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
  • D06P1/90—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 dyes dissolved in organic solvents or aqueous emulsions thereof
  • D06P1/92—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 dyes dissolved in organic solvents or aqueous emulsions thereof in organic solvents
  • D06P1/928—Solvents other than hydrocarbons
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
  • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
  • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
  • C08G65/32—Polymers modified by chemical after-treatment
  • C08G65/329—Polymers modified by chemical after-treatment with organic compounds
• • 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
• • 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
  • D06P1/65125—Compounds containing ester groups
• • D—TEXTILES; PAPER
  • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
  • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
  • D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
  • D06P3/34—Material containing ester groups
  • D06P3/52—Polyesters
  • D06P3/54—Polyesters using dispersed dyestuffs

Definitions

• This invention relates to waterless compositions, particularly adapted for immersion coloring of plastic articles, used in apparel- and textile-related appli- cations.
• references disclosing the use of glycols or glycerol as media for dyeing compositions include:
• compositions containing esterified derivatives of a Diels-Alder adduct of linoleic acid and acrylic acid, intended for use in various textile-treating compo- sitions, have been disclosed by Wilson, in U.S. Patents 4,293,305 and 4,394,126, incorporated herein by reference.
• Such articles include, but are not limited to buttons, zippers, garments, carpeting, ribbons, draperies, shoe strings, sewing thread, lace, socks and other notions, used in clothing manufacture.
• this invention relates to a waterless dip dye composition for apparel- and textile-related articles, comprising an aromatic ester of the formula ArCOOR 2 , ArCOO-R j -OOCAr or (ArCOO) -R occasion, wherein R ⁇ is alkylene of 2-8 carbon atoms or polyoxyalkylene of the formula -C H Directory (OC H Directory ) , in which r is 2 or 3 and s is 1 to 15; R « is substituted or unsubstituted alkyl or alkenyl of 8-30 carbon atoms; R caution is the residue of a polyhydric alcohol having z hydroxyl groups; Ar is substituted or unsubstituted mono or bicyclic aryl of up to 15 carbon atoms and z is 3-6, admixed with at least 0.5% by weight of a dyeing assistant composition and an organic colorant.
• this invention in another aspect, relates to a process for waterless color ⁇ ation of apparel- and textile-related articles, fabricated from a plastic compo ⁇ sition, comprising exposing an article to the foregoing compositions, maintained at a temperature between 100° C and the temperature at which the plastic degrades, for a time adequate to achieve the desired degree of coloration.
• "Aromatic ester” as used in the specification and claims, means an ester formed by reaction between a mono-, di- or polyh dric alcohol and an aromatic acid, so as to accomplish complete esterification of all hydroxyl functions therein.
• esters within this class include esters of the formula ArCOOR classroom, wherein Ar is substituted or unsubstituted mono- or bicyclic aryl of up to 15 carbon atoms and is substituted or unsubstituted alkyl or alkenyl of 8-30 carbon atoms. Also included within the definition of aromatic esters are those of the formula Ar-COO-R_-
• Ar is as above and R. is alkylene of 2-8 carbon atoms or polyoxyalkylene of the formula -C rB, £ ((K- ⁇ H, * ⁇ T ) s_, in which r is 2 or 3 and s is 1 to 15.
• aromatic esters used in this aspect of the invention include, but are not limited to, esters of benzoic, toluic, di ethylbenzoic, trimethyl- benzoic, naphthoic, butylbenzoic and similar acids.
• esters will preferably be used in combination with a cycloaliphatic diester of the formula
• R is substituted or unsubstituted straight or branched chain alkyl of 4-20 carbon atoms, polyoxyalkylene of the formula HO(C x H y 0) nC x H y- or phosphated polyoxyalkylene of the formula
• (HO) 2 P( O)O(C ⁇ H 2 ⁇ O) n C ⁇ H 2 ⁇ or a salt thereof, wherein (C ⁇ H 2 ⁇ O) n is (CH 2 CH 2 O) n , (C 3 H g O) n or (CHgCHgO) - (CgHgO) and n is 2-22.
