EP4098729A1 - Nichtentflammbare, flüchtige und wässrige reinigungszusammensetzung - Google Patents

Nichtentflammbare, flüchtige und wässrige reinigungszusammensetzung Download PDF

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Publication number
EP4098729A1
EP4098729A1 EP21305734.2A EP21305734A EP4098729A1 EP 4098729 A1 EP4098729 A1 EP 4098729A1 EP 21305734 A EP21305734 A EP 21305734A EP 4098729 A1 EP4098729 A1 EP 4098729A1
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EP
European Patent Office
Prior art keywords
ether
compound
glycol
equal
composition according
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EP21305734.2A
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English (en)
French (fr)
Inventor
Alexandre FINKE
Mikaël PETIT
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Cipelia
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Cipelia
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Priority to EP21305734.2A priority Critical patent/EP4098729A1/de
Priority to PCT/EP2022/064811 priority patent/WO2022253857A1/en
Publication of EP4098729A1 publication Critical patent/EP4098729A1/de
Pending legal-status Critical Current

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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
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/20—Organic compounds containing oxygen
    • C11D3/2068—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
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/20—Organic compounds containing oxygen
    • C11D3/2003—Alcohols; Phenols
    • C11D3/2006—Monohydric alcohols
    • 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
    • C11D3/20—Organic compounds containing oxygen
    • C11D3/2003—Alcohols; Phenols
    • C11D3/2041—Dihydric alcohols
    • 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
    • C11D7/00—Compositions of detergents based essentially on non-surface-active compounds
    • C11D7/22—Organic compounds
    • C11D7/26—Organic compounds containing oxygen
    • C11D7/261—Alcohols; Phenols
    • 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
    • C11D7/00—Compositions of detergents based essentially on non-surface-active compounds
    • C11D7/22—Organic compounds
    • C11D7/26—Organic compounds containing oxygen
    • C11D7/263—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
    • C11D7/00—Compositions of detergents based essentially on non-surface-active compounds
    • C11D7/50—Solvents
    • C11D7/5031—Azeotropic mixtures of non-halogenated solvents

