DE1469683A1 - New Disazo dyes and their use for dyeing synthetic fibers - Google Patents

Description

"New Disazo Dyes and Their Use for Coloring

synthetic fibers "

Inventor:

Marcel Jirou
Jean Leroy

The present invention, made in the service of Francaise des Matie'res Colorantea SA, relates to new dyes which are adapted for coloring synthetic fibers and in particular polyester and cellulose triacetate fibers, in bright shades ranging from yellow to brownish-red are sufficient. In addition to excellent Lichtechtheitseigensohaftten these dyes are exceptionally fes ^a

809813/1194

versus sublimation. The problem of the non-fastness property is ic general in the case of pile / ester fibers through which Use of dyes of the -Anthraquinone series, dissolved. However, this range is limited to the range of yellow and orange hues.

The Sublimierungaprobleni has one, for the coloring of the Polyester and cellulose triacetate fibers, original meaning, due to the high temperatures, v / elchen them Fibers are subjected. Especially at the time of heat setting 13t äjsjk sublimating dye leans up knock down cold parts of the apparatus.

It has now been found, according to the present invention, that dyes of the general formula:

CH ₂ CH ₂ CN

N = N - Ar - N = W - / V N

) ^X CH ₂ CH ₂ CS

in which X is a hydrogen or chlorine atom or a

CH -, - or OCH, group, Ar is a benzene or naphthalene kera represents and the cores A and Ar optionally through Halogen atoms or CH -, -, OCH, - or OCpHj - groups substituted have excellent affinity and make it possible to obtain strong yellow to brown-red shades with very high lightfastness properties', sublimation, discoloration, washing, sea water, sweat, burning

BATH ORIGINAL. -. 3 -809813/1194

gas, heat setting and pleating.

The dyes can be produced by synthesis, for example by coupling an aminobenzene, ..- / eiches is optionally substituted by diethyl omega sulfoderivat another aminobenzene or an optionally substituted alpha-amino-naphthalene, saponification of the obtained Honoazo compound, diazotization and coupling in an acidic environment, with or without neutralization with a dicyanoethyl derivative the formula

I ₂ CH ₂ CH

3 _O CH ₀ ClJ
a 2 2

in which X is a hydrogen or chlorine atom or a Represents CH_ or OCH, group.

Aniline, chloroaniline, bromaniline, toluidine, anisidine, etc. can be used as the first component, Chlorotoluidines, dichloroanilines, xylidines; to form the Intermediate one can use aniline, ortho- or meta-toluidine, ortho- or meta-anisidine, meta-chloroaniline, Paraxy lidine, aminohydroquinone dimethyl or diethyl ether, 2,5-dimethyl-aniline and other analogous bases; dicyanoethyl-aniline, meta-toluidine, Use meta-anieidin or meta-chloroaniline.

The coloring is carried out according to known methods, for example 809813/1194

below 10O ⁰ C with carrier substances or above 100 ⁰ G with pressure.

Compared to diaazo dyes of neighboring structure which carry one or two hydroxyethyl groups the dyes according to the invention have significantly greater lightfastness properties.

When measuring the authenticity property with the fadeometer the dye was on polyester fiber

H = N - ( VN = N - ( VN

CH ₂ CH ₂ OH

1 to 2, while this dye with "the same color value."

CH ₂ CH ₂ CN

CH ₂ CH ₂ CN

5 to 6 has.

The dye of the formula

C ₂ H ₅

^V CH ₂ CH ₂ CN

and its use for coloring cellulose acetate has already been described. But this dye has only one very poor affinity and one for this fiber

Q0O010 / 1 10 /

sohigh lightfastness property. It was therefore not foreseeable that the dyes according to the invention could be used on polyester fibers, which once marked lightfastness property, such as an autograph » have a good affinity and are very strong against sublimation. Several patents mention the use of the Ethyl-diqjiBno derivatives of aniline and its homologues, but none of the inside mentions the production of disazo products) it is precisely these latter that form after the Invention an advance, due to their better resistance to sublimation

The following examples explain the scope of the invention without restricting it · The specified parts are Öewiohtteilr »

