GB1117947A - High strength polyamide yarn - Google Patents
High strength polyamide yarnInfo
- Publication number
- GB1117947A GB1117947A GB2521/66A GB252166A GB1117947A GB 1117947 A GB1117947 A GB 1117947A GB 2521/66 A GB2521/66 A GB 2521/66A GB 252166 A GB252166 A GB 252166A GB 1117947 A GB1117947 A GB 1117947A
- Authority
- GB
- United Kingdom
- Prior art keywords
- mixture
- polymerization
- acids
- compounds
- agents
- 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
- 239000004952 Polyamide Substances 0.000 title abstract 2
- 229920002647 polyamide Polymers 0.000 title abstract 2
- 239000000203 mixture Substances 0.000 abstract 5
- 238000006116 polymerization reaction Methods 0.000 abstract 4
- -1 heteroaliphatic Chemical group 0.000 abstract 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 150000007513 acids Chemical class 0.000 abstract 2
- 239000000654 additive Substances 0.000 abstract 2
- 150000004982 aromatic amines Chemical class 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- TXWSZJSDZKWQAU-UHFFFAOYSA-N 2,9-dimethyl-5,12-dihydroquinolino[2,3-b]acridine-7,14-dione Chemical compound N1C2=CC=C(C)C=C2C(=O)C2=C1C=C(C(=O)C=1C(=CC=C(C=1)C)N1)C1=C2 TXWSZJSDZKWQAU-UHFFFAOYSA-N 0.000 abstract 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 abstract 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 abstract 1
- 229920002292 Nylon 6 Polymers 0.000 abstract 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 abstract 1
- 150000001243 acetic acids Chemical class 0.000 abstract 1
- 125000002723 alicyclic group Chemical group 0.000 abstract 1
- 125000001931 aliphatic group Chemical group 0.000 abstract 1
- 150000001412 amines Chemical group 0.000 abstract 1
- 150000008064 anhydrides Chemical class 0.000 abstract 1
- 229910052787 antimony Inorganic materials 0.000 abstract 1
- 239000002216 antistatic agent Substances 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 239000003899 bactericide agent Substances 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 239000012141 concentrate Substances 0.000 abstract 1
- 229910052802 copper Inorganic materials 0.000 abstract 1
- 239000010949 copper Substances 0.000 abstract 1
- 239000003431 cross linking reagent Substances 0.000 abstract 1
- 150000001991 dicarboxylic acids Chemical class 0.000 abstract 1
- 150000005690 diesters Chemical class 0.000 abstract 1
- 150000002118 epoxides Chemical class 0.000 abstract 1
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 abstract 1
- 239000003063 flame retardant Substances 0.000 abstract 1
- 239000007850 fluorescent dye Substances 0.000 abstract 1
- 150000002311 glutaric acids Chemical class 0.000 abstract 1
- 150000002366 halogen compounds Chemical class 0.000 abstract 1
- 239000012760 heat stabilizer Substances 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 239000011261 inert gas Substances 0.000 abstract 1
- 239000001023 inorganic pigment Substances 0.000 abstract 1
- 150000008040 ionic compounds Chemical class 0.000 abstract 1
- 239000012948 isocyanate Substances 0.000 abstract 1
- 150000002513 isocyanates Chemical class 0.000 abstract 1
- 150000002576 ketones Chemical class 0.000 abstract 1
- 239000004611 light stabiliser Substances 0.000 abstract 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 abstract 1
- 239000000178 monomer Substances 0.000 abstract 1
- WPUMVKJOWWJPRK-UHFFFAOYSA-N naphthalene-2,7-dicarboxylic acid Chemical class C1=CC(C(O)=O)=CC2=CC(C(=O)O)=CC=C21 WPUMVKJOWWJPRK-UHFFFAOYSA-N 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 abstract 1
- 239000002245 particle Substances 0.000 abstract 1
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 abstract 1
- 229910052698 phosphorus Inorganic materials 0.000 abstract 1
- 239000000049 pigment Substances 0.000 abstract 1
- 229920000139 polyethylene terephthalate Polymers 0.000 abstract 1
- 239000005020 polyethylene terephthalate Substances 0.000 abstract 1
- 229920000642 polymer Polymers 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 230000001737 promoting effect Effects 0.000 abstract 1
- 230000003014 reinforcing effect Effects 0.000 abstract 1
- 239000007787 solid Substances 0.000 abstract 1
- 238000003756 stirring Methods 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- 150000003444 succinic acids Chemical class 0.000 abstract 1
- 239000011135 tin Substances 0.000 abstract 1
- 229910052718 tin Inorganic materials 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L77/00—Compositions of polyamides obtained by reactions forming a carboxylic amide link in the main chain; Compositions of derivatives of such polymers
