DE4417947A1 - Nonionic surfactant for substit. for alkylphenol alkoxylate surfactant - Google Patents
Nonionic surfactant for substit. for alkylphenol alkoxylate surfactantInfo
- Publication number
- DE4417947A1 DE4417947A1 DE4417947A DE4417947A DE4417947A1 DE 4417947 A1 DE4417947 A1 DE 4417947A1 DE 4417947 A DE4417947 A DE 4417947A DE 4417947 A DE4417947 A DE 4417947A DE 4417947 A1 DE4417947 A1 DE 4417947A1
- Authority
- DE
- Germany
- Prior art keywords
- surfactant
- surfactants
- substit
- alkylphenol
- alkylphenol alkoxylate
- 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.)
- Withdrawn
Links
- 239000004094 surface-active agent Substances 0.000 title claims abstract description 12
- 239000002736 nonionic surfactant Substances 0.000 title description 2
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 238000005984 hydrogenation reaction Methods 0.000 claims 1
- -1 Alkyl cyclohexanol Chemical compound 0.000 abstract 1
- 239000002904 solvent Substances 0.000 description 5
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 3
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- AFABGHUZZDYHJO-UHFFFAOYSA-N 2-Methylpentane Chemical compound CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 2
- 239000003925 fat Substances 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- YJIHHZAGMZFGKS-UHFFFAOYSA-N 4-nonylcyclohexan-1-ol Chemical compound CCCCCCCCCC1CCC(O)CC1 YJIHHZAGMZFGKS-UHFFFAOYSA-N 0.000 description 1
- IGFHQQFPSIBGKE-UHFFFAOYSA-N 4-nonylphenol Chemical compound CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 125000005233 alkylalcohol group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- YRUMDWGUXBZEPE-UHFFFAOYSA-N cyclohexane Chemical compound C1CCCCC1.C1CCCCC1 YRUMDWGUXBZEPE-UHFFFAOYSA-N 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
Classifications
-
- 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
- C09K23/42—Ethers, e.g. polyglycol ethers of alcohols or phenols
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/18—Ethers having an ether-oxygen atom bound to a carbon atom of a ring other than a six-membered aromatic ring
- C07C43/196—Ethers having an ether-oxygen atom bound to a carbon atom of a ring other than a six-membered aromatic ring containing hydroxy or O-metal groups
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/66—Non-ionic compounds
- C11D1/72—Ethers of polyoxyalkylene glycols
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
Abstract
Description
Alkylphenolalkoxilate bzw. vorwiegend Alkylphenolethoxilate (APEO) besitzen ausgezeichnete Schmutzlöse-, Wasch- und Dis pergiereigenschaften. In ihrer Leistung sind sie unter den nichtionischen Tensiden führend.Alkylphenol alkoxylates or predominantly alkylphenol ethoxylates (APEO) have excellent dirt dissolving, washing and dis performance properties. They are among the best in their performance leading non-ionic surfactants.
Seit einigen Jahren ist diese Tensidgruppe aus Umweltgründen in die Kritik geraten, so daß man sie durch unbedenklichere Tenside ersetzen muß.This surfactant group has been used for environmental reasons for several years come under criticism, so that it can be Must replace surfactants.
Der praktizierte Ersatz der APEO durch geradkettige und ver zweigte Alkylalkoholalkoxilate ist häufig aber nicht voll befriedigend.The practiced replacement of the APEO by straight-chain and ver branched alkyl alcohol alkoxylates are often not full satisfying.
Es werden Tenside beansprucht, die auf Grund struktureller Ähnlichkeit mit APEO vorzüglich geeignet sind, APEO zu ersetzen.Surfactants are claimed due to their structural nature Similarity to APEO are excellently suited to APEO too replace.
Es ist bekannt, daß Aromaten bessere Lösemittel als Hydroaro maten aber diese wiederum bessere Lösemittel als geradkettige oder verzweigte Aliphaten sind. So werden Fette, Harze und Wachse im allgemeinen von Benzol besser als von Cyclohexan aber von Cyclohexan wiederum besser als von n-Hexan oder iso-Hexan gelöst. Cyclohexanol z. B. ist ein besseres Lösemittel für Fette, Harze und Wachse als n-Hexanol.It is known that aromatics have better solvents than Hydroaro however, these in turn have better solvents than straight-chain ones or are branched aliphatics. This is how fats, resins and In general, benzene grows better than cyclohexane Cyclohexane in turn is better than n-hexane or iso-hexane solved. Cyclohexanol e.g. B. is a better solvent for Fats, resins and waxes as n-hexanol.
Diese für Lösemittel an sich bekannte "Lösekraftreihe" Aromaten - Hydroaromaten - n/i-Aliphaten wurde erfindungsgemäß auf den hydrophoben Molekülteil von Tensiden übertragen. Es ist erfindungsgemäß günstiger einen aromatischen Molekülteil durch einen hydroaromatischen Molekülteil statt - wie beim bisherigen APEO-Ersatz praktiziert - durch einen rein linearen oder verzweigten aliphatischen Molekülteil zu ersetzen.This "solvent force series" known per se for solvents Aromatics - hydroaromatics - n / i aliphatics were invented transferred to the hydrophobic molecular part of surfactants. According to the invention, it is cheaper to use an aromatic part of the molecule by a hydroaromatic part of the molecule instead - as with the previous APEO replacement practiced - by a purely linear or to replace branched aliphatic part of the molecule.