• compositions of this invention contain at least 5% by weight of a diester of this composition.
• Preferred aromatic esters employed in the practice of this invention include those based on tri- or polyhydric alcohols, such as glycerol, tri ethylolpropane, pentaerythritol, diglycerol, sorbitol, mannitol, and the like.
• the aromatic acids used for esterification are as above. When esters of this type are used, it has been found that entirely acceptable dyeings can be obtained, without the use of a cyclo ⁇ aliphatic diester, required for good results in combination with aromatic esters of mono- and dihydric alcohols.
• Aromatic esters of tri- and polyhydric alcohols can be represented by the formula (ArCOO) z -Rg, wherein R g is the residue of a polyhydric alcohol having z hydroxyl groups and z is 3-6.
• alkylene (R,) can be ethylene, propylene, hexylene, 2,2- dim ethyl trim ethylene, butylene, hepta- methylene and octylene, including various isomers thereof.
• Polyoxyalkylene diesters include those derived from polyethylene glycol or polypropylene glycol.
• alkyl R substituents can be octyl, nonyl, decyl, dodecyl, tridecyl, hexadecyl, stearyl and alkenyl can be any corresponding monounsaturated function, e.g., oleyl.
• aromatic esters of mono-or dihydric alcohols are those wherein:
• R is ethylene or propylene, including each of (a) and (b),
• R is ethyleneoxyethylene or propyleneoxypropylene, including each of (a) and (b),
• (e) R is polyoxypropylene of molecular weight 200-250, including each of (a) and (b), and
• R demand is decyl, dodecyl, hexadecyl, tridecyl, octadecyl or oleyl, including each of (a) and (b).
• Contemplated equivalents of the aromatic esters described above include esters of benzyl alcohol and substituted or unsubstituted aromatic acids of 6 or more carbon atoms, or substituted or unsubstituted aliphatic acids of 8 or more carbon atoms, including but not limited to, benzyl laurate, benzyl pelargonate, benzyl octoate, benzyl palmitate, benzyl stearate, benzyl oleate, benzyl hydroxy- stearate or benzyl benzoate. It will be understood that esters of substituted benzyl alcohols can also be used.
• Preferred aromatic esters based on trihydric or polyhydric alcohols are those of glycerol, trimethylolpropane or pentaerythritol. Most preferred are benzoate or toluate esters. It will be understood that mixtures of aromatic acids can be used to prepare any of the aromatic esters used in the practice of this invention.
• the dibasic cycloaliphatic acid employed in making the compositions of this invention is a Diels-Alder adduet of aerylic acid and linoleic acid and can be prepared as described by Ward in U. S. Patent 3,753,968.
• the diacid has the formula
• OMPI is a mixture of (5 and 6)-carboxy-4-hexyl-2-cyclohexene-l-octanoic acids.
• the diacid is available commercially from Westvaco, designated as "Diacid 1550".
• the alkyl esters are reported as being useful in lubricant applications, including users as textile lubricants and plasticizers for PVC.
• the diacid can be esterified with alcohols using, for example, acidic catalysts such as p-toluenesulfonic acid, methanesulfonic acid or sulfuric acid.
• acidic catalysts such as p-toluenesulfonic acid, methanesulfonic acid or sulfuric acid.
• the reaction mixture is preferably also treated with a decolorizing agent, e.g., carbon or clay.
• the diacid is reduced following esterification to a saturated compound cycle.
• a nickel catalyst such as Raney Nickel, nickel on kieselguhr or nickel on alumina can be used. The required amount varies up to 5 - 10% by weight of the ester.
• Hydrogenation is carried out after esterification to prevent nickel from complexing with the free acid.
• Other catalysts e.g., platinum or rhodium, avoid this problem, but are prohibitive in cost.
• the catalyst can be removed by filtration through a plate and frame filter press. The product is the resulting filtrate.
