WO2019066200A1 - Procédé pour la préparation de polyamide et polyamide ainsi préparé - Google Patents
Procédé pour la préparation de polyamide et polyamide ainsi préparé Download PDFInfo
- Publication number
- WO2019066200A1 WO2019066200A1 PCT/KR2018/007009 KR2018007009W WO2019066200A1 WO 2019066200 A1 WO2019066200 A1 WO 2019066200A1 KR 2018007009 W KR2018007009 W KR 2018007009W WO 2019066200 A1 WO2019066200 A1 WO 2019066200A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- polyamide
- carbon atoms
- formula
- represented
- alkylene group
- Prior art date
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- 0 CC(C)(CCOC(C)(C)C(*1)*1OC(C)(C)*N)O*N Chemical compound CC(C)(CCOC(C)(C)C(*1)*1OC(C)(C)*N)O*N 0.000 description 2
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
- C08G69/14—Lactams
-
- 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
-
- 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
- D01F6/78—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from copolycondensation products
- D01F6/80—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from copolycondensation products from copolyamides
Definitions
- the present invention relates to a method for producing polyamide capable of producing a polyamide excellent in water absorption rate and capable of easily forming a fiber and having excellent radial extensibility, and a polyamide produced by using the same.
- Nylon 6 fiber has advantages such as excellent stiffness, elastic recovery rate and dyeability. However, most synthetic fiber including nylon 6 fiber has a low water absorption property. Cotton, which is a natural fiber, It has a good touch, but it has a drawback that it is very slow in moisture drying rate, extremely low in UV blocking property, and expensive in price.
- the water absorbency of the crystalline polymer depends on various factors such as the type of hydrophilic functional group, the crystal structure, and the degree of crystallization.
- nylon which is one of the crystalline polymers
- Nylon 3 fibers with a low carbon number or nylon 4 fibers have been extensively studied.
- the nylon 4 fiber has an excellent water absorbency (moisture content) similar to that of a natural fiber, due to an increase in hydrophilicity due to a smaller number of carbon atoms in the repeating unit than in the nylon 6, and the strength is similar to that of the conventional nylon 6.
- nylon 4 fibers were thought to be synthesized by condensation of GABA (gamma amino butyric acid), which is a raw material monomer, by heating and dehydration, but since the monomers themselves are cyclized to 2-pyrrolidone Line polymer could not be obtained. Furthermore, since 2-pyrrolidone is a lactam of 5-membered ring, it is thermally stable and the ring-opening polymerization is not easy.
- GABA gamma amino butyric acid
- Ney et al. Were dehydrated by heating under reduced pressure at 90 ° C to 120 ° C using potassium hydroxide and heated at 160 ° C under a nitrogen stream to carry out ring-opening polymerization of 2-pyrrolidone, Respectively.
- new catalyst materials and polymerization techniques have been developed for the purpose of high molecular weight, polydispersity control and simplification of the production process from the 1950s to the 1990s.
- the poly (2-pyrrolidone) resin synthesized in 1953 has superior absorbability and rigidity due to the small number of lipophilic carbon atoms per repeating unit in its structure.
- the poly (2-pyrrolidone) resin synthesized in 1953 has superior absorbability and rigidity due to the small number of lipophilic carbon atoms per repeating unit in its structure.
- nylon 4 has a melting point of 265 ⁇ , higher than nylon 6, and a pyrolysis temperature of 260 ⁇ .
- nylon 4 is thermally decomposed before reaching the melting point, so that fiber formation by continuous spinning is impossible.
- Patent Document 1 Japanese Patent Application Laid-Open No. 2001-348427 (published Dec. 18, 2001)
- Patent Document 2 Japanese Patent Application Laid-Open No. 2009-256610 (published on November 5, 2009)
- An object of the present invention is to provide a method for producing a polyamide excellent in water absorption rate of polyamide and capable of facilitating fiber formation and excellent in spinnability, and a polyamide produced using the method.
- a first reactant includes a first nylon salt represented by Formula 1 below;
- As the second reactant an amino acid or a lactam;
- X 1 and Y 1 are each independently an alkylene group having 4 carbon atoms
- Y is an alkylene group having 3 to 6 carbon atoms
- R 1 , R 2, and R 3 are each an alkylene group having 3 to 6 carbon atoms.
