US3894841A - Process for the single-bath dyeing of unmodified polyolefin fibers with water-insoluble pigment dyestuffs - Google Patents
Process for the single-bath dyeing of unmodified polyolefin fibers with water-insoluble pigment dyestuffs Download PDFInfo
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- US3894841A US3894841A US336940A US33694073A US3894841A US 3894841 A US3894841 A US 3894841A US 336940 A US336940 A US 336940A US 33694073 A US33694073 A US 33694073A US 3894841 A US3894841 A US 3894841A
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- dyestuffs
- fibers
- dyeing
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- acid
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- 238000000034 method Methods 0.000 title claims abstract description 48
- 238000004043 dyeing Methods 0.000 title claims abstract description 37
- 239000000835 fiber Substances 0.000 title claims abstract description 36
- 230000008569 process Effects 0.000 title claims abstract description 29
- 239000000049 pigment Substances 0.000 title claims abstract description 20
- 229920000098 polyolefin Polymers 0.000 title abstract description 11
- 239000006185 dispersion Substances 0.000 claims abstract description 16
- 150000001875 compounds Chemical class 0.000 claims abstract description 9
- 239000002253 acid Substances 0.000 claims abstract description 8
- 125000000129 anionic group Chemical group 0.000 claims abstract description 8
- 150000002170 ethers Chemical class 0.000 claims abstract description 7
- 229920000151 polyglycol Polymers 0.000 claims abstract description 7
- 239000010695 polyglycol Substances 0.000 claims abstract description 7
- 239000000975 dye Substances 0.000 claims description 26
- -1 POLYPROPYLENE Polymers 0.000 claims description 10
- 238000010025 steaming Methods 0.000 claims description 10
- 239000004743 Polypropylene Substances 0.000 claims description 8
- 229920001155 polypropylene Polymers 0.000 claims description 8
- XUJLWPFSUCHPQL-UHFFFAOYSA-N 11-methyldodecan-1-ol Chemical compound CC(C)CCCCCCCCCCO XUJLWPFSUCHPQL-UHFFFAOYSA-N 0.000 claims description 7
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 7
- 239000003795 chemical substances by application Substances 0.000 claims description 7
- 230000000694 effects Effects 0.000 claims description 7
- 239000007795 chemical reaction product Substances 0.000 claims description 6
- 239000000084 colloidal system Substances 0.000 claims description 5
- 230000001681 protective effect Effects 0.000 claims description 5
- 235000013912 Ceratonia siliqua Nutrition 0.000 claims description 4
- 240000008886 Ceratonia siliqua Species 0.000 claims description 4
- 125000002091 cationic group Chemical group 0.000 claims description 4
- 235000013312 flour Nutrition 0.000 claims 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 claims description 3
- 150000004056 anthraquinones Chemical class 0.000 claims description 3
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 claims description 3
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical class N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 claims description 3
- 150000003856 quaternary ammonium compounds Chemical class 0.000 claims description 3
- 230000008719 thickening Effects 0.000 claims description 3
- 239000003513 alkali Substances 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 150000001340 alkali metals Chemical class 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- 239000000463 material Substances 0.000 abstract description 10
- 150000001767 cationic compounds Chemical class 0.000 abstract description 4
- 239000000126 substance Substances 0.000 abstract description 4
- 239000004753 textile Substances 0.000 abstract description 3
- 230000009471 action Effects 0.000 description 4
- 239000000047 product Substances 0.000 description 3
- FDRCDNZGSXJAFP-UHFFFAOYSA-M sodium chloroacetate Chemical compound [Na+].[O-]C(=O)CCl FDRCDNZGSXJAFP-UHFFFAOYSA-M 0.000 description 3
- RZSYLLSAWYUBPE-UHFFFAOYSA-L Fast green FCF Chemical compound [Na+].[Na+].C=1C=C(C(=C2C=CC(C=C2)=[N+](CC)CC=2C=C(C=CC=2)S([O-])(=O)=O)C=2C(=CC(O)=CC=2)S([O-])(=O)=O)C=CC=1N(CC)CC1=CC=CC(S([O-])(=O)=O)=C1 RZSYLLSAWYUBPE-UHFFFAOYSA-L 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 238000009792 diffusion process Methods 0.000 description 2
