, polyacrylonitrile, polyester, cotton, and cellulose triacetate fabrics sometimes together with urea-formaldehyde precondensate, methylate urea-formaldehyde precondensate, or dimethylol urea, catalysts: NH4Cl and Zn(NO3)26H2O and antioxidant: bis [2-hydroxy-3 (ortho-methylcyclohexyl)-5-methylphenyl] methane.
GB139565A 1965-01-12 1965-01-12 Process for treatment of shaped articles Expired GB1124271A (en)

Priority Applications (4)

Application Number Priority Date Filing Date Title
GB139565A GB1124271A (en) 1965-01-12 1965-01-12 Process for treatment of shaped articles
US519427A US3455734A (en) 1965-01-12 1966-01-10 Process of treating textiles with polycondensates containing amide and ester groups
DE19661694401 DE1694401A1 (en) 1965-01-12 1966-01-12 Process for applying a polyamide condensate to molded parts made from a natural or synthetic polymer material
FR45614A FR1469254A (en) 1965-01-12 1966-01-12 Polycondensation products and their application process

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB139565A GB1124271A (en) 1965-01-12 1965-01-12 Process for treatment of shaped articles

Publications (1)

Publication Number Publication Date
GB1124271A true GB1124271A (en) 1968-08-21

Family

ID=9721258

Family Applications (1)

Application Number Title Priority Date Filing Date
GB139565A Expired GB1124271A (en) 1965-01-12 1965-01-12 Process for treatment of shaped articles

Country Status (1)

Country Link
GB (1) GB1124271A (en)

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2542467A1 (en) * 1975-09-24 1977-03-31 Huels Chemische Werke Ag METHOD FOR MANUFACTURING POLYESTERAMIDES
US4020015A (en) 1971-10-12 1977-04-26 Lever Brothers Company Detergent compositions
US4075110A (en) 1975-04-15 1978-02-21 Lever Brothers Company Fabric treatment compositions
DE2712987A1 (en) * 1977-03-24 1978-10-05 Huels Chemische Werke Ag METHOD FOR PRODUCING POLYETHERESTERAMIDES WITH UNITS OF THE INITIAL COMPONENTS STATISTICALLY DISTRIBUTED IN THE POLYMER CHAIN
US4264645A (en) 1977-05-11 1981-04-28 Bayer Aktiengessellschaft Process for improving the water vapor absorption capacity of textile substrates
JPS5790017A (en) * 1980-11-25 1982-06-04 Toray Ind Inc Production of polyether-ester-amide
JPS58210925A (en) * 1982-06-02 1983-12-08 Toray Ind Inc Preparation of polyether ester amide
US4468505A (en) * 1982-08-18 1984-08-28 E. I. Du Pont De Nemours And Company Coating composition
WO2007012575A2 (en) * 2005-07-25 2007-02-01 Basf Se Solid pigment preparations containing water-soluble surface-active additives and anti-oxidants

Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4020015A (en) 1971-10-12 1977-04-26 Lever Brothers Company Detergent compositions
US4075110A (en) 1975-04-15 1978-02-21 Lever Brothers Company Fabric treatment compositions
DE2542467A1 (en) * 1975-09-24 1977-03-31 Huels Chemische Werke Ag METHOD FOR MANUFACTURING POLYESTERAMIDES
DE2712987A1 (en) * 1977-03-24 1978-10-05 Huels Chemische Werke Ag METHOD FOR PRODUCING POLYETHERESTERAMIDES WITH UNITS OF THE INITIAL COMPONENTS STATISTICALLY DISTRIBUTED IN THE POLYMER CHAIN
US4264645A (en) 1977-05-11 1981-04-28 Bayer Aktiengessellschaft Process for improving the water vapor absorption capacity of textile substrates
DE3145998A1 (en) * 1980-11-25 1982-06-24 Toray Industries, Inc., Tokyo POLYAETHER ESTERAMIDE AND METHOD FOR THE PRODUCTION THEREOF
JPS5790017A (en) * 1980-11-25 1982-06-04 Toray Ind Inc Production of polyether-ester-amide
JPH0146528B2 (en) * 1980-11-25 1989-10-09 Toray Industries
JPS58210925A (en) * 1982-06-02 1983-12-08 Toray Ind Inc Preparation of polyether ester amide
JPH0240686B2 (en) * 1982-06-02 1990-09-12 Toray Industries
US4468505A (en) * 1982-08-18 1984-08-28 E. I. Du Pont De Nemours And Company Coating composition
WO2007012575A2 (en) * 2005-07-25 2007-02-01 Basf Se Solid pigment preparations containing water-soluble surface-active additives and anti-oxidants
WO2007012575A3 (en) * 2005-07-25 2008-01-03 Basf Ag Solid pigment preparations containing water-soluble surface-active additives and anti-oxidants

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