WO2006102975A1 - Low-melting-point copolyamides and their use as hot-melt adhesives - Google Patents
Low-melting-point copolyamides and their use as hot-melt adhesives Download PDFInfo
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- WO2006102975A1 WO2006102975A1 PCT/EP2006/002195 EP2006002195W WO2006102975A1 WO 2006102975 A1 WO2006102975 A1 WO 2006102975A1 EP 2006002195 W EP2006002195 W EP 2006002195W WO 2006102975 A1 WO2006102975 A1 WO 2006102975A1
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- copolyamides
- diacid
- copolyamide
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- 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
- C08G69/36—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids derived from amino acids, polyamines and polycarboxylic acids
-
- 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
Definitions
- the present invention relates to low-melting-point copolyamides and their use as hot-melt adhesives. More precisely, these copolyamides are prepared from long- chain saturated dicarboxylic acids of formula HOOC- (CH2) n""COOH i- n which n is an integer between 11 and 16, these diacids possibly being branched. These copolyamides are useful as adhesives of the HMA (hot- melt adhesive) type, that is to say they are deposited in the molten state on the surfaces to be bonded and then the adhesion is obtained when they return to the solid state by cooling. These adhesives are useful in the textile industry.
- HMA hot- melt adhesive
- Patent Application DE OS 1594233 discloses copolyamides resulting either from the condensation of lauryllactam and caprolactam, or from the condensation (i) of lauryllactam and (ii) hexamethylenediamine and adipic acid in stoichiometric proportions, or else from the condensation (i) of lauryllactam, (ii) caprolactam and (iii) hexamethylenediamine and adipic acid in stoichiometric proportions.
- Patent Application DE OS 2324160 discloses copolyamides resulting from the condensation of lauryllactam, 11- aminoundecanoic acid, caprolactam and hexamethylenediamine with one or more diacids having from 6 to 13 carbon atoms.
- Patent Application EP 627 454 discloses copolyamides resulting from the condensation of at least 10% by weight of lauryllactam or 11-aminoundecanoic acid and hexamethylenediamine with one or more diacids having from 6 to 12 carbon atoms.
- Patent Application EP 1 153 957 discloses copolyamides resulting from the condensation of caprolactam, lauryllactam or 11-aminoundecanoic acid and a diamine with at least two diacids having from 6 to 14 carbon atoms.
- Copolyamides have now been found that are at least as hydrophobic as, and often more hydrophobic than, those of the prior art.
- the advantage is that they have a lower water uptake and, when used as textile adhesives, the bond has a better resistance to steam and to cleaning solvents.
- Another advantage of these copolyamides is that they melt at lower temperature.
- the present invention relates to copolyamides of formula:
- these copolyamides have a melting point of between 80 0 C and 15O 0 C and an MFI (melt flow index) of between 3 and 80 g/10 min (2.16 kg/150°C) .
- the melting point is measured by DSC (differential scanning calorimetry) or, according to DIN 53736, Part B (visual determination of the melting point of semicrystalline plastics) optically using a hot stage microscope. They can be made by the usual process described in the prior art .
- the present invention also relates to adhesives of the HMA type consisting of the above copolyamides. These adhesives are useful in the textile industry.
- copolyamides of the invention may be manufactured using the standard processes described in the prior art.
- the copolyamides may also be copolymers having copolyamide blocks and polyether blocks, the copolyamide blocks being blocks of the abovementioned formula 6/ (6, 6) J (6.X) y / (6. Y) .
- copolymers having copolyamide blocks and polyether blocks result from the copolycondensation of polyamide blocks having reactive end groups with polyether blocks having reactive end groups, such as, inter alia:
- copolyamide blocks having carboxylic chain ends are obtained using a diacid chain limiter.
- the copolyamide blocks having diamine chain ends are obtained using a diamine chain limiter.
- the polyether blocks may represent 5 to 85% by weight of the copolymer having copolyamide and polyether blocks.
