ITFI20070093A1 - VITAMIN DERIVATIVE AND ITS PREPARATION AND USE. - Google Patents
VITAMIN DERIVATIVE AND ITS PREPARATION AND USE. Download PDFInfo
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- ITFI20070093A1 ITFI20070093A1 ITFI20070093A ITFI20070093A1 IT FI20070093 A1 ITFI20070093 A1 IT FI20070093A1 IT FI20070093 A ITFI20070093 A IT FI20070093A IT FI20070093 A1 ITFI20070093 A1 IT FI20070093A1
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- vitamin
- fabric
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- 238000002360 preparation method Methods 0.000 title claims description 8
- 150000003722 vitamin derivatives Chemical class 0.000 title description 5
- 239000004744 fabric Substances 0.000 claims description 24
- 239000000835 fiber Substances 0.000 claims description 21
- 239000004753 textile Substances 0.000 claims description 12
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims description 8
- 239000008103 glucose Substances 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 7
- 150000003712 vitamin E derivatives Chemical class 0.000 claims description 6
- 239000003995 emulsifying agent Substances 0.000 claims description 5
- 229920000742 Cotton Polymers 0.000 claims description 3
- 150000002402 hexoses Chemical group 0.000 claims description 3
- 150000002972 pentoses Chemical group 0.000 claims description 3
- 244000025254 Cannabis sativa Species 0.000 claims description 2
- 235000012766 Cannabis sativa ssp. sativa var. sativa Nutrition 0.000 claims description 2
- 235000012765 Cannabis sativa ssp. sativa var. spontanea Nutrition 0.000 claims description 2
- 240000000491 Corchorus aestuans Species 0.000 claims description 2
- 235000011777 Corchorus aestuans Nutrition 0.000 claims description 2
- 235000010862 Corchorus capsularis Nutrition 0.000 claims description 2
- WQZGKKKJIJFFOK-QTVWNMPRSA-N D-mannopyranose Chemical group OC[C@H]1OC(O)[C@@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-QTVWNMPRSA-N 0.000 claims description 2
- HMFHBZSHGGEWLO-SOOFDHNKSA-N D-ribofuranose Chemical group OC[C@H]1OC(O)[C@H](O)[C@@H]1O HMFHBZSHGGEWLO-SOOFDHNKSA-N 0.000 claims description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 2
- 239000004435 Oxo alcohol Substances 0.000 claims description 2
- 229920000297 Rayon Polymers 0.000 claims description 2
- PYMYPHUHKUWMLA-LMVFSUKVSA-N Ribose Chemical group OC[C@@H](O)[C@@H](O)[C@@H](O)C=O PYMYPHUHKUWMLA-LMVFSUKVSA-N 0.000 claims description 2
- HMFHBZSHGGEWLO-UHFFFAOYSA-N alpha-D-Furanose-Ribose Chemical group OCC1OC(O)C(O)C1O HMFHBZSHGGEWLO-UHFFFAOYSA-N 0.000 claims description 2
- WQZGKKKJIJFFOK-PHYPRBDBSA-N alpha-D-galactose Chemical group OC[C@H]1O[C@H](O)[C@H](O)[C@@H](O)[C@H]1O WQZGKKKJIJFFOK-PHYPRBDBSA-N 0.000 claims description 2
- 239000007864 aqueous solution Substances 0.000 claims description 2
- PYMYPHUHKUWMLA-WDCZJNDASA-N arabinose Chemical group OC[C@@H](O)[C@@H](O)[C@H](O)C=O PYMYPHUHKUWMLA-WDCZJNDASA-N 0.000 claims description 2
- PYMYPHUHKUWMLA-UHFFFAOYSA-N arabinose Chemical group OCC(O)C(O)C(O)C=O PYMYPHUHKUWMLA-UHFFFAOYSA-N 0.000 claims description 2
- SRBFZHDQGSBBOR-UHFFFAOYSA-N beta-D-Pyranose-Lyxose Chemical group OC1COC(O)C(O)C1O SRBFZHDQGSBBOR-UHFFFAOYSA-N 0.000 claims description 2
- 235000009120 camo Nutrition 0.000 claims description 2
- 235000005607 chanvre indien Nutrition 0.000 claims description 2
- 230000001804 emulsifying effect Effects 0.000 claims description 2
- 229930182830 galactose Chemical group 0.000 claims description 2
- 239000011487 hemp Substances 0.000 claims description 2
- 125000002791 glucosyl group Chemical group C1([C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)* 0.000 claims 2
- 238000001035 drying Methods 0.000 claims 1
- GVJHHUAWPYXKBD-UHFFFAOYSA-N (±)-α-Tocopherol Chemical compound OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 21
- 239000000047 product Substances 0.000 description 11
- 229930003427 Vitamin E Natural products 0.000 description 10
- WIGCFUFOHFEKBI-UHFFFAOYSA-N gamma-tocopherol Natural products CC(C)CCCC(C)CCCC(C)CCCC1CCC2C(C)C(O)C(C)C(C)C2O1 WIGCFUFOHFEKBI-UHFFFAOYSA-N 0.000 description 10
- 229940046009 vitamin E Drugs 0.000 description 10
- 235000019165 vitamin E Nutrition 0.000 description 10
- 239000011709 vitamin E Substances 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 5
- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 description 5