- X is an integer of 1 to 3
- y is an integer of 2 to 39
- z is an integer of 1 to 3.
- the first nylon salt may be prepared by reacting a diamine represented by the following formula (1a) with a dicarboxylic acid represented by the following formula (1b).
- X and Y each independently represent an alkylene group having 3 to 6 carbon atoms.
- the amino acid may be represented by the following formula (2).
- V is an alkylene group having 2 to 12 carbon atoms.
- amino acid is selected from the group consisting of 3-aminopropanoic acid, 4-aminobutanoic acid, 6-aminohexanoic acid or 6-aminocaproic acid, (12-Aminododecanoic acid), and mixtures thereof.
- the lactam may be represented by the following formula (3).
- W is an alkylene group having 2 to 12 carbon atoms.
- the lactam may be selected from the group consisting of 2-pyrrolidone, 2-piperidinone, epsilon -caprolactam, lauryl lactam, and mixtures thereof. Lt; / RTI >
- the reaction may be performed by stirring the first reactant to the third reactant at 20 ° C to 120 ° C for 0.5 hours to 4 hours and reacting at 200 ° C to 260 ° C for 2 hours to 6 hours.
- a resin composition comprising, as the first repeating unit, a repeating unit derived from a first nylon salt represented by the following formula (1): As the second repeating unit, a repeating unit derived from an amino acid or a lactam; And a repeating unit derived from an elastomer salt prepared by the reaction of a diamine represented by the following formula (5a) and a dicarboxylic acid represented by the following formula (5b) as a third repeating unit.
- X 1 and Y 1 are each independently an alkylene group having 4 carbon atoms
- Y is an alkylene group having 3 to 6 carbon atoms
- R 1 , R 2, and R 3 are each an alkylene group having 3 to 6 carbon atoms.
- X is an integer of 1 to 3
- y is an integer of 2 to 39
- z is an integer of 1 to 3.
- the polyamide comprises 10 to 55% by weight of the first repeating unit, 20 to 70% by weight of the second repeating unit, and 10 to 50% by weight of the third repeating unit, By weight.
- the polyamide has an intrinsic viscosity ( ⁇ ) of from 0.4 dl / g to 2.2 dl / g as measured at 30 ⁇ in m-cresol, a melting point of from 150 ⁇ to 280 ⁇ , a process condition water absorption rate after fiberization of from 6% 15%, and the fiber strength may be 2.0 g / d to 6.0 g / d.
- an alkylene group can be represented by a general formula -C n H 2n - with a divalent atomic group generated by excluding two hydrogen atoms bonded to two other carbon atoms in an aliphatic saturated hydrocarbon,
- the alkylene group may be linear or branched.
- a method for preparing a polyamide comprising: reacting a first nylon salt represented by the following general formula (1); As the second reactant, an amino acid or a lactam; And reacting an elastomer salt prepared by the reaction of a diamine represented by the following formula (5a) and a dicarboxylic acid represented by the following formula (5b) as a third reactant.
- X 1 and Y 1 are each independently an alkylene group having 4 carbon atoms
- Y is an alkylene group having 3 to 6 carbon atoms
- R 1 , R 2, and R 3 are each an alkylene group having 3 to 6 carbon atoms.
- X is an integer of 1 to 3
- y is an integer of 2 to 39
- z is an integer of 1 to 3.
- the first nylon salt represented by Formula 1 as the first reactant may be prepared by reacting a diamine represented by the following Formula 1a with a dicarboxylic acid represented by the following Formula 1b.
- X and Y each independently represent an alkylene group having 4 carbon atoms.
- the diamine may be 1,4-diaminobutane
- the dicarboxylic acid may be adipic acid
- the preparation of the first nylon salt may be carried out at 20 ⁇ to 80 ⁇ under a nitrogen atmosphere. If the production temperature of the first nylon salt is less than 20 ° C, the nylon salt may not be formed well, and if it exceeds 80 ° C, polymerization control may be difficult.
