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Experiments in Dyes and Dyeing Means to Better Understand the Nature of Intermolecular Forces Mordechai Livneh*

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Experiments in Dyes and Dyeing Means to Better Understand the Nature of Intermolecular Forces Mordechai Livneh* DE ANIVERSARIO Experiments in Dyes and Dyeing Means to better understand the nature of intermolecular forces Mordechai Livneh* Abstract are: Cellulose esters (cotton derivatives), Polyamides (Nylon The nature of intermolecular forces is responsible for a vast 6,6, Nylon 6 etc), Acrylics (Orlon) and Polyesters (Dacron, number of phenomena in our everyday life. It can explain Terylene etc.). The chemical structures of these six fiber types for example, trends in solubility, differences in boiling are shown in Figure 1. points, adsorption effects (chromatography) and many other observations. A Cellulose unit 1 Our teaching experience shows that it is not easy to CH OR 2 2 OR O 3 explain this issue to students of all levels, but better under- O RO O 2 O RO standing can be achieved through experimentation. One of 3 O RO 1 the most effective practical experiences we offer our students ROH2C at BIU or in high schools deals with dyeing fibers with Cellulose ester Diacetate (Acetate) Cellulose ester Triacetate Cotton (Cellulose) O O synthetic or natural dyes. We supply our students with pieces 1 2 3 1 2 OCCH 1 2 3 of cloth comprised of several different kinds of fibers (“mul- R = R = R = H R = R = 3 R = R = R = OCCH3 R3 = H tifiber”). They also receive a series of dyes (in the University ''' O R' O R O R some of the dyes are synthesized by the students). We then H H H H H H N C C N C C N C let them be involved in the process of dyeing. Immediately, C C N C C N C C N C H H H H (CH ) '' one can notice that certain fibers bind some dyes better than O 2 2 O R H O CH2 O others. Discussions and results’ sheets follow the experimen- COO hydrogen bond S ionic cross link a disulfide cross link tal work and a better understanding of the nature of the NH S 3 O '' intermolecular forces involved is achieved. (CH2)4 O R CH2 O H H H H H Besides showing the connection of the dyeing results to N C C N C C N C C C N C C N C C N intermolecular forces, such a workshop on dyes and dyeing, H H H H H H ''' gives also its’ participants an opportunity to focus on issues O R O R' O which are not dealt with, in the main curriculum in Chemis - WOOL try. These include: the history of dyes and dyeing; natural R, R', R'', R''', etc. = any one of the natural amino acids dyes vs. synthetic dyes; chemical nature of dyes; do we approxi mately 30% g lutamic aci d and cystine synthesize dyes or extract them from natural sources? and OO OO differences between dyes for fabrics and other kinds of H N(CH) NH C (CH ) CNH(CH) NH C (CH ) COH coloring materials (food dyes, hair colors, paints, etc). 2 2 6 2 4 2 6 2 4 n In this article we present four dyeing experiments. For NYLON 6,6 each experiment we specify its context to the curriculum and (a polyamide) to which grades it is appropriate. All the experiments use only milligrams of dyes and can be performed personally or OOO O in “stations”. HOC C O CH2CH2 OC COCH2CH2OH INTRODUCTION Classification of fibers POLYESTER (DACRON) In general, fibers can be either natural or synthetic. The two R R = H, CH3, Cl natural fibers that are most used and famous are wool and (CH2 CH)x (CH2 C)y R' = -COOCH , -OCOCH , etc. cotton. The most common synthetic fibers used in clothing CN R' 3 3 n ACRYLIC (x > 85% , y < 15%) (ORLON) (sometimes contains sulfonic groups) *Department of Chemistry, Bar Ilan University, Ramat-Gan, ISRAEL, 52900. E-mail: [email protected] Figure. 1 The six main fibers. 534 Educación Química 16[4] DE ANIVERSARIO H3C CH3 Dyes N As with fibers, dyes can also be either natural or synthetic. O NH2 Both types though are organic molecules with specific func- SO 3Na COOH OH Br Br NaO3S C tional groups that act as chromophors. The fiber dyes are O HN NaO O O N(CH3)2 characterized by three major criteria: Br Br Acid Blue 25 Acid R ed 87 (Eosin Y) 1) According to their solubility in water. Many dyes are ionic SO3Na organic hydrophilic compounds, which dissolve well in Acid Green 50 water to form clear aqueous solutions. Other dyes are Acid dyes. hydrophobic with low water solubility. These dyes tend to form dispersions when introduced into water. Envi- SO3 Na Direct red 81 NaO3SNNNN ronmental restrictions dictate that in the instructional HO laboratories we should work only with water based dyes. 