Definitions

  • the present invention concerns a new non-flammable, volatile and aqueous cleaning composition, and its use for example as a degreaser for metal, ceramic or polymer parts in the mechanical, industrial, agricultural or consumer fields.
  • the composition can also be used on glass surfaces (e.g. vehicle windscreens), glass-ceramics.
  • the cleaning of natural or synthetic textiles can also be considered.
  • references in square brackets ([ ]) refer to the list of references at the end of the text.
  • Detergent formulations for glass surfaces are often based on mixtures of water and water-soluble solvents such as monohydroxy alcohols (usually ethyl alcohol, isopropyl alcohol), which are known for their degreasing efficiency.
  • these same solvents ensure rapid drying of surfaces without leaving residues or traces.
  • these same solvents are the main cause of the regulatory classification of these mixtures as flammable due to a flash point less than or equal to 60°C.
  • the storage and transport of these compositions must comply with the drastic directives and regulations in force in order to ensure the safety of goods and people, generating non-negotiable costs.
  • Outdoor storage may then be preferred, as natural ventilation evacuates any vapors and does not allow the lower flammability limits to be reached.
  • Cold winter conditions give rise to other problems such as freezing or phase shifting of the mixtures.
  • compositions based on surfactants has often been the means to achieve ideal stain removal by a separation mechanism, emulsion soluble in the water formed, thus achieving the cleaning and soil removal action.
  • all surfactants do not provide the required properties.
  • the main solution is to use fluids or solvents which are difficult to ignite, might be quite volatile but still have high flash points.
  • Halogenated hydrocarbons such as tetrachloromethane meet these criteria perfectly.
  • Their vapor pressure of more than 10 kPa at 20°C ensures rapid evaporation, while their freezing point of less than -20°C guarantees their use over a wide temperature range.
  • halogenated hydrocarbons such as perfluoroalkyl ethylenes (e.g. in particular perfluorobutyl ethylene), is for example described in Patent EP0443911 [1].
  • CFC-113 The 1,1,2-trichloro-1,2,2-trifluoroethane (CFC-113) has also been widely recognized for its cleaning properties but much research has sought to replace it to reduce environmental impact.
  • glycol ethers are also known for their antifreeze power.
  • the amounts below 10% claimed in many documents (International Application WO2017/011216 , US8,114,223 ) [7,8] are not sufficient to achieve sufficient antifreeze power, based on comparative data with ethylene glycol (10% aqueous solution freezes at -5°C) and on the law of cryometry (the lowering of the solidification temperature is proportional to the molar fraction of the solute).
  • the purpose of the invention is thus to provide a multi-surface cleaning composition having limited manufacturing, transport and storage requirements and respecting the health and safety of the user and the environment, with contradictory properties:
  • composition is biodegradable according to the OECD 302B method.
  • composition does not affect metal surfaces. After 120h contact at 50°C, carbon steel, stainless steel, copper, brass and aluminum samples show a negligible mass change of less than 0.05 mg/cm 2 , and no visual signs of corrosion or staining.
  • the composition does not degrade polymers including elastomers and plastics.
  • NBR, EPDM, PE, PP, PVC, POM, PBT specimens with a mass change of more than 0.4% were tested.
  • the hardnesses of these specimens are also not modified in relation to a reference value (verification carried out on NBR elastomer material in particular) in accordance with the requirements of standards such as JIS K2398-2001 "Automotive windscreen cleaning agent".
  • This standard specifies each technical requirement in more detail: exterior appearance, freezing point, pH value, high temperature stability, low temperature stability, detergency, compatibility with metal(s), rubber(s), plastic(s), coating(s), etc.
  • composition also respects paints and surface coatings. After 24 hours of contact at 50°C, no visual modification (blistering, delamination,%) has been observed on epoxy, urethane or acrylic type paints.
  • the present invention thus concerns a non-flammable, volatile and aqueous composition
  • a non-flammable, volatile and aqueous composition comprising at least one compound A and optionally at least one compound selected from the group consisting of a compound B and a compound C, wherein :