- ZAKOWWREFLAJOT-CEFNRUSXSA-N D-alpha-tocopherylacetate Chemical compound CC(=O)OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C ZAKOWWREFLAJOT-CEFNRUSXSA-N 0.000 description 4
- ZAKOWWREFLAJOT-UHFFFAOYSA-N d-alpha-Tocopheryl acetate Natural products CC(=O)OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C ZAKOWWREFLAJOT-UHFFFAOYSA-N 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 229940042585 tocopherol acetate Drugs 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- 229910015900 BF3 Inorganic materials 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical class [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 3
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 229940088594 vitamin Drugs 0.000 description 3
- 229930003231 vitamin Natural products 0.000 description 3
- 235000013343 vitamin Nutrition 0.000 description 3
- 239000011782 vitamin Substances 0.000 description 3
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
- 229940087168 alpha tocopherol Drugs 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 229920001429 chelating resin Polymers 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000010511 deprotection reaction Methods 0.000 description 2
- 238000003818 flash chromatography Methods 0.000 description 2
- 238000006386 neutralization reaction Methods 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 235000020374 simple syrup Nutrition 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 235000020357 syrup Nutrition 0.000 description 2
- 239000006188 syrup Substances 0.000 description 2
- 229960000984 tocofersolan Drugs 0.000 description 2
- 235000004835 α-tocopherol Nutrition 0.000 description 2
- 239000002076 α-tocopherol Substances 0.000 description 2
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 241000612703 Augusta Species 0.000 description 1
- ZZZCUOFIHGPKAK-UHFFFAOYSA-N D-erythro-ascorbic acid Natural products OCC1OC(=O)C(O)=C1O ZZZCUOFIHGPKAK-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 229930003268 Vitamin C Natural products 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 235000006708 antioxidants Nutrition 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 210000003850 cellular structure Anatomy 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 230000006196 deacetylation Effects 0.000 description 1
- 238000003381 deacetylation reaction Methods 0.000 description 1
- 239000002781 deodorant agent Substances 0.000 description 1
- FDSGHYHRLSWSLQ-UHFFFAOYSA-N dichloromethane;propan-2-one Chemical compound ClCCl.CC(C)=O FDSGHYHRLSWSLQ-UHFFFAOYSA-N 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 239000012156 elution solvent Substances 0.000 description 1
- 238000005858 glycosidation reaction Methods 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 239000004530 micro-emulsion Substances 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 239000012454 non-polar solvent Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 235000020777 polyunsaturated fatty acids Nutrition 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 229930003799 tocopherol Natural products 0.000 description 1
- 239000011732 tocopherol Substances 0.000 description 1
- 235000010384 tocopherol Nutrition 0.000 description 1
- 229960001295 tocopherol Drugs 0.000 description 1
- 235000019154 vitamin C Nutrition 0.000 description 1
- 239000011718 vitamin C Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
- C07H17/04—Heterocyclic radicals containing only oxygen as ring hetero atoms
- C07H17/06—Benzopyran radicals
- C07H17/065—Benzo[b]pyrans
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/10—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing oxygen
- D06M13/165—Ethers
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M2101/00—Chemical constitution of the fibres, threads, yarns, fabrics or fibrous goods made from such materials, to be treated
- D06M2101/02—Natural fibres, other than mineral fibres
- D06M2101/04—Vegetal fibres
- D06M2101/06—Vegetal fibres cellulosic
Description
Domanda di Brevetto per Invenzione Industriale dal titolo: Patent Application for Industrial Invention entitled:
Derivato della vitamina E sua preparazione ed uso Derivative of vitamin E its preparation and use
Campo dell'invenzione Field of the invention
La presente invenzione si riferisce a derivati della vitamina ed al loro uso in combinazione con fibre tessili. The present invention relates to vitamin derivatives and their use in combination with textile fibers.
