EP0000137A1 - Esters polyglycoliques; procédé de préparation et utilisation comme agents tensioactifs - Google Patents

Esters polyglycoliques; procédé de préparation et utilisation comme agents tensioactifs Download PDF

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Publication number
EP0000137A1
EP0000137A1 EP78100138A EP78100138A EP0000137A1 EP 0000137 A1 EP0000137 A1 EP 0000137A1 EP 78100138 A EP78100138 A EP 78100138A EP 78100138 A EP78100138 A EP 78100138A EP 0000137 A1 EP0000137 A1 EP 0000137A1
Authority
EP
European Patent Office
Prior art keywords
compounds according
printing
polyglycol esters
radical
ratio
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
EP78100138A
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German (de)
English (en)
Other versions
EP0000137B1 (fr
Inventor
Sienling Dr. Ong
Ulrich Dr. Cuntze
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Hoechst AG
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Hoechst AG
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from DE2728767A external-priority patent/DE2728767C3/de
Priority claimed from DE19772759204 external-priority patent/DE2759204A1/de
Application filed by Hoechst AG filed Critical Hoechst AG
Publication of EP0000137A1 publication Critical patent/EP0000137A1/fr
Application granted granted Critical
Publication of EP0000137B1 publication Critical patent/EP0000137B1/fr
Expired legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
    • C09K23/34—Higher-molecular-weight carboxylic acid esters
    • 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
    • C08G65/331—Polymers modified by chemical after-treatment with organic compounds containing oxygen
    • C08G65/332—Polymers modified by chemical after-treatment with organic compounds containing oxygen containing carboxyl groups, or halides, or esters thereof
    • C08G65/3322—Polymers modified by chemical after-treatment with organic compounds containing oxygen containing carboxyl groups, or halides, or esters thereof acyclic
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
    • 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
    • Y10S516/00—Colloid systems and wetting agents; subcombinations thereof; processes of
    • Y10S516/01—Wetting, emulsifying, dispersing, or stabilizing agents
    • Y10S516/06—Protein or carboxylic compound containing