• Polyoxyalkylene diesters are prepared by reaction of the diacid, in the presence of an alkaline catalyst, with ethylene or propylene oxide. Reaction will occur at both acid sites. Addition of ethylene oxide is allowed to continue until the product becomes at least dispersible or, preferably, soluble in water. This will correspond to addition of a total of 5 - 25 ethylene oxide units.
• the product obtained using ethylene oxide has a structure before hydrogenation represented by the formula:
• the phosphorylated product is readily obtained by reaction with phosphorus pentoxide.
• the saturated diester can be obtained by nickel-catalyzed hydro- genation.
• the phosphorylated derivatives can be converted to salts thereof by reaction with a metal hydroxide. Sodium and potassium salts are preferred.
• R is ArCOO(CH 2 CH 2 O) CHgCHg-, etc.
• an aromatic acid e.g., benzoic, toluic or mellitic acid
• Hydrogenation of the double bond in the cycloaliphatic ring can be done before or after esterification with the aromatic acid.
• substituted alkyl R which ay be used in the products of this invention are butoxybutyl, 10-hydroxystearyl, 10-hydroxydecyl, IO-halostearyl, t -alkanoyloxyalkyl or the like.
• Preferred diesters for use in accordance with the principles of the invention are those wherein:
• R is straight or branched chain alkyl of 4 - 20 carbon atoms
• R is 2-ethylhexyl, lauryl or stearyl
• R is HO(CH 2 CH 2 O) n CH 2 CH 2 -,
• R is HO(C 3 HgO) n C 3 H 6 -
• R is HO(C 2 H 4 O) (C 3 HgO) C 3 Hg-,
• R is CH 3 C g H 4 CO(OC 2 H 4 ) n OC 2 H 4 -
• R is CgH 5 CO(OC 3 H 6 ) n OC 3 H 6 -
• R is CH 3 CgH 4 CO(OC 3 H 6 ) n OC 3 H 6 -.
• Dyeing assistant agent includes alkoxylated alkylphenols and their esters, alkoxylated castor oil compounds, alkoxylated hydrogenated castor oil compounds, alkoxylated primary alkanols, salts of phosphated alkoxylated primary alkanols and mixtures thereof.
• the amount of dyeing assistant agent, employed in the compositions of this invention is at least about 0.5% by weight of the composition. However, it is preferred that the compositions contain at least 5%, more preferably up to about
• compositions can also contain 60 -80% by weight of the dyeing assistant agent.
• Preferred dyeing assistant agents are alkoxylated alkylphenols and their esters. These are compounds of the formula
• exemplary dyeing assistant agents include ethoxylated and propoxylated alkyl phenols and corresponding esters, such as the laurate, myristate, palmitate, coconate, oleate, stearate, isostearate, benzoate and toluate esters.
• Preferred alkylphenols are nonylphenol, octylphenol, and dodecylphenol. It will be understood that the alkylphenols and the acids used to esterify the alkoxylated alkylphenols can include mixtures.
• the alkoxylated alkylphenols will be ethoxylated deriv ⁇ atives, having 5 - 10 ethylene oxide units.
• Preferred dyeing assistant agents will be those wherein: (a) R" is alkanoyl of 12 - 18 carbon atoms, including mixtures thereof;
• R" is n-C 1? H 33 CO;
• R" is n-C 1? H 35 CO;
• R" is iso-C 1? H 35 CO;
• R" is benzoyl;
• R" is n-C u H 23 CO;
• (h) a is 5 - 10, including each of (a) - (g);
• (i) b is 6 - 15, including each of (a) - (h);
• (j) b is 8 - 11, including mixtures thereof and including each of (a) - (h); (k) a is 9, b is 8 - 10 and R" is n-C u H 23 CO;
• (m) x is 2, including each of (a) - (1).
• Alkoxylated castor oil used as an optional additive in the compositions of this invention will contain 15 - 100 oxyalkylene units, preferably 40 -85 oxyethylene units.
