Application
of
Cyclodextrin
on
textile
for
Cosmetic
Purpose
April‐June2010
Prof
Bojana
Vončina
Yohann
Lachette
Application
of
Cyclodextrin
on
Textile
for
Cosmetic
Purpose
2
Yohann
Lachette
Application
of
Cyclodextrin
on
Textile
for
Cosmetic
Purpose
Contents Acknowledgements.............................................................................................................4 Glossary...................................................................................................................................5
Abstract..................................................................................................................................6 Introduction...........................................................................................................................7 I.
All about Slovenia.........................................................................................................8 1. Slovenia.........................................................................................................................8 1. Republic of Slovenia.....................................................................................................8 2. Few major dates of modern Slovenia...........................................................................9 3. Economy .....................................................................................................................9 2. Maribor.........................................................................................................................10 1. The city ......................................................................................................................10 2. University ...................................................................................................................10
II.
Particles on textile......................................................................................................11
1.
Cyclodextrin................................................................................................................11 Generality ..................................................................................................................11 Method of Application on textile.................................................................................12 2. Cosmetic particles......................................................................................................13 1. Vanillin.........................................................................................................................13 2. Method of Application on textile...................................................................................14 3. Analysis Method..........................................................................................................14 1. 2.
III.
Results and Discussion.............................................................................................15
1. Β-Cyclodextrin.............................................................................................................15 1. Polyester.....................................................................................................................16 2. Cotton..........................................................................................................................18 3. Viscose........................................................................................................................20 4. Discussion about results.............................................................................................22 2. Vanillin..........................................................................................................................23 Conclusion............................................................................................................................25 Bibliography..........................................................................................................................26
Yohann
Lachette
3
Application
of
Cyclodextrin
on
Textile
for
Cosmetic
Purpose
Acknowledgements: I would like to thanks: -Prof Bojana Voncina, for being my mentor at the host university, giving me good advices and for helping me. -Vera Vivod, for being my second mentor, her attention, all the time she awarded to me. Her advice was really useful and appreciated. -Ramona Irgolič, Tina Jerič,Tanja Kos, Ernest Šimon, Simona Vajnhandl, Julija Volmajer Valh for their welcome, their help and their happiness. - Jitka, Merve and Vickie my students co-workers, for their help and their good mood. - Mr. Arnaud Cailler, French Erasmus coordinator for gave me all his attention. - Both university of Maribor and IUT “A” de Lille 1 for according me to do my training course in a foreign country.
4
Yohann
Lachette
Application
of
Cyclodextrin
on
Textile
for
Cosmetic
Purpose
Abbreviations Abbreviation in order of appearance: GDP = Gross Domestic Product β-CD = β-Cyclodextrin CD = Cyclodextrin BTCA = Butane tetracarboxylic acid SHPI = sodium hypophosphite monohydrate ADHF = ammonium hydrogen phosphate A”number”T = after “number” treatment(s) “number”W = “number” washing(s)
5
Yohann
Lachette
Application
of
Cyclodextrin
on
Textile
for
Cosmetic
Purpose
Abstract The subject of my training period was application of Cyclodextrin on textile for cosmetic purpose. Textile substrates treated with β-CD can be important for medical and hygienic textiles, the strong ability of complexing fragrances can also be used for the garments in cosmetotextile and for home textiles. I decided to make three treatments on textile to increase the gain on masse. I have to choose the best way to fix vanillin on textile and stay on it. I used UV-VIS detector to prove the vanillin stay on textile.
6
Yohann
Lachette
Application
of
Cyclodextrin
on
Textile
for
Cosmetic
Purpose
Introduction I worked in technique faculty of Maribor during 3 months. I was in the textile department. The main topic of my training period was the application of cyclodextrin on textile for cosmetic purpose. Cosmetotextile are more and more present in our life, one of the way to fabric it it’s to use βcyclodextrin and add some cosmetic particle after. A presentation about Slovenia is introduced in the first chapter 1 then β-cyclodextrin and vanillin are explained in chapter 2 and finally the results are given in chapter 4.