Definitions

  • the invention relates to polyglycol esters of the formula I. in which R is an open-chain aliphatic radical having 9 to 19, preferably 11 to 17 C atoms, Z is hydrogen and methyl, the ratio H .: CH 3 2: 1 to 4: 1, preferably 2.5: 1 to 3.5: 1, a is zero or 1, b is 1 to 1.5 and (4-a) 'n is 150 to 300, preferably 200 to 250.
  • polyglycol esters in which the radical R-CO is oleyl, the ratio of H: CH 3 in the radical Z 3: 1 is random, a is zero, b is 1.1 and (4-a) ' n is about 210.
  • the invention further relates to a process for the preparation of said polyglycol esters, which is characterized in that a compound of the formula in which a is zero or 1, with 150-300 times, preferably 200-250 times, in particular about 210 times molar amount of a mixture of: ethylene oxide and propylene oxide in a molar ratio of 2: 1 to 4: 1 and the oxyalkylate with one the rest R-CO introducing partially esterified acylating agent.
  • Such acylating agents are natural or synthetic fatty acids such as, for example, stearic acid, palmitic acid, oleic acid, linolenic acid, tallow fatty acid, tall oil fatty acid, isostearic acid, coconut fatty acid or mixtures of such acids, and the corresponding acid chlorides.
  • the invention further relates to the use of the new polyglycol esters as surface-active agents.
  • the new polyglycol esters are particularly suitable for increasing or stabilizing the viscosity of aqueous systems, in particular as an additive to printing pastes or padding liquors.
  • the polyglycol esters are added in amounts of about 0.1 to about 10%, based on the weight of the finished preparation, that is to say about 1 to 100 g, preferably 2 to 30 g, of polyglycol esters per kg of printing paste.
  • Aqueous preparations of the polyglycol esters according to the invention can already be used as thickeners without further additives be used.
  • the new poly g lykolester as additives to other known thickeners, where they not only increase the viscosity of aqueous systems, but can especially stabilize.
  • a thickener As is well known, a whole range of tasks are assigned to a thickener: it must counteract the outflow of dye solutions caused by the capillary forces of the tissue. Furthermore, it prevents the R ouleaux horr the tendency of the ink to leak to the law of gravity, following from the engravings of the rotating platen.
  • the thickening ku ngsmittel continues to offer the possibility of various reactants in a printing ink accommodate that early in his absence, that is already in the printing ink and not only on the fiber would react.
  • the thickener acts as a "spacer" and prevents the premature interaction of reactive components. For example, tannin can be accommodated in a printing ink of a cationic dye without the formation of the tannin varnish, which should only take place when the fibers are steamed.
  • the thickening agent also has the task of keeping such substances in a homogeneous dispersion and ensuring that the pigment does not settle in the engravings of the rollers, but rather homogeneously with the printing ink on the Goods arrived.
  • the selection of a thickener is directed by a variety of factors. Among other things, by the type of printing process, by the composition of the printing ink, by the depth of the roller engraving and the required depth of color of the print, by the quality of the goods, especially if there is a requirement for a print run, and also by the type of pattern, i.e. whether small or. large-area patterns (register or decker) are to be printed.
  • the polyglycol esters according to the invention are particularly suitable as an additive to purely synthetic thickeners, in particular those which contain carboxyl groups.
  • such as dialkyl maleic esters or ethylene glycol dimethacrylic esters can be cross-linked.
  • the polyglycol ethers according to the invention are also suitable as additives for oil-in-water and water-in-oil emulsions and their mixtures with native thickeners.
  • the polyglycol esters according to the invention can not only increase or stabilize the viscosity, but also allow the viscosity to be restored to a system which has been damaged, for example, by the influence of electrolytes.
  • the compounds of the formula I can also be used as emulsifiers.
  • the compounds of the formula I are preferably used for the preparation of dye emulsions which are used for dyeing and printing textiles. These emulsions show an extraordinarily good penetration into the textiles, so that uniform, deep dyeings with good fastness properties result.
  • the emulsion thickenings customary hitherto have a number of disadvantages: Because of the relatively low emulsifying action of the conventional emulsifiers, quite large amounts of these surface-active agents were required, which often led to excessive foaming when the emulsions were prepared. Usual defoamers, however, as used in the textile industry, can change the stability and effectiveness of the printing pastes. In particular, there is a danger that defoaming components may occur breaking of the emulsion through the 'additive that is, the already finished emulsions are broken again.
  • the emulsifiers according to the invention show significant advantages compared to the commercially available products: the usual water-swellable thickeners, namely alginates, core meal ether, starch ether or carboxymethyl cellulose, contain more or less significant amounts of alkali ions which, as electrolytes, can break emulsions.