- FPVGTPBMTFTMRT-NSKUCRDLSA-L fast yellow Chemical compound [Na+].[Na+].C1=C(S([O-])(=O)=O)C(N)=CC=C1\N=N\C1=CC=C(S([O-])(=O)=O)C=C1 FPVGTPBMTFTMRT-NSKUCRDLSA-L 0.000 description 2
- 235000019233 fast yellow AB Nutrition 0.000 description 2
- 230000002209 hydrophobic effect Effects 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000009987 spinning Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 1
- JRBJSXQPQWSCCF-UHFFFAOYSA-N 3,3'-Dimethoxybenzidine Chemical compound C1=C(N)C(OC)=CC(C=2C=C(OC)C(N)=CC=2)=C1 JRBJSXQPQWSCCF-UHFFFAOYSA-N 0.000 description 1
- LPDSNGAFAJYVKH-UHFFFAOYSA-N 4-(4-aminophenyl)-2,3-dichloroaniline Chemical compound C1=CC(N)=CC=C1C1=CC=C(N)C(Cl)=C1Cl LPDSNGAFAJYVKH-UHFFFAOYSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- WLDHEUZGFKACJH-UHFFFAOYSA-K amaranth Chemical compound [Na+].[Na+].[Na+].C12=CC=C(S([O-])(=O)=O)C=C2C=C(S([O-])(=O)=O)C(O)=C1N=NC1=CC=C(S([O-])(=O)=O)C2=CC=CC=C12 WLDHEUZGFKACJH-UHFFFAOYSA-K 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000003931 anilides Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 150000008049 diazo compounds Chemical class 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 238000009967 direct dyeing Methods 0.000 description 1
- 239000000986 disperse dye Substances 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 239000002657 fibrous material Substances 0.000 description 1
- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 239000012860 organic pigment Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920001522 polyglycol ester Polymers 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 239000013589 supplement Substances 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
- D06P1/60—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 polyethers
- D06P1/613—Polyethers without nitrogen
- D06P1/6131—Addition products of hydroxyl groups-containing compounds with oxiranes
-
- 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
- D06P1/0048—Converting dyes in situ in a non-appropriate form by hydrolysis, saponification, reduction with split-off of a substituent
-
- 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
- D06P1/653—Nitrogen-free carboxylic acids or their salts
- D06P1/6533—Aliphatic, araliphatic or cycloaliphatic
-
- 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
- D06P3/79—Polyolefins
-
- 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
- Y10S8/903—Triple mixture of anionic, cationic, and nonionic emulsifiers for dyeing
-
- 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
- Y10S8/906—Mixed cationic and nonionic emulsifiers for dyeing
-
- 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
- Y10S8/907—Nonionic emulsifiers for dyeing
-
- 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
- Y10S8/908—Anionic emulsifiers for dyeing
Definitions
- ABSTRACT Process for the single-bath dyeing or printing of unmodified polyolefin fibers with water-insoluble pigment dyestuffs by reacting under high-temperature dyeing conditions on these textile materials aqueous liquors or printing pastes containing solutions of pigment dyestuffs reversibly solubilized by cationactive compounds and, optionally, strong alkalis, and substances splitting off acid under heat, or dispersions of the salt-like addition products of dyestuffs having anionic character with cationic compounds, in the presence of a dispersion system on the basis of polyglycol ethers.
- the present invention relates to a process for the singlebath dyeing of unmodified polyolefin fibers with water-insoluble pigment dyestuffs.
- unmodified polyolefin fibers for example, polypropylene fibers
- polypropylene fibers are, generally, difficult to dye by direct dyeing methods.
- the dyeing of piece goods made of such fibers with aqueous suspensions of pigment dyestuffs and curable binding systems is described which form a correspondingly coloured film layer fast to washing on the fiber surface when being heated.
- Disperse dyes used for dyeing polyester fibers and other hydrophobic fibers yield under comparable thermal conditions only very fair dyeings when being fixed the yield of which is unproportioned with respect to the amount of dyestuff used.
