EP4650428A1 - Solvant de nettoyage d'origine biologique comprenant un mélange d'acétate d'éthyle et de térébenthine brute - Google Patents

Solvant de nettoyage d'origine biologique comprenant un mélange d'acétate d'éthyle et de térébenthine brute

Info

Publication number
EP4650428A1
EP4650428A1 EP24175462.1A EP24175462A EP4650428A1 EP 4650428 A1 EP4650428 A1 EP 4650428A1 EP 24175462 A EP24175462 A EP 24175462A EP 4650428 A1 EP4650428 A1 EP 4650428A1
Authority
EP
European Patent Office
Prior art keywords
bio
based solvent
solvent
substrate surface
vol
Prior art date
Legal status (The legal status 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 status listed.)
Pending
Application number
EP24175462.1A
Other languages
German (de)
English (en)
Inventor
David REHNLUND MAIBACH
Fionn O'FEARGHAIL
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Polestar Performance AB
Original Assignee
Polestar Performance AB
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 Polestar Performance AB filed Critical Polestar Performance AB
Priority to EP24175462.1A priority Critical patent/EP4650428A1/fr
Priority to PCT/EP2025/062817 priority patent/WO2025237856A1/fr
Publication of EP4650428A1 publication Critical patent/EP4650428A1/fr
Pending legal-status Critical Current

Links

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
    • C11D7/50Solvents
    • C11D7/5004Organic solvents
    • 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
    • C11D2111/00Cleaning compositions characterised by the objects to be cleaned; Cleaning compositions characterised by non-standard cleaning or washing processes
    • C11D2111/10Objects to be cleaned
    • C11D2111/14Hard surfaces