  • a half emulsion thickeners are most often used for printing pastes with reactive, disperse and acid dyes and these dyes either themselves electrolytes or in their commercially available preparations electrolytes, this problem has been through the use of correspondingly large amounts of trying to solve of emulsifiers.
  • These high amounts of emulsifier not only brought with them the disadvantages already described above, but also often led to a reduction in the brilliance of the prints.
  • the emulsifiers according to the invention are considerably less sensitive to electrolytes than the products customary hitherto. In the case of half emulsions, small amounts of emulsifier are therefore sufficient.
  • An emulsion thickening obtained in accordance with the present invention contains, based on the weight of the finished emulsion thickening, 0.1 to 2, preferably 0.2 to 1% of compounds of the formula I, 50 to 70% of the water-immiscible solvents and 28 to 49, 9% water.
  • Solvents which are immiscible with water are mainly hydrocarbons such as hexanes, heptanes, nonanes, cyclohexylbenzene, toluene, xylene, tetrahydronaphthalene and gasolines or mixtures of such solvents.
  • Emulsionsverdickun g en printing pastes prepared further contain colorants, especially pigments, and binders. If necessary, this pressure pastes also contain acid donors such as diammonium hydrogen phosphate.
  • the printing pastes prepared with the emulsions according to the invention result in very level and brilliant prints with very good stability.
  • These printing pastes are particularly suitable for pigment printing on cotton, rayon and other natural and also synthetic fibers and their mixtures, in particular on mixtures of natural and synthetic fibers.
  • the emulsion thickeners according to the invention are also suitable in a mixture with water-swellable thickeners, such as alginates, core meal ethers, starch ethers or carboxymethyl celluloses, for printing pastes with dyes, for example disperse dyes, reactive dyes and acid dyes.
  • the emulsions according to the invention can be prepared by stirring the oily and aqueous phases together with the emulsifier or by other customary processes known from the literature (P. Becker, Emulsions: Theory and Practice, Reinhold Publishing Corp., New York, 1957, p. 209, Houben-Weyl, Ed. I 2, p. 97). It proves to be advantageous here that the compounds of the formula I are water-soluble so that they can be used as aqueous solutions for the preparation of the emulsions.
  • emulsions can be produced with the emulsifiers according to the invention.
  • an oily phase in addition to said organic water-immiscible solvents, anti-aging agents, plasticizers and other auxiliaries for the rubber industry, biological active substances in crop protection, H ilfs- medium in dyeing, textile and leather processing sector and in polymerization, in particular for emulsion polymerization are preferably used.
  • the dot-dash curve was obtained with printing paste A, the solid curve with printing paste B and the dash-dash curve with printing paste C.
  • the rheogram shows that the viscosity of printing paste A with the dash-dot flow curve decreases sharply due to the addition of an electrolyte (printing paste B with the continuous flow curve).
  • polyglycol ester This product is referred to briefly as "polyglycol ester" in the following examples. These examples describe the use of the polyglycol ester as an emulsifier.
  • M an receives an easily processable, low-foaming pigment printing paste.
  • a cotton poplar fabric is printed with this printing paste, dried and fixed at 150 ° C for 7 minutes. You get brilliant red prints with very good rub fastness.
  • This low-foam, easy-to-process printing paste is used to print a fabric made of cellulose, dry it, fix it in saturated steam for 5 minutes and wash it. After a less thorough rinsing and washing process, the fabric no longer contains any thickener residues. After drying, the high brilliance of the yellow prints becomes clearer.
  • a fabric made of polyethylene glycol terephthalate is made up of a printing paste printed, dried, fixed in hot air at 2 00 ° C for 1 minute and washed after a reductive treatment.
  • An emulsion is prepared by stirring with a turbo stirrer at room temperature for 5-10 minutes
  • the mixture is stirred at 95 ° C. for a further 2 hours.
  • a polymer emulsion is obtained which is practically free of coarse and fine coagulate.
  • the conversion of the monomers is 95%.
  • a polymer emulsion is obtained which is free of coarse or fine deposits, the monomer conversion is 100%.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • General Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Coloring (AREA)
  • Inks, Pencil-Leads, Or Crayons (AREA)
  • Polyethers (AREA)
EP78100138A 1977-06-25 1978-06-12 Esters polyglycoliques; procédé de préparation et utilisation comme agents tensioactifs Expired EP0000137B1 (fr)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
DE2728767A DE2728767C3 (de) 1977-06-25 1977-06-25 Polyglykolester, Verfahren zu ihrer Herstellung und ihre Verwendung zur Erhöhung der Viskosität wäßriger Systeme
DE2728767 1977-06-25
DE2759204 1977-12-31
DE19772759204 DE2759204A1 (de) 1977-12-31 1977-12-31 Verwendung von polyglykolestern als emulgatoren

