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WO2025129874A1 - Composition de rhamnolipides pour le nettoyage de l'huile de silicone et agent de nettoyage industriel - Google Patents

Composition de rhamnolipides pour le nettoyage de l'huile de silicone et agent de nettoyage industriel Download PDF

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Publication number
WO2025129874A1
WO2025129874A1 PCT/CN2024/088809 CN2024088809W WO2025129874A1 WO 2025129874 A1 WO2025129874 A1 WO 2025129874A1 CN 2024088809 W CN2024088809 W CN 2024088809W WO 2025129874 A1 WO2025129874 A1 WO 2025129874A1
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Prior art keywords
parts
rhamnolipid
composition
cleaning
type
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Pending
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PCT/CN2024/088809
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English (en)
Chinese (zh)
Inventor
姚丹
李棒棒
周卓
石森
纪学顺
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Wanhua Chemical Group Co Ltd
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Wanhua Chemical Group Co Ltd
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Publication of WO2025129874A1 publication Critical patent/WO2025129874A1/fr
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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
    • C11D1/662—Carbohydrates or derivatives
    • 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
    • C11D1/825—Mixtures of compounds all of which are non-ionic
    • 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
    • C11D3/2075—Carboxylic acids-salts thereof
    • C11D3/2086—Hydroxy carboxylic acids-salts thereof
    • 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
    • C11D3/37—Polymers
    • C11D3/3703—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C11D3/373—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing silicones
    • 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
    • C11D1/667—Neutral esters, e.g. sorbitan esters
    • 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
    • C11D1/74—Carboxylates or sulfonates esters of polyoxyalkylene glycols

