EP0399581A2 - Compositions tensio-actives - Google Patents
Compositions tensio-actives Download PDFInfo
- Publication number
- EP0399581A2 EP0399581A2 EP90201047A EP90201047A EP0399581A2 EP 0399581 A2 EP0399581 A2 EP 0399581A2 EP 90201047 A EP90201047 A EP 90201047A EP 90201047 A EP90201047 A EP 90201047A EP 0399581 A2 EP0399581 A2 EP 0399581A2
- Authority
- EP
- European Patent Office
- Prior art keywords
- weight
- per cent
- range
- alcohol
- composition
- 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- Withdrawn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
- 239000000203 mixture Substances 0.000 title claims abstract description 156
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 143
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 44
- GSPKZYJPUDYKPI-UHFFFAOYSA-N diethoxy sulfate Chemical compound CCOOS(=O)(=O)OOCC GSPKZYJPUDYKPI-UHFFFAOYSA-N 0.000 claims abstract description 41
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 32
- 239000000843 powder Substances 0.000 claims abstract description 31
- 239000003599 detergent Substances 0.000 claims abstract description 28
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 27
- 239000007788 liquid Substances 0.000 claims abstract description 21
- 125000006353 oxyethylene group Chemical group 0.000 claims abstract description 14
- 125000002877 alkyl aryl group Chemical group 0.000 claims abstract description 11
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims abstract description 5
- 229910001413 alkali metal ion Inorganic materials 0.000 claims abstract description 5
- 150000001768 cations Chemical class 0.000 claims abstract description 5
- 239000004615 ingredient Substances 0.000 claims abstract description 4
- 150000003839 salts Chemical class 0.000 claims abstract description 4
- 239000003463 adsorbent Substances 0.000 claims abstract description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 23
- 238000000034 method Methods 0.000 claims description 15
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 12
- 239000003960 organic solvent Substances 0.000 claims description 9
- -1 sulphuric acid ester Chemical class 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 6
- 239000002585 base Substances 0.000 claims description 5
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims description 3
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 claims description 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 2
- 239000000908 ammonium hydroxide Substances 0.000 claims description 2
- 239000005456 alcohol based solvent Substances 0.000 claims 1
- 239000001117 sulphuric acid Substances 0.000 claims 1
- 235000011149 sulphuric acid Nutrition 0.000 claims 1
- 239000004094 surface-active agent Substances 0.000 description 54
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 29
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 18
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 16
- 239000000047 product Substances 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 12
- 150000002191 fatty alcohols Chemical class 0.000 description 11
- 150000001298 alcohols Chemical class 0.000 description 10
- 238000007046 ethoxylation reaction Methods 0.000 description 8
- 238000009472 formulation Methods 0.000 description 8
- 238000005670 sulfation reaction Methods 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
- 239000002689 soil Substances 0.000 description 7
- 230000019635 sulfation Effects 0.000 description 7
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 239000000499 gel Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- JSPLKZUTYZBBKA-UHFFFAOYSA-N trioxidane Chemical class OOO JSPLKZUTYZBBKA-UHFFFAOYSA-N 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 5
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
- 239000006227 byproduct Substances 0.000 description 5
- 229910052799 carbon Inorganic materials 0.000 description 5
- 230000009969 flowable effect Effects 0.000 description 5
- 159000000000 sodium salts Chemical class 0.000 description 5
- 229910052938 sodium sulfate Inorganic materials 0.000 description 5
- 235000011152 sodium sulphate Nutrition 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 239000004435 Oxo alcohol Substances 0.000 description 4
- 150000001340 alkali metals Chemical class 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000011552 falling film Substances 0.000 description 4
- 239000011259 mixed solution Substances 0.000 description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 125000003158 alcohol group Chemical group 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 239000003945 anionic surfactant Substances 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 235000008504 concentrate Nutrition 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- 239000007859 condensation product Substances 0.000 description 3
- 239000012467 final product Substances 0.000 description 3
- 239000002736 nonionic surfactant Substances 0.000 description 3
- 150000003138 primary alcohols Chemical class 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 125000006539 C12 alkyl group Chemical group [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])* 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 235000013162 Cocos nucifera Nutrition 0.000 description 2
- 244000060011 Cocos nucifera Species 0.000 description 2
- 239000011149 active material Substances 0.000 description 2
- 230000032683 aging Effects 0.000 description 2
- 230000001476 alcoholic effect Effects 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 2
- 239000004927 clay Substances 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 125000002704 decyl group Chemical group [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])* 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 238000003760 magnetic stirring Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000002480 mineral oil Substances 0.000 description 2
- 235000010446 mineral oil Nutrition 0.000 description 2
- 230000003472 neutralizing effect Effects 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 210000002374 sebum Anatomy 0.000 description 2
- 150000003333 secondary alcohols Chemical class 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 230000001180 sulfating effect Effects 0.000 description 2
- 239000003760 tallow Substances 0.000 description 2
- HLZKNKRTKFSKGZ-UHFFFAOYSA-N tetradecan-1-ol Chemical compound CCCCCCCCCCCCCCO HLZKNKRTKFSKGZ-UHFFFAOYSA-N 0.000 description 2
- 239000012808 vapor phase Substances 0.000 description 2
- 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 1
- 229920000742 Cotton Polymers 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 229910000272 alkali metal oxide Inorganic materials 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 238000004880 explosion Methods 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000003752 hydrotrope Substances 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 235000014666 liquid concentrate Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 235000019832 sodium triphosphate Nutrition 0.000 description 1
- 239000013042 solid detergent Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical compound NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 1
- 238000012956 testing procedure Methods 0.000 description 1
Classifications
-
- 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
- C11D1/83—Mixtures of non-ionic with anionic compounds
-
- 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
-
- 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
- C11D1/02—Anionic compounds
- C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
- C11D1/29—Sulfates of polyoxyalkylene ethers
-
- 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
Definitions
- This invention relates to liquid and solid surface active compositions of high active matter content comprising a mixture of an alcohol ethoxylate and an alcohol ethoxysulfate.
