WO1990006355A1 - Aqueous caustic cleaning solutions - Google Patents

Aqueous caustic cleaning solutions Download PDF

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Publication number
WO1990006355A1
WO1990006355A1 PCT/US1989/005299 US8905299W WO9006355A1 WO 1990006355 A1 WO1990006355 A1 WO 1990006355A1 US 8905299 W US8905299 W US 8905299W WO 9006355 A1 WO9006355 A1 WO 9006355A1
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Prior art keywords
aqueous cleaning
cleaning solution
alkali metal
hydroxide
alkyl group
Prior art date
Application number
PCT/US1989/005299
Other languages
French (fr)
Inventor
Michael Scardera
Frank R. Grosser
Original Assignee
Olin Corporation
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Olin Corporation filed Critical Olin Corporation
Publication of WO1990006355A1 publication Critical patent/WO1990006355A1/en

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Classifications

    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D7/00Compositions of detergents based essentially on non-surface-active compounds
    • C11D7/02Inorganic compounds
    • C11D7/04Water-soluble compounds
    • C11D7/06Hydroxides
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/38Cationic compounds
    • C11D1/42Amino alcohols or amino ethers
    • C11D1/44Ethers of polyoxyalkylenes with amino alcohols; Condensation products of epoxyalkanes with amines
    • CCHEMISTRY; METALLURGY
    • C23COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
    • C23GCLEANING OR DE-GREASING OF METALLIC MATERIAL BY CHEMICAL METHODS OTHER THAN ELECTROLYSIS
    • C23G1/00Cleaning or pickling metallic material with solutions or molten salts
    • C23G1/14Cleaning or pickling metallic material with solutions or molten salts with alkaline solutions

