CH355457A - Process for the preparation of compounds which can be used as leveling and stripping agents - Google Patents
Process for the preparation of compounds which can be used as leveling and stripping agentsInfo
- Publication number
- CH355457A CH355457A CH355457DA CH355457A CH 355457 A CH355457 A CH 355457A CH 355457D A CH355457D A CH 355457DA CH 355457 A CH355457 A CH 355457A
- Authority
- CH
- Switzerland
- Prior art keywords
- compounds
- leveling
- agents
- phosphating
- stripping agents
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims description 6
- 238000000034 method Methods 0.000 title claims description 6
- 238000002360 preparation method Methods 0.000 title description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 13
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 10
- 229920000151 polyglycol Polymers 0.000 claims description 7
- 239000010695 polyglycol Substances 0.000 claims description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 150000002170 ethers Chemical class 0.000 claims description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 230000001180 sulfating effect Effects 0.000 claims description 4
- 150000003014 phosphoric acid esters Chemical class 0.000 claims description 3
- 230000019635 sulfation Effects 0.000 claims description 3
- 238000005670 sulfation reaction Methods 0.000 claims description 3
- YKYIFUROKBDHCY-ONEGZZNKSA-N (e)-4-ethoxy-1,1,1-trifluorobut-3-en-2-one Chemical group CCO\C=C\C(=O)C(F)(F)F YKYIFUROKBDHCY-ONEGZZNKSA-N 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000001033 ether group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 description 11
- 238000004043 dyeing Methods 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000000975 dye Substances 0.000 description 6
- 239000000047 product Substances 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 4
- -1 fatty acid nitriles Chemical class 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical group OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 3
- REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical compound CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 239000007859 condensation product Substances 0.000 description 3
- 239000000434 metal complex dye Substances 0.000 description 3
- NYGZLYXAPMMJTE-UHFFFAOYSA-M metanil yellow Chemical group [Na+].[O-]S(=O)(=O)C1=CC=CC(N=NC=2C=CC(NC=3C=CC=CC=3)=CC=2)=C1 NYGZLYXAPMMJTE-UHFFFAOYSA-M 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 2
- FJLUATLTXUNBOT-UHFFFAOYSA-N 1-Hexadecylamine Chemical compound CCCCCCCCCCCCCCCCN FJLUATLTXUNBOT-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 2
- 150000004985 diamines Chemical class 0.000 description 2
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- NVVZQXQBYZPMLJ-UHFFFAOYSA-N formaldehyde;naphthalene-1-sulfonic acid Chemical compound O=C.C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 NVVZQXQBYZPMLJ-UHFFFAOYSA-N 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 2
- 210000002268 wool Anatomy 0.000 description 2
- QGLWBTPVKHMVHM-KTKRTIGZSA-N (z)-octadec-9-en-1-amine Chemical compound CCCCCCCC\C=C/CCCCCCCCN QGLWBTPVKHMVHM-KTKRTIGZSA-N 0.000 description 1
- IXKVYSRDIVLASR-UHFFFAOYSA-N 2,3-dioctylphenol Chemical compound CCCCCCCCC1=CC=CC(O)=C1CCCCCCCC IXKVYSRDIVLASR-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 1
- 208000032843 Hemorrhage Diseases 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 229920000388 Polyphosphate Polymers 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 208000034158 bleeding Diseases 0.000 description 1
- 230000000740 bleeding effect Effects 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 239000005018 casein Substances 0.000 description 1
- BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 1
- 235000021240 caseins Nutrition 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 150000004696 coordination complex Chemical class 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical compound CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 239000002657 fibrous material Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- GXMVXAAQVWCSRQ-UHFFFAOYSA-N n,n-bis(2-aminoethyl)octadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(=O)N(CCN)CCN GXMVXAAQVWCSRQ-UHFFFAOYSA-N 0.000 description 1
- KKBOOQDFOWZSDC-UHFFFAOYSA-N n-[2-(diethylamino)ethyl]octadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(=O)NCCN(CC)CC KKBOOQDFOWZSDC-UHFFFAOYSA-N 0.000 description 1
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 1
- HKUFIYBZNQSHQS-UHFFFAOYSA-N n-octadecyloctadecan-1-amine Chemical compound CCCCCCCCCCCCCCCCCCNCCCCCCCCCCCCCCCCCC HKUFIYBZNQSHQS-UHFFFAOYSA-N 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000001205 polyphosphate Substances 0.000 description 1
- 235000011176 polyphosphates Nutrition 0.000 description 1
- 229920006306 polyurethane fiber Polymers 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/44—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders
- D06P1/60—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders using compositions containing polyethers
- D06P1/607—Nitrogen-containing polyethers or their quaternary derivatives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Coloring (AREA)
Description
Verfahren zur Herstellung von als Egalisier- und Abziehmittel verwendbaren Verbindungen
Die vorliegende Erfindung betrifft ein Verfahren zur Herstellung von als Egalisier- und Abziehmittel verwendbaren Verbindungen, das durch gekennzeichnet ist, dass man auf veresterbare Polyglykol ätherverbindungen, welche im Molekül mindestens a) ein basisches Stickstoffatom, b) einen lipophilen Rest, der zur Hauptsache oder ganz aus Kohlenstoff- und Wasserstoffatomen besteht und mindestens 10 Kohlenstoffatome aufweist, c) eine Polyglykolätherkette mit mindestens 4 Athoxygruppen enthalten, Sulfatierungs- oder Phosphatierungsmittel einwirken lässt, wobei die entsprechenden Schwefelsäure- oder Phosphorsäureester gebildet werden, und mindestens ein quaternierbares Stickstoffatom vor oder nach der Sulfatierung bzw.
