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 PDFInfo
- Publication number
- 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
- Authority
- US
- United States
- Prior art keywords
- methyl
- naphthyl
- dyeing
- polyacrylonitrile
- dimethyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 239000000463 material Substances 0.000 title claims abstract description 16
- 238000000034 method Methods 0.000 title claims abstract description 14
- 229920002239 polyacrylonitrile Polymers 0.000 title claims abstract description 12
- 239000000835 fiber Substances 0.000 title claims abstract description 11
- 229920001577 copolymer Polymers 0.000 title claims abstract description 10
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 title claims description 4
- 238000004043 dyeing Methods 0.000 title abstract description 19
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 4
- 125000002091 cationic group Chemical group 0.000 abstract description 8
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 abstract description 5
- 150000003242 quaternary ammonium salts Chemical class 0.000 abstract description 4
- -1 aralkyl radical Chemical class 0.000 description 24
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 15
- 150000001875 compounds Chemical class 0.000 description 14
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- 239000000975 dye Substances 0.000 description 7
- 229960000583 acetic acid Drugs 0.000 description 5
- 125000001624 naphthyl group Chemical group 0.000 description 5
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 4
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 235000019270 ammonium chloride Nutrition 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 150000003254 radicals Chemical class 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 239000001632 sodium acetate Substances 0.000 description 4
- 235000017281 sodium acetate Nutrition 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 239000012362 glacial acetic acid Substances 0.000 description 3
- 125000000623 heterocyclic group Chemical group 0.000 description 3
- 239000001117 sulphuric acid Substances 0.000 description 3
- 235000011149 sulphuric acid Nutrition 0.000 description 3
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 239000004744 fabric Substances 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- 229940093915 gynecological organic acid Drugs 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 235000005985 organic acids Nutrition 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- QLAJNZSPVITUCQ-UHFFFAOYSA-N 1,3,2-dioxathietane 2,2-dioxide Chemical compound O=S1(=O)OCO1 QLAJNZSPVITUCQ-UHFFFAOYSA-N 0.000 description 1
- OSSNTDFYBPYIEC-UHFFFAOYSA-N 1-ethenylimidazole Chemical compound C=CN1C=CN=C1 OSSNTDFYBPYIEC-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
- YRPYTFXEHXXYQW-UHFFFAOYSA-N 2-ethenyl-1h-benzimidazole Chemical compound C1=CC=C2NC(C=C)=NC2=C1 YRPYTFXEHXXYQW-UHFFFAOYSA-N 0.000 description 1
- ZDHWTWWXCXEGIC-UHFFFAOYSA-N 2-ethenylpyrimidine Chemical compound C=CC1=NC=CC=N1 ZDHWTWWXCXEGIC-UHFFFAOYSA-N 0.000 description 1
- KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-vinylpyridine Chemical compound C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-UHFFFAOYSA-N 0.000 description 1
- BCHZICNRHXRCHY-UHFFFAOYSA-N 2h-oxazine Chemical compound N1OC=CC=C1 BCHZICNRHXRCHY-UHFFFAOYSA-N 0.000 description 1
- AGIJRRREJXSQJR-UHFFFAOYSA-N 2h-thiazine Chemical compound N1SC=CC=C1 AGIJRRREJXSQJR-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- ZXWNFKKVGPYFRR-UHFFFAOYSA-N 3-ethenyl-2-methylpyridine Chemical compound CC1=NC=CC=C1C=C ZXWNFKKVGPYFRR-UHFFFAOYSA-N 0.000 description 1
- 239000005695 Ammonium acetate Substances 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 1
- IMROMDMJAWUWLK-UHFFFAOYSA-N Ethenol Chemical compound OC=C IMROMDMJAWUWLK-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
- 229940043376 ammonium acetate Drugs 0.000 description 1
- 229940107816 ammonium iodide Drugs 0.000 description 1
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 1
