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Directives on the restrictions of Azo Dyes 2002/61/EC & 2003/3/EC – EU Directives relating to restrictions on the marketing and use of certain dangerous substances and preparations (azocolourants and ‘blue colorant’)

 

Summary of the Directives:

Limit

2002/61/EC (aromatic amines)                    30 mg/kg 

2003/3/EC (2 blue colorants)                      1000 mg/kg

 

Azo dyes (see their definitions at the bottom of page) are among the oldest man-made chemicals and they are used in the textile, printing and the food industries. Some dyes and some of their N-substituted aromatic bio-transformation products are toxic and/or carcinogenic and therefore these dyes are considered to be hazardous.

Azo dyes which, by reductive cleavage of one or more azo groups, may release in detectable concentrations one or more of the aromatic amines listed in the Directive may not be used in textile and leather articles which may come into direct and prolonged contact with the human skin or oral cavity, including - 

(a) clothing, bedding, towels, hairpieces, wigs, hats, nappies and other sanitary items, sleeping bags;

(b) footwear, g
loves, wristwatch straps, handbags, purses or wallets, briefcases, chair covers, purses worn round the neck;

(c) textile or leather toys and toys which include textile or leather garments; and

(d) yarn and fabrics intended for use by the final consumer.

 

 

The Main Test Methods

 

EN 14362-1:  Detection and Determination of Certain Listed Aromatic Amines Derived from Azo Colorants

EN 14362-2:  Detection and Determination of Certain Listed Aromatic Amines Derived from Azo Colorants

 

In most cases, Gas Chromatographic Mass Spectrometry (GC-MS) / Thin Layer Chromatography (TLC) Technique are used for result determination.

 

 

List of the aromatic amines

 

 

AMINES TESTED

CAS NO.

 

 

 

1.

4-aminodiphenyl/xenylamine/

Biphenyl-4-ylamine

  92-67-1

2.

Benzidin

  92-87-5

3.

4-chlor-o-toluidine

  95-69-2

4.

2-naphthylamine

  91-59-8

5.

o-aminoazotoluene/

4-o-tolylazo-o-toluidine/

4-amino-2’,3-dimethylazobenzene

  97-56-3

6.

2-amino-4-nitrotoluol/5-nitro-o-toluidine

  99-55-8

7.

p-chloranilin/4-chloroaniline

106-47-8

8.

2,4-diaminoanisol/

4-methoxy-m-phenylenediamine

615-05-4

9.

4,4'-diaminodiphenylmethane/

4,4-methylenedianiline

101-77-9

10.

3,3'-dichlorobenzidine/

3,3’dichlorobiphenyl-4,4’-ylenediamine

  91-94-1

11.

3,3'-dimethoxybenzidine/o-dianisidine

119-90-4

12.

3,3'-dimethybenzidine/4,4’-bi-o-Toluidine

119-93-7

13.

3,3'-dimethyl-4,4'-diaminodipenylmethane/

4,4’-methylenedi-o-toluidine

838-88-0

14.

p-cresidin/6-methoxy-m-toluidine

120-71-8

15.

4,4'-methylen-bis-(2-chloro-aniline)/

2,2’-dichloro-4,4’methylene-dianiline

101-14-4

16.

4,4'-oxydianiline

101-80-4

17.

4,4'-thiodianiline

139-65-1

18.

o-toluidine/2-aminotoluene

  95-53-4

19.

2,4-toluylendiamin/

4-methyl-m-phenylenediamine

  95-80-7

20.

2,4,5-trimethylaniline

137-17-7

21.

4-aminoazobenzene

  60-09-3

22.

o-anisidine/ 2-methoxyaniline

  90-04-0

23.

2,4-Xylidin

  95-68-1

24.

2,6-Xylidin

  87-62-7

 

 

Remarks:

Azocolorants that are able to form 4-aminoazobenzene (CAS Nr:60-09-3), generate under the testing condition into aniline and 1,4-phenylenediamine. The detection of it can only be ascertained with the chemical structure of the colorant used.

 

The 2 ‘Blue Colourants’:

 

CAS number              Index number             EC number               

Not allocated             611-070-00-2             405-665-4                 

Component 1: CAS-No.: 118685-33-9; C39H23ClCrN7O12S.2Na
Component 2: C
46H30CrN10O20S2.3Na

 

The 2 ‘Blue Colourants’:

A mixture of:

disodium(6-(4-anisidino)-3-sulfonato-2-(3,5-dinitro-2-oxidophenylazo)-1-naphtholato)(1-(5-chloro-2-oxidophenylazo)-2-naphtholato)chromate(1-); and
trisodium bis(6-(4-anisidino)-3-sulfonato-2-(3,5-dinitro-2-oxidophenylazo)-1-naphtholato)chromate(1-)

 

 

Definition of Azo Compounds

 

Azo compounds are compounds bearing the functional group R-N=N-R', in which R and R' can be either aryl or alkyl. The N=N group is called an azo group, although the parent compound, HNNH, is called diimide. The more stable derivatives contain two aryl groups. The name azo comes from azote, an old French name of nitrogen that is derived from the Greek a (not) + zoe (to live).

 

As Dyes and Pigments

As a consequence of п-delocalization, aryl azo compounds have vivid colours, especially reds, oranges, and yellows. Therefore, they are used as dyes, "azo dyes." Some azo compounds, eg. methyl orange, are used as acid-base indicators due to the different colours of their acid and salt forms. The development of azo dyes was an important step in the development of the chemical industry. Azo pigments are colorless particles (typically earths or clays), which have been colored using an azo compound. Azo pigments are important in a variety of paints including artist's paints. They have excellent coloring properties, again mainly in the yellow to red range, as well as lightfastness. The lightfastness depends not only on the properties of the organic azo compound, but also on the way they have been adsorbed on the pigment carrier. Azo pigments are advantageous because they are non-toxic.

 

Aryl Azo Compounds

Aryl azo compounds are usually stable, crystalline species. Azobenzene is the prototypical aromatic azo compound. It exists mainly as the trans isomer, but upon photolysis, converts to the cis isomer. Aromatic azo compounds can be synthesized by using an azo coupling reaction, which entails an electrophilic substitution reaction where a aryl diazonium cation attacks another aryl ring, especially those substituted with electron-releasing groups.[1] Since diazonium salts are often unstable near room temperature, the azo coupling reactions are typically conducted near ice temperatures. The oxidation of hydrazines (R-NH-NH-R') also gives azo compound

 

Aliphatic Azo Compounds

Aliphatic azo compounds (R and/or R' = aliphatic) are less commonly encountered than the aryl azo compounds. One example is diethyldiazene, EtN=NEt.[3] At elevated temperatures or upon irradiation, the carbon-nitrogen (C-N) bonds in certain alkyl azo compounds cleave with the loss of nitrogen gas to generate radicals. Owing to this process, some aliphatic azo compounds are utilized as radical initiators. Representative is Azobisisobutylonitrile (AIBN) which is widely used as an initiator in polymerization. Because of their instability, especially for aliphatic ones, care should be taken with the handling of azo compounds or an explosion may occur.

 

 

 

 

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