7
Yohann
Lachette
Application
of
Cyclodextrin
on
Textile
for
Cosmetic
Purpose
I: All about Slovenia I.1: Slovenia I.1.1: Republic of Slovenia
Figure1 : Slovenian Flag National Anthem:
7th stanza of Zdravljica “A Toast”
Capital:
Ljubljana
Official Languages:
Slovenian
Government: President: Prime Minister:
Parliamentary Republic Danilo Türk
Borut Pahor
Independence: Declared: Recognized:
from Yugoslavia
June 25th, 1991 1992
Area: Population: Density:
20.273 km² 2.009.245 99 ina/km²
Currency:
Euro (€)
8
Yohann
Lachette
Application
of
Cyclodextrin
on
Textile
for
Cosmetic
Purpose
I.1.2: Few majors dates of modern Slovenia July 20th, 1917: The pact of Corfu was signed between the Croats, Serbs and Slovenes to form Yugoslavia. October 3rd, 1929: The kingdom of Serbs, Croats and Slovenes formally changed its name to the name of Yugoslavia. February, 1989: The Slovenes formed an opposition party to Communist rule. June 25th, 1991: Slovenia proclaimed independence from Yugoslavia. October 8th, 1991: Slovenia and Croatia began operating independently from Yugoslavia. May 1st, 2004: Slovenia joined European Union. January, 2007: Slovenia adopt the Euro
I.1.3: Economy Slovenia is the richest country of ex-Yugoslavia has a 4% economic growth per year since 1994. Service sector is the most important in Slovenian economy with 54, 7% of labour people and 64,2% of Gross Domestic Product(GDP). For instance, banks are specially developed. Mines and industries represent 39, 8% of labour people and 32,7% of GDP. Principal Fields are chemicals factories, automobiles, consumer good, metallurgy and wood factories. And finally there is agriculture with 5, 5% of labour people and 3, 1% of GDP. The smallness of Slovenia prevents farming from developing. Mains farming are corn, sugar beet and potato. Slovenia is known for viticulture and dairy farms.
Yohann
Lachette
9
Application
of
Cyclodextrin
on
Textile
for
Cosmetic
Purpose
I.2: Maribor I.2.1: The city
Figure 2: Maribor flag Maribor is the second-largest city in Slovenia, with 117.693 inhabitants. Maribor lies on the Drava River at the meeting point of the Pohorje Moutain, the Drava valley, the Drava plain and the Kozkak and Slovenske gorice hill ranges. It is the centre of the Slovenian region of Lower Styria and its largest city. Maribor’s coat of arms features a white pigeon flying downwards a white castle with two towers and a portcullis on a red shield.
I.2.2: University University of Maribor, second university of Slovenia, was created in 1975. Currently, there are 13 faculties. In 2004/2005, there were 21.273 students in licence and master, 1.787 in doctorate, 1.360 professors, research professor, and research assistant worked for university. Mr Ivan Rozman is the chief education officer.
10
Yohann
Lachette
Application
of
Cyclodextrin
on
Textile
for
Cosmetic
Purpose
Figure 3: Main building of university
II: Particle on Textile II.1: Cyclodextrin One of the new concepts for modification of textile substrates is based on the permanent fixation of supramolecular compounds, such as β-cyclodextrin on the material surface and thus imparts new functionality to the fabric.
II.1.1: Generality Cyclodextrins (CD) are cyclic oligosaccharides being macrocyclic compounds built from glucopyranose units by α-(1, 4)-glycosidc bonds. CD can be obtained by enzymatic degradation of starch. In this process compounds with six to twelve glucopyranose units per ring are produced. Depending on the enzyme and the way the reaction is controlled; the main product is α, β or γ-Cyclodextrin (6, 7 and 8 glucopyranose units, respectively). They are of circular and conical conformation, where the height is about 800pm. The inner diameter of the cavity varies from 500 to 800 pm. Commercially most interesting is the β-cyclodextrin because of its simple production, availability, cavity diameter and price. It is most widely used and presents at least 95% of all produced and consumed CDs. CDs are able to form host-guest complexes with various hydrophobic molecules. Textile substrates treated with β-CD can be important for medical and hygienic textiles, the strong ability of complexing fragrances can also be used for the garments in cosmetotextile and for home textiles. From the structure of β-CD it is evident that it is unreactive; several blinders and polyfunctional reagents have been used to link β-CD on textile substrates, mainly on cotton or viscose fibres.
Yohann
Lachette
11
Application
of
Cyclodextrin
on
Textile
for
Cosmetic
Purpose
Figure
4:
Structure
of
β‐cyclodextrin
II.1.2: Method of Application on Textile
Cotton, polyester and viscose fabrics immersed in the treating baths. The bath contains 8g of β-cyclodextrin, 6g of butane tetracarboxylic acid (BTCA), 3 g of sodium hypophosphite monohydrate (SHPI), 1 g ammonium hydrogen phosphate (ADHF) and 100 mL of Water. The distilled water was warmed till 85°C add β-CD. When the solution was colourless the BTCA was added, then the ammonium and finally the SHPI. The pH of prepared solution was 2,8. The sample was passed two times in Foulard with pressure of 1 bar and 3tr/min. All the samples were dried at 100°C during 10 minutes. The fixation was carried out from 150°C to 170°C for 10 minutes, to saw the influence of the temperature of fixation. All the samples were rinsed with distilled water and dried fix in oven at 100°C for 10 minutes. For some samples I decided to make 3 treatments to see the influence of number of treatments on gain on masse and to see if better result can be obtain.
