US3700405A - Dyeing of polycarbonamides of bis(paraamino-cyclohexyl)methane and dodecanediodic acid with anionic dyes - Google Patents
Dyeing of polycarbonamides of bis(paraamino-cyclohexyl)methane and dodecanediodic acid with anionic dyes Download PDFInfo
- Publication number
- US3700405A US3700405A US102518A US3700405DA US3700405A US 3700405 A US3700405 A US 3700405A US 102518 A US102518 A US 102518A US 3700405D A US3700405D A US 3700405DA US 3700405 A US3700405 A US 3700405A
- Authority
- US
- United States
- Prior art keywords
- acid
- dyeing
- dyes
- polycarbonamides
- paraamino
- 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
- 238000004043 dyeing Methods 0.000 title abstract description 15
- 239000000975 dye Substances 0.000 title description 11
- 125000000129 anionic group Chemical group 0.000 title description 9
- 239000002253 acid Substances 0.000 title description 5
- DZIHTWJGPDVSGE-UHFFFAOYSA-N 4-[(4-aminocyclohexyl)methyl]cyclohexan-1-amine Chemical compound C1CC(N)CCC1CC1CCC(N)CC1 DZIHTWJGPDVSGE-UHFFFAOYSA-N 0.000 title description 2
- 239000000835 fiber Substances 0.000 abstract description 15
- 239000004952 Polyamide Substances 0.000 abstract description 12
- 229920002647 polyamide Polymers 0.000 abstract description 12
- 238000000034 method Methods 0.000 abstract description 11
- 239000000969 carrier Substances 0.000 abstract description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical class [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract description 4
- 230000002378 acidificating effect Effects 0.000 abstract description 4
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 4
- 239000001257 hydrogen Substances 0.000 abstract description 4
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical class [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 abstract 1
- BDAGIHXWWSANSR-UHFFFAOYSA-N formic acid Substances OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 7
- XSIFPSYPOVKYCO-UHFFFAOYSA-N butyl benzoate Chemical compound CCCCOC(=O)C1=CC=CC=C1 XSIFPSYPOVKYCO-UHFFFAOYSA-N 0.000 description 6
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 5
- 239000012965 benzophenone Substances 0.000 description 5
- -1 e.g. Substances 0.000 description 5
- 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 4
- 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 4
- 150000004056 anthraquinones Chemical class 0.000 description 4
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 4
- SESFRYSPDFLNCH-UHFFFAOYSA-N benzyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCC1=CC=CC=C1 SESFRYSPDFLNCH-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000000080 wetting agent Substances 0.000 description 4
- 239000000986 disperse dye Substances 0.000 description 3
- 235000019253 formic acid Nutrition 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 229920001778 nylon Polymers 0.000 description 3
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 3
- PKZJLOCLABXVMC-UHFFFAOYSA-N 2-Methoxybenzaldehyde Chemical compound COC1=CC=CC=C1C=O PKZJLOCLABXVMC-UHFFFAOYSA-N 0.000 description 2
- XRXMNWGCKISMOH-UHFFFAOYSA-N 2-bromobenzoic acid Chemical compound OC(=O)C1=CC=CC=C1Br XRXMNWGCKISMOH-UHFFFAOYSA-N 0.000 description 2
- IKCLCGXPQILATA-UHFFFAOYSA-N 2-chlorobenzoic acid Chemical compound OC(=O)C1=CC=CC=C1Cl IKCLCGXPQILATA-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 229920002292 Nylon 6 Polymers 0.000 description 2
- 229920002302 Nylon 6,6 Polymers 0.000 description 2