Publications (2)

Publication Number Publication Date
EP0000137A1 true EP0000137A1 (fr) 1979-01-10
EP0000137B1 EP0000137B1 (fr) 1982-03-24

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Family Applications (1)

Application Number Title Priority Date Filing Date
EP78100138A Expired EP0000137B1 (fr) 1977-06-25 1978-06-12 Esters polyglycoliques; procédé de préparation et utilisation comme agents tensioactifs

Country Status (5)

Country Link
US (1) US4209333A (fr)
EP (1) EP0000137B1 (fr)
JP (1) JPS5411200A (fr)
DE (1) DE2861683D1 (fr)
IT (1) IT1097277B (fr)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0028342A2 (fr) * 1979-10-31 1981-05-13 Hoechst Aktiengesellschaft Utilisation de composés polyoxalkylés estérifiés comme adjuvants de préparations tinctoriales et préparations tinctoriales correspondantes
US4382013A (en) * 1980-02-19 1983-05-03 Basf Wyandotte Corporation Anionic surfactant compositions effective in aqueous solutions of strongly ionizable salts
EP0264826A2 (fr) * 1986-10-23 1988-04-27 Henkel Kommanditgesellschaft auf Aktien Esters d'acides gras de polyglycérine-polyglycole-éthers, leur préparation et leur utilisation
US5331451A (en) * 1991-07-06 1994-07-19 Alcatel N.V. Optical time-division multiplexing
WO2014014125A1 (fr) * 2012-07-20 2014-01-23 Fujifilm Corporation Procédé de gravure, procédé de production d'un substrat semi-conducteur et dispositif à semi-conducteur l'utilisant

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2912497C3 (de) * 1979-03-29 1982-04-15 Hoechst Ag, 6000 Frankfurt Verfahren und Mittel zum Colorieren von Textilien aus Polyesterfasern
DE2915643A1 (de) * 1979-04-18 1980-11-06 Licentia Gmbh Elastische abdeckung aus einem elastomeren material
JPS5836276A (ja) * 1981-08-25 1983-03-03 三洋化成工業株式会社 捺染用助剤および捺染方法
US4426485A (en) 1982-06-14 1984-01-17 Union Carbide Corporation Polymers with hydrophobe bunches
US4496708A (en) * 1983-12-14 1985-01-29 Union Carbide Corporation Water-soluble polyurethane comb polymer production
DE3526790A1 (de) * 1985-07-26 1987-01-29 Bayer Ag Ether- und ethergruppen aufweisende polyhydroxylverbindungen und ihre verwendung als aufbaukomponente bei der herstellung von polyurethankunststoffen, insbesondere als polyolkomponente in polyurethan-beschichtungsmitteln oder -vergussmassen
US5192462A (en) * 1989-03-21 1993-03-09 Croda Inc. Thickening agents for topical preparations
US5759369A (en) * 1992-09-24 1998-06-02 The Perkin-Elmer Corporation Viscous electrophoresis polymer medium and method
US5290418A (en) * 1992-09-24 1994-03-01 Applied Biosystems, Inc. Viscous electrophoresis polymer medium and method
EP2301645A1 (fr) * 2009-09-28 2011-03-30 Cytec Surface Specialties Austria GmbH Antimoussant pour la pulvérisation sans air
GB201408823D0 (en) * 2014-05-19 2014-07-02 Croda Int Plc Demulsifiers

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2457139A (en) * 1946-02-26 1948-12-28 Carbide & Carbon Chem Corp Esters of polyoxyalkylene diols
DE1595369A1 (de) * 1966-12-15 1970-04-09 Basf Ag Derivate von Blockcopolymerisaten des AEthylenoxyds und des 1,2-Propylenoxyds und Verfahren zu deren Herstellung
CH490489A (de) * 1967-04-19 1970-05-15 Prols Fabrik Ab Flüssiges Wasch- und Reinigungsmittel
DE1619053A1 (de) * 1967-08-10 1970-09-17 Bayer Ag Verfahren zur Behandlung von Polyester-Fasermaterialien
DE2102899A1 (de) * 1971-01-22 1972-08-10 Badische Anilin- & Soda-Fabrik Ag, 6700 Ludwigshafen Schaumarme wasserlösliche Färbereihilfsmittel
FR2156022A1 (fr) * 1971-10-04 1973-05-25 Mo Och Domsjoe Ab