12
Yohann
Lachette
Application
of
Cyclodextrin
on
Textile
for
Cosmetic
Purpose
II.2: Vanillin II.2.1: Generality Vanillin is an organic compound with the molecular formula C8H8O3. Its groups include aldehyde, ether, and phenol. It is the primary component of the extract of the vanilla bean. It is also found in roasted coffee and the Chinese red pine. Synthetic vanillin, instead of natural vanilla extract, is sometimes used as a flavoring agent in foods, beverages, and pharmaceuticals. In 1970, more than half the world's vanillin production was used in the synthesis of other chemicals, but as of 2004 this use accounts for only 13% of the market for vanillin.
Figure 5: Structure of Vanillin
13
The annual demand for vanillin was 12,000 tons, but only 1800 tons of natural vanillin was produced
Guaiacol is the precursor of synthesis vanillin.
Yohann
Lachette
Application
of
Cyclodextrin
on
Textile
for
Cosmetic
Purpose
Figure 6: Structure of Guaiacol
Figure 7: Synthesis of Vanillin from guaiacol
Guaiacol (1) reacts with glyoxylic acid by electrophilic aromatic substitution. The resulting vanillylmandelic acid (2) is then converted via 4-Hydroxy-3-methoxyphenylglyoxylic acid (3) to vanillin (4) by oxidative decarboxylation.
II.2.2: Method of Application on Textile β-cyclodextrin attached to the material should form complex with vanillin. The best condition to obtain complexes was studied. To obtain the best result I made different experiments. I decided to immerse my sample in vanillin solution (10g/L) at different temperature from ambient to 100°C with or without stir and at different time from 10 minutes to 1 hour. The best result is for 100°C, with stirring and during 1 hour. Treated samples were dried at room temperature.
II.2.3: Analysis Method
Yohann
Lachette
14
Application
of
Cyclodextrin
on
Textile
for
Cosmetic
Purpose
Each sample was put into 40 mL of distilled water for 72 hours with continuous shaking. Each day 1 mL of the solution was extract and dilute in 100ml of volumetric flask and measurements of prepared solutions have been done.
III: Results and discussion III.1: β-Cyclodextrin The results of β-Cyclodextrin are about the gain of Masse, one for the treatment and one for the washing resistance. For the treatment, I made three treatments on some samples to see if there will be increase the gain on masse. For the washing resistance, I want to know how much of β-cyclodextrin is still present on the material when the sample is washed. The graphic represents the evolution of the gain on masse in function of the number of treatment or of the number of the washing.
15
Yohann
Lachette
Application
of
Cyclodextrin
on
Textile
for
Cosmetic
Purpose
III.1.1: Polyester Gain on Masse of polyester samples after first, second and third treatment
Polyester
T
T°
of
Treatment
16
17
18
3
7
10
4
5
19
20
21
13
14
15
9
12
22
23
24
6
8
11
150°
150°
150°
150°
150°
150°
150°
150°
160°
160°
160°
160°
160°
160°
160°
160°
170°
170°
170°
170°
170°
170°
Gain
on
Masse
A1T
11,58%
10,24%