Stato del’arte State of the art
Tessuti e capi di abbigliamento, ad esempio magliette, capaci di rilasciare sostanze quali antibatterici o deodoranti sono noti. Fabrics and items of clothing, for example T-shirts, capable of releasing substances such as antibacterials or deodorants are known.
In particolare sono prodotte da alcuni anni magliette comprendenti o costituite di fibre particolari capaci di rilasciare Vitamina C per semplice sfregamento sulla pelle. In particular, T-shirts comprising or consisting of particular fibers capable of releasing Vitamin C by simple rubbing on the skin have been produced for some years.
D’altra parte sono in corso studi per migliorare o rendere ancora più ampio lo spettro di sostanze fatte aderire a fibre tessili e assimilabili attraverso la pelle tenendo conto dei vari problemi che questo comporta. On the other hand, studies are underway to improve or widen the spectrum of substances made to adhere to textile fibers and assimilable through the skin, taking into account the various problems that this entails.
Si tratta infatti di trovare il modo di far aderire la sostanza voluta alla fibra tessile in modo che questa venga poi lentamente rilasciata ed adsorbita attraverso la pelle dell’utente ma bisogna che far sì che essa resista sulla fibra almeno per un discreto numero di lavaggi cui l’indumento verrà sottoposto. In fact, it is a question of finding a way to make the desired substance adhere to the textile fiber so that it is then slowly released and adsorbed through the user's skin but it is necessary to ensure that it resists on the fiber at least for a fair number of washes. the garment will be submitted.
In particolare, come si sa, la Vitamina E è un composto oleoso, insolubile in acqua e solubile nei solventi apolari. In particular, as we know, Vitamin E is an oily compound, insoluble in water and soluble in non-polar solvents.
La vitamina E è nota per il suo potere antiossidante in particolare per l’azione di prevenzione di ossidazione degli acidi grassi poliinsaturi limitando la formazione dei radicali liberi e gioca quindi un ruolo essenziale nel salvaguardare dall’invecchiamento precoce e marcato le strutture cellulari. Vitamin E is known for its antioxidant power, in particular for the action of preventing the oxidation of polyunsaturated fatty acids by limiting the formation of free radicals and therefore plays an essential role in safeguarding cellular structures from premature and marked aging.
Descrizione dettagliata dell’invenzione Detailed description of the invention
La presente invenzione risponde alle esigenze suddette grazie ad un derivato della vitamina E che consente un facile e stabile fissaggio della vitamina e alle fibre tessili (naturali e artificiali) ed allo stesso tempo ne permette il lento rilascio e l’adsorbimento attraverso la pelle dell’utente. L’invenzione si riferisce inoltre a fibre tessili, tessuti e capi di abbigliamento ai quali, o a parte dei quali, è stato applicato detto derivato. The present invention responds to the aforementioned needs thanks to a derivative of vitamin E which allows an easy and stable fixing of the vitamin and to the textile fibers (natural and artificial) and at the same time allows its slow release and adsorption through the skin of the user. The invention also refers to textile fibers, fabrics and clothing items to which, or part of which, said derivative has been applied.
In particolare fra i capi di abbigliamento secondo l’invenzione sono preferiti quelli che si portano comunemente a contatto con la pelle come sciarpe, T-shirt, magliette, camicie, biancheria intima, ecc. In particular, among the items of clothing according to the invention, those that are commonly worn in contact with the skin such as scarves, T-shirts, T-shirts, shirts, underwear, etc. are preferred.
