US2795477A - Coloration of fibres having a polyvinyl derivative base - Google Patents

Coloration of fibres having a polyvinyl derivative base Download PDF

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Publication number
US2795477A
US2795477A US438320A US43832054A US2795477A US 2795477 A US2795477 A US 2795477A US 438320 A US438320 A US 438320A US 43832054 A US43832054 A US 43832054A US 2795477 A US2795477 A US 2795477A
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Prior art keywords
fibres
coloration
anthraquinone
polyvinyl
shades
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US438320A
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Ratchewski Rachel
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Compagnie Francaise des Matieres Colorantes SARL
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Compagnie Francaise des Matieres Colorantes SARL
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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
    • C09B1/16—Amino-anthraquinones
    • C09B1/20—Preparation from starting materials already containing the anthracene nucleus
    • C09B1/26—Dyes with amino groups substituted by hydrocarbon radicals
    • C09B1/28—Dyes with amino groups substituted by hydrocarbon radicals substituted by alkyl, aralkyl or cyclo alkyl groups
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
    • Y10S8/92—Synthetic fiber dyeing

Definitions

  • the present invention concerns improvements in and relates to the coloration of fibres having a polyvinyl derivative base such as for example, those which are constituted by drawn polyvinyl chloride and which are known on the market under the names Rhovyl and Thermovyl.
  • n is an integer and in which R is an alkyl radical containing less than four carbon atoms. This group is preferably in the a-position.
  • a process for the coloration of fibres having a polyvinyl derivative base comprises applying thereto at least one anthraquinone dyestuif containing at least one group of the following formula:
  • n is an integer and in which R represents an quent esterification of the free alcoholic -OH group by means of formic acid, acetic acid or propionic acid.
  • dyestufis may be applied to the polyvinyl fibres by means of already known general methods, such as, for example, those described in French Patents No. 1,007,911 of April 14, 1948 and No. 1,009,215 of May 27, 1948.
  • the dyestuffs give bright shades of good fastness and may be applied alone or mixed with other derivatives of anthraquinone which, in themselves have only a slight aflinity for polyvinyl fibres, but which yield thereon rich shades when they are used in admixture with the above mentioned dyestuffs.
  • the dyestuffs of the present invention dye polyvinyl fibres in shades, varying from yellowish-red to bluegreen, which are very fast to water and to light.
  • Example 10 100 parts of Rhovyl fabric or yarn are introduced into a bath containing parts of acetoxymethylaminoanthraquinone containing of pure dyestutf, 750 parts of Patented June 11, 1957 water and 8 parts of a mixture of p-chlortoluene and the product of condensation of ethylene oxide on lauryl alcohol.
  • the initial temperature of the bath which is from 20-25 C. is raised to 4042 C. within a period of 20 minutes. It is kept at this temperature for half an hour. Rinsing is then effected in tepid water, then in cold water and the yarn or fabric is dried below 40 C.
  • the Rhovyl is dyed in bright, fast shades.
  • Example 2 The same dyestutf as in the previous example dyes Thermovyl in the presence of 2 grs. per litre of a condensation product of ethylene oxide and lauryl alcohol. The goods are steeped in a bath at 50 C. The temperature is raised to -95 C. and kept for an hour and a half at that level. The goods are rinsed in water and dried. The Thermovyl is dyed in clear yellowish-red shades which are very fast to light.
  • Example 7 1 methylamino 4 acetoxyethylamino 5:8 dihydroxyanthraquinone also give bluish-green shades on Rhovyl and on Thermovyl under the conditions stated above.
  • Example8 100 parts of Rhovyl fabric are introduced into a bath containing 5 parts of the dyestufi of the following formula:
  • the initial temperature of the bath which is from 2025 C. is raised to 4042 C. within a period of 20 minutes. This temperature is maintained for half an hour. Rinsing is first effected in tepid Water, then in cold water and the fabric is dried below 40 C. The Rhovyl fabric is dyed in beautiful yellowish-red shades.
  • the anthraquinone dyestuff used above is obtained by acetylation, in the presence of pyridine, of the condensation product obtained by the action of monohydroxyethyl-hydroxyethylamine on a-chloroanthraquinone, in the presence of pyridine and copper acetate at the boil.
  • the dyestufi may be obtained by acetylation, in the presence of pyridine, of 1-methylamino-4-(monohydroxyethyl-hydroxyethyl)amino-anthraquinone.

