US3923678A - Liquid cleansing agent concentrates - Google Patents

Liquid cleansing agent concentrates Download PDF

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US3923678A
US3923678A US519247A US51924774A US3923678A US 3923678 A US3923678 A US 3923678A US 519247 A US519247 A US 519247A US 51924774 A US51924774 A US 51924774A US 3923678 A US3923678 A US 3923678A
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cleansing agent
agent concentrates
weight
ethylene oxide
concentrates
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US519247A
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Hans-Jerg Kleiner
Otto Koller
Karl-Heinz Schneider
Gerhart Schneider
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Hoechst AG
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Hoechst AG
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    • 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
    • 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
    • C11D1/34—Derivatives of acids of phosphorus
    • C11D1/342—Phosphonates; Phosphinates or phosphonites
    • 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
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/36—Organic compounds containing phosphorus
    • C11D3/361—Phosphonates, phosphinates or phosphonites

Definitions

  • R is an aliphatic radical having 4 to 16 car-
  • R is an aliphatic radical having 1 to 4 car- UNITED STATES PATENTS bon atoms
  • Y is hydrogen or an alkaline-metal ion.
  • hydrotropic substances as for example toluene sulfonate, xylene sulfonate and cumol sulfonate
  • these sulfonates frequently used for this purpose as hydrotropic substances generally complywith the requirements in the case'of detergent concentrates on the basis of anion-active detergents, they are ineffective when using non-ionic, surface-active products.
  • cleansing agents on the basis of non-ionic surface-active compounds are preferred in practice with regard to those basing on anion-active compounds. Therefore, there is a need for hydrotropic solubilizers, which are suitable for such cleansing agent concentrates on the basis of non-ionic tensides.
  • phosphoric acid esters such as for example phosphoric acid monoor diesters of the alkylaryl-polyglycol ethers or of the alkyl-polyglycol ethers.
  • hydrotropic properties of these phosphoric acid esters are only slightly marked, and their effectis not sufficient to dissolve until clear or to disperse the amounts of non-ionic, surface-active com pounds required for the preparation of cleansing agent concentrates, in the presence of high electrolyte concentrations.
  • phosphinic acids or salts thereof of the general formula I wherein R is a straight-chained or branched alkylor alkenyl radical having 4 to 16 carbon atoms, preferably and Y is hydrogen or the sodium or potassium ion have excellent hydrotropic properties superior to the phosphoric acid esters mentioned, with regard to non-ionic, surface-active compounds, and are therefore, especially suitable for the preparationof liquid aqueous cleansing agent concentrates on th e'basis-of non ionic, surface-active compounds.
  • the invention further relates to liquid aqueous cleansing agent concentrates on the basis of non-ionic, surface-active compounds,characterized by a content of phosphinic acid derivatives of the general formula I sceletton substances, as they are described for example in the standard work Schwartz, Perry, Berch ;Surface Active Agents and Detergents/volume ll, (l958),
  • these sceletton substances in the aqueous cleansing agent concentrates is generally up to 35 by weight, especially 5 to 30 by weight.
  • Such sceletton substances are above all alkaliorthoand -polyphosphates, as for example sodium tripolyphosphate or potassium pyrophosphate, in amounts of up to about 20 by weight, preferably 8 to 15 by weight, or organic complexformingagents, as for example ethylene-diamine-tetra-acetate, trisodium citrate or the sodium of the nitrilo-triacetic acid, also in amounts of up to about 20 by weight, especially up to about 12 by weight, and alkali silicates, as for example sodium meta-silicate or sodium-di orftrisilicate, in amounts of up to about 10 by weight, especially up to about 8% by weight.