In particolare, nel caso dei capi di abbigliamento secondo l’invenzione questi possono ovviamente essere confezioni con tessuti già comprendenti la Vitamina E secondo l’invenzione o possono essere sottoposti al processo di caricamento della Vitamina E dopo essere stati confezionati con tessuti tradizionali. In particular, in the case of clothing according to the invention, these can obviously be packages with fabrics already comprising Vitamin E according to the invention or they can be subjected to the Vitamin E loading process after being packaged with traditional fabrics.
Secondo l’invenzione il derivato della Vitamina E è un prodotto di formula (I): According to the invention, the Vitamin E derivative is a product of formula (I):
(I) (THE)
in cui R è un esoso od un pentoso where R is a hexose or a pentose
Secondo l’invenzione per zucchero si intende un esoso o pentoso come ad esempio: glucosio, mannosio, ribosio, arabinosio, galattosio ecc. Preferito secondo l’invenzione è il glucosio. According to the invention, sugar means a hexose or pentose such as: glucose, mannose, ribose, arabinose, galactose, etc. Preferred according to the invention is glucose.
Secondo l’invenzione un prodotto di formula (I) particolarmente preferito è il a-tocoferil-β-o-glucopiranoside racemo. According to the invention, a particularly preferred product of formula (I) is racemic a-tocopheryl-β-o-glucopyranoside.
Il prodotto secondo l’invenzione può essere prodotto secondo tecniche di sintesi note. The product according to the invention can be produced according to known synthesis techniques.
Ad esempio, un processo di preparazione prevede la reazione dello zucchero, i cui gruppi OH sono stati preventivamente protetti, con atocoferolo puro seguita da eventuale purificazione ed infine deprotezione dei gruppi precedentemente protetti e neutralizzazione ed eliminazione di solvente. For example, a preparation process involves the reaction of the sugar, whose OH groups have been previously protected, with pure atocopherol followed by eventual purification and finally deprotection of the previously protected groups and neutralization and elimination of solvent.
La protezione dei gruppi OH si effettua con gruppi facilmente idrolizzabili come, ad esempio, i gruppi acile e acetile, preferito, secondo l’invenzione, è il gruppo acetile. The protection of the OH groups is carried out with easily hydrolyzable groups such as, for example, the acyl and acetyl groups, preferred, according to the invention, is the acetyl group.
La protezione si effettua secondo metodi noti, ad esempio con sodio acetato ed anidride acetica. The protection is carried out according to known methods, for example with sodium acetate and acetic anhydride.
Preferibilmente si utilizzano quantità equimolare di zucchero protetto e α-tocoferolo usando come catalizzatore boro-trifluoruro. Equimolar quantities of protected sugar and α-tocopherol are preferably used using boron trifluoride as catalyst.
La reazione è preferibilmente condotta in un solvente organico come diclorometano alla temperatura di 18° - 25°C. The reaction is preferably carried out in an organic solvent such as dichloromethane at the temperature of 18 ° - 25 ° C.
L’eventuale purificazione del prodotto ottenuto, se necessaria, può essere eseguita per flash cromatografia ad esempio con SILICA GEL 60 (200-400 mesh). Any purification of the obtained product, if necessary, can be performed by flash chromatography, for example with SILICA GEL 60 (200-400 mesh).
La deprotezione si effettua preferibilmente in ambiente basico, ad esempio utilizzando sodio metossido metilato e neutralizzando successivamente la soluzione ottenuta ad esempio con una resina a scambio ionico come AMBERLITE IR 120 H<+>. Deprotection is preferably carried out in a basic environment, for example using methylated sodium methoxide and subsequently neutralizing the solution obtained for example with an ion exchange resin such as AMBERLITE IR 120 H <+>.
Se preferito, anziché da α-tocoferolo puro si può partire da atocoferolo-acetato (prodotto commercialmente reperibile) che verrà in questo caso preventivamente disacetìlizzato e analogamente partire da zucchero e procedere alla protezione dei gruppi OH utilizzando il gruppo protettore preferito e procedere poi come sopra indicato. If preferred, instead of pure α-tocopherol, it is possible to start from atocopherol-acetate (commercially available product) which in this case will be previously disacetylized and similarly start from sugar and proceed with the protection of the OH groups using the preferred protecting group and then proceed as above indicated.
