GB864692A - Improvements in and relating to the production of artificial threads - Google Patents
Improvements in and relating to the production of artificial threadsInfo
- 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
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
- C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
- C08G69/02—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids
- C08G69/08—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids derived from amino-carboxylic acids
- C08G69/10—Alpha-amino-carboxylic acids
-
- D—TEXTILES; PAPER
- D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
- D01F—CHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS
- D01F6/00—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof
- D01F6/58—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from homopolycondensation products
- D01F6/68—Monocomponent 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.
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)
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)
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 |
-
0
- NL NL238058D patent/NL238058A/xx unknown
-
1958
- 1958-04-21 GB GB12523/58A patent/GB864692A/en not_active Expired
-
1959
- 1959-04-10 FR FR791765A patent/FR1228448A/en not_active Expired
- 1959-04-11 BE BE577609A patent/BE577609A/en unknown
- 1959-05-19 GB GB16912/59A patent/GB917956A/en not_active Expired
-
1960
- 1960-05-19 FR FR827698A patent/FR77746E/en not_active Expired
- 1960-05-19 BE BE591015A patent/BE591015R/en active
-
1961
- 1961-04-19 GB GB14094/61A patent/GB931677A/en not_active Expired
- 1961-05-01 GB GB15637/61A patent/GB935396A/en not_active Expired
- 1961-12-01 US US161762A patent/US3089749A/en not_active Expired - Lifetime
-
1962
- 1962-04-19 BE BE616660A patent/BE616660R/en active
- 1962-04-19 FR FR1228448A patent/FR81497E/en not_active Expired
- 1962-04-19 NL NL277469D patent/NL277469A/xx unknown
Cited By (1)
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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