Definitions

  • the present disclosure is related to a bio-based cleaning solvent comprising a mixture of ethyl acetate and crude turpentine, which solvent may be used to remove lubricating oils, carbon deposits, paints, sealants, powder coatings, protective films and adhesives from for example metal tools, machined products, ceramic products and certain plastic products.
  • White spirits also known as mineral turpentine, is a petroleum-derived clear liquid commonly used as an organic solvent to remove lubricating oils from metal tools and machined products or to remove carbon-containing coatings, such as powder coatings, from surfaces.
  • Other alternative cleaning solutions are also predominantly based on solvents made using petrochemical derived products.
  • bio-based cleaning solvents available today, which are called “bio-based” as a portion of their contents is originally from a bio source. Most solvents that are claimed as “bio-based” are, however, determined as such via the mass balance approach and only comprise a certain percentage of bio-based material.
  • a bio-based cleaning solvent comprising a mixture of ethyl acetate and crude turpentine, wherein the ethyl acetate and crude turpentine mixture constitutes at least 95 vol.% of the biobased-solvent and wherein a ratio of ethyl acetate to crude turpentine in the bio-based solvent is 5:95 to 95:5 vol.%.
  • the bio-based cleaning solvent comprises a mixture of ethyl acetate and crude turpentine, which mixture constitutes at least 95 vol.%, or at least 96 vol.%, or at least 97 vol.%, or at least 98 vol.%, or at least 99 vol.%.
  • the rest may for example be inorganic residues remaining in the turpentine (traces of pulping chemicals, other carbon containing species from the pulping process, e.g. lignin, hemicellulose, cellulose etc.), residues from the production of ethyl acetate, such as ethanol, etc.
  • Ethyl acetate also known as ethyl ethanoate, EtOAc, ETAC, or EA
  • chemical formula CH 3 CO 2 CH 2 CH 3 or C 4 H 8 O 2 can be obtained as an output from bio-ethanol processing.
  • Ethyl acetate is considered a green or bio-based solvent as it is derived from renewable resources and has a low environmental impact. It is often used in cleaning products, coatings, paints etc.
  • Crude turpentine or gum turpentine, is obtained as an output from softwood processing.
  • Crude turpentine is composed of terpenes, primarily the monoterpenes alpha-pinene and beta-pinene, along with lesser amounts of carene, camphene, limonene, and terpinolene.
  • Crude turpentine may be used as a solvent and in organic chemistry processes.
  • the bio-based cleaning solvent comprising ethyl acetate and crude turpentine is, hence, a cleaning solution that is not petrochemically derived but fully bio-based.
  • the CO 2 e (carbon dioxide equivalent) footprint of the cleaning solvent is low and contributes towards overall reduction in CO 2 e footprint of the final cleaned/recycled product, as compared to petrochemical derived solvents.
  • the bio-based solvent will be much closer to zero GHG (greenhouse gas) impact than previously feasible.
  • the solvent can be used to chemically dissolve organic species from a material substrate, for example for removing residues of lubricating mineral oils,carbon deposits, paints, sealants, powder coatings, protective films and adhesives from for example metal tools, machined products, ceramic products and certain plastic products.
  • the solvent targets all carbon-contaminants and is agnostic to the type of material (size, shape, alloy composition etc).
  • the combination of ethyl acetate and crude turpentine enhances the solvating properties (penetration and solvation) of the solvent compared to if ethyl acetate or crude turpentine is used as a sole component of the solvent.
  • the crude turpentine has deep penetrating solvation properties and pierces into organic coatings and disrupts local bonds.
  • Crude turpentine is unprocessed and is a heterogeneous mixture of small aromatic organics present in differing concentrations. The presence of these small aromatic organics in the crude turpentine allow for the dissolution of a wide range of complex organic residues.
  • the ethyl acetate has a high solubility for polar compounds and enable efficient solvation of disrupted molecules.
  • a bio-based solvent comprising only ethyl acetate and no crude turpentine will not comprise a sufficiently heterogeneous mixture of small aromatic.
  • a bio-based solvent comprising only crude turpentine and no ethyl acetate will not penetrate complex surface geometries as effectively as with ethyl acetate included.
  • the solvent mixture enables efficient removal of oils and organic coatings such as powder coatings on e.g. aluminium profiles.
  • the flash point of ethyl acetate is approximately -4°C. At or above this temperature, the vapour of ethyl acetate can ignite when exposed to an open flame or spark.
  • the presence of the crude turpentine in the solvent increases the flash point of ethyl acetate, reducing the likelihood of ignition of the solvent.
  • US8414797B2 is shown that adding terpenes (part of crude turpentine) to methyl acetate (close analogue to ethyl acetate) the flash point increases considerably.
  • the above-describe cleaning solvent exhibits both broad spectrum affinity for organic residues and increased penetrating power when compared with petrochemical derived products, thanks to the range of terpene chemistries present in crude turpentine.
  • the cleaning solvent has an improved smell, is less flammable and less toxic than conventional petrochemical derived products, making it advantageous from a user experience and health and safety point of view.
  • the ratio of ethyl acetate to crude turpentine in the bio-based solvent may be 10:90 to 95:5 vol.%; 15:85 to 95:5 vol.%; 20:80 to 95:5 vol.%; 25:75 to 95:5 vol.%; 30:70 to 95:5 vol.%; 35:65 to 95:5 vol.%; 40:60 to 95:5 vol.%; 45:55 to 95:5 vol.%; 50:50 to 95:5 vol.%; 55:45 to 95:5 vol.%; 60:40 to 95:5 vol.%; 65:35 to 95:5 vol.%; 70:30 to 95:5 vol.%; 75:25 to 95:5 vol.%; 80:10 to 95:5 vol.%; 85:15 to 95:5; 90:10 to 95:5 vol.%; 5:95 to 90:10 vol.%; 5:95 to 85:15 vol.%; 5:95 to 80:20 vol.%; 5:95 to 75:25 vol.%; 5
  • bio-based solvent described above for cleaning a substrate surface from oil residues, carbon deposits, lubricants, paints, sealants, powder coatings, protective films and/or adhesives.
  • the substrate surface to be cleaned may be a metal or metal alloy surface, a ceramic surface, a polyethylene surface, a polypropylene surface, a polymethyl methacrylate surface, a polyether ether ketone surface, a polyphenylene sulfide surface, a polyamide 6,6 surface, or a polyamide 6 surface.
  • the substrate surface is the surface of aluminium scrap.
  • Electrically driven smelting