GB2247470A - N-Alkylphthalimide mixtures for use as carriers in dyeing and optical brightening - Google Patents
N-Alkylphthalimide mixtures for use as carriers in dyeing and optical brightening Download PDFInfo
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- GB2247470A GB2247470A GB9118129A GB9118129A GB2247470A GB 2247470 A GB2247470 A GB 2247470A GB 9118129 A GB9118129 A GB 9118129A GB 9118129 A GB9118129 A GB 9118129A GB 2247470 A GB2247470 A GB 2247470A
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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
- D06P1/64—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
- D06P1/642—Compounds containing nitrogen
- D06P1/649—Compounds containing carbonamide, thiocarbonamide or guanyl groups
- D06P1/6495—Compounds containing carbonamide -RCON= (R=H or hydrocarbons)
- D06P1/6498—Compounds containing -CONCO-, e.g. phthalimides, hydantoine; Compounds containing RCONHSO2R (R=H or hydrocarbon)
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Abstract
N-alkylphthalimide mixtures (P) of (a) N-(n-propyl)-phthalimide (b) N-(sec.-C4-6-alkyl)-phthalimide and (c) N-(n-C4-6-alkyl)-phthalimide wherein the weight ratio (a)/(P) is in the range of 3/100 to 14/100, in particular in admixture with an emulsifier system (E), are suitable as stable, readily emulsifiable compositions, in particular as carriers in the application of disperse dyes or optical brighteners to (semi)synthetic fibrous substrates, e.g. polyamide, polyester, cellulose acetate. The compositions may also be used in aqueous printing pastes and inks.
Description
k IMPROVEMENTS IN OR RELATING TO ORGANIC COMPOUNDS Low molecular
N-alkylphthalimides are useful as carriers in the dyeing or optical brightening of fibrous material with disperse dyes respectively disperse optical brighteners and are advantageously employed in the form of liquid compositions emulsifiable in water. For shipment and storage of such compositions their stability under various temperature conditions is of great significance. For their application it is desired that the content of active subtance in relation to any emulsifiers in the composition be as high as possible.
It has now been found that certain N-alkylphthalimide mixtures, as defined below, and which, in particular, are free of other (i.e. of lower and of higher as well as of differently branched) N-alkylphthalimides are surprisingly well emulsifiable, there being obtainable therewith compositions that remain stable in a very broad temperature range and that are distinguished by their outstanding efficiency as carriers.
The invention relates to the N-alkylphthalimide mixtures defined below, compositions containing such mixtures and their use as carriers.
The invention thus provides an N-alkylphthalimide mixture (P) consisting essentially of:
(a) N-(n-propyl)-phthalimide (b) N-(sec.-C4-6-alkyl)-phthalimide and (c) N-(n-C4-6-alkyl)-phthalimide wherein the weight ratio (a)/(P) is in the range of 3/100 to 14/100.
As components (b) come principally into consideration N-(butyl-2)phthalimide, N-(pentyl-2)-phthalimide and N-(hexyl-2)-phthalimide, among which N-(butyl-2)-phthalimide is preferred.
I- Case 150-5454 As components (c) come into consideration N-(n-hexyl)-phthalimide, N-(n- pentyl)-phthalimide and N-(n-butyl)-phthalimide among which the latter are preferred, in particular N-(n-butyl)-phthalimide.
The weight ratio (a)/(P) is advantageously in the range of 3/100 to 12/100, in particular 5/100 to 111100.
The weight ratio (b)/(c) is advantageously in the range of 1/10 to 411, preferably below 23/1, more preferably below 1/1, in particular in the range of 1/4 to 1/1.3.
The weight ratio (b)/(P) is advantageously in the range of 8/100 to 70/100, preferably 15/100 to 421100, most preferably 17/100 to 42/100.
The weight ratio (c)/(P) is advantageously in the range of 55/100 to 80/100, preferably 551100 to 72/100.
These mixtures (P) may be produced by admixing the single components with each other or also by synthesis of the imides in the presence of each other in a manner known per se, e.g. starting from phthalic acid anhydride or phthalic acid esters and the corresponding amines.
The phthalimides may optionally contain, e.g. due to an incomplete reaction and/or to any secondary reactions, minor portions of carboxy groups and/or (when starting from phthalic acid anhydride) optionally nonreacted anhydride, mainly 5 mole%, in particular < 2 mole% of the total of the imides. The phthalimides indicated above as (a), (b) and (c) include any such secondary products.
The mixtures (P) are, in particular, free of lower or higher Nalkylphthalimides as well as of differently branched N-alkylphthalimides. A content of up to 2 % by weight, preferably < 1 % by weight of lower and/or higher N-alkylphthalimides and/or of up to 5 % by weight, preferably < 2.5 % by weight, in particular < 1 % by weight, of differently branched N-alkylphthalimides in each of (a), (b) and (c), eventually deriving from impurities in the respective starting materials, may still be tolerated and is comprised in the definitions of (a), (b) and (c).
1 W 1 Case 150-5454 The mixtures (P) of the invention find their use as carriers. For this purpose they are advantageously combined with an emulsifier system (E), in order to facilitate their distribution in water in emulsified form. The invention thus further provides compositions (U) comprising (P) and (E) but which are free of other phthalimides.
As emulsifier systems (E) are suitable in general emulsifiers (e) which are preferably at least in part anionic and are optionally combined with emulsifying assistants (h).
The emulsifier system (E) comprises preferably at least one emulsifier (e); (e) preferably is (ei) at least one anionic emulsifier optionally in admixture with (e2) at least one non-ionic emulsifier.