- polystyrene resin Various methods of the modification of the polyolefin material allow to improve the dye receptivity of the fiber considerably.
- nitrogen-containing copolymers having a basic effect are introduced into the spinning melt of the fibrous ground substance of which the fibers consist and so anchored in the macromolecule.
- the fibers so modified then have affinity towards the anionic dyestuffs.
- Polypropylene can also be modified in such a manner that compounds of such metals which can form fast colour lakes with metallizable dyestuffs are incorporated into the mass or fiber.
- the fiber properties are influenced either by a metal-containing copolymer or by special aftertreatment operations of the finished, unmodified fibrous material before dyeing, for example, as described in German AuslegeschriftenNos.
- unmodified polyolefin fibers preferably polypropylene fibers
- This invention is based on the observation that the solubilized pigment dyestuffs mentioned above have technically useful affinity towards the highly hydrophobic, unmodified polyolefin fibers when they are present in a special colloidal state of dispersion while concommittently using acid-yielding agents and a determined dispersion system and are applied under suitable thermal conditions. Under these conditions the dyeings or prints can be effected according to the present process using the exhaustion method, the pad-steaming method or a printing method together with steam fixation of the dyes.
- the temperatures required for this purpose in the case of the exhaustion method as well as of the padsteaming or print-steaming method are within the range of from C, preferably, however, about 130C.
- These temperatures comprise a technical safety zone between the range of temperature of C at which the polypropylene fiber softens.
- the times of action are with the exhaustion method 50 to 70 minutes, preferably 60 minutes, and with the pad-steaming or print-steaming method from 25 to 45 minutes, preferably 30 minutes.
- the dyestuffs to be used for carrying out the dyeings according to the new method are derived from waterinsoluble organic pigment dyestuffs, for example, azo, anthraquinone, phthalocyanine or similar pigments.
- waterinsoluble organic pigment dyestuffs for example, azo, anthraquinone, phthalocyanine or similar pigments.
- highly cationactive components for example, quaternary ammonium compounds, especially those of the type of alkyldimethylbenzyl-ammonium chloride, optionally in the presence of strong alkalis.
- the dyestuffs hereinbefore mentioned have a marked affinity towards the surface of the fiber already at the beginning of the dyeing process because of their cationactive component.
- the dyestuff is thus concentrated at the surface where the diffusion of the pigment into the fiber occurs under high-temperature dyeing conditions.
- This dispersion system mainly consists of a non-ionic auxiliary on the basis of alkylor alkylaryl-polyglycol ethers or oxethylated fatty acid polyglycol esters, preferably a reaction product of 1 mol of isotridecyl alcohol with 8 mols of ethylene oxide, which is combined in the case of the exhaustion method optionally with anionic protective colloids having a dispersing effect, preferably those on the basis of lignin-sulfonic acid, and in the case of the pad-steaming or print-steaming method with non-ionic protective colloids having a thickening effect, preferably of the type of a completely etherified
- dyeings could also be obtained on unmodified polyolefin fibers (under analogous dyeing conditions in the high temperature range) also with combinations of any anionic, water-soluble or dispersed dyestuff, for example, acid dyestuffs, with strongly cationic auxiliaries, for example, of the type of alkyl-dimethyl-benzyl-ammonium chloride, its derivatives, mixtures or other surface-active quaternary fatty amines.
- any anionic, water-soluble or dispersed dyestuff for example, acid dyestuffs
- strongly cationic auxiliaries for example, of the type of alkyl-dimethyl-benzyl-ammonium chloride, its derivatives, mixtures or other surface-active quaternary fatty amines.
- Those cationic products produce with anionic dyestuffs precipitations.
- suitable dispersing agents for example, oxethylated fatty alcohols
- the cationic precipitating agent can develop, when being in excess, such a dispersing effect.
- Example 1 1 percent of the azo pigment indicated in Example 1 1 percent of the copper phthalocyanine dyestuff indicated in Example 2 both dyestuffs being dissolved according to the methods described in the literature indicated above.
- the material so treated was dried at C, steamed at C for 30 minutes in a pressure steamer and rinsed and finished in the usual manner.
