JP2011184478A - Aromatic polyamide solution and resin composition composed of the same - Google Patents
Aromatic polyamide solution and resin composition composed of the same Download PDFInfo
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- JP2011184478A JP2011184478A JP2010047770A JP2010047770A JP2011184478A JP 2011184478 A JP2011184478 A JP 2011184478A JP 2010047770 A JP2010047770 A JP 2010047770A JP 2010047770 A JP2010047770 A JP 2010047770A JP 2011184478 A JP2011184478 A JP 2011184478A
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- 239000004760 aramid Substances 0.000 title claims abstract description 34
- 229920003235 aromatic polyamide Polymers 0.000 title claims abstract description 34
- 239000011342 resin composition Substances 0.000 title claims abstract description 7
- 239000002904 solvent Substances 0.000 claims abstract description 9
- 239000000835 fiber Substances 0.000 claims description 9
- -1 polyparaphenylene terephthalamide Polymers 0.000 claims description 7
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 4
- 239000000843 powder Substances 0.000 claims description 4
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical compound NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 150000004984 aromatic diamines Chemical class 0.000 claims description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- 239000000243 solution Substances 0.000 description 19
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 10
- 238000009987 spinning Methods 0.000 description 10
- 230000015271 coagulation Effects 0.000 description 7
- 238000005345 coagulation Methods 0.000 description 7
- 238000000034 method Methods 0.000 description 6
- 229920000642 polymer Polymers 0.000 description 4
- 239000011550 stock solution Substances 0.000 description 4
- LBVMWHCOFMFPEG-UHFFFAOYSA-N 3-methoxy-n,n-dimethylpropanamide Chemical compound COCCC(=O)N(C)C LBVMWHCOFMFPEG-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 230000001112 coagulating effect Effects 0.000 description 3
- 238000001523 electrospinning Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 229920001410 Microfiber Polymers 0.000 description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
- 230000005684 electric field Effects 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 229910017053 inorganic salt Inorganic materials 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000002798 polar solvent Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 238000010008 shearing Methods 0.000 description 2
- CYSGHNMQYZDMIA-UHFFFAOYSA-N 1,3-Dimethyl-2-imidazolidinon Chemical compound CN1CCN(C)C1=O CYSGHNMQYZDMIA-UHFFFAOYSA-N 0.000 description 1
- MLAKIIPISRSRGQ-UHFFFAOYSA-N 3-methoxy-1-morpholin-4-ylpropan-1-one Chemical compound COCCC(=O)N1CCOCC1 MLAKIIPISRSRGQ-UHFFFAOYSA-N 0.000 description 1
- SIXSDXBPHBHLPS-UHFFFAOYSA-N 3-methoxy-n-methylpropanamide Chemical compound CNC(=O)CCOC SIXSDXBPHBHLPS-UHFFFAOYSA-N 0.000 description 1
- HCVNNCXJZAWCEM-UHFFFAOYSA-N COC(CC(=O)N1CCCCC1)OC Chemical compound COC(CC(=O)N1CCCCC1)OC HCVNNCXJZAWCEM-UHFFFAOYSA-N 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 238000010009 beating Methods 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000006258 conductive agent Substances 0.000 description 1
- 238000007599 discharging Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 238000009998 heat setting Methods 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000006224 matting agent Substances 0.000 description 1
- 238000000691 measurement method Methods 0.000 description 1
- XTIGOJREHGWIKM-UHFFFAOYSA-N n,n-dibutyl-3-methoxypropanamide Chemical compound CCCCN(CCCC)C(=O)CCOC XTIGOJREHGWIKM-UHFFFAOYSA-N 0.000 description 1
- KRAUBBLJGPEJCB-UHFFFAOYSA-N n-butyl-3-methoxypropanamide Chemical compound CCCCNC(=O)CCOC KRAUBBLJGPEJCB-UHFFFAOYSA-N 0.000 description 1
- OYGDQLOTAHZZHD-UHFFFAOYSA-N n-ethyl-3-methoxypropanamide Chemical compound CCNC(=O)CCOC OYGDQLOTAHZZHD-UHFFFAOYSA-N 0.000 description 1
- 239000013557 residual solvent Substances 0.000 description 1
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- Compositions Of Macromolecular Compounds (AREA)
- Artificial Filaments (AREA)
Abstract
Description
本発明は、品質及び安全性に優れた芳香族ポリアミド繊維、フィルム、テープ、フィブリッド、パウダーなどを製造するための芳香族ポリアミド溶液を提供するためのものである。 The present invention is to provide an aromatic polyamide solution for producing aromatic polyamide fibers, films, tapes, fibrids, powders and the like excellent in quality and safety.