Il prodotto così ottenuto (a-tocoferilβ-o-glucopiranoside racemo) viene quindi applicato al tessuto, o alle fibre tessili, desiderato per immersione di questo in una soluzione acquosa contenenti opportuni emulsionatori noti, capaci di emulsionare il prodotto che di per sé è insolubile in acqua. The product thus obtained (racemic a-tocopherylβ-o-glucopyranoside) is then applied to the desired fabric or textile fibers by immersion of this in an aqueous solution containing suitable known emulsifiers, capable of emulsifying the product which in itself is insoluble. in water.
Il fissaggio prodotto/fibra avviene grazie alla presenza dei gruppi OH della cellulosa costituente le fibre e del glucosio, inoltre l’analogia strutturale fra il composto e le fibre ne favorisce la sovrapposizione e quindi l’adesione reciproca. The product / fiber fixing takes place thanks to the presence of the OH groups of the cellulose constituting the fibers and glucose, furthermore the structural analogy between the compound and the fibers favors their overlap and therefore mutual adhesion.
Esempi di possibili emulsionatori secondo l’invenzione sono gli oxo alcoli contenenti ossido di etilene (ad esempio Lialet 123-3<®>(Chimica Augusta, Italia) o Neopal Ma 8). Examples of possible emulsifiers according to the invention are oxo alcohols containing ethylene oxide (for example Lialet 123-3 <®> (Chimica Augusta, Italy) or Neopal Ma 8).
Si possono utilizzare fibre o tessuti naturali e artificiali come ad esempio cotone, viscosa, lino, canapa, juta ecc. Natural and artificial fibers or fabrics can be used such as cotton, viscose, linen, hemp, jute etc.
Secondo una particolare realizzazione dell’invenzione le fibre od i tessuti possono venire trattati direttamente con un derivato stabile di Vitamina E e sciroppo di zucchero opportunamente emulsionati. According to a particular embodiment of the invention, the fibers or fabrics can be treated directly with a stable derivative of Vitamin E and suitably emulsified sugar syrup.
Fra i derivati stabili di Vitamina E particolarmente preferito è l’acetato. Lo sciroppo di zucchero si ottiene sciogliendo lo zucchero in acqua (normalmente in quantità pari al 40% in peso) e utilizzando come emulsionanti gli stessi sopra indicati. Among the stable derivatives of Vitamin E, acetate is particularly preferred. Sugar syrup is obtained by dissolving the sugar in water (normally in quantities equal to 40% by weight) and using the same ones indicated above as emulsifiers.
Anche in questo caso si preferisce come zucchero il glucosio. Also in this case glucose is preferred as sugar.
Normalmente il rapporto molare fra zucchero e vitamina E acetato utilizzati è compreso fra 0,3 e 1. Normally the molar ratio between sugar and vitamin E acetate used is between 0.3 and 1.
Per meglio chiarire l’invenzione si riportano qui di seguito alcuni esempi. To better clarify the invention, some examples are given below.
Esempio 1 Example 1
Preparazione di a-tocoferil-β-o-glucopiranoside racemo Glicosidazione Preparation of racemic a-tocopheryl-β-o-glucopyranoside Glycosidation
In un pallone si versano 150cc di diclorometano, poi si aggiungono 4,3g. di all-rac a tocoferolo, agitando per 5 min. e aggiungendo poi 3,9g. di β-pentaacetil glucosio. 150cc of dichloromethane are poured into a flask, then 4.3g are added. of all-rac to tocopherol, stirring for 5 min. and then adding 3.9g. of β-pentaacetyl glucose.
Si agita per altri 5 min. e si aggiungono 3 cc. di BF3 etil eterato, continuando ad agitare per 45 minuti a temperatura ambiente al buio, si raffredda con ghiaccio e si elimina l’eccesso di BF3 con sodio bicarbonato; infine si evapora il solvente. It is stirred for another 5 min. and 3 cc are added. of BF3 ethyl etherate, continuing to stir for 45 minutes at room temperature in the dark, cool with ice and remove the excess of BF3 with sodium bicarbonate; finally the solvent is evaporated.
