64
cyclodextrins that enabled the improvement of different chromatographic
separations.
The first comprehensive review on potential applications in cosmetology, toiletry, and hygiene has been published by Szejtli (1982b). This topic was later
updated by Vaution et al. (1987), Hashimoto (1996, 2006), Citernesi and Sciacchitano
(1995), Buschmann and Schollmeyer (2002), and Duchêne et al. (2009). In the
mid- 1980s, some products appear in the market although the cyclodextrins were
often used without any indication of their precise role: Epicutin
®
TT, Chemishes
Laboratorium Dr Kurt Richter, a complex between cyclodextrin and Melaleuca
alternifolia leaf oil, used in skin care applications; Vivace
®
, Shiseifo Co., a powder
cologne; Klorane
®
, Klorane Laboratories, a dry shampoo; Novoflex
®
, Revlon, a
vitamin shampoo; Eucerin
®
Vital Active, Beiersdorf, a vitamin A cream; etc. In the
cosmetic industry, cyclodextrin complexes were useful for modifying solubility,
improving stabilization, transforming liquids into solids, preserving color, decreasing an unpleasant smell, or diminishing the odor of mercaptan used in permanent
hair preparations. Cyclodextrins were used as empty capsules in dry shampoos to
eliminate fatty substances such as sebum, or in toothpaste and mouthwash to remove
undesirable odors (Duchêne et al. 2009).
In the 1980s, applications were found in textiles including textile finishing and
functional textiles (Szejtli 1985; Hashimoto 1996; Buschmann and Schollmeyer
2002). The permanent fixation of cyclodextrin molecules offered textiles with interesting properties, e.g., the formation of body odor was reduced by the complexation, the release of perfumes from cyclodextrins was possible, etc. The first
cellulose- cyclodextrin copolymer was described in 1980 by Szejtli’s group. Alkaliswollen cellulose fibers were reacted with epichlorohydrin. The chemically bound
cyclodextrin retained its complex-forming ability and could be loaded with chemically and/or biologically active guests such as perfumes to prepare perfumed textiles or drugs to prepare medical bandages (Szejtli et al. 1980b). For instance,
Fig. 1.27 illustrates a guest exchange by a cellulose fiber containing cyclodextrin.
The process consists to load the fixed cyclodextrin molecules with perfume molecules. During wearing and by sweat humidity, excreted short-chain fatty acids displace and release the perfume molecules and will be in turn entrapped (Szejtli
2003). Procter & Gamble recognized that similar effects can be achieved without
chemical fixation by simple spraying of hydroxypropyl-β-cyclodextrin solution on
the fabric. This odor-eliminating spray (Febreze
®
) has become a great success in the
USA marketed since 1998 ensuring a continuous demand for cyclodextrin production. Actually, cyclodextrins play an important role in the textile industry as a tool
to remove odors, e.g., encapsulation of sweat or cigarette smoke components permits to reduce the intensity of odors of clothing or furniture textiles, as showed in
Fig. 1.28. The mechanism of drug release is similar from medical textiles such as
antimicrobial textiles for wound dressing (Aubert-Viard et al. 2019), intraperitoneal
meshes (Chai et al. 2019), and other implants (Vermet et al. 2017). CycloMesh™, a
polyester visceral implant soaked in ropivacaine hydrochloride developed for slow
anesthetic release and in situ activity after inguinal hernia surgery, will be soon
subjected to clinical trials in France.
N. Morin-Crini et al.
cyclodextrins that enabled the improvement of different chromatographic
separations.
The first comprehensive review on potential applications in cosmetology, toiletry, and hygiene has been published by Szejtli (1982b). This topic was later
updated by Vaution et al. (1987), Hashimoto (1996, 2006), Citernesi and Sciacchitano
(1995), Buschmann and Schollmeyer (2002), and Duchêne et al. (2009). In the
mid- 1980s, some products appear in the market although the cyclodextrins were
often used without any indication of their precise role: Epicutin
®
TT, Chemishes
Laboratorium Dr Kurt Richter, a complex between cyclodextrin and Melaleuca
alternifolia leaf oil, used in skin care applications; Vivace
®
, Shiseifo Co., a powder
cologne; Klorane
®
, Klorane Laboratories, a dry shampoo; Novoflex
®
, Revlon, a
vitamin shampoo; Eucerin
®
Vital Active, Beiersdorf, a vitamin A cream; etc. In the
cosmetic industry, cyclodextrin complexes were useful for modifying solubility,
improving stabilization, transforming liquids into solids, preserving color, decreasing an unpleasant smell, or diminishing the odor of mercaptan used in permanent
hair preparations. Cyclodextrins were used as empty capsules in dry shampoos to
eliminate fatty substances such as sebum, or in toothpaste and mouthwash to remove
undesirable odors (Duchêne et al. 2009).
In the 1980s, applications were found in textiles including textile finishing and
functional textiles (Szejtli 1985; Hashimoto 1996; Buschmann and Schollmeyer
2002). The permanent fixation of cyclodextrin molecules offered textiles with interesting properties, e.g., the formation of body odor was reduced by the complexation, the release of perfumes from cyclodextrins was possible, etc. The first
cellulose- cyclodextrin copolymer was described in 1980 by Szejtli’s group. Alkaliswollen cellulose fibers were reacted with epichlorohydrin. The chemically bound
cyclodextrin retained its complex-forming ability and could be loaded with chemically and/or biologically active guests such as perfumes to prepare perfumed textiles or drugs to prepare medical bandages (Szejtli et al. 1980b). For instance,
Fig. 1.27 illustrates a guest exchange by a cellulose fiber containing cyclodextrin.
The process consists to load the fixed cyclodextrin molecules with perfume molecules. During wearing and by sweat humidity, excreted short-chain fatty acids displace and release the perfume molecules and will be in turn entrapped (Szejtli
2003). Procter & Gamble recognized that similar effects can be achieved without
chemical fixation by simple spraying of hydroxypropyl-β-cyclodextrin solution on
the fabric. This odor-eliminating spray (Febreze
®
) has become a great success in the
USA marketed since 1998 ensuring a continuous demand for cyclodextrin production. Actually, cyclodextrins play an important role in the textile industry as a tool
to remove odors, e.g., encapsulation of sweat or cigarette smoke components permits to reduce the intensity of odors of clothing or furniture textiles, as showed in
Fig. 1.28. The mechanism of drug release is similar from medical textiles such as
antimicrobial textiles for wound dressing (Aubert-Viard et al. 2019), intraperitoneal
meshes (Chai et al. 2019), and other implants (Vermet et al. 2017). CycloMesh™, a
polyester visceral implant soaked in ropivacaine hydrochloride developed for slow
anesthetic release and in situ activity after inguinal hernia surgery, will be soon
subjected to clinical trials in France.
N. Morin-Crini et al.