As (el) come, in general, into consideration any anionic emulsifiers, e.g. as named in the German Patent DE 29 41 763 C2 (a USP 4 252 534) under (b) or as described in the patents DE 23 06 104 C3 (a USP 3 874 891), DE 32 46 383 C2 (a USP 4 516 979) and DE 32 47 400 C2 (a USP 4 464 180), al of which are incorporated herein by reference.
Preferably (el) is (ell) an at least partially carboxymethylated, phosphated or sulphated polyalkyleneglycolether of a hydrocarbon-mono- or -polyolcontaining on average at least 10 carbon atoms per hydroxy group of the mono or polyolp (e12) a sulphate, phosphate or carboxymethylated derivative of a sorbitan or glycerine fatty acid ester, wherein the fatty radical contains 12 to 24 carbon atoms or of a polyalkyleneglycolether thereof, or (e13) a C12-24-hydrocarbon sulphonic acid, Case 150-5454 the carboxy, phosphate or sulpho groups optionally being in salt form, or a mixture of such surfactants.
As (e2) come, in general, into consideration any non-ionic emulsifiers, e. g. oxyalkylation products as named in German Patent DE 29 41 763 C2 (a USP 4 252 534) under (e) or also oxyalkylation products of higher molecular polyols, in particular oxyalkylated novolakes or mixed novolakes as are described, e.g. in German Patents DE 23 06 104 C3 (=- USP 3 874 891), DE 32 46 383 C2 (=- USP 4 516 979) and DE 32 47 400 C2 (E USP 4 464 180) as intermediate products. All these patents are incorporated herein by reference.
Preferably (e2) is (e2l) a polyalkyleneglycolether of a hydrocarbon-monoor -polyol, containing on average at least 10 carbon atoms per hydroxy group of the mono- or polyol or (e22) a sorbitan or glycerine fatty acid ester, in which the fatty radical contains 12 to 24 carbon atoms, or a polyalkyleneglycolether thereof or a mixture of such surfactants.
The polyalkyleneglycolethers in (ell), (e2l), (el2) and (e22) are advantageously polyethyleneglycolethers, which may optionally comprise a minor proportion of propyleneoxy units and/or styreneoxy units; preferably the polyalkyleneglycolethers are exclusively polyethyleneglycolethers.
As (e21) there may be mentioned, in particular, the following polyalkyleneglycolethers:
(e2ll) polyalkyleneglycolethers of fatty alcohols with 12 to 24 carbon atoms, (e212) polyalkyleneglycolethers of mono- or dialkylphenols with 12 to 24, 1 1 Case 150-5454 preferably 14 to 18 carbon atoms in the mono- or dialkylphenyl radical and (e213) polyalkyleneglycolethers of simple or oligomeric methylene bridge-containing novolake condensates of mono- or dialkylphenols, that contain each 10 to 24, preferably 12 to 18 carbon atoms per molecule of mono- or dialkylphenol and optionally lower alkyl phenols (e.g. cresols) with formaldehyde.
The degree of oxyethylation is advantageously in the range of 4 to 50, preferably 4 to 20 moles of ethyleneoxide per val of alkylphenol and/or fatty alcohol.
As (e22) come, in particular, into consideration the following:
(e221) mono- or diesters of sorbitan or glycerine, wherein the esterforming fatty acid radicals may be saturated or also unsaturated, in particular monoethylenically unsaturated (e.g. lauroyl, palmitoyl, myristoyl, oleoyl, stearoyl or arachidoyl), principally sorbitan monooleate, sorbitan monostearate, sorbitan monolaurate and partially hydrolyzed fatty acid triglycerides, (e222) polyethyleneglycolethers of (e221) with 4 to 40 ethyleneoxy units, on average, per hydroxy group of the starting material, and (e223) polyethylenglycolethers of ricinol group-containing fatty acid glycerides, in particular triglycerides, preferably addition products of 8 to 50 moles of ethyleneoxide to 1 mole of ricinol group-containing triglyceride.
As (ell) come preferably into consideration the carboxymethylated, phosphated or sulphated derivatives of the corresponding surfactants named under (e21) above, in particular of (e211), (e212) and (e213).
As (e12) come preferably into consideration the corresponding sulphated, phosphated or carboxymethylated derivatives of the products named under Ir ' (e22), in particular of (e221), (e222) and (e223), Case 150-5454 As (e13) come preferably into consideration alkylbenzenesulphonic acids, principally dodecylbenzene sulphonic acid.
Among the carboxymethylated, phosphated or sulphated derivatives in (ell) and (e12) the sulphates are preferred.
The carboxy, sulpho and phosphato groups may be in the form of the free acids or their salts, in particular as -COOM, -S03M respectively -OP03M2, wherein M signifies hydrogen or a cation, preferably an alkali metal cation (in particular lithium, sodium or potassium), an equivalent of an alkaline earth metal cation (in particular magnesium or calcium) or an ammonium cation [in particular unsubstituted ammonium, mono-, di- or tri(C2-3-alkanol)ammonium or C3-6-alkylammonium]. In the preferred sulphates M is preferably NH4+.
The weight ratio (e2)/(el) advantageously is in the range of from 0/100 to 90/10, preferably 0/100 to 40/60. Where (e22) and/or a polyalkylene glycol ether of the monoalcohol (e2l) are employed in admixture with (elD. (el2) or a carboxymethylated, phosphated or sulphated polyalkyleneglycolether of a monoalcohol (ell), the weight ratio (eW(el) is advantageously in the range of 20/80 to 90/10.