Definitions

  • the present invention relates to aqueous cleaning solutions containing selected nonionic surfactants and alkali metal hydroxides.
  • solutions of alkali metal hydroxides i.e. caustic solutions
  • sodium hydroxide or potassium hydroxide are used in a wide variety of applications in which an improvement in the wetting properties is a distinct advantage, particularly for solutions having high
  • concentrations of the alkali metal hydroxide are employed in the metal cleaning business to remove greases and process fluids from metal finishes. They are used in the textile field to remove knitting oils and the like from textiles. They are also used in emulsion
  • polymerization reactions to aid the dispersion of one or more of the reactants in each other or in a solvent. Further, they are employed in dairy/food plants and in bottle washing operations, as well as in household and other consumer cleaners.
  • a surfactant is added to the solution.
  • Surfactants such as ethoxylated alcohols, phosphate esters, alkyl aryl sulfonates, etc. exhibit solubility in caustic solutions containing 0-5% by weight of the alkali metal hydroxide. This limited solubility
  • alkylated diphenyl oxide disulfonates e.g. DOWFAX (R) 2Al made by Dow
  • This anionic surfactant is a high foaming surfactant soluble in 20% caustic.
  • alkylated glucosides e.g. TRITON (R) BG-10 made by Rohm & Haas Co. of Philadelphia, PA.
  • This nonionic surfactant is soluble in 50% caustic but its wetting efficiency drops significantly when the caustic solution is diluted as exhibited by surface tension measurements.
  • alkylphenol - glycidol adducts e.g.
  • Surfactant 10G made by Olin Corp. of Stamford, CT).
  • This nonionic surfactant is soluble in 50% caustic but has limited biodegradability.
  • R represents an alkyl group having from about
  • Y represents H, (CH 2 --CH--CH 2 O) m H, or R', and mixtures thereof,
  • R' represents an alkyl group, the sum total of carbon atoms in R + R' being from about 8 to about 18;
  • n is from about 1 to about 20; and m + n are from about 2 to about 20.
  • aqueous cleaning solutions of the present invention have as one component an alkali metal
  • alkali metal hydroxides include for example, sodium hydroxide, potassium hydroxide, lithium hydroxide, and mixtures thereof.
  • aqueous cleaning solutions may contain any desired concentration of the alkali metal hydroxide, those for which there is a commercial need are aqueous solutions which initially contain at least about 5% by weight of the alkali metal hydroxide.
  • Preferred aqueous cleaning solutions contain from about 10 to about 60% by weight of the alkali metal hydroxide, with more preferred aqueous cleaning solutions
  • alkali metal hydroxide containing from about 20 to about 50% by weight of alkali metal hydroxide.
  • Sodium hydroxide, potassium hydroxide or mixtures thereof, are preferred as alkali metal hydroxides, with sodium hydroxide being more preferred.
  • the aqueous cleaning solutions of the present invention include a wetting amount of the nonionic surfactant represented by Formula I which is comprised of a primary or secondary alkyl amine group and any suitable number of glycidol groups.
  • Suitable alkyl amines include homogeneous amine groups as well as mixtures such as those sold commercially as coco amines, soya amines, and tallow amines or mixed fatty amines.
  • alkyl groups may be branched or linear, where improved biodegradability is desired, linear alkyl groups with minimal branching are preferred.
  • Amine glycidol adducts represented include those of Formula I in which R represents, for example, octyl, nonyl, decyl, hendecyl, dodecyl or coco or lauryl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl or stearyl (tallow or soya), and mixtures thereof.
  • Y represents H, (CH 2 --CH--CH 2 O) m H' or mixtures thereof; are generally a mixture in which Y represents both H and the glycidol group and the amine is therefore a mixture of secondary and tertiary amines.
  • the amine glycidol adducts include those, for example, in which R
