GB2158080A - End-blocked nonionic surfactants - Google Patents
End-blocked nonionic surfactants Download PDFInfo
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- GB2158080A GB2158080A GB08505279A GB8505279A GB2158080A GB 2158080 A GB2158080 A GB 2158080A GB 08505279 A GB08505279 A GB 08505279A GB 8505279 A GB8505279 A GB 8505279A GB 2158080 A GB2158080 A GB 2158080A
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- alkyl group
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- 239000002736 nonionic surfactant Substances 0.000 title description 6
- 150000001875 compounds Chemical class 0.000 claims abstract description 37
- 239000000203 mixture Substances 0.000 claims abstract description 30
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 11
- 238000009472 formulation Methods 0.000 claims abstract description 11
- 238000004140 cleaning Methods 0.000 claims abstract description 5
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 16
- 239000000463 material Substances 0.000 claims description 10
- -1 alkylbenzyl halide Chemical class 0.000 claims description 9
- 125000003438 dodecyl 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 claims description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 6
- 235000011121 sodium hydroxide Nutrition 0.000 claims description 6
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 125000002947 alkylene group Chemical group 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 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 claims description 2
- 125000002347 octyl 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])[H] 0.000 claims description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 claims 2
- 239000000843 powder Substances 0.000 abstract description 10
- 239000003518 caustics Substances 0.000 abstract description 6
- 230000000694 effects Effects 0.000 abstract description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 239000000047 product Substances 0.000 description 9
- 239000006260 foam Substances 0.000 description 8
- 238000004851 dishwashing Methods 0.000 description 6
- 230000000903 blocking effect Effects 0.000 description 5
- 238000005187 foaming Methods 0.000 description 5
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000013065 commercial product Substances 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
- 238000009736 wetting Methods 0.000 description 3
- YBQNEYHTRLYDIB-UHFFFAOYSA-N 1-(chloromethyl)-4-decylbenzene Chemical compound CCCCCCCCCCC1=CC=C(CCl)C=C1 YBQNEYHTRLYDIB-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 230000003254 anti-foaming effect Effects 0.000 description 2
- HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000006482 condensation reaction Methods 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 235000018102 proteins Nutrition 0.000 description 2
- 102000004169 proteins and genes Human genes 0.000 description 2
- 108090000623 proteins and genes Proteins 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000002689 soil Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- 239000012085 test solution Substances 0.000 description 2
- ISXDOPCKEDRLAY-UHFFFAOYSA-N 1-chlorotridecylbenzene Chemical compound CCCCCCCCCCCCC(Cl)C1=CC=CC=C1 ISXDOPCKEDRLAY-UHFFFAOYSA-N 0.000 description 1
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 1
- 241000004297 Draba Species 0.000 description 1
- 102100024739 E3 ubiquitin-protein ligase UHRF1 Human genes 0.000 description 1
- 229920005682 EO-PO block copolymer Polymers 0.000 description 1
- 101100483728 Homo sapiens UHRF1 gene Proteins 0.000 description 1
- 102000014171 Milk Proteins Human genes 0.000 description 1
- 108010011756 Milk Proteins Proteins 0.000 description 1
- BACYUWVYYTXETD-UHFFFAOYSA-N N-Lauroylsarcosine Chemical compound CCCCCCCCCCCC(=O)N(C)CC(O)=O BACYUWVYYTXETD-UHFFFAOYSA-N 0.000 description 1
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 1
- 239000004115 Sodium Silicate Substances 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000001348 alkyl chlorides Chemical class 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
- 229940073608 benzyl chloride Drugs 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 235000021239 milk protein Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000005086 pumping Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 108700004121 sarkosyl Proteins 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000019795 sodium metasilicate Nutrition 0.000 description 1
- DZCAZXAJPZCSCU-UHFFFAOYSA-K sodium nitrilotriacetate Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)CN(CC([O-])=O)CC([O-])=O DZCAZXAJPZCSCU-UHFFFAOYSA-K 0.000 description 1
- NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 1