Phosphatierung quaterniert.
Die so hergestellten Verbindungen eignen sich in der Färberei von natürlichen und synthetischen stickstoffhaltigen Fasern, wie Wolle, Seide, Casein-, Polyamid- und Polyurethanfasern oder von Gemischen aus solchen mit sich selbst oder mit Baumwolle, insbesondere aber von Wolle, mit sulfonsäure und carboxylgruppenfreien Metallkomplexfarbstoffen, welche weniger als 2 Metallatome an 2 Moleküle des den Metallkomplex bildenden Monoazofarbstoffes komplex gebunden enthalten.
Zur Herstellung der in die Schwefelsäure- oder Phosphorsäureester überzuführenden Ausgangsstoffe kann man beispielsweise von höhermolekularen Aminen, z. B. von solchen Aminen ausgehen, die aus höhermolekularen Fettsäurenitrilen durch katalytische Hydrierung gewonnen und als Fettamine be zeichnet werden, und an diese pro Mol 4-120, vorzugsweise 10-60 Mol, Äthylenoxyd anlagern. Die erhaltenen Oxäthylierungsprodukte können dann durch Einwirkung von Sulfierungs- oder Phosphatierungsmitteln in die entsprechenden Sulfate, Phosphate bzw. Polyphosphate übergeführt werden.
Anstelle von Äthylenoxyd können auch reaktionsfähige Halogenatome enthaltende Polyäthylenglykoläther auf die Amine zur Einwirkung gebracht werden.
Geeignete Amine sind beispielsweise Dodecylamin, Cetylamin, Stearylamin und Oleylamin, Harz amine, N-Monoalkylpropylendiamin-(1, 3), dessen Alkylrest beispielsweise der Cetyl- oder Stearylrest sein kann,
N-(Di-isooctylphenoxy-äthoxy-äthyl)-N'-oxy äthyl-äthylendiamin,
2-Heptadecyl-N-oxyäthyl-imidazolin,
Oleoyläthylendiamin, Monostearoyldiäthylentriamin,
Distearoyl-diäthylentriamin,
Dioleoyl-tetraäthylenpentamin,
N-Stearoyl-N', N'-diäthyläthylendiamin,
N-Cetoxyäthyl-N,N',N'-trioxyäthyläthylendiamin,
Dicocosylamin,
Distearylamin.
Es ist auch möglich, zur Herstellung der zu veresternden Ausgangsstoffe von stickstofffreien Polyglykolätherverbindungen auszugehen, z. B. von Anlagerungsprodukten von beispielsweise 10-60 Mol Äthylenoxyd an Stearylalkohol oder an Dioctylphenol, und diese, beispielsweise über ihre sauren Schwefelsäureester, mit geeigneten Aminen, z. B. mit Oxäthyläthylendiamin, nach bekannten Methoden zu entsprechenden Aminoverbindungen umzusetzen. Auf diese Ausgangsstoffe lässt man dann, gegebenenfalls nach weiterer Oxäthylierung, in beliebiger Reihenfolge einerseits Sulfatierungs- oder Phosphatierungsmittel und anderseits Quaternierungsmittel einwirken.
Die erfindungsgemäss erhaltenen Produkte sind von ölig- bis wachsartiger Konsistenz und gut wasserlöslich. Sie können in alkalischem, neutralem oder saurem Milieu als Egalisier- und Abziehmittel verwendet werden.