Description

United States Patent COLORATION OF FIBRES HAVING A POLYVINYL DERIVATIVE BASE Rachel Ratchewski, Paris, France, assignor to Compagnie Francaise des Matieres Colorantes, Paris, France, a company of France No Drawing. Application June 21, 1954, Serial No. 438,320
Claims priority, application France June 24, 1953 4 Claims. (Cl. 8-25) The present invention concerns improvements in and relates to the coloration of fibres having a polyvinyl derivative base such as for example, those which are constituted by drawn polyvinyl chloride and which are known on the market under the names Rhovyl and Thermovyl.
It has been found that these fibres may be dyed in a satisfactory manner by means of anthraquinone derivatives containing a group of the following formula:
in which n is an integer and in which R is an alkyl radical containing less than four carbon atoms. This group is preferably in the a-position.
According to the present invention therefore a process for the coloration of fibres having a polyvinyl derivative base is provided which comprises applying thereto at least one anthraquinone dyestuif containing at least one group of the following formula:
in which n is an integer and in which R represents an quent esterification of the free alcoholic -OH group by means of formic acid, acetic acid or propionic acid.
These dyestufis may be applied to the polyvinyl fibres by means of already known general methods, such as, for example, those described in French Patents No. 1,007,911 of April 14, 1948 and No. 1,009,215 of May 27, 1948. The dyestuffs give bright shades of good fastness and may be applied alone or mixed with other derivatives of anthraquinone which, in themselves have only a slight aflinity for polyvinyl fibres, but which yield thereon rich shades when they are used in admixture with the above mentioned dyestuffs.
The dyestuffs of the present invention dye polyvinyl fibres in shades, varying from yellowish-red to bluegreen, which are very fast to water and to light.
The invention will be more clearly understood by reference to the following examples which are purely illustrative and in which the parts given are parts by weight.
Example] 100 parts of Rhovyl fabric or yarn are introduced into a bath containing parts of acetoxymethylaminoanthraquinone containing of pure dyestutf, 750 parts of Patented June 11, 1957 water and 8 parts of a mixture of p-chlortoluene and the product of condensation of ethylene oxide on lauryl alcohol. The initial temperature of the bath which is from 20-25 C. is raised to 4042 C. within a period of 20 minutes. It is kept at this temperature for half an hour. Rinsing is then effected in tepid water, then in cold water and the yarn or fabric is dried below 40 C. The Rhovyl is dyed in bright, fast shades.
Example 2 The same dyestutf as in the previous example dyes Thermovyl in the presence of 2 grs. per litre of a condensation product of ethylene oxide and lauryl alcohol. The goods are steeped in a bath at 50 C. The temperature is raised to -95 C. and kept for an hour and a half at that level. The goods are rinsed in water and dried. The Thermovyl is dyed in clear yellowish-red shades which are very fast to light.
Example3 The dyestuif having the following formula:
NH-CHa NH-CHz-CE-O-O o-ora under conditions similar to those in the previous examples, yields blue shades on Rhovyl and on Thermovyl.
Example 4 If, under the same conditions as in the preceding examples, there is used a mixture of the dyestuffs of the formulae:
(1) ITHCH3 NH-CH2CH2O-C o-om (II) IIIH-OH:
NH-CHa Example 5 The dyestuif formed by 1-methylamino-2-bromo-4- acetoxyethylamino-anthraquinone dyes the polyvinyl fibres by the processes given above in reddish-blue shades.
Example 6 With 1-methylamino-4-acetoxyethylamino-6chloro-anthraquinone of the formula:
NHCH2CH2-O-C O-GHs under the same conditions as in the preceding examples, greenish-blue shades are obtained.
Example 7 1 methylamino 4 acetoxyethylamino 5:8 dihydroxyanthraquinone also give bluish-green shades on Rhovyl and on Thermovyl under the conditions stated above. I A
Example8 100 parts of Rhovyl fabric are introduced into a bath containing 5 parts of the dyestufi of the following formula:
with 20% of pure dyestuif, 750 parts of water and 8 parts of a mixture of p-chlortoluene and the product of condensation of ethylene oxide on lauryl alcohol.
The initial temperature of the bath which is from 2025 C. is raised to 4042 C. within a period of 20 minutes. This temperature is maintained for half an hour. Rinsing is first effected in tepid Water, then in cold water and the fabric is dried below 40 C. The Rhovyl fabric is dyed in beautiful yellowish-red shades.
The anthraquinone dyestuff used above is obtained by acetylation, in the presence of pyridine, of the condensation product obtained by the action of monohydroxyethyl-hydroxyethylamine on a-chloroanthraquinone, in the presence of pyridine and copper acetate at the boil.
Example 9 The dyestufi of the following formula:
NH-UHa NH-GHrCHa-O-CHrQHrO-COCH3 yields, under conditions similar to those in Example 8, greenish-blue shades on Rhovyl or Thermovyl.
The dyestufi may be obtained by acetylation, in the presence of pyridine, of 1-methylamino-4-(monohydroxyethyl-hydroxyethyl)amino-anthraquinone.
Iclaim: K 1. Process for the colouration of polymerised vinyl chloride textile fibres which comprises applying thereto at least the anthraquinone' dyestuif of the following formula:
2. Process as claimed in claim 1 in which the anthraquinone dyestuff is used in admixture with another anthraquinone derivative.
3. Polymerised vinyl chloride textile fibres coloured by means of the anthraquinone dyestuff of the following formula:
2,359,735 -Kienle Oct. 10, 1944 Q FOREIGN PATENTS 506,253 Great Britain May 19, 1939 923,188 France Feb. 17, 1947 259,411 Switzerland June 16, 1949 OTHER REFERENCES American Dyestuif Reporter for April 21, 1947, pages 189, 190.
Rayon Textile Monthly for September 1944, page 119 (457).
American Dyestuff Reporter for May 21, 1945, page P213.