- SJEYSFABYSGQBG-UHFFFAOYSA-M Patent blue Chemical compound [Na+].C1=CC(N(CC)CC)=CC=C1C(C=1C(=CC(=CC=1)S([O-])(=O)=O)S([O-])(=O)=O)=C1C=CC(=[N+](CC)CC)C=C1 SJEYSFABYSGQBG-UHFFFAOYSA-M 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 229920001213 Polysorbate 20 Polymers 0.000 description 2
- 244000028419 Styrax benzoin Species 0.000 description 2
- 235000000126 Styrax benzoin Nutrition 0.000 description 2
- 235000008411 Sumatra benzointree Nutrition 0.000 description 2
- 239000000980 acid dye Substances 0.000 description 2
- 229960002130 benzoin Drugs 0.000 description 2
- 229960002903 benzyl benzoate Drugs 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- PBOIUUROGJVVNC-UHFFFAOYSA-L disodium 2-hydroxy-5-[[4-[[2-methoxy-4-[(3-sulfonatophenyl)diazenyl]phenyl]carbamoylamino]phenyl]diazenyl]benzoate Chemical compound [Na+].[Na+].COc1cc(ccc1NC(=O)Nc1ccc(cc1)N=Nc1ccc(O)c(c1)C([O-])=O)N=Nc1cccc(c1)S([O-])(=O)=O PBOIUUROGJVVNC-UHFFFAOYSA-L 0.000 description 2
- NJXPQVNXQNPYRT-UHFFFAOYSA-L disodium;3-amino-4-[[4-[4-[[4-(4-methylphenyl)sulfonyloxyphenyl]diazenyl]phenyl]phenyl]diazenyl]naphthalene-2,7-disulfonate Chemical compound [Na+].[Na+].C1=CC(C)=CC=C1S(=O)(=O)OC1=CC=C(N=NC=2C=CC(=CC=2)C=2C=CC(=CC=2)N=NC=2C3=CC=C(C=C3C=C(C=2N)S([O-])(=O)=O)S([O-])(=O)=O)C=C1 NJXPQVNXQNPYRT-UHFFFAOYSA-L 0.000 description 2
- XPRMZBUQQMPKCR-UHFFFAOYSA-L disodium;8-anilino-5-[[4-[(3-sulfonatophenyl)diazenyl]naphthalen-1-yl]diazenyl]naphthalene-1-sulfonate Chemical compound [Na+].[Na+].[O-]S(=O)(=O)C1=CC=CC(N=NC=2C3=CC=CC=C3C(N=NC=3C4=CC=CC(=C4C(NC=4C=CC=CC=4)=CC=3)S([O-])(=O)=O)=CC=2)=C1 XPRMZBUQQMPKCR-UHFFFAOYSA-L 0.000 description 2
- TVIDDXQYHWJXFK-UHFFFAOYSA-N dodecanedioic acid Chemical compound OC(=O)CCCCCCCCCCC(O)=O TVIDDXQYHWJXFK-UHFFFAOYSA-N 0.000 description 2
- 235000019233 fast yellow AB Nutrition 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 235000019382 gum benzoic Nutrition 0.000 description 2
- XIKIUQUXDNHBFR-UHFFFAOYSA-N monobenzyl phthalate Chemical compound OC(=O)C1=CC=CC=C1C(=O)OCC1=CC=CC=C1 XIKIUQUXDNHBFR-UHFFFAOYSA-N 0.000 description 2
- ZWLPBLYKEWSWPD-UHFFFAOYSA-N o-toluic acid Chemical compound CC1=CC=CC=C1C(O)=O ZWLPBLYKEWSWPD-UHFFFAOYSA-N 0.000 description 2
- FCJSHPDYVMKCHI-UHFFFAOYSA-N phenyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OC1=CC=CC=C1 FCJSHPDYVMKCHI-UHFFFAOYSA-N 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 2
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 2
- 239000004753 textile Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- PEAGNRWWSMMRPZ-UHFFFAOYSA-L woodstain scarlet Chemical compound [Na+].[Na+].OC1=CC=C2C=C(S([O-])(=O)=O)C=C(S([O-])(=O)=O)C2=C1N=NC(C=C1)=CC=C1N=NC1=CC=CC=C1 PEAGNRWWSMMRPZ-UHFFFAOYSA-L 0.000 description 2
- 101100117236 Drosophila melanogaster speck gene Proteins 0.000 description 1
- VCUFZILGIRCDQQ-KRWDZBQOSA-N N-[[(5S)-2-oxo-3-(2-oxo-3H-1,3-benzoxazol-6-yl)-1,3-oxazolidin-5-yl]methyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C1O[C@H](CN1C1=CC2=C(NC(O2)=O)C=C1)CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F VCUFZILGIRCDQQ-KRWDZBQOSA-N 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- 229920001966 Qiana Polymers 0.000 description 1
- UFUQRRYHIHJMPB-DUCFOALUSA-L Sirius red 4B Chemical compound [Na+].[Na+].OS(=O)(=O)c1cc2cc(NC(=O)c3ccccc3)ccc2c([O-])c1\N=N\c1ccc(cc1)\N=N\c1ccc(cc1)S([O-])(=O)=O UFUQRRYHIHJMPB-DUCFOALUSA-L 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- LIKZXCROQGHXTI-UHFFFAOYSA-M acid blue 25 Chemical compound [Na+].C1=2C(=O)C3=CC=CC=C3C(=O)C=2C(N)=C(S([O-])(=O)=O)C=C1NC1=CC=CC=C1 LIKZXCROQGHXTI-UHFFFAOYSA-M 0.000 description 1