- the polyether blocks consist of alkylene oxide units. These units may for example be ethylene oxide units, propylene oxide units or tetrahydrofuran units (which leads to polytetramethylene glycol chain sequences) .
- PEG blocks that is to say those consisting of ethylene oxide units
- PPG blocks that is to say those consisting of propylene oxide units
- PTMG blocks that is to say those consisting of tetramethylene glycol units, also called polytetrahydrofuran
- PEG blocks or blocks obtained by the oxyethylation of bisphenols such as for example bisphenol A, may be used. The latter products are disclosed in Patent EP 613 919.
- the proportion of caprolactam by weight may be between 25 and 45%, advantageously between 28 and 42% and preferably between 30 and 40%.
- the proportion of 6.Y by weight may be between 10 and 55%, advantageously between 15 and 50.
- the, copolyamides of the invention are selected from the 6/6,6/6,14 copolyamide, the 6/6,10/6,14 copolyamide, 6/6,6/6,12/6,14 copolyamide. and the 6/6,6/6,10/6,14 copolyamide.
- Example A 6/6,6/6,6/6,14 copolyamide compared with 6/6,6/6,12 copolyamide
- Example B 6/6,10/6,14 copolyamide compared with 6/6,10/6,12 copolyamide
- Example C 6/6,6/6,10/6,14 copolyamide compared with 6/6,6/6,10 copolyamide
- Example D 6/6,6/6,12/6,14 copolyamide compared with 6/6,6/6,12 copolyamide
- copolyamides of the invention are at least equally hydrophobic or more hydrophobic, resulting in a lower water absorption and better resistance of the bond to steam, to chemical solvents and to washing. They melt at lower temperature, which allows more effective and lower-temperature bonding, which therefore saves energy.
- copolyamides were applied by printing them on a cotton non-woven using a powder dot printing device using the standard techniques in the textile coating industry. About 11 to 13 g of copolyamide per m 2 of the cotton non-woven (4557 type supplied by Hansel, Germany) were deposited using a 17-mesh printing stencil. The non-wovens thus coated were bonded to a fabric made up from 45% wool and 55% polyester (Haka) , the bonding being carried out by pressing between hot platens for 15 seconds with a pressing force corresponding to 350 mbar. The temperature of the press platens was adjusted to various values between 100 0 C and 150 0 C.
- Platamid H 005 denotes a 6/6, 6/12-based copolyamide with an MFI of 15 g/10 min (2.16 kg/150°C) and a 118-128 0 C melting range;
- Platamid H 105 denotes a 6/6, 6/12-based copolyamide with an MFI of 2.5 g/10 min (2.16 kg/150°C) , and a 115-127 °C melting range;
- Platamid H 106 denotes a 6/6, 6/11/12-based copolyamide with an MFI of 51 g/10 min (2.16 kg/150 °C) and a 110-118 0 C melting range;
- Vestamelt denotes a 6/MPMD.12/12-based copolyamide with an MFI of 56 g/10 min (2.16 kg/150°C) and a 100-
- the coPA of Example 3 has an MFI of 53 g/10 min
- the coPA of Example 4 has an MFI of 50 g/10 min
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Polyamides (AREA)
Abstract
The present invention relates to copolyamides of formula : 6/(6,6)x/(6.X)y/(6.Y) resulting from the condensation of caprolactam, hexamethylenediamine, optionally adipic acid and a diacid Y, and optionally a diacid X in which: x = 0 or 1, y = 0 or 1, and x+y = 1 or 2; X denotes a diacid HOOC- (CH2)n-COOH in which n is equal to 7, 8, 9 or 10; and Y denotes a diacid HOOC- (CH2)n-COOH in which n is an integer varying from 12 to 16. Advantageously, these copolyamides have a melting point of between 80 °C and 150 °C and an MFI (melt flow index) of between 3 and 80 g/10 min (2.16 kg/150 °C). The present invention also relates to adhesives of the HMA type consisting of the above copolyamides. These adhesives are useful in the textile industry.