  • the alkyl groups are chosen in the group comprising methyl, ethyl, n-propyl, iso-propyl, n-butyl, tert-butyl and hexyl.
  • the aryl group is phenyl
  • the glycol ether(s) of the compound A are advantageously glycol ethers with a flash point equal or above 30°C, preferably above 60°C (to achieve the non-flammable feature of the end-use product), with a freezing point below -15°C (to guarantee use of the end-use product over a wide temperature range, namely by inhibiting ice formation or remaining its liquid state at temperature in the range from about -15°C to about -30°C), with a vapor pressure greater than 0.05 kPa at 20°C (to achieve quick drying of the end-use product) and/or having a molecular mass less than 150 g/mol (to ensure better stability and prevent freezing of the end-use product), but excluding all compounds categorized for reproductive toxicity according to GHS and CLP Regulation (EC) 1272/2008.
  • EC GHS and CLP Regulation
  • Glycol ethers are amphiphilic solvents that are both soluble in water and fatty substances. This gives them useful properties for many technical and industrial uses, i.e. excellent cleaning and degreasing properties, with effectiveness on many waxes, oils and resins.
  • the at least one glycol ether is chosen from glycol ethers derived from propylene oxide.
  • the at least one glycol ether is chosen from the group consisting of 2-Propylene Glycol 1-Methyl Ether (2PG1 ME or PGME), 2-Propylene Glycol 1-Methyl Ether Acetate (2PG1 MEA), Di-Propylene Glycol Methyl Ether (DPGME), Propylene Glycol Dimethyl Ether (PGDME), 2-Propylene Glycol 1-Ethyl Ether (2PG1EE), 2-Propylene Glycol 1-Ethyl Ether Acetate (2PG1 EEA), Propylene Glycol n-Propyl Ether (PGnPE), 2-Propylene Glycol 1-n-Butyl Ether (2PG1 BE), Propylene Glycol 1-tert-Butyl Ether (PG1tBE), Propylene Glycol Pheny
  • the at least one glycol ether is chosen from glycol ethers derived from ethylene oxide.
  • the at least one glycol ether is chosen from the group consisting of Di-Ethylene Glycol Ethyl Ether (DEGEE), Ethylene Glycol n-Propyl Ether (EGnPE), Ethylene Glycol n-Propyl Ether Acetate (EGnPEA), Ethylene Glycol iso-Propyl Ether (EGiPE), Ethylene Glycol Hexyl Ether (EGHE), Ethylene Glycol Phenyl Ether (EGPhE), Ethylene Glycol n-Butyl Ether (EGBE), Ethylene Glycol tert-Butyl Ether (EGtBE).
  • DEGEE Di-Ethylene Glycol Ethyl Ether
  • EGnPE Ethylene Glycol n-Propyl Ether
  • the at least one glycol ether is chosen from the alternative group consisting of Butylene Glycol Methyl Ether, Butylene Glycol di-Methyl Ether, Butylene Glycol Ethyl Ether, Butylene Glycol Propyl Ether, 3-Methyl 3-Methoxy Butanol (MMB).
  • glycol ethers are known to form azeotropic compositions with water, i.e. forming a mixture which has, for a particular composition, a vapor phase having the same composition than the liquid phase with which it is in equilibrium.
  • Known water-glycol azeotropes are called positive: their boiling temperature is lower than that of the pure components. This results in a higher vapour pressure than the pure components, which improves the volatility of the system.
  • glycol ethers listed above may be cited as positive azeotropic glycol ethers: 2-Propylene Glycol 1-Methyl Ether (2PG1ME), 2-Propylene Glycol 1-Methyl Ether Acetate (2PG1MEA), Di-Propylene Glycol Methyl Ether (DPGME), Ethylene Glycol Hexyl Ether (EGHE), Butyl Ethoxy Ethanol (BEE).
  • the preferred azeotropic glycol ether is 2-Propylene Glycol 1-Methyl Ether (2PG1ME or PGME), available from Dow Chemical under the trade name Dowanol ® PM.
  • the optimum content is in the concentration range from 30 to50% by weight of the composition of the invention.
  • the compound A is a mixture of a compound A1 which is the 2-Propylene Glycol 1-Methyl Ether (2PG1 ME), and a compound A2 which is at least one among the 3-Methyl 3-Methoxy Butanol (MMB)and the Propylene Glycol Propyl Ether, preferably in a mass ratio compound A1:compound A2 in the range from 1:1 to 3:1.
  • the glycol ether mixture comprises or consists of 2-Propylene Glycol 1-Methyl Ether and 3-Methyl 3-Methoxy Butanol.
  • the at least one linear or branched, saturated or unsaturated, C1 to C4 alcohol of compound B has a vapor pressure greater than 2.3 kPa at 20°C, in order to promote volatility of the composition by a drag-out effect (water being the main phase of the composition).
  • at least one linear or branched, saturated or unsaturated, C1 to C4 alcohol is chosen from the group consisting of ethanol, 1-propanol, isopropanol, and tert-butanol.
  • the use of short-chain solvents reduces the surface tension of the composition and allows it to better wet the surfaces and dirt.
  • the use of compound B in the invention may not exceed 15% by weight of the total glycol ether content, more preferably may not exceed 5% by weight of the total glycol ether content.
