US2950949A - Process for dyeing and printing shaped structures of hydrophobic organic high polymers containing ester groups - Google Patents

Process for dyeing and printing shaped structures of hydrophobic organic high polymers containing ester groups Download PDF

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US2950949A
US2950949A US654467A US65446757A US2950949A US 2950949 A US2950949 A US 2950949A US 654467 A US654467 A US 654467A US 65446757 A US65446757 A US 65446757A US 2950949 A US2950949 A US 2950949A
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Prior art keywords
dyeing
bath
grams
lactone
acid
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US654467A
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English (en)
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Schlack Paul
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Hoechst AG
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Hoechst AG
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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
    • D06P1/64—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)
    • 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
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
    • Y10S8/92—Synthetic fiber dyeing
    • Y10S8/922—Polyester fiber

Definitions

  • the present invention relates to a process for dyeing and printing shaped structures of hydrophobic organic high polymers containing ester groups.
  • dyeing has either to be carried out under pressure at temperatures considerably above 100 C. or dyeing auxiliaries, so-called carriers provoking a slight swelling of the compact fibre and thus opening it to the dyestutf molecules have to be added.
  • Dyeing under pressure requires expensive apparatuses. Moreover, it has to be taken into account that this process is not generally applicable. Thus, one will meet with difficulties when the textiles contain not only polyester filaments but also fibres that are very sensitive to heat. Difficulties are particularly great if the textiles contain wool, which especially when treated in a neutral bath, cannot be exposed to temperatures much above 100 C. This applies also to some synthetic fibres, for example, to fibres of polyvinyl alcohol. For the dyeing of piece-goods under pressure special devices are necessary which in practice have not yet become popular.
  • shaped structures of hydrophobic organic high polymers containing ester groups particularly of high-melting linear polyesters containing six-membered carbocyclic rings may be dyed and printed with dispersion dyestuffs if compounds that are sparingly or not at all soluble in water and contain one or more lactone groups in addition to at least one aromatic nucleus are used as auxiliaries.
  • dispersion dyestuffs there are preferably used compounds in which the lactone ring and an aromatic nucleus are joined by ortho-fusion (as the two rings in naphthalene). It proved to be suitable to select such compounds as do not contain more than two aromatic nuclei. It is furthermore of advantage to use compounds that are somewhat, even if sparingly soluble in water.
  • Dilactones may also be used.
  • lactones mentioned above may be employed for all the usual dyeing methods such as dyeing in flocks, dyeing in the rope form, dyeing in balls, piece-dyeing in the open vat, on the jig or on the dipping frame.
  • the lactones may furthermore be applied for the pad-dyeing process and for the continuous dyeing of cables and combed material. According to a prior suggestion these dyeing processes may be combined with a stretching process by impregnating the unstretched cable of filaments continuously with a dyestutf mixture containing, apart ingly volatile with steam, will be preferred.
  • auxiliary agent to be used for the dyeing or printing according to the present invention depends on the etficiency i.e. on the affinity to the fibre, which atlinity may in the case of water-soluble compounds be defined by the degree of distribution betweenbath and fibre. What amount is to be used depends moreover on the depth of shade which is desired, on the goods-to-liquor ratio applied and on the speed of difliusion in the fibre. It has to be taken into account in this connection that the pretreatment of the goods, especially the thermofixation also exerts an influence on the affinity of the swelling agents to the fibre.
  • the goods to be dyed may for example first be treated at an elevated temperature, at e.g. 80400 C. merely with the carrier, the dyestufif being added to the bath later on, or the material may be pretreated in a standing bath with a solution or a dispersion of the carrier in order to be subsequently dyed in a second bath to which, if necessary, a comparatively small amount of a carrier is added, which carrier need not be the same as that used in the bath of the pre-treatment.
  • thecarrier used in the dyebath proper has a greater efiiciency, i.e. a stronger aifiru'ty, and is added in a relatively smaller amount than the carrier used in the pretreatment bath.