- 229910052911 sodium silicate Inorganic materials 0.000 description 1
- 235000019832 sodium triphosphate Nutrition 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- UEUXEKPTXMALOB-UHFFFAOYSA-J tetrasodium;2-[2-[bis(carboxylatomethyl)amino]ethyl-(carboxylatomethyl)amino]acetate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]C(=O)CN(CC([O-])=O)CCN(CC([O-])=O)CC([O-])=O UEUXEKPTXMALOB-UHFFFAOYSA-J 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 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
- C11D1/72—Ethers of polyoxyalkylene glycols
- C11D1/721—End blocked ethers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
- C07C43/14—Unsaturated ethers
- C07C43/178—Unsaturated ethers containing hydroxy or O-metal groups
- C07C43/1785—Unsaturated ethers containing hydroxy or O-metal groups having more than one ether bound
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/32—Polymers modified by chemical after-treatment
- C08G65/329—Polymers modified by chemical after-treatment with organic compounds
- C08G65/337—Polymers modified by chemical after-treatment with organic compounds containing other elements
-
- 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
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Materials Engineering (AREA)
- Life Sciences & Earth Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- General Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Detergent Compositions (AREA)
Abstract
Alkylbenzyl poly(oxyalkylene) derivatives of the formula <IMAGE> wherein R1 is a straight or branched chain 1-4C alkyl group; R2 is a straight or branched chain 4-20C alkyl group; R3 and R4 are each, independently, H or CH3; n and m are each integers wherein n + m does not exceed 20 have good nonionic surface activity, biodegradability and are stable to caustic powders. The compounds are useful in alkaline cleaning compositions, such as dishwater products, and also in rinse-aid formulations for use in automatic dishwashers.
Description
SPECIFICATION
End-blocked nonionic surfactants
The present invention relates to end-blocked nonionic surfactants. More particularly, it relates to new alkylbenzyl poly(oxyalkylene) derivatives useful as nonionic surfactants.
In the past, a number of classes of compounds have been used, in detergents and janitorial compositions, as non-ionic surface active agents. Examples of these include amine ethoxylate propoxylates, benzylblocked alkylphenol alkoxylates and ethylene oxide-propylene oxide block copolymers. These materials suffer the major disadvantage that they lack biodegradability and are unstable on solid caustic soda.
Furthermore, such materials as are commercially available are ill-defined or have incompletely characterisable chemical structure.
In an attempt to overcome the problem of lack of biodegradability of prior nonionic surfactants, alcohol ethoxylate propoxylates, having molecular weights less than 1000, were used. Unfortunately, these materials have poor dispersibility in water at temperatures above their cloud points. In addition, they are unstable in the presence of solid caustic powders, e.g. caustic soda, as in the case of the earlier nonionics.
Futher attempts to overcome the drawbacks of the prior art materials involved "blocking" the terminal hydroxyl group in fatty alcohol ethoxylates with alkyl chlorides. The procedures used, however, were difficult and they made use of toxic and expensive materials. Similarly blocked non-ionics using benzyl chloride as alkylating agent were introduced although the commercial product was only about 70% blocked, indicating the poor efficiency of the blocking procedure.
We have now discovered a range of compounds having good nonionic surface activity which are biodegradable and stable to caustic powders. Furthermore, we have discovered that these compounds can be prepared by a process which achieves greater than 90% blocking.
The present invention provides new compounds which are represented by the following general formula
wherein R1 is a straight or branched chain alkyl group having from 1 to 4 carbon atoms; R2 is a straight or branched chain alkyl group having from 4 to 20 carbon atoms; R3 and R4 are each, independently, H or -CH3, and n and m are each integers wherein the sum n + m is not greater than 20.
As we have stated above, the group R1 is a 1 to 4 C alkyl, such as methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl and tert-butyl. The alkyl group R2 attached to the phenyl ring of the blocking group is a straight or branched chain group containing from 4to 20 carbon atoms, preferably 8 to 12 carbon atoms.
Preferred examples of suitable R2 groups include straight and branched chain octyl, decyl and dodecyl groups. A particularly preferred R2 group is n-dodecyl.