  • the at least one linear or branched, saturated or unsaturated, C2 to C5 polyol and having no more than 3 hydroxyl functions of compound C is chosen from the group consisting of Ethylene Glycol, Diethylene Glycol, Triethylene Glycol, Propylene Glycol, Trimethylene Glycol, n-Butylene glycol, 2,3-Butylene glycol, Neopentyl Glycol, Glycerol. Thanks to their hygroscopic properties, the polyols in the composition also act as humectants, facilitating the cleaning of dried-out dirt.
  • the mass ratio of compound C to compound A does not exceed 1:20, more preferably does not exceed 1:25.
  • the mass ratio of compound C to compound B is 1:1.
  • the 2-Propylene Glycol 1-Methyl Ether of the composition of present invention cooperates with monohydroxy alcohol on the one hand to reduce the freezing point.
  • monohydroxy alcohol due to its higher viscosity than that of monohydroxy alcohol, and its lower volatility, it adsorbs on the glass surface, increases the dwell time and therefore enhances the effect of washing or dirt removal. At the same time, it contributes to the reduction of the friction between the wiper and the glass.
  • composition of the present invention comprises:
  • composition of the present invention comprises:
  • the mass ratio compound B and/or compound C:compound A is in the range of 1:90 to 1:9.
  • a composition of the present invention further comprises at least one surfactant which is anionic, non-ionic, amphoteric or a mixture thereof, chosen from the group consisting of ethers of the carboxylic acids, alkyl aryl sulfonates containing an alkyl radical of from 8 to 16 carbon atoms and no substituent other than alkyl, alkyl ether sulfates containing an alkyl radical of from 8 to 18 carbon atoms and no substituent other than alkyl with different degrees of ethoxylation (average number of ethoxylation moles between 0.5 to 5), alkyl sulfates containing an alkyl radical of from 12 to 18 carbon atoms and no substituent other than alkyl, alcohols containing an alkyl radical of from 12 to 18 carbon atoms and no substituent other than alkyl with different degrees of ethoxylation (average number of ethoxylation moles between 3 to 20), N-alkylamine oxides containing an anionic, non-i
  • a composition of the present invention further comprises a cationic surfactant such as a copolymer of polydimethylsiloxane and organic quaternary amine which is responsible for the spontaneous cracking of the water layer to enhance the drying effect and improve the water repellency of the cleaned surfaces.
  • a cationic surfactant such as a copolymer of polydimethylsiloxane and organic quaternary amine which is responsible for the spontaneous cracking of the water layer to enhance the drying effect and improve the water repellency of the cleaned surfaces.
  • Copolymer of polydimethysiloxane and organic quaternary amine is available for example from EVONIK Industries AG under the trade name Tegropren ® 6922.
  • surfactant is used in a concentration superior or equal to 0.001 wt% and inferior or equal to 0.1 wt%, 0.001 wt% ⁇ [surfactant] ⁇ 0.1 wt%, the wt% being based on the total weight of the composition.
  • Anionic, cationic, non-ionic, amphoteric surfactants improve cleaning or soil removal properties.
  • surfactant may be helpful in removing or repelling insects from surfaces. It is assumed that the synergistic effect of the glycol ether / surfactant combination is due to the sticky and film-forming effect of the surfactant which improves the contact of the end-use product with the insect and enhances the ability of surfactants to dewax the insect's protective coating. The insect becomes dehydrated or is easily attacked by ever-present environmental microbes. The insect repellent activity is prolonged over time for example due to the use of biosurfactant such as a sophorolipid which resists repeated rinsing.
  • a composition of the present invention may also comprise an insect repellent such as octanoic, nonanoic or decanoic acid, or citronella oil, geraniol, cedar oil and similar.
  • an insect repellent such as octanoic, nonanoic or decanoic acid, or citronella oil, geraniol, cedar oil and similar.
  • the present invention also concerns the use of a composition of the present invention, in a liquid cleaning composition.
  • the composition is used as a cleaning composition for cleaning metal.
  • the composition is intended to improve the wetting by water of the surface to which the product is applied.
  • the surface is a glass surface such as a window.
  • the composition is used for washing vehicle windscreens.