According to a preferred feature of the invention there are employed such surfactants (e) which are obtainable by sulphating, phosphating or carboxymethylating the mentioned polyalkyleneglycolethers of the polyols, in particular of the novolake kind condensates as indicated above under (e213), preferably only in part, in particular to 10 to 70 mole%, most preferably to 12 to 25 mole%. These partially anionically modified derivatives of the products (e213) are indicatd in the following as (e3). The particularly preferred addition products of 4 to 20 moles of ethyleneoxide to 1 val of oligomeric, methylene bridge-containing condensation product of alkylphenol and formaldehyde, sulphated to 12 to 25 mole% are indicatd in the following as (e31).
Where as (e), (e3) or (e31) there are employed corresponding partially anionically modified polyalkyleneglycolethers of hydrocarbon polyols, in Case 150-5454 particular of oligomeric condensates as described above, these are advantageously such as shown in German Patents DE 23 06 104 C3 (z USP 3 874 891), DE 32 46 383 C2 (a USP 4 516 979) and DE 32 47 400 C2 (a USP 4 464 180), with the respective formulae-(I) therein and as described in their examples, whereby the partially anionically modified products - in particular (e31) - due to the statistical distribution of the anionic groups may optionally be present in admixture with nonanionically modified starting material (e213).
The emulsifier system (E) respectively the composition (U) of the invention, advantageously contains, along with emulsifier (e) respectively along with (P) + (e), (h) at least one lipophilic, non-ionic emulsifying assistant.
As (h) come advantageously into consideration oil-soluble polar products, preferably oil-soluble fatty acid-(C1-4-alkyl)esters with 12 to 24 carbon atoms, in the fatty acid radical or a mixture of such esters. As fatty acid radicals in these esters come in particular into consideration those mentioned above, as well as acyl radicals of technical fatty acids, in particular of tallow fatty acid, of technical oleic acid, of coconut fatty acid or of fish-oil acids or refined technical fatty acids, preferably such with 16 to 24 carbon atoms. As ester-forming Cl-4-alkyl radicals in (h) the lower molecular ones are preferred, in particular ethyl and, before all, methyl.
The emulsifier system (E) may consist of (e) alone or preferably of a mixture of (e) with (h); where (h) is present, the weight ratio (e)/(h) is advantageously in the range of 9515 to 40/60, preferably 80/20 to 40/60.
The weight ratio (E)/[(P) + (E)] is advantageously in the range of 3/100 to 20/100, preferably 51100 to 20/100. If (E) resp. the composition (U) of the invention contains no (h) the weight ratio of (e) to the total composition advantageously is in the range of 61100 to 20/100, preferably 10/100 to 201100. If (h) is present [be it introduced in admixture with (P) or with (e) or both or separately), the content of (e) may be considerably reduced, advantageously so that the weight ratio (e)/[(P) + (E)] in the compositions (U) containing (P), (e) and (h) is in the range of Case 150-5454 4/100 to 121100, preferably - in particular at preferred ratios (e)/(h) and in particular when employing the above-mentioned preferred surface- active derivatives (e31) of the novolake kind condensates - in the range of 4/100 to 10/100 or even 4/100 to 91100.
The compositions (U) of the invention comprise the mixtures (P) and the emulsifier systems (E) and may be handled in this form. A base may be added, if desired, in order to transform any carboxy groups and/or nonreacted anhydrides, at least in part, into the corresponding salt form, so that the pH of the composition diluted with water to 17. by weight of [(P) + (E) + optionally base] is advantageously in the range of 3 to 8, preferably 4 to 7. As bases for the adjustment of this pH-values are suitable, in general, conventional additives, in particular alkali metal hydroxides, carbonates or bicarbonates or preferably aliphatic amines, principally C2-3-alkanolamines, in particular mono-, di- or triethanolamine or mono-, di- or triisopropanolamine and/or alkylamines, advantageously C3-6-alkylamines, in particular, such in which the alkyl radicals correspond to those of the employed N-alkylphthalimides.
The compositions (U) of the invention are, in particular, such that consist essentially of (P) and (E) and optionally additional base, as indicated above. They are, in general, free-flowing to viscous liquids and are distinguished by their stability in shipment and storage, namely as well under conditions of heat as of frost, e.g. at temperatures below 101C or above +400C.
