JP2009161693A5 - - Google Patents
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- Publication number
- JP2009161693A5 JP2009161693A5 JP2008002397A JP2008002397A JP2009161693A5 JP 2009161693 A5 JP2009161693 A5 JP 2009161693A5 JP 2008002397 A JP2008002397 A JP 2008002397A JP 2008002397 A JP2008002397 A JP 2008002397A JP 2009161693 A5 JP2009161693 A5 JP 2009161693A5
- Authority
- JP
- Japan
- Prior art keywords
- sulfoisophthalic acid
- dyeing
- tetrabutyl phosphonium
- weight
- cationic dyeable
- 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.)
- Granted
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- 125000002091 cationic group Chemical group 0.000 claims description 7
- 229920000728 polyester Polymers 0.000 claims description 5
- XGYQCXAJJSNIJB-UHFFFAOYSA-N 5-sulfobenzene-1,3-dicarboxylic acid;tetrabutylphosphanium Chemical compound OC(=O)C1=CC(C(O)=O)=CC(S(O)(=O)=O)=C1.CCCC[P+](CCCC)(CCCC)CCCC XGYQCXAJJSNIJB-UHFFFAOYSA-N 0.000 claims description 4
- -1 5-sulfoisophthalic acid dimethyl tetrabutyl phosphonium Chemical compound 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 claims 1
- 238000004043 dyeing Methods 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 239000000975 dye Substances 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 238000006068 polycondensation reaction Methods 0.000 description 3
- ADCOVFLJGNWWNZ-UHFFFAOYSA-N Antimony trioxide Chemical compound O=[Sb]O[Sb]=O ADCOVFLJGNWWNZ-UHFFFAOYSA-N 0.000 description 2
- 238000002835 absorbance Methods 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- ZMANZCXQSJIPKH-UHFFFAOYSA-N triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 2
- HMIFKTNTRBGMAK-UHFFFAOYSA-N 2-sulfobenzene-1,3-dicarboxylic acid;tetrabutylphosphanium Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1S(O)(=O)=O.CCCC[P+](CCCC)(CCCC)CCCC HMIFKTNTRBGMAK-UHFFFAOYSA-N 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H Tricalcium phosphate Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000002074 melt spinning Methods 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L na2so4 Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 229940073455 tetraethylammonium hydroxide Drugs 0.000 description 1
- LRGJRHZIDJQFCL-UHFFFAOYSA-M tetraethylazanium;hydroxide Chemical compound [OH-].CC[N+](CC)(CC)CC LRGJRHZIDJQFCL-UHFFFAOYSA-M 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 235000019731 tricalcium phosphate Nutrition 0.000 description 1
Description
一方、このような問題を解決するため、イオン結合性分子間力の小さいカチオン可染性モノマーを共重合する技術が開示されている（例えば、特許文献３、特許文献４参照。）。イオン結合性分子間力の小さいカチオン可染性モノマーとしては、５−スルホイソフタル酸テトラブチルホスホニウムなどが例示されているが、これらのカチオン可染性モノマー共重合ポリエステルは熱安定性が悪く、常圧カチオン可染化させるため、共重合量を増加させようとしても、重合反応途中で熱分解が進行し、高分子量化させることが困難であった。さらに溶融紡糸する際の熱履歴による分解が大きく、結果として得られる糸の強度が弱くなるという欠点を有していた。また、使用する５−スルホイソフタル酸テトラブチルホスホニウムは非常に高価であり、結果として得られるカチオン可染性ポリエステルのコストが大幅に増大するという問題があった。 On the other hand, in order to solve such a problem, a technique of copolymerizing a cationic dyeable monomer having a small ion-binding intermolecular force has been disclosed (for example, see Patent Document 3 and Patent Document 4). The small cationic dyeable monomers having ion binding intermolecular force, 5 although such sulfoisophthalic acid tetrabutyl phosphonium are illustrated, these cationic dyeable monomers copolymerized polyester thermal stability is poor, normal pressure Even if an attempt is made to increase the amount of copolymerization for cationic dyeing, thermal decomposition progressed during the polymerization reaction, making it difficult to increase the molecular weight. Furthermore, there is a drawback that the decomposition due to the thermal history during melt spinning is large, and the strength of the resulting yarn is weakened. Furthermore, 5-sulfoisophthalic acid tetrabutyl phosphonium used is very expensive, the cost of the cationic dyeable polyester obtained as a result there is a problem that greatly increased.
（ウ）カチオン可染性：
ＣＡＴＨＩＬＯＮ ＢＬＵＥ ＣＤ−ＦＲＬＨ０．２ｇ／Ｌ、ＣＤ−ＦＢＬＨ０．２ｇ／Ｌ（いずれも保土ヶ谷化学株式会社製のカチオン可染性染料）、硫酸ナトリウム３ｇ／Ｌ、酢酸０．３ｇ／Ｌの染色液中にて１２５℃で１時間、浴比１：５０で染色し、次式により染着率を求めた。
染着率＝（ＯＤ０−ＯＤ１）／ＯＤ０ ×１００（％）
ＯＤ０：染色前の染液の５７６ｎｍの吸光度
ＯＤ１：染色後の染液の５７６ｎｍの吸光度
本発明の実施例では、染着率９８％以上のものを可染性良好と判断した。
(C) Cation dyeability:
CATHILON BLUE CD-FRL H0. 1 hour at 125 ° C. in a dyeing solution of 2 g / L, CD-FBLH 0.2 g / L (both cationic dyeable dyes manufactured by Hodogaya Chemical Co., Ltd.), sodium sulfate 3 g / L, acetic acid 0.3 g / L Dyeing was performed at a bath ratio of 1:50, and the dyeing rate was determined by the following formula.