- a process for the single-bath dyeing or printing of unmodified polypropylene fibers with water-insoluble pigment dyestuffs which comprises: treating said fibers, under high temperature dyeing conditions above 120C, with aqueous liquors or printing pastes containl. a pigment dyestuff which is reversibly solubilized by a cation-active quaternary ammonium compound and strong alkali,
- nonionic auxiliaries based upon the reaction product of 1 mol of isotridecyl alcohol with 8 mols of ethylene oxide are used in combination with non-ionic protective colloids having a thickening effect of the type of a completely etherified locust bean flour.
Abstract
Process for the single-bath dyeing or printing of unmodified polyolefin fibers with water-insoluble pigment dyestuffs by reacting under high-temperature dyeing conditions on these textile materials aqueous liquors or printing pastes containing solutions of pigment dyestuffs reversibly solubilized by cationactive compounds and, optionally, strong alkalis, and substances splitting off acid under heat, or dispersions of the salt-like addition products of dyestuffs having anionic character with cationic compounds, in the presence of a dispersion system on the basis of polyglycol ethers.
Description
United States Patent von der Eltz et a1.
[451 July 15,1975
[ PROCESS FOR THE SINGLE-BATH DYEING OF UNMODIFIED POLYOLEFIN FIBERS WITH WATER-INSOLUBLE PIGMENT DYESTUFFS [75] Inventors: Hans-Ulrich von der Eltz, Frankfurt am Main; Armand Lehinant, Offenbach, Main; Hans-Peter Maier, Sulzbach, Taunus, all of Germany [73] Assignee: Hoechst Aktiengesellschaft,
Frankfurt am Main, Germany [22] Filed: Mar. 1, 1973 [21] Appl. No.: 336,940
[30] Foreign Application Priority Data Mar. 7, 1972 Germany 2210880 [52] US. Cl. 8/169; 8/172; 8/176;
[51] Int. Cl D06p 5/04 [58] Field of Search 8/169, 172, 176, 180
[56] References Cited UNITED STATES PATENTS 3,097.044 7/1963 Skeuse 8/42 OTHER PUBLICATIONS Cook, Handbook of Polyolefin Fibres, (1967), Merrow Publishing Co. Ltd. pp. 139-141, TS1548.5
Primary Examiner-Leland A. Sebastian Assistant Examiner-B. H. Hunt Attorney, Agent, or Firm-Curtis, Morris & Safford [57] ABSTRACT Process for the single-bath dyeing or printing of unmodified polyolefin fibers with water-insoluble pigment dyestuffs by reacting under high-temperature dyeing conditions on these textile materials aqueous liquors or printing pastes containing solutions of pigment dyestuffs reversibly solubilized by cationactive compounds and, optionally, strong alkalis, and substances splitting off acid under heat, or dispersions of the salt-like addition products of dyestuffs having anionic character with cationic compounds, in the presence of a dispersion system on the basis of polyglycol ethers.
8 Claims, No Drawings PROCESS FOR THE SINGLE-BATH DYEING OF UNMODIFIED POLYOLEFINFIBERS WITH WATER-INSOLUBLE PIGMENT DYESTUFFS The present invention relates to a process for the singlebath dyeing of unmodified polyolefin fibers with water-insoluble pigment dyestuffs.
It is known that unmodified polyolefin fibers, for example, polypropylene fibers, are, generally, difficult to dye by direct dyeing methods. Besides the immediate dyeing of the spinning mass in the melt with pigment dyestuffs, the dyeing of piece goods made of such fibers with aqueous suspensions of pigment dyestuffs and curable binding systems is described which form a correspondingly coloured film layer fast to washing on the fiber surface when being heated. Disperse dyes used for dyeing polyester fibers and other hydrophobic fibers, however, yield under comparable thermal conditions only very fair dyeings when being fixed the yield of which is unproportioned with respect to the amount of dyestuff used.