Description
LOW-MELTING-POINT COPOLYAMIDES AND THEIR USE AS HOT- MELT ADHESIVES
Field of the invention
The present invention relates to low-melting-point copolyamides and their use as hot-melt adhesives. More precisely, these copolyamides are prepared from long- chain saturated dicarboxylic acids of formula HOOC- (CH2) n""COOH i-n which n is an integer between 11 and 16, these diacids possibly being branched. These copolyamides are useful as adhesives of the HMA (hot- melt adhesive) type, that is to say they are deposited in the molten state on the surfaces to be bonded and then the adhesion is obtained when they return to the solid state by cooling. These adhesives are useful in the textile industry.
Prior art and the technical problem
Patent Application DE OS 1594233 discloses copolyamides resulting either from the condensation of lauryllactam and caprolactam, or from the condensation (i) of lauryllactam and (ii) hexamethylenediamine and adipic acid in stoichiometric proportions, or else from the condensation (i) of lauryllactam, (ii) caprolactam and (iii) hexamethylenediamine and adipic acid in stoichiometric proportions.
Patent Application DE OS 2324160 discloses copolyamides resulting from the condensation of lauryllactam, 11- aminoundecanoic acid, caprolactam and hexamethylenediamine with one or more diacids having from 6 to 13 carbon atoms.
Patent Application EP 627 454 discloses copolyamides resulting from the condensation of at least 10% by weight of lauryllactam or 11-aminoundecanoic acid and hexamethylenediamine with one or more diacids having
from 6 to 12 carbon atoms.
Patent Application EP 1 153 957 discloses copolyamides resulting from the condensation of caprolactam, lauryllactam or 11-aminoundecanoic acid and a diamine with at least two diacids having from 6 to 14 carbon atoms.
Copolyamides have now been found that are at least as hydrophobic as, and often more hydrophobic than, those of the prior art. The advantage is that they have a lower water uptake and, when used as textile adhesives, the bond has a better resistance to steam and to cleaning solvents. Another advantage of these copolyamides is that they melt at lower temperature.
This allows more effective and lower-temperature bonding, which therefore saves energy.
Brief description of the invention
The present invention relates to copolyamides of formula:
6/(6,6)x/(6.X)y/(β.Y) resulting from the condensation of caprolactam, hexamethylenediamine, optionally adipic acid and a diacid Y, and optionally a diacid X in which: x = 0 or 1, y = 0 or 1, and x+y = 1 or 2; X denotes a diacid HOOC- (CH2) n-COOH in which n is equal to 7, 8, 9 or 10; and Y denotes a diacid HOOC- (CH2) n~COOH in which n is an integer varying from 12 to 16 and advantageously 12.
Advantageously, these copolyamides have a melting point of between 800C and 15O0C and an MFI (melt flow index) of between 3 and 80 g/10 min (2.16 kg/150°C) . The melting point is measured by DSC (differential scanning calorimetry) or, according to DIN 53736, Part B (visual determination of the melting point of semicrystalline plastics) optically using a hot stage microscope. They
can be made by the usual process described in the prior art .
The present invention also relates to adhesives of the HMA type consisting of the above copolyamides. These adhesives are useful in the textile industry.
Detailed description of the invention
The copolyamides of the invention may be manufactured using the standard processes described in the prior art.
The copolyamides may also be copolymers having copolyamide blocks and polyether blocks, the copolyamide blocks being blocks of the abovementioned formula 6/ (6, 6) J (6.X) y/ (6. Y) .
The copolymers having copolyamide blocks and polyether blocks result from the copolycondensation of polyamide blocks having reactive end groups with polyether blocks having reactive end groups, such as, inter alia:
1) copolyamide blocks having diamine chain ends with polyoxyalkylene blocks having dicarboxylic chain ends;
2) copolyamide blocks having dicarboxylic chain ends with polyoxyalkylene blocks having diamine chain ends, obtained by cyanoethylation and hydrogenation of aliphatic dihydroxylated α,ω-polyoxyalkylene blocks called polyetherdiols;
3) copolyamide blocks having dicarboxylic chain ends with polyetherdiols, the products obtained being, in this particular case, polyetheresteramides.