The phthalimide mixtures (P) of the inveniton, in particular in the form of their (E)-containing compositions (U) as described above, serve as assistants for the treatment of fibrous substrates with substances which are in the form of aqueous dispersions; in particular, they serve as carriers for the dyeing of fibrous material with disperse dyes or any other dyes that are applied in the form of their aqueous dispersions or for the optical brightening of fibrous material with disperse optical brighteners. The compositions (U) of the invention are readily dilutable with water; before use they may, if desired, be diluted with water to stock emulsions [e.g. containing 5 to 40 % by weight, preferably 10 to 30 % by weight of (U)] or they may also be added into the dyestuff or brightener stock dispersions or even directly into the liquors. The 9 Case 150-5454 aqueous stock emulsions respectively dispersions are distinguished by their storage stability and may be employed unchanged after several days; if they should separate or sediment after longer storage they may readily be emulsified or dispersed again by simple stirring. They are, in particular, suitable as carriers for the dyeing of synthetic or semi- synthetic fibrous materials, principally fibrous material of polyester, polyamide or cellulose acetates and their mixtures, as well as mixtures with natural fibres (in particular cotton or wool), e.g. cotton/polyester or wool/polyester, or with elastomeric fibres (e.g. polyurethanes). The substrates to be treated may be in any form as conventionally employed for the dyeing or optical brightening with the assistance of carriers, e. g. as loose fibres, yarns, filaments, skeins, cross-wound spools, woven or knitted goods, non-wovens, felts, carpets, tuftings as well as half- ready-made or ready-made goods. The application may take place according to methods known per Ee, in particular from aqueous medium, advantageously at pH 3 to 8, e.g. according to exhaust methods, under normal pressure advantageously at temperatures > 950C, or under superatmospheric pressure at temperatures above 100C, in particular in the temperature range from 102 to 1401C, e.g. under HT-conditions advantageously at 102 to 110C, or under rapid dyeing conditions at higher temperatures (polyester fibres preferably at temperatures in the range of 110 to 140C, polyamide fibres preferably at temperatures of 105 to 1150C, cellulose acetate fibres preferably at 105 to 125C), or by impregnation methods, e.g. by padding, dipping, spraying, foam application or printing (with printing pastes or printing inks) under conventional impregnation conditions (e.g. at temperatures in the range of 15 to 50C) and subsequent fixation, preferably at increased temperature, in particular above 100C, e.g. by steaming, preferably at 102 to 1200C, or thermosoling (e.g. at temperatures in the range of 130 to 220C; for polyamides preferably in the range of 130 to 160C and for polyester preferably in the range of 150 to 220C).
Due to the surprinsingly good emulsifiability of the mixtures (P) of the invention in the presence of (E), there may be achieved, even employing very small proportions of emulsifier systems (E), in particular of emulsifier (e), before all emulsifiers (e31) of the above-mentioned novolake surfactant kind, optimal effects, there taking place an outstanding and very quick distribution of (P) in finest particles into the aqueous system, so that its activity (in particular carrier activity) is immediately Case 150-5454 and best displayed and available in the dyeing process resp. brightening process. If desired, other conventional dyeing assistants may be admixed with the compositions (U) of the invention (in particular at latest in the aqueous treatment liquor) e.g. further carriers (0) that are compatible with N-alkylphthalimides, in particular alkyl-substituted aromatics and their mixtures, compounds of the aromatic or alkylaromatic carboxylic ester series, halogen substituted aromatics, compounds of the optionally alkyl- and/or hydroxy-substituted biphenyl, diphenylether or naphtholether series. The additional use of other N-alkylphthalimides is here expressively not recommended. If (P) is employed together with (0) or blended therewith, it is preferred that (P) outweighs. Further additives that may be employed together with the carrier compositions (U) of the invention are e.g. defoamers; if, as surfactants (E) in the compositions (U) of the invention, there are employed the above-mentioned novolake kind surfactants (e3), particularly (e31), the additional use of a defoamer is in general not necessary, since these bestow to the composition already an outstanding lack of foam, so that such compositions may be well employed, even without addition of defoamers also for processes in which foam would else appear in a disturbing amount (e.g. in dye-jet machines, for the dyeing of cross-wound spools, in the jigger or in the winch-beck). For the process of the invention there may be employed any conventional disperse dyes and disperse brighteners as they are defined e.g. in the "Colour Index" under the heading Misperse Dyes" and, in part, under the heading "Fluorescent Optical Brighteners" and which in their conventional commercial forms usually contain formulation additions (mainly dispersing agents), or also other dyes that, at least provisionally, contain no hydrosolubilizing substituents as e.g. sulphur dyes, vat dyes or developers.
With particular advantage the compositions (U) of the invention may be employed also in aqueous printing pastes and inks (e.g. for the printing of carpets or knitted goods) since they are capable or displaying their optimal efficiency, even in relatively concentrated treatment formulations.
By employing the carrier compositions (U) of the invention the properties of the employed dyes and brighteners can be optimally displayed and there can be obtained very regular dyeings in light to deep tones even with dye mixtures (e.g. trichromatic mixtures) in good penetration of the substrates. There may be obtained dyeings with optimum fastnesses.
Case 150-5454 The required resp. optimum quantity of the composition (U) of the invention to be employed with respect to the substrate or to the liquor may vary broadly, depending in the amount and kind of the dye or optical brightener, on the kind and structure of the substrate, on the employed treatment method and liquor-to-goods ratio and may be determined by means of a few preliminary tests. Mainly the compositions (U) of the invention are employed in concentrations of 0.3 to 25 g1l, referred to the aqueous treatment liquor; at a liquor to goods ratio of 5:1 to 40:1, in particular 20:1, advantageously at concentrations of 0.4 to 12 g/l, preferably 0.5 to 4 g1l.
In the following examples the parts and percentages are by weight; the temperatures are indicated in degrees Celsius. The dyes are employed in commercial form and their concentration in percent is referred to the substrates.
The employed N-alkylphthalimide mixtures (P) are listed in the following Table 1.
Table 1
Mixture by weight of N-R-phthalimide in (P) R = n-propyl (a) R = sec.-butyl (b) 1 pi 3 60 P2 3 55 P3 3 42 P4 3 17 P5 5 37 P6 6 31 P7 8 32 P8 8 27 P9 8 22 P10 10 32 P11 10 30 P12 10 22 P13 12 60 P14 12 28 pis 12 18 P16 12 8 Case 150-5454 R = n-butyl (c) 37 42 80 58 63 60 65 70 58 60 68 28 60 70 80 The employed emulsifier systems (E) are listed in the following Table 2, wherein v, x and y are emulsifiers (e) and z is an emulsifier assistant (h).
t.