Various methods of the modification of the polyolefin material allow to improve the dye receptivity of the fiber considerably. For example, nitrogen-containing copolymers having a basic effect are introduced into the spinning melt of the fibrous ground substance of which the fibers consist and so anchored in the macromolecule. The fibers so modified then have affinity towards the anionic dyestuffs. Polypropylene can also be modified in such a manner that compounds of such metals which can form fast colour lakes with metallizable dyestuffs are incorporated into the mass or fiber. Thus, the fiber properties are influenced either by a metal-containing copolymer or by special aftertreatment operations of the finished, unmodified fibrous material before dyeing, for example, as described in German AuslegeschriftenNos. 1,297,577, 1,469,600 and 1,619,601. But each of these processes for the modification of polyolefins requires additional operational expenditure which makes the fiber more expensive and sometimes inadvertantly affects the physical properties of the fiber, for example, by reducing its stability and elasticity or by increasing its inflammability.
It was now, found, that unmodified polyolefin fibers, preferably polypropylene fibers, can be dyed or printed in a single-bath operation with water-insoluble pigment dyes when allowing to act, under high temperature dyeing conditions, on these textile materials aqueous liquors or printing pastes containing solutions of pigment dyestuffs reversibly solubilized by cation-active compounds and, optionally, strong alkalis, and substances splitting off acid under the action of heat, or dispersions of the salt-like addition products of dyestuffs having anionic character with cationic compounds, in the presence of a dispersion system on the basis of polyglycol ethers.
This invention is based on the observation that the solubilized pigment dyestuffs mentioned above have technically useful affinity towards the highly hydrophobic, unmodified polyolefin fibers when they are present in a special colloidal state of dispersion while concommittently using acid-yielding agents and a determined dispersion system and are applied under suitable thermal conditions. Under these conditions the dyeings or prints can be effected according to the present process using the exhaustion method, the pad-steaming method or a printing method together with steam fixation of the dyes. The temperatures required for this purpose in the case of the exhaustion method as well as of the padsteaming or print-steaming method are within the range of from C, preferably, however, about 130C. These temperatures comprise a technical safety zone between the range of temperature of C at which the polypropylene fiber softens. The times of action are with the exhaustion method 50 to 70 minutes, preferably 60 minutes, and with the pad-steaming or print-steaming method from 25 to 45 minutes, preferably 30 minutes.
The dyestuffs to be used for carrying out the dyeings according to the new method are derived from waterinsoluble organic pigment dyestuffs, for example, azo, anthraquinone, phthalocyanine or similar pigments. According to the processes described in German Patents Nos. 1,265,700, l,269,587, 1,297,071 and 1,297,073 they are made reversibly water-soluble by means of highly cationactive components, for example, quaternary ammonium compounds, especially those of the type of alkyldimethylbenzyl-ammonium chloride, optionally in the presence of strong alkalis. The dyestuffs hereinbefore mentioned have a marked affinity towards the surface of the fiber already at the beginning of the dyeing process because of their cationactive component. The dyestuff is thus concentrated at the surface where the diffusion of the pigment into the fiber occurs under high-temperature dyeing conditions.
To carry out the process of the invention it is essential that the dissolved dyestuff, when being reprecipitated, is suitably distributed under the action of acid-yielding agents. The dyestuff can so diffuse into and be absorbed by the fiber which is, at best, achieved by means of a mixture of auxiliaries, This dispersion system mainly consists of a non-ionic auxiliary on the basis of alkylor alkylaryl-polyglycol ethers or oxethylated fatty acid polyglycol esters, preferably a reaction product of 1 mol of isotridecyl alcohol with 8 mols of ethylene oxide, which is combined in the case of the exhaustion method optionally with anionic protective colloids having a dispersing effect, preferably those on the basis of lignin-sulfonic acid, and in the case of the pad-steaming or print-steaming method with non-ionic protective colloids having a thickening effect, preferably of the type of a completely etherified locust bean flour.
When performing the process of the invention it could not be expected that the use of acid-yielding agents which are only active at higher temperatures, for example, of the type of monohalogenated acetates of alkali metals, preferably sodium monochloro-acetate, increases the color yield to such a considerable degree that it can be considered as a prerequisite for an economic operation of the process of the invention. By lowering the pH under the action of the acidyielding agent the cationic compound which is only loosely bound is split off and the dyestuff is converted from the dissolved into the dispersed form.