  • the pretreatment bath may thus contain for example a methyl phthalide or, if a lower melting point is to be obtained, a mixture of methyl phthalides whereas a lactone of the naphthalene series is added to the dyebath.
  • the process of the present invention admits of dyeing in a single bath mixtures of fibres made of the polyesters coming into question and wool and other protein fibres, without any difficulties occurring with regard to the shading.
  • it is advisable to free the wool after the dyeing of the synthetic fibres first from the adhering dispersion dye stuff by way of a dithionite bath and then to dye the wool.
  • the usual auxiliary stripping agents may be used such as for example surface-active quaternary ammonium compounds or colloids having an aflinity to dyestuffs such as polyvinyl pyrrolidone or copolymers of vinyl pyrrolidone with other vinyl monomers such as acrylic acid.
  • the auxiliary agents used according to the present invention ditfer from the carrier substancesv hitherto customarily used in dispersions such as, for example, halogenated aromatic compounds or esters of aromatic carboxylic acids, by their more even effect which will especially be noticed when there is a distinct solubility in water. In the latter case the risk of stain formation is consider-ably diminished as the dyeing is brought about more gradually. Thus shading is facilitated.
  • a manner of proceeding according to the present invention which is especially advantageous in the case of textile goods showing a very dense style of weaving and being diflicult to dye in a uniform manner, is to use instead of the finished lactones the hydroxyacids, on which the corresponding lactones are based, in form of their salts, and to close the lactone ring during the dyeing process by acidifying the bath or by allowing it to become gradually acid and/or by means of a rise in temperature, whereupon dyestuff and lactone are absorbed by the fibre in a uniform manner, the lactone being more or less taken up in statu nascendi.
  • the present process is suitably carried out with hydroxyacids which are distinguished by a marked tendency to the ring closure, even in high dilution. Consequently, this modification of the process of the present inven tion is especially advantageous in the case of lactones that are sparingly soluble in water. If necessary, also in this case dyeing is carried out in the presence of dispersing agents, especially in the presence of anionic or non-ionic dispersing agents. 1
  • the ammonium salts of the hydroxyacids may for example be applied.
  • the alkali metal salts may also be used together with ammonium salts.
  • automatic acid formers, especially in conjunction with alkali metal salts there may also be added such compounds as are hydrolyzed by water into acids especially in the heat, as for example easily hydrolizable esters, such as oxamic acid esters or tartaric acid esters, imides such as phthalimide, salts of halogen-carboxylic acids that can easily be split such as sodium chloroacetate.
  • a gradual and cautious admixture of free acids such as formic acid, acetic acid or glycolic acid is of course also possible.
  • the proess of the present invention is preferably directed to the dyeing and printing of shaped structures made of hydrophobic organic high polymers containing ester groups, especially of shaped structures made of high-melting polyesters containing six-membered carbocyclic rings as for example the polyesters of terephthalic acid, it is as a general principle also applicable to other hydrophobic synthetic materials containing a variety of ester groups in the molecule and being difli cult to dye such as cellulose triacetate or linear polyurethanes.
  • shaped structures there come for example into consideration fibres, filaments, small ribbons, hanks, foils and materials made thereof such as textile fabrics.
  • Example 1 2.54 grams of the lactone of Z-hydroxy-naphthalenel-fi-propionic acid are added at a temperature of 60 C. to a dyebath containing in 875 cc. of water 2 grams of a condensation product from an alkyl phenol and ethylene oxide which condensation product was additionally esterified with sulfuric acid, 0.34 gram of the dispersion dyestuif of the formula and 1 cc. of an aqueous solution of glycolic acid of 33% strength.- 17 grams of yarn made of polyethylene glycol terephthalate (Nm 18/ 3, individual titre 3.6 deniers, staple length mm.) are introduced into the liquid which has become turbid by the dispersion of the lactone. The dyebath is slowly brought to the boil.
  • the bath quickly clarifies.
  • the dyeing is carried out for one hour at 97-98 C., during which time the bath is nearly exhausted. Subsequently the dyed material is thoroughly rinsed and washed for 20 minutes at C. in a bath containing 2 grams of soap and 1 gram of sodium carbonate per litre. A full shade of pink of a very good fastness to rubbing and washing is obtained.
  • Example 2 2.6 grams of 4.6-dimethyl-cumarin .dissolved in a small quantity of methanol are admixed at 60 C. to 1 litre of a dyebath containing 2 grams of a condensation product from an alkyl phenol and ethylene oxide which condensation product had additionally been esterified with sulfuric acid, 0.35 gram of the dyestufi of the formula OGHs (H) NH:
  • Example 3 4.5 grams of 6-methyl-phthalide are heated together with 15 cc. of a 2 N-methanolic sodium hydroxide solution 'until the lactone ring is completely opened. The solution thus obtained is then admixed at 60 C. to a dyebath containing in 900 cc.
  • Example 4 4.5 grams of 4.6-dimethyl-cumarin are heated together with 15 cc. of a 2 N-methanolic sodium hydroxide solution until the lactone ring is completely opened. The solution of the sodium dimethyl-cumarate is then admixed at 60 C. to a bath containing in 900 cc. of water 4 grams of ammonium chloride, 2 grams of a condensation product from an alkyl phenol and ethylene oxide which condensation product was additionally esterified with sulfuric acid, and 0.36 gram of the dyestuff mentioned in Example 3. After having introduced 18 grams of a fabric of polyethylene glycol terephthalate into the bath the latter is slowly heated to boiling and boiled for 20 minutes. By the addition of mineral acid the pH value of the bath is then adjusted to 5-6. Further dyeing and working up are carried out as described in Example 3. In this case, too, a clear deep blue shade of a very good fastness to Washing and rubbing is obtained.
  • Example 6 2.8 grams of the lactone of Z-hydroxynaphthalene-l-B- propionic acid dissolved in a small quantity of methanol are added while stirring to 1 litre of a bath containing 2 grams of a condensation product from an alkyl phenol and ethylene oxide which condensation product was additionally esterified with sulfuric acid, 1 cc. of glycolic acid of 33% strength and 0.425 gram of the dispersion dyestuff of the formula I l 02 i NH ⁇ Into the dull milky bath thus obtained there are then introduced 21.25 grams of a yarn made of polyethylene glycol terephthalate (Nm 48/2, 3.0 deniers, 100 mm., fixed in the dry state at C.) and the bath is slowly heatedto boiling. After a boiling time of l hour which suflices to practically exhaust the bath, the goods. are thoroughly rinsed and then washed at 90 C. as described in Examples 1-3.
  • the dyeing obtained has a good fastness to washing and rubbing.
  • Example 7 A concentrated solution of sodium dimethyl cumarate corresponding to 2.7 grams of 4.6-dimethyl-cumarin and 0.4 gram of dimethyl oxalate are added at 50 C. to a bath containing in 900 cc. of water 0.36 grain of the dyestutf of the formula ll 0 NH;
  • dyestuff was dispersed in a mixture of 0.036 gram of dibutyl-naphthalene-sulfonic acid and 0.36 gram of a dispersing agent that had been obtained by condensation of cresol, formaldehyde and sodium sulfite and by subsequently heating the product obtained with fl-naphthalene sulfonic acid, formaldehyde and sodium sulfite.
  • Example 4 After having introduced into the bath 18 grams of a fabric as has been described in Example 4 the bath is gradually heated to the boil and boiled for 10 minutes. Its pH value is then adjusted to 4.5 by means of acetic acid. The fabric is boiled for another 50 minutes and then completed in the way described in Example 3.
  • Example 8 2.1 grams of the dilactone of the formula (IZHs I OH and 6.9 grams of phthalimide serving as acid forming agent. After having introduced 14 grams of a fabric of polyethylene terephthalate into the bath the latter is slowly heated to the boil, whereby the previously suspended phthalimide dissolves. After 1 hours dyeing at boiling temperature the goods are thoroughly rinsed. A clear yellow dyein of medium depth and of good fastness to wet processing is obtained.
  • Example 9 A solution of sodium cumarate obtained by heating 2.2 grams of cumarin together with 0.65 grain of sodium hydroxide in a small quantity of methanol, is admixed at 45 C. to a dyebath containing in 750 cc. of water 0.3 gram of 1,4,5,S-tetra-arnino-anthraquinone and 1.5 grams of N-dimethyl-N-fl-hydroxyethyl-N-stearoylamido propylamrnonium-hydrogenphosphate and 1.45 grams of dimethyl oxalate. After addition of 14.9 grams of a poplin fabric of polyethylene terephthalate the bath is brought to the boil. After 1 hours boiling the goods are rinsed and soaped again at 70 C. A clear deep dyeing of a good fastness to wet processing is obtained.
  • a process for dyeing and printing shaped structures 35 of hydrophobic linear organic high polymers containing ester groups with dispersion dyestuffs which comprises dyeing said structures in the presence of an aromatic compound containing from one to two aromatic rings and substituted by from one to two lactone rings having from 5 to 6 ring members.
  • a process for dyeing and printing textile materials of hydrophobic linear high melting organic polyesters containing six-membered carbocyclic rings with dispersion dyestuffs which comprises dyeing said materials in a bath in the presence of an aromatic compound containing from one to two aromatic rings and substituted by from one to two lactone rings having from 5 to 6 ring mem: bers.
  • aromatic compound is the lactonc of Z-hydroxynaphthalenc- I-B-propionic acid.

