No. 39 Facile Method for Inclusion Capacity Determination of Finished Textiles using Monochlorotriazinyl Cyclodextrin

Presentations with regard to MCT-β-CD at the Society of Cyclodextrins

• THE SYNTHESIS AND USES OF CYCLODEXTRIN DERIVATIVES HAVING SILANE FUNCTIONAL GROUPS
  Keiji Terao, Shouhei Tani, Munetaka Kunishima, Jun Morita, Masaki Ishikawa, Hitoshi Hashimoto (1998)
• THE SYNTHESIS AND USES OF NEW FUNCTINAL TEXTILE BY THE USE OF MONOCHLOROTRLAZINYL-BETA-CYCLODEXTRIN
  Keiji Terao, Yoshiko Kubo, Munetaka Kunishima, Shouhei Tani, Katsuhiko Mikuni, Hitoshi Hashimoto (1999)
• Antibacterial activities of iodine-chemically modified cyclodextrin complexes
  Keiji TERAO, Daisuke NAKATA, Iwao TACHI, Katsuo TACHI, Munetaka KUNISHIMA, Shohei TANI (2002)
• PREPARATION OF WATER SOLUBLE CYCLODEXTRIN POLYMERS AND THEIR UTILIZATION
  Minako KUWAHARA, Jun MORITA, Keiji TERAO, Daisuke NAKATA, Munetaka KUNISHIMA, Shohei TANI (2005)
• Studies on the Industrial Production of Monochlorotriazinyl-β-cyclodextrin and its Fixation to Textile Fibers
  Yoshimi ASADA, Akira YAMANOBE, Daisuke NAKATA, Iwao TACHI, Keiji TERAO (2010)

Introduction

Now, substitution degree (DS) of Monochlorotriazino group (MCT group) in commercially available MCT-β-CD is 0.4 per glucose. So MCT-β-CD has 2.8 MCT group in one β-CD molecule.

Since the removal cost of sodium chloride, the by-product of synthetic process, is very high, the price of MCT-β-CD becomes very high. For this reason, its industrial application had been limited. Therefore, we reported the fixation method of using MCT-β-CD to the textile without NaCl salt removal in the last symposium.

We have already developed some determination methods for the inclusion capacity on finished textile using MCT-β-CD. However those procedures need so complicated analytical instruments for usual textile manufacturers.

In this study, we investigated a facile and convenient method for inclusion capacity determination of β-CD cavity on finished textile by the use of phenolphthalein.

In addition we report three studies, the immobilization of MCT-β-CD to the polyester fiber, its ammonia absorption, and sustained release of menthol encapusulated in β-CD cavity.

MCT-β-CD fixation temperature on polyester

When the fixation temperature was above 130℃, the weight could increase. It is supposed that MCT-β-CD polymerizes by heat, and the polymer is entwined around the polyester fiber.

Mechanism of MCT-β-CD fixing to polyester fiber

Image of MCT-β-CD fixed to polyester fiber

MCT-β-CD polymerization mechanism

Facile determination method for inclusion capacity of MCT-β-CD fixed on fiber by using phenolphthalein

Determination method for inclusion capacity of MCT-β-CD fixed on fiber

Evaluation example of MCT-β-CD fixed fiber

When MCT-β-CD fixed cotton fiber was dipped into phenolphthalein aqueous solution and picked up the solution, the fiber was colored. But after drying by heat, the color was disappeared. It seems that phenolphthalein was encapsulated in CD cavity.

Evaluation Procedure of Ammonia absorption by MCT-β-CD finished cotton

Evaluation procedure - ①

Evaluation procedure - ②

Effect of ammonia absorption by MCT-β-CD fixed cotton

Absorption ratio of ammonia increased with an increase of the washing frequency.
As for washing with the NaClO solution, absorption effect of ammonia is larger than that of tap water. It is thought the chlorine contained in tap water influences the effect.

Sustained release evaluation using solid phase microextraction method

Sustained release examination of menthol / MCT-β-CD fixed fiber by solid phase microextraction method

When menthol/MCT-β-CD fixed fiber was left under high humidity and temperature, the sustained release of menthol was seen during 24 hours.
And, it was confirmed that cooling sensation was maintained even after 24 hours.

Change in skin surface temperature of body before and after exercise putting on underwear of menthol encapsulated MCT-β-CD fixed fiber

At moving for 15 minutes while putting on the underwear of menthol/MCT-β-CD fixed fiber under room temperature, the rise of skin surface temperature was suppressed.
It was confirmed that the substance suppresses skin surface temperature rise effectively.

Cooling effect on skin before and after exercise putting on underwear of menthol encapsulated MCT-β-CD fixed fiber

At the moving while putting on the underwear of menthol encapsulated MCT-β-CD fixed fiber under the constant temperature, the skin surface temperature after 11 minutes of the start is lowered. And, it was confirmed that substance suppresses body temperature rise effectively.

Functional Ingredients having various effects can be encapsulated by MCT-β-CD fixed fiber

Conclusions

• When MCT-β-CD fixed cotton fiber was dipped into phenolphthalein aqueous solution and picked up the solution, the fiber was colored. But after drying by heat, the color was disappeared. It seems that phenolphthalein was encapsulated in CD cavity.
• The fixation of MCT-β-CD on the polyester fiber without the reactive group could be acieved like finished cotton fiber with increasing weight. It is supposed that MCT-β-CD could polymerize by heat, and the polymer is entwined around the polyester fiber.
• It is confirmed that ammonia is absorbed by MCT-β-CD fixed cotton. The result was significant after washing. It is thought the chlorine containing in tap water influences the effect.
• It was confirmed that cooling sensation was maintained for a long time when putting on the underwear of menthol encapsulated MCT-β-CD fixed cotton fiber.