US3785768A - Process for the dyeing of fibre material consisting of polyacrylonitrile or acrylonitrile-containing copolymers - Google Patents

Process for the dyeing of fibre material consisting of polyacrylonitrile or acrylonitrile-containing copolymers Download PDF

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US3785768A
US3785768A US00179571A US3785768DA US3785768A US 3785768 A US3785768 A US 3785768A US 00179571 A US00179571 A US 00179571A US 3785768D A US3785768D A US 3785768DA US 3785768 A US3785768 A US 3785768A
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methyl
naphthyl
dyeing
polyacrylonitrile
dimethyl
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US00179571A
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K Walz
K Gerlach
M Schwarz
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Bayer AG
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Bayer AG
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    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
    • D06P1/44—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders
    • D06P1/655—Compounds containing ammonium groups
    • D06P1/66—Compounds containing ammonium groups containing quaternary ammonium groups
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
    • D06P3/70—Material containing nitrile groups
    • D06P3/76—Material containing nitrile groups using basic dyes
    • 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
    • Y10S8/927—Polyacrylonitrile fiber

Definitions

  • the invention relates to a process for the dyeing of fibre materials produced from polyacrylonitrile or R stands for a C C ,-alkyl, C C ,,alkenyl or an optionally substituted cycloaklyl or aralkyl radical;
  • R and R independently of one another stand for C -C -alkyl or C,-C,-hydroxyalkyl radicals or form together with the nitrogen atom a heterocyclicring and
  • A means an optionally substituted naphthyl or tetrahydronaphthyl radical.
  • R there may be mentioned by way of example: as alkyl radicals, the n-octyl, Z-ethylhexyl, n-decyl, 2,2- dimethyl-octyl, n-dodecyl, 2,2 -dirnethyl-decyl, 2- methyl-undecyl, n-tridecyl, 2-methyl-dodecyl, ntetradecyl, n-hexadecyl and n-octadecyl radicals;
  • alkenyl radicals the tetradecenyl, hexadecenyl and octadecenyl radicals
  • cycloaklyl radicals the cyclohexyl, methylcyclohexyl, dimethyl-cyclohexyl, decahydronaphthyl and abietyl radicals;
  • aralkyl radicals the benzyl, chlorobenzyl, phenylethyl, 9( l)-phenyl-stearyl and naphthyl-(l )methyl radicals.
  • C,-C -alkyl and hydroxyalkyl radicals for R and R there may be mentioned, by way of example, the methyl, ethyl, propyl, i-propyl, n-butyl, sec. -butyl, 2- hydroxyethyl, 2-hydroxypropyl-(l 3-hydroxypropyl- (l) and 4-hydr'oxybutyl-(l) radicals.
  • Suitable heterocyclic rings which may be formed from R and R are primarily the pyrrolidine, piperidine and morpholine rings.
  • the naphthalene or tetrahydronaphthalene radical may be linked in the lor 2-position to the methylene group.
  • the naphthalene ring is preferably linked in the l-position, the tetrahydronaphthalene ring preferably in the 2-position.
  • Suitable substituents for the naphthalene or tetrahydro-naphthalene radical are, for example, C,C -alkyl radicals such as the methyl, ethyl, i-propyl or tert. -butyl radicals; furthermore, halogen atoms such as the chlorine or bromine atom; or nitro groups.
  • Inorganic as well as organic acids are suitable for salt formation with the ammonium bases of the formula (I); preferred acids are the known inorganic acids, such as hydrochloric acid, hydrobromic acid, hydroiodic acid, sulphuric acid, nitric acid or perchloric acid; and organic acids, such as the lower aliphatic carboxylic acids, e.g., formic acid, acetic acid; aromatic sulphonic acids, such as benzene-sulphonic acid, toluenesulphonic acid; and the semie'sters of sulphuric acid, such as methyl-sulphuric acid and ethyl'sulphuric acid.