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NL272723A (fr) * 1951-05-31
US2911434A (en) * 1956-04-24 1959-11-03 Visco Products Co Surface active dicarboxylic acid esters of polyalkylene oxides
US2987490A (en) * 1956-09-17 1961-06-06 Visco Products Co Surface-active esters of polymerized polyethenoid fatty acids
US2969388A (en) * 1957-01-24 1961-01-24 Rohm & Haas Surface-active monoesters
US2950313A (en) * 1957-07-02 1960-08-23 Visco Products Co Surface active polyoxypropylene esters
US2950299A (en) * 1958-01-06 1960-08-23 Visco Products Co Surface active substances of ether ester class
GB1201091A (en) * 1967-08-19 1970-08-05 Geigy Uk Ltd Oxetane polymer derivatives
US3637523A (en) * 1968-09-12 1972-01-25 Scm Corp Esters of glycerol and polyhydric alcohol copolymers useful as emulsifying agents and process for their production
JPS5344551B2 (fr) * 1974-03-12 1978-11-29

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2457139A (en) * 1946-02-26 1948-12-28 Carbide & Carbon Chem Corp Esters of polyoxyalkylene diols
DE1595369A1 (de) * 1966-12-15 1970-04-09 Basf Ag Derivate von Blockcopolymerisaten des AEthylenoxyds und des 1,2-Propylenoxyds und Verfahren zu deren Herstellung
CH490489A (de) * 1967-04-19 1970-05-15 Prols Fabrik Ab Flüssiges Wasch- und Reinigungsmittel
DE1619053A1 (de) * 1967-08-10 1970-09-17 Bayer Ag Verfahren zur Behandlung von Polyester-Fasermaterialien
DE2102899A1 (de) * 1971-01-22 1972-08-10 Badische Anilin- & Soda-Fabrik Ag, 6700 Ludwigshafen Schaumarme wasserlösliche Färbereihilfsmittel
FR2156022A1 (fr) * 1971-10-04 1973-05-25 Mo Och Domsjoe Ab

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0028342A2 (fr) * 1979-10-31 1981-05-13 Hoechst Aktiengesellschaft Utilisation de composés polyoxalkylés estérifiés comme adjuvants de préparations tinctoriales et préparations tinctoriales correspondantes
EP0028342A3 (en) * 1979-10-31 1981-11-11 Hoechst Aktiengesellschaft Use of polyoxyalkyl esters as preparatory agents for dyestuffs and corresponding dyestuff preparations
US4382013A (en) * 1980-02-19 1983-05-03 Basf Wyandotte Corporation Anionic surfactant compositions effective in aqueous solutions of strongly ionizable salts
EP0264826A2 (fr) * 1986-10-23 1988-04-27 Henkel Kommanditgesellschaft auf Aktien Esters d'acides gras de polyglycérine-polyglycole-éthers, leur préparation et leur utilisation
EP0264826A3 (en) * 1986-10-23 1989-03-15 Henkel Kommanditgesellschaft Auf Aktien Fatty acid esters of polyglycerinpolyglycol ethers, their production and their use
US5331451A (en) * 1991-07-06 1994-07-19 Alcatel N.V. Optical time-division multiplexing
WO2014014125A1 (fr) * 2012-07-20 2014-01-23 Fujifilm Corporation Procédé de gravure, procédé de production d'un substrat semi-conducteur et dispositif à semi-conducteur l'utilisant

Also Published As

Publication number Publication date
EP0000137B1 (fr) 1982-03-24
US4209333A (en) 1980-06-24
DE2861683D1 (en) 1982-04-29
IT7824934A0 (it) 1978-06-23
IT1097277B (it) 1985-08-31
JPS5411200A (en) 1979-01-27

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