Es ist bekannt, dass beim Färben mit sulfonsäure und carboxylgruppenfreien Metallkomplexfarbstoffen, welche weniger als 2 Metallatome an 2 Moleküle Monoazofarbstoff komplex gebunden enthalten, die Egalität der Färbung, besonders im sauren Bad, zu wünschen übrig lässt. Deshalb wurde schon empfohlen, in Gegenwart von Egalisiermitteln zu färben und als solche die Einwirkungsprodukte von Ähylenoxyd auf Fettalkohole bzw. Fettamine, oder aberNaphthalinsulfonsäure-Formaldehydkonden- sationsprodükte zu verwenden. Die erwähnten Äthylenoxydkondensationsprodukte weisen jedoch den Nachteil auf, dass ihre Mitverwendung zu Fällungen im Färbebad oder zur Entstehung von abblutenden oder reibunechten Färbungen Anlass geben kann.
Die Naphthalinsulfonsäure - Form aldehydkondensations- produkte hingegen zeigen nur geringe Egalisierwirkung.
Es wurde nun gefunden, dass die erfindungsgemäss hergestellten Verbindungen diese Nachteile nicht aufweisen.
Die Anwendung derselben kann im pH-Bereich von etwa 3-7 erfolgen, das heisst in Abwesenheit oder in Gegenwart von beispielsweise Schwefelsäure, Phosphorsäure, Ameisensäure, Essigsäure oder von Puffermischungen. Ferner können Neutralsalze, z. B.
Natriumsulfat oder Natriumchlorid, zugegen sein.
Die zu verwendende Egalisier- und Abziehmittelmenge hat sich nach den jeweils vorliegenden färberischen Verhältnissen zu richten, z. B. nach der Art und der Menge des Farbstoffes und nach dem Charakter und dem Verarbeitungszustand des Fasermaterials. Sie beträgt beispielsweise 0,2-3 0/o des Warengewichtes. Die Hilfsmittel können dem Färbebad vor Beginn oder im Laufe der Färbung zugesetzt werden.
Sie können für sich allein dem Färbebad zugesetzt werden oder in Kombination mit andern Egalisier- und Abziehmitteln, wie beispielsweise Alkyloder Fettaminpolyglykoläthern verwendet werden.
Das färberisch zu behandelnde Textilmaterial kann in beliebiger Form vorliegen, das heisst z. B. als Gewebe, als Garn oder lose. Seiner Zusammensetzung nach kann es aus einer einzigen Faserart oder aus Mischungen von solchen bestehen.
Die erfindungsgemäss hergestellten Hilfsmittel eignen sich besonders beim Färben mit sulfonsäureund carboxylgruppenfreien Metallkomplexfarbstoffen, welche weniger als 2 Metallatome an 2 Moleküle Monoazofarbstoff komplex gebunden enthalten, vor allem mit solchen, die im wesentlichen 1 Metallatom an 2 Moleküle Monoazoverbindung komplex gebunden enthalten.
In den nachfolgenden Beispielen bedeuten T.
Gewichtsteile.
Beispiel 1
An 310 T. eines technischen Amingemisches, das etwa 850/0 primäre Amine enthält, die aus etwa 300/o Cetylamin, etwa 25 /o Octadecylamin und etwa 450/0 Octadecylamin bestehen, werden bei 130 bis 1700 in Gegenwart von 1,5 T. im Amingemisch feinst verteiltem Natriumhydroxyd 880 T. Athylenoxyd angelagert.
Zu 129 T. des entstandenen Polyglykoläthergemisches werden im Laufe von 15 Minuten bei 40 bis 600 13,2 T. Dimethylsulfat zugetropft. Nach der Zugabe wird die Temperatur während 60 Minuten bei 70-80" gehalten. Hierauf kühlt man ab und tropft bei 45-50 im Laufe von 10 Minuten eine Lösung aus 23,4 T. Chlorsulfonäure und 200 T.
Chloroform zu. Anschliessend wird das Chloroform im Vakuum abgedampft und der Rückstand mit 3n Natronlauge neutralisiert.