  • preferred acids are the known inorganic acids, such as hydrochloric acid, hydrobromic acid, hydroiodic acid, sulphuric acid, nitric acid or perchloric acid
  • organic acids such as the lower aliphatic carboxylic acids, e.g., formic acid, acetic acid; aromatic
  • R R independently of one another, stand for a methyl, ethyl, 2-hydroxyethyl or 2-hydroxypropyl- (1) group.
  • Examples of compounds suitable for the process are the following: dimethyl-decyl-[naphthyl-( l )-methyl]-ammonium chloride, dimethyl-decyl-[naphthyl-(2)-methyl]- ammonium bromide, dimethy-l-dodecyl-[naphthyl-( l methyl]-ammonium chloride, dimethyl-tetradecyl- [naphthyl-( 1 )-methyl]-ammonium chloride, dimethylhexadecyl-[naphthyl-( l )methyll-ammonium bromide, dimethyl-octadecyl-[naphthyl l )-methyl]-ammonium chloride, dimethyl-octadecenyl-[naphthyl'( l methyl]-ammonium acetate, diethyl-dodec
  • the compounds to be used according to the invention can be prepared in known manner, for example, by reacting halomethylated naphthalenes or tetrahydronaphthalense with the appropriate tertiary amines.
  • the reaction may be carried out in the presence of solvents, such as water, alcohols, glycols, formamide, dimethyl formamide, dimethyl sulphoxide or halogenated hydrocarbons, at temperatures from 30 to l50C.
  • Suitable cationic dyestuffs are dyestuffs from various classes of compounds, for example, diphenyl-methane, triphenylmethane and rhodamine dyestuffs; azo or anthraquinone dyestuffs containing onium groups; furthermore, thiazine, oxazine, methine and azomethine dyestuffds, such as are described, for example, in Ullrnanns Encyclopadie der technis'chen Chemie, Third Edition 1970, Supplement, page 225.
  • Dyeing of the polyacrylonitrile fibre materials can be carried out in the usual way, by introducing the material to be dyed into an aqueous dyebath which has been heated to about 50 60C and contains the cationic dyestuff, compounds of the formula (I), added salts, such as sodium acetate or sodium sulphate, and acids, such as acetic acid or formic acid; subsequently raising the temperature of the dyebath to approximately 100C in the course of about 30 minutes; and then keeping the dyebath at the same temperature until it is exhausted.
  • aqueous dyebath which has been heated to about 50 60C and contains the cationic dyestuff, compounds of the formula (I), added salts, such as sodium acetate or sodium sulphate, and acids, such as acetic acid or formic acid
  • fibre materials which consist of polyacrylonitrile or of acrylonitrile-containing copolymers or contain uch polymers or copolymers and which may be present in various stages of processing, for example, as spun cables, combed material, loose material, filaments, yarns, fabrics or knitted fabrics, with outstanding levelness and in deep shades.
  • the compounds of the formula (I) Compared with the quaternary ammonium salts commonly used for the dyeing of polyacrylonitrile with cationic dyestuffs, the compounds of the formula (I) have a substantially increased effectiveness which permits of working with substantially smaller amounts of auxiliaries.
  • the increased effectiveness is of particular importance for the dyeing of dyestuffs of high affinity i.e., which draw very fast, since in this case the known retarders have to be used in large amounts, in order to obtain level dyeings.
  • EXAMPLE l The bath is heated to 98C and kept at the same temperature for 60 minutes. A level blue dyeing is obtained.
  • R and R independently of one another stand for a methyl, ethyl, 2-hydroxyethyl or 2-hydroxypropyl- Yarn of polyacrylonitrile fibres is introduced in a li- (1) group. quor ratio of l 40 into a bath which has been heated 3.

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Abstract


Process for dyeing fibre materials consisting of polyacrylonitrile-containing copolymers with cationic dyestuffs in level and deep shades by using as dyeing auxiliaries quaternary ammonium salts which are derived from free ammonium bases of the formula
WHEREIN THE R''s and A are as defined below.