  • alkali silicates as for example sodium meta-silicate or sodium-di orftrisilicate
  • aqueous cleansing agent concentrates of the invention may furthermore contain alkali liquors in amounts of up to about 5 by weight, preferably up to 3 by weight, as well as, if required, further usual auxiliaries.
  • the content of the aqueous cleansing agent concentrates according to the invention of non-ionic detergent raw materials is generally at about 1 to 10 by weight, preferably 2 to 5 by weight, and the content thereof of the phosphinic acid derivatives of the formula I is at about 1 to 5 by weight, preferably L5 to 3.0 %by weight.
  • the content of water of the concentrates is mostly adjusted to about 65 by weight and the pH-value is adjusted to the range of from 8 to 14.
  • Non-ionic surface-active products as they may be contained in the liquid cleansing agent concentrates according to the invention, are described for example in the standard work Schwartz, Perry, Berch Surface Active Agents and Detergents, Volume ll, (1958), pages I20 to I38.
  • Preferred non-ionic detergent raw materials are for example:
  • Alkylphenol oxethylates especially those having 8 to 12 carbon atoms in the alkyl radical and a content of about 4 to 15 oxethylene units
  • radical R represents methyl. Also preferred are compounds of the formula I, the alkyl radicals of which contain, on the whole, at least 7 carbon atoms.
  • Alkylamine-oxyethylates especially those having 1O Turbid solutioninclining to the separation of the alkyl radicals of about to 20 carbon atoms and layers. about 4 to oxethylene units in the molecule as
  • the Examples 1 to 15 correspond to the present inwell as vention, the Examples 16 to 45 are comparative prode.
  • Fatty acids oxethylates especially those with alkyl ucts according to the state of the art.
  • the composition radicals having about 8 to carbon atoms and 15 ofthe cleansing agent concentrates in this Table is indiabout 4 to 15 oxethylene units in the molecule. cated ineach case in percent.
  • the phosphinic acid derivatives of the formula I used may be in the invention as a constituent of the liquid cleansing used for example as liquid alkaline washing detergents agent concentrates have not only the excellent hydrofor dish washers. Especially interesting is, however, tropic properties but also, surprisingly, a good stability 20 their use as cleansers for industrial purposes in hightowards alkali liquors. They are normally soluble until pressure and vapor stream cleansing apparatures. clear in a concentration of, for example, 10 g/l in a Great value is set on the small foaming effect and a high sodium hydroxide solution at room temperature. cleansing and decreasing capacity.
  • non-ionic surface-active compounds view is above all their capacity of imparting to non- 25 are .preferred for this application; they meet the reionic, surface-active products a sufficient'stability in quirements when used together with the phosphates, salt-containing solutions.
  • silicates and alkalies and the phosphinic acids accord- Compounds of the formula 1 preferably used according to the invention.
  • the compositions indicated in the ing to the invention are those, in which the radical R Table as Examples may, of. course, be varied to a large represents and alkyl radical containing 6 to 10 carbon extent as to their constituents and the corresponding atoms, especially the octyl radical, and wherein the application.
  • Examples of cleansing agent concentrates Components l 2v 3, 4 5 6 7 8 9 10 ll I2 13 I4 15 Methyloctyl- 2,5 2,5 2 2 2 2 2 2 2 2 2 2 2 2 2 phosphinic acid Phosphoric acidmono-l-diester of lauryl alcohol ethylene oxide Phosphoric acidmono-l-diester of nonyl phenol 4 mols of ethylene oxide Nonyl phenol i 3 3 3 l0 mols ethylene oxide (C J-fatty- 3 3 3 alcohol 9 mols of ethylene oxide Octadecenyl amine 3 3 3 3 ethylene oxide 'Oleic'acid 6 mols 3 3 3 of ethylene oxide I Polypropylene- 3 3 3 glycol (MG l800) 5'mols of ethylene oxide Sodium tripolyl0 l0 l0 l0 l0 phosphate 7 Sodium meta- 5 5 5 5 5 5 5 5 phosphate Potassium 2 2 2
  • Liquid aqueous cleansing agent concentrates on the basis of non-ionic, surface-active compounds, having a content of compounds of the general formula of the usual auxiliaries,