The copolyamide blocks having carboxylic chain ends are obtained using a diacid chain limiter.
The copolyamide blocks having diamine chain ends are obtained using a diamine chain limiter.
The polyether blocks may represent 5 to 85% by weight of the copolymer having copolyamide and polyether blocks. The polyether blocks consist of alkylene oxide units. These units may for example be ethylene oxide units, propylene oxide units or tetrahydrofuran units (which leads to polytetramethylene glycol chain sequences) . Thus, PEG blocks, that is to say those consisting of ethylene oxide units, PPG blocks, that is to say those consisting of propylene oxide units, and PTMG blocks, that is to say those consisting of tetramethylene glycol units, also called polytetrahydrofuran, are used. PEG blocks or blocks obtained by the oxyethylation of bisphenols, such as for example bisphenol A, may be used. The latter products are disclosed in Patent EP 613 919.
The proportion of caprolactam by weight may be between 25 and 45%, advantageously between 28 and 42% and preferably between 30 and 40%. The proportion of 6.Y by weight may be between 10 and 55%, advantageously between 15 and 50. These proportions are expressed relative to the mass of the copolyamide and not relative to the mass of the copolyamide blocks and of the optional polyether blocks.
Preferably, the, copolyamides of the invention are selected from the 6/6,6/6,14 copolyamide, the 6/6,10/6,14 copolyamide, 6/6,6/6,12/6,14 copolyamide. and the 6/6,6/6,10/6,14 copolyamide.
Examples
Example A: 6/6,6/6,6/6,14 copolyamide compared with 6/6,6/6,12 copolyamide
Example B: 6/6,10/6,14 copolyamide compared with 6/6,10/6,12 copolyamide
Example C: 6/6,6/6,10/6,14 copolyamide compared with 6/6,6/6,10 copolyamide
Example D: 6/6,6/6,12/6,14 copolyamide compared with 6/6,6/6,12 copolyamide
The copolyamides of the invention are at least equally hydrophobic or more hydrophobic, resulting in a lower water absorption and better resistance of the bond to steam, to chemical solvents and to washing. They melt at lower temperature, which allows more effective and lower-temperature bonding, which therefore saves energy.
Example F: Application examples
The copolyamides were applied by printing them on a cotton non-woven using a powder dot printing device using the standard techniques in the textile coating industry. About 11 to 13 g of copolyamide per m2 of the cotton non-woven (4557 type supplied by Hansel, Germany) were deposited using a 17-mesh printing stencil. The non-wovens thus coated were bonded to a fabric made up from 45% wool and 55% polyester (Haka) , the bonding being carried out by pressing between hot platens for 15 seconds with a pressing force corresponding to 350 mbar. The temperature of the press platens was adjusted to various values between 1000C and 1500C. Thus, a series of laminates (copolyamide- coated cotton non-woven bonded to the wool/polyester fabric by pressing) produced at various pressing temperatures was obtained, and these were then cut into specimens 5 cm in width. The tear strength in N/5 cm of these specimens was measured according to DIN 54310 standard (the bond strength test was performed on an Instron tensile testing machine, the pull rate being 350 mm/min, the specimen width being 5 cm and the gauge
length being 25 cm) . All the tests were carried out at room temperature. The measurements were made on four series of laminates, namely those that had just been manufactured and underwent no treatment, those that underwent three washings at 4O0C, those that underwent three washings at 600C and those that underwent three washings at 900C.