D R A W I N G

Description

United States Pa-ten r 91 [11] 39 Walz et al. 1 .Ian. 15, 1974 [54] PROCESS FOR THE DYEHNG 01F FIBRE 2,986,444 5/1961 Rokohl et al. 8/84 MATERIAL CONSISTHNG 0 2,145,527 I/1939 Polak et a1. 8/84 X 4 3,446,569 5/1969 Braun ct a1... 8/84 POLYAQRYLONITRHJE OR $564,630 2/1971 Moussulli 8/84 X ACRYLONl'lRlLE-CONTAINING COPOLYMERS [75] Inventors: Klaus Walz,'Leverkusen; Klaus Primary 2 Levy Gerlach Cologne; Max Schwarz, Assistant ExammerT. J. erbert, Jr. Berg.-Neukirchen, all of Germany Anomey plumley & Tyner- [73] Assignee: Bayer Aktiengesellschaft,
Leverkusen, Germany T A T [22] Filed: Sept. 10, 1971 [57] ABS R C [21] Appl. No.: 179,571 Process for dyeing fibre. materials consisting of p01yacrylonitrile-containing copolymers with cationic dyestuffs in level and deep shades by using as dyeing [30] Foreign Application Priority Data auxiliaries quaternary ammonium salts which are de- Sept. 11, 1970 Germany 2044990 rived from f ammonium bases of the formula [52] U.S. Cl 8/169, 8/84, 8/172,
[51] int. Cl. D06p 5 /06, D06p 3/76 RNCHz-A on- [58] Field of Search 8/84, 172, 177 AB,
[ References Cited wherein the Rs and A are as defined below.
UNITED STATES PATENTS I 2,989,361 6/1961 He'es 8/84 X 4 Claims, No Drawings PROCESS FOR THE memo or FIBRE MATERIAL consrsrme or POLYACRYLONITRILE on ACRYLONlTRlLE-CONTAINING COPOLYMERS The invention relates to a process for the dyeing of fibre materials produced from polyacrylonitrile or R stands for a C C ,-alkyl, C C ,,alkenyl or an optionally substituted cycloaklyl or aralkyl radical;
R and R independently of one another stand for C -C -alkyl or C,-C,-hydroxyalkyl radicals or form together with the nitrogen atom a heterocyclicring and A means an optionally substituted naphthyl or tetrahydronaphthyl radical.
For R there may be mentioned by way of example: as alkyl radicals, the n-octyl, Z-ethylhexyl, n-decyl, 2,2- dimethyl-octyl, n-dodecyl, 2,2 -dirnethyl-decyl, 2- methyl-undecyl, n-tridecyl, 2-methyl-dodecyl, ntetradecyl, n-hexadecyl and n-octadecyl radicals;
as alkenyl radicals, the tetradecenyl, hexadecenyl and octadecenyl radicals;
as cycloaklyl radicals, the cyclohexyl, methylcyclohexyl, dimethyl-cyclohexyl, decahydronaphthyl and abietyl radicals;
as aralkyl radicals, the benzyl, chlorobenzyl, phenylethyl, 9( l)-phenyl-stearyl and naphthyl-(l )methyl radicals.
As C,-C -alkyl and hydroxyalkyl radicals for R and R there may be mentioned, by way of example, the methyl, ethyl, propyl, i-propyl, n-butyl, sec. -butyl, 2- hydroxyethyl, 2-hydroxypropyl-(l 3-hydroxypropyl- (l) and 4-hydr'oxybutyl-(l) radicals.
Suitable heterocyclic rings which may be formed from R and R are primarily the pyrrolidine, piperidine and morpholine rings.
The naphthalene or tetrahydronaphthalene radical may be linked in the lor 2-position to the methylene group. However, the naphthalene ring is preferably linked in the l-position, the tetrahydronaphthalene ring preferably in the 2-position.
Suitable substituents for the naphthalene or tetrahydro-naphthalene radical are, for example, C,C -alkyl radicals such as the methyl, ethyl, i-propyl or tert. -butyl radicals; furthermore, halogen atoms such as the chlorine or bromine atom; or nitro groups.
Inorganic as well as organic acids are suitable for salt formation with the ammonium bases of the formula (I); preferred acids are the known inorganic acids, such as hydrochloric acid, hydrobromic acid, hydroiodic acid, sulphuric acid, nitric acid or perchloric acid; and organic acids, such as the lower aliphatic carboxylic acids, e.g., formic acid, acetic acid; aromatic sulphonic acids, such as benzene-sulphonic acid, toluenesulphonic acid; and the semie'sters of sulphuric acid, such as methyl-sulphuric acid and ethyl'sulphuric acid.
In the dyeing process according to the invention those quaternary ammonium salts have proved particularly satisfactory which are derived from ammonium bases of the formula (I) in which R is a C C, -alkenyl, C -'C -alkyl or, preferably, a
C C -alkyl radical; and