Claims (1)

1. PROCESS FOR THE COLOURATION OF POLYMERISED VINYL CHLORIDE TEXTILE FIBRES WHICH COMPRISES APPLYING THERETO AT LEAST THE ANTHRAQUINONE DYESTUFF OF THE FOLLOWING FORMULA:
US438320A 1953-06-24 1954-06-21 Coloration of fibres having a polyvinyl derivative base Expired - Lifetime US2795477A (en)

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DE (1) DE1012284B (en)
FR (1) FR1085424A (en)
GB (1) GB765356A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3092435A (en) * 1959-05-11 1963-06-04 Acna Process of dyeing polyethylene and polypropylene materials

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2930003A1 (en) * 1978-07-26 1980-02-07 Ciba Geigy Ag NEW ANTHRACHINONE CONNECTIONS

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB506253A (en) * 1937-10-19 1939-05-19 Henry Dreyfus Improvements in or relating to the colouration of materials made of or containing cellulose derivatives
US2359735A (en) * 1939-12-16 1944-10-10 American Cyanamid Co Dyeing of polyvinyl halide-acetate copolymer fibers and fabrics
FR923188A (en) * 1946-01-23 1947-06-30 Rhodiaceta Process for coloring polyvinyl derivatives
CH259411A (en) * 1945-12-27 1949-01-31 Rhodiaceta Stable dye bath for objects or articles based on polyvinyl derivatives.

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE618006C (en) * 1933-09-03 1935-08-30 I G Farbenindustrie Akt Ges Process for coloring plastic masses from water-insoluble polymerization products of unsaturated compounds with an olefinic double bond
US2381971A (en) * 1937-10-19 1945-08-14 Celanese Corp Anthraquinone dyestuffs
US2338908A (en) * 1939-11-25 1944-01-11 Eastman Kodak Co Anthraquinone compounds and material colored therewith
US2411148A (en) * 1943-10-23 1946-11-19 Eastman Kodak Co Anthraquinone dyestuffs

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB506253A (en) * 1937-10-19 1939-05-19 Henry Dreyfus Improvements in or relating to the colouration of materials made of or containing cellulose derivatives
US2359735A (en) * 1939-12-16 1944-10-10 American Cyanamid Co Dyeing of polyvinyl halide-acetate copolymer fibers and fabrics
CH259411A (en) * 1945-12-27 1949-01-31 Rhodiaceta Stable dye bath for objects or articles based on polyvinyl derivatives.
FR923188A (en) * 1946-01-23 1947-06-30 Rhodiaceta Process for coloring polyvinyl derivatives

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3092435A (en) * 1959-05-11 1963-06-04 Acna Process of dyeing polyethylene and polypropylene materials

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DE1012284B (en) 1957-07-18
GB765356A (en) 1957-01-09
FR1085424A (en) 1955-02-02

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