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  • 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)
  • Cosmetics (AREA)

Abstract

in which R1 is an aliphatic radical having 4 to 16 carbon atoms, R2 is an aliphatic radical having 1 to 4 carbon atoms and Y is hydrogen or an alkaline metal ion.

Liquid aqueous cleansing agent concentrates on the basis of nonionic surface active compounds, having a content of phosphinic acids or alkaline metal salts thereof of the general formula I

Description

United States Patent Kleiner et al. 1 1 Dec. 2, 1975 15 LIQUID CLEANSING AGENT 3.294.693 l2/l966 Dubre ct al.... 252/010. 17 CONCENTRATES 3.579.576 5/1971 Angstadt 260/502.4 x
[75] Inventors: Hans-Jerg Kleiner, Bad Soden; Otto Keller; Karhfleinz Schneider, both Primary Exammer-W1ll1am E. Schulz of Kelkheim; Gerhart Schneider Attorney, Agent, or Firm-Connolly and Hutz Schneidhain, all of Germany [73] Assignee: Hoechst Aktiengesellschaft, [.57] ABSTRACT Frankfurt am Main, Germany Liquid aqueous cleansing agent concentrates on the l l Flledl 1974 basis of non-ionic surface active compounds, having a [211 App]: NO: 519 247 content of phosphinic acids or alkaline metal salts thereof of the general formula I [30] Foreign Application Priority Data Oct. 30, 1973 Germany 2354223 0 V R i ov [52] US. Cl 252/89; 252/135; 260/502.4 R [51] Int. Cl. CllD l/00 [58] Field of Search 252/89, DIG. 17; 260 02.4 R
[5 in which R is an aliphatic radical having 4 to 16 car- [56] References Cited bon atoms, R is an aliphatic radical having 1 to 4 car- UNITED STATES PATENTS bon atoms and Y is hydrogen or an alkaline-metal ion.
2,724,718 11/1955 Stiles et a1 260/502.4 R 3 Claims, N0 Drawings To prepare liquid concentrates of washing and cleansing agents having a high content of electrolytes on the basis'of non-ionic, surface-active compounds,"
the simultaneous use of so-called hydrotropic sub-" stances or solubilizers is necessary. By-their solu'bilizing capicity it is possible to divide homogeneouslynonionic tensides in salt-containingsolutions and to impart to the cleansing agent concentrates a sufficient stability.
Whereas the sulfonates frequently used for this purpose as hydrotropic substances, as for example toluene sulfonate, xylene sulfonate and cumol sulfonate, generally complywith the requirements in the case'of detergent concentrates on the basis of anion-active detergents, they are ineffective when using non-ionic, surface-active products. However, due to the smaller foaming capacity and the better wetting, emulsifying and cleansing properties, cleansing agents on the basis of non-ionic surface-active compounds are preferred in practice with regard to those basing on anion-active compounds. Therefore, there is a need for hydrotropic solubilizers, which are suitable for such cleansing agent concentrates on the basis of non-ionic tensides.
It is known that solutions containing electrolytes, of
addition of determined phosphoric acid esters, such as for example phosphoric acid monoor diesters of the alkylaryl-polyglycol ethers or of the alkyl-polyglycol ethers. However, the hydrotropic properties of these phosphoric acid esters are only slightly marked, and their effectis not sufficient to dissolve until clear or to disperse the amounts of non-ionic, surface-active com pounds required for the preparation of cleansing agent concentrates, in the presence of high electrolyte concentrations. Thus, for example, in order to maintain in solution about 3 parts of a reaction product of 1 mol of nonyl phenol and mols of ethylene oxide in 100 parts of an aqueous composition corresponding to a usual liquid cleansing concentrate, and containing about 7 of weight of sodium tripolyphosphate, 2 by weight of trisodium phosphate, 3 by weight of sodium metasilicate and I by weight of potassium hydroxide, there are required about 5 by weight of a phosphoric acid monoor diester of an alkylaryl-polyglycol ether or of a fatty alcohol polyglycol ether. Thus, the amounts of these phosphoric acid esters required for the stabilisation of the non-ionic detergent raw materials in solutions having high concentrations of electrolytes, are considerable and lead to a negative influence onto the properties, as for example the foaming capacity and the defoaming capacity, of the cleansing agents.