R R independently of one another, stand for a methyl, ethyl, 2-hydroxyethyl or 2-hydroxypropyl- (1) group.
Examples of compounds suitable for the process are the following: dimethyl-decyl-[naphthyl-( l )-methyl]-ammonium chloride, dimethyl-decyl-[naphthyl-(2)-methyl]- ammonium bromide, dimethy-l-dodecyl-[naphthyl-( l methyl]-ammonium chloride, dimethyl-tetradecyl- [naphthyl-( 1 )-methyl]-ammonium chloride, dimethylhexadecyl-[naphthyl-( l )methyll-ammonium bromide, dimethyl-octadecyl-[naphthyl l )-methyl]-ammonium chloride, dimethyl-octadecenyl-[naphthyl'( l methyl]-ammonium acetate, diethyl-dodecyl- [naphthyl-(l)-methyl]-ammonium iodide, diethyldodecyl-[naphthyl-(2)-methyl]-ammonium chloride, diethyl-tetradecyl-[tetrahydronaphthyl-(2)-methyl]- ammonium chloride, dibutyl-octyl-[naphthyl-(l)- methyl]-ammonium bromide, di-(hydroxyethyl)- tetradecyl-[naphthyl-( l )-methyl]-ammonium chloride, di-(hydroxypropyl)-hexadecyl-[naphthyl-( 1 )-methyl]- ammonium sulphate, hydroxybutyl-methyl-dodecyl- [naphthyl-(l)-rnethyl]-ammonium methosulphate, dimethyl-abietyl-[naphthyl-( l )-methyl]-ammonium chloride, dibutyl-cyclohexyl-[naphthyl( 1 )-methyl]- ammonium bromide, dibutyl-benzyl-[naphthyl-(l)- methyl]-ammonium bromide, diernethyl-di-(naphthyl- (l)-methyl)-ammonium chloride, [4-chloronaphthyl- (l )-methyl]-dodecyl-pyrrolidinium chloride and [Naphthyl-( l )-methyl]-dodecyl-piperidinium toluenesulphonate.
The compounds to be used according to the invention can be prepared in known manner, for example, by reacting halomethylated naphthalenes or tetrahydronaphthalense with the appropriate tertiary amines. The reaction may be carried out in the presence of solvents, such as water, alcohols, glycols, formamide, dimethyl formamide, dimethyl sulphoxide or halogenated hydrocarbons, at temperatures from 30 to l50C.
Suitable cationic dyestuffs are dyestuffs from various classes of compounds, for example, diphenyl-methane, triphenylmethane and rhodamine dyestuffs; azo or anthraquinone dyestuffs containing onium groups; furthermore, thiazine, oxazine, methine and azomethine dyestuffds, such as are described, for example, in Ullrnanns Encyclopadie der technis'chen Chemie, Third Edition 1970, Supplement, page 225.
The necessary amounts of compounds of the formula (I) to be used according to the invention can easily be determined by preliminary experiments. In general, there are used amounts of about 0.25 to 2.5 percent of these compounds, referred to the weight of the material to be dyed.
tate, vinyl alcohol, acrylic and methacrylic acid, acrylic and methacrylic acid esters, allyl chloroacetate, or basic vinyl compounds such as vinyl-imidazole, vinylbenzimidazole, vinyl-pyridine, vinyl-methylpyridine, vinyl-pyrimidine, provided that the proportion of these co-monomers in the copolymers does not amount to more than percent by weight Dyeing of the polyacrylonitrile fibre materials can be carried out in the usual way, by introducing the material to be dyed into an aqueous dyebath which has been heated to about 50 60C and contains the cationic dyestuff, compounds of the formula (I), added salts, such as sodium acetate or sodium sulphate, and acids, such as acetic acid or formic acid; subsequently raising the temperature of the dyebath to approximately 100C in the course of about 30 minutes; and then keeping the dyebath at the same temperature until it is exhausted. It is also possible to pretreat the material to be dyed at a temperature of 40 100 C with a liquor which contains the usual salts and acids as well as compounds of the formula (I), but does not contain any dyestuff; to add the dyestuff only then, and to carry out the dyeing at 100C. Finally, it is also possible immediately to introduce the material to be dyed into a dyebath which contains compounds of the formula (1) and has been heated to approximately 100 C.
With the aid of the process according to the invention it is possible to dye fibre materials which consist of polyacrylonitrile or of acrylonitrile-containing copolymers or contain uch polymers or copolymers and which may be present in various stages of processing, for example, as spun cables, combed material, loose material, filaments, yarns, fabrics or knitted fabrics, with outstanding levelness and in deep shades.