- ZXGIHDNEIWPDFW-UHFFFAOYSA-M acid red 4 Chemical compound [Na+].COC1=CC=CC=C1N=NC1=CC(S([O-])(=O)=O)=C(C=CC=C2)C2=C1O ZXGIHDNEIWPDFW-UHFFFAOYSA-M 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 239000000987 azo dye Substances 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 125000002843 carboxylic acid group Chemical group 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 239000000982 direct dye Substances 0.000 description 1
- FPVGTPBMTFTMRT-UHFFFAOYSA-L disodium;2-amino-5-[(4-sulfonatophenyl)diazenyl]benzenesulfonate Chemical compound [Na+].[Na+].C1=C(S([O-])(=O)=O)C(N)=CC=C1N=NC1=CC=C(S([O-])(=O)=O)C=C1 FPVGTPBMTFTMRT-UHFFFAOYSA-L 0.000 description 1
- VQHWSAGRWJWMCJ-UHFFFAOYSA-K disodium;4-chloro-2-methyl-6-[(3-methyl-5-oxo-1-phenylpyrazol-2-id-4-yl)diazenyl]phenolate;chromium(3+);hydron Chemical compound [H+].[Na+].[Na+].[Cr+3].O=C1C(N=NC=2C(=C(C)C=C(Cl)C=2)[O-])=C(C)[N-]N1C1=CC=CC=C1.O=C1C(N=NC=2C(=C(C)C=C(Cl)C=2)[O-])=C(C)[N-]N1C1=CC=CC=C1 VQHWSAGRWJWMCJ-UHFFFAOYSA-K 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 1
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
- 229920000053 polysorbate 80 Polymers 0.000 description 1
- CKMPIIPZKJISCU-UHFFFAOYSA-M sodium;4,8-diamino-1,5-dihydroxy-9,10-dioxoanthracene-2-sulfonate Chemical class [Na+].O=C1C2=C(N)C=C(S([O-])(=O)=O)C(O)=C2C(=O)C2=C1C(O)=CC=C2N CKMPIIPZKJISCU-UHFFFAOYSA-M 0.000 description 1
- RIJLWEYDGZAVGC-UHFFFAOYSA-M sodium;5-methyl-2-[[4-(methylamino)-9,10-dioxoanthracen-1-yl]amino]benzenesulfonate Chemical compound [Na+].C1=2C(=O)C3=CC=CC=C3C(=O)C=2C(NC)=CC=C1NC1=CC=C(C)C=C1S([O-])(=O)=O RIJLWEYDGZAVGC-UHFFFAOYSA-M 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 229920001059 synthetic polymer Polymers 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
- 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
- D06P3/02—Material containing basic nitrogen
- D06P3/04—Material containing basic nitrogen containing amide groups
- D06P3/24—Polyamides; Polyurethanes
- D06P3/241—Polyamides; Polyurethanes using acid dyes
-
- 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
- D06P1/64—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 using compositions containing low-molecular-weight organic compounds without sulfate or sulfonate groups
- D06P1/651—Compounds without nitrogen
- D06P1/65106—Oxygen-containing compounds
-
- 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
- Y10S8/924—Polyamide fiber
Definitions
- the present invention relates to processes for dyeing polyamide fibers containing at least 90% of the repeating units of the formula wherein R is the same or different member of the class consisting of hydrogen and methyl. At least 40% by weight of the diamino constituent of the repeating units is of the trans, trans stereoisomeric configuration.
- these materials is the polyamide polycondensate of 4,4'- diamino-dicyclohexylmethane with dodecanedioic acid.
- Such material is commercially avail able from Du Pont in different grades, depending on finish, denier, etc., as nylon types 472 and 473, as well as Qiana.
- the latter materials have a silk-like handle, a density of 1.04 and a crystallinity similar to that of polyester fibers, as reported in an article entitled The Dyeing of Synthetic Polymer Fibers, A. Liddiard, appearing in Review of Progress in Coloration, vol. 1, p. 64, June l967-September 1969.
- the Liddiard article does disclose that the Du Pont type 472 polyamides may be dyed with disperse dyes at the boil in the presence of a carrier, or in the absence of a carrier at even higher temperatures.