- the reaction for producing the first nylon salt may be preferably carried out under a moisture condition.
- the water content is in the range of 30% by weight to 80% by weight with respect to the total weight of the raw material to be added to produce the first nylon salt.
- the content of water is less than 30% by weight, there is a fear that the salt is not uniformly produced, and the conductivity of the salt solution or the salt dispersion becomes high, which may be difficult to handle.
- the content of water exceeds 80% by weight, the process time becomes long and the yield of polyamide may decrease.
- the amino acid may be represented by the following formula (2).
- V is an alkylene group having 2 to 12 carbon atoms.
- the amino acid may be 3-aminopropanoic acid, 4-aminobutanoic acid, 6-aminohexanoic acid or 6-aminocaproic acid, (12-aminododecanoic acid), and mixtures thereof.
- the lactam may be represented by the following formula (3).
- W is an alkylene group having 2 to 12 carbon atoms.
- the lactam is preferably selected from the group consisting of 2-pyrrolidone, 2-piperidinone, epsilon -caprolactam, lauryl lactam, and mixtures thereof. Lt; / RTI > group.
- the elastomer salt may be prepared by reacting a diamine represented by the following formula (5a) with a dicarboxylic acid represented by the following formula (5b).
- Y is an alkylene group having 3 to 6 carbon atoms, and more specifically, Y may be an alkylene group having 4 to 6 carbon atoms.
- R 1 , R 2 and R 3 is independently an alkylene group having 3 to 6 carbon atoms, specifically an alkylene group having 3 or 4 carbon atoms.
- R 1 , R 2 and R 3 may independently be a propylene group, an isopropylene group, a butylene group, an isobutylene group, a 2,3-butylene group, or the like.
- x, y and z are the number of repeating units of the diamine represented by the formula (5a). Wherein x is an integer of 1 to 3, y is an integer of 2 to 39, and z is an integer of 1 to 3, more specifically, x is an integer of 2 to 3, and y is an integer of 9 to 13 And z may be an integer of 2 to 3.
- the diamine represented by Formula 5a is an aliphatic polyether and forms a soft segment. Specific examples thereof include polyoxyethylene diamine, polyoxypropylene diamine, polyoxytetramethylenediamine, polyoxypropylene / ethylene / Propylene diamine (polyoxypropylene / ethylene / propylene diamine), and mixtures thereof.
- the dicarboxylic acid represented by Formula 5b may be any one selected from the group consisting of adipic acid, glutaric acid, pimelic acid and suberic acid.
- the method for producing the elastomer salt is the same as the method for producing the first nylon salt except for using the compound represented by Chemical Formula 5a and the compound represented by Chemical Formula 5b, and therefore, a repetitive description thereof will be omitted.
- the elastomeric salt may have a weight average molecular weight of from 50,000 g / mol to 150,000 g / mol, and specifically from 60,000 g / mol to 120,000 g / mol. When the weight average molecular weight of the elastomer salt is within the above range, stable polymerization reactivity and physical properties of the elastomer salt can be obtained.
- the reaction of the first reactant to the third reactant may be performed by stirring the first reactant to the third reactant at 20 ° C to 120 ° C for 0.5 hours to 4 hours and reacting the reactant at 200 ° C to 260 ° C for 2 hours to 6 hours Specifically, the first reactant to the third reactant may be stirred at 50 ° C to 80 ° C for 1 hour to 3 hours, and reacted at 200 ° C to 260 ° C for 3 hours to 6 hours.
- the stirring When the stirring is performed at a temperature lower than 20 ° C or less than 0.5 hour, the reaction product may not be dispersed solidified due to solidification, so that a polyamide having uniform physical properties may not be produced.
- the stirring is performed at a temperature higher than 120 ° C. or more than 4 hours
- the reaction of polyamides 4 and 6 preferentially causes non-uniformity of reaction, and polyamides having uniform physical properties may not be produced.
- the polymerization reaction may be insufficient and a polymer of sufficient size may not be produced.
- the reaction is conducted at a temperature higher than 260 ° C or more than 6 hours, polymerization and decomposition occur simultaneously, Is accompanied by a sharp rise in the molecular weight distribution, and thus a polymer having a sufficient size can not be obtained.