Purificazione Purification
Si purifica il prodotto sopra ottenuto con flash cromatografia su colonna con SILICA GEL 60 (200-400 mesh), usando come solvente di eluizione diclorometano-acetone. The above product is purified by flash chromatography on column with SILICA GEL 60 (200-400 mesh), using dichloromethane-acetone as elution solvent.
Deacetilazione e neutralizzazione Deacetylation and neutralization
Il prodotto purificato è sciolto in metanolo e vi si aggiunge, goccia a goccia, sodio metossido metilato fino a pH 8. The purified product is dissolved in methanol and sodium methoxide methylated up to pH 8 is added drop by drop.
Si neutralizza con colonna contenente AMBERLITE 120H+, si filtra e si concentra ottenendo uno sciroppo molto denso, giallognolo, costituito da a-tocoferil- -o-glucopiranoside racemo It is neutralized with a column containing AMBERLITE 120H +, filtered and concentrated to obtain a very dense, yellowish syrup, consisting of racemic a-tocopheryl- -o-glucopyranoside
Esempio 2 Example 2
Preparazione della miscela glucosio/Vitamina E acetato Preparation of the glucose / Vitamin E acetate mixture
In un miscelatore dotato di agitatore ad elica si pongono 896 gr di acqua a cui si aggiungono 24 gr di Lialet 123-3© e 40 gr di NEOPAL MA 8© mescolando per circa 10 minuti. Place 896 g of water in a mixer equipped with a propeller stirrer, to which 24 g of Lialet 123-3 © and 40 g of NEOPAL MA 8 © are added, mixing for about 10 minutes.
Si versano quindi nella miscela 5 gr di sciroppo di glucosio al 38% mescolando per latri 10 minuti ed infine 5 gr di vitamina E acetato mescolando il tutto per altri 30 minuti. Then 5 g of 38% glucose syrup are poured into the mixture, stirring for another 10 minutes and finally 5 g of vitamin E acetate, mixing everything for another 30 minutes.
Si aggiungono 30 gr. di MORBIREX MIC-HP<©>(una micro emulsione siliconica al 42% che conferisce mano morbida e aumenta la resistenza della vitamina ai lavaggi) e si prosegue il mescolamento per altri 10 minuti aggiustando, se necessario, il pH a 6 - 7. Add 30 gr. of MORBIREX MIC-HP <©> (a 42% silicone micro emulsion that gives a soft touch and increases the resistance of the vitamin to washing) and continue mixing for another 10 minutes, adjusting, if necessary, the pH to 6 - 7.
Il prodotto così ottenuto è pronto per essere applicato al prodotto. The product thus obtained is ready to be applied to the product.
Esempio 3 Example 3
Applicazione al tessuto Application to the fabric
Un tessuto a maglia tipo Jersey 100% cotone, purgato e pronto per la tinta viene trattato con la miscela ottenuta nell’esempio 2 usando un Foulard. A 100% cotton jersey-type knitted fabric, purged and ready for dyeing, is treated with the mixture obtained in example 2 using a foulard.
Si versa quindi la miscela come ottenuta nell’esempio precedente nella vaschetta del Foulard e si impregna il tessuto, il rapporto di spremitura (inteso come la percentuale di bagno assorbita dal tessuto rispetto al suo peso) è del 90%. Il tessuto viene quindi essiccato a 140°C. The mixture as obtained in the previous example is then poured into the Foulard tub and the fabric is soaked, the squeezing ratio (understood as the percentage of bath absorbed by the fabric with respect to its weight) is 90%. The fabric is then dried at 140 ° C.
All’analisi risulta che il tessuto presenta 4.027 mg di Vitamina E per 1000 gr di tessuto si ha pertanto un adesione pressoché totale della Vitamina E utilizzata al tessuto trattato. The analysis shows that the tissue has 4,027 mg of Vitamin E per 1000 g of tissue, therefore there is an almost total adhesion of the Vitamin E used to the treated tissue.
Esempio 4 Example 4
Prova di lavaggio Washing test
Un campione del tessuto trattato come suddetto viene sottoposto a 5 cicli di lavaggio eseguiti secondo la norma ISO 6330 ciclo 6A (40° C). A sample of the fabric treated as above is subjected to 5 washing cycles performed according to ISO 6330 cycle 6A (40 ° C).