芳香族ポリアミド繊維等を製造する方法としては、芳香族ポリアミドを溶媒に溶解した紡糸原液を無機塩水溶液の凝固液中に押し出し、凝固させた糸条を引き出した後に水洗、延伸、熱処理する方法（特公昭４８−１７５５１号公報）、あるいは、エレクトロスピニング（電界紡糸）法により、該紡糸原液を、ノズルから押し出すとともに、押し出した紡糸溶液に電界を作用させて、極細繊維化する方法（特開２００７−１７０２２４号公報）、さらには、該紡糸原液を水系凝固液中に導入した後、攪拌等のせん断力下、凝固させることによって得られた芳香族ポリアミドの含水生成物を叩解処理してフィブリル繊維を得る方法（特開２００８−２５５５５０号公報）などが例示されている。 As a method for producing an aromatic polyamide fiber or the like, a spinning undiluted solution in which an aromatic polyamide is dissolved in a solvent is extruded into a coagulating liquid of an inorganic salt aqueous solution, and the coagulated yarn is drawn out, followed by washing, stretching, and heat treatment ( (Japanese Patent Publication No. 48-17551) or electrospinning (electrospinning) method, and the spinning solution is extruded from a nozzle and an electric field is applied to the extruded spinning solution to form ultrafine fibers (JP 2007-2007). -170224), and further, after introducing the spinning solution into an aqueous coagulation solution, the hydrated product of the aromatic polyamide obtained by coagulation under a shearing force such as stirring is beaten to produce fibril fibers. The method (Japanese Unexamined Patent Application Publication No. 2008-255550) and the like are exemplified.
上記の方法はいずれも芳香族ポリアミドをＮ，Ｎ−ジメチルホルムアミド、Ｎ，Ｎ−ジメチルアセトアミド、Ｎ−メチル−２−ピロリドン、ジメチルイミダゾリジノンなどのアミド系極性溶媒に溶解・分散させることが一般的である。これらアミド系極性溶媒は、芳香族ポリアミドの良溶媒であると同時に、凝固浴として一般的に用いられる金属塩水溶液にも任意の割合にて混合・溶解するため、紡糸原液調整用の溶媒として好ましく用いられる。なかでもＮ−メチル−２−ピロリドン（ＮＭＰ）、Ｎ，Ｎ−ジメチルアセトアミドが芳香族ポリアミドの溶解性が良好で好ましく用いられている。また、近年の報告により、一部のアミド溶媒について、ウサギの皮膚を用いた試験結果より皮膚に対する刺激性があることが明らかとなってきた。このため、より安全で洗浄効率の高い紡糸溶液系を構築することには、非常に高い関心、要望があった。 In any of the above methods, an aromatic polyamide is generally dissolved and dispersed in an amide polar solvent such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methyl-2-pyrrolidone, dimethylimidazolidinone. Is. These amide polar solvents are good solvents for aromatic polyamides, and at the same time, are also mixed and dissolved in an aqueous solution of metal salt generally used as a coagulation bath at an arbitrary ratio. Used. Of these, N-methyl-2-pyrrolidone (NMP) and N, N-dimethylacetamide are preferably used because of their good solubility in aromatic polyamides. In addition, recent reports have revealed that some amide solvents are irritating to the skin from the results of tests using rabbit skin. For this reason, there has been a very high interest and demand in constructing a spinning solution system that is safer and has higher cleaning efficiency.