1 Table 2
Emulsifier- by weight in system (E) W X y El 95 - - E2 40 - - E3 50 - - E4 80 - - E5 100 - - E6 - 90 10 E7 - 50 50 E8 - 20 80 E9 - 25 25 (E) z 60 so 20 Case 150-5454 w = novolake surfactant "compound 611 according to DE 32 46 383 C2 [i.e.
"compound 611 of Table (b) of USP 4 516 979] x = addition product of 32 moles of ethyleneoxide to 1 mole of castor oil y = monoethanolammonium dodecylbenzenesulphonate Z = C16-20-fatty acid methylester.
The employed carrier compositions (U) are set up in the following Table 3.
Table 3
Case 1505454 Carrier- Phthalimide mixture (P) Emulsifier system (E) composition (%) (%) (U) ul P1 (83) E3 (17) U2 P2 (83) E3 (17) U3 P3 (83) E3 (17) U4 P4 (80) E2 (20) us P4 (83) E3 (17) U6 P4 (90) E6 (10) U7 P4 (85) E7 (15) U8 P5 (83) E3 (17) U9 P6 (83) E3 (17) U10 P7 (84) E3 (16) Ull P7 (82) E4 (18) U12 P7 (82) E5 (18) U13 P7 (84) E9 (16) U14 P8 (83) E3 (17) U15 P9 (83) E3 (17) U16 P10 (83) E3 (17) U17 P11 (84) E3 (16) U18 P11 (82) E4 (18) U19 P11 (85) E5 (15) U20 P11 (84) E9 (16) U21 P12 (83) E3 (17) U22 P13 (83) E3 (17) U23 P13 (88) E8 (12) U24 P14 (83) E3 (17) U25 P15 (83) E3 (17) U26 P16 (95) E1 (5) U27 P16 (83) E3 (17) If required monoethanolamime or diisopropanolamine is added to the above carrier compositions (U) (pH of the aqueous diluted composition of 1 % concentration = 4 to 6).
1 - is - Example 1
Case 150-5454 A texturized polyester (diolene loft) jersey is padded on a padding machine at ambient temperature (= 20OC), to a pick-up of 80 % with an aqueous liquor containing per 1000 parts parts of the dye C.I. Disperse Yellow 64 (structure no. 47023) and 10 parts of the assistant U20.
The pH is set to 4.5 with acetic acid.
The textile material is intermediately dried on a pin stenter during 120 seconds at 1100C and then thermosoled during 90 seconds at 195C. After reduction clearance there is obtained a level, intense yellow dyeing of good general fastnesses.
Example 2
A polyester/cotton blended fabric (blend ratio 67:33) is padded at ambient temperature with an aqueous liquor (pick-up 60 %). The aqueous liquor contains per 1000 parts:
parts of the red dye C.I. Vat Red 10 (structure no. 67000) 10 parts of the red dye C.I. Disperse Red 202 and 10 parts of the composition U16.
The pH is set to 4.5 with acetic acid.
The impregnated blended fabric is dried during 60 seconds at 1100C and then treated with hot air at 210C during 60 seconds. The vat dye is developed at 600C during 30 seconds using the following aqueous liquor (liquor-to-goods ratio 5:1) that contains (per 1000 parts):
parts of 30 % sodium hydroxide solution 8 parts of sodium dithionite and 3 parts of an anionic dispersing agent (sodium salt of a P-naphtha- lene sulphonic acid/formaldehyde condensation product, commercially 4 k available.
Case 150-5454 After soaping at the boil during 20 minutes rinsing and drying there is obtained a fabric in which the polyester portion and the cotton portion are dyed red nearly tone-in-tone. The dyeings have at a good colour depth a level appearance and good general fastnesses.
Example 3
In an HT-dyeing machine a liquor of 1300C is flown through bobbins of texturized polyester yarns at a liquor-to-goods ratio of 10:1. The liquor contains demineralized water (set to pH 4.5 with acetic acid), 1.5 g11 of the assistant U17 and the following dyes:
1) 0.46 % of the dye of formula -0 ---c 0 1 H 2) 0.52 % of the dye of formula HO 0 \ A -G 1 OH /Y R% (a), M$ 3) 0.17 % of the mixture of the dyes of formulae (yl) and (Y2) (in even portions) k HO H-CH20H 0= 0 HO H2 (Y1) Case 150-5454 HO H__CH20H 0= 0 H2N H (Y2) The flow rate throught the bobbins is of 40 1/kg per minute. After 30 minutes of treatment at 130C the liquor is cooled and drained off and the goods are cleared under reducing conditions. There is obtained a perfectly level brown dyeing of full yield. During the dyeing foam- formation is minimal.
Example 4
A polyester fabric (type DACRON) is dyed in a GASTON-COUNTY dye-jet machine with 0.5 % of the dye Foron Rubine SE-GFL with addition of 2 g/1 of ammonium sulphate and 2 g11 of the product U17 at pH 5.0 (adjusted with formic acid). The liquor-to-goods ratio is 20:1. Dyeing is started at 20'C; during 10 minutes the dye-bath is heated to 700C. After 20 minutes at 1301C the dyeing is concluded. There is obtained a level dyed fabric.
Example 5
Example 4 is repeated with the difference that instead of Foron Rubine SEGFL there is employed Foron Brilliant Blue S-R. There is obtained a level and very brilliant blue dyeing of the fabric.