The results are given in the following table, in which: the particle size distribution is denoted by PTA
170/20 which means that 80% of the distribution is made up by powder particles' finer than 170 μm, but the powder contains no more than 20% of particles finer than 80 μm; Platamid H 005 denotes a 6/6, 6/12-based copolyamide with an MFI of 15 g/10 min (2.16 kg/150°C) and a 118-1280C melting range;
Platamid H 105 denotes a 6/6, 6/12-based copolyamide with an MFI of 2.5 g/10 min (2.16 kg/150°C) , and a 115-127 °C melting range;
Platamid H 106 denotes a 6/6, 6/11/12-based copolyamide with an MFI of 51 g/10 min (2.16 kg/150 °C) and a 110-1180C melting range; and
Vestamelt denotes a 6/MPMD.12/12-based copolyamide with an MFI of 56 g/10 min (2.16 kg/150°C) and a 100-
1060C melting range. The particle size distribution of this grade is given by the term P 816/20, which means that the powder is made up from 80-160 μm particles
(with 20% < 80 μm) .
The coPA of Example 3 has an MFI of 53 g/10 min
(2.16 kg/150°C) .
The coPA of Example 4 has an MFI of 50 g/10 min
(2.16 kg/150°C) .
Application in "powder dot" form
00
_ g -
Claims
1. Copolyamides of formula:
6/(6, 6)x/(6.X)y/(6.Y) resulting from the condensation of caprolactam, hexamethylenediamine, optionally adipic acid and a diacid Y, and optionally a diacid X in which: x = 0 or 1, y = 0 or 1, and x+y = 1 or 2; X denotes a diacid HOOC- (CH2) n-COOH in which n is equal to 7, 8, 9 or 10; and
Y denotes a diacid HOOC- (CH2) n-COOH in which n is an integer varying from 12 to 16.
2. Copolyamides according to Claim 1, in which the proportion of caprolactam is between 25 and 45% by weight.
3. Copolyamides according to Claim 2, in which the proportion of caprolactam is between 28 and 42% by weight.
4. Copolyamides according to Claim 3, in which the proportion of caprolactam is between 30 and 40% by weight.
5. Copolyamides according to any one of the preceding claims, in which X denotes a diacid HOOC- (CH2) n-COOH in which n is equal to 7, 8, 9 or 10.
6. Copolyamides according to any one of the preceding claims, in which Y denotes a diacid HOOC- (CH2) n-COOH in which n is equal to 12.
7. Adhesives of the HMA (hot-melt adhesive) type consisting of copolyamides according to any one of the preceding claims.
8. Use of the adhesives of Claim 8 in the textile industry.
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0503065A FR2883878B1 (en) | 2005-03-30 | 2005-03-30 | COPOLYAMIDE AT LOW TEMPERATURE OF FUSION AND ITS USE AS THERMOFUSIBLE ADHESIVE |
| FR05/03065 | 2005-03-30 | ||
| US68679305P | 2005-06-02 | 2005-06-02 | |
| US60/686,793 | 2005-06-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO2006102975A1 true WO2006102975A1 (en) | 2006-10-05 |
Family
ID=36320184
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/EP2006/002195 WO2006102975A1 (en) | 2005-03-30 | 2006-02-21 | Low-melting-point copolyamides and their use as hot-melt adhesives |
Country Status (1)
| Country | Link |
|---|---|
| WO (1) | WO2006102975A1 (en) |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2934867A1 (en) * | 2008-08-08 | 2010-02-12 | Arkema France | Use of a composition comprising carbon nanotubes and copolyamide obtained from different starting product of e.g. lactams and amino carboxylic acids as electrically conductive adhesive composition |
| EP2338928A1 (en) * | 2009-12-17 | 2011-06-29 | Ems-Patent Ag | Binding fibre for fixing flat materials containing natural fibres |
| EP2157149A3 (en) * | 2008-08-07 | 2012-10-17 | Arkema France | Use of a dispersion of carbon nanotubes in a copolyamide as a conductive adhesive composition |
| US20130048136A1 (en) * | 2011-08-29 | 2013-02-28 | E I Du Pont De Nemours And Company | Copolyamide compositions derived from triacylglycerides |
