GB864692A - Improvements in and relating to the production of artificial threads - Google Patents

Improvements in and relating to the production of artificial threads

Info

Publication number
GB864692A
GB864692A GB12523/58A GB1252358A GB864692A GB 864692 A GB864692 A GB 864692A GB 12523/58 A GB12523/58 A GB 12523/58A GB 1252358 A GB1252358 A GB 1252358A GB 864692 A GB864692 A GB 864692A
Authority
GB
United Kingdom
Prior art keywords
solvent
polypeptide
glutamate
methyl
gamma
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
GB12523/58A
Inventor
Denis George Harold Ballard
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.)
Akzo Nobel UK PLC
Original Assignee
Courtaulds PLC
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
Priority to NL238058D priority Critical patent/NL238058A/xx
Priority to GB12523/58A priority patent/GB864692A/en
Application filed by Courtaulds PLC filed Critical Courtaulds PLC
Priority to FR791765A priority patent/FR1228448A/en
Priority to BE577609A priority patent/BE577609A/en
Priority to GB16912/59A priority patent/GB917956A/en
Priority to BE591015A priority patent/BE591015R/en
Priority to FR827698A priority patent/FR77746E/en
Publication of GB864692A publication Critical patent/GB864692A/en
Priority to GB14094/61A priority patent/GB931677A/en
Priority to GB15637/61A priority patent/GB935396A/en
Priority to US161762A priority patent/US3089749A/en
Priority to NL277469D priority patent/NL277469A/xx
Priority to BE616660A priority patent/BE616660R/en
Priority to FR1228448A priority patent/FR81497E/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
    • C08G69/02Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids
    • C08G69/08Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids derived from amino-carboxylic acids
    • C08G69/10Alpha-amino-carboxylic acids
    • DTEXTILES; PAPER
    • D01NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
    • D01FCHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS
    • D01F6/00Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof
    • D01F6/58Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from homopolycondensation products
    • D01F6/68Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from homopolycondensation products from polyaminoacids or polypeptides

Landscapes

  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Artificial Filaments (AREA)
  • Polyamides (AREA)
  • Manufacture Of Macromolecular Shaped Articles (AREA)

Abstract

Fibres of an optically active form of poly-gamma-methyl glutamate are produced by polymerizing an optically active gamma-methyl glutamate N-carboxy anhydride in an organic liquid which is a solvent for the polypeptide formed, the polypeptide being composed of at least 90% by weight of units of the optically active glutamate ester, dry or wet spinning a solution of the polypeptide while it is still in the "solvated state" so that the polypeptide is in the alpha-configuration on extrusion, and stretching the resultant fibre while it is still in this configuration, thereby converting the polypeptide into the beta-configuration and orienting the fibre along its axis. The polypeptide may be a copolymer of the ester with up to 10% of one or more other N-carboxy anhydrides such as the anhydrides of leucine, phenylalanine, norleucine, isoleucine or gamma-benzyl-glutamate. The polypeptide may be a mixture of the optically active forms of poly-gamma-methyl-glutamate, provided that at least 90% by weight of the mixture consists of one optically active form only. The term "solvated state" is defined as meaning that the polypeptide is dissolved either in the solvent in which the polymerization was effected, or in a different solvent, the polymerization solvent having been removed and replaced by the other solvent, but the polypeptide not having been allowed to dry out before the spinning step. The polypeptide may alternatively be dissolved in a solvent, a part of which consists of the solvent in which the polymerization was effected. The spinning solution solvent may be a chlorinated aliphatic hydrocarbon, preferably containing not more than 4 carbon atoms and at least 2 chlorine atoms in the molecule, or it may be N, N-dimethyl formamide. The solvent may contain diluents such as dioxane, ethyl or methyl acetate, methyl propionate or acetone. When threads are formed by wet spinning the coagulant liquid must be a non-solvent for the polymer which is miscible with the spinning solvent. It is preferably miscible with water, and the coagulant liquid may then be removed from the thread immediately after leaving the bath by washing it with water. The stretching of the thread is preferably effected while it is wet with water. In an example, 9,8 parts of gamma-methyl-L-glutamate N-carboxy anhydride dissolved in 100 parts of a mixture of 80 volumes of methylene chloride and 20 volumes of dioxane are polymerized at ordinary temperature by the addition of 0,16 part of tri-n-butyl amine to form a 7,5% solution of a poly-gammamethyl-L-glutamate which is wet-spun into acetone containing about 5% by volume of water and less than 10% by volume of methylene chloride. The filaments thus formed are withdrawn from the coagulating bath, passed through a water bath, stretched 90% while still wet, and dried on a steam-heated godet. Examples are given also in which solutions of the polymer are dry-spun. The threads produced by the process of the invention are insoluble in chlorinated hydrocarbons, and fabrics woven from them have the appearance and crease-resistance of fabrics of natural silk and high safe ironing temperatures. Specifications 675,298, 675,299, 690,341 and 692,433 are referred to.
GB12523/58A 1958-04-21 1958-04-21 Improvements in and relating to the production of artificial threads Expired GB864692A (en)

Priority Applications (13)