- Liquid surfactant compositions are well known in the field of laundry detergents and, whether for domestic or industrial applications, practically all of the available formulations are solutions of one or more surface active materials (surfactants) in water, together with an organic solvent if necessary. Such formulations usually contain only about 10 wt% to 45 wt% active matter.
- alcohol ethoxysulfates are finding increasing use in household laundry powders and liquids as part of mixed active surfactant systems.
- a drawback to the use of alcohol ethoxysulfates in formulations is their strong gel forming tendencies as they are diluted into formulations having concentrations greater than 30%. Gel formation can be reduced by incorporating approximately 14% ethanol into 60% active matter solutions of alcohol ethoxysulfates. This relatively high active matter solution lowers shipping costs, but the presence of ethanol in alcohol ethoxysulfate solutions prevents their use in spray-dried or dry-blended laundry powders where the flammability and combustibility of ethanol are a significant processing hazard. In addition, excessive water prohibits the formation of a free-flowing powder when surfactant concentrates are blended with water-soluble detergent powder particles.
- It is therefore an object of this invention to prepare surface active compositions comprising a blend of alcohol ethoxylates and alcohol ethoxysulfates with less than 15% water and substantially free of any organic solvent.
- an anionic surfactant, alcohol ethoxysulfate is blended with a nonionic surfactant, alcohol ethoxylate, where each of these surfactant types act as mutual hydrotropes, thereby permitting liquid concentrates containing active matter levels of at least 85%.
- This invention relates to a surface active composition which is either or liquid or a dry powder, which comprises: a) from 15 per cent by weight to 99 per cent by weight of an alcohol ethoxylate having the formula R-O(CH2CH2O) n -H, wherein R is an alkyl group having from 8 to 18 carbon atoms or an alkylaryl group having an alkyl moiety in the range of from 8 to 12 carbon atoms, and n represents the average number of oxyethylene groups per molecule and is a number in the range of from 1 to 12, b) from 1 per cent by weight to 80 per cent by weight of a salt of an alcohol ethoxysulfate having the formula R′ -O-(CH2CH2O) x -SO3M, wherein R′ is an alkyl group having from 8 to 18 carbon atoms or an alkylaryl group having an aikyl moiety in the range of from 8 to 11 carbon atoms, M is a cation selected from an
- This invention also relates to powder detergent compositions prepared utilizing these surfactant compositions and processes for preparing them.
- composition is also substantially free of organic solvents, particularly low molecular weight organic solvents and more particularly, lower alcohols having from 1 to 5 carbon atoms, particularly ethanol and methanol.
- organic solvents particularly low molecular weight organic solvents and more particularly, lower alcohols having from 1 to 5 carbon atoms, particularly ethanol and methanol.
- liquid shall mean a pourable material which is neither a solid nor a gel.
- substantially free of an organic solvent shall mean that the amount of organic solvent present, if any, is less than the amount which would substantially alter the properties of the composition.
- the composition typically contains less than 3 per cent by weight of organic solvent, per total weight of the composition.
- R-O- (CH2-CH2O) n -H (I) wherein R is a straight-chain or branched-chain alkyl group having in the range of from 8 to 18 carbon atoms, preferably from 12 to 18 carbon atoms, or an alkylaryl group having an alkyl moiety having from 8 to 12 carbon atoms, and n represents the average number of oxyethylene groups per molecule and is in the range of from 1 to 12, preferably from 2 to 9 and more preferably from 2 to 5.