| CN103484053A (en) * | 2013-10-16 | 2014-01-01 | 上海天洋热熔胶有限公司 | Preparation method of hot-melt adhesive for conductive fabrics |
| CN103525357A (en) * | 2013-10-23 | 2014-01-22 | 上海天洋热熔胶有限公司 | Preparation method of amino inhibited polyamide hot melt adhesive |
| CN109970969A (en) * | 2019-04-10 | 2019-07-05 | 山东广垠新材料有限公司 | A kind of preparation method of ternary polymerization low melting point nylon |
| CN114108122A (en) * | 2021-10-18 | 2022-03-01 | 浙江古纤道股份有限公司 | Preparation method of low-melting-point nylon fiber |
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| US3883485A (en) * | 1973-05-12 | 1975-05-13 | Plate Bonn Gmbh | Copolyamides containing caprolactam, lauriclactam and hexamethylene diamine adipate |
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| US4093492A (en) * | 1973-05-12 | 1978-06-06 | Plate Bonn Gesellschaft Mit Beschrankter Haftung | Copolyamides containing caprolactam, lauriclactam and 11-aminoundecanoic acid |
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| US5459230A (en) * | 1993-05-29 | 1995-10-17 | Elf Autochem Deutschland Gmbh | Copolyamide melt adhesives for heat sealing textiles |
| US20020022670A1 (en) * | 2000-05-10 | 2002-02-21 | Ems-Chemie Ag | Low-melting copolyamide and their use as hot-melt adhesives |
| US20020043333A1 (en) * | 2000-03-24 | 2002-04-18 | Atofina | Copolymers containing polyamide blocks and polyether blocks based on ethoxylated amines |
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2006
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| US3883485A (en) * | 1973-05-12 | 1975-05-13 | Plate Bonn Gmbh | Copolyamides containing caprolactam, lauriclactam and hexamethylene diamine adipate |
| US4030957A (en) * | 1973-05-12 | 1977-06-21 | Plate Bonn Gesellschaft Mit Beschrankter Haftung | Copolyamides containing caprolactam, lauriclactam and hexamethylene diamine adipate |
| US4093492A (en) * | 1973-05-12 | 1978-06-06 | Plate Bonn Gesellschaft Mit Beschrankter Haftung | Copolyamides containing caprolactam, lauriclactam and 11-aminoundecanoic acid |
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Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2157149A3 (en) * | 2008-08-07 | 2012-10-17 | Arkema France | Use of a dispersion of carbon nanotubes in a copolyamide as a conductive adhesive composition |
| FR2934867A1 (en) * | 2008-08-08 | 2010-02-12 | Arkema France | Use of a composition comprising carbon nanotubes and copolyamide obtained from different starting product of e.g. lactams and amino carboxylic acids as electrically conductive adhesive composition |
| EP2338928A1 (en) * | 2009-12-17 | 2011-06-29 | Ems-Patent Ag | Binding fibre for fixing flat materials containing natural fibres |
| US8956986B2 (en) | 2009-12-17 | 2015-02-17 | Ems-Patent Ag | Binding fiber for bonding of flat material containing natural fibers |
| US20130048136A1 (en) * | 2011-08-29 | 2013-02-28 | E I Du Pont De Nemours And Company | Copolyamide compositions derived from triacylglycerides |
| CN103484053A (en) * | 2013-10-16 | 2014-01-01 | 上海天洋热熔胶有限公司 | Preparation method of hot-melt adhesive for conductive fabrics |
| CN103525357A (en) * | 2013-10-23 | 2014-01-22 | 上海天洋热熔胶有限公司 | Preparation method of amino inhibited polyamide hot melt adhesive |
| CN109970969A (en) * | 2019-04-10 | 2019-07-05 | 山东广垠新材料有限公司 | A kind of preparation method of ternary polymerization low melting point nylon |
| CN109970969B (en) * | 2019-04-10 | 2021-06-22 | 山东广垠新材料有限公司 | Preparation method of terpolymer low-melting-point nylon |
| CN114108122A (en) * | 2021-10-18 | 2022-03-01 | 浙江古纤道股份有限公司 | Preparation method of low-melting-point nylon fiber |
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