  • R' represents for example, methyl, ethyl, butyl, hexyl, or octyl, and preferably an alkyl group having from 1 to about 4 carbon atoms.
  • More preferred embodiments of the amine glycidol adducts include those in which R represents an alkyl group having from about 12 to about 16 carbon atoms and mixtures thereof; and m + n are from about 2 to about 10. It should be noted that the m and n represent an average number of glycidol units per alkyl amine unit.
  • Adducts of amines with glycidol having surface-active properties have been prepared by L.
  • glycidol adducts used in the novel aqueous cleaning solutions of the present invention are those which are normally used to provide the desired wetting
  • wetting amounts include at least 0.1 percent by weight of the nonionic amine glycidol adducts.
  • aqueous cleaning solutions of the present invention may contain added components such as a chelating or sequestering agent, a builder, a corrosion inhibitor, etc.
  • a chelating or sequestering agent such as sodium, sodium, sodium, sodium, sodium, sodium, sodium, sodium, sodium, sodium, sodium, sodium, sodium, sodium, sodium, sodium, sodium, sodium, sodium, sodium, sodium, sodium, sodium, sodium, sodium, sodium, sodium, sodium, sodium, sodium, sodium, sodium, sodium, sodium, sodium,
  • potassium, ammonium or calcium salts of these acids are useful in the practice of our invention.
  • Typical of these materials are, for example,
  • ethylenediamine tetraacetic acid nitrilo triacetic acid, gluconic acid, diethylenetriamine pentaacetic acid.
  • chelating or sequestering agents are hydroxyalkylidene diphosphonic acids such as
  • Suitable builders include alkali
  • metasilicates such as sodium metasilicates, alkali metal phosphates including, for example, sodium
  • tripolyphosphate and potassium pyrophosphate as well as alkali metal citrates and alkali metal sesquicarbonates.
  • novel aqueous cleaning solutions are used in metal cleaning, it may be desirable to include a corrosion inhibitor such as an alkali metal silicate or an organic compound including triazole compounds such as a benzotriazole or toluotriazole.
  • a corrosion inhibitor such as an alkali metal silicate or an organic compound including triazole compounds such as a benzotriazole or toluotriazole.
  • novel aqueous cleaning solutions of the present invention may be used in various applications including, for example, the removal of polymer residues from equipment surfaces as described in U.S. Patent No. 3,865,628, issued to J. W. Callahan et al; low
  • reaction mixture was heated at the reaction temperature for an additional 2 hours. After cooling, 31.6 g of the liquid product was recovered and determined to be a 3-mole glycidol adduct of the aliphatic amine. To an aqueous solution of sodium hydroxide (50 percent by weight of NaOH) was added 1 percent by weight of the product which dissolved to form a clear solution.
  • sodium hydroxide 50 percent by weight of NaOH
  • Example 1 The process of Example 1 was repeated exactly using varying rations of glycidol to the blend of aliphatic amines (ARMEEN (R) CD). Reactant amounts and reaction conditions are given in Table I below.
  • Example 8 The process of Example 1 was employed to react dodecylamine with glycidol in ratios of 1:3 and 1:4 respectively. The results are given in Table 1 below.
  • Example 8 The process of Example 1 was employed to react dodecylamine with glycidol in ratios of 1:3 and 1:4 respectively. The results are given in Table 1 below.
  • Example 9 The process of Example 1 was repeated exactly to react decylamine with glycidol in a ratio of 1:3. The results are given in Table I below. Example 9
  • Example 10 Substituting tetradecylamine for the blend of aliphatic amines, the process of Example 1 was employed using an amine to glycidol ratio of 1:4. The results are given in Table 1 below.
  • Example 10
  • Example 1 The process of Example 1 was employed to react an aliphatic (C 16 and C 18 ) amine blend
  • Cloud Point is an indication of solubility.