- the alkyl group can have a carbon chain which is straight or branched, and the ethoxylate component can be a combination of straight-chain and branched molecules.
- the ethoxylate component can be a combination of straight-chain and branched molecules.
- about 85 per cent of the R groups in the instant composition are straight-chain.
- R can be substituted with any substituent which is inert such as, for example, halo groups.
- Ethoxylates within this class are conventionally prepared by the sequential addition of ethylene oxide to the corresponding alcohol (ROH) in the presence of a catalyst.
- the alcohol ethoxylate component of this invention is preferably derived by ethoxylation of primary or secondary, straight-chain or branched alcohols.
- the most common ethoxylates in this class and the ones which are particularly useful in this invention are the primary alcohol ethoxylates, i.e., compounds of formula I in which R is an alkyl group and the -O-(CH2-CH2O) n -H ether substituent is bound to a primary carbon of the alkyl group.
- Alcohols which are suitable for ethoxylation to form the alcohol ethoxylate component of this invention include coconut fatty alcohols, tallow fatty alcohols, and the commercially available synthetic long-chain fatty alcohol blends, e.g., the C12 to C15 alcohol blends available as NEODOL 25 Alcohol (a registered trademark of product manufactured and sold by Shell Chemical Company), the C12 to C14 alcohol blends available as Tergitol 24L (a registered trademark of product manufactured and sold by Union Carbide Corporation), and the C12 to C13 alcohol blends available, for example, as NEODOL 23 Alcohol (Shell).
- NEODOL 25 Alcohol a registered trademark of product manufactured and sold by Shell Chemical Company
- Tergitol 24L a registered trademark of product manufactured and sold by Union Carbide Corporation
- C12 to C13 alcohol blends available, for example, as NEODOL 23 Alcohol (Shell).
- Suitable alcohol ethoxylates can be prepared by adding to the alcohol or mixture of alcohols to be ethoxylated a calculated amount, e.g., from 0.1 per cent by weight to 0.6 per cent by weight, preferably from 0.1 per cent by weight to 0.4 per cent by weight, based on total alcohol, of a strong base, typically an alkali metal or alkaline earth metal hydroxide such as sodium hydroxide or potassium hydroxide, which serves as a catalyst for ethoxylation.
- a strong base typically an alkali metal or alkaline earth metal hydroxide such as sodium hydroxide or potassium hydroxide, which serves as a catalyst for ethoxylation.
- the resulting mixture is dried, as by vapor phase removal of any water present, and an amount of ethylene oxide calculated to provide from 1 mole to 12 moles of ethylene oxide per mole of alcohol is then introduced and the resulting mixture is allowed to react until the ethylene oxide is consumed, the course of the reaction being followed by the decrease in reaction pressure.
- the ethoxylation is typically conducted at elevated temperatures and pressures. Suitable reaction temperatures range from 120 °C to 220 °C with the range of from 140 °C to 160 °C being preferred.
- a suitable reaction pressure is achieved by introducing to the reaction vessel the required amount of ethylene oxide which has a high vapor pressure at the desired reaction temperature.
- the partial pressure of the ethylene oxide reactant is preferably limited, for instance, to less than 4 bar, and/or the reactant is preferably diluted with an inert gas such as nitrogen, for instance, to a vapor phase concentration of 50 per cent or less.
- the reaction can, however, be safely accomplished at greater ethylene oxide concentration, greater total pressure and greater partial pressure of ethylene oxide if suitable precautions, known to the art, are taken to manage the risks of explosion.
- the pressure serves as a measure of the degree of the reaction and the reaction is considered to be substantially complete when the pressure no longer decreases with time.
- the ethoxylation procedure serves to introduce a desired average number of ethylene oxide units per mole of alcohol ethoxylate.
- treatment of an alcohol mixture with 3 moles of ethylene oxide per mole of alcohol serves to effect the ethoxylation of each alcohol molecule with an average of 3 ethylene oxide moieties per mole alcohol moiety, although a substantial proportion of alcohol moieties will become combined with more than 3 ethylene oxide moieties and an approximately equal proportion will have become combined with less than 3.
- a typical ethoxylation product mixture there is also a minor proportion of unreacted alcohol.
- a preferred class of nonionic ethoxylates is represented by the condensation product of a fatty alcohol having from 12 to 15 carbon atoms and from 2 to 9 moles of ethylene oxide per mole of fatty alcohol.