Beispiel 2
128 T. des Anlagerungsproduktes von 880 T.
Athylenoxyd an 400 T. des im Handel erhältlichen Diamins der allgemeinen Formel R-NH(CH2)3NH2, in welchem R eine sich vom Talg ableitende höhere Alkylgruppe bedeutet, das in einem Reinheitsgrad von etwa 804/o, berechnet als Diamin, vorliegt und einen Schmelzbereich von etwa 44 180 aufweist, werden gemäss den Angaben des Beispiels 1 mit 25,2 T. Chlorsulfonsäure umgesetzt. Das Sulfatierungsprodukt wird hierauf mit Sodalösung phenolphthalin-alkalisch gestellt. Anschliessend lässt man unter Rühren bei 60-700 13,0 T. Dimethylsulfat zutropfen. Das erhaltene quaternäre Ammoniumgruppen aufweisende Schwefel säureestergemisch eignet sich als Egalisier- und Abziehmittel.
Process for the preparation of compounds which can be used as leveling and stripping agents
The present invention relates to a process for the preparation of compounds which can be used as leveling and stripping agents, which is characterized in that esterified polyglycol ether compounds which contain at least a) one basic nitrogen atom in the molecule, b) a lipophilic radical, which is mainly or entirely consists of carbon and hydrogen atoms and has at least 10 carbon atoms, c) contain a polyglycol ether chain with at least 4 ethoxy groups, allows sulfating or phosphating agents to act, the corresponding sulfuric or phosphoric acid esters being formed, and at least one quaternizable nitrogen atom before or after sulfation or .
Quaternized phosphating.
The compounds produced in this way are suitable in the dyeing of natural and synthetic nitrogen-containing fibers such as wool, silk, casein, polyamide and polyurethane fibers or of mixtures of such with themselves or with cotton, but especially of wool with sulfonic acid and carboxyl group-free metal complex dyes which contain less than 2 metal atoms bound to 2 molecules of the monoazo dye forming the metal complex.
To prepare the starting materials to be converted into the sulfuric acid or phosphoric acid esters, one can use, for example, higher molecular weight amines, e.g. B. start from such amines, which are obtained from higher molecular weight fatty acid nitriles by catalytic hydrogenation and are characterized as fatty amines be, and add to this per mole of 4-120, preferably 10-60 mol, ethylene oxide. The oxyethylation products obtained can then be converted into the corresponding sulfates, phosphates or polyphosphates by the action of sulfating or phosphating agents.
Instead of ethylene oxide, polyethylene glycol ethers containing reactive halogen atoms can also be brought to act on the amines.
Suitable amines are, for example, dodecylamine, cetylamine, stearylamine and oleylamine, resin amines, N-monoalkylpropylenediamine (1, 3), the alkyl radical of which can be, for example, the cetyl or stearyl radical,
N- (Di-isooctylphenoxy-ethoxy-ethyl) -N'-oxy-ethyl-ethylenediamine,
2-heptadecyl-N-oxyethyl-imidazoline,
Oleoylethylenediamine, monostearoyldiethylenetriamine,
Distearoyl diethylenetriamine,
Dioleoyl tetraethylene pentamine,
N-stearoyl-N ', N'-diethylethylenediamine,
N-cetoxyethyl-N, N ', N'-trioxyethylethylenediamine,
Dicocosylamine,
Distearylamine.
It is also possible to use nitrogen-free polyglycol ether compounds to prepare the starting materials to be esterified, e.g. B. of addition products of, for example 10-60 mol of ethylene oxide with stearyl alcohol or with dioctylphenol, and these, for example via their acidic sulfuric acid esters, with suitable amines, e.g. B. with Oxäthyläthylenediamine, to implement the corresponding amino compounds by known methods. These starting materials are then allowed to act in any order, on the one hand sulfating or phosphating agents and on the other hand quaternizing agents, if necessary after further oxyethylation.
The products obtained according to the invention have an oily to waxy consistency and are readily soluble in water. They can be used as leveling and stripping agents in an alkaline, neutral or acidic medium.
It is known that when dyeing with sulfonic acid and carboxyl group-free metal complex dyes which contain less than 2 metal atoms bound to 2 molecules of monoazo dye complex, the levelness of the dyeing leaves something to be desired, especially in an acidic bath. It has therefore already been recommended to dye in the presence of leveling agents and as such to use the action products of ethylene oxide on fatty alcohols or fatty amines, or else naphthalenesulfonic acid-formaldehyde condensation products. The abovementioned ethylene oxide condensation products have the disadvantage, however, that their use can give rise to precipitations in the dyebath or to the development of bleeding or non-rubbing dyeings.
The naphthalenesulfonic acid - formaldehyde condensation products, on the other hand, show only a slight leveling effect.
It has now been found that the compounds prepared according to the invention do not have these disadvantages.