2) According to their chemical nature or the way they are applied to the fiber. This classification is the most used by industry NH dyers, and many “commercial” names of dyes are given O according to this classification. For example: Acid red NH2 OH OH NH2 Direct blue 1 NaO3S NN NN SO3 Na 87, Disperse yellow 3 etc. Thus we can find the following common types of dyes: CH3 OOCH3 SO Na SO Na 1. Acid dyes – These are anionic organic compounds 3 3 that are applied to the fiber from acidic solutions. SO3 H SO3 H Acid dyes are mostly used for dyeing natural and O2 N synthetic polyamides (wool and nylon). The acid N N Direct yellow 11 NO2 dyes that we use in our experiments are the follo- HO3S wing ones: Acid blue 25, Acid red 87, Acid green HO3S 50 and Acid violet 49. The term “acid” means that Direct dyes. the dyeing process is done in an acidic solution. H 3C CH3 2. Direct dyes – These are anionic dyes having a good N H3C CH3 Cl N Cl affinity (substantivity) for cellulose fiber. These COOCH2CH3 dyes are normally applied from aqueous dye baths H 3C CH3 Cl C (sometimes containing also an electrolyte). Here CH3CH2NH O NHCH2CH3 C are the structures of three direct dyes that are used (CH3) 2N N(CH3)2 N(CH ) in our experiments. 3 2 Basic Violet 3 Basic Red 1 Basic Green 4 3. Basic dyes – Organic ammonium salts. Are applied (Crystal violet) (Rhodamine 6G) (Malachite green) to the fiber either directly from w ater solutions or from acid solutions. Basic dyes are substantive to Basic dyes. silk but used a lot in dyeing acrylic fibers. The three CH3 following basic dyes we use in our experiments are: O 4. Disperse dyes – These neutral organic compounds which have low water solubility, were developed H3C C NH NN for dyeing acetate rayon. In the past they had a small market but with the rising of the synthetics HO after World War II, they became very important. Disperse yellow 3. In our experiments disperse yellow 3 is used. 5. Vat dyes – These are ancient dyes, insoluble in known vat dye is INDIGO (see later). water, that on reduction (with sodium hydrosulfite) 6. Azoic dyes – Organic compounds that contain (as form compounds that are soluble in basic solu- other dyes from other groups), the azo (—N=N—) tions. When cotton or other fiber is immersed in functional group. The synthesis of the dye can be done such solutions it absorbs the reduced dyestuff, directly in the fiber by mixing the two components which, on exposure to air, is oxidized; thus forming that form the azo group. Mostly used with cotton. again the original insoluble compound which is 7. Reactive dyes – These are the most recent developed trapped now within the fiber itself. The most dyes. Dye molecules react with the functional Octubre de 2005 535 DE ANIVERSARIO groups of the fiber to forming thus a chemical bond (for example, an esteric bond with cotton). 3) According to the functional group responsible for the color. The interactions between the fiber and the dye In order to get the desired color, the dye molecules should have strong affinity to the fiber (called also substantivity to the fiber). This affinity is based mostly on intermolecular forces such as: ionic bonds, hydrogen bonds van-der-Waals bonds, and covalent bonds (only in the case of reactive dyes). Experimental Materials: The fibers we use in most cases are the six major types mentioned before: (wool, cotton, etc). These are squared pieces, ca. 5 × 5 cm, of each individual type, or multifibers (6, 8 or 12) in which the six major fibers (or more) Figure 2. Multifiber 6 used in the dyeing experiments. are weaved together on one 5 × 5 cm piece (see figure 2). The dyes are organic synthetic compounds, which are read- ily available from many sources. We purchase both, fibers and dyes, from Testfabrics(*). Experiment # 1 – Dyeing with Acid dyes The recommended method of the dyeing activity is to The purpose of the experiment (and how it can be related to the use “stations”. Each station is dedicated to one type of dyes. curriculum) Acid dyes are used in Station # 1, direct dyes in station # 2, and This experiment can be associated with the subject of inter- so on. In the stations 25-50 mL beakers are used. Alterna- molecular forces. It emphasizes the trend of ionic materials tively each student (or a couple of students) can get a small (dyes) to be attracted to ionic substrates (protonated fibers). vial of each of the dyeing baths (**). It is recommended to The experiment also relates to polymers (fibers) and some prepare the dyeing baths before the actual lab.
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