DE696317C - eestern - Google Patents
eesternInfo
- Publication number
- DE696317C DE696317C DE1930I0058669 DEI0058669D DE696317C DE 696317 C DE696317 C DE 696317C DE 1930I0058669 DE1930I0058669 DE 1930I0058669 DE I0058669 D DEI0058669 D DE I0058669D DE 696317 C DE696317 C DE 696317C
- Authority
- DE
- Germany
- Prior art keywords
- phosphoric acid
- aliphatic
- acid esters
- acidic phosphoric
- ethers
- 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.)
- Expired
Links
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 10
- 230000002378 acidificating effect Effects 0.000 claims description 8
- 150000003014 phosphoric acid esters Chemical class 0.000 claims description 8
- 150000002170 ethers Chemical class 0.000 claims description 7
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 5
- 125000001931 aliphatic group Chemical group 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- 238000006467 substitution reaction Methods 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 238000000034 method Methods 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- -1 nitro, amino, carboxyl Chemical group 0.000 description 3
- WTBAHSZERDXKKZ-UHFFFAOYSA-N octadecanoyl chloride Chemical compound CCCCCCCCCCCCCCCCCC(Cl)=O WTBAHSZERDXKKZ-UHFFFAOYSA-N 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- FKMHSNTVILORFA-UHFFFAOYSA-N 2-[2-(2-dodecoxyethoxy)ethoxy]ethanol Chemical class CCCCCCCCCCCCOCCOCCOCCO FKMHSNTVILORFA-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 2
- NMRPBPVERJPACX-UHFFFAOYSA-N octan-3-ol Chemical compound CCCCCC(O)CC NMRPBPVERJPACX-UHFFFAOYSA-N 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 229920000151 polyglycol Polymers 0.000 description 2
- 239000010695 polyglycol Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 2
- PRBXPAHXMGDVNQ-UHFFFAOYSA-N 2-[2-(2-hydroxyethoxy)ethoxy]acetic acid Chemical compound OCCOCCOCC(O)=O PRBXPAHXMGDVNQ-UHFFFAOYSA-N 0.000 description 1
- DNNVYYADPRBILB-UHFFFAOYSA-N 2-[2-(2-hydroxyethoxy)ethoxy]ethanol;propane-1,2,3-triol Chemical compound OCC(O)CO.OCCOCCOCCO DNNVYYADPRBILB-UHFFFAOYSA-N 0.000 description 1
- XXZCIYUJYUESMD-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]-3-(morpholin-4-ylmethyl)pyrazol-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C=1C(=NN(C=1)CC(=O)N1CC2=C(CC1)NN=N2)CN1CCOCC1 XXZCIYUJYUESMD-UHFFFAOYSA-N 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical class O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000004061 bleaching Methods 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 229960000541 cetyl alcohol Drugs 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 150000002402 hexoses Chemical class 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- VJQGGZWPOMJLTP-UHFFFAOYSA-N octadecane-1,1-diol Chemical compound CCCCCCCCCCCCCCCCCC(O)O VJQGGZWPOMJLTP-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 239000000123 paper Substances 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- NVBFHJWHLNUMCV-UHFFFAOYSA-N sulfamide Chemical group NS(N)(=O)=O NVBFHJWHLNUMCV-UHFFFAOYSA-N 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
Classifications
-
- 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
- C07F9/091—Esters of phosphoric acids with hydroxyalkyl compounds with further substituents on alkyl
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)
- Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
- Detergent Compositions (AREA)
Description
Verfahren zur Herstellung von sauren Phosphorsäureestern Es wurde gefunden, daB man technisch sehr wertvolle saure Phosphorsäureester erhalten kann, wenn man Polyoxyalkyläther aliphatischer, cycloaliphatischer oder aliphatischaromatischer Alkohole oder ihre Substitutionsprodukte durch Behandeln-mit Phosphorsäure öder anderen, ähnlich - wirkenden Mitteln in an sich bekannter Weise in saure Phosphorsäureester bzw. ihre, Salze überführt.Process for the preparation of acidic phosphoric acid esters It has been found that one can obtain industrially very valuable acidic phosphoric acid esters, if polyoxyalkyl ethers are aliphatic, cycloaliphatic or aliphatic-aromatic Alcohols or their substitution products by treatment with phosphoric acid or other, similar - acting agents in a known manner into acidic phosphoric acid esters or their, salts transferred.