The sum n + m is not greater than 20 and will usually lie within the range of from 5 to 15, more particularly within the range 8 to 14. A preferred value of n + m is 10.
Some preferred compounds of the present invention are as follows:
The present invention also provides a process for preparing a compound of the formula I above which process comprises reacting a lowr alcohol of the formula R1OH, wherein R1 is as defined above, with an alkylene oxide selected from ethylene oxide and propylene oxide, and then reacting the ethoxylated andlor propoxylated material with an alkylbenzyl halide having the formula
wherein X is a halogen atom, preferably a chlorine atom. In a preferred embodiment, the ethoxylated and/or propoxylated material is reacted with a mixture of alkylbenzyl chlorides, such as a mixture of Cs and Clo alkylbenzyl chlorides to give a mixture of reaction products.
If it is desired to form a compound of formula I wherein R3 is H and R4 is -OH3, then the lower alcohol is first reacted with ethylene oxide and the ethoxylated product is then reacted with propylene oxide. If the desired compound of formula I has R3=CH3 and R4=H, then the alcohol is first propoxylated and the alkyl propoxylate is then ethoxylated. The amount of reactants used in this step, of course, depend upon the desired values of n and m in the final compound. Usually, the amounts of alkylene oxide used will be sufficient such that the sum of n f m is within the range of from 5 to 15. The alkoxylated lower alcohol is then condensed with the alkylbenzyl chloride. The condensation reaction will usually be conducted in the presence of an alkali metal hydroxide, typically NaOH.The condensation reaction is preferably phase transfer catalysed with, for instance, a catalytic amount of a tetraalkyl ammonium halide. By the use of this process, it is possible to achieve a blocking efficiency of greater than 90%. Furthermore, it should be noticed that, in the above-described process, end-blocking of the molecule and the introduction of the hydrophobe into the molecule are carried out in one step unlike prior art processes. Thus, by the process of the invention, it is possible to make end blocked non ionics at low cost.
The compounds of the invention have relatively low molecular weight and meet E.E.C. legislation on biodegradability (Directive 82/242/EEC). They are stable on solid caustic powders and have excellent defoaming properties, good wetting and detergency. The compounds of the invention are, therefore, particularly well suited to use in strongly alkaline cleaning compositions in combination with solid caustic powders, such as powdered caustic soda. In particular, the compounds of the present invention are especially useful as low-foaming or anti-foaming ingredients in alkaline powder dishwashing products. They may also be used advantageously in rinse-aid formulations for automatic dishwashing and may control or prevent foam generated by or stabilised by food soils.
Example 1
1 mold of n-butanol was ethoxylated with 10 moles of ethylene oxide by a conventional method. The ethoxylated product (150 g) was then charged together with 50% caustic soda solution (80 g) and, as catalyst, benzyltriethylammonium chloride (2.5 g). The temperature of this mixture was raised to 90-950C at which temperature a mixture of p-octyl and p-decylbenzyl chloride (45 g) was run in over a period of 3 hours. The reaction mixture was then heated to 1 10"C and maintained at that temperature for 1 hour. After cooling, the reaction mixture was washed with water to remove salt, unreacted polyglycol and catalyst. The product comprised a mixture of:
Example 2
The procedure of Example 1 was repeated, except that methanol, instead of n-butanol, was used.The product comprised a m mixture of Example 3
The procedure of Example 1 was repeated except that dodecyl benzyl chloride, instead of p-octyl and p-decyl benzyl chloride, was used.
The product comprised
Some of the properties of the products obtained in Examples 1, (A), and 2, (B), were measured and compared with those obtained for a prior art unblocked non-ionic surfactant, nonyl phenol 9.5 mole ethoxylate (NP 95). These are set out below.
A B NP95
1. Cloud point, at concentration
of 1% in water, in "C 34 47 52
2. Foam (by Ross Miles), at a
concentration of 0.1% in water
and temperature 5"C below
cloud point, in mm. 41 61 100
3. Foam at cloud point, at
concentration of 0.1% in
water, in mm. 30 28 66
4. Wetting (by Draves) at a
concentration of 0.1% in
water and temperature 5"C below cloud point, in seconds 11 21 4
5. Stability on caustic good good very poor.
These results show that the compositions A and B, which are in accordance with the present invention, show a big foam reduction compared to the prior art compound and suffer only small loss in wetting properties.