- Suitable species of this class of ethoxylates include: the condensation product of C12-C15 oxo-alcohols and 7 moles of ethylene oxide; the condensation product of narrow cut C14-C15 oxo-alcohols and 7 or 9 moles of ethylene oxide per mole of fatty (oxo)alcohol; the condensation of a narrow cut C12-C13 fatty (oxo)alcohol and 6.5 moles of ethylene oxide per mole of fatty alcohol.
- the fatty oxo-alcohols while primarily linear, can have, depending upon the processing conditions and raw material olefins, a certain degree of branching.
- a degree of branching in the range from 15% to 50% by weight is frequently found in commercially available oxo-alcohols.
- the amount of alcohol ethoxylate present in the composition of the present invention may range from 15 per cent by weight to 99 per cent by weight, preferably from 25 per cent by weight to 75 per cent by weight, and more preferably from 28 per cent by weight to 66 per cent by weight.
- the general class of anionic surfactants or alcohol ethoxysulfates of relevance to component (b) of the composition is characterized by the chemical formula R′-O- (CH2-CH2O) x -SO3M (II) wherein R′ is a straight-chain or branched-chain alkyl group having in the range of from 8 to 18 carbon atoms, preferably from 2 to 18 carbon atoms, or an alkylaryl group having an alkyl moiety having from 8 to 12 carbon atoms, x represents the average number of oxyethylene groups per molecule and is in the range of from 1 to 12, preferably from 5 to 12 and more preferably from 9 to 12 and M is a cation selected from an alkali metal ion, an ammonium ion, and mixtures thereof.
- R′ is preferably substantially straight-chain alkyl, that is, at least 50 per cent, preferably about 85 per cent, of the alkyl R′ groups in the instant composition are straight- chain. It is understood that R′ can be substituted with any substituent which is inert such as, for example, halo groups.
- the alcohol ethoxysulfates are derivatives of primary or secondary alcohols of carbon number ranging from 8 to 18.
- the alcohol precursors of the alcohol ethoxysulfate are straight-chain alcohols or are of a branched-chain structure.
- Alcohols which are suitable for ethoxylation to form an alcohol ethoxylate which can then be subjected to a sulfation procedure to form the alcohol ethoxysulfate component of the composition include coconut fatty alcohols, tallow fatty alcohols, and the commercially available long-chain synthetic fatty alcohol blends, e.g., the C12 to C15 alcohol blends available as NEODOL 25 Alcohol (Shell Chemical Company), the C12 to C14 alcohol blends available as Tergitol 24L (Union Carbide Corporation), and the C12 to C13 alcohol blends available, for example, as NEODOL 23 Alcohol (Shell).
- the alcohol ethoxysulfate component is typically prepared by first reacting the alcohol with 1 to 12 moles of ethylene oxide per mole of alcohol to form an alcohol ethoxylate product. Thereafter, these alcohol ethoxylate products are sulfated with a suitable sulfating reagent, and the resulting sulfated product mixture is neutralized with an aqueous alkali metal solution.
- Suitable sulfation procedures include sulfur trioxide (SO3) sulfation, chlorosulfonic acid (ClSO3H) sulfation and sulfamic acid (NH2SO3H) sulfation, with sulfur trioxide sulfation being preferred.
- a typical sulfur trioxide sulfation procedure includes contacting liquid alcohol ethoxylate and gaseous sulfur trioxide at about atmospheric pressure in the reaction zone of a falling film sulfator cooled by water at a temperature in the range of from 25 °C to 70 °C to yield the sulfuric acid ester of alcohol ethoxylate. The sulfuric acid ester of the alcohol ethoxylate then exits the falling film column and is neutralized with an alkali metal solution, e.g., sodium or potassium hydroxide, to form the alcohol ethoxysulfate salt.
- an alkali metal solution e.g., sodium or potassium hydroxide
- Specific sulfated ethoxylated detergent active compounds which can be used in the composition of the present invention include sulfated ethoxylated fatty alcohols, preferably linear primary or secondary alcohols with C8 to C18, preferably C12 to C15, alkyl groups and an average of 1 to 12, preferably 5 to 12, moles of ethylene oxide per mole of alcohol, and sulfated ethoxylated alkylphenols with C8 to C12 alkyl groups, preferably C8 to C10 alkyl groups and an average of 1 to 12 moles of ethylene oxide per mole of alkylphenol.
- the preferred class of alcohol ethoxysulfates are the sulfated linear alcohols, such as the C12 to C15 alcohols ethoxylated with an average of from 5 to 12 moles of ethylene oxide.
- a most preferred alcohol ethoxysulfate is prepared by sulfating a C12-C13 alcohol ethoxylated with 6.5 moles of ethylene oxide.
- the alcohol ethoxysulfate component has a higher average number of oxyethylene units per molecule than the alcohol ethoxylate component.