-
- 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
- C08G69/14—Lactams
- C08G69/16—Preparatory processes
-
- 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
- D01F1/00—General methods for the manufacture of artificial filaments or the like
- D01F1/02—Addition of substances to the spinning solution or to the melt
- D01F1/10—Other agents for modifying properties
-
- 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
- D01F6/60—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from homopolycondensation products from polyamides
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Textile Engineering (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Manufacturing & Machinery (AREA)
- Polyamides (AREA)
- Artificial Filaments (AREA)
Abstract
The invention comprises linear fibre-forming modified poly-e -caprolactams having up to 135 milligram equivalents of end groups, up to 20 of which are primary amino, the remainder being carboxyl, the logarithm of the Brabender melt viscosity of the polycaprolactam being not more than 1.017 + 6 x 10-5 M, where M is the number average M.W. and is at least 15,000. It may be produced by heating at 240-290 DEG C. a molten mixture of e -caprolactam and 0.1-0.7 mole per cent of a C6- 20 dicarboxylic acid and stirring the mixture whilst its surface is swept with an inert gas at a flow rate of at least twice the volume of the mixture per hr. Alternatively the mixture may be heated under reduced pressure or solid state polymerization may be effected. A copolyamide may be produced. Dicarboxylic acids specified are aliphatic, heteroaliphatic, alicyclic and aromatic non-volatile acids which may contain substituent groups. They include sebacic, pimelic, suberic, azelaic, adipic, undecanedioic, dodecanedioic, tridecanedioic, tetradecanedioic, terephthalic, bibenzoic, phthalic and naphthalene-2,7-dicarboxylic acids. The use of acetic, succinic and glutaric acids is also disclosed. The acids may be replaced by their mono- or diesters or anhydrides. The polymerization may be batch-wise or continuous and may be catalysed by the presence of water. Additives, optionally as concentrates in the monomer or polyamide may be introduced at any stage of the polymerization. If corrosive, they may be added at the centre of the polymerization mixture by means of a non-corroding tube and then dispersed outward. Additives specified are flame retardants, e.g. Sb, P and halogen compounds, TiO2 as a delustrant, antistatic agents, adhesion promoting compounds, e.g. isocyanates and epoxides, heat and light stabilizers, e.g. ionic reducing compounds, ionic compounds of manganese, copper and tin, phosphites, alkylated aromatic amines, and ketone/aromatic amine condensates, pigments, e.g. 2, 9-dimethylquinacridone and inorganic pigments, fluorescent agents, brighteners, cross-linking agents, bacteriocides, e.g. phenol and quaternary amines, colloidal reinforcing particles, antisoiling agents, and other polymers, e.g. polyethylene terephthalate. In typical Example (1) the reaction is carried out initially under a superatmospheric steam pressure which is later reduced to atmospheric pressure and then replaced by a current of nitrogen.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US426632A US3386967A (en) | 1965-01-19 | 1965-01-19 | Polycaproamide having excess number of carboxyl end groups over amino end groups |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1117947A true GB1117947A (en) | 1968-06-26 |
Family
ID=23691590
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2521/66A Expired GB1117947A (en) | 1965-01-19 | 1966-01-19 | High strength polyamide yarn |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US3386967A (en) |
| BE (1) | BE675293A (en) |
| CH (1) | CH478862A (en) |
| DE (1) | DE1595253A1 (en) |
| ES (1) | ES321938A1 (en) |
| FR (1) | FR1463736A (en) |
| GB (1) | GB1117947A (en) |
| NL (1) | NL6600662A (en) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1070613A (en) * | 1965-06-10 | 1967-06-01 | Ici Ltd | Polyester fibres of improved dyeability |
| GB1140463A (en) * | 1965-07-02 | 1969-01-22 | Ici Ltd | Block polyester polyamides |
| US3522328A (en) * | 1967-10-11 | 1970-07-28 | Eastman Kodak Co | Modified polyester compositions containing polyamides prepared from aromatic diamines |
| US3527843A (en) * | 1968-04-11 | 1970-09-08 | Allied Chem | Polylactam with polyester with 0.005 to 0.1 mol of 2,2-bis(hydroxymethyl) propionic acid per mol of lactam |