Example t

19 »8 parts of 4-A * ino-azobenzene are put into 40 files of 20 ° Bl Hydrochloric acid made into a paste, diluted and diazotized for 2 hours "with the aid" of a Hatriue nitrite solution. on the other hand 22 parts · Il-Moyanoäthyl-meta-toluidin Bit 50 parts Ethyl alcohol dissolved and poured into the diazo solution · The The dye obtained is filtered and washed after stirring for several hours. The paate becomes a diapergiver * » medium added, for example dinaphthylmethane natriu »» disulfonate, dried and triturated · The dye obtained dyes polyester or oleulose triacetate fibers in orange-yellow shades "

809813/119 * bad

The following table gives further examples:

first partner

int ermedier partner

End partner

Hue.

2 aniline

aniline

3 4-chloro-2-meta-anisidine ethyl-ainino-benzene

4 ortho-bromoaniline meta-toluidine

5 para - anisidine aniline

6 meta-chloroaniline meta-anisidine

7 aniline alpha-liaphthylamine

6 2,4-dichloro-aniline meta-anisidine

S aniline aminohydroquinone

dimethyl ether

10 2,5-dichloro-aniline meta-toluidine

11 aniline meta-gliloraiiiline

12 para-chloroaniline para-creaidin

13 2,4-xylidine meta-toluidine

14 ortho-toluidine ortho-toluidine

15 aniline aniline

16orfcho-chloroaniline meta-chloroaniline

17 meta-2oluidine meta-anisidine

18 aniline aniline

19 ortho-chloroaniline meta-anisidine '

20 ortho-toluidine ortho-toluidine

Ij W-Di cyan ο-.r.thyl-aniline

dito

dito

yellowish reddish

orange-yellow

orange-yellow

ditto orange-yellow

ditto orange-yellow

Hi-DicyanOcLtliyl-rotmeta-toluidine brownish

αϊτό orange orange orange dito Red-
brown i Orange red orange-yellow- dito orange NN-dicyanoethyl- yellow-
meta-chloroaniline reddish. dito orange-yellow dito dito Orange red dito dito Orange red dito orange HN-Eicyano-ethyl- orange-
meta-anisidine red dito dit ρ

example

A printing paste is produced which consists of the following V

Components is composed: ■.,

Dye of Example 15 10, Part © ,,;

Sodium Dinaphthyl Methane Disulfonate H parts

- 7-809813/1 194; BADORfQiNAL

Mono-ethyl-compartment of ethylene-gl / kol 50 parts

V.'asser 500 parts

./. aqueous solution of sodium fluorate '"· 30 parts

Thickener 600 parts

This paste is applied by means of a grooved roller to a layer of polyester fibers which has previously been de-glued by alkaline washing under heat. It fixes the color by steam treatment under pressure at 130 to 14O ⁰ C. It is rinsed and treated with heat by means of a reducing alkaline bath, v / hich 1 to 2 g / l of a ilkylphenol-Äthyleiiox / d condensate contained. The fabric is dyed in an orange-red shade with excellent fastness properties, the exposed parts remaining white.

Example 22

A foul-etching bath is produced which is composed of the following components:

Dye of Example 6 30 parts

Sodium dinaphthyl methane disulfonate 7 parts

Thickener 5 parts

Water 58 parts

A polyester fabric strip is padded several times in this dispersion and heat-set ^{at 20O 0 C for 1 minute.} The dye, which was very strong against sublimation, remains on the fiber and does not migrate to the cold parts of the apparatus.

80 9813/1 194

Claims (3)

-s- U69683 patent application 1. Disazo dyes characterized by the general Formula: . . CH ₀ CH ₀ CH ( A VH = K-Ar - H = H - / V-iV r \ π it πττ rcTj in ./elcher X is a hydrogen or chlorine atom or a CH, -, or OCH, group, Ar is a benzene or Iaphthalene nucleus and the nuclei A and Ar are optionally by halogen atony or by CH ₅ -, OCH ₅ - or OC ₂ Hj groups are substituted. 2. Use of the dyes explained in claim 1 characterized in that they are used for coloring and printing synthetic fibers, especially polyester or Cellulose triacetate fibers can be used. 3. Synthetic fibers, provided they are made with the help of the below Claim 1 explained dyes were colored. 809813/119 Λ