It has now been found that phosphinic acids or salts thereof of the general formula I wherein R is a straight-chained or branched alkylor alkenyl radical having 4 to 16 carbon atoms, preferably and Y is hydrogen or the sodium or potassium ion, have excellent hydrotropic properties superior to the phosphoric acid esters mentioned, with regard to non-ionic, surface-active compounds, and are therefore, especially suitable for the preparationof liquid aqueous cleansing agent concentrates on th e'basis-of non ionic, surface-active compounds.
The invention further relates to liquid aqueous cleansing agent concentrates on the basis of non-ionic, surface-active compounds,characterized by a content of phosphinic acid derivatives of the general formula I sceletton substances, as they are described for example in the standard work Schwartz, Perry, Berch ;Surface Active Agents and Detergents/volume ll, (l958),
pages 288 to 317. The proportion of, these sceletton substances in the aqueous cleansing agent concentrates is generally up to 35 by weight, especially 5 to 30 by weight. Such sceletton substances are above all alkaliorthoand -polyphosphates, as for example sodium tripolyphosphate or potassium pyrophosphate, in amounts of up to about 20 by weight, preferably 8 to 15 by weight, or organic complexformingagents, as for example ethylene-diamine-tetra-acetate, trisodium citrate or the sodium of the nitrilo-triacetic acid, also in amounts of up to about 20 by weight, especially up to about 12 by weight, and alkali silicates, as for example sodium meta-silicate or sodium-di orftrisilicate, in amounts of up to about 10 by weight, especially up to about 8% by weight.
The aqueous cleansing agent concentrates of the invention may furthermore contain alkali liquors in amounts of up to about 5 by weight, preferably up to 3 by weight, as well as, if required, further usual auxiliaries.
The content of the aqueous cleansing agent concentrates according to the invention of non-ionic detergent raw materials is generally at about 1 to 10 by weight, preferably 2 to 5 by weight, and the content thereof of the phosphinic acid derivatives of the formula I is at about 1 to 5 by weight, preferably L5 to 3.0 %by weight. The content of water of the concentrates is mostly adjusted to about 65 by weight and the pH-value is adjusted to the range of from 8 to 14.
Non-ionic surface-active products, as they may be contained in the liquid cleansing agent concentrates according to the invention, are described for example in the standard work Schwartz, Perry, Berch Surface Active Agents and Detergents, Volume ll, (1958), pages I20 to I38. Preferred non-ionic detergent raw materials are for example:
a. Alkylphenol oxethylates, especially those having 8 to 12 carbon atoms in the alkyl radical and a content of about 4 to 15 oxethylene units,
b. straight-chained or branched, primary or secundary aklylpolyglycol ethers, especially those the alkyl radicals of which comprise about 8 to 20 carbonatoms and which contain .about4 to 20 oxethylene units and, if desired, furthermore a-b out 2 to 20 oxypropylene units in the molecule,.
4 radical R represents methyl. Also preferred are compounds of the formula I, the alkyl radicals of which contain, on the whole, at least 7 carbon atoms.
The following Table lists some Examples of liquid 0. Propylene-oxide ethylene voxide block polymers, cleansing agent concentrates according to the invenespecially the addition compounds of about 5 to 20 tion and determines the stability of the liquid concenmols of ethylene oxide on 1. mol of propylenetrates after standing for 24 hours at 20C according to glycol having a molecular weight of about 1800 to the following scale:
3QO0, 1 Clear stable solution d. Alkylamine-oxyethylates,.especially those having 1O Turbid solutioninclining to the separation of the alkyl radicals of about to 20 carbon atoms and layers. about 4 to oxethylene units in the molecule as The Examples 1 to 15 correspond to the present inwell as vention, the Examples 16 to 45 are comparative prode. Fatty acids oxethylates, especially those with alkyl ucts according to the state of the art. The composition radicals having about 8 to carbon atoms and 15 ofthe cleansing agent concentrates in this Table is indiabout 4 to 15 oxethylene units in the molecule. cated ineach case in percent.