p-i-Nonylphenol wird bei 190°C und 2,5 MPa Wasserstoffdruck am Nickelkontakt in flüssiger Phase zu p-i-Nonylcyclohexanol hy driert. Nach Abtrennung des Nickelkatalysators wird das gebil dete p-i-Nononylcyclohexanol bei 120°C und 0,3 MPa Ethylenoxid druck in Gegenwart von 1% NaOH zu p-i-Nonylcyclohexanolethoxi lat mit 9 Mol Ethylenoxid pro Mol Alkylcyclohexanol ethoxiliert.p-i-Nonylphenol is at 190 ° C and 2.5 MPa hydrogen pressure Nickel contact in the liquid phase to p-i-nonylcyclohexanol hy third. After separation of the nickel catalyst, this is done Detete p-i-nononylcyclohexanol at 120 ° C and 0.3 MPa ethylene oxide pressure in the presence of 1% NaOH to p-i-nonylcyclohexanolethoxi lat with 9 moles of ethylene oxide per mole of alkylcyclohexanol ethoxylated.
Das gebildete Produkt ist ein ausgezeichneter Ersatzstoff für p-i-Nononylphenolethoxilat mit 9 Mol Ethylenoxid.The product formed is an excellent substitute for p-i-nononylphenol ethoxylate with 9 moles of ethylene oxide.
Claims (4)
R² = H oder CH₃ oder beides
n = 2-60.4. Surfactants according to claim 1, characterized in that they have the following structure: R¹ = linear or branched C 6-14 alkyl
R² = H or CH₃ or both
n = 2-60.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE4417947A DE4417947A1 (en) | 1994-05-21 | 1994-05-21 | Nonionic surfactant for substit. for alkylphenol alkoxylate surfactant |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE4417947A DE4417947A1 (en) | 1994-05-21 | 1994-05-21 | Nonionic surfactant for substit. for alkylphenol alkoxylate surfactant |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE4417947A1 true DE4417947A1 (en) | 1995-11-23 |
Family
ID=6518742
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE4417947A Withdrawn DE4417947A1 (en) | 1994-05-21 | 1994-05-21 | Nonionic surfactant for substit. for alkylphenol alkoxylate surfactant |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE4417947A1 (en) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1999011594A1 (en) * | 1997-09-03 | 1999-03-11 | Rayburn Randy L | Alkyl cyclohexanol alkoxylates and method for making same |
| EP0945421A1 (en) * | 1998-03-23 | 1999-09-29 | Mitsui Chemicals, Inc. | Alkylcyclohexanol-alkylene oxide adduct and preparation process thereof |
| US9969817B2 (en) | 2015-12-15 | 2018-05-15 | Rohm And Haas Company | Phenyl glycidyl ether adduct of maltodextrin |
| US10604590B2 (en) | 2015-12-17 | 2020-03-31 | Dow Global Technologies Llc | Di- or tristyrylphenol monogycidyl ether adduct of maltodextrin |
| US10654964B2 (en) | 2016-07-05 | 2020-05-19 | Dow Global Technologies Llc | Compositions comprising polyether-urethane-urea additives for block resistance and open time |
| US10669444B2 (en) | 2016-03-11 | 2020-06-02 | Dow Global Technologies Llc | Coating formulation with an open time additive |
| WO2020199555A1 (en) * | 2019-04-04 | 2020-10-08 | 江南大学 | Preparation and application of alkyl cyclohexanol polyoxyethylene ether emulsifying agent |
-
1994
- 1994-05-21 DE DE4417947A patent/DE4417947A1/en not_active Withdrawn
Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1999011594A1 (en) * | 1997-09-03 | 1999-03-11 | Rayburn Randy L | Alkyl cyclohexanol alkoxylates and method for making same |
| US6111146A (en) * | 1997-09-03 | 2000-08-29 | Rayborn; Randy L. | Alkyl cyclohexanol alkoxylates and method for making same |
| EP0945421A1 (en) * | 1998-03-23 | 1999-09-29 | Mitsui Chemicals, Inc. | Alkylcyclohexanol-alkylene oxide adduct and preparation process thereof |
| KR100316557B1 (en) * | 1998-03-23 | 2001-12-12 | 사토 아키오 | Preparation process of alkylcyclohexanol alkyleneoxide adduct |
| US6437194B2 (en) * | 1998-03-23 | 2002-08-20 | Mitsui Chemicals, Inc. | Process for preparing an alkylcyclohexanol alkylene oxide adduct |
| CN1102928C (en) * | 1998-03-23 | 2003-03-12 | 三井化学株式会社 | Alkylcyclohexanolalkyleneoxide adduct and preparation process thereof |
| US9969817B2 (en) | 2015-12-15 | 2018-05-15 | Rohm And Haas Company | Phenyl glycidyl ether adduct of maltodextrin |
| US10604590B2 (en) | 2015-12-17 | 2020-03-31 | Dow Global Technologies Llc | Di- or tristyrylphenol monogycidyl ether adduct of maltodextrin |
| US10669444B2 (en) | 2016-03-11 | 2020-06-02 | Dow Global Technologies Llc | Coating formulation with an open time additive |
| US10654964B2 (en) | 2016-07-05 | 2020-05-19 | Dow Global Technologies Llc | Compositions comprising polyether-urethane-urea additives for block resistance and open time |
| WO2020199555A1 (en) * | 2019-04-04 | 2020-10-08 | 江南大学 | Preparation and application of alkyl cyclohexanol polyoxyethylene ether emulsifying agent |
| US12116455B2 (en) | 2019-04-04 | 2024-10-15 | Jiangnan University | Preparation of alkylcyclohexanol polyoxyethylene ether emulsifier and application thereof |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8122 | Nonbinding interest in granting licences declared | ||
| 8139 | Disposal/non-payment of the annual fee |