Dopo detto ciclo di lavaggi si riscontra una quantità di Vitamina E rimasta sul tessuto pari a 2.450 mg per 1000 gr di tessuto pari a circa il 60% della vitamina inizialmente aderita al tessuto. After said washing cycle there is a quantity of Vitamin E left on the fabric equal to 2,450 mg per 1000 g of fabric equal to about 60% of the vitamin initially adhered to the fabric.
Esempio 5 Example 5
Prova di cessione per indossamento Proof of transfer by wearing
Con parte del tessuto trattato secondo l’esempio 3 si confeziona una maglietta da donna che viene indossata a diretto contato con la pelle per 79 ore (pari a quasi 10 giorni di indossamento a 8 ore al giorno). Al termine della prova l’analisi mostra un residuo di Vitamina E sul capo pari a 3,005 mg per chilo di maglietta che prova la cessione di Vitamina E ala pelle per circa un 25% rispetto al quantitativo iniziale. With part of the fabric treated according to example 3, a women's t-shirt is made which is worn in direct contact with the skin for 79 hours (equal to almost 10 days of wearing at 8 hours a day). At the end of the test, the analysis shows a residual of Vitamin E on the garment equal to 3.005 mg per kilo of t-shirt which proves the release of Vitamin E to the skin for about 25% of the initial quantity.
Ovviamente aumentando la quantità di Vitamina E acetato utilizzata nella preparazione della miscela zuccherina da applicare al tessuto si potranno caricare i tessuti con quantità maggiori di Vitamina E dosandone quindi la presenza sul tessuto come desiderato. Obviously, by increasing the quantity of Vitamin E acetate used in the preparation of the sugar mixture to be applied to the fabric, it is possible to load the fabrics with greater quantities of Vitamin E, thus dosing its presence on the fabric as desired.
Claims (1)
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ITFI20070093 ITFI20070093A1 (en) | 2007-04-17 | 2007-04-17 | VITAMIN DERIVATIVE AND ITS PREPARATION AND USE. |
| PCT/EP2008/054605 WO2008125683A1 (en) | 2007-04-17 | 2008-04-16 | Derivative of vitamin e, its preparation and use |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ITFI20070093 ITFI20070093A1 (en) | 2007-04-17 | 2007-04-17 | VITAMIN DERIVATIVE AND ITS PREPARATION AND USE. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ITFI20070093A1 true ITFI20070093A1 (en) | 2008-10-18 |
Family
ID=39580274
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ITFI20070093 ITFI20070093A1 (en) | 2007-04-17 | 2007-04-17 | VITAMIN DERIVATIVE AND ITS PREPARATION AND USE. |
Country Status (2)
| Country | Link |
|---|---|
| IT (1) | ITFI20070093A1 (en) |
| WO (1) | WO2008125683A1 (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ITVR20120104A1 (en) * | 2012-05-22 | 2013-11-23 | Paolo Srl O | PROCESS OF TREATMENT OF FABRICS INTENDED TO GO TO CONTACT WITH THE HUMAN BODY |
| CN106478745B (en) * | 2016-10-14 | 2019-02-05 | 高介平 | A kind of formaldehyde-free aqueous crosslinking agent and preparation method thereof and finishing technique to fabric |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR920700652A (en) * | 1989-11-08 | 1992-08-10 | 미끼 도꾸따로 | Medicine containing tocopheryl glycoside as an active ingredient |
| JP3721311B2 (en) * | 2001-04-18 | 2005-11-30 | 富士紡ホールディングス株式会社 | Functionalized fiber material and manufacturing method thereof |
| DE202004010472U1 (en) * | 2004-07-02 | 2004-09-23 | Mattes & Ammann Kg | Knitted or woven textile sheet material, e.g. of cotton, polyester and polyamide, used for clothing, e.g. T-shirt, or mattress cover, is treated with skin care mixture of cyclodextrin and vitamin E |
-
2007
- 2007-04-17 IT ITFI20070093 patent/ITFI20070093A1/en unknown
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2008
- 2008-04-16 WO PCT/EP2008/054605 patent/WO2008125683A1/en active Application Filing
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| Publication number | Publication date |
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| WO2008125683A1 (en) | 2008-10-23 |
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