• the hydrogenated cator oil derivatives will contain 5 - 200 oxyalkylene units, preferably 20 - 30 oxyethylene units.
• Polyester articles include those made from poly(alkylene terephthalates), such as poly(ethylene terephthalate), or polyesters made from cyclohexanedi- m ethanol. Typical of polyester articles are presewn garments, including slacks, jeans, dresses, shirts, scarves and the like. Also included within the scope of polyester articles are buttons, draperies, laces, seatbelts, ribbons, zippers and other notions.
• Polyamides particularly contemplated as substrates in the practice of this invention include those known as nylons 6; 6,6 or 6,10.
• Articles which can be colored in accordance with the invention include the same types of articles as for polyesters, as well as lingerie and hosiery. It is common, for example, to employ polyamide teeth in zipper constructions. Also, polyamide is often used for carpeting.
• Acrylic plastics contemplated within the scope of this invention include straight acrylics, such as polyacrylonitrile, and modacrylics. The latter are copolymers of acrylonitrile or methacrylonitrile, generally with vinyl chloride or vinylidene chloride. Articles made from acrylics include clothing, carpeting and notions.
• Polyurethanes include a myriad of compositions, made by reaction, for example, between glycols and organic di- or polyisocyanates.
• glycols used to make polyurethanes, are simple glycols, such as the alkylene glycols, and polymeric glycols, including polyether and polyester glycols.
• Articles containing polyurethane, used in textile and garment manufacture include rain wear and artificial leather, which can be colored by the teachings of the instant invention.
• OMPI VvIPO OMPI VvIPO
• the foregoing types of plastics can be blended with natural or synthetic cellulosic materials and colored according to this invention.
• Organic colorant includes both dyes and pigments of any structure. Normally, the dyes or pigments which are employed need not be soluble in water. Therefore, such dyes and pigments will not usually contain water-solubilizing functions, such as a plurality of sulfonic acid groups.
• the dyes/pigments used in the practice of this invention generally will be chosen from among water-insoluble dyes, which may also be known as disperse dyes. Included within this class of dyes, which can be used on fibers such as cellulose actate, polyamides or polyesters, from any kind of dyeing medium are colors of the azo, azomethine, nitroarene and anthraquinone structures. It will be understood that the dyes useful in the practice of the present invention are not limited to these classes of compounds.
• the dyes or pigments used in the practice of this invention may be identified by their chemical names, for example:
• 3-nitro-N -phenylsulfanilanilide a yellow dye
• p-[p-(phenylazo)phenylazo] - phenol a red-yellow dye
• ethyl 4-hydroxy-l-anthraquinonecarbamate an orange dye
• l-amino-4-hydroxyanthraquinone a red dye
• l-amino-2-bromo-4-hydroxy- anthraquinone a red-blue dye or 4,5-diamonochrysazin
• blue dye a blue dye.
• the dyes alternatively may be identified in accordance with standard chemical handbooks, such as "The Color Index,” third edition, The Society of Dyes and Colors and the American Association of Textile Chemists and Colorists (1971). This sort of handbook correlates dye structure with trade names. Typical of colorants identified in accordance with this handbook, which can be used in the practice of this invention, are Solvent Orange 20; Acid Blue 83 (C.I. 42660), Acid Blue 59 (C.I. 50315), Direct Blue 86 (C.I. 74180); Direct Red 81 (C.I. 28160) and Acid Yellow 36 (C.I. 13065).
• Cationic dyestuffs can also be used in the practice of this invention, for example Rhodamine 6G, Rhodamine B, Rhoduline Blue 6G and Methylene Blue BB.
• metallized azo dyestuffs can be employed in the practice of this invention.
• Representative metallized azo dyes which can be employed are Co, Ni, Cu or Cr complexes of coupling products of 2-amino-4-nitrophenol and resorcinol; 2-amino-4-chloro-5-nitrophenol and acetoacetanilide; dianisidine and 3-hydroxy-2- naphthanilide; 2-amino-4-chloro-5-nitrophenol and 2-aminonaphthalene or the like.