- benzophenone With respect to carriers, the most preferred is benzophenone, however, this may be employed and mixed with other carriers such as butyl benzoate, especially in a 1:1 mixture.
- Other operable carriers include benzyl benzoate, phenyl benzoate, o-bromo benzoic acid, 2-chloro benzoic acid, mono benzyl phthalate, o-anisaldehyde, benzoin, succinic acid and toluic acid.
- Such carriers may be employed alone or in admixture with each other as well as with benzophenone and/or butyl benzoate. Normally, 10 to 25 weight percent of carrier, based on the weight of the fiber to be treated, produces satisfactory results.
- temperatures of dyeing about 180 F. up to about the boiling point of the aqueous dyebath, e.g., about 212 F., may be employed with temperatures in the range of 200 to 212 F. being preferred.
- Control of pH is very important and a pH range of between 2 and 5 must be employed to insure substantial dyebath exhaustion.
- Conventional acids used in dyebath formulations e.g., formic, acetic, sulphuric or phosphoric acid are preferably employed.
- Formic acid is most preferred because it offers the highest degree of exhaustion.
- the dyestuffs falling within the scope of this invention are the anionic dyes.
- Certain anionic dyes were found to be more satisfactory than others and among these are the direct dyes, e.g., Direct Red 81 (Cl. 28160), 2:1 premetallized azo dyes, e.g., Acid Red 201 (01. 18761) and Acid Red 180 (CL 8736) and azo or anthraquinone acid dyes.
- the azo and anthraquinone acid dyes the most preferred are the monosulfonated ones.
- the monosulfonated and monosulfonamides are most preferred.
- Dyes such as monosulfonated azo Acid Yellow 29 (CI. 18900), monosulfonated azo Acid Red 4 (CI. 14710) and monosulfonated anthraquinone Acid Blue 27 (CI. 61530) gave excellent color yield and, in most cases, were totally exhausted after 60 minutes at 212 F.
- dyes such as Acid Orange 45 (CI. 22195) Acid Red 73 (CI. 27290), Acid Blue 113 (CI. 26360) and Direct Yellow 44 (CI. 29000) gave poorer color yield and were far from total exhaustion.
- the latter dyes all have more than one acidic groups, i.e. sulfonic or carboxylic acid group, however, by use of the carriers and conditions of the present invention, even these dyestuffs produced dyeings unattainable by the prior art.
- anionic and nonionic wetting agents may be employed if desired.
- Anionic wetting agents are preferred.
- EXAMPLE 1 10 g. of Du Pont type 472 nylon fiber is immersed in a bath prepared as follows:
- the fiber is immersed in the dyebath and the dyebath is heated at 2-3 F./min. to the boil, i.e., about 212 F.
- the fiber is boiled for about one hour, washed with water and dried to achieve a deep, bright blue level dyeing. Fastness to wet and light conditions were outstanding.
- EXAMPLE 2 Proceeding substantially in the same manner as in Example 1, several organic chemicals were employed to determine their carrier effect. Several were found to give significant exhaustion and these are benzyl benzoate, phenyl benzoate, o-bromobenzoic acid, 2-chlorobenzoic acid, monobenzyl phthalate, o-anisaldehyde, benzoin, succinic acid, and toluic acid.
- R is the same or different member of the class consisting of hydrogen or methyl which comprises immersing said fiber in an aqueous dyebath containing (a) a carrier, benzophenone, in an amount effective to produce a level dyeing,
- an anionic dyestulf selected from the group consisting of azo and anthraquinone acid dyestuffs, 2:1 premetallized azo dyestuffs and direct dyestuffs,
- the pH of said dyebath being in the range of 2 to 5 and the temperature of said dyeing being from about F. to about 212 F.