Definitions

  • the invention relates to the technical field of industrial cleaning, in particular to a rhamnolipid composition for cleaning silicone oil, and also to a cleaning agent composition and an industrial cleaning agent comprising the rhamnolipid composition.
  • Rhamnolipid has good permeability, contains sugar ring structure, can penetrate into oil, and has strong cleaning efficiency compared with other carbon-based surfactants, and rhamnolipid can be completely degraded in nature, which is in line with current environmental protection concepts.
  • the inventors have obtained the appropriate composition ratio of the two through a large number of experiments, and the rhamnolipid composition obtained therefrom can have excellent wettability and cleaning ability, and is therefore very suitable for the cleaning of silicone oil, especially equipment or components such as tanks and pipelines containing silicone oil.
  • the rhamnolipid composition can include 20 to 40 parts (for example, about 20 parts, about 25 parts, about 30 parts, about 35 parts, about 40 parts, or any weight range) of Rha-C10C10 rhamnolipid and 40 to 60 parts (for example, about 40 parts, about 45 parts, about 50 parts, about 55 parts, about 60 parts, or any weight range) of RhaRha-C10C10 rhamnolipid, based on weight.
  • 20 to 40 parts for example, about 20 parts, about 25 parts, about 30 parts, about 35 parts, about 40 parts, or any weight range
  • 40 to 60 parts for example, about 40 parts, about 45 parts, about 50 parts, about 55 parts, about 60 parts, or any weight range
  • the rhamnolipid composition may also include one or more of the following rhamnolipid types, measured by weight: 0.1 to 10 parts of RhaRha-C8C10 type, 0.1 to 2 parts of Rha-C8C10 type, 0.5 to 20 parts of RhaRha-C10C12 type, 0.1 to 10 parts of RhaRha-C10C12:1 type, 0.1 to 5 parts of Rha-C10C12 type, and 0.1 to 5 parts of Rha-C10C12:1 type.
  • the rhamnolipid composition may also include one or more of the following rhamnolipid types, measured by weight: 0.2 to 5 parts of RhaRha-C8C10 type, 0.3 to 1 parts of Rha-C8C10 type, 5 to 10 parts of RhaRha-C10C12 type, 0.2 to 5 parts of RhaRha-C10C12:1 type, 0.2 to 2.5 parts of Rha-C10C12 type, and 0.2 to 2.5 parts of Rha-C10C12:1 type.
  • the rhamnolipid described in the present invention can be rhamnolipid and its salts, including inorganic salts and organic salts of rhamnolipid, wherein the inorganic salts include but are not limited to metal salts such as K + , Na + , Mg 2+ , Ca 2+ , Al 3+ , etc.; the organic salts include but are not limited to salts formed by NH 4+ , primary amines, secondary amines, tertiary amines, etc. and rhamnolipid.
  • the inorganic salts include but are not limited to metal salts such as K + , Na + , Mg 2+ , Ca 2+ , Al 3+ , etc.
  • the organic salts include but are not limited to salts formed by NH 4+ , primary amines, secondary amines, tertiary amines, etc. and rhamnolipid.
  • the rhamnolipid of the present invention can be a mixture obtained by compounding various types of rhamnolipid pure products, or it can be a concentrated fermentation broth produced by fermentation.
  • the rhamnolipid composition is a concentrated fermentation broth produced by fermentation of Pseudomonas aeruginosa, and the fermentation method can be a commonly used method in the art.
  • the ratio of the rhamnolipid composition of the present invention can be obtained by adjusting the fermentation conditions.
  • the rhamnolipid composition provided by the present invention may further include a defoamer.
  • a defoamer Compared with other low-foaming surfactants, rhamnolipids have moderate foaming properties, and di-rhamnolipids in particular have higher foaming properties.
  • the industrial cleaning field generally requires low foaming properties, so adding a defoamer to the rhamnolipid system can significantly reduce the foaming properties, further improving the cleaning ability and cleaning effect for silicone oil.
  • the defoaming agent can be added in two ways: one is to add the defoaming agent according to the required concentration after obtaining the fermentation broth with a determined composition; the other is to add a portion of the defoaming agent during the fermentation process, and after quantitatively confirming the concentration (for example, by HPLC quantification), add the defoaming agent to reach the required concentration.
  • the defoaming agent may be an organic silicon defoaming agent such as emulsified silicone oil and polydimethylsiloxane, which can increase the compatibility of rhamnolipid and silicone oil to improve the cleaning effect.
  • organic silicon defoaming agent such as emulsified silicone oil and polydimethylsiloxane, which can increase the compatibility of rhamnolipid and silicone oil to improve the cleaning effect.
  • the amount of the defoamer can be 0.1 to 10 wt.% of the total weight of all rhamnolipid types (for example, it can be about 0.1 wt.%, about 0.5 wt.%, about 1 wt.%, about 2 wt.%, about 3 wt.%, about 4 wt.%, about 5 wt.%, about 6 wt.%, about 7 wt.%, about 8 wt.%, about 9 wt.%, about 10 wt.%, or any weight percentage interval).