The phosphinic acid derivatives of the formula I used The compositions indicated in the Examples may be in the invention as a constituent of the liquid cleansing used for example as liquid alkaline washing detergents agent concentrates have not only the excellent hydrofor dish washers. Especially interesting is, however, tropic properties but also, surprisingly, a good stability 20 their use as cleansers for industrial purposes in hightowards alkali liquors. They are normally soluble until pressure and vapor stream cleansing apparatures. clear in a concentration of, for example, 10 g/l in a Great value is set on the small foaming effect and a high sodium hydroxide solution at room temperature. cleansing and decreasing capacity. For this reason the Especially interesting from the technical point of slightly foaming, non-ionic surface-active compounds view is above all their capacity of imparting to non- 25 are .preferred for this application; they meet the reionic, surface-active products a sufficient'stability in quirements when used together with the phosphates, salt-containing solutions. silicates and alkalies and the phosphinic acids accord- Compounds of the formula 1 preferably used according to the invention. The compositions indicated in the ing to the invention are those, in which the radical R Table as Examples may, of. course, be varied to a large represents and alkyl radical containing 6 to 10 carbon extent as to their constituents and the corresponding atoms, especially the octyl radical, and wherein the application.
Examples of cleansing agent concentrates Components l 2v 3, 4 5 6 7 8 9 10 ll I2 13 I4 15 Methyloctyl- 2,5 2,5 2 2 2 2 2 2 2 2 2 2 2 2 2 phosphinic acid Phosphoric acidmono-l-diester of lauryl alcohol ethylene oxide Phosphoric acidmono-l-diester of nonyl phenol 4 mols of ethylene oxide Nonyl phenol i 3 3 3 l0 mols ethylene oxide (C J-fatty- 3 3 3 alcohol 9 mols of ethylene oxide Octadecenyl amine 3 3 3 ethylene oxide 'Oleic'acid 6 mols 3 3 3 of ethylene oxide I Polypropylene- 3 3 3 glycol (MG l800) 5'mols of ethylene oxide Sodium tripolyl0 l0 l0 l0 l0 phosphate 7 Sodium meta- 5 5 5 5 -5 silicate Trisodium 5 5 5 5 5 phosphate Potassium 2 2 2 2 2 hydroxide Sodium citrate 20 20 20 20 20 Sodium salt of the 20 20 20 20 20 ethylene-diaminotetra-acetic acid Water 72,5 72,5 73 .73 73 Estimation of i U I I I the concentrates i -continued 7 Components l6 l7 l8 i 19 i 20 2| .22 23 24 t 25 ,26 27' 28 29 30. Methyloctyla v i, i i, phosphinic acid I i t. t I Phosphoric acid- 5 5 5 2 2 2 2 2 2 2 2 mono'l-diester of lauryl alcohol 4 mols of ethylene oxide Phosphoric acidmono-l-diester of nonyl phenol 4 mols of ethylene oxide Nonyl phenol 3 V 3 3 l0 mols ethylene oxide mi i I i v t r alcohol 9 mols of ethylene oxide it Octadecenyl amine V 3 3 3 8 mols of ethylene-oxide i k v Oleic acid l- 6 mols 3 3 l i 3 of ethylene oxide i Polypropylene- 3 3 3 glycol (MG 1800) 5 mols of ethylene oxide Sodium tripolyl0 l0 l0 l0 l0 phosphate Sodium meta- 5 5 5 5 5 silicate Trisodium 5 5 5 5 5 phosphate Potassium 2 2 2 2 2 hydroxide Sodium citrate 20 20 20 20 Sodium salt of the 20 20 20 20 20 ethylene-diaminotetra-acetic acid Water 70 70 7O 70 7O 75 75 75 75 75 75 75 75 75 75 Estimation of the concentrates Components 3! 32 33 34 35 36 37 38 39 4O 41 42 43 44 45 Methyloctylphosphinic acid Phosphoric acidmono-l-diester of lauryl alcohol 4 mols of ethylene oxide Phosphoric acidmono-l-diester of nonyl phenol 4 m'ols of ethylene oxide Nonyl phenol 3 3 3 l0 mols of ethylene oxide (C )-fatty- 3 3 3 alcohol 9 mols of ethylene oxide Octadecenyl amine 3 3 3 8 mols of ethylene oxide Oleic acid 6 mols 3 3 3 of ethylene oxide Polypropylene- 3 3 3 glycol (MG 1800) 5 mols of ethylene oxide Sodium tripoly- I0 l0 l0 l0 l0 phosphate Sodium meta- 5 5 5 5 5 silicate Trisodium 5 5 5 5 5 phosphate Potassium 2 2 2 2 2 hydroxide 20 2O 20 20 20 Sodium citrate 20 2Q 20 20 20 Sodium salt of the -continued I Components BI 32 33 34 35 36 37 38 39 40 4| 42 43 44 45 ethylene-diaminotetraacetic acid Water 70 7O 70 7O 7O 75 75 75 75 75 75 75 75 75 75 Estimation of the concentrates What we claim is:
1. Liquid aqueous cleansing agent concentrates on the basis of non-ionic, surface-active compounds, having a content of compounds of the general formula of the usual auxiliaries,