When performing the process of the invention it was also found that dyeings could also be obtained on unmodified polyolefin fibers (under analogous dyeing conditions in the high temperature range) also with combinations of any anionic, water-soluble or dispersed dyestuff, for example, acid dyestuffs, with strongly cationic auxiliaries, for example, of the type of alkyl-dimethyl-benzyl-ammonium chloride, its derivatives, mixtures or other surface-active quaternary fatty amines.
Those cationic products produce with anionic dyestuffs precipitations. When using suitable dispersing agents, for example, oxethylated fatty alcohols, it is possible to maintain these salt-like addition compounds in such a finely colloidal state of dispersion that a diffusion in the fiber under high-temperature dyeing conditions and thus, staining of the material is possible. The cationic precipitating agent can develop, when being in excess, such a dispersing effect.
The following Examples illustrate the invention. The Colour-Index numbers indicated in the Examples to characterize the dyestuffs have been taken from the second edition 1956 and from the supplement volume 1963.
EXAMPLE 1 Loose material of unmodified polypropylene fibers was dyed in a high-temperature dyeing apparatus, with a goods-to-liquor ratio of 1:20 for 60 minutes with an aqueous liquid of 130C which contained, calculated on the weight of the dry material, the following constituents:
2 percent of the azo dyestuff Pigment Yellow 12 C.l. No. 21,090, dissolved according to the process described in German Patent No. 1,265,700,
2 percent of sodium monochloroacetate and 1 percent of the reaction product of 1 mol of isotridecyl alcohol with 8 mols of ethylene oxide.
Then, the material so treated was rinsed with warm and cold water and finished in the usual manner.
A brilliant, fast yellow dyeing was obtained the colour intensity of which corresponded to the amount of dyestuff used.
EXAMPLE 2 Dyeing was carried out in an analogous manner as described in Example 1 while using, however,
2 percent of the dyestuff copper-phthalocyaninetrisulfonic acid anilide dissolved according to the process described in German Patent No. 1,269,587.
A brilliant, blue dyeing fast to light and to washing was obtained.
EXAMPLE 3 Dyeing was carried out in an analogous manner as described in Example l while using, however,
1 percent of the azo pigment indicated in Example 1 1 percent of the copper phthalocyanine dyestuff indicated in Example 2 both dyestuffs being dissolved according to the methods described in the literature indicated above.
A brilliant, fast green dyeing was obtained.
EXAMPLE 4 Dyeing was carried out in an analogous manner as described in Example 1 while using, howver,
2 percent of an azo dyestuff obtained by coupling 2 mols of a-phenyl-3-methyl-5-pyrazolone with the diazo compounds of 0.3 mol of dianisidine and 0.7 mol of dichlorobenzidine, which was made soluble according to the process described in German Patent No. 1,265,700.
A brilliant, fast red dyeing was obtained.
EXAMPLE 5 Piece-goods of unmodified polypropylene fibers were padded, with a liquor-pick-up of by weight, with a cold liquid which contained per liter of water the following constituents:
16 g of the dyestuff indicated in Example 1 and dissolved as described hereinbefore,
5 g of the reaction product of 1 mol of isotridecyl alcohol with 8 mols of ethylene oxide,
10 g of a 2 aqueous solution of a completely etherified locust bean flour and 10 g of sodium monochloroacetate.
After having applied the dyestuff the material so treated was dried at C, steamed at C for 30 minutes in a pressure steamer and rinsed and finished in the usual manner.
A brilliant, fast yellow dyeing was obtained the colour depth of which corresponded to the amount of dyestuff used. 7
When proceding by this method prints can also be effected on the material.
EXAMPLE 6 Dyeing was carried out, in an analogous manner as described in Example 5 while using, however, a pad ding liquor which contained instead of the dyestuff mentioned in this Example 10 g/l of the dyestuff indicated in Example 1 and 10 g/l of the dyestuff indicated in Example 2.
A brilliant fast green dyeing was obtained.
EXAMPLE 7 Dyeing was carried out as described in Example 5 while using, however, a padding liquor which contained in addition to the auxiliaries mentioned therein 4 g/l of the dyestuff indicated in Example 1,
5 g/l of the dyestuff indicated in Example 2 and 8 g/l of the dyestuff indicated in Example 4.
