US3621089A - Process for spinning dye-resistant copolyamide filaments - Google Patents
Process for spinning dye-resistant copolyamide filaments Download PDFInfo
- Publication number
- US3621089A US3621089A US578980A US3621089DA US3621089A US 3621089 A US3621089 A US 3621089A US 578980 A US578980 A US 578980A US 3621089D A US3621089D A US 3621089DA US 3621089 A US3621089 A US 3621089A
- Authority
- US
- United States
- Prior art keywords
- acid
- filaments
- stabilizer
- copolyamide
- basic
- 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 - Lifetime
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
-
- G—PHYSICS
- G21—NUCLEAR PHYSICS; NUCLEAR ENGINEERING
- G21C—NUCLEAR REACTORS
- G21C3/00—Reactor fuel elements and their assemblies; Selection of substances for use as reactor fuel elements
- G21C3/30—Assemblies of a number of fuel elements in the form of a rigid unit
- G21C3/36—Assemblies of plate-shaped fuel elements or coaxial tubes
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E30/00—Energy generation of nuclear origin
- Y02E30/30—Nuclear fission reactors
Definitions
- ABSTRACT A terpolyamide, formed from reactants polymerized in the presence of the equivalent of at least 3.0 mole percent of a monofunctional acid or basic stabilizer, is melt spun into filaments which are subsequently cold drawn.
- PROCESS FOR SPINNING DYE-RESISTANT COPOLYAMIDE ILAMENTS The present invention is concerned with filaments formed from copolyamides which resist dyeing by acid or basic dyestufis.
- Polyamide yarns, and fabrics made therefrom, are normally dyed with disperse or acid dyestuffs, basic dyestuffs being seldom used at present. in some end uses it is desirable that not all of the yarns employed should be dyed to the same extent by one of the above classes of dyestuffs, so that in piece dyeing, for example, contrast dyeing and other effects may be obtained. In order to achieve these effects some polyamide yarns are modified, e.g., chemically. in order to resist dyeing by, usually, acid dyestuffs. Such yarns are known as dye-resist yams. it is of course important that the modifications made to the yarns should in no way impair their desirable characteristics, and that physical properties of the different yarns should be as nearly as possible identical.
- copolyamides may be prepared which, while having substantially the same softening points as polyhexamethylene adipamide have considerably higher melt viscosities at the same, or nearly the same molecular weights.
- copolyamides referred to are ternary copolymers of polyhexamethylene adipamide and polyhexamethylene terephthalamide together with a minor proportion of a third component such as polyhexamethylene isophthalamide or polyepsilon caprolactam.
- the molecular weight of these ternary copolyamides can be decreased by the addition of relatively large amounts of a molecular weight stabilizer, for example an acid, without reducing the melt viscosities thereof to levels at which they cannot be melt spun as would normally be the case.
- a molecular weight stabilizer for example an acid
- the filaments obtained from copolyamides prepared in the presence of a relatively large amount of an acid stabilizer by the normal processes of melt spinning and drawing are resistant to acid dyeing.
- Use of correspondingly large amounts of a basic stabilizer would of course, render the yarns resistant to basic dyeing.
- Such filaments would, of course, also be useful in deep dye filaments since the large number of amine end groups available as a result of the addition of a basic stabilizer would make the filaments particularly suitable for acid dyeing.
- the present invention provides a process for the manufacture of polyamide filaments by melt spinning and subsequently cold drawing a copolyamide having a melt viscosity of at least 400 poisis at 290 C, wherein said copolyamide comprises at least 50 percent by weight of polyhexamethylene adipamide together with 20 percent to 40 percent by weight of polyhexamethylene terephthalate and from 2 to 20 percent by weight of a third polyamide and is formed by the polymerization of a mixture of hexamethylene diammonium adipate, hexamethylene diammonium terephthalate and a third polyamide forming salt or lactam in the presence of the equivalent of at least 3.0 mole percent of a monofunctional acid or basic stabilizer.
- the expression the equivalent of at least 3.0 mole percent of a monofunctional acid or basic stabilizer includes a difunctional stabilizer present in an amount equivalent to at least 3.0 mole percent of a monofunctional stabilizer.
- stabilizer is meant the acid or basic compound, e.g., acetic acid, normally added to a polyamide fonning salt to control the molecular weight thereof.
- the third polyamide forming salt or lactam in the mixture constitutes 5 to ID percent thereof and is hexamethylene diammonium isophthalate or epsilon caprolactam.
- the stabilizer may be an acid and is preferably a dibasic acid such as adipic acid or terephthalic acid.
- the yarn was knitted on a circular stocking machine together with a 66 nylon control and the fabric was dyed with Solway Blue B. A distinct shade difference was visible between the panels and after overdyeing with Dispersal fast Yellow A the panel containing the copolymer yarn was yellow and the 66 nylon control panel green.