  • the detergent is contained in the tank provided for this purpose, and is administered via the dispensing nozzles.
  • the cleaner is dispensed in a spray-aerosol can, after pressurization by a non-flammable gas.
  • Another embodiment is the provision of the product by a hand sprayer.
  • Figure 1 represents the aqueous cryoscopic constant (relationship between the freezing point and molality of the solute) for different compositions with (in circles) or without (in squares) propylene glycol methyl ether (PGME).
  • PGME propylene glycol methyl ether
  • Flash point measurement was based on closed cup Pensky-Martens measurement according to the ASTM D93 method (and on Setaflash apparatus according to the ASTM D3278 method).
  • Freezing points measurements were performed according to standards NF T 78-102 and ASTM D1177. The result is approximated to the nearest unit. For purposes of the examples in Table 1, 2 and 3, acceptable result was a freezing point less than or equal to -15°C.
  • the drying speed was evaluated comparatively from the evaporation time of 1 drop of detergent composition deposited on a glass plate, placed in a non-ventilated oven maintained at 25°C.
  • the results were scored according to the following rating scale namely that ⁇ : evaporation time less than or equal to 2 hours; ⁇ : evaporation time between 2 and 4 hours; ⁇ : evaporation time between 4 and 6 hours; ⁇ evaporation time greater than 6 hours.
  • acceptable result was an evaporation time less than or equal to 2 hours.
  • the dirt of the cleaning test was a 200g/L dispersion of various dusts within a low viscous API Group I mineral oil. 1mL of this dispersion was applied to a glass surface and left in contact for 24 hours at 100°C, causing a slight varnishing.
  • the test itself consisted of applying 1mL of the product to be studied for 10s, then wiping with a single stroke of the cloth. This cleaning operation was repeated twice.
  • the result was scored after visual inspection of the transparency of the glass surface according to the following rating scale namely that ⁇ : no traces; ⁇ : light traces that do not hinder observation; ⁇ : traces that hinder observation. For purposes of the examples in Table 1, acceptable result was no traces.
  • the freezing point is the temperature at which crystallization begins in the absence of supercooling, or the maximum temperature reached immediately after initial crystal formation in the case of supercooling.
  • the law of aqueous cryometry stipulates that the depression of the freezing point of a system is proportional to the molality b of the solute.
  • compositions of the present invention containing a majority proportion of compound A1 in the range of 15 to 40% by weight on the total weight of the composition
  • compound A1 such as a propylene glycol methyl ether (PGME) which provides an azeotropic behaviour with water
  • PGME propylene glycol methyl ether
  • the azeotropic compositions Water - Compound A1 generated vapor pressures almost 30% higher than the theoretical vapor pressure calculated according to Raoult's law.
  • a 40% by weight solution of propylene glycol methyl ether (PGME) has a vapor pressure measured according to the ASTM D2879 method of 2.9kPa at 20°C, instead of about 2.2kPa theoretically.
  • Table 2 shows the results of the properties obtained with a suitable combination of components (A1), (A2), (B) and (C) (Ex. 1 to 4) of the invention, while comparative examples (Ex. Comp. 1 to 9) show the results obtained with the components taken independently.
  • A1 was meant a glycol ether with azeotropic behaviour, preferably propylene glycol methyl ether (PGME).
  • PGME propylene glycol methyl ether
  • A2 was meant one or more glycol ethers which do not behave azeotropically with water, preferably 3-Methyl 3-Methoxy Butanol (MMB), Propylene Glycol Propyl Ether or any combination thereof.
  • MMB 3-Methyl 3-Methoxy Butanol
  • B was meant a polar solvent with less than 4 carbon atoms, preferably ethanol
  • C was meant a polyol with less than 5 carbon atoms, preferably ethylene glycol (EG).
  • the maximum glycol ether content may not exceed 50% by weight of the total formulation. Above this limit, combinations of compounds A1 and A2 may either lead to an increase in freezing point and a decrease in drying kinetics if there is an excess of compound A2, or to a flammable product if there is an excess of compound A1.
  • Table 3 shows the results of adding ethylene glycol as a freezing point depressant. Although ethanol can also play this role, its action on lowering the flash point made it difficult to use in large proportions. It was preferable to play on the compound A1/A2 ratio, the azeotropic glycol ether being favourable to freezing point depression.