A fast brown dyeing was obtained.
We claim:
1. A process for the single-bath dyeing or printing of unmodified polypropylene fibers with water-insoluble pigment dyestuffs, which comprises: treating said fibers, under high temperature dyeing conditions above 120C, with aqueous liquors or printing pastes containl. a pigment dyestuff which is reversibly solubilized by a cation-active quaternary ammonium compound and strong alkali,
2. a compound which yields acid at temperatures above 100C, and
3. a dispersion system based upon polyglycol ethers or esters. 1
2. A process as claimed in claim 1, wherein the dyestuffs are applied on the fibers according to the exhaustion method for 50 to 70 minutes at a temperature from 120C to C.
3. A process as claimed in claim 1, wherein the dyestuffs are padded or printed onto the fibers and these paddings or prints are steamed in a pressure steamer at l20 135C for 20 to 45 minutes.
4. A process as claimed in claim 1, wherein dyestuffs of the azo, anthraquinone or phthalocyanine series are used.
6 mol of isotridecyl alcohol with 8 mols of ethylene oxide.
8. A process as claimed in claim 3, wherein as dispersion system for the pad-steaming or print-steaming method, nonionic auxiliaries based upon the reaction product of 1 mol of isotridecyl alcohol with 8 mols of ethylene oxide are used in combination with non-ionic protective colloids having a thickening effect of the type of a completely etherified locust bean flour.
Claims (13)
1. A PROCESS FOR THE SINGLE-BATH DYEING OR PRINTING OF UNMODIFIED POLYPROPYLENE FIBERS WITH WATER-INSOLUBLE PIGMENT DYESTUFFS, WHICH COMPRISES: TREATING SAID FIBERS, UNDER HIGH TEMPERATURE DYEING CONDITIONS ABOVE 120*C, WITH AQUEOUS LIQUORS OR PRINTING PASTES CONTAINING,
1. A PIGMENT DYESTUFF WHICH IS REVERSIBLY SOLUBILIZED BY A CATION-ACTIVE QUATERNARY AMMONIUM COMPOUND AND STRONG ALKALI,
2. A COMPOUND WHICH YIELDS ACID AT TEMPERATURES ABOVE 100*C, AND
2. A process as claimed in claim 1, wherein the dyestuffs are applied on the fibers according to the exhaustion method for 50 to 70 minutes at a temperature from 120*C to 135*C.
2. a compound which yields acid at temperatures above 100*C, and
3. a dispersion system based upon polyglycol ethers or esters.
3. A process as claimed in claim 1, wherein the dyestuffs are padded or printed onto the fibers and these paddings or prints are steamed in a pressure steamer at 120* - 135*C for 20 to 45 minutes.
3. A DISPERSION SYSTEM BASED UPON POLYGLYCOL ETHERS OR ESTERS.
4. A process as claimed in claim 1, wherein dyestuffs of the azo, anthraquinone or phthalocyanine series are used.
5. A process as claimed in claim 1, wherein as acid-yielding agent monohaloacetates of alkali metals are used.
6. A process as claimed in claim 1, wherein as cationic quaternary compound, an alkyl-dimethyl-benzyl-ammonium chloride is used.
7. A process as claimed in claim 2, wherein as dispersion system for the exhaustion method, anionic protective colloids having a dispersing effect based upon lignin-sulfonic acid are used in combination with a non-ionic auxiliary based upon the reaction product of 1 mol of isotridecyl alcohol with 8 mols of ethylene oxide.