Example 6 parts of cleaned polyester fibrous material are given in a high temperature dyeing machine (GASTON COUNTY dye-jet machine) into 100 parts of a dyeing liquor heated at 700c, that contains 0.1 parts of a commercial preparation (with dispersing agent) of the dye C.I. Disperse Blue 148, 0.2 parts of the composition U23 and 2 parts of ammonium sulphate and the pH j C Case 150-5454 of which is set to 5 with formic acid. The dyeing machine is closed, the temperature is raised during 20 minutes to 130C and maintained for 20 minutes at this temperature. After cooling the treated substrate is taken out from the dye bath, rinsed, soaped, rinsed again and dried. There is obtained a completely level, deep blue dyeing of very good fastness properties.
Example 7 parts of polyester fibre fabric are dyed in a closed dyeing vessel with 400 parts of an aqueous dyeing liquor, that contains 0.05 parts of the commercial form of the dye C.I. Disperse Red 73, 0.7 parts of the composition U15 and 3 parts of ammonium sulphate and the pH of which is set to 5 with formic acid, by heating during 30 minutes from 600C to 1300C inner temperature and dyeing during 30 minutes 'at this temperature. After cooling the dyed fabric is taken out from the bath, rinsed, rinsed again and dried. There is obtained a perfectly level ruby red dyeing of excellent fastness properties.
Example 8 parts of a polyester fibre fabric are given into 4000 parts of an aqueous dye bath which is heated to 40C and contains 0.2 parts of C.I. Disperse Blue 73, 6 parts of the composition U21 and 8 parts of ammonium sulphate and the pH of which is set to 5 with formic acid. This bath is heated during 30 minutes to 97C and maintained for 1 hour at this temperature. After washing, rinsing and drying there is obtained a levelblue penetration dyed fabric with very good fastness properties.
Example 9
A polyester ribbon (satin) of unstretched (1:3.2) and normally stretched (1:3.66) yarn is given into an aqueous liquor (liquor to goods ratio 40:1) heated to 601C and which contains 3.2 X of the dye C.I. Disperse Blue 87, 2 g/1 of ammonium sulphate, 4 g11 of citric acid and 2 g11 of the assistant U17, then heated during 45 minutes to 130% dyed during 60 minutes and then cooled. The treated substrate is rinsed and dried. In this way there is obtained a perfectly level, turquoise blue dyed ribbon.
1 Example 10
Case 150-5454 parts of a yarn consisting of 50% of wool and 50% of polyethyleneterephthalate are dyed in 4000 parts of an aqueous bath that contains 2 g/l of ammonium sulphate and the pH of which is set to 5.5 with acetic acid and further contains the following additions:
0.6 parts of the dye of formula (8) and 5 parts of the assistant U17.
The yarn is given into the bath at 60% then the bath is heated during 45 minutes to 106C and dyeing is carried out during 60 minutes at this temperature. After cooling the yarn is rinsed and dried. There is obtained a level yellow dyeing in which the polyester portion is dyed substantially more than the wool portion.
Analogously as the carrier compositions U1S, U16, U20, U21 and U23 there are employed in the above examples 1, 2, 5, 6, 7 and 8 each of the other carrier compositions U1 to U27. Analogously as the carrier composition U17 there are employed in Example 3 the carrier compositions Ul-U5, U8- U12, U14-U19, U21, U22 and U24-U27.
In the above Examples the carrier compositions (U) may be added directly into the liquors or may previously be diluted to aqueous stock solutions, produced e.g. by diluting of 10 parts of each of the compositions Ul-U27 with 90 parts of demineralized water at ambient temperature.
f
Claims (26)
- Case 150-5454 1. An N-alkylphthalimide mixture (P) consisting essentially of:(a) N-(n-propyl)-phthalimide (b) N-(sec,C4-6-alkyl)-phthalimide and (c) N-(n-C4-6-alkyl)-phthalimide wherein the weight ratio (a)/(P) is in the range of 3/100 to 141100.
- 2. A mixture (P) according to Claim 1, wherein the weight ratio (a)/(P) is in the range of 5/100 to 12/100.
- 3. A mixture (P) according to Claim 1 or 2, wherein the weight ratio (b)/(c) is in the range of 1/10 to 4/1.
- 4. A mixture (P) according to any of Claims 1 to 3, wherein the weight ratio (b)I(P) is in the range of 8/100 to 70/100.
- 5. A mixture (P) according to any of Claims 1 to 4, wherein the weight ratio (c)I(P) is in the range of 551100 to 80/100 and the weight ratio (b)/(P) is in the range of 17/100 to 421100.
- 6. A composition (U) comprising a phthalimide mixture (P) according to any of Claims 1 to 5 and free of other phthalimides and further comprising an emulsifier system (E).
- 7. A composition (U) according to Claim 6, wherein the emulsifier system (E) comprises at least one emulsifier (e).
- 8. A composition (U) according to Claim 7, wherein (e) is (el) at least one anionic emulsifier optionally in admixture with (e2) at least one non-ionic emulsifier.1 f - 21
- 9. A composition (U) according to Claim 8, wherein (el) is Case 1505454 (ell) an at least partially carboxymethylated, phosphated or sulphated polyalkyleneglycolether of a hydrocarbon-mono- or -polyol containing on average at least 10 carbon atoms per hydroxy group of the mono or polyol, (e12) a sulphate, phosphate or carboxymethylated derivative of a sorbitan or glycerine fatty acid ester, wherein the fatty radical contains 12 to 24 carbon atoms or of a polyalkyleneglycolether thereof, or (e13) a C12-24-hydrocarbon sulphonic acid, the carboxy, phosphate or sulpho groups optionally being in salt form, or a mixture of such surfactants, and (e2) is (e2l) a polyalkyleneglycolether of a hydrocarbon-mono- or -polyol, containing on average at least 10 carbon atoms per hydroxy group of the mono- or polyol or (e22) a sorbitan or glycerine fatty acid ester, in which the fatty radical contains 12 to 24 carbon atoms, or a polyalkyleneglycolether thereof or a mixture of such surfactants.