  • the amount of the defoamer can be 1 to 5 wt.% of the total weight of all rhamnolipid types.
  • the second aspect of the present invention provides use of the rhamnolipid composition described in any one of the above technical solutions in the preparation of a cleaning agent.
  • the cleaning agent may be an industrial cleaning agent used to clean silicone oil.
  • the third aspect of the present invention provides a cleaning agent composition, comprising the rhamnolipid composition described in any one of the above technical solutions.
  • the cleaning agent composition can be used to clean silicone oil.
  • the cleaning agent composition may include, by weight: 5 to 25 parts (e.g., about 5 parts, about 8 parts, about 10 parts, about 12 parts, about 15 parts, about 18 parts, about 20 parts, about 22 parts, about 25 parts, or any weight range) of the rhamnolipid composition, 0 to 3 parts (e.g., about 0.1 parts, about 0.2 parts, about 0.5 parts, about 0.8 parts, about 1 parts, about 1.2 parts, about 1.5 parts, about
  • the pharmaceutical composition comprises: a compounding agent of 1-2 parts (for example, about 2 parts, about 2.5 parts, about 3 parts or any weight range) of a compounding agent, 2-10 parts (for example, about 2 parts, about 3 parts, about 4 parts, about 5 parts, about 6 parts, about 7 parts, about 8 parts, about 9 parts, about 10 parts or any weight range) of a pH adjusting agent, and 1-8 parts (for example, about 1 part, about 2 parts, about 3 parts, about 4 parts,
  • the cleaning agent composition may include, by weight: 5 to 10 parts of the rhamnolipid composition, 0.5 to 1.5 parts of a compounding agent, 2 to 8 parts of a pH adjuster and 2 to 6 parts of sodium gluconate.
  • the cleaning agent composition provided by the present invention may further include alkyl polymethylsiloxane or phenyl polymethylsiloxane. Such substances can further enhance the compatibility of rhamnolipid and silicone oil to achieve a faster and more thorough cleaning purpose.
  • the cleaning composition may further include 0.1 to 2 parts (for example, about 0.1 parts, about 0.2 parts, about 0.3 parts, about 0.4 parts, about 0.5 parts, about 0.8 parts, about 1 parts, about 1.2 parts, about 1.5 parts, about 1.8 parts, about 2 parts or any range of parts by weight) of alkyl polymethylsiloxane.
  • the alkyl polymethylsiloxane can be selected from one or more of octyl polymethylsiloxane, dodecyl polymethylsiloxane, and hexadecyl polymethylsiloxane.
  • the compounding agent can be selected from one or more of sucrose esters, alkyl glycosides, coconut oil diethanolamide, polysorbate, fatty alcohol esters, and glyceryl monostearate.
  • the compounding agent and rhamnolipid can further improve the cleaning effect.
  • a fourth aspect of the present invention provides an industrial cleaning agent, comprising 5 to 40 wt.% (for example, about 5 wt.%, about 10 wt.%, about 15 wt.%, about 20 wt.%, about 25 wt.%, about 30 wt.%, about 35 wt.%, about 40 wt.% or any weight percentage range) of the cleaning agent composition described in any one of the above technical solutions and 60 to 95 wt.% of water.
  • 5 to 40 wt.% for example, about 5 wt.%, about 10 wt.%, about 15 wt.%, about 20 wt.%, about 25 wt.%, about 30 wt.%, about 35 wt.%, about 40 wt.% or any weight percentage range
  • the industrial cleaning agent can be used to clean silicone oil, such as equipment or components such as tanks and pipelines containing silicone oil.
  • the industrial cleaning agent provided by the present invention can be prepared using a common preparation process in the art, for example, by adding the various components into water in any order to achieve a desired weight percentage range.
  • the rhamnolipid composition provided by the present invention can balance emulsification, wettability and foaming properties. On the basis of high emulsification, high wettability can enable the cleaning agent to quickly infiltrate the silicone oil contact surface and emulsify the oil, while low foaming is conducive to rapid cleaning. Therefore, the rhamnolipid composition of the present invention has strong cleaning ability and fast cleaning speed, and is therefore very suitable for cleaning and removing silicone oil in the industrial field.
  • the rhamnolipid composition provided by the present invention has a simple preparation process, is inexpensive and readily available, and can obtain a variety of products with different properties by adjusting the proportion of the components of the composition. It has a wide range of applications. Moreover, rhamnolipid is a biodegradable substance and is environmentally friendly.
  • the industrial cleaning agent provided by the present invention has excellent silicone oil removal ability, and the oil removal efficiency can reach 95% The above is even higher, so it has very wide application potential in the field of industrial cleaning and is suitable for large-scale production and application.
  • rhamnolipid refers to the concentrated fermentation liquid produced by the fermentation of Pseudomonas aeruginosa, and its preparation process is as follows:
  • Rhamnolipid fermentation broth firstly, Pseudomonas aeruginosa is inoculated on a solid culture medium by a plate streaking method to activate the strain; then, a single colony is picked from the activated strain and inoculated into a seed culture medium (composition includes: peptone 10.0 g/L, yeast powder 5.0 g/L, NaCl 10.0 g/L), and cultured at 30°C for 6 hours to obtain a seed solution; then, the seed solution is inoculated into a fermentation culture medium (composition includes: yeast extract 5 g/L, urea 5 g/L, sodium nitrate 10 g/L, Na 2 HPO 4 4 g/L, KH 2 PO 4 4 g/L, CaCl 2 0.4 g/L, MgSO 4 2 g/L) at an inoculation amount of 1-10 vol%, and cultured to obtain a rhamnolipid fermentation broth.
  • a seed culture medium composition includes:
  • the rhamnolipid fermentation broth was centrifuged at 6000rpm for 15min, the supernatant was collected and 38wt% concentrated hydrochloric acid was added thereto to adjust the pH to 1.5-2.0, and then the mixture was placed in a refrigerator at 4°C for 24h, and centrifuged again at 6000rpm for 10min to collect the precipitate; the precipitate was mixed with 3 times the volume of methanol, filtered with a 30000Da ultrafiltration membrane, the filtrate was collected, and then the methanol was evaporated at 70°C for 3h using a rotary evaporator to obtain a paste; the paste was mixed with the same volume of water, and then the pH was adjusted to above 6.0 with a 3M sodium hydroxide aqueous solution, stirred and dissolved for 2h, pre-frozen at -80°C for 3h, and then placed in a freeze dryer at -86°C for freezing Dry for 48 hours to obtain rhamnolipid.
  • fermentation broths with different components were obtained by adjusting the fermentation and separation and purification process parameters.
  • the specific components quantified by HPLC) were shown in the examples and comparative examples.
  • the rhamnolipid of Example 1 was named "rhamnolipid-1", and rhamnolipid-1 was used to construct the compositions of rhamnolipid and defoaming agent.
  • Example 1-1 The formula of Example 1-1 is as follows:
  • composition of rhamnolipids is as follows:
  • Example 2-2 The formula of Example 2-2 is as follows:
  • the rhamnolipid of Comparative Example 2 was named "Rhamnolipid-Comparative 2", and rhamnolipid-Comparative 2 was used to construct compositions of rhamnolipid and defoaming agent.
  • the foaming power of a sample with an effective content of 2.5 g/L of rhamnolipids in 150 mg/kg hard water was measured using a Roche foam meter.
  • the foam height of the sample was tested at 0 min.
  • the test temperature was 40°C.
  • the sample was measured 3 times and the average value was taken.
  • the test data are shown in Table 1-1 and Table 1-2:
  • the comprehensive foaming and wetting properties test results show that, under the same composition, the higher the defoamer content, the lower the foam height, the easier it is to clean, the smaller the contact angle, and the easier it is to spread; the higher the RhaRha-C10C10 content, the higher the foam height, the harder it is to clean, the larger the contact angle, and the harder it is to spread.
  • AEO9 has lower foaming properties, but a larger contact angle, and is not easy to spread on the silicone oil surface.
  • Rhamnolipid (a combination of rhamnolipid and a defoaming agent) was prepared into a cleaning agent for industrial cleaning, and its ability to remove silicone oil was evaluated.
  • the cleaning agent comprises, by weight: 6 parts of effective rhamnolipid content (calculated as rhamnolipid content), 0 parts or 0.5 parts of octyl polymethylsiloxane, 1 part of alkyl glycoside, 0.5 parts of citric acid, 4 parts of sodium citrate, 3 parts of sodium gluconate, and 100 parts of water.
  • the cleaning agent of Comparative Example 3 includes, by weight: 7 parts of AEO9 surfactant, 1 part of alkyl glycoside, 0.5 parts of citric acid, 4 parts of sodium citrate, 3 parts of sodium gluconate, and 100 parts of water.
  • the same type of stainless steel plate surface was subjected to an oil removal cleaning test.
  • the test process was to apply oil (a mixture of silicone oil and dust, the source of silicone oil being the same as in Test Example 2) on the surface of the stainless steel plate, and then use a sufficient amount of the above-mentioned cleaning agent to clean it, and then rinse it with clean water and dry it.
  • Example 2-1 has the highest cleaning ability.
  • cleaning silicone oil stains requires good cleaning power, permeability and low foam.
  • RhaRha-C10C10 content is too high, the emulsification ability is strong but the permeability is insufficient.
  • Rha-C10C10 content is too high, the permeability is strong but the emulsification power is insufficient.
  • a small amount of octyl polymethylsiloxane is preferably added to the formula system of the cleaning agent, which can further increase the compatibility between the surfactant and the silicone oil, and has better compatibility and permeability to the silicone oil.
  • the cleaning agent ingredients can form micelles with a diameter of 50-100nm with the silicone oil, which are easy to remove. When the micelle diameter is too large or too small, the cleaning effect will be affected.