The compounds of this invention are advantageoiisly used as low-foaming or antifoaming ingredients in alkaline powder dishwashing products.
Example 4
An alkaline powder dishwashing product with good cleaning power and controlled foaming characteristics is prepared by blending the following:
Sodium metasilicate 30% by weight
Soda ash 38% by weight *Trisodium nitrilotriaceticacid powder 10% by weight
Sodium tripolyphosphate 20% by weight
Suitable compound of present invention 2% by weight
*e.g. Nervanaid NTA Conc. Powder, a trade name of A.B.M. Chemicals Ltd.
wherein the suitable compound of the present invention is one or a mixture of more than one of the following:
a) A compound according to formula 1 wherein (n + m)= 10 and
R3 = R4 = H and R1 = C2H5 and R2 = C12H25
b) a compound according to formula 1 wherein
(n + m) = 6 and
R3 = R4 = H and R, = C4H (n-butyl) and R2 = C12H25.
c) a compound according to formula 1 wherein
(n + m) = 14and R3 = R4 = H and R1 = C4H9 (n-butyl)
and R2 = C12H2.
The compounds of the invention are advantageously used in rinse-aid formulations for automatic
dishwashing. Spotless quick-drying is achieved without causing subsequent foaming problems in
those machines where rinse water is re-cycled into the wash-water. Furthermore formulations
containing compounds of the present invention may control or prevent foam generated or stabilised
by food soils.
Example 5
Rinse aid formulations for automatic dishwashing according to the following recipes give spotless
quick-drying:
Suitable compound of present invention 25%
Dipropylene glycol 10%
N-lauroyl sarcosinate 1%
Water 64%
Where a suitable compound of the present invention includes a mixture of compounds according to formula 1, wherein, for example, (n + m) = 6 and 14 and R3 = R4 = H and R1 = C4H9 (n-butyl) and R2 = C12H25. Such mixture comprises 60% of such compound wherein (n + m) = 14 and 40% of such compound wherein (n + m) = 6, and when the formulation of Example 5 is made with this mixture of non-ionic surface active agents a formulation (Formulation 1) with properties superior to those of current commercial formulations is obtained, as measured in the following tests: :
Actives % Protein Haze Temp. Dispersibility Glass rinse (Drying at 11000) Foam (mm) ("C) in water at appearance 80"C at 80 C Formulation 1 36 24 61 Excellent Excellent
Commercial ProductA 30 184 51 Fair Very good
Commercial Product B 50 50 60 Good Fair
Commercial Product C 32 90 47 Good Fair Protein foam tests measure the height of foam produced in a dynamic foaming test with 100 ppm
of rinse aid in water of 150 ppm hardness in the presence of 0.25% milk protein and 0.36% alkaline
builders at a temperature of 60"C. The test involes pumping the test solution at a pressure of 5 psi through a 1.8 mm orifice with a fall of 750 mm onto the surface of the test solution with recirculation for 5 min.
Claims (12)
1. A compound which is represented by the following general formula:
wherein R1 is a straight or branched chain 1-4C alkyl group; R2 is a straight or branched chain 4-20C alkyl group; R3 and R4 are each, independently, H or -CH3; and n and m are each integers wherein the sum n + m is not greater than 20.
2. A compound as claimed in claim 1, wherein R2 is a straight or branched chain alkyl group having from 8 to 12 carbon atoms.
3. A compound as claimed in claim 2, wherein R2 is a straight or branched chain octyl, decyl or dodecyl group.
4. A compound as claimed in any one of claims 1 to 3, wherein the sum of n + m is in the range of from 5 to 15.
5. A compound as claimed in any one of claims 1 to 4, wherein R1 is n-butyl; R2 is a substantially linear dodecyl; R3 and R4 are both H and the sum n + m is in the range of from 5 to 15.