10,08%
12,23%
11,41%
11,27%
10,53%
12,26%
13,28%
10,81%
10,61%
10,04%
9,91%
10,69%
11,15%
10,05%
11,30%
14,82%
11,33%
12,40%
11,31%
9,30%
Gain
of
Masse
A2T
22,77%
20,25%
20,37%
21,88%
22,86%
21,27%
18,08%
21,55%
22,03%
21,62%
25,05%
23,59%
21,01%
Gain
on
Masse
A3T
33,05%
35,11%
32,88%
33,78%
16
Yohann
Lachette
Application
of
Cyclodextrin
on
Textile
for
Cosmetic
Purpose
1
2
170°
170°
12,37%
13,16%
23,19%
31,87%
33,26%
44,16%
The third treatment on polyester at 170°C is the best treatment with 44,16% gain on masse. Gain on Masse of polyester samples after 20 washings. Polyester
W
4
5
9
12
1
2
T°
of
Treatment
150°
150°
160°
160°
170°
170°
Gain
on
Gain
on
Gain
on
Gain
on
Gain
on
Gain
on
Masse
1W
Masse
2W
Masse
5W
Masse
10W
Masse
15W
Masse
20W
28,14%
26,10%
21,46%
14,71%
8,90%
2,82%
31,14%
28,24%
22,74%
16,06%
10,38%
5,41%
29,73%
27,24%
22,49%
16,25%
10,40%
4,33%
30,51%
28,65%
23,85%
16,90%
11,06%
6,07%
29,91%
28,49%
25,15%
19,32%
13,64%
7,95%
40,75%
39,21%
34,94%
27,29%
18,56%
11,75%
Treatment Gain of Masse 50,00%
45,00%
40,00%
35,00%
30,00%
150°C
25,00%
160°C
20,00%
170°C
15,00%
10,00%
5,00%
0,00%
Gain
on
Masse
A1T
Gain
on
Masse
A2T
Gain
on
Masse
A3T
Washing Gain of Masse
17
Yohann
Lachette
Application
of
Cyclodextrin
on
Textile
for
Cosmetic
Purpose
50,00%
45,00%
40,00%
35,00%
30,00%
25,00%
150°C
20,00%
160°C
15,00%
170°C
10,00%
5,00%
0,00%
Gain
on
Gain
on
Gain
on
Gain
on
Gain
on
Gain
on
Gain
on
Masse
Masse
Masse
Masse
Masse
Masse
Masse
A3T
1W
2W
5W
10W
15W
20W
After 20 washings with obtain 10% on gain on masse for the sample treated three times at 170°C.
III.1.2: Cotton Gain on Masse of cotton samples after first, second and third treatment
Cotton
T
T°
of
Treatment
A
B
C
1
2
3
4
5
D
E
F
6
7
8
9
150°
150°
150°
150°
150°
150°
150°
150°
160°
160°
160°
160°
160°
160°
160°
Gain
on
Masse
A1T
9,59%
5,92%
4,43%
5,15%
4,84%
5,06%
4,51%
4,67%
8,11%
5,70%
6,92%
5,57%
4,72%
5,40%
5,05%
Gain
on
Masse
A2T
Gain
on
Masse
A3T
9,77%
11,10%
10,22%
10,17%
11,34%
12,43%
12,14%
11,26%
9,16%
17,50%
19,38%
18
18,35%
Yohann
Lachette
Application
of
Cyclodextrin
on
Textile
for
Cosmetic
Purpose
10
G
H
I
11
12
13
14
15
160°
170°
170°
170°
170°
170°
170°
170°
170°
6,81%
9,71%
7,29%
7,25%
7,37%
6,79%
7,04%
6,81%
6,82%
14,79%
20,51%
15,63%
15,28%
17,20%
11,15%
13,44%
19,17%
20,85%
Gain on Masse of cotton samples after 20 washing. Cotton
W
4
5
9
12
1
2
T°
of
Treatment
150°
150°
160°
160°
170°
170°
Gain
on
Gain
on
Gain
on
Gain
on
Gain
on
Gain
on
Masse
1W
Masse
2W
Masse
5W
Masse
10W
Masse
15W
Masse
20W
16,67%
14,64%
10,46%
7,76%
3,30%
0,82%
17,14%
15,24%
11,35%
8,16%
4,26%
1,53%
16,03%
14,97%
10,99%
8,05%
4,40%
1,73%
18,39%
16,79%
12,59%
9,94%
5,16%
1,97%
17,06%
16,56%
12,36%
9,56%
4,93%
1,78%
18,75%
16,91%
12,74%
10,09%
5,37%
2,05%
Even after 20 washings some particles stay on materials.
Treatment Gain of Masse 25,00%
20,00%
15,00%
150°C
160°C
10,00%
170°C
5,00%
0,00%
Gain
on
Masse
A1T
Gain
on
Masse
A2T
19
Gain
on
Masse
A3T
The gain on masse is linear and the highest temperature has the best results.