Die genannten Polyoxyalkyläther können auf beliebige Weise hergestellt sein. Besonders geeignet für ihre Herstellung ist die Umsetzung von = Mol eines aliphatischen, cycloaliphatischen oder aliphatisch-aromatischen Alkohols mit mehr als i Mol eines Alkylenoxyds. Auch die Derivate oder Substitutionsprodukte von Polyoxyalkyläthern, die beispielsweise Nitro-, Amino-, Carboxyl-, veresterte Carboxyl- oder Sulfamidgruppen oder-Halogenatome enthalten, können Verwendung finden.The polyoxyalkyl ethers mentioned can be prepared in any desired manner be. The conversion of = mole of one is particularly suitable for their preparation aliphatic, cycloaliphatic or aliphatic-aromatic alcohol with more as one mole of an alkylene oxide. The derivatives or substitution products of polyoxyalkyl ethers, the, for example, nitro, amino, carboxyl, esterified carboxyl or sulfamide groups or halogen atoms can be used.
Die Einführung der Phosphorsäureestergruppen wird zum Beispiel durch Behandeln der genannten Oxyäther mit konzentrierter Phosphorsäure oder Phosphorpentoxyd oder mit Phosphoroxychlorid und _ nachfolgende Verseifung der erhaltenen Chlorverbindungen durchgeführt. Die Umsetzung der genannten Polyoxyalkyläther mit Phosphorsäure kann auch unter Verwendung von organischen Lösungs-oder Verdünnungsmitteln, wie Trichloräthylen, Tetrachlorkohlenstoff, Chloroform oder Nitrobenzol, erfolgen.The introduction of the phosphoric ester groups is carried out, for example, by Treat the mentioned oxyethers with concentrated phosphoric acid or phosphorus pentoxide or with phosphorus oxychloride and subsequent saponification of the chlorine compounds obtained carried out. The reaction of the polyoxyalkyl ethers mentioned with phosphoric acid can also using organic solvents or diluents, such as trichlorethylene, Carbon tetrachloride, chloroform or nitrobenzene.
Die auf die beschriebene Weise hergestellten Produkte besitzen ein vorzügliches Netz-, Reinigungs-, Dispergier- und Waschvermögen; sie eignen sich daher als Zusätze zu Bädern für die verschiedensten Zwecke der Textilindustrie, z. B. zum Färben, Bleichen, Appretieren und Waschen, ferner als Dispergiermittel, z. B> zur Herstellung von Emulsionen für die Lack-, Leder- oder Papierindustrie.The products manufactured in the manner described have a excellent wetting, cleaning, dispersing and washing power; they are suitable therefore as additives to baths for various purposes in the textile industry, z. B. for dyeing, bleaching, finishing and washing, also as a dispersant, z. B> for the production of emulsions for the paint, leather or paper industry.
Die erhaltenen, sauren Phosphorsäureester können als solche oder in Form ihrer Salze Verwendung finden.The acidic phosphoric acid esters obtained can be used as such or in Find the form of their salts use.
Beispieli 318 Gewichtsteile des aus i Mol Laurylalkohol und 3 Mol Äthylenoxyd erhältlichen Triäthylenglykolmonolauryläthers werden mit konzentrierter Phosphorsäure behandelt. Durch Neutralisation mit Natronlauge unter Kühlung erhält man das Natriumsalz des sauren Phosphorsäureestersdes Triäthylenglykohnonolauryl äthers. . Zu ähnlichen Produkten gelangt man, wenn man an Stelle des Triäthylenglykoläthers des L aurylalkohols einen Polyglykoläther aus Cetylalkohol, Oktadecylalkohol, Oktadecandiol,Äthylhexylalkohol oder Benzylalkohol anwendet,' wobei es unwesentlich ist, auf welche Weise die Äther erhalten worden sind. Beispie12 i Mol Triäthylenglykolmonoglycerinäther wird mit i Mol Stearinsäurechlorid umgesetzt und der erhaltene Stearinsäureester in der oben angegebenen Weise in den sauren Phosphorsäureester übergeführt. Das erhaltene Produkt kann als solches oder in Form seiner Alkalisalze Verwendung finden; es besitzt ein besonders gutes Netz-, Wasch- und Emulgiervermögen. An Stelle von Stearinsäurechlorid kann man auch sulfoniertes Stearinsäurechlorid anwenden, und man erhält so ein Produkt von ähnlichen Eigenschaften. Den Triätl@ylenglykolmonoglycerinäther kann man auch durch andere Polyglykoläther ersetzen, wobei zur Ätherbildung auch