- the average number of oxyethylene units per molecule in the alcohol ethoxysulfate component is typically in the range of from 1 to 12, preferably from 5 to 12, and more preferably from 9 to 12, and the average number of oxyethylene units per molecule in the alcohol ethoxylate component is typically in the range of from 1 to 12, preferably from 2 to 9, and more preferably from 2 to 5.
- the amount of alcohol ethoxysulfate present in the composition is in the range of from 1 per cent by weight to 80 per cent by weight, preferably from 25 per cent by weight to 75 per cent by weight, and more preferably from 28 per cent by weight to 66 per cent by weight.
- the weight ratio of component (a), alcohol ethoxylate, to component (b), alcohol ethoxysulfate can vary widely with weight ratios in the range of from 99:1 to 1:6.
- the weight ratio of component (a) to component (b) is preferably in the range of from 5:1 to 1:5, more preferably from 3:1 to 1:3, and most preferably from 2:1 to 1:2.
- Component (c) of the liquid surface active composition is water.
- the amount of water utilized in the composition is less than 15 per cent by weight of the composition, preferably less than 10 per cent by weight, more preferably less than 7 per cent by weight, and most preferably, less than 5 per cent by weight.
- the amount of water can be controlled most efficiently when an anhydrous base, such as for example, triethanolamine or monoethanolamine, is used as the neutralizing agent.
- an anhydrous base such as for example, triethanolamine or monoethanolamine
- the amount of water can also be controlled in systems prepared with alkali metal neutralizing agents.
- the desired amount of water can be readily determined by one of ordinary skill in the art with a minimal amount of routine experimentation.
- the preparation of the liquid surface active compositions of the invention can be accomplished by mixing the components together in any manner. It is generally preferred, however, that the unneutralized alcohol ethoxysulfate product (i.e., the organic sulfuric acid ester resulting from the sulfation reaction) be added to a well-stirred mixture of alcohol ethoxylate and a concentrated base such as, for example, aqueous 50% sodium hydroxide.
- a concentrated base such as, for example, aqueous 50% sodium hydroxide.
- suitable bases include potassium hydroxide, ammonium hydroxide, triethanolamine and monoethanolamine.
- liquid compositions of the invention have a surface active material content, i.e. the percentage of alcohol ethoxylate plus the percentage of alcohol ethoxysulfate, of at least 85 per cent by weight, preferably at least 90 per cent by weight, and more preferably, at least 95 per cent by weight of said composition.
- the compositions are also substantially free, typically less than 3 per cent by weight, of organic solvents, preferably alcoholic solvents and more preferably, lower alcoholic solvents having from 1 to 5 carbon atoms.
- the liquid surfactant compositions of the invention can be utilized in a variety of detergent applications.
- the liquid surfactant compositions can be adsorbed at relatively low temperatures, about 60 °C or less, onto solid detergent materials such as, for example, sodium carbonate, in order to form dry detergent powders.
- the liquid surfactant composition can also be added to water to form liquid detergents having lower active matter concentrations.
- An alcohol ethoxylate with a C12-C13 alkyl group and containing an average of 6.5 moles ethylene oxide/mole alcohol (commercially available as NEODOL 23-6.5 Alcohol) was sulfated by reaction with gaseous SO3 in a lab-scale falling-film reactor to form an alcohol ethoxysulfate.
- the SO3/ethoxylate molar ratio was 1.05, and the reactor temperature was 65 °C.
- the acid product was prepared at a rate of 8 g/min and was directly neutralized in a pre-mixed solution containing 16.1 g aqueous 50% sodium hydroxide and 100 g of an alcohol ethoxylate with a C12-C13 alkyl group and containing an average of 5 moles ethylene oxide/mole alcohol (commercially available as NEODOL 23-5 Alcohol).
- the surfactant mixture was kept well-stirred through the use of a magnetic stirring plate, the temperature of the mixture being maintained at 55 °C with an external water bath. No gel formation was observed throughout the process. Approximately 100 g of acid product from the sulfator were added until pH 8 was obtained as measured by moistened pH paper.
- the final product was a clear flowable liquid at 20 °C and had the following analyzed composition: - 48% wt Alcohol Ethoxysulfate (Sodium Salt) - 46% wt Alcohol Ethoxylate - 5% wt Water - 1% Sodium Sulfate and trace by-products
- a viscosity of 0.2 Pa.s was measured for Surfactant Composition A at 50 °C and at a shear rate of 0.42 s ⁇ 1 using a Brookfield Model LVTD viscometer.
- Table I shows a comparison of the viscosity of Surfactant Composition A with the viscosity of an alcohol ethoxylate/water composition which contains the same amount of alcohol ethoxylate as Surfactant Composition A with the remainder of the composition being water and the viscosity of an alcohol ethoxysulfate/water composition which contains the same amount of alcohol ethoxysulfate as Surfactant Composition A with the remainder of the composition being water.