- the polyamide may further include a second nylon salt represented by the following general formula (4) as a fourth reactant.
- X 2 and Y 2 each independently represent an alkylene group having 3 to 6 carbon atoms.
- the second nylon salt can also be prepared by reacting the diamine represented by the above formula (1a) with the dicarboxylic acid of the above formula (1b).
- each of X and Y is independently an alkylene group having 3 to 6 carbon atoms.
- the diamine may be 1,3-diaminopropane, 1,4-diaminobutane, 1,5-diaminopentane, 1,5- diaminopentane, 1,6-diaminohexane, and the like.
- the dicarboxylic acid may be any one selected from the group consisting of adipic acid, glutaric acid, pimelic acid, and suberic acid.
- the polyamide may be further added with an antioxidant to impart antioxidant properties at a high temperature in the step of reacting the first reactant to the third reactant.
- the antioxidant is to impart antioxidant properties to the polyamide during spinning at a high temperature.
- the antioxidant may be a hindered phenol antioxidant, a diphenylamine antioxidant, a metal complex oxide antioxidant, a hindered amine light guide Tablets, and mixtures thereof, and may be any one selected from the group consisting of hindered phenol-based antioxidants.
- the method for producing a polyamide according to the present invention as described above is characterized in that the reaction material used in the production of the polyamide is obtained from an elastomer salt prepared by the reaction of the diamine represented by the formula 5a and the dicarboxylic acid represented by the following formula 5b , It is possible to produce a polyamide which is capable of easily forming fibers while having excellent water absorption rate and is excellent in radial stretchability.
- the polyamide according to one embodiment is a first recurring unit comprising a repeating unit derived from a first nylon salt represented by the following general formula (1);
- X 1 and Y 1 are each independently an alkylene group having 4 carbon atoms
- Y is an alkylene group having 3 to 6 carbon atoms
- R 1 , R 2, and R 3 are each an alkylene group having 3 to 6 carbon atoms.
- X is an integer of 1 to 3
- y is an integer of 2 to 39
- z is an integer of 1 to 3.
- the repeating unit derived from the first nylon salt represented by Formula 1 may have a structure of - [-NH- (CH 2 ) 4 -NH-CO- (CH 2 ) 4 -CO-] - have.
- the polyamide comprises 10 to 55% by weight of the first repeating unit, 20 to 70% by weight of the second repeating unit, and 10 to 50% by weight of the third repeating unit, Preferably 30 to 55% by weight of the first repeating unit, 25 to 60% by weight of the second repeating unit, and 10 to 40% by weight of the third repeating unit, By weight.
- the polyamide can easily form fibers while having excellent water absorption, and is excellent in radial extensibility.
- the regularity of the basic structure of the polyamide may be insufficient and the crystallization may be irregular, resulting in insufficient fiber-forming property.
- the content of the polyamide The crystallization speed is too high, so that the stretching property is poor during the production process, and fiber formation may be insufficient,
- the degree of reactivity may be decreased, the melting temperature may be increased, and the crystallization speed may be accelerated. As a result, the elongation properties may deteriorate and fiber formation may be insufficient. It can not be done.
- the content of the third repeating unit is less than 10% by weight, a sufficient moisture content may not be obtained and there may be a problem in the flexibility of the produced polyamide.
- the content of the third repeating unit is more than 50% by weight, , Crystallization is irregularly formed, which may cause problems such as fiber formability, heat resistance and compatibility.
- the polyamide may have an intrinsic viscosity ( ⁇ ) of from 0.4 dl / g to 2.2 dl / g as measured at m-cresol at 30 ° C and a melting point of 150 ° C to 280 ° C
- ⁇ intrinsic viscosity
- the process condition water absorption rate after fiberization may be 6 wt% to 15 wt%
- the strength of the fibers may be 2.0 g / d to 6.0 g / d.
- Diaminobutane (728 g) dissolved in 5000 ml of ethanol was added 1207 g of adipic acid to the ethanol solution of 1,4-diaminobutane and reacted at 25 ° C under a nitrogen atmosphere to give a first nylon salt .