6. A compound as claimed in any one of claims 1 to 4, wherein R1 is ethyl; R2 is a substantially linear dodecyl; R3 and R4 are both H and the sum n + m is in the range of from 5 to 15.
7. A method of preparing a compound having the following general formula:
wherein R1 is a straight or branched chain 1-4C alkyl group; R2 is a straight or branched chain 4-20C alkyl group; R3 and R4 are each, independently, H or -CH3; and n and m are each integers wherein the sum n + m is not greater than 20,
which method comprises reacting an alochol of the formula R1OH,where R1 is as defined above, with an alkylene oxide selected from ethylene oxide, propylene oxide and mixtures thereof and then reacting the resulting alkoxylated material with an alkylbenzyl halide having the formula
wherein R2 is as defined above and Xis a halogen atom.
8. A method of preparing a compound having the following general formula:
wherein R1 is a straight or branched chain 1-4C alkyl group; R2 is a straight or branched chain 4-20C alkyl group; and n and m are each integers wherein the sum n + m is not greater than 20, which method comprises reacting an alochol of the formula R1OH, where R1 is as defined above, with ethylene oxide, then reacting the resulting ethoxylated product with propylene oxide and then reacting the resulting propoxylated material with an alkylbenzyl halide of the formula:
where R3 is as defined above and X is a halogen atom.
9. A method of preparing a compound having the following general formula:
wherein R1 is a straight or branched chain 1-4C alkyl group; R2 is a straight or branched chain 4-20C alkyl group; and n and m are each integers wherein the sum n + m is not greater than 20, which method comprises reacting an alcohol of the formula R1OH, where R1 is as defined above, with propylene oxide, reacting the resulting propoxylated material with ethylene oxide and then reacting the resulting ethoxylated product with an alkylbenzyl halide of the formula
wherein R2 is as defined above and X is a halogen atom.
10. A cleaning composition comprising a mixture of caustic soda and at least one compound as claimed in claim 1.
11. A cleaning composition substantially as hereinbefore described in Example 4.
12. A rinse aid formulation for use in an automatic dishwater substantially as hereinbefore described in ExampleS.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB848405521A GB8405521D0 (en) | 1984-03-02 | 1984-03-02 | End-blocked nonionic surfactants |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| GB8505279D0 GB8505279D0 (en) | 1985-04-03 |
| GB2158080A true GB2158080A (en) | 1985-11-06 |
| GB2158080B GB2158080B (en) | 1987-02-25 |
Family
ID=10557480
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB848405521A Pending GB8405521D0 (en) | 1984-03-02 | 1984-03-02 | End-blocked nonionic surfactants |
| GB08505279A Expired GB2158080B (en) | 1984-03-02 | 1985-03-01 | End-blocked nonionic surfactants |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB848405521A Pending GB8405521D0 (en) | 1984-03-02 | 1984-03-02 | End-blocked nonionic surfactants |
Country Status (1)
| Country | Link |
|---|---|
| GB (2) | GB8405521D0 (en) |
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0275476A1 (en) * | 1986-12-22 | 1988-07-27 | Henkel Kommanditgesellschaft auf Aktien | Anti-foam agents for polymer dispersions |
| EP0337760A2 (en) * | 1988-04-14 | 1989-10-18 | Unilever Plc | Detergent compositions |
| EP0346111A2 (en) * | 1988-06-09 | 1989-12-13 | The Procter & Gamble Company | Liquid automatic dishwashing detergent compositions containing bleach-stable nonionic surfactant |
| WO2000050549A2 (en) * | 1999-02-22 | 2000-08-31 | The Procter & Gamble Company | Cleaning compositions containing selected nonionic surfactants |