- the viscosity of Surfactant Composition A which contains 94 per cent by weight total surfactant, is substantially lower than the viscosity of both the alcohol ethoxylate/water composition and the alcohol ethoxysulfate/water composition.
- Surfactant Composition A Ten g of Surfactant Composition A were mixed with 4.1 g of NEODOL 23-5 Alcohol to produce a liquid which was clear and flowable at 20 °C and which had the following composition: - 34% wt Alcohol Ethoxysulfate (Sodium Salt) - 62% wt Alcohol Ethoxylate - 3% wt Water - ⁇ 1% wt Sodium Sulfate and trace by-products
- a viscosity of 0.1 Pa.s was measured for the composition at 50 °C and at a shear rate of 0.42 s ⁇ 1.
- Table II shows a comparison of the viscosity of Surfactant Composition B with the viscosity of an alcohol ethoxylate/water composition which contains the same amount of alcohol ethoxylate as Surfactant Composition B with the remainder of the composition being water and the viscosity of an alcohol ethoxysulfate/water composition which contains the same amount of alcohol ethoxysulfate as Surfactant Composition B with the remainder of the composition being water.
- the viscosity of Surfactant Composition B which contains 96 per cent by weight total surfactant, is substantially lower than the viscosity of both the alcohol ethoxylate/water composition and the alcohol ethoxysulfate/water composition.
- Surfactant Composition A The procedure described for Surfactant Composition A was used except that 145 g of the acid form of the alcohol ethoxysulfate were neutralized in a pre-mixed solution containing 24 g aqueous 50% sodium hydroxide and 50 g NEODOL 23-5 Alcohol. Twenty g of the product were then blended with 0.7 g of additional NEODOL 23-5 Alcohol to prepare a compositon which was a clear flowable liquid at 35 °C and above and which had the following composition: - 61% wt Alcohol Ethoxysulfate (Sodium Salt) - 32% wt Alcohol Ethoxylate - 6% wt Water - 1% wt Sodium Sulfate and trace by-products
- a viscosity of 0.7 Pa.s was measured for the composition at 50 °C and at a shear rate of 0.42 s ⁇ 1.
- Table III shows a comparison of the viscosity of Surfactant Composition C with the viscosity of an alcohol ethoxylate/water composition which contains the same amount of alcohol ethoxylate as Surfactant Composition C with the remainder of the composition being water and the viscosity of an alcohol ethoxysulfate/water composition which contains the same amount of alcohol ethoxysulfate as Surfactant Composition C with the remainder of the composition being water.
- the viscosity of Surfactant Composition C which contains 93 percent by weight total surfactant, is substantially lower than the viscosity of both the alcohol ethoxylate/water composition and the alcohol ethoxysulfate/water composition.
- Detergent Composition 1 After an aging time of one week, Detergent Composition 1 exhibited an average flow rate of 6.3 g/s thereby falling in the mid-range of the commercial products. By comparison, a powder prepared in the same manner but containing 35 g of NEODOL 23-5 Alcohol as the sole surfactant exhibited a flow rate of 5.4 g/s while a powder prepared with an excessive quantity of NEODOL 23-5 Alcohol (67 g) would not flow through the funnel.
- Detergent Composition 1 The cleaning properties of Detergent Composition 1 were evaluated using a standard radiolabeled soils' detergency testing procedure which is described in numerous technical articles, e.g. Chemical Times & Trends , Vol. 8, p. 31, and Journal of the American Oil Chemists' Society , Vol. 46, p. 537.
- Detergent Composition 1 The procedure described for Detergent Composition 1 was used except that 32 g of Surfactant Composition A were added to a powder blend containing 32 g of the sodium bicarbonate/carbonate mixture and 93 g of a light density sodium tripolyphosphate powder. The resulting detergent powder had an average flow rate of 5.0 g/s in the standard funnel flow test after one week aging. Also, the following soil removal levels were found for the detergent composition using the procedure and conditions described above for Detergent Composition 1: Soil % Soil Removal Mineral Oil 28 Synthetic Sebum 60 Clay 34
- An alcohol ethoxylate with a C12-C13 alkyl group and containing an average of 6.5 moles ethylene oxide/mole alcohol (commercially available as NEODOL 23-6.5 Alcohol) was sulfated by reaction with gaseous SO3 in a lab-scale falling-film reactor to form an alcohol ethoxysulfate.
- the SO3/ethoxylate molar ratio was 1.05, and the reactor temperature was 65°C.