• the dyes/pigments can be used in any form, that is as presscake or as dried pressed dye.
• the addition of dispersing agents is optional.
• the dyes or pigments can be added to the dye bath in a solvent/dispersing medium compatible with the dye bath. It is convenient and preferred, in the practice of this invention, to use solid disperse dyes free of additives.
• the dyeings can be done at 180 - 200° C. or higher.
• compositions of this invention at 200° C. or more does not result in smoking or pollution of the processing plant, which is a problem when ethylene glycol or diethylene glycol are the dyeing solvents.
• a temperature up to that at which the plastic being dyed, will degrade.
• the dyes can also be applied by spraying. Then, the sprayed articles should be heated in a bath to at least 140° C to complete uptake of the dye into the article.
• the dyed article is normally cleaned with a solvent to remove excess dye.
• the solvents used for cleaning are chlorinated or fluorinated hydrocarbons.
• highly chlorinated solvents such as perchloroethylene and trichloroethylene are preferred for cleaning by immersion in a liquid bath.
• Fluorochlorocarbons such as dichloro- difluororo ethane, chlorotrifluorom ethane, which are gases at ambient temperatures or slightly above, can be used for vapor-phase cleaning of the dyed articles. Normally, means will be used to recover and recycle the cleaning solvent, rather than discharging it to the atmosphere.
• a further advantage of the process of the invention is that it is essentially self-contained and effluent free, that is, little or no material is lost or discharged to the atmosphere.
• the major components include a dip tank, a dye recovery unit, a solvent cleaning tank, a solvent recovery still and a drier.
• the dip tank will be provided with heating means and stirring means, so as to permit circulation of the dyeing solution within the dip tank and to a dye recovery unit external thereto.
• the dye recovery unit normally includes filtration means for removal of solid debris from used dye solutions and distilling and condensing means for recovery of the solvent.
• the purified dye solution can be recycled to the dip tank, with addition of dye or other additives to provide the desired composition in the dip tank, or can be stored for later use.
• Articles leaving the squeeze roll station are passed into the solvent cleaning tank to complete removal of any excess or unadherent dye matter. It is preferred to use a plurality of solvent cleaning tanks. It is also preferred to circulate solvent from the tank through an external solvent recovery unit, provided with filters to remove solid materials and distilling and condensing means for purifying solvent, and to return purified solvent to the system. Dye recovered on the filter or as residue from the distiUaticxi can be returned to the system for recycle. When a plurality of solvent cleaning tanks are employed, it is preferred to flow solvent countercurrently to the direction in which the articles being treated, are moved. The final component of the apparatus is the drying means, such as a hot air drier, from which articles leaving the system can be inspected and packaged.
• the drying means such as a hot air drier
• Solvent vapors from the hot air drier can be condensed and returned to the system.
• Fig. 1 is shown an apparatus, suitable for use in accordance with the invention.
• compositions of this invention will " be those wherein the aromatic ester is of the formula (ArCOO) -R,, Ar is phenyl or tolyl, 3 is the residue of glycerol, trimethylolpropane or pentaerythritol and the composition contains at least 5% by weight of an alkoxylated alkylphenol or an ester thereof. It is further preferred that the compositions of this invention contain at least 5% by weight of a diester, obtained from the hydrogenated adduet of linoleic acid and acrylic acid and that the organic colorant is a disperse dye.
• a most preferred process in accordance with this invention is one wherein the article being treated is exposed to the foregoing composition, maintained at a temperature of 140 - 235° C for a time adequate to achieve the desired degree of coloration.
• esters are prepared using the following reactants: (1) dipropylene glycol and benzoic acid, 1 : 2 molar ratio
• pentaerythritol and toluic acid 1 : 4 molar ratio
• trimethylolpropane and mixture of benzoic and toluic acids 1 : 3 molar ratio.