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  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Chemical & Material Sciences (AREA)
  • Dispersion Chemistry (AREA)
  • Coloring (AREA)
  • Artificial Filaments (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
US654467A 1956-04-28 1957-04-23 Process for dyeing and printing shaped structures of hydrophobic organic high polymers containing ester groups Expired - Lifetime US2950949A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEF20175A DE1014962B (de) 1956-04-28 1956-04-28 Verfahren zum Faerben und Bedrucken von geformten Gebilden aus hydrophoben, organischen Hochpolymeren, die Estergruppen enthalten

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US2950949A true US2950949A (en) 1960-08-30

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US (1) US2950949A (enrdf_load_stackoverflow)
DE (1) DE1014962B (enrdf_load_stackoverflow)
FR (1) FR1174729A (enrdf_load_stackoverflow)
GB (1) GB860441A (enrdf_load_stackoverflow)
NL (2) NL216705A (enrdf_load_stackoverflow)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3980428A (en) * 1972-11-06 1976-09-14 Sandoz Ltd. Dyeing process
US4931067A (en) * 1987-03-27 1990-06-05 Sri International Method or dyeing using phase change dyestuffs
US5547478A (en) * 1992-12-22 1996-08-20 Sumitomo Chemical Company, Limited Compositions containing benzodifuranone compounds and methods for dyeing hydrophobic materials using the same

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1105837B (de) * 1958-04-05 1961-05-04 Bayer Ag Faerben von Polyesterfasermaterialien
DE1128978B (de) * 1958-07-12 1962-05-03 Hoechst Ag Verfahren zum Verformen von gefaerbten Kunstoffchips oder -granulaten zu Folien
US3072683A (en) * 1961-01-30 1963-01-08 Eastman Kodak Co 1-amino-4-sulfonamidoanthraquinone compounds comtaining an ether group in the 2-position
US4013690A (en) * 1974-02-05 1977-03-22 Sandoz Ltd. Organic compounds
EP0018947B1 (en) * 1979-05-04 1984-02-01 Ciba-Geigy Ag Dyeing composition and processes for dyeing fabrics made of polyester or a polyester blend with cotton or wool

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB645032A (en) * 1948-02-13 1950-10-25 Rowland Hill Solutions of aromatic polyesters

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB645032A (en) * 1948-02-13 1950-10-25 Rowland Hill Solutions of aromatic polyesters

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3980428A (en) * 1972-11-06 1976-09-14 Sandoz Ltd. Dyeing process
US4931067A (en) * 1987-03-27 1990-06-05 Sri International Method or dyeing using phase change dyestuffs
US5547478A (en) * 1992-12-22 1996-08-20 Sumitomo Chemical Company, Limited Compositions containing benzodifuranone compounds and methods for dyeing hydrophobic materials using the same

Also Published As

Publication number Publication date
NL216705A (enrdf_load_stackoverflow)
DE1014962B (de) 1957-09-05
NL101292C (enrdf_load_stackoverflow)
GB860441A (en) 1961-02-08
FR1174729A (fr) 1959-03-16

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