我々発明者は、上記のような背景を受けて、芳香族ポリアミドを容易に溶解し、さらには安全に取り扱うことの出来る溶媒を発見することに着手した。 In light of the above-mentioned background, the present inventors set out to find a solvent that can easily dissolve an aromatic polyamide and that can be handled safely.
本発明者らは、芳香族ポリアミドを容易に溶解し、さらには安全に取り扱うことの出来る溶液として以下を提案する。すなわち、芳香族ポリアミドと化学式（１）で示されるβ−アルコキシプロピオンアミド系溶剤を含む芳香族ポリアミドの溶液である。 The present inventors propose the following as a solution which can dissolve aromatic polyamide easily and can be handled safely. That is, it is a solution of an aromatic polyamide containing an aromatic polyamide and a β-alkoxypropionamide solvent represented by the chemical formula (1).
本発明によれば、芳香族ポリアミドを容易に溶解し、さらには安全に取り扱うことの出来る溶液を提供することができる。 ADVANTAGE OF THE INVENTION According to this invention, the solution which can melt | dissolve aromatic polyamide easily and can also handle safely can be provided.
以下、本発明について詳細に説明する。
本発明における芳香族ポリアミドとは、芳香族ジカルボン酸成分と芳香族ジアミン成分、もしくは芳香族アミノカルボン酸成分から構成される芳香族ポリアミド、又はこれらの芳香族共重合ポリアミドからなるポリマーであり、例えばポリパラフェニレンテレフタルアミド、コポリパラフェニレン・３，４’−オキシジフェニレンテレフタルアミド、ポリメタフェニレンイソフタルアミドなどが例示できるがこれらに限定されるものではない。
Hereinafter, the present invention will be described in detail.
The aromatic polyamide in the present invention is an aromatic polyamide composed of an aromatic dicarboxylic acid component and an aromatic diamine component, or an aromatic aminocarboxylic acid component, or a polymer composed of these aromatic copolyamides. Examples thereof include, but are not limited to, polyparaphenylene terephthalamide, copolyparaphenylene 3,4'-oxydiphenylene terephthalamide, and polymetaphenylene isophthalamide.
本発明におけるβ―アルコキシプロピオンアミド類としては、以下のものが好適に例示される。すなわち、β―メトキシプロピオンアミド、β―メトキシ−Ｎ―メチルプロピオンアミド、β−メトキシ−Ｎ，Ｎ−ジメチルプロピオンアミド、β−メトキシ−Ｎ−エチルプロピオンアミド、β―メトキシ−Ｎ，Ｎ−ジエチルプロピオンアミド、β―メトキシ−（Ｎ−プロピル）プロピオンアミド、β−メトキシ−（Ｎ，Ｎ−ジプロピル）プロピオンアミド、β−メトキシ−Ｎ−ブチルプロピオンアミド、βメトキシ−Ｎ，Ｎ−ジブチルプロピオンアミド、１−（β−メトキシプロピオニル）ピロリジン、β−メトキシ−１−（β―メトキシプロピオニル）ピペリジン、４−（β−メトキシプロピオニル）モルホリンなどが挙げられる。 Preferred examples of β-alkoxypropionamides in the present invention include the following. Β-methoxypropionamide, β-methoxy-N-methylpropionamide, β-methoxy-N, N-dimethylpropionamide, β-methoxy-N-ethylpropionamide, β-methoxy-N, N-diethylpropionamide Amide, β-methoxy- (N-propyl) propionamide, β-methoxy- (N, N-dipropyl) propionamide, β-methoxy-N-butylpropionamide, βmethoxy-N, N-dibutylpropionamide, 1 -(Β-methoxypropionyl) pyrrolidine, β-methoxy-1- (β-methoxypropionyl) piperidine, 4- (β-methoxypropionyl) morpholine and the like.