| WO2000050551A1 (en) * | 1999-02-22 | 2000-08-31 | The Procter & Gamble Company | Automatic dishwashing compositions comprising selected nonionic surfactants |
| WO2001042410A1 (en) * | 1999-12-08 | 2001-06-14 | The Procter & Gamble Company | Compositions including ether-capped poly(oxyalkylated) alcohol surfactants |
| US6506945B2 (en) | 1999-12-08 | 2003-01-14 | The Procter & Gamble Company | Process for preparing ether-capped poly(oxyalkylated) alcohol surfactants |
| US6686330B2 (en) | 1999-12-08 | 2004-02-03 | The Procter & Gamble Company | Compositions including ether-capped poly (oxyalkylated) alcohol wetting agents |
| US6844309B1 (en) | 1999-12-08 | 2005-01-18 | The Procter & Gamble Company | Ether-capped poly(oxyalkylated) alcohol surfactants |
| US7012052B1 (en) | 1999-02-22 | 2006-03-14 | The Procter & Gamble Company | Automatic dishwashing compositions comprising selected nonionic surfactants |
| JP2007016031A (en) * | 1999-12-08 | 2007-01-25 | Procter & Gamble Co | Ether-capped poly(oxyalkylated)alcohol surfactant |
-
1984
- 1984-03-02 GB GB848405521A patent/GB8405521D0/en active Pending
-
1985
- 1985-03-01 GB GB08505279A patent/GB2158080B/en not_active Expired
Cited By (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0275476A1 (en) * | 1986-12-22 | 1988-07-27 | Henkel Kommanditgesellschaft auf Aktien | Anti-foam agents for polymer dispersions |
| US4981893A (en) * | 1986-12-22 | 1991-01-01 | Henkel Kommanditgesellschaft Auf Aktien | Foam inhibitors for polymer dispersions |
| EP0337760A2 (en) * | 1988-04-14 | 1989-10-18 | Unilever Plc | Detergent compositions |
| EP0337760A3 (en) * | 1988-04-14 | 1992-04-29 | Unilever Plc | Detergent compositions |
| EP0346111A2 (en) * | 1988-06-09 | 1989-12-13 | The Procter & Gamble Company | Liquid automatic dishwashing detergent compositions containing bleach-stable nonionic surfactant |
| EP0346111A3 (en) * | 1988-06-09 | 1990-07-04 | The Procter & Gamble Company | Liquid automatic dishwashing detergent compositions containing bleach-stable nonionic surfactant |
| WO2000050549A3 (en) * | 1999-02-22 | 2000-11-02 | Procter & Gamble | Cleaning compositions containing selected nonionic surfactants |
| WO2000050551A1 (en) * | 1999-02-22 | 2000-08-31 | The Procter & Gamble Company | Automatic dishwashing compositions comprising selected nonionic surfactants |
| WO2000050549A2 (en) * | 1999-02-22 | 2000-08-31 | The Procter & Gamble Company | Cleaning compositions containing selected nonionic surfactants |
| US7012052B1 (en) | 1999-02-22 | 2006-03-14 | The Procter & Gamble Company | Automatic dishwashing compositions comprising selected nonionic surfactants |
| WO2001042410A1 (en) * | 1999-12-08 | 2001-06-14 | The Procter & Gamble Company | Compositions including ether-capped poly(oxyalkylated) alcohol surfactants |
| US6506945B2 (en) | 1999-12-08 | 2003-01-14 | The Procter & Gamble Company | Process for preparing ether-capped poly(oxyalkylated) alcohol surfactants |
| US6593287B1 (en) | 1999-12-08 | 2003-07-15 | The Procter & Gamble Company | Compositions including ether-capped poly(oxyalkylated) alcohol surfactants |
| US6686330B2 (en) | 1999-12-08 | 2004-02-03 | The Procter & Gamble Company | Compositions including ether-capped poly (oxyalkylated) alcohol wetting agents |
| US6844309B1 (en) | 1999-12-08 | 2005-01-18 | The Procter & Gamble Company | Ether-capped poly(oxyalkylated) alcohol surfactants |
| JP2007016031A (en) * | 1999-12-08 | 2007-01-25 | Procter & Gamble Co | Ether-capped poly(oxyalkylated)alcohol surfactant |
Also Published As
| Publication number | Publication date |
|---|---|
| GB8405521D0 (en) | 1984-04-04 |
| GB2158080B (en) | 1987-02-25 |
| GB8505279D0 (en) | 1985-04-03 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PCNP | Patent ceased through non-payment of renewal fee |