JP6104908B2 - アラミド共重合体の製造方法 - Google Patents
アラミド共重合体の製造方法 Download PDFInfo
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- 238000004519 manufacturing process Methods 0.000 title claims description 7
- 239000004760 aramid Substances 0.000 title description 2
- 229920003235 aromatic polyamide Polymers 0.000 title description 2
- 229920000642 polymer Polymers 0.000 claims description 50
- 150000003839 salts Chemical class 0.000 claims description 27
- LXEJRKJRKIFVNY-UHFFFAOYSA-N terephthaloyl chloride Chemical compound ClC(=O)C1=CC=C(C(Cl)=O)C=C1 LXEJRKJRKIFVNY-UHFFFAOYSA-N 0.000 claims description 26
- 239000002904 solvent Substances 0.000 claims description 23
- 239000000203 mixture Substances 0.000 claims description 21
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 claims description 19
- 229910017053 inorganic salt Inorganic materials 0.000 claims description 11
- 239000003960 organic solvent Substances 0.000 claims description 11
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000001450 anions Chemical class 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical group CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 46
- 239000000835 fiber Substances 0.000 description 42
- 238000000034 method Methods 0.000 description 41
- 239000000243 solution Substances 0.000 description 19
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 17
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 14
- 239000002585 base Substances 0.000 description 14
- 238000006386 neutralization reaction Methods 0.000 description 14
- 229920001577 copolymer Polymers 0.000 description 13
- 238000004140 cleaning Methods 0.000 description 12
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 12
- 238000009987 spinning Methods 0.000 description 11
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 238000005406 washing Methods 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 239000000178 monomer Substances 0.000 description 7
- 239000002253 acid Substances 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 238000001035 drying Methods 0.000 description 5
- 239000002245 particle Substances 0.000 description 5
- 238000006116 polymerization reaction Methods 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000013626 chemical specie Substances 0.000 description 2
- 238000010924 continuous production Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 238000000227 grinding Methods 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 230000001788 irregular Effects 0.000 description 2
- 230000003472 neutralizing effect Effects 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000010998 test method Methods 0.000 description 2
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 2
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 239000011260 aqueous acid Substances 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 230000001276 controlling effect Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000002596 correlated effect Effects 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- -1 halogen anion Chemical class 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 125000003232 p-nitrobenzoyl group Chemical group [N+](=O)([O-])C1=CC=C(C(=O)*)C=C1 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 229920006027 ternary co-polymer Polymers 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- 238000002166 wet spinning Methods 0.000 description 1
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
- C08G69/04—Preparatory processes
-
- 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
- C08G69/26—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids derived from polyamines and polycarboxylic acids
- C08G69/32—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids derived from polyamines and polycarboxylic acids from aromatic diamines and aromatic dicarboxylic acids with both amino and carboxylic groups aromatically bound
-
- 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
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/18—Polybenzimidazoles
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyamides (AREA)
- Artificial Filaments (AREA)
Description
Vinh=ln(Vrel)/C
式中、lnは自然対数関数であり、Cはポリマー溶液の濃度である。Vrelは、無名数の比であり、従ってVinhは、通常、グラム当たりのデシリットル(「dl/g」)として、濃度の逆数の単位で表される。