本発明の芳香族ポリアミド溶液には、必要に応じて溶液の安定性を向上させるために各種金属塩、または／および性能向上のための難燃剤、着色剤、艶消剤、耐光剤、導電剤などの添加剤が含有されていても良い。 The aromatic polyamide solution of the present invention includes various metal salts for improving the stability of the solution, if necessary, and / or flame retardants, colorants, matting agents, light proofing agents, conductive agents for improving performance. Such additives may be contained.
本発明における樹脂組成物とは、繊維、フィルム、テープ、フィブリッド、またはパウダーを指す。芳香族ポリアミド繊維を製造する方法としては、前述のように芳香族ポリアミドを溶媒に溶解した紡糸原液を無機塩水溶液の凝固液中に押し出し、凝固させた糸条を引き出した後に水洗、延伸、熱処理する方法、あるいは、エレクトロスピニング法により、該紡糸原液に電界を作用させて、極細繊維化する方法、さらには、該紡糸原液を水系凝固液中に導入した後、攪拌等のせん断下、凝固させることによって得られた芳香族ポリアミドの含水生成物を叩解処理してフィブリル繊維を得る方法など、特に限定されることなく使用できる。 The resin composition in the present invention refers to fiber, film, tape, fibrid, or powder. As a method for producing an aromatic polyamide fiber, as described above, a spinning stock solution in which an aromatic polyamide is dissolved in a solvent is extruded into a coagulating solution of an inorganic salt aqueous solution, and the coagulated yarn is drawn out, followed by washing, drawing, and heat treatment. Or a method of applying an electric field to the spinning stock solution to form ultrafine fibers by electrospinning, and further, the spinning stock solution is introduced into an aqueous coagulating solution and then solidified under shearing such as stirring. A method for obtaining a fibril fiber by beating a hydrous product of an aromatic polyamide obtained in this way is not particularly limited.
以下、実施例により、本発明を更に具体的に説明する。なお、本発明はこれらの実施例に限られるものではない。実施例における各項目は次の方法で測定した。
（１）＜固有粘度（ＩＶ）＞
ポリマー０．５ｇをＮＭＰ１００ｍｌに溶解し、オストワルド粘度計を用い３０℃で測定した。
（２）＜繊度＞
ＪＩＳ−Ｌ−１０１５に準拠し測定した。
（３）＜強度、伸度＞
ＪＩＳ−Ｌ−１０１５に準拠し、試料長２０ｍｍ、初荷重０．４４ｍＮ／ｄＴｅｘ、伸張速度２０ｍｍ／分にて測定した。
（４）＜難燃性＞
ＪＩＳ−Ｋ−７２０１のＬＯＩ測定法に準拠して、ＬＯＩ値を求めた。
Hereinafter, the present invention will be described more specifically with reference to examples. The present invention is not limited to these examples. Each item in the examples was measured by the following method.
(1) <Intrinsic viscosity (IV)>
0.5 g of polymer was dissolved in 100 ml of NMP, and measured at 30 ° C. using an Ostwald viscometer.
(2) <Fineness>
It measured based on JIS-L-1015.
(3) <Strength and elongation>
Based on JIS-L-1015, the sample length was 20 mm, the initial load was 0.44 mN / dTex, and the extension rate was 20 mm / min.
(4) <Flame retardance>
The LOI value was determined based on the JIS-K-7201 LOI measurement method.