- R 1 and R 3 are isopropylene groups, x is 2, and y is 15, wherein a weight average molecular weight of 900 g / mol is polyethylene oxide and polypropylene oxide as main chains and the terminal is a diamine , And z is 2), and then adding thereto 2008 g of adipic acid (Y in the above formula (5b) is butylene group), and the mixture was reacted at 50 ° C under a nitrogen atmosphere An elastomeric salt was prepared.
- the polymer was discharged by pressurization of 2 kg / cm 2.
- the polymer was prepared as a chip.
- the polymer was washed with water at 95 ° C for 24 hours to remove unreacted materials, and then vacuum dried at 100 ° C for 20 hours to obtain poly Amide copolymer resin.
- a polyamide copolymer resin was prepared in the same manner as in Example 1 except that 3840 g of polyoxypropylene / ethylene / propylene diamine and 623 g of adipic acid were used in Example 1.
- R 1 to R 3 in the formula (5a) are isopropylene groups, x is 2, y is 15, and z is 2.
- a polyamide copolymer resin was prepared in the same manner as in Example 1 except that 5120 g of polyoxypropylene / ethylene / propylene diamine and 832 g of adipic acid were used in Example 1.
- R 1 to R 3 in the formula (5a) are isopropylene groups, x is 2, y is 15, and z is 2.
- a polyamide copolymer resin was prepared in the same manner as in Example 1 except that the elastomer salt was not added.
- a polyamide copolymer resin was prepared in the same manner as in Example 1 except that 5 kg of? -Caprolactam was used in Example 1.
- Example 1 The procedure of Example 1 was repeated, except that 3.5 kg of? -Caprolactam, 1.5 kg of polyoxypropylene / ethylene / propylene diamine and 244 g of adipic acid were used in Example 1 to prepare a polyamide copolymer resin .
- R 1 to R 3 in the formula (5a) are isopropylene groups, x is 2, y is 15, and z is 2.
- a polyamide copolymer resin was prepared in the same manner as in Example 1 except that 3.5 kg of? -Caprolactam, 1.5 kg of polyoxyethylene diamine and 219 g of adipic acid were used in Example 1.
- a polyamide copolymer resin was prepared in the same manner as in Example 1 except that 6400 g of polyoxypropylene / ethylene / propylene diamine and 1039 g of adipic acid were used in Example 1.
- R 1 to R 3 in the formula (5a) are isopropylene groups, x is 2, y is 15, and z is 2.
- Tensile strength The tensile strength of the filament in the standard state is measured by stretching at a gripping distance of 20 cm and a tensile speed of 20 ⁇ 2 cm / min (KS K 0412).
- Moisture content (O - D) / D * 100
- Comparative Example 2 it was found that the radioactive and tensile strengths were good but the moisture content was measured to be less than 5% as it included only the first reactant. In the case of Comparative Example 3, It can be seen that the radioactivity is excellent but the water content is inferior. In the case of Comparative Example 4, it can be understood that the irradiation is not carried out by including only the third reactant.
- the present invention relates to a process for producing a polyamide and a polyamide produced by using the process.
- the process for producing a polyamide according to the present invention comprises the steps of: preparing a polyamide having excellent water absorption, can do.
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- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
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Abstract
La présente invention concerne un procédé pour la préparation d'un polyamide et un polyamide ainsi préparé. Le procédé pour la préparation d'un polyamide comprend l'étape consistant à faire réagir un premier sel de nylon en tant que premier réactif, un acide aminé ou un lactame en tant que deuxième réactif et un sel d'élastomère en tant que troisième réactif. Selon le procédé pour la préparation d'un polyamide, il est possible de préparer un polyamide qui peut facilement être mis sous forme d'une fibre et qui a un excellent taux d'absorption d'humidité et une excellente propriété de filage-étirage.