- Filaments spun from the copolymers were resistant to acid dyeing.
- EXAMPLE IV TABLE 3 Properties of 6.6/6T/6 copolyamide stabilized with 2 mole percent of hexamethylene diamine 16 .1045 noises an Amine end group equivalents per l0 3. Carboxyl end group equivalents per l0 g. Melt viltcoulty Filaments spun from the copolymer were resistant to basic dyestuffs, but dyed well with acid dyes.
- a process for the manufacture of drawn terpolyamide filaments comprising melt spinning into filaments terpolyamide having a melt viscosity of at least 400 poises at 290C. and formed by the polymerization of a mixture of hexamethylene diammonium adipate, hexamethylene diammonium terephthalate and a third polyamide forming member selected from the group consisting of hexamethylene diammonium isophthalate and epsilon caprolactam in the presence of the equivalent of at least 3.0 mole percent of a monofunctional acid or basic stabilizer, and subsequently cold drawing the said filaments.
Landscapes
- Physics & Mathematics (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Plasma & Fusion (AREA)
- General Engineering & Computer Science (AREA)
- High Energy & Nuclear Physics (AREA)
- Polyamides (AREA)
- Artificial Filaments (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB39588/65A GB1114542A (en) | 1965-09-16 | 1965-09-16 | Dye-resist copolyamide filaments |
Publications (1)
Publication Number | Publication Date |
---|---|
US3621089A true US3621089A (en) | 1971-11-16 |
Family
ID=10410378
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US578980A Expired - Lifetime US3621089A (en) | 1965-09-16 | 1966-09-13 | Process for spinning dye-resistant copolyamide filaments |
Country Status (7)
Country | Link |
---|---|
US (1) | US3621089A (de) |
BE (1) | BE687016A (de) |
CH (1) | CH482847A (de) |
DE (1) | DE1669455A1 (de) |
GB (1) | GB1114542A (de) |
LU (1) | LU51970A1 (de) |
NL (1) | NL6613152A (de) |
Cited By (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3926924A (en) * | 1965-09-16 | 1975-12-16 | Ici Ltd | Polyamide copolymers from hexamethylene diammonium adipate/terephthalate and a third polyamide forming reactant |
US4076696A (en) * | 1976-12-09 | 1978-02-28 | Chevron Research Company | Extrusion of polypyrrolidone |
US4521484A (en) * | 1984-06-07 | 1985-06-04 | E. I. Du Pont De Nemours And Company | Self-crimping polyamide filaments |
US5081222A (en) * | 1987-07-17 | 1992-01-14 | Basf Aktiengesellschaft | Partly aromatic copolyamide of reduced triamine content |
US5223196A (en) * | 1990-11-20 | 1993-06-29 | E. I. Du Pont De Nemours And Company | Processing of pigmented nylon fibers using modified polymers |
US5298595A (en) * | 1987-07-17 | 1994-03-29 | Basf Aktiengesellschaft | Partly aromatic copolyamides of reduced triamine content |
US5422420A (en) * | 1990-11-20 | 1995-06-06 | E. I. Du Pont De Nemours And Company | Terpolyamides and multipolyamides containing amide units of 2-methylpentamethylenediamine and products prepared therefrom |
US5504146A (en) * | 1988-02-12 | 1996-04-02 | Basf Aktiengesellschaft | Toughened partly aromatic copolyamides |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB1581745A (en) | 1976-03-30 | 1980-12-17 | British Industrial Plastics | Hot melt adhesive |
US20060030693A1 (en) † | 2004-07-27 | 2006-02-09 | Martens Marvin M | Process for the preparation of thermoplastic polyamide and polyester compositions exhibiting increased melt flow and articles formed therefrom |
Citations (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2163584A (en) * | 1936-12-01 | 1939-06-27 | Du Pont | Preparation of polyamides |
US2252555A (en) * | 1939-04-04 | 1941-08-12 | Wilmington Trust Co | Polymeric material |
US3322731A (en) * | 1962-05-22 | 1967-05-30 | Du Pont | Interpolymers of caprolactam, hexamethylene diamine, adipic acid and sebacic acid |
US3376369A (en) * | 1964-03-13 | 1968-04-02 | Du Pont | Process for making molecular oriented fibers of polymerized lactams |
US3380968A (en) * | 1965-05-21 | 1968-04-30 | Monsanto Co | Novel terpolyamides from phenylindan carboxylic acid |
US3383369A (en) * | 1965-05-24 | 1968-05-14 | Monsanto Co | Novel terpolyamides of aliphatic and aromatic acids and process |