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Wood Science & Technology (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Inorganic Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Materials Engineering (AREA)
  • Mechanical Engineering (AREA)
  • Metallurgy (AREA)
  • Detergent Compositions (AREA)
  • Cleaning And De-Greasing Of Metallic Materials By Chemical Methods (AREA)

Abstract

An aqueous cleaning solution having good wetting properties in high caustic concentrations, improved the biodegradability, and low to moderate foaming is comprised of an alkali metal hydroxide and a wetting amount of a nonionic surfactant represented by formula (I), wherein R represents an alkyl group having from about 8 to about 18 carbon atoms and mixtures thereof, Y represents H, α, or R', and mixtures thereof, R' represents an alkyl group, the sum total of carbon atoms in R + R' being from about 8 to about 18; n is from about 1 to about 20; and m + n are from about 2 to about 20.

Description

AQUEOUS CAUSTIC CLEANING SOLUTIONS
The present invention relates to aqueous cleaning solutions containing selected nonionic surfactants and alkali metal hydroxides.
Solutions of alkali metal hydroxides (i.e. caustic solutions) such as sodium hydroxide or potassium hydroxide, are used in a wide variety of applications in which an improvement in the wetting properties is a distinct advantage, particularly for solutions having high
concentrations of the alkali metal hydroxide. For example, they are employed in the metal cleaning business to remove greases and process fluids from metal finishes. They are used in the textile field to remove knitting oils and the like from textiles. They are also used in emulsion
polymerization reactions to aid the dispersion of one or more of the reactants in each other or in a solvent. Further, they are employed in dairy/food plants and in bottle washing operations, as well as in household and other consumer cleaners.
To provide the desired improvement in wetting properties a surfactant is added to the solution.
However, commonly used surfactants have limited
solubility or stability in caustic solutions.
Surfactants, such as ethoxylated alcohols, phosphate esters, alkyl aryl sulfonates, etc. exhibit solubility in caustic solutions containing 0-5% by weight of the alkali metal hydroxide. This limited solubility
prevents their use in application requiring a higher concentration of caustic or the formulation of a concentrate employing a high percentage of caustic which is diluted for use.
Surfactants which are commonly used in solutions having higher concentrations of caustic (i.e. 10% by weight or higher) are: (1) alkylated diphenyl oxide disulfonates (e.g. DOWFAX(R) 2Al made by Dow
Chemical Co. of Midland, MI). This anionic surfactant is a high foaming surfactant soluble in 20% caustic.
(2) alkylated glucosides (e.g. TRITON(R) BG-10 made by Rohm & Haas Co. of Philadelphia, PA).
This nonionic surfactant is soluble in 50% caustic but its wetting efficiency drops significantly when the caustic solution is diluted as exhibited by surface tension measurements.
(3) alkylphenol - glycidol adducts (e.g.
Surfactant 10G made by Olin Corp. of Stamford, CT).
This nonionic surfactant is soluble in 50% caustic but has limited biodegradability.
Thus, there is a need for aqueous cleaning solutions containing alkali metal hydroxides and a surfactant having, in addition to good wetting
properties in high caustic concentrations, improved biodegradability, low to moderate foaming, and which maintain their surface activity when diluted. These advantages are accomplished in an aqueous cleaning solution characterized by an alkali metal hydroxide and a wetting amount of a nonionic surfactant represented by the formula:
Y OH
R--N--(CH2--CH--CH2O)nH wherein R represents an alkyl group having from about
8 to about 18 carbon atoms and mixtures thereof,
OH
Y represents H, (CH2--CH--CH2O)mH, or R', and mixtures thereof,
R' represents an alkyl group, the sum total of carbon atoms in R + R' being from about 8 to about 18;
n is from about 1 to about 20; and m + n are from about 2 to about 20.
The aqueous cleaning solutions of the present invention have as one component an alkali metal
hydroxide. Suitable alkali metal hydroxides include for example, sodium hydroxide, potassium hydroxide, lithium hydroxide, and mixtures thereof.
While the aqueous cleaning solutions may contain any desired concentration of the alkali metal hydroxide, those for which there is a commercial need are aqueous solutions which initially contain at least about 5% by weight of the alkali metal hydroxide.
Preferred aqueous cleaning solutions contain from about 10 to about 60% by weight of the alkali metal hydroxide, with more preferred aqueous cleaning solutions
containing from about 20 to about 50% by weight of alkali metal hydroxide. Sodium hydroxide, potassium hydroxide or mixtures thereof, are preferred as alkali metal hydroxides, with sodium hydroxide being more preferred.
The aqueous cleaning solutions of the present invention include a wetting amount of the nonionic surfactant represented by Formula I which is comprised of a primary or secondary alkyl amine group and any suitable number of glycidol groups. Suitable alkyl amines include homogeneous amine groups as well as mixtures such as those sold commercially as coco amines, soya amines, and tallow amines or mixed fatty amines.
While the alkyl groups may be branched or linear, where improved biodegradability is desired, linear alkyl groups with minimal branching are preferred.
Amine glycidol adducts represented include those of Formula I in which R represents, for example, octyl, nonyl, decyl, hendecyl, dodecyl or coco or lauryl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl or stearyl (tallow or soya), and mixtures thereof.
Embodiments of the nonionic alkyl amine glycidol surfactant in which
OH
Y represents H, (CH2--CH--CH2O)mH' or mixtures thereof; are generally a mixture in which Y represents both H and the glycidol group and the amine is therefore a mixture of secondary and tertiary amines.
