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Erschienen in: Polymer Bulletin 1/2018

20.04.2017 | Original Paper

Controlled release of fragrance with cross-linked polymers: synthesis and hydrolytic property of cross-linked amphiphilic copolymers bearing octanal-derived acetal moieties

verfasst von: Hisatoyo Morinaga, Hiroshi Morikawa, Takeshi Endo

Erschienen in: Polymer Bulletin | Ausgabe 1/2018

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Abstract

A cross-linked amphiphilic polymethacrylate, composed of hydrophobic octanal-derived acetal and hydrophilic poly(ethylene glycol) moieties, was synthesized with different degrees of hydrophilicity. The polymer hydrophilicity was estimated based on measurements of contact angles with water. Release of octanal was achieved in a biphasic system composed of hexane and an aqueous suspension of the polymers. The acetal moieties of the polymers were gradually hydrolyzed in an acidic solution, releasing octanal continuously for 600 h. The amount of released octanal increased with an increase in the hydrophilicity of the polymer under acidic conditions.

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Literatur
1.
Zurück zum Zitat Park SJ, Arshady R (2003) Microspheres, microcapsules and liposomes. Citus Books, London, pp 157–198 Park SJ, Arshady R (2003) Microspheres, microcapsules and liposomes. Citus Books, London, pp 157–198
2.
Zurück zum Zitat Ness J, Simonsen O, Symes K (2003) Microspheres, microcapsules and liposomes. Citus Books, London, pp 199–234 Ness J, Simonsen O, Symes K (2003) Microspheres, microcapsules and liposomes. Citus Books, London, pp 199–234
3.
Zurück zum Zitat Herrmann A (2007) Controlled release of volatiles under mild reaction conditions: from nature to everyday products. Angew Chem Int Ed 46:5836–5863CrossRef Herrmann A (2007) Controlled release of volatiles under mild reaction conditions: from nature to everyday products. Angew Chem Int Ed 46:5836–5863CrossRef
4.
Zurück zum Zitat Perry RJ (2005) In delivery system handbook for personal care and cosmetic products: technology, applications and formulations. William Andrew Publishing, Norwich, pp 667–682CrossRef Perry RJ (2005) In delivery system handbook for personal care and cosmetic products: technology, applications and formulations. William Andrew Publishing, Norwich, pp 667–682CrossRef
5.
Zurück zum Zitat Morinaga H, Morikawa H, Wang Y, Sudo A, Endo T (2009) Amphiphilic copolymer having acid-labile acetal in the side chain as a hydrophobe: controlled release of aldehyde by thermoresponsive aggregation–dissociation of polymer micelles. Macromolecules 42:2229–2235CrossRef Morinaga H, Morikawa H, Wang Y, Sudo A, Endo T (2009) Amphiphilic copolymer having acid-labile acetal in the side chain as a hydrophobe: controlled release of aldehyde by thermoresponsive aggregation–dissociation of polymer micelles. Macromolecules 42:2229–2235CrossRef
6.
Zurück zum Zitat Morinaga H, Morikawa H, Sudo A, Endo T (2009) Design of controlled releasing system: synthesis of an amphiphilic copolymer endowed with acid-labile side chains based on quaternarization of amine-containing prepolymer with benzyl halide having acetal moiety. J Polym Sci Part A: Polym Chem 47:3241–3247CrossRef Morinaga H, Morikawa H, Sudo A, Endo T (2009) Design of controlled releasing system: synthesis of an amphiphilic copolymer endowed with acid-labile side chains based on quaternarization of amine-containing prepolymer with benzyl halide having acetal moiety. J Polym Sci Part A: Polym Chem 47:3241–3247CrossRef
7.
Zurück zum Zitat Wang Y, Morinaga H, Sudo A, Endo T (2010) Synthesis of an amphiphilic polymer having hydrophobic acetal and hydrophilic pyrrolidone moieties and its application to persisting release of aldehyde as a pro-fragrance. J Polym Sci Part A: Polym Chem 48:3816–3822CrossRef Wang Y, Morinaga H, Sudo A, Endo T (2010) Synthesis of an amphiphilic polymer having hydrophobic acetal and hydrophilic pyrrolidone moieties and its application to persisting release of aldehyde as a pro-fragrance. J Polym Sci Part A: Polym Chem 48:3816–3822CrossRef
8.
Zurück zum Zitat Morinaga H, Morikawa H, Sudo A, Endo T (2010) A new water-soluble branched poly(ethylene imine) derivative having hydrolyzable imidazolidine moieties and its application to long-lasting release of aldehyde. J Polym Sci Part A: Polym Chem 48:4529–4536CrossRef Morinaga H, Morikawa H, Sudo A, Endo T (2010) A new water-soluble branched poly(ethylene imine) derivative having hydrolyzable imidazolidine moieties and its application to long-lasting release of aldehyde. J Polym Sci Part A: Polym Chem 48:4529–4536CrossRef