- 10. A composition (U) according to Claim 8 or 91 wherein (e) is an at least partially sulphated addition product of 4 to 20 moles of ethyleneoxide to 1 val of oligomeric methylene bridge-containing condensation product of alkylphenol and formaldehyde, optionally in admixture with non-sulphated starting material.Case 150-5454
- 11. A composition comprising a phthalimide mixture (P) according to any of Claims 1 to 5, which is free of other phthalimides, and further containing (h) at least one lipophilic non-ionic emulsifying assistant.
- 12. A composition (U) according to any of Claims 6 to 11, comprising (P), (e) and (h).
- 13. A composition according to Claim 11 or 12, wherein (h) is an oilsoluble fatty acid-(C1-4-alkyl)ester with 12 to 24 carbon atoms in the fatty acid radical or a mixture of such esters.
- 14. A composition (U) according to Claim 12 or 13, wherein the weight ratio (e)/(h) is in the range of 9515 to 40/60.
- 15. A composition (U) according to any of Claims 6 to 14, wherein (E) consists of (e) and optionally (h).
- 16. A composition (U) according to any of Claims 6 to 15, wherein the weight ratio (E)/[(P) + (E)] is in the range of 5/100 to 201100.
- 17. A composition (U) according to any of Claims 7 to 16, wherein the weight ratio (e)/[(P) + (E)] is in the range of 6/100 to 12/100.
- 18. A composition (U) according to any of Claims 6 to 17, essentially consisting of (E) and (P) and optionally additional base.
- 19. A process for the treatment of fibrous substrates with substances that are in the form of aqueous dispersions, in the presence of a mixture (P) according to any of Claims 1 to 5 as an assistant.
- 20. A process according to Claim 19 for the dyeing or optical brightening of fibrous material with dispersed dyes or disperse optical brighte- ners.
- 21. A process according to Claim 19 or 20, wherein the mixtures (P) according to any of Claims 1 to 5 are employed in the form of compositions (U) according to any of Claims 6 to 18.Case 150-5454
- 22. A carrier composition comprising (P), defined as in any of Claims 1 to 5, as a carrier-active substance and at least a further carrier but free of other phthalimides than those defined in (P).
- 23. A carrier composition according to Claim 22 further containing (e) and/or (h) defined as in Claims 7 and 11.
- 24. An N-alkylphthalimide mixture (P), according to any of Claims 1 to 5, substantially as hereinbefore described and as specifically disclosed in any of mixtures (P1) to (P16).
- 25. A composition according to any of Claims 6 to 18, substantially as hereinbefore described and as specifically disclosed in any of compositions Ul to U27.
- 26. A process according to any of Claims 19 to 21, as hereinbefore described and as specifically disclosed in any of Examples 1 to 10 and in each of the two paragraphs following Example 10.Published 1992 at The Patent Office. Concept House. Cardif. f Road. Newport- Gwent NP9 1RH. Further copies may be obtained floni Sales Branch. Unit 6. Nine Mile Point. Cwrnfelinfach. Cross Keys. Newport. NPI 7HZ Printed by Mult:plex techniques lid. St Mar.v Cray. Kent
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE4027075 | 1990-08-27 |
Publications (3)
Publication Number | Publication Date |
---|---|
GB9118129D0 GB9118129D0 (en) | 1991-10-09 |
GB2247470A true GB2247470A (en) | 1992-03-04 |
GB2247470B GB2247470B (en) | 1994-07-13 |
Family
ID=6413015
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB9118129A Expired - Fee Related GB2247470B (en) | 1990-08-27 | 1991-08-22 | N-Alkylphthalimide mixtures for use as carriers in dyeing and optical brighting |
Country Status (9)
Country | Link |
---|---|
JP (1) | JPH04245983A (en) |
BE (1) | BE1004777A3 (en) |
CA (1) | CA2049867C (en) |
CH (1) | CH682578A5 (en) |
ES (1) | ES2037597B1 (en) |
FR (1) | FR2666087B1 (en) |
GB (1) | GB2247470B (en) |
HK (1) | HK62897A (en) |
IT (1) | IT1251245B (en) |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5968203A (en) * | 1997-02-28 | 1999-10-19 | Sybron Chemicals Inc. | Clay-containing textile material treating composition and method |
US5972049A (en) * | 1998-01-28 | 1999-10-26 | Sybron Chemicals Inc. | Clay-containing dispersing composition for carriers used in the disperse dyeing of hydrophobic textiles |
WO2007104916A1 (en) * | 2006-03-15 | 2007-09-20 | Dylon International Limited | Whitener for polyester fabrics |
WO2008097356A2 (en) * | 2006-09-08 | 2008-08-14 | Southern Mills, Inc. | Methods and systems for providing dyed, stretchable flame resistant fabrics and garments |