Where Y represents R', the amine glycidol adducts include those, for example, in which R
represents butyl, hexyl, octyl, nonyl, decyl or coco, hendecyl, dodecyl or lauryl or coco, tetradecyl, pentadecyl, hexadecyl, or heptadecyl, and R' represents for example, methyl, ethyl, butyl, hexyl, or octyl, and preferably an alkyl group having from 1 to about 4 carbon atoms.
More preferred embodiments of the amine glycidol adducts include those in which R represents an alkyl group having from about 12 to about 16 carbon atoms and mixtures thereof; and m + n are from about 2 to about 10. It should be noted that the m and n represent an average number of glycidol units per alkyl amine unit.
Adducts of amines with glycidol having surface-active properties have been prepared by L.
Orthner et al (U.S. Patent Nos. 2,089,569 and 2,131,142) E. Ulsperger et al J. Pratt Chem. 27 (3-4) 195-212
(1965); Chem. Abstract 62, 11675a (1965); and W.
Willmund et al Germ. Offenleg. 2,644,289, published April 6, 1978. These prior art references however, give no indication that these compositions are soluble in alkalies such as caustic soda or caustic potash. Wetting amounts of the nonionic amine
glycidol adducts used in the novel aqueous cleaning solutions of the present invention are those which are normally used to provide the desired wetting
properties. For example, wetting amounts include at least 0.1 percent by weight of the nonionic amine glycidol adducts.
The aqueous cleaning solutions of the present invention, depending on the application, may contain added components such as a chelating or sequestering agent, a builder, a corrosion inhibitor, etc. For example, any of the usual chelants such as the polyamino carboxylic acid products, including the sodium,
potassium, ammonium or calcium salts of these acids, for example, are useful in the practice of our invention. Typical of these materials are, for example,
ethylenediamine tetraacetic acid, nitrilo triacetic acid, gluconic acid, diethylenetriamine pentaacetic acid. Also suitable as chelating or sequestering agents are hydroxyalkylidene diphosphonic acids such as
hydroxyethylidene diphosphonic acid.
Suitable builders include alkali
metasilicates such as sodium metasilicates, alkali metal phosphates including, for example, sodium
tripolyphosphate and potassium pyrophosphate, as well as alkali metal citrates and alkali metal sesquicarbonates.
Where the novel aqueous cleaning solutions are used in metal cleaning, it may be desirable to include a corrosion inhibitor such as an alkali metal silicate or an organic compound including triazole compounds such as a benzotriazole or toluotriazole.
The novel aqueous cleaning solutions of the present invention may be used in various applications including, for example, the removal of polymer residues from equipment surfaces as described in U.S. Patent No. 3,865,628, issued to J. W. Callahan et al; low
temperature metal cleaning as taught in U.S. Patent No. 4,048,121, by E. H. Chang; caustic soda concentrates similar to those taught in U.S. Patent No. 3,437,598, by J. J. De Valdre et al; as well as a replacement for bottle washing solutions employed commercially.
To further illustrate the invention the following examples are provided without any intention of being limited thereby. All parts and percentages are by weight unless otherwise specified.
Example 1
Under a nitrogen atmosphere, a blend of aliphatic (C8 - C18) amines (ARMEEN(R) CD,
produced by Armak Chemicals), (15 g , 0.075 m) was added to a reaction vessel and heated to 138°C. To the hot amine 16.67 g (0.225 m) of glycidol were added at a rate of about 0.15 g per minute. During the glycidol
addition period the reaction temperature was maintained at 140-152°C. After the glycidol addition the
reaction mixture was heated at the reaction temperature for an additional 2 hours. After cooling, 31.6 g of the liquid product was recovered and determined to be a 3-mole glycidol adduct of the aliphatic amine. To an aqueous solution of sodium hydroxide (50 percent by weight of NaOH) was added 1 percent by weight of the product which dissolved to form a clear solution.
Examples 2, 3, 4, and 5
The process of Example 1 was repeated exactly using varying rations of glycidol to the blend of aliphatic amines (ARMEEN (R) CD). Reactant amounts and reaction conditions are given in Table I below.
Examples 6 and 7
The process of Example 1 was employed to react dodecylamine with glycidol in ratios of 1:3 and 1:4 respectively. The results are given in Table 1 below. Example 8
The process of Example 1 was repeated exactly to react decylamine with glycidol in a ratio of 1:3. The results are given in Table I below. Example 9
Substituting tetradecylamine for the blend of aliphatic amines, the process of Example 1 was employed using an amine to glycidol ratio of 1:4. The results are given in Table 1 below. Example 10
The process of Example 1 was employed to react an aliphatic (C16 and C18) amine blend
(ARMEEN(R ) 16D) with glycidol in a ratio of 1:8. The results are given in Table 1 below. Example 11
An aliphatic (C14 to C18) amine blend
(ARMEEN(R) T) was substituted for the aliphatic amine blend in the process of Example 1. The results are given in Table 1 below.
Figure imgf000012_0001
Examples 12-22
The "cloud point" for each of the amine glycidol adducts prepared in Examples 1-11 was
determined in distilled water and in an aqueous solution of sodium hydroxide (10 percent NaOH).
"Cloud Point" is an indication of solubility. A 1 percent aqueous solution of the
surfactant is heated until a point is reached where the surfactant begins to separate out, causing the solution to become turbid or cloudy. This is called the "Cloud Point".
In addition, the solubility of the amine glycidol adducts produced in Examples 1-11 in a
concentrated aqueous solution of sodium hydroxide was determined. In each Example a single phase clear solution was obtained. The cloud points and solubility data are given in Table II below.
I
Figure imgf000014_0001