9.
Zurück zum Zitat Wang Y, Morinaga H, Sudo A, Endo T (2011) Synthesis of amphiphilic polyacetal by polycondensation of aldehyde and polyethylene glycol as an acid-labile polymer for controlled release of aldehyde. J Polym Sci Part A: Polym Chem 49:596–602CrossRef Wang Y, Morinaga H, Sudo A, Endo T (2011) Synthesis of amphiphilic polyacetal by polycondensation of aldehyde and polyethylene glycol as an acid-labile polymer for controlled release of aldehyde. J Polym Sci Part A: Polym Chem 49:596–602CrossRef
10.
Zurück zum Zitat Wang Y, Morinaga H, Sudo A, Endo T (2011) Synthesis of amphiphilic copolymer having acid-labile bicyclo bisoxazolidine in the side chain for controlled release of fragrance aldehyde. J Polym Sci Part A: Polym Chem 49:1881–1886CrossRef Wang Y, Morinaga H, Sudo A, Endo T (2011) Synthesis of amphiphilic copolymer having acid-labile bicyclo bisoxazolidine in the side chain for controlled release of fragrance aldehyde. J Polym Sci Part A: Polym Chem 49:1881–1886CrossRef
11.
Zurück zum Zitat Rudzinski WE, Dave AM, Vaishnav UH, Kumbar SG, Kulkarni AR, Aminabhavi TM (2002) Hydrogels as controlled release devices in agriculture. Des Monomer Polym 5:39–65CrossRef Rudzinski WE, Dave AM, Vaishnav UH, Kumbar SG, Kulkarni AR, Aminabhavi TM (2002) Hydrogels as controlled release devices in agriculture. Des Monomer Polym 5:39–65CrossRef
12.
Zurück zum Zitat Rudzinski WE, Chipuk T, Dave AM, Kumbar SG, Aminabhavi TM (2003) pH-sensitive acrylic-based copolymeric hydrogels for the controlled release of a pesticide and a micronutrient. J Appl Polym Sci 87:394–403CrossRef Rudzinski WE, Chipuk T, Dave AM, Kumbar SG, Aminabhavi TM (2003) pH-sensitive acrylic-based copolymeric hydrogels for the controlled release of a pesticide and a micronutrient. J Appl Polym Sci 87:394–403CrossRef
13.
Zurück zum Zitat Murthy N, Thng YX, Schuck S, Xu MC, Fréchet JMJ (2002) A novel strategy for encapsulation and release of proteins: hydrogels and microgels with acid-labile acetal cross-linkers. J Am Chem Soc 124:12398–12399CrossRef Murthy N, Thng YX, Schuck S, Xu MC, Fréchet JMJ (2002) A novel strategy for encapsulation and release of proteins: hydrogels and microgels with acid-labile acetal cross-linkers. J Am Chem Soc 124:12398–12399CrossRef
14.
Zurück zum Zitat Yoo MK, Seok WK, Sung YK (2004) Characterization of stimuli-sensitive polymers for biomedical applications. Macromol Symp 207:173–186CrossRef Yoo MK, Seok WK, Sung YK (2004) Characterization of stimuli-sensitive polymers for biomedical applications. Macromol Symp 207:173–186CrossRef
15.
Zurück zum Zitat Marappan S, Davenport C, Sarshar S (2007) ph sensitive prodrugs of 2,6-diisopropylphenol. U.S. Patent No. 7,250,412 Marappan S, Davenport C, Sarshar S (2007) ph sensitive prodrugs of 2,6-diisopropylphenol. U.S. Patent No. 7,250,412
16.
Zurück zum Zitat Soppimath KS, Kulkarni AR, Aminabhavi TM (2001) Chemically modified polyacrylamide-g-guar gum-based crosslinked anionic microgels as pH-sensitive drug delivery systems: preparation and characterization. J Control Release 75:331–345CrossRef Soppimath KS, Kulkarni AR, Aminabhavi TM (2001) Chemically modified polyacrylamide-g-guar gum-based crosslinked anionic microgels as pH-sensitive drug delivery systems: preparation and characterization. J Control Release 75:331–345CrossRef
17.
Zurück zum Zitat Smeets NMB, Hoare T (2013) Designing responsive microgels for drug delivery applications. J Polym Sci Part A: Polym Chem 51:3027–3043CrossRef Smeets NMB, Hoare T (2013) Designing responsive microgels for drug delivery applications. J Polym Sci Part A: Polym Chem 51:3027–3043CrossRef
18.
Zurück zum Zitat Hoffman AS (2012) Hydrogels for biomedical applications. Adv Drug Deliv Rev 64:18–23CrossRef Hoffman AS (2012) Hydrogels for biomedical applications. Adv Drug Deliv Rev 64:18–23CrossRef
19.
Zurück zum Zitat Hosoya R, Kato K (2001) Method for producing glycerol-α,β-unsaturated carboxylic acid ester. Japan Patent No. 2001-294555 A Hosoya R, Kato K (2001) Method for producing glycerol-α,β-unsaturated carboxylic acid ester. Japan Patent No. 2001-294555 A
Metadaten
Titel
Controlled release of fragrance with cross-linked polymers: synthesis and hydrolytic property of cross-linked amphiphilic copolymers bearing octanal-derived acetal moieties
verfasst von
Hisatoyo Morinaga
Hiroshi Morikawa
Takeshi Endo
Publikationsdatum
20.04.2017
Verlag
Springer Berlin Heidelberg
Erschienen in
Polymer Bulletin / Ausgabe 1/2018
Print ISSN: 0170-0839
Elektronische ISSN: 1436-2449
DOI
https://doi.org/10.1007/s00289-017-2030-2

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