US3388099A (en) * | 1965-05-14 | 1968-06-11 | Monsanto Co | Terpolyamides |
US3454536A (en) * | 1964-11-12 | 1969-07-08 | Chemische Werke Witten Gmbh | Process for the preparation of polyamides |
US3475387A (en) * | 1963-08-31 | 1969-10-28 | British Nylon Spinners Ltd | Manufacture of polyamides from aromatic dicarboxylic acids |
US3500498A (en) * | 1966-05-28 | 1970-03-17 | Asahi Chemical Ind | Apparatus for the manufacture of conjugated sheath-core type composite fibers |
-
1965
- 1965-09-16 GB GB39588/65A patent/GB1114542A/en not_active Expired
-
1966
- 1966-09-13 US US578980A patent/US3621089A/en not_active Expired - Lifetime
- 1966-09-15 LU LU51970A patent/LU51970A1/xx unknown
- 1966-09-16 BE BE687016D patent/BE687016A/xx unknown
- 1966-09-16 NL NL6613152A patent/NL6613152A/xx unknown
- 1966-09-16 CH CH1338766A patent/CH482847A/de not_active IP Right Cessation
- 1966-09-16 DE DE19661669455 patent/DE1669455A1/de active Pending
Patent Citations (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2163584A (en) * | 1936-12-01 | 1939-06-27 | Du Pont | Preparation of polyamides |
US2252555A (en) * | 1939-04-04 | 1941-08-12 | Wilmington Trust Co | Polymeric material |
US3322731A (en) * | 1962-05-22 | 1967-05-30 | Du Pont | Interpolymers of caprolactam, hexamethylene diamine, adipic acid and sebacic acid |
US3475387A (en) * | 1963-08-31 | 1969-10-28 | British Nylon Spinners Ltd | Manufacture of polyamides from aromatic dicarboxylic acids |
US3376369A (en) * | 1964-03-13 | 1968-04-02 | Du Pont | Process for making molecular oriented fibers of polymerized lactams |
US3454536A (en) * | 1964-11-12 | 1969-07-08 | Chemische Werke Witten Gmbh | Process for the preparation of polyamides |
US3388099A (en) * | 1965-05-14 | 1968-06-11 | Monsanto Co | Terpolyamides |
US3380968A (en) * | 1965-05-21 | 1968-04-30 | Monsanto Co | Novel terpolyamides from phenylindan carboxylic acid |
US3383369A (en) * | 1965-05-24 | 1968-05-14 | Monsanto Co | Novel terpolyamides of aliphatic and aromatic acids and process |
US3500498A (en) * | 1966-05-28 | 1970-03-17 | Asahi Chemical Ind | Apparatus for the manufacture of conjugated sheath-core type composite fibers |
Non-Patent Citations (1)
Title |
---|
Bulletin of the Oyonite Chemical Co., Bulletin No. 10 (revised Apr. 22, 1955), U.S. Pat. Office Scientific Library, received Nov. 27, 1957, composed of a total of 63 pages; 4 pages, excerpts. * |
Cited By (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3926924A (en) * | 1965-09-16 | 1975-12-16 | Ici Ltd | Polyamide copolymers from hexamethylene diammonium adipate/terephthalate and a third polyamide forming reactant |
US4218509A (en) * | 1965-09-16 | 1980-08-19 | Imperial Chemical Industries, Limited | Polyamide copolymers |
US4076696A (en) * | 1976-12-09 | 1978-02-28 | Chevron Research Company | Extrusion of polypyrrolidone |
US4521484A (en) * | 1984-06-07 | 1985-06-04 | E. I. Du Pont De Nemours And Company | Self-crimping polyamide filaments |
US5081222A (en) * | 1987-07-17 | 1992-01-14 | Basf Aktiengesellschaft | Partly aromatic copolyamide of reduced triamine content |
US5298595A (en) * | 1987-07-17 | 1994-03-29 | Basf Aktiengesellschaft | Partly aromatic copolyamides of reduced triamine content |
US5504146A (en) * | 1988-02-12 | 1996-04-02 | Basf Aktiengesellschaft | Toughened partly aromatic copolyamides |
US5223196A (en) * | 1990-11-20 | 1993-06-29 | E. I. Du Pont De Nemours And Company | Processing of pigmented nylon fibers using modified polymers |
US5391703A (en) * | 1990-11-20 | 1995-02-21 | E. I. Du Pont De Nemours And Company | Polyamide pigment dispersion |
US5422420A (en) * | 1990-11-20 | 1995-06-06 | E. I. Du Pont De Nemours And Company | Terpolyamides and multipolyamides containing amide units of 2-methylpentamethylenediamine and products prepared therefrom |
Also Published As
Publication number | Publication date |
---|---|
LU51970A1 (de) | 1966-11-15 |
DE1669455A1 (de) | 1969-10-16 |
GB1114542A (en) | 1968-05-22 |
CH482847A (de) | 1969-12-15 |
NL6613152A (de) | 1967-03-17 |
BE687016A (de) | 1967-03-16 |
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