• Example 2 To a three-necked flask fitted out as in Example 1 was charged 750 g (1.1 moles) of polyoxyethylated nonylphenol (9.5 moles of oxyethylene, NP 9.5), 208 g (1 mole) of lauric acid and 2.4 g of p-toluenesulfonic acid. Air was purged from the flask with nitrogen and the mixture was heated to 160 - 170° C until an acid value below 10 g/KOH was obtained. The product was cooled and filtered.
• the product was cooled to 50 ® C and the catalyst was removed by filtration.
• Esters are prepared similarly from:
• Diacid 1550 and decyl alcohol, 1 : 2 molar ratio Diacid 1550 and tridecyl alcohol, 1 : 2 molar ratio
• a sample of the product had a hydroxyl value of 110 mg of KOH/g (15 moles of ethylene oxide added to the diacid.)
• the diester was acidified with acetic acid to neutralize the potassium hydroxide catalyst and treated with 3 g of hydrogen peroxide to bleach and lighten the color of the product.
• the reactor was cooled to 30° C prior to removing the product, which was filtered through filter paper, using a porcelain filter.
• Example 4A The product of Example 4A and 25 g of nickel on kieselguhr were charged to a stirred, heated pressure vessel. The mixture was heated to 160 - 170° C and pressurized with hydrogen to 400 psig. After 6 - 8 hours, samples were removed at intervals for determination of the iodine value. The reaction was continued until the iodine value was less than 0.5 g/100 g of sample.
• a propoxylated dibenzoate ester was prepared in a similar fashion.
• hypophosphorous acid 50%) The resulting mixture was heated and held at 165 -175° C until the theo ⁇ retical amount (37 g) of water was removed. Approximately 580 grams of benzyl laurate were recovered.
• benzyl esters of pelargonic, octanoic, palmitic, stearic, oleic and hydroxystearic acids were prepared in a similar fashion.
• Ethoxylated castor and hydrogenated castor oils were prepared as in Example 4. Ethylene oxide adds to the hydroxyl group of castor oil.
• a waterless dyeing composition was prepared from glyceryl tribenzoate (Velsicol Chemical Corp.) and nonylphenol 7 (7 oxyethylene units, Union Carbide Corp.) in 20 : 80 weight ratio, containing 1 gram/liter of presscake blue dye.
• This composition was kept at 180° C and stirred while a six-inch section of polyester zipper was immersed therein for one minute.
• the zipper was removed, washed in perchloroethylene and dried.
• the zipper was homogeneously colored with good dye fixation. There was little or no smoking during the coloring operation.
• buttons were homogeneously colored a light blue. At the end of three minutes, the buttons were deep blue. The buttons were washed with perchloroethylene as in
• compositions similar to those of Examples 9 and 10 were used to color the following articles, under the conditions indicated:
• a pump was used to circulate material in the dye bath during heating and while a polyester zipper about two feet long was immersed in the stirred bath for about 30 seconds.
• the zipper was removed from the bath and lightly squeezed with a roller to remove excess dye solution.
• the zipper was washed in a tank containing a mixture of trichloroethylene and perchloroethylene. After 30 seconds' immersion in the bath, the zipper was dried in a hot air chamber. The zipper was ready for final inspection and shipment. The zipper was rapidly dyed by this method and was pleasant in appearance.
• Dip dye solution is made from the following ingredients, as above: parts by weight
• the dip dye solution is used as in Examples 9-11 with similar results.

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• Medicinal Chemistry (AREA)
• Polymers & Plastics (AREA)
• Organic Chemistry (AREA)
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• Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)

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• 1983
  • 1983-11-10 GB GB08416539A patent/GB2140463B/en not_active Expired
  • 1983-11-10 EP EP19830903880 patent/EP0124606A4/de not_active Withdrawn
  • 1983-11-10 WO PCT/US1983/001760 patent/WO1984001972A1/en not_active Application Discontinuation
  • 1983-11-10 DE DE19833390325 patent/DE3390325T1/de not_active Withdrawn
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