CN101498107B (en) * | 2008-07-11 | 2012-04-25 | 杭州传化精细化工有限公司 | Dressing agent and preparation thereof |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP5629104B2 (en) * | 2010-03-24 | 2014-11-19 | 株式会社クラレ | Method for dyeing polyetherimide fiber and dyed product thereof |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB1193948A (en) * | 1968-04-20 | 1970-06-03 | Bayer Ag | Printing and Dyeing Process |
GB1444887A (en) * | 1974-03-15 | 1976-08-04 | Bayer Ag | Process for dyeing natural and/or synthetic polyamide fibre materials below the boil |
EP0379954A2 (en) * | 1989-01-25 | 1990-08-01 | Bayer Ag | Carrier for dyeing hydrophobic fibre materials |
US4994089A (en) * | 1988-10-12 | 1991-02-19 | Bayer Aktiengesellschaft | Carrier mixture for the dyeing of polyester materials: n-alkylphthalimide and aromatic ester or ether |
Family Cites Families (6)
Publication number | Priority date | Publication date | Assignee | Title |
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BE795961A (en) * | 1972-02-25 | 1973-08-27 | Hoechst Ag | APPLICATION OF SULPHURIC HEMI-ESTERS TO DISPERSION OF COLORANTS |
DE2342293A1 (en) * | 1973-08-22 | 1975-04-24 | Bayer Ag | PRINTING AND INKING PROCESS |
DE2356548A1 (en) * | 1973-11-13 | 1975-06-26 | Cassella Farbwerke Mainkur Ag | METHOD OF DYING POLYAMIDE FIBERS WITH SULFUR DYES |
US4252534A (en) * | 1978-10-19 | 1981-02-24 | Ciba-Geigy Corporation | Dyeing assistants and their use in dyeing synthetic fibre material |
GB2112817B (en) * | 1981-12-24 | 1986-01-22 | Sandoz Ltd | Improvements in or relating to organic compounds |
CH653068A5 (en) * | 1982-01-02 | 1985-12-13 | Sandoz Ag | TOOLS for dyeing with disperse dyes. |
-
1991
- 1991-08-21 ES ES9101917A patent/ES2037597B1/en not_active Expired - Fee Related
- 1991-08-22 GB GB9118129A patent/GB2247470B/en not_active Expired - Fee Related
- 1991-08-23 JP JP3212114A patent/JPH04245983A/en active Pending
- 1991-08-23 CH CH2486/91A patent/CH682578A5/en not_active IP Right Cessation
- 1991-08-26 CA CA002049867A patent/CA2049867C/en not_active Expired - Lifetime
- 1991-08-26 BE BE9100785A patent/BE1004777A3/en not_active IP Right Cessation
- 1991-08-27 IT ITMI912290A patent/IT1251245B/en active IP Right Grant
- 1991-08-27 FR FR9110710A patent/FR2666087B1/en not_active Expired - Fee Related
-
1997
- 1997-05-15 HK HK62897A patent/HK62897A/en not_active IP Right Cessation
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB1193948A (en) * | 1968-04-20 | 1970-06-03 | Bayer Ag | Printing and Dyeing Process |
GB1444887A (en) * | 1974-03-15 | 1976-08-04 | Bayer Ag | Process for dyeing natural and/or synthetic polyamide fibre materials below the boil |
US4994089A (en) * | 1988-10-12 | 1991-02-19 | Bayer Aktiengesellschaft | Carrier mixture for the dyeing of polyester materials: n-alkylphthalimide and aromatic ester or ether |
EP0379954A2 (en) * | 1989-01-25 | 1990-08-01 | Bayer Ag | Carrier for dyeing hydrophobic fibre materials |
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5968203A (en) * | 1997-02-28 | 1999-10-19 | Sybron Chemicals Inc. | Clay-containing textile material treating composition and method |
US5972049A (en) * | 1998-01-28 | 1999-10-26 | Sybron Chemicals Inc. | Clay-containing dispersing composition for carriers used in the disperse dyeing of hydrophobic textiles |
WO2007104916A1 (en) * | 2006-03-15 | 2007-09-20 | Dylon International Limited | Whitener for polyester fabrics |
WO2008097356A2 (en) * | 2006-09-08 | 2008-08-14 | Southern Mills, Inc. | Methods and systems for providing dyed, stretchable flame resistant fabrics and garments |
WO2008097356A3 (en) * | 2006-09-08 | 2008-11-13 | Southern Mills Inc | Methods and systems for providing dyed, stretchable flame resistant fabrics and garments |
CN101498107B (en) * | 2008-07-11 | 2012-04-25 | 杭州传化精细化工有限公司 | Dressing agent and preparation thereof |
Also Published As
Publication number | Publication date |
---|---|
HK62897A (en) | 1997-05-23 |
IT1251245B (en) | 1995-05-05 |
GB2247470B (en) | 1994-07-13 |
CA2049867A1 (en) | 1992-02-28 |
BE1004777A3 (en) | 1993-01-26 |
ES2037597B1 (en) | 1994-03-16 |
ES2037597A1 (en) | 1993-06-16 |
GB9118129D0 (en) | 1991-10-09 |
FR2666087B1 (en) | 1995-02-03 |
FR2666087A1 (en) | 1992-02-28 |
ITMI912290A0 (en) | 1991-08-27 |
CH682578A5 (en) | 1993-10-15 |
ITMI912290A1 (en) | 1992-02-28 |
CA2049867C (en) | 2008-04-01 |
JPH04245983A (en) | 1992-09-02 |
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Legal Events
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732E | Amendments to the register in respect of changes of name or changes affecting rights (sect. 32/1977) | ||
PCNP | Patent ceased through non-payment of renewal fee |
Effective date: 20090822 |