| US3511815A (en) * | 1968-05-08 | 1970-05-12 | Ahmet Nuri Sayin | Deep dyeing polycarbonamide filament |
| US3846532A (en) * | 1969-01-29 | 1974-11-05 | Bayer Ag | Continuous spinning and stretching process of the production of polyamide-6 filaments |
| USRE28937E (en) * | 1971-11-18 | 1976-08-24 | Allied Chemical Corporation | Control of viscosity and polycaproamide degradation during vacuum polycondensation |
| IT1109902B (en) * | 1979-01-05 | 1985-12-23 | Snia Viscosa | PROCESS FOR THE PRODUCTION OF SYNTHETIC POLYAMIDS, FLAME RESISTANT, SUITABLE FOR SPINNING, AND FOR THE PRODUCTION OF FLAME RESISTANT FILAMENTS AND FIBERS AND PRODUCTS OBTAINED BY SUCH PROCEDURE |
| JPS62263319A (en) * | 1986-05-06 | 1987-11-16 | Teijin Ltd | Melt spinning of polyamide |
| US5194319A (en) * | 1988-03-07 | 1993-03-16 | Kanebo, Ltd. | Shaped polyamide articles and process for manufacturing the same |
| DE4019780A1 (en) * | 1990-06-21 | 1992-01-02 | Basf Ag | METHOD FOR THE CONTINUOUS PRODUCTION OF POLYCAPROLACTAM WITH REGULATED AMINO END GROUP CONTENT |
| US5462802A (en) * | 1991-12-02 | 1995-10-31 | Teijin Limited | Polyamide hollow and/or non-circular fiber and process for making same |
| DE4218719A1 (en) * | 1992-06-06 | 1993-12-09 | Basf Ag | Fast-spun threads based on polycaprolactam and process for their production |
| DE4421704A1 (en) * | 1994-06-21 | 1996-01-04 | Bayer Ag | Process for the production of high molecular weight polyamide 6 |
| BE1010331A3 (en) * | 1996-06-06 | 1998-06-02 | Dsm Nv | ACID dyeable fiber. |
| DE19801267B4 (en) | 1998-01-15 | 2005-03-24 | Inventa-Fischer Gmbh | Process for the preparation of PA-6 granules and their use |
| DE19812135A1 (en) * | 1998-03-20 | 1999-09-23 | Basf Ag | Production of polyamide with improved wet fastness, useful for production of filaments, fibers, film, sheet materials and moldings |
| US20060292385A1 (en) * | 2004-07-27 | 2006-12-28 | Andreas Renekn | Method of plating mineral filled polyamide compositions and articles formed thereby |
| ES2335940T3 (en) * | 2006-02-08 | 2010-04-06 | Dsm Ip Assets B.V. | PROCESS TO INCREASE THE MOLECULAR WEIGHT OF POLYAMIDE. |
| US10767012B2 (en) | 2017-04-10 | 2020-09-08 | Firestone Fibers & Textiles Company, Llc | Functionalized polyamides and methods of preparing the same |
| CN114989422A (en) * | 2022-06-21 | 2022-09-02 | 浙江理工大学 | Polyamide material for industrial yarn, preparation method thereof and fiber |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2241323A (en) * | 1938-09-30 | 1941-05-06 | Du Pont | Process for preparing polyamides |
| US2241322A (en) * | 1938-09-30 | 1941-05-06 | Du Pont | Process for preparing polyamides from cyclic amides |
| DE766120C (en) * | 1941-06-19 | 1954-06-21 | Ig Farbenindustrie Ag | Process for refining superpolyamides from ªÏ-aminocarboxylic acids |
| CH245374A (en) * | 1943-07-28 | 1946-11-15 | Ag Bata | Process for producing a polyamide by polymerizing 6-caprolactam. |
| DE935696C (en) * | 1944-10-27 | 1955-11-24 | Phrix Werke Ag | Process for the production of super polyamides |
| US2805214A (en) * | 1955-05-27 | 1957-09-03 | Du Pont | Polymerization of lactam with mixed catalyst |
| NL113790C (en) * | 1955-06-30 | 1900-01-01 | ||
| IT595427A (en) * | 1955-06-30 | |||
| GB890437A (en) * | 1958-02-20 | 1962-02-28 | Du Pont | Polycarbonamides |
| BE529624A (en) * | 1958-08-05 | |||
| US3109835A (en) * | 1958-10-08 | 1963-11-05 | Allied Chem | Process for producing ultrahigh viscosity polycaprolactam |
| US3003222A (en) * | 1958-11-17 | 1961-10-10 | Du Pont | Controlled relaxation of freshly drawn nylon |
| US3090997A (en) * | 1958-11-26 | 1963-05-28 | Du Pont | Method of continuous treatment of as-spun birefringent polyamide filaments |
-
1965
- 1965-01-19 US US426632A patent/US3386967A/en not_active Expired - Lifetime
-
1966
- 1966-01-18 BE BE675293D patent/BE675293A/xx unknown
- 1966-01-18 CH CH62266A patent/CH478862A/en not_active IP Right Cessation
- 1966-01-18 DE DE19661595253 patent/DE1595253A1/en active Pending
- 1966-01-18 ES ES0321938A patent/ES321938A1/en not_active Expired
- 1966-01-18 NL NL6600662A patent/NL6600662A/xx unknown
- 1966-01-18 FR FR46327A patent/FR1463736A/en not_active Expired
- 1966-01-19 GB GB2521/66A patent/GB1117947A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| US3386967A (en) | 1968-06-04 |
| CH478862A (en) | 1969-09-30 |
| DE1595253A1 (en) | 1970-03-05 |
| BE675293A (en) | 1966-05-16 |
| NL6600662A (en) | 1966-07-20 |
| FR1463736A (en) | 1966-06-03 |
| ES321938A1 (en) | 1966-10-16 |
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