Claims (3)

1. LIQUID AQUEOUS CLEANSING AGENT CONCENTRATES ON THE BASIS OF NON-IONIC, SURFACE-ACTIVE COMPOUNDS, HAVING A CONTENT OF COMPOUNDS OF THE GENERAL FORMULA
2. Liquid aqueous cleansing agent concentrates as claimed in claim 1 wherein R2 represents methyl.
3. Liquid cleansing agent concentrates as claimed in claim 1 which contain about 1 to 10 percent by weight of the usual auxiliaries,
US519247A 1973-10-30 1974-10-30 Liquid cleansing agent concentrates Expired - Lifetime US3923678A (en)

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FR (1) FR2249163B1 (en)
GB (1) GB1462239A (en)
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NL (1) NL7413990A (en)

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4257908A (en) * 1975-08-11 1981-03-24 Colgate Palmolive Company Laundry detergent in gel form
US4528110A (en) * 1982-11-04 1985-07-09 Henkel Kommanditgesellschaft Auf Aktien Method of using alkyl monophosphoric acids as germicidal agents
US4606842A (en) * 1982-03-05 1986-08-19 Drackett Company Cleaning composition for glass and similar hard surfaces
US4793942A (en) * 1987-01-08 1988-12-27 Ecolab Inc. Detersive systems with a dispersed aqueous-organic softening agent for hardness removal
US4911856A (en) * 1988-11-30 1990-03-27 Ecolab Inc. Low acid, soluble salt containing aqueous-organic softening agents for detersive systems
US4971714A (en) * 1988-11-30 1990-11-20 Ecolab Inc. Detersive system with an improved hardness ion complexing agent
US5900455A (en) * 1992-06-05 1999-05-04 Shell Oil Company Elastosols, process for the preparation thereof, process for the use of such elastosols and products derived from them
US20020164426A1 (en) * 1999-09-23 2002-11-07 Ennis Thomas James Method of adhering coatings to substrates
US20050233937A1 (en) * 2004-04-08 2005-10-20 Akzo Nobel N.V. Detergent composition
US11124628B2 (en) 2016-08-30 2021-09-21 Dow Global Technologies Llc Method of attenuating concerntration of acrolein

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4230592A (en) * 1979-05-31 1980-10-28 Chemed Corporation Controlled foam detergent additive
JPS58128311A (en) * 1982-01-28 1983-07-30 Pola Chem Ind Inc Solubilizer resistant to temperature change and solubilization
GB9000704D0 (en) * 1990-01-12 1990-03-14 Unilever Plc Topical composition

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2724718A (en) * 1948-04-12 1955-11-22 Shell Dev Preparation of phosphorus-containing organic compounds
US3294693A (en) * 1962-05-18 1966-12-27 Rohm & Haas Phosphorylated surfactants as hydrotropes
US3579576A (en) * 1964-02-25 1971-05-18 Sun Oil Co Organophosphorus compounds and a process for the making thereof

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2724718A (en) * 1948-04-12 1955-11-22 Shell Dev Preparation of phosphorus-containing organic compounds
US3294693A (en) * 1962-05-18 1966-12-27 Rohm & Haas Phosphorylated surfactants as hydrotropes
US3579576A (en) * 1964-02-25 1971-05-18 Sun Oil Co Organophosphorus compounds and a process for the making thereof

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4257908A (en) * 1975-08-11 1981-03-24 Colgate Palmolive Company Laundry detergent in gel form
US4606842A (en) * 1982-03-05 1986-08-19 Drackett Company Cleaning composition for glass and similar hard surfaces
US4528110A (en) * 1982-11-04 1985-07-09 Henkel Kommanditgesellschaft Auf Aktien Method of using alkyl monophosphoric acids as germicidal agents
US4793942A (en) * 1987-01-08 1988-12-27 Ecolab Inc. Detersive systems with a dispersed aqueous-organic softening agent for hardness removal
US4911856A (en) * 1988-11-30 1990-03-27 Ecolab Inc. Low acid, soluble salt containing aqueous-organic softening agents for detersive systems
US4971714A (en) * 1988-11-30 1990-11-20 Ecolab Inc. Detersive system with an improved hardness ion complexing agent
US5900455A (en) * 1992-06-05 1999-05-04 Shell Oil Company Elastosols, process for the preparation thereof, process for the use of such elastosols and products derived from them
US20020164426A1 (en) * 1999-09-23 2002-11-07 Ennis Thomas James Method of adhering coatings to substrates
US20050233937A1 (en) * 2004-04-08 2005-10-20 Akzo Nobel N.V. Detergent composition
US11124628B2 (en) 2016-08-30 2021-09-21 Dow Global Technologies Llc Method of attenuating concerntration of acrolein

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FR2249163B1 (en) 1978-11-24
BE821689A (en) 1975-04-30
AT337327B (en) 1977-06-27
IT1025269B (en) 1978-08-10
FR2249163A1 (en) 1975-05-23
ATA862474A (en) 1976-10-15
JPS5078608A (en) 1975-06-26
DE2354223A1 (en) 1975-05-28
NL7413990A (en) 1975-05-02

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