Yohann
Lachette
Application
of
Cyclodextrin
on
Textile
for
Cosmetic
Purpose
Washing Gain on Masse 25,00%
20,00%
15,00%
150°C
10,00%
160°C
170°C
5,00%
0,00%
Gain
on
Gain
on
Gain
on
Gain
on
Gain
on
Masse
A3T
Masse
1W
Masse
2W
Masse
5W
Masse
10W
Gain
on
Masse
15W
Gain
on
Masse
20W
III.1.3: Viscose Gain on Masse of viscose samples after first, second and third treatment
Viscose
T
T°
of
Treatment
A
B
C
1
2
3
4
5
D
E
F
6
7
8
9
150°
150°
150°
150°
150°
150°
150°
150°
160°
160°
160°
160°
160°
160°
160°
Gain
on
Masse
A1T
5,85%
6,34%
7,93%
7,14%
6,87%
6,85%
7,71%
6,96%
9,98%
9,91%
10,31%
8,57%
9,72%
10,67%
8,95%
Gain
on
Masse
A2T
Gain
on
Masse
A3T
11,34%
11,50%
11,22%
12,57%
11,08%
16,83%
17,54%
17,96%
17,49%
20,03%
19,09%
20
26,38%
Yohann
Lachette
Application
of
Cyclodextrin
on
Textile
for
Cosmetic
Purpose
10
G
H
I
11
12
13
14
15
160°
170°
170°
170°
170°
170°
170°
170°
170°
9,41%
9,71%
9,59%
10,27%
9,67%
11,19%
10,14%
9,90%
10,82%
18,79%
26,92%
18,65%
18,27%
17,90%
19,15%
20,44%
27,00%
27,85%
After three treatments the materials begin has to degrader. Gain on Masse of viscose samples after 20 washings. Viscose
W
4
5
9
12
1
2
T°
of
Treatment
150°
150°
160°
160°
170°
170°
Gain
on
Gain
on
Gain
on
Gain
on
Gain
on
Gain
on
Masse
1W
Masse
2W
Masse
5W
Masse
10W
Masse
15W
Masse
20W
18,67%
16,62%
12,46%
8,73%
4,90%
1,05%
17,17%
15,21%
12,35%
8,56%
4,64%
0,93%
24,03%
21,97%
16,99%
12,04%
6,24%
2,05%
23,98%
20,79%
16,59%
12,34%
7,02%
2,54%
25,06%
22,56%
18,36%
13,98%
8,54%
3,56%
25,75%
22,91%
17,94%
13,27%
8,78%
3,75%
Treatment Gain on Masse 30,00%
25,00%
20,00%
150°C
15,00%
160°C
170°C
10,00%
5,00%
0,00%
Gain
on
Masse
A1T
Gain
on
Masse
A2T
Gain
on
Masse
A3T
21
Yohann
Lachette
Application
of
Cyclodextrin
on
Textile
for
Cosmetic
Purpose
Washing Gain on Masse 30,00%
25,00%
20,00%
15,00%
150°C
10,00%
160°C
170°C
5,00%
0,00%
Gain
on
Gain
on
Gain
on
Gain
on
Gain
on
Masse
A3T
Masse
1W
Masse
2W
Masse
5W
Masse
10W
Gain
on
Masse
15W
Gain
on
Masse
20W
After 20 washings the sample treated at 150°C was near to 0% on gain on masse.
III.1.4: Discussion about results These results can show: -The temperature influence on the gain on masse, higher the temperature higher amount of β-CD attached to the material is obtained. -The gain on masse for treatment or washing is linear. -My idea about the third treatment is good, the gain on masse increase, nearly 50% for the polyester at 170°C. -The washing resistance is good even with third treatment. Even after 20 washings we have β-CD on sample. -The materials influence only for the treatment gain on masse, polyester is the best materials for application of β-CD. For the washing every material has the same results. 22
Yohann
Lachette
Application
of
Cyclodextrin
on
Textile
for
Cosmetic
Purpose
III.2: Vanillin UV/VIS spectra of solutions with treated cotton fabric with vanillin
23
(after 24h; after 48h)
Yohann
Lachette
Application
of
Cyclodextrin
on
Textile
for
Cosmetic
Purpose
UV/VIS spectra of solutions with treated polyester fabric with vanillin
(after 24h; after 48h)
UV/VIS spectra of solutions with treated viscose fabric with vanillin
(after 24h; after 48h)
24
The best results for all types of fabrics were obtained with the highest treatment at 170°C as is shoved on all graphs.
Yohann
Lachette
Application
of
Cyclodextrin
on
Textile
for
Cosmetic
Purpose
After 24 hours some particles leaved the material but after 48 hours more particles leave.
Conclusion I didn’t meet problem during my research maybe a lake of time, because the samples must stayed 4 hours in oven for the gain on masse. This lake of time influences the other part of my research that I can’t finish as I wish. I think one month more can be really better for this training period. This training period improved my knowledge about textile and cosmetic. I discovered how to make cosmetotextile like perfume textile.
25
Yohann
Lachette
Application
of
Cyclodextrin
on
Textile
for
Cosmetic
Purpose
Bibliographies -
Journal of Applied Polymer Science
-
http://www.wikipedia.com
-
http://www.timelines.ws/countries/SLOVENIA.php
-
http://www.institutfrance.si/fr/science-en-slovenie.php
26
Yohann
Lachette