Dyeing rate = (OD 0 −OD 1 ) / OD 0 × 100 (%)
OD 0 : Absorbance at 576 nm of the dye solution before dyeing OD 1 : Absorbance at 576 nm of the dye solution after dyeing In the examples of the present invention, those having a dyeing rate of 98% or more were judged to have good dyeability.
その後、反応生成物に三酸化アンチモン０．０５重量部と５−スルホイソフタル酸テトラブチルホスホニウム２．８重量部と水酸化テトラエチルアンモニウム０．３重量部とトリエチルアミン０．００３重量部、及び不活性粒子として平均粒子径０．０６μｍの第三リン酸カルシウムの２０重量％エチレングリコールスラリー２．６重量部を添加した後、重縮合槽に移し、２８５℃まで昇温し、３０Ｐａ以下の高真空にて重縮合反応を行い、重縮合槽の攪拌機電力の値が所定電力に到達した段階若しくは所定時間を経過した段階で反応を終了させ、常法に従いチップ化した。 Then, antimony trioxide 0.05 parts by weight 5-sulfoisophthalic acid tetrabutyl phosphonium 2.8 parts by weight to 0.3 part by weight of tetraethylammonium hydroxide and triethylamine 0.003 parts by weight to the reaction product, and as the inert particles After adding 2.6 parts by weight of 20 wt% ethylene glycol slurry of tribasic calcium phosphate having an average particle size of 0.06 μm, it is transferred to a polycondensation tank, heated to 285 ° C., and subjected to a polycondensation reaction at a high vacuum of 30 Pa or less. The reaction was terminated when the value of the agitator power in the polycondensation tank reached a predetermined power or when a predetermined time had elapsed, and the chip was formed according to a conventional method.
［実施例２〜４、比較例１〜８］
実施例１において、５−スルホイソフタル酸ナトリウム及び５−スルホイソフタル酸テトラブチルホスホニウムの添加量を表１となるように変更したこと以外は実施例１と同様に実施した。ポリエステル組成物の製造条件と評価結果の詳細を表１に示した。
[Examples 2 to 4, Comparative Examples 1 to 8]
In Example 1, except that the amount of 5-sodium sulfoisophthalic acid and 5-sulfoisophthalic acid tetrabutyl phosphonium were changed so that the Table 1 was conducted in the same manner as in Example 1. Details of the production conditions and evaluation results of the polyester composition are shown in Table 1.
［比較例１０］
実施例１において、不活性粒子を添加しないこと以外は実施例１と同様に実施した。ポリエステル組成物の製造条件と評価結果の詳細を表１に示した。
[Comparative Example 10]
In Example 1, it implemented like Example 1 except not adding an inert particle. Details of the production conditions and evaluation results of the polyester composition are shown in Table 1.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2008002397A JP5218887B2 (en) | 2008-01-09 | 2008-01-09 | Normal pressure cationic dyeable polyester composition and polyester fiber comprising the same |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2008002397A JP5218887B2 (en) | 2008-01-09 | 2008-01-09 | Normal pressure cationic dyeable polyester composition and polyester fiber comprising the same |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2009161693A JP2009161693A (en) | 2009-07-23 |
| JP2009161693A5 true JP2009161693A5 (en) | 2010-11-25 |
| JP5218887B2 JP5218887B2 (en) | 2013-06-26 |
Family
ID=40964671
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2008002397A Expired - Fee Related JP5218887B2 (en) | 2008-01-09 | 2008-01-09 | Normal pressure cationic dyeable polyester composition and polyester fiber comprising the same |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP5218887B2 (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MX2010007284A (en) * | 2008-01-08 | 2010-08-11 | Teijin Fibers Ltd | Normal pressure cation dyeable polyester and fiber. |
| JP2009161694A (en) * | 2008-01-09 | 2009-07-23 | Teijin Fibers Ltd | Ordinary-pressure cation-dyeable polyester |
| PT2492390T (en) | 2009-10-20 | 2018-06-19 | Teijin Frontier Co Ltd | Polyester fibers, process for production of the polyester fibers, cloth, and fiber product |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0819627B2 (en) * | 1989-07-07 | 1996-02-28 | 帝人株式会社 | Dyeing method for polyester fiber |
| JPH09151306A (en) * | 1995-11-30 | 1997-06-10 | Teijin Ltd | Polyester composition and its production |
| JP3745872B2 (en) * | 1997-03-05 | 2006-02-15 | 帝人ファイバー株式会社 | Antifouling copolyester and polyester fiber comprising the same |
| JP3742213B2 (en) * | 1998-02-18 | 2006-02-01 | 株式会社クラレ | Leather-like sheet |
| JP2007284599A (en) * | 2006-04-18 | 2007-11-01 | Teijin Fibers Ltd | Copolymer polyester composition and fiber |
-
2008
- 2008-01-09 JP JP2008002397A patent/JP5218887B2/en not_active Expired - Fee Related
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