Application Number Priority Date Filing Date Title
NL238058D NL238058A (en) 1958-04-21
GB12523/58A GB864692A (en) 1958-04-21 1958-04-21 Improvements in and relating to the production of artificial threads
FR791765A FR1228448A (en) 1958-04-21 1959-04-10 Production of artificial fibers from polypeptides
BE577609A BE577609A (en) 1958-04-21 1959-04-11 Improvements in the production of artificial yarns
GB16912/59A GB917956A (en) 1958-04-21 1959-05-19 Improvements in and relating to the production of poly-gamma-ethyl glutamate fibres
BE591015A BE591015R (en) 1958-04-21 1960-05-19 Improvements in the production of artificial yarns
FR827698A FR77746E (en) 1958-04-21 1960-05-19 Production of artificial fibers from polypeptides
GB14094/61A GB931677A (en) 1958-04-21 1961-04-19 Improvements in and relating to the production of artificial threads
GB15637/61A GB935396A (en) 1958-04-21 1961-05-01 Improvements in and relating to the production of poly-gamma-methyl glutamate and poly-gamma-ethyl glutamate films
US161762A US3089749A (en) 1958-04-21 1961-12-01 Production of artificial threads
NL277469D NL277469A (en) 1958-04-21 1962-04-19
BE616660A BE616660R (en) 1958-04-21 1962-04-19 Improvements in the production of artificial yarns
FR1228448A FR81497E (en) 1958-04-21 1962-04-19 Production of artificial fibers from polypeptides

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
GB12523/58A GB864692A (en) 1958-04-21 1958-04-21 Improvements in and relating to the production of artificial threads
GB16912/59A GB917956A (en) 1958-04-21 1959-05-19 Improvements in and relating to the production of poly-gamma-ethyl glutamate fibres
GB14094/61A GB931677A (en) 1958-04-21 1961-04-19 Improvements in and relating to the production of artificial threads

Publications (1)

Publication Number Publication Date
GB864692A true GB864692A (en) 1961-04-06

Family

ID=43034292

Family Applications (4)

Application Number Title Priority Date Filing Date
GB12523/58A Expired GB864692A (en) 1958-04-21 1958-04-21 Improvements in and relating to the production of artificial threads
GB16912/59A Expired GB917956A (en) 1958-04-21 1959-05-19 Improvements in and relating to the production of poly-gamma-ethyl glutamate fibres
GB14094/61A Expired GB931677A (en) 1958-04-21 1961-04-19 Improvements in and relating to the production of artificial threads
GB15637/61A Expired GB935396A (en) 1958-04-21 1961-05-01 Improvements in and relating to the production of poly-gamma-methyl glutamate and poly-gamma-ethyl glutamate films

Family Applications After (3)

Application Number Title Priority Date Filing Date
GB16912/59A Expired GB917956A (en) 1958-04-21 1959-05-19 Improvements in and relating to the production of poly-gamma-ethyl glutamate fibres
GB14094/61A Expired GB931677A (en) 1958-04-21 1961-04-19 Improvements in and relating to the production of artificial threads
GB15637/61A Expired GB935396A (en) 1958-04-21 1961-05-01 Improvements in and relating to the production of poly-gamma-methyl glutamate and poly-gamma-ethyl glutamate films

Country Status (5)

Country Link
US (1) US3089749A (en)
BE (3) BE577609A (en)
FR (3) FR1228448A (en)
GB (4) GB864692A (en)
NL (2) NL277469A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3344219A (en) * 1963-07-18 1967-09-26 Process for manufacturing shaped articles of optically active poly-sf-methyl glutamate

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3230274A (en) * 1960-12-30 1966-01-18 Merck & Co Inc Preparation of linear polypeptides
DE1253863B (en) * 1962-03-27 1967-11-09 Ajinomoto Kk Process for producing fibers, consisting of a mixture of regenerated cellulose and a polymeric amino acid
NL297020A (en) * 1962-08-24
US3371069A (en) * 1963-03-20 1968-02-27 Ajinomoto Kk Filaments and surgical sutures of polyl-glutamic acid partly esterified with lower alkanols and process therefor
GB1024393A (en) * 1963-03-30 1966-03-30 Asahi Chemical Ind Process for polymerizing n-carboxy-ª‡-amino acid anhydrides
USRE30170E (en) * 1975-04-04 1979-12-18 Sutures, Inc. Hydrolyzable polymers of amino acid and hydroxy acids
US5171505A (en) * 1990-11-28 1992-12-15 E. I. Du Pont De Nemours And Company Process for spinning polypeptide fibers

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3344219A (en) * 1963-07-18 1967-09-26 Process for manufacturing shaped articles of optically active poly-sf-methyl glutamate

Also Published As

Publication number Publication date
NL277469A (en) 1964-11-10
GB917956A (en) 1963-02-13
GB935396A (en) 1963-08-28
US3089749A (en) 1963-05-14
NL238058A (en)
FR1228448A (en) 1960-08-29
BE616660R (en) 1962-08-16
FR81497E (en) 1963-09-27
BE591015R (en) 1960-09-16
GB931677A (en) 1963-07-17
FR77746E (en) 1962-04-13
BE577609A (en) 1959-07-31

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