8. A process as claimed in claim 3, wherein as dispersion system for the pad-steaming or print-steaming method, nonionic auxiliaries based upon the reaction product of 1 mol of isotridecyl alcohol with 8 mols of ethylene oxide are used in combination with non-ionic protective colloids having a thickening effect of the type of a completely etherified locust bean flour.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE2210880A DE2210880C3 (en) | 1972-03-07 | 1972-03-07 | Process for the one-bath dyeing of unmodified polyolefin fibers with water-insoluble pigment dyes |
Publications (1)
Publication Number | Publication Date |
---|---|
US3894841A true US3894841A (en) | 1975-07-15 |
Family
ID=5838144
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US336940A Expired - Lifetime US3894841A (en) | 1972-03-07 | 1973-03-01 | Process for the single-bath dyeing of unmodified polyolefin fibers with water-insoluble pigment dyestuffs |
Country Status (5)
Country | Link |
---|---|
US (1) | US3894841A (en) |
JP (1) | JPS4899468A (en) |
CH (2) | CH573510B5 (en) |
DE (1) | DE2210880C3 (en) |
IT (1) | IT981127B (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2009153642A1 (en) * | 2008-06-18 | 2009-12-23 | Marco Goretti | Process for colouring elements made of polymeric material, in particular yarns selectively produced in polyethylene (pe), in ultra high molecular weight polyethylene (uhmw-pe) and derivatives thereof such as hshm-pe |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
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RU2289045C2 (en) | 2001-04-26 | 2006-12-10 | МОУШН ТЕКНОЛОДЖИЗ, ЛЛСи | Infinitely variable gear box |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3097044A (en) * | 1960-04-04 | 1963-07-09 | Geigy Chem Corp | Process for coloring polypropylene |
US3171710A (en) * | 1962-02-28 | 1965-03-02 | Ici Ltd | Process for the dyeing of stereoregular polypropylene textile materials with aqueousdispersions containing waterinsoluble dyestuffs |
US3233960A (en) * | 1966-02-08 | Dyeing and printing of polyolefins | ||
US3362781A (en) * | 1964-05-15 | 1968-01-09 | Kuhlmann Ets | 7-(2', 5'-dichlorophenylazo)-6-methyl-8-hydroxy-quinoline dyeing of metallized polyolefin fibers |
US3556709A (en) * | 1964-05-15 | 1971-01-19 | Ugine Kuhlmann | Polyolefin fiber dyeing with an arylazo 8-hydroxy-quinoline-5-sulfonic acid and fibers so dyed |
-
1972
- 1972-03-07 DE DE2210880A patent/DE2210880C3/en not_active Expired
-
1973
- 1973-03-01 US US336940A patent/US3894841A/en not_active Expired - Lifetime
- 1973-03-02 CH CH314873A patent/CH573510B5/xx not_active IP Right Cessation
- 1973-03-02 CH CH314873D patent/CH314873A4/xx unknown
- 1973-03-05 IT IT21195/73A patent/IT981127B/en active
- 1973-03-05 JP JP48025243A patent/JPS4899468A/ja active Pending
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3233960A (en) * | 1966-02-08 | Dyeing and printing of polyolefins | ||
US3097044A (en) * | 1960-04-04 | 1963-07-09 | Geigy Chem Corp | Process for coloring polypropylene |
US3171710A (en) * | 1962-02-28 | 1965-03-02 | Ici Ltd | Process for the dyeing of stereoregular polypropylene textile materials with aqueousdispersions containing waterinsoluble dyestuffs |
US3362781A (en) * | 1964-05-15 | 1968-01-09 | Kuhlmann Ets | 7-(2', 5'-dichlorophenylazo)-6-methyl-8-hydroxy-quinoline dyeing of metallized polyolefin fibers |
US3556709A (en) * | 1964-05-15 | 1971-01-19 | Ugine Kuhlmann | Polyolefin fiber dyeing with an arylazo 8-hydroxy-quinoline-5-sulfonic acid and fibers so dyed |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2009153642A1 (en) * | 2008-06-18 | 2009-12-23 | Marco Goretti | Process for colouring elements made of polymeric material, in particular yarns selectively produced in polyethylene (pe), in ultra high molecular weight polyethylene (uhmw-pe) and derivatives thereof such as hshm-pe |
Also Published As
Publication number | Publication date |
---|---|
CH573510B5 (en) | 1976-03-15 |
DE2210880A1 (en) | 1973-09-20 |
IT981127B (en) | 1974-10-10 |
JPS4899468A (en) | 1973-12-15 |
CH314873A4 (en) | 1975-09-15 |
DE2210880B2 (en) | 1977-10-13 |
DE2210880C3 (en) | 1978-06-15 |
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