mehrwertige Alkohole, wie Hexosen, Disaccha#ide oder Alkohole, die durch Reduktion von Aldolen erhältlich sind, Verwendung finden können.Examplei 318 parts by weight of the from 1 mole of lauryl alcohol and 3 moles Ethylene oxide available triethylene glycol monolauryl ethers are concentrated with Treated phosphoric acid. Obtained by neutralization with sodium hydroxide solution with cooling the sodium salt of the acidic phosphoric acid ester of triethylene glycol monolauryl ether. . You get to similar products if you take the place the triethylene glycol ether of l auryl alcohol, a polyglycol ether made from cetyl alcohol, Uses octadecyl alcohol, octadecanediol, ethylhexyl alcohol or benzyl alcohol, ' it is immaterial how the ethers were obtained. Example12 1 mole of triethylene glycol monoglycerol ether is reacted with 1 mole of stearic acid chloride and the resulting stearic acid ester in the above-mentioned manner in the acidic Phosphoric acid ester converted. The product obtained can be as such or in the form its alkali salts are used; it has a particularly good mesh, washing and emulsifying power. Instead of stearic acid chloride, one can also use sulfonated Apply stearic acid chloride and a product with similar properties is obtained. The Triätl @ ylenglykolmonoglycerinäther can also be replaced by other polyglycol ethers replace, whereby also polyvalent alcohols, such as hexoses, disaccha ide, for the formation of ether or alcohols obtainable by reducing aldols are used can.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1930I0058669 DE696317C (en) | 1930-08-12 | 1930-08-12 | eestern |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1930I0058669 DE696317C (en) | 1930-08-12 | 1930-08-12 | eestern |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE696317C true DE696317C (en) | 1940-09-18 |
Family
ID=7194832
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1930I0058669 Expired DE696317C (en) | 1930-08-12 | 1930-08-12 | eestern |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE696317C (en) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE903574C (en) * | 1942-02-01 | 1954-02-08 | Albert Ag Chem Werke | Process for the preparation of Pentaerythritdiiodohydrinphosphoric acid |
| DE942466C (en) * | 1951-07-06 | 1956-05-03 | Hoechst Ag | Methods for cleaning clothes and other textiles |
| DE954009C (en) * | 1953-12-30 | 1956-12-13 | Huels Chemische Werke Ag | Use of phosphoric acid esters as emulsifiers for the emulsion polymerization of polymerizable chlorine-containing organic compounds |
| DE956048C (en) * | 1953-06-26 | 1957-01-10 | Boehme Fettchemie G M B H | Process for the production of electrolyte-resistant dispersions |
| DE977317C (en) * | 1954-08-14 | 1965-12-02 | Boehme Fettchemie G M B H | Process for removing chrome soaps from the wool of chrome-tanned fur skins |
| DE1234234B (en) * | 1953-09-29 | 1967-02-16 | Philips Nv | Use of acidic organic phosphorus compounds as dispersants for powdery substances |
-
1930
- 1930-08-12 DE DE1930I0058669 patent/DE696317C/en not_active Expired
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE903574C (en) * | 1942-02-01 | 1954-02-08 | Albert Ag Chem Werke | Process for the preparation of Pentaerythritdiiodohydrinphosphoric acid |
| DE942466C (en) * | 1951-07-06 | 1956-05-03 | Hoechst Ag | Methods for cleaning clothes and other textiles |
| DE956048C (en) * | 1953-06-26 | 1957-01-10 | Boehme Fettchemie G M B H | Process for the production of electrolyte-resistant dispersions |
| DE1234234B (en) * | 1953-09-29 | 1967-02-16 | Philips Nv | Use of acidic organic phosphorus compounds as dispersants for powdery substances |
| DE954009C (en) * | 1953-12-30 | 1956-12-13 | Huels Chemische Werke Ag | Use of phosphoric acid esters as emulsifiers for the emulsion polymerization of polymerizable chlorine-containing organic compounds |
| DE977317C (en) * | 1954-08-14 | 1965-12-02 | Boehme Fettchemie G M B H | Process for removing chrome soaps from the wool of chrome-tanned fur skins |
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