Bioprocessing for Sustainable production of COLoured textiles

Final Project Meeting - Istanbul, July 11th, 2013

UNISI

Bioprocessing for Sustainable production of COLoured textiles

Strategies for the synthesis:

NH2

OH

COOH

Laccase, O2

O

NCOOH COOH

NH2

O

Natural process:

SOPHIED Project:

Enaud et al., 2010. Dyes and Pigments 85, 99-108.

LAR-1

Forte et al., 2010. Journal of Molecular Catalysis B: Enzymatic 63, 116-120.

Bioprocessing for Sustainable production of COLoured textiles

Industrial Dyes

Reactive red 24 Reactive blue 2

Direct red 28 Acid red 18

Dyes interactions with woollen fabrics:

(B)

(A)

Bioprocessing for Sustainable production of COLoured textiles

Scale-up of the Dyes

Precursors Dye

SO3H

NH2

H2N

15 g/L

47.2 g/L

35 g/L

Bioprocessing for Sustainable production of COLoured textiles

Dye name Precursors Light Fastness ISO 105 B02 (12 hour grade: 3)

Washing Fastness ISO 105 C06 A2S (40°C 30

minute)

SIAY1 4-nitro-1-naphthylamine and 4-amino-5-hydroxynaphthalene-2,7-disulfonic acid 4 5

4,5-dihydroxy-1,3-benzenedisulfonic acid - Dye depth is very low

5-amino-1-naphthalenesulfonic acid 3-4 4-5

Benzidine hydrochloride and N-(1-naphthyl)ethylenediamine 2-3 4

SIAR1 2,2′-Azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) diammonium salt and 4-amino-1-naphthalenesulfonic acid (molar ratio 1:20)

3 4-5

3-Methyl-2-benzothiazolinone hydrazone hydrochloride hydrate and 5-amino-1-naphthalensulfonic acid 2 3

3-Methyl-2-benzothiazolinone hydrazone hydrochloride hydrate and aniline-2-sulfonic acid 1-2 3-4

2,5-Diaminobenzenesulfonic acid and 3-aminobenzensulfonic acid 2 5

3-Methyl-2-benzothiazolinone hydrazone hydrochloride hydrate and 6-amino-4-hydroxynaphthalensulfonic acid 2-3 5

p-phenylendiamine, aniline hydrochloride and 3-aminobenzensulfonic acid 2-3 3-4

3-Methyl-2-benzothiazolinone hydrazone hydrochloride hydrate and Aniline hydrochloride 2-3 3-4

p-phenylendiamine and 5-amino-1-naphthalenesulfonic acid 2-3 4-5

SIAB1 3-Methyl-2-benzothiazolinone hydrazone hydrochloride hydrate and 4-Amino-5-hydroxynaphthalene-2,7-disulfonic acid monosodium salt hydrate (molar ratio 1:1)

4 4-5

3-Methyl-2-benzothiazolinone hydrazone hydrochloride hydrate and 4-4'-diaminostilbene - -

2,2′-Azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) diammonium salt and 3-(Dimethylamino)benzoic acid 1 4

Light fastness and Washing tests:

Bioprocessing for Sustainable production of COLoured textiles

SIAR1 SIAB1 SIAY1

40°C 60°C 80°C 96°C

Selected dyes for woollen fabrics:

Bioprocessing for Sustainable production of COLoured textiles

Daphnia magna Straus (Cladocera, Crustacea) inhibition test:

Dye EC50 (%) 48 h – UNI EN ISO 6341:1999

SIAY1 (pH 5) ∼2SIAB1 (pH 5) ∼10SIAR1 (pH 5) 49

SIARB1 (pH 3) 55Acid Yellow (Follone R) 28

Acid Blue Marine Dylan SB 15Acid Red Scarlet (Follone FG) 20

BISCOL dyes (minor/modereate toxicity)

Industrial dyes (minor/modereate toxicity)