Claims

WHAT IS CLAIMED:
1. An aqueous cleaning solution characterized by an alkali metal hydroxide and a wetting amount of a nonionic surfactant
represented by the formula:
Figure imgf000015_0001
Figure imgf000015_0002
R--NN-- (CH2--CH--CH2O)nH wherein R represents an alkyl group having from about 8 to about 18 carbon atoms and mixtures thereof,
Figure imgf000015_0003
Y represents H, (CH 2--CH-- CH2O)mH, or
R', and mixtures thereof, R' represents an alkyl group, the sum total of carbon atoms in R + R' being from about 8 to about 18;
n is from about 1 to about 20; and m + n are from about 2 to about 20
2. The aqueous cleaning solution of claim 1 characterized in that the alkali metal hydroxide is selected from the group consisting of sodium hydroxide, potassium hydroxide, and lithium hydroxide.
3. The aqueous cleaning solution of claim 1 characterized in that R represents a linear alkyl group.
4. The aqueous cleaning solution of claim 1 characterized in that the concentration of alkali metal hydroxide is at least 5 percent by weight.
5. The aqueous cleaning solution of claim 1 characterized in that Y represents
Figure imgf000016_0001
and m + n are in the range of from about 3 to about 16.
6. The aqueous cleaning solution of claim 1 characterized in that Y represents R'.
7. The aqueous cleaning solution of claim 6 characterized in that R' represents an alkyl group having from 1 to about 4 carbon atoms.
8. The aqueous cleaning solution of claim 5 characterized in that R represents
decylamine.
9. The aqueous cleaning solution of claim 5 characterized in that R represents
dodecylamine.
10. The aqueous cleaning solution of claim 5 characterized in that R represents
tetradecylamine.
11. The aqueous cleaning solution of claim 5 characterized in that R represents cocoamine.
12. The aqueous cleaning solution of claim 1 characterized in that the alkali metal hydroxide concentration is from about 10 to about 60 percent by weight.
13. The aqueous cleaning solution of claim 12 characterized in that the alkali metal hydroxide is selected from the group consisting of sodium hydroxide and potassium hydroxide.
PCT/US1989/005299 1988-11-25 1989-11-22 Aqueous caustic cleaning solutions WO1990006355A1 (en)

Applications Claiming Priority (2)

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US276,177 1988-11-25

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20130171264A1 (en) * 2010-06-21 2013-07-04 Mtp Innovations Disinfectant Composition
US20220396639A1 (en) * 2021-06-15 2022-12-15 Hyundai Motor Company Method for preparing nanocellulose using nonionic surfactants

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2114839A1 (en) * 1970-04-01 1971-10-14 Unilever Nv Process for cleaning and degreasing metals with liquid cleaning agents
DE2644289A1 (en) * 1976-09-30 1978-04-06 Henkel Kgaa Compsn. for washing solid materials esp. textiles - contains tert. amine surfactant and allows redn. in detergent concn.
US4521332A (en) * 1981-03-23 1985-06-04 Pennwalt Corporation Highly alkaline cleaning dispersion

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2114839A1 (en) * 1970-04-01 1971-10-14 Unilever Nv Process for cleaning and degreasing metals with liquid cleaning agents
DE2644289A1 (en) * 1976-09-30 1978-04-06 Henkel Kgaa Compsn. for washing solid materials esp. textiles - contains tert. amine surfactant and allows redn. in detergent concn.
US4521332A (en) * 1981-03-23 1985-06-04 Pennwalt Corporation Highly alkaline cleaning dispersion

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20130171264A1 (en) * 2010-06-21 2013-07-04 Mtp Innovations Disinfectant Composition
US10827752B2 (en) * 2010-06-21 2020-11-10 Peter Finan Disinfectant composition
US20220396639A1 (en) * 2021-06-15 2022-12-15 Hyundai Motor Company Method for preparing nanocellulose using nonionic surfactants

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