- the acid product was prepared at a rate of 8 g/min and was directly neutralized in a pre-mixed solution containing 9.9 g aqueous 50% sodium hydroxide and 150 g of an alcohol ethoxylate with a C12-C13 alkyl group and containing an average of 5 moles ethylene oxide/mole alcohol (commercially available as NEODOL 23-5 Alcohol).
- the surfactant mixture was kept well-stirred through the use of a magnetic stirring plate, the temperature of the mixture being maintained at 55 °C with an external water bath. No gel formation was observed throughout the process. Approximately 60 g of acid product from the sulfator were added until pH 8 was obtained as measured by moistened pH paper.
- the final product was a clear flowable liquid at 20°C and had the following analyzed composition: - 28% wt Alcohol Ethoxysulfate (Sodium Salt) - 67% wt Alcohol Ethoxylate - 4% wt Water - 1% Sodium Sulfate and trace by-products
- Surfactant Composition D The procedure described for Surfactant Composition D was used except that 152 g of the acid form of the alcohol ethoxysulfate were neutralized in a pre-mixed solution containing 27 g aqueous 50% sodium hydroxide and 40g NEODOL 23-5 Alcohol.
- the final product was a clear flowable liquid at 40 °C and above and had the following analyzed composition: - 69% wt Alcohol Ethoxysulfate (Sodium Salt) - 22% wt Alcohol Ethoxylate - 7% wt Water - 2% wt Sodium Sulfate and trace by-products
- Detergent Composition 3 exhibited an average flow rate of 6.9 g/s thereby falling in the mid-range of the commercial products.
- a powder prepared in the same manner but containing 35 g of NEODOL 23-5 Alcohol as the sole surfactant exhibited a flow rate of 5.9 g/s while a powder prepared with an excessive quantity of NEODOL 23-5 Alcohol (67 g) would not flow through the funnel.
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Detergent Compositions (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US34322789A | 1989-04-26 | 1989-04-26 | |
| US34323189A | 1989-04-26 | 1989-04-26 | |
| US343231 | 1989-04-26 | ||
| US343227 | 1989-04-26 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EP0399581A2 true EP0399581A2 (fr) | 1990-11-28 |
| EP0399581A3 EP0399581A3 (fr) | 1990-12-27 |
Family
ID=26993385
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP19900201047 Withdrawn EP0399581A3 (fr) | 1989-04-26 | 1990-04-25 | Compositions tensio-actives |
Country Status (5)
| Country | Link |
|---|---|
| EP (1) | EP0399581A3 (fr) |
| JP (1) | JPH0362899A (fr) |
| KR (1) | KR900016443A (fr) |
| PT (1) | PT93859A (fr) |
| TW (1) | TW201329B (fr) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0431653A3 (en) * | 1989-08-31 | 1993-03-10 | Shell Internationale Research Maatschappij B.V. | Liquid surface active compositions |
| WO2006089013A1 (fr) * | 2005-02-14 | 2006-08-24 | The Dial Corporation | Composition de detergent amelioree presentant un plus grand pouvoir blanchissant |
| WO2009015137A1 (fr) * | 2007-07-24 | 2009-01-29 | Shell Oil Company | Procédé destiné à fabriquer un produit nettoyant à base d'alcool secondaire |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW391981B (en) * | 1996-12-02 | 2000-06-01 | Kao Corp | Surfactant formulation |
| JP4772415B2 (ja) * | 2004-08-06 | 2011-09-14 | 花王株式会社 | 単核性洗剤粒子群の製造方法 |
| JP4965821B2 (ja) * | 2005-06-08 | 2012-07-04 | 花王株式会社 | 界面活性剤組成物 |
| JP6155133B2 (ja) * | 2012-08-29 | 2017-06-28 | ライオン株式会社 | 液体洗浄剤 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ZA722326B (en) * | 1971-05-04 | 1973-11-28 | Colgate Palmolive Co | Liquid detergent and laundering process |
| US3812041A (en) * | 1972-06-23 | 1974-05-21 | Colgate Palmolive Co | Non-gelling heavy duty liquid laundry detergent |
| ZA734138B (en) * | 1972-07-20 | 1975-01-29 | Colgate Palmolive Co | Heavy duty liquid laundry detergent |
| GB8625104D0 (en) * | 1986-10-20 | 1986-11-26 | Unilever Plc | Detergent compositions |
-
1990
- 1990-04-23 KR KR1019900005689A patent/KR900016443A/ko not_active Withdrawn
- 1990-04-24 JP JP2106685A patent/JPH0362899A/ja active Pending
- 1990-04-24 PT PT93859A patent/PT93859A/pt not_active Application Discontinuation