Priority Applications (1)
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CN201880051231.1A CN111032734B (zh) | 2017-09-26 | 2018-06-21 | 聚酰胺的制备方法以及利用该方法制备的聚酰胺 |
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KR10-2017-0124280 | 2017-09-26 | ||
KR1020170124280A KR102339256B1 (ko) | 2017-09-26 | 2017-09-26 | 폴리아마이드의 제조 방법 및 이를 이용하여 제조된 폴리아마이드 |
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WO2019066200A1 true WO2019066200A1 (fr) | 2019-04-04 |
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PCT/KR2018/007009 WO2019066200A1 (fr) | 2017-09-26 | 2018-06-21 | Procédé pour la préparation de polyamide et polyamide ainsi préparé |
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KR (1) | KR102339256B1 (fr) |
CN (1) | CN111032734B (fr) |
WO (1) | WO2019066200A1 (fr) |
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KR102267621B1 (ko) | 2019-12-30 | 2021-06-21 | 다이텍연구원 | 나일론 4,6 섬유의 염색 방법 |
Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH11322974A (ja) * | 1998-05-14 | 1999-11-26 | Toyobo Co Ltd | 耐ピンホール性が優れたポリアミド系フイルム |
JP2002166512A (ja) * | 2000-11-30 | 2002-06-11 | Toyobo Co Ltd | 耐屈曲疲労性が優れたポリアミド系フィルム |
CN1826369A (zh) * | 2003-06-26 | 2006-08-30 | 罗狄亚聚酰胺中间体公司 | 基于聚酰胺的球形颗粒的制备方法 |
WO2009012607A2 (fr) * | 2007-07-25 | 2009-01-29 | Ems-Patent Ag | Élastomères de polyamide transparents |
KR20150042487A (ko) * | 2013-10-11 | 2015-04-21 | 코오롱인더스트리 주식회사 | 폴리아마이드의 제조방법 및 이를 이용하여 제조된 폴리아마이드 |
KR20170002207A (ko) * | 2015-06-29 | 2017-01-06 | 코오롱인더스트리 주식회사 | 폴리아마이드계 엘라스토머 조성물 및 그 성형품, 그리고 고분자 필름 |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5030710A (en) * | 1990-04-10 | 1991-07-09 | Texaco Chemical Company | Nylon-6 modified with low molecular weight polyethylene glycol diamines |
JP2001348427A (ja) | 2000-06-09 | 2001-12-18 | Kuraray Co Ltd | ポリアミドの製造方法 |
JP5280889B2 (ja) | 2008-03-28 | 2013-09-04 | 東レ株式会社 | 芳香族ポリアミドの製造方法 |
-
2017
- 2017-09-26 KR KR1020170124280A patent/KR102339256B1/ko active IP Right Grant
-
2018
- 2018-06-21 CN CN201880051231.1A patent/CN111032734B/zh not_active Expired - Fee Related
- 2018-06-21 WO PCT/KR2018/007009 patent/WO2019066200A1/fr active Application Filing
Patent Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH11322974A (ja) * | 1998-05-14 | 1999-11-26 | Toyobo Co Ltd | 耐ピンホール性が優れたポリアミド系フイルム |
JP2002166512A (ja) * | 2000-11-30 | 2002-06-11 | Toyobo Co Ltd | 耐屈曲疲労性が優れたポリアミド系フィルム |
CN1826369A (zh) * | 2003-06-26 | 2006-08-30 | 罗狄亚聚酰胺中间体公司 | 基于聚酰胺的球形颗粒的制备方法 |
WO2009012607A2 (fr) * | 2007-07-25 | 2009-01-29 | Ems-Patent Ag | Élastomères de polyamide transparents |
KR20150042487A (ko) * | 2013-10-11 | 2015-04-21 | 코오롱인더스트리 주식회사 | 폴리아마이드의 제조방법 및 이를 이용하여 제조된 폴리아마이드 |
KR20170002207A (ko) * | 2015-06-29 | 2017-01-06 | 코오롱인더스트리 주식회사 | 폴리아마이드계 엘라스토머 조성물 및 그 성형품, 그리고 고분자 필름 |
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Publication number | Publication date |
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KR20190035258A (ko) | 2019-04-03 |
KR102339256B1 (ko) | 2021-12-13 |
CN111032734B (zh) | 2022-07-26 |
CN111032734A (zh) | 2020-04-17 |
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