Compared with the quaternary ammonium salts commonly used for the dyeing of polyacrylonitrile with cationic dyestuffs, the compounds of the formula (I) have a substantially increased effectiveness which permits of working with substantially smaller amounts of auxiliaries. The increased effectiveness is of particular importance for the dyeing of dyestuffs of high affinity i.e., which draw very fast, since in this case the known retarders have to be used in large amounts, in order to obtain level dyeings.
EXAMPLE l The bath is heated to 98C and kept at the same temperature for 60 minutes. A level blue dyeing is obtained.
An equally level blue dyeing was obtained when the dimethyl-dodecyl-(naphthyl-( l )-methyl)-ammonium chloride was replaced with the same amount of one of the following compounds a. dimethyl-dodecyl-[naphthyl-(1 )-methyl]- ammonium bromide dimethyl-tetradecyl-[naphthyl-( 1 )-methyl]- ammonium bromide c. diethyldodecyl-[naphthyl-( l )-methyl]- ammonium chloride d. dimethyl-dodecyl-[naphthyl-(2)methyl]- EXAMPLE 2 Yarns of polyacrylonitrile fibres are introduced in a liquor ratio of 1 40 into a dyebath which has been heated to C and contains, per litre,
0.1 g of the cationic dyestuff mentioned in Example 0.25 g sodium acetate 0.3 g glacial acetic acid and 0.3 g of the compound of the formula The bath is heated to 98C and kept at the same temperature for 60 minutes. The bath is then completely exhausted. A blue yarn is obtained which is dyed with outstanding levelness.
A yarn dyed with the same levelness was obtained when the dimethyl-tetradccyl-[naphthyl-(1)-methyl]- ammonium chloride was replaced with the stated amounts of one of the following compounds:
a. 0.275 g dimethyl-hexadecyl-[naphthyl-(l)- methyll-ammonium chloride b. 0.25 g dimethyl-octadecyl-[naphthyl-( 1 )-methyl]- ammonium chloride c. 0.25 g dimethyl-octadecenyl-[naphthyl-( l methyl1-ammonium chloride EXAMPLE 3 Yarns of polyacrylonitrile fibres are introduced in a liquor ratio of l 40 into a bath which has been heated m to 80C and contains, per litre, c n, zr cn, 0.l g ofthe cationic dyestuff described in Example 1 (3H8 0.25 g sodium acetate 0.3 g glacial acetic acid 5 0.35 g of a mixture of the compounds of the formula The bath is heated to and p at the Same perature for 60 minutes. A level red dyeing is obtained.
CH3 1 We claim: 1. In the process for dyeing fibers of polymers of ac- Cu-Hg5N-CH2 01- rylonitrile containing at least 80 percent by weight acrylonitrile with cationic dyestuffs the improvement which comprises performing the dyeing in the presence of a dyeing auxiliary which is a quaternary ammonium a V salt of an ammonium base of the formula:
and V 5 me f;
[n-ay-ott-{l 011- C H ll H I R2 14 |C a C1 wherein CH3 20 R is a C C alkyl or a C -C alkenyl; R and R independently of one another, are C -C alkyl or C C hydroxyalkyl, or a heterocyclic ring when The bath is gradually heated to 98C and kept at the joined tog-ether with the nitrogen atom; and
same temperature for 60 minutes. A blue dyeing of ex- 5 A is vaphthyl t,etrahydronapgthyll Fi of .Said cement levelness is obtained. 2 radicals substituted by C, 4 a ky a 0, 0r nitro.
2. The process of claim 1 wherein I R stands for a C ,C alkyl or C C, -alkenyl radi EXAMPLE 4 cal; and
R and R independently of one another stand for a methyl, ethyl, 2-hydroxyethyl or 2-hydroxypropyl- Yarn of polyacrylonitrile fibres is introduced in a li- (1) group. quor ratio of l 40 into a bath which has been heated 3. The process of claim 1 wherein to 80C and contains, per litre R stands for a C, C -alkyl radical, and
0.04 g of the dyestuff of the formula R andR stand for a methyl group.
85 i e CHa-CHa-N (C 8) 3 CHJS O 4 0.25 g sodium acetate 4. Fibre materials of polyacrylonitrile or acryloni- 0.3 g glacial acetic acid and trile-containing copolymers dyed according to claim 1. 0.1 g of the compound of the formula