- 1990-04-25 EP EP19900201047 patent/EP0399581A3/fr not_active Withdrawn
- 1990-04-28 TW TW079103494A patent/TW201329B/zh active
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0431653A3 (en) * | 1989-08-31 | 1993-03-10 | Shell Internationale Research Maatschappij B.V. | Liquid surface active compositions |
| WO2006089013A1 (fr) * | 2005-02-14 | 2006-08-24 | The Dial Corporation | Composition de detergent amelioree presentant un plus grand pouvoir blanchissant |
| WO2006088928A1 (fr) * | 2005-02-14 | 2006-08-24 | The Dial Corporation | Composition surfactante contenant un sulfate d'alcool-ethoxy destinee a s'utiliser dans des detergents a lessive et processus de fabrication correspondant |
| US7754669B2 (en) | 2005-02-14 | 2010-07-13 | The Dial Corporation | Detergent composition with enhanced whitening power |
| WO2009015137A1 (fr) * | 2007-07-24 | 2009-01-29 | Shell Oil Company | Procédé destiné à fabriquer un produit nettoyant à base d'alcool secondaire |
| US20110092406A1 (en) * | 2007-07-24 | 2011-04-21 | Kirk Herbert Raney | Process for making a secondary alcohol cleaning product |
Also Published As
| Publication number | Publication date |
|---|---|
| TW201329B (fr) | 1993-03-01 |
| EP0399581A3 (fr) | 1990-12-27 |
| JPH0362899A (ja) | 1991-03-18 |
| KR900016443A (ko) | 1990-11-13 |
| PT93859A (pt) | 1990-11-20 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4464292A (en) | Mixed ethoxylated alcohol/ethoxy sulfate surfactants and synthetic detergents incorporating the same | |
| US5922670A (en) | Dimeric alcohol-bis and trimeric alcohol-tris-sulphates and ether sulphates thereof | |
| US4207421A (en) | Biodegradable, alkali stable, non-ionic surfactants | |
| EP0238638B1 (fr) | Procede de preparation d'une composition detergente particulaire | |
| JPH064878B2 (ja) | エタノ−ルを含まない液体洗濯洗剤組成物 | |
| US3786003A (en) | Liquid detergent compositions | |
| AU652812B2 (en) | Process for preparing a liquid surfactant composition | |
| EP0482687A1 (fr) | Composition coulable liquide concentrée | |
| US3168478A (en) | Highly alkaline surface active compositions | |
| US3501409A (en) | Detergent-hydrotrope composition | |
| US5215683A (en) | Highly concentrated liquid surface active compositions containing alcohol ethoxylate and alcohol ethoxysulfate | |
| US4608197A (en) | Alkoxylated ether sulfate anionic surfactants from branched chain plasticizer alcohols | |
| US4592875A (en) | Alkoxylated ether sulfate anionic surfactants from plasticizer alcohol mixtures | |
| KR970011314B1 (ko) | (a) 술폰화된 불포화 지방산의 알칼리, 암모늄 및/또는 아민염과 (b) 알콕시화 알킬 및/또는 알켄일 알코올 및/또는 술포숙신산 에스테르를 함유하는 혼합물의 습식제로서의 용도 | |
| US5209874A (en) | Liquid surface active compositions | |
| EP0399581A2 (fr) | Compositions tensio-actives | |
| JPH07506607A (ja) | ペースト状洗剤の製造方法 | |
| US2932616A (en) | Detergent compositions | |
| US3959186A (en) | Process for manufacturing detergent builders | |
| US3565939A (en) | Partial neutralization of sulfates of ethoxylated alcohols | |
| US3290254A (en) | Methyl-beta-hydroxydodecyl sulfoxide containing detergent compositions | |
| US4412945A (en) | Aqueous high concentration slurry of alcohol ethoxylate | |
| US4855075A (en) | Ethoxylates of alkyl and alkenyl catechols | |
| EP0431653A2 (fr) | Composition liquide tensio-active | |
| US4436642A (en) | Nonionic surfactants for automatic dishwasher detergents |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PUAI | Public reference made under article 153(3) epc to a published international application that has entered the european phase |
Free format text: ORIGINAL CODE: 0009012 |
|
| PUAL | Search report despatched |
Free format text: ORIGINAL CODE: 0009013 |
|
| AK | Designated contracting states |
Kind code of ref document: A2 Designated state(s): BE DE ES FR GB IT NL SE |
|
| AK | Designated contracting states |
Kind code of ref document: A3 Designated state(s): BE DE ES FR GB IT NL SE |
|
| 17P | Request for examination filed |
Effective date: 19910418 |
|
| STAA | Information on the status of an ep patent application or granted ep patent |
Free format text: STATUS: THE APPLICATION HAS BEEN WITHDRAWN |
|
| 18W | Application withdrawn |
Withdrawal date: 19930225 |