- 239000001166 ammonium sulphate Substances 0.000 description 1
- 235000011130 ammonium sulphate Nutrition 0.000 description 1
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000004568 cement Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000004803 chlorobenzyl group Chemical group 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 1
- CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical compound C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 229940071870 hydroiodic acid Drugs 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 125000005397 methacrylic acid ester group Chemical group 0.000 description 1
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 description 1
- JZMJDSHXVKJFKW-UHFFFAOYSA-N methyl sulfate Chemical compound COS(O)(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-N 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- VMBJJCDVORDOCF-UHFFFAOYSA-N prop-2-enyl 2-chloroacetate Chemical compound ClCC(=O)OCC=C VMBJJCDVORDOCF-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- PYWVYCXTNDRMGF-UHFFFAOYSA-N rhodamine B Chemical compound [Cl-].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=CC=C1C(O)=O PYWVYCXTNDRMGF-UHFFFAOYSA-N 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 125000005063 tetradecenyl group Chemical group C(=CCCCCCCCCCCCC)* 0.000 description 1
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical group C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
- AAAQKTZKLRYKHR-UHFFFAOYSA-N triphenylmethane Chemical compound C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 AAAQKTZKLRYKHR-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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.
Landscapes
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Coloring (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19702044990 DE2044990C3 (de) | 1970-09-11 | Ein Verfahren zum Färben von Fasermaterialien aus Polyacrylnitril oder acrylnitrilhaltigen Mischpolymerisaten |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3785768A true US3785768A (en) | 1974-01-15 |
Family
ID=5782176
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US00179571A Expired - Lifetime US3785768A (en) | 1970-09-11 | 1971-09-10 | Process for the dyeing of fibre material consisting of polyacrylonitrile or acrylonitrile-containing copolymers |
Country Status (11)
Cited By (3)
| 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)
| 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 |
-
1971
- 1971-09-08 JP JP46068992A patent/JPS5247062B1/ja active Pending
- 1971-09-08 CA CA122,298A patent/CA954255A/en not_active Expired
- 1971-09-09 AT AT783571A patent/AT316478B/de active
- 1971-09-09 IT IT52779/71A patent/IT939395B/it active
- 1971-09-09 NL NL7112436A patent/NL7112436A/xx unknown
- 1971-09-10 CH CH1333271D patent/CH1333271A4/xx unknown
- 1971-09-10 CH CH1333271A patent/CH541665A/de unknown
- 1971-09-10 FR FR7132803A patent/FR2106457B1/fr not_active Expired
- 1971-09-10 GB GB4236271A patent/GB1301780A/en not_active Expired
- 1971-09-10 ES ES394965A patent/ES394965A1/es not_active Expired
- 1971-09-10 BE BE772477A patent/BE772477A/xx unknown
- 1971-09-10 US US00179571A patent/US3785768A/en not_active Expired - Lifetime
Patent Citations (5)
| 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)
| 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 |
Also Published As
| Publication number | Publication date |
|---|---|
| GB1301780A (enrdf_load_stackoverflow) | 1973-01-04 |
| CA954255A (en) | 1974-09-10 |
| CH1333271A4 (enrdf_load_stackoverflow) | 1973-05-30 |
| BE772477A (fr) | 1972-01-17 |
| NL7112436A (enrdf_load_stackoverflow) | 1972-03-14 |
| DE2044990A1 (de) | 1972-03-16 |
| CH541665A (de) | 1973-05-30 |
| FR2106457B1 (enrdf_load_stackoverflow) | 1976-05-28 |
| ES394965A1 (es) | 1974-03-16 |
| AT316478B (de) | 1974-07-10 |
| JPS5247062B1 (enrdf_load_stackoverflow) | 1977-11-30 |
| IT939395B (it) | 1973-02-10 |
| DE2044990B2 (de) | 1977-06-16 |
| FR2106457A1 (enrdf_load_stackoverflow) | 1972-05-05 |
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