本明細書で使用する場合、化学種の「残基」という用語は、特定の反応式中の化学種から得られる生成物またはその後の配合物もしくは化学製品である部分を指し、その部分が実際にその化学種から得られるかどうかは関係ない。従って、p−フェニレンジアミンの残基を含む共重合体は、式:
固有粘度は、ポリマーが濃度96重量%の濃硫酸にポリマー濃度(C)0.5g/dlおよび温度25℃で溶解している溶液を使用して測定することができる。次いで、固有粘度をln(tpoly/tsolv)/C(式中、tpolyはポリマー溶液の滴下時間であり、tsolvは純粋な溶媒の滴下時間である)として算出する。
バスケット攪拌機、窒素入口/出口を備えた1リットルの反応釜に、NMP/CaCl2プレミックス(8.3重量%(塩の重量/塩と溶媒の全重量))83.709グラム、NMP(N−メチル−2−ピロリドン)109.620グラム、DAPBI硫酸塩14.123グラム(0.044モル)、およびPPD(p−フェニレンジアミン)2.031グラム(0.019モル)を添加し、室温で30分間撹拌した。内容物を氷水浴中で撹拌し、混合物を10℃未満に冷却した。TCl(テレフタロイルクロライド)4.459グラム(0.022モル)を全部一度に添加し、5分間撹拌した。この時点で、DAPBIがTClと反応したため、溶液は透明になった。氷水浴を取り除いた。TCl、8.281グラム(0.041モル)を全部一度に添加し、撹拌した。溶液は非常に粘度が高くなり、約7分でゲル化し、最後に約10分で粉々になった。得られたクラムをさらに20分間高速で撹拌した。
実施例1のポリマーを、硫酸含有溶媒と混合する。ポリマーが溶媒に十分に溶解し、繊維の紡糸に好適な溶液が形成されるまで、必要に応じて冷却して温度を制御しながら、混合物を撹拌する。
次に、本発明の態様を示す。
1. テレフタロイルクロライド、p−フェニレンジアミン、および式I:
(式中、A - は、ハロゲンアニオン、HSO 4 - 、OH - 、NO 3 - 、C 2 H 3 O 2 - 、またはH 2 PO 4 - である)の塩の残基を含むポリマーの製造方法であって、
a)有機溶媒と無機塩とを含む溶媒系中に式Iの塩とp−フェニレンジアミンとを含む混合物を形成する工程;
b)テレフタロイルクロライドを前記混合物に添加し、前記ポリマーを生成する工程;
を含む方法。
2. 化学量論量のテレフタロイルクロライドを前記混合物に添加する、上記1に記載の方法。
3. 前記有機溶媒が、N−メチル−2−ピロリドン(NMP)またはジメチルアセトアミド(DMAC)である、上記1または2に記載の方法。
4. 前記無機塩がLiClまたはCaCl 2 である、上記1〜3のいずれか一項に記載の方法。
5. 前記溶媒系がNMP/CaCl 2 である、上記1〜4のいずれか一項に記載の方法。
6. 前記式Iの塩が次式:
の塩である、上記1〜5のいずれか一項に記載の方法。
7. 前記テレフタロイルクロライドを2段階以上で添加する、上記2に記載の方法。
8. 工程b)が、
前記テレフタロイルクロライドの20〜50%を第1の添加段階で添加して、第2の混合物を形成すること、
前記第2の混合物を少なくとも1分間撹拌すること、および
前記撹拌された第2の混合物に前記残りのテレフタロイルクロライドを1つ以上の添加段階で添加すること、
を含む、上記7に記載の方法。
9. 工程b)が−10〜30℃の温度で行われる、上記1〜8のいずれか一項に記載の方法。
10. 前記式Iの塩とp−フェニレンジアミンが0.5〜4.0の範囲のモル比で存在する、上記1〜9のいずれか一項に記載の方法。
11. NMP/CaCl 2 のCaCl 2 重量パーセントが1.0〜10%の範囲である、上記5に記載の方法。
12. 前記ポリマーを単離する工程をさらに含む、上記1〜11のいずれか一項に記載の方法。
13. 前記ポリマーを粉砕する工程をさらに含む、上記12に記載の方法。
14. 前記ポリマーを1つ以上の洗浄工程、中和工程、またはその両方で処理することをさらに含む、上記12に記載の方法。
15. 前記粉砕されたポリマーを1つ以上の洗浄工程、中和工程、またはその両方で処理することをさらに含む、上記13に記載の方法。
16. 硫酸を含む溶媒に前記ポリマーを溶解し、繊維の紡糸に好適な溶液を形成する工程をさらに含む、上記14に記載の方法。
17. 硫酸を含む溶媒に前記ポリマーを溶解し、繊維の紡糸に好適な溶液を形成する工程をさらに含む、上記15に記載の方法。
18. N−メチル−2−ピロリドン(NMP)またはジメチルアセトアミド(DMAC)と無機塩とを含む溶媒に前記ポリマーを溶解し、繊維の紡糸に好適な溶液を形成する工程をさらに含む、上記14に記載の方法。
19. N−メチル−2−ピロリドン(NMP)またはジメチルアセトアミド(DMAC)と無機塩とを含む溶媒に前記ポリマーを溶解し、繊維の紡糸に好適な溶液を形成する工程をさらに含む、上記15に記載の方法。
Claims (1)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US201161513020P | 2011-07-29 | 2011-07-29 | |
US61/513,020 | 2011-07-29 | ||
PCT/US2012/048444 WO2013019579A1 (en) | 2011-07-29 | 2012-07-27 | Process for preparing aramid copolymer |
Publications (3)
Publication Number | Publication Date |
---|---|
JP2014521781A JP2014521781A (ja) | 2014-08-28 |
JP2014521781A5 JP2014521781A5 (ja) | 2015-09-10 |
JP6104908B2 true JP6104908B2 (ja) | 2017-03-29 |
Family
ID=46724606
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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JP2014523036A Active JP6104908B2 (ja) | 2011-07-29 | 2012-07-27 | アラミド共重合体の製造方法 |
Country Status (7)
Country | Link |
---|---|
US (1) | US8809434B2 (ja) |
EP (1) | EP2736956B1 (ja) |
JP (1) | JP6104908B2 (ja) |
KR (1) | KR101900128B1 (ja) |
CN (1) | CN103703055B (ja) |
BR (1) | BR112014000537A2 (ja) |
WO (1) | WO2013019579A1 (ja) |
Family Cites Families (28)
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JPS6031208B2 (ja) | 1974-07-10 | 1985-07-20 | 帝人株式会社 | ポリアミド溶液 |
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FR2502151A1 (fr) | 1981-03-20 | 1982-09-24 | Ugine Kuhlmann | Procede de preparation de l'(amino-4 phenyl)-2 amino-5 benzimidazole et de derives substitues |
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2012
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- 2012-07-27 BR BR112014000537A patent/BR112014000537A2/pt not_active IP Right Cessation
- 2012-07-27 EP EP12750637.6A patent/EP2736956B1/en active Active
- 2012-07-27 WO PCT/US2012/048444 patent/WO2013019579A1/en unknown
- 2012-07-27 CN CN201280036109.XA patent/CN103703055B/zh active Active
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WO2013019579A1 (en) | 2013-02-07 |
EP2736956A1 (en) | 2014-06-04 |
CN103703055B (zh) | 2015-12-09 |
KR20140051981A (ko) | 2014-05-02 |
JP2014521781A (ja) | 2014-08-28 |
EP2736956B1 (en) | 2018-10-24 |
BR112014000537A2 (pt) | 2017-02-14 |
US8809434B2 (en) | 2014-08-19 |
KR101900128B1 (ko) | 2018-09-18 |
US20130203906A1 (en) | 2013-08-08 |
CN103703055A (zh) | 2014-04-02 |
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