Landscapes
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Coloring (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10251870A | 1970-12-29 | 1970-12-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3700405A true US3700405A (en) | 1972-10-24 |
Family
ID=22290284
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US102518A Expired - Lifetime US3700405A (en) | 1970-12-29 | 1970-12-29 | Dyeing of polycarbonamides of bis(paraamino-cyclohexyl)methane and dodecanediodic acid with anionic dyes |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US3700405A (enrdf_load_stackoverflow) |
| BE (1) | BE777360A (enrdf_load_stackoverflow) |
| CA (1) | CA970107A (enrdf_load_stackoverflow) |
| CH (2) | CH1843671A4 (enrdf_load_stackoverflow) |
| DE (1) | DE2165165B2 (enrdf_load_stackoverflow) |
| FR (1) | FR2120052B1 (enrdf_load_stackoverflow) |
| GB (1) | GB1367178A (enrdf_load_stackoverflow) |
| IT (1) | IT945673B (enrdf_load_stackoverflow) |
| NL (1) | NL7117989A (enrdf_load_stackoverflow) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4032291A (en) * | 1976-01-12 | 1977-06-28 | Ciba-Geigy Corporation | Phenyl phthalate carriers in dyeing and printing synthetic fibers |
| US4221566A (en) * | 1978-06-05 | 1980-09-09 | Velsicol Chemical Corporation | Dye compositions containing a combination of dye assistants which includes a mixture of lower alkyl esters of aromatic carboxylic acids |
| US4229178A (en) * | 1978-06-05 | 1980-10-21 | Velsicol Chemical Corporation | Dye compositions |
| US4238191A (en) * | 1979-11-26 | 1980-12-09 | Burlington Industries, Inc. | Bulking of polycarbonamides: qiana |
| US4308025A (en) * | 1979-11-26 | 1981-12-29 | Burlington Industries, Inc. | Simultaneous bulking and dyeing process |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB943147A (en) * | 1961-05-03 | 1963-11-27 | British Nylon Spinners Ltd | Improvements relating to the dyeing of high molecular weight polyamides |
| GB1096943A (en) * | 1964-05-06 | 1967-12-29 | Unilever Ltd | Solvent assisted dyeing |
| US3510891A (en) * | 1966-11-23 | 1970-05-12 | Du Pont | Dyeing polyamide fibers with pelargonic acid |
| DE1769997A1 (de) * | 1968-08-20 | 1971-11-11 | Hoechst Ag | Verfahren zum Faerben von Wolle und Mischungen aus Wolle mit Polyesterfasern |
-
1970
- 1970-12-29 US US102518A patent/US3700405A/en not_active Expired - Lifetime
-
1971
- 1971-12-17 CH CH1843671D patent/CH1843671A4/xx unknown
- 1971-12-17 CH CH1843671A patent/CH556941A/xx unknown
- 1971-12-28 IT IT55030/71A patent/IT945673B/it active
- 1971-12-28 DE DE2165165A patent/DE2165165B2/de active Granted
- 1971-12-28 FR FR7146934A patent/FR2120052B1/fr not_active Expired
- 1971-12-28 BE BE777360A patent/BE777360A/xx unknown
- 1971-12-28 NL NL7117989A patent/NL7117989A/xx not_active Application Discontinuation
- 1971-12-29 GB GB6050071A patent/GB1367178A/en not_active Expired
- 1971-12-29 CA CA131,218A patent/CA970107A/en not_active Expired
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4032291A (en) * | 1976-01-12 | 1977-06-28 | Ciba-Geigy Corporation | Phenyl phthalate carriers in dyeing and printing synthetic fibers |
| US4221566A (en) * | 1978-06-05 | 1980-09-09 | Velsicol Chemical Corporation | Dye compositions containing a combination of dye assistants which includes a mixture of lower alkyl esters of aromatic carboxylic acids |
| US4229178A (en) * | 1978-06-05 | 1980-10-21 | Velsicol Chemical Corporation | Dye compositions |
| US4238191A (en) * | 1979-11-26 | 1980-12-09 | Burlington Industries, Inc. | Bulking of polycarbonamides: qiana |
| US4308025A (en) * | 1979-11-26 | 1981-12-29 | Burlington Industries, Inc. | Simultaneous bulking and dyeing process |
Also Published As
| Publication number | Publication date |
|---|---|
| DE2165165A1 (de) | 1972-07-06 |
| DE2165165B2 (de) | 1974-05-16 |
| FR2120052B1 (enrdf_load_stackoverflow) | 1974-06-07 |
| CA970107A (en) | 1975-07-01 |
| CH1843671A4 (enrdf_load_stackoverflow) | 1974-06-14 |
| DE2165165C3 (enrdf_load_stackoverflow) | 1975-01-02 |
| IT945673B (it) | 1973-05-10 |
| GB1367178A (en) | 1974-09-18 |
| CH556941A (enrdf_load_stackoverflow) | 1974-12-13 |
| FR2120052A1 (enrdf_load_stackoverflow) | 1972-08-11 |
| NL7117989A (enrdf_load_stackoverflow) | 1972-07-03 |
| BE777360A (fr) | 1972-06-28 |
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