Claims (3)

  1. 2. The process of claim 1 wherein R stands for a C10-C18-alkyl or C10-C18-alkenyl radical; and R1 and R2 independently of one another stand for a methyl, ethyl, 2-hydroxyethyl or 2-hydroxypropyl-(1) group.
  2. 3. The process of claim 1 wherein R stands for a C12-C18-alkyl radical, and R1 and R2 stand for a methyl group.
  3. 4. Fibre materials of polyacrylonitrile or acrylonitrile-containing copolymers dyed according to claim 1.
US00179571A 1970-09-11 1971-09-10 Process for the dyeing of fibre material consisting of polyacrylonitrile or acrylonitrile-containing copolymers Expired - Lifetime US3785768A (en)

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3854872A (en) * 1972-04-07 1974-12-17 Mfg Prod Chimi Protex Soc Fr A Process for dyeing of polyacrylonitrile fibers
US4181499A (en) * 1974-10-29 1980-01-01 Ciba-Geigy Corporation Process for the level dyeing of polyacrylonitrile materials of slow, normal and rapid absorptive capacity
US4233028A (en) * 1975-07-14 1980-11-11 Ciba-Geigy Corporation Process for the level dyeing of polyacrylonitrile materials of slow, normal and rapid absorptive capacity

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2145527A (en) * 1935-02-16 1939-01-31 American Enka Corp Manufacture of artificial silk
US2986444A (en) * 1958-05-14 1961-05-30 Basf Ag Production of level dyeings of basic dyestuffs on structures of acrylonitrile polymers
US2989361A (en) * 1961-06-20 Dyeing process
US3446569A (en) * 1963-05-11 1969-05-27 Hoechst Ag Aqueous solutions of phthalocyanine pigments and process for preparing them
US3564630A (en) * 1966-07-05 1971-02-23 Celanese Corp Polyamide fibers and fiber blends of enhanced dyeability

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2989361A (en) * 1961-06-20 Dyeing process
US2145527A (en) * 1935-02-16 1939-01-31 American Enka Corp Manufacture of artificial silk
US2986444A (en) * 1958-05-14 1961-05-30 Basf Ag Production of level dyeings of basic dyestuffs on structures of acrylonitrile polymers
US3446569A (en) * 1963-05-11 1969-05-27 Hoechst Ag Aqueous solutions of phthalocyanine pigments and process for preparing them
US3564630A (en) * 1966-07-05 1971-02-23 Celanese Corp Polyamide fibers and fiber blends of enhanced dyeability

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3854872A (en) * 1972-04-07 1974-12-17 Mfg Prod Chimi Protex Soc Fr A Process for dyeing of polyacrylonitrile fibers
US4181499A (en) * 1974-10-29 1980-01-01 Ciba-Geigy Corporation Process for the level dyeing of polyacrylonitrile materials of slow, normal and rapid absorptive capacity
US4233028A (en) * 1975-07-14 1980-11-11 Ciba-Geigy Corporation Process for the level dyeing of polyacrylonitrile materials of slow, normal and rapid absorptive capacity

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IT939395B (en) 1973-02-10
CH541665A (en) 1973-05-30
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BE772477A (en) 1972-01-17
ES394965A1 (en) 1974-03-16
JPS5247062B1 (en) 1977-11-30
FR2106457B1 (en) 1976-05-28
CH1333271A4 (en) 1973-05-30
GB1301780A (en) 1973-01-04
DE2044990A1 (en) 1972-03-16
NL7112436A (en) 1972-03-14
DE2044990B2 (en) 1977-06-16
CA954255A (en) 1974-09-10

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