［実施例１］
ＩＶ＝１．９のポリメタフェニレンイソフタルアミド１８重量％をβ−メトキシ−Ｎ，Ｎ−ジメチルプロピオンアミド８２重量％に混合し−５℃に冷却した溶液とした後、攪拌しながら６０℃まで加温、溶解させ紡糸溶液（ポリマー濃度１８重量％）を得た。
このポリマー溶液を８５℃に加温して紡糸原液とし、孔径０．０７ｍｍ、孔数１５００の紡糸口金から８５℃の凝固浴中に吐出して紡糸した。この凝固浴の組成は、塩化カルシウムを４０重量％、β−メトキシ−Ｎ，Ｎ−ジメチルプロピオンアミドを５重量％含み、残り５５重量％が水である。紡糸糸条をこの凝固浴中に浸漬長（有効凝固浴長）３０ｃｍにて糸速７．０ｍ／分で通過させた後、いったん空気中に引き出した。この凝固糸条を水温２５℃、４５℃、７０℃の三段階の水洗浴を通して繊維中の残存溶媒を除去した。
水洗後の糸条を引続き９８℃の温水中で段階的に４．４５倍に延伸し、更に７０℃の乾燥ローラを通して乾燥した後、２００℃の熱ローラで予熱し、次いで３４０℃のローラで熱セットし目的のポリメタフェニレンイソフタルアミド繊維を得た。
[Example 1]
After mixing 18% by weight of polymetaphenylene isophthalamide of IV = 1.9 with 82% by weight of β-methoxy-N, N-dimethylpropionamide to form a solution cooled to −5 ° C., the mixture was added to 60 ° C. with stirring. The solution was heated and dissolved to obtain a spinning solution (polymer concentration: 18% by weight).
This polymer solution was heated to 85 ° C. to give a spinning stock solution, and spun by discharging it from a spinneret having a hole diameter of 0.07 mm and a hole number of 1500 into a coagulation bath at 85 ° C. The composition of the coagulation bath is 40% by weight of calcium chloride, 5% by weight of β-methoxy-N, N-dimethylpropionamide, and the remaining 55% by weight is water. The spun yarn was passed through the coagulation bath at an immersion length (effective coagulation bath length) of 30 cm at a yarn speed of 7.0 m / min, and then pulled out into the air. The coagulated yarn was passed through a three-stage water-washing bath with water temperatures of 25 ° C., 45 ° C., and 70 ° C. to remove the residual solvent in the fiber.
The washed yarn is continuously stretched to 4.45 times in 98 ° C warm water, further dried through a 70 ° C drying roller, preheated with a 200 ° C hot roller, and then with a 340 ° C roller. The target polymetaphenylene isophthalamide fiber was obtained by heat setting.
［比較例１］
溶剤にＮＭＰを用いた以外は実施例と同様の処理を行い、延伸トウを得た。
結果を表１に示す。
[Comparative Example 1]
Except for using NMP as a solvent, the same treatment as in Example was performed to obtain a stretched tow.
The results are shown in Table 1.
本発明によれば、芳香族ポリアミドを容易に溶解し、さらには安全に取り扱うことの出来る溶液を提供することができ、樹脂組成物、例えば、フィルム、テープ、フィブリッド、またはパウダーなどが好適に製造できる。 ADVANTAGE OF THE INVENTION According to this invention, the solution which can melt | dissolve aromatic polyamide easily, and also can be handled safely can be provided, and a resin composition, for example, a film, a tape, a fibrid, or a powder is manufactured suitably. it can.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
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| JP2018146795A (en) * | 2017-03-06 | 2018-09-20 | 富士ゼロックス株式会社 | Transfer belt, transfer belt unit, image forming apparatus, and method for manufacturing transfer belt |
| CN118373983A (en) * | 2024-06-24 | 2024-07-23 | 烟台泰和新材高分子新材料研究院有限公司 | High-solid-content meta-aramid polymerization stock solution, meta-aramid fiber and preparation method |
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2010
- 2010-03-04 JP JP2010047770A patent/JP2011184478A/en active Pending
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2018146795A (en) * | 2017-03-06 | 2018-09-20 | 富士ゼロックス株式会社 | Transfer belt, transfer belt unit, image forming apparatus, and method for manufacturing transfer belt |
| CN118373983A (en) * | 2024-06-24 | 2024-07-23 | 烟台泰和新材高分子新材料研究院有限公司 | High-solid-content meta-aramid polymerization stock solution, meta-aramid fiber and preparation method |
| CN118373983B (en) * | 2024-06-24 | 2024-09-17 | 烟台泰和新材高分子新材料研究院有限公司 | High-solid-content meta-aramid polymerization stock solution, meta-aramid fiber and preparation method |
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