The same can be used in the pH range from about 3-7, that is to say in the absence or in the presence of, for example, sulfuric acid, phosphoric acid, formic acid, acetic acid or buffer mixtures. Furthermore, neutral salts, e.g. B.
Sodium sulfate or sodium chloride, may be present.
The amount of leveling and stripping agent to be used must depend on the dyeing conditions present in each case, e.g. B. on the type and amount of dye and on the character and processing condition of the fiber material. It is, for example, 0.2-3% of the weight of the goods. The auxiliaries can be added to the dye bath before or during the dyeing process.
They can be added to the dyebath alone or used in combination with other leveling and stripping agents, such as, for example, alkyl or fatty amine polyglycol ethers.
The textile material to be treated by dyeing can be in any form, that is, for. B. as a fabric, as yarn or loose. According to its composition, it can consist of a single type of fiber or of mixtures of these.
The auxiliaries produced according to the invention are particularly suitable for dyeing with sulfonic acid and carboxyl group-free metal complex dyes which contain less than 2 metal atoms complexed to 2 molecules of monoazo dye, especially those which contain essentially 1 metal atom complexed to 2 molecules of monoazo compound.
In the following examples, T.
Parts by weight.
example 1
At 310 T. of a technical amine mixture containing about 850/0 primary amines, which consist of about 300 / o cetylamine, about 25 / o octadecylamine and about 450/0 octadecylamine, 130 to 1700 in the presence of 1.5 T . In the amine mixture finely divided sodium hydroxide 880 T. ethylene oxide attached.
To 129 parts of the resulting polyglycol ether mixture, 13.2 parts of dimethyl sulfate are added dropwise over the course of 15 minutes at 40 to 600. After the addition, the temperature is kept at 70-80 "for 60 minutes. It is then cooled and a solution of 23.4 parts of chlorosulfonic acid and 200 parts is added dropwise at 45-50 in the course of 10 minutes.
Chloroform too. The chloroform is then evaporated off in vacuo and the residue is neutralized with 3N sodium hydroxide solution.
Example 2
128 T. of the adduct of 880 T.
Ethylene oxide to 400 T. of the commercially available diamine of the general formula R-NH (CH2) 3NH2, in which R is a higher alkyl group derived from tallow, which is present in a degree of purity of about 804 / o, calculated as diamine, and a Has a melting range of about 44 180, are reacted according to the information in Example 1 with 25.2 parts of chlorosulfonic acid. The sulfation product is then made phenolphthaline-alkaline with soda solution. Then 13.0 T. dimethyl sulfate are added dropwise with stirring at 60-700. The quaternary ammonium group-containing sulfuric acid ester mixture obtained is suitable as a leveling and stripping agent.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH355457T | 1957-02-06 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH355457A true CH355457A (en) | 1961-07-15 |
Family
ID=4510842
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH355457D CH355457A (en) | 1957-02-06 | 1957-02-06 | Process for the preparation of compounds which can be used as leveling and stripping agents |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH355457A (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3355243A (en) * | 1963-06-11 | 1967-11-28 | Geigy Ag J R | Process for the dyeing of polyacrylonitrile fibers |
| US3919283A (en) * | 1965-03-18 | 1975-11-11 | Ciba Geigy Ag | Sulfate derivatives of polyglycol compounds |
| US3958931A (en) * | 1965-03-18 | 1976-05-25 | Ciba-Geigy Ag | Wool dyeing with epihalohydrin or chloroacetamide quarternized polyglycolamine assisted dye solution |
| US4132657A (en) * | 1973-04-09 | 1979-01-02 | Gaf Corporation | Treatment of metal surfaces |
| US4138371A (en) | 1976-04-07 | 1979-02-06 | Gaf Corporation | Washing method using amphoteric surface active agents |
-
1957
- 1957-02-06 CH CH355457D patent/CH355457A/en unknown
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3355243A (en) * | 1963-06-11 | 1967-11-28 | Geigy Ag J R | Process for the dyeing of polyacrylonitrile fibers |
| US3919283A (en) * | 1965-03-18 | 1975-11-11 | Ciba Geigy Ag | Sulfate derivatives of polyglycol compounds |
| US3958931A (en) * | 1965-03-18 | 1976-05-25 | Ciba-Geigy Ag | Wool dyeing with epihalohydrin or chloroacetamide quarternized polyglycolamine assisted dye solution |
| US4132657A (en) * | 1973-04-09 | 1979-01-02 | Gaf Corporation | Treatment of metal surfaces |
| US4138371A (en) | 1976-04-07 | 1979-02-06 | Gaf Corporation | Washing method using amphoteric surface active agents |
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