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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)
  • Health & Medical Sciences (AREA)
  • Emergency Medicine (AREA)
  • Detergent Compositions (AREA)
EP21305734.2A 2021-06-01 2021-06-01 Nichtentflammbare, flüchtige und wässrige reinigungszusammensetzung Pending EP4098729A1 (de)

Priority Applications (2)

Application Number Priority Date Filing Date Title
EP21305734.2A EP4098729A1 (de) 2021-06-01 2021-06-01 Nichtentflammbare, flüchtige und wässrige reinigungszusammensetzung
PCT/EP2022/064811 WO2022253857A1 (en) 2021-06-01 2022-05-31 Non-flammable, volatile and aqueous cleaning composition

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Application Number Priority Date Filing Date Title
EP21305734.2A EP4098729A1 (de) 2021-06-01 2021-06-01 Nichtentflammbare, flüchtige und wässrige reinigungszusammensetzung

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EP4098729A1 true EP4098729A1 (de) 2022-12-07

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Citations (15)

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Publication number Priority date Publication date Assignee Title
US2031145A (en) 1930-07-14 1936-02-18 Standard Oil Co Nonflammable cleaning solvent
EP0347924A1 (de) 1988-06-22 1989-12-27 Asahi Glass Company Ltd. Verwendung von Halogenkohlenwasserstofflösungsmittel als Reinigungsmittel
EP0443911A1 (de) 1990-02-20 1991-08-28 Elf Atochem S.A. Anwendung von Perfluoralkyl-Ethylenen als Reinigungs- oder Trocknungsmittel
WO1994003579A1 (en) 1992-08-06 1994-02-17 Lockheed Corporation Nonflammable mild odor solvent cleaner
WO1995007974A1 (en) * 1993-09-15 1995-03-23 The Dow Chemical Company Cleaning composition
US5486314A (en) 1992-08-07 1996-01-23 O. K. Wack Chemie Gmbh Cleaning agent containing glycol ethers
US20110230380A1 (en) * 2010-03-17 2011-09-22 Method Products, Inc. Liquid cleaning compositions with lower freezing point
US8114223B2 (en) 2007-03-07 2012-02-14 Henkel Ag & Co. Kgaa Glass cleaner comprising an alkylpyrrolidone, glycol ether, and anionic surfactant
US8845817B2 (en) 2012-06-07 2014-09-30 Green Way Laboratories Non-toxic cleaning agent
US9085751B2 (en) 2010-07-09 2015-07-21 Kaken Tech Co., Ltd. Liquid concentrate for cleaning composition, cleaning composition and cleaning method
US20160230127A1 (en) 2012-09-13 2016-08-11 Gregg Motsenbocker Low-VOC Water-Based Cleaner For Pen, Ink, Markers, Paint
EP3118295A1 (de) * 2015-07-13 2017-01-18 The Procter and Gamble Company Glykoletherlösungsmitteln in flüssigen reinigungsmittelzusammensetzungen zur entfernung von flecken von oberflächen
CN106867702A (zh) * 2015-12-14 2017-06-20 宋桂芝 一种汽车玻璃用玻璃水
EP3422392A1 (de) * 2017-06-05 2019-01-02 Versum Materials US, LLC Ätzlösung zum selektiven entfernen von siliciumnitrid während der herstellung eines halbleiterbauelements
CN109504553A (zh) * 2018-12-28 2019-03-22 北京绿伞化学股份有限公司 一种汽车用玻璃清洁剂及其制备方法

Patent Citations (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2031145A (en) 1930-07-14 1936-02-18 Standard Oil Co Nonflammable cleaning solvent
EP0347924A1 (de) 1988-06-22 1989-12-27 Asahi Glass Company Ltd. Verwendung von Halogenkohlenwasserstofflösungsmittel als Reinigungsmittel
EP0443911A1 (de) 1990-02-20 1991-08-28 Elf Atochem S.A. Anwendung von Perfluoralkyl-Ethylenen als Reinigungs- oder Trocknungsmittel
WO1994003579A1 (en) 1992-08-06 1994-02-17 Lockheed Corporation Nonflammable mild odor solvent cleaner
US5486314A (en) 1992-08-07 1996-01-23 O. K. Wack Chemie Gmbh Cleaning agent containing glycol ethers
WO1995007974A1 (en) * 1993-09-15 1995-03-23 The Dow Chemical Company Cleaning composition
US8114223B2 (en) 2007-03-07 2012-02-14 Henkel Ag & Co. Kgaa Glass cleaner comprising an alkylpyrrolidone, glycol ether, and anionic surfactant
US9879204B2 (en) 2010-03-17 2018-01-30 Method Products, Pbc Liquid cleaning compositions with lower freezing point
US20110230380A1 (en) * 2010-03-17 2011-09-22 Method Products, Inc. Liquid cleaning compositions with lower freezing point
US9085751B2 (en) 2010-07-09 2015-07-21 Kaken Tech Co., Ltd. Liquid concentrate for cleaning composition, cleaning composition and cleaning method
US8845817B2 (en) 2012-06-07 2014-09-30 Green Way Laboratories Non-toxic cleaning agent
US20160230127A1 (en) 2012-09-13 2016-08-11 Gregg Motsenbocker Low-VOC Water-Based Cleaner For Pen, Ink, Markers, Paint
EP3118295A1 (de) * 2015-07-13 2017-01-18 The Procter and Gamble Company Glykoletherlösungsmitteln in flüssigen reinigungsmittelzusammensetzungen zur entfernung von flecken von oberflächen
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CN106867702A (zh) * 2015-12-14 2017-06-20 宋桂芝 一种汽车玻璃用玻璃水
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