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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)
  • Molecular Biology (AREA)
  • Emergency Medicine (AREA)
  • Detergent Compositions (AREA)

Abstract

La présente invention concerne une composition de rhamnolipides pour le nettoyage de l'huile de silicone, comprenant, en parties en poids, 10 à 50 parties de rhamnolipide Rha-C10C10 et 35 à 85 parties de rhamnolipide RhaRha-C10C10. La présente invention concerne en outre une utilisation de la composition de rhamnolipides, et une composition d'agent de nettoyage et un agent de nettoyage industriel qui comprennent la composition de rhamnolipides. La composition de rhamnolipides selon la présente invention permet d'obtenir un équilibre entre l'émulsibilité, la mouillabilité et la moussabilité, présente une capacité de nettoyage élevée et une vitesse de nettoyage élevée, et convient très bien pour nettoyer et éliminer l'huile de silicone dans le domaine industriel. L'agent de nettoyage industriel selon la présente invention a une excellente capacité d'élimination de l'huile de silicone, possède un très large potentiel d'application dans le domaine du nettoyage industriel, et est approprié pour une production et une application à grande échelle.
PCT/CN2024/088809 2023-12-21 2024-04-19 Composition de rhamnolipides pour le nettoyage de l'huile de silicone et agent de nettoyage industriel Pending WO2025129874A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CN202311772803.4A CN117535104B (zh) 2023-12-21 2023-12-21 一种用于清洗硅油的鼠李糖脂组合物以及工业清洗剂
CN202311772803.4 2023-12-21

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WO2025129874A1 true WO2025129874A1 (fr) 2025-06-26

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Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN117535104B (zh) * 2023-12-21 2024-05-17 万华化学集团股份有限公司 一种用于清洗硅油的鼠李糖脂组合物以及工业清洗剂

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CN114456880A (zh) * 2020-11-09 2022-05-10 万华化学(四川)有限公司 一种鼠李糖脂厨房重油污清洗剂及其制备方法
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CN117731549A (zh) * 2023-12-20 2024-03-22 万华化学集团股份有限公司 一种防腐乳液组合物及其制备方法和应用

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WO2017089093A1 (fr) * 2015-11-25 2017-06-01 Unilever N.V. Composition de détergent liquide

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Publication number Priority date Publication date Assignee Title
EP2410039A1 (fr) * 2010-07-22 2012-01-25 Unilever PLC Rhamnolipides à nettoyage amélioré
CN107427438A (zh) * 2015-02-27 2017-12-01 赢创德固赛有限公司 包含鼠李醣脂和硅氧烷的组合物
WO2019034490A1 (fr) * 2017-08-16 2019-02-21 Henkel Ag & Co. Kgaa Détergent et nettoyant à base de rhamnolipides
CN109536972A (zh) * 2018-12-20 2019-03-29 新沂肽科生物科技有限公司 一种金属加工制品表面清洗剂组合物及其制备和使用方法
CN114456880A (zh) * 2020-11-09 2022-05-10 万华化学(四川)有限公司 一种鼠李糖脂厨房重油污清洗剂及其制备方法
CN117731549A (zh) * 2023-12-20 2024-03-22 万华化学集团股份有限公司 一种防腐乳液组合物及其制备方法和应用
CN117535104A (zh) * 2023-12-21 2024-02-09 万华化学集团股份有限公司 一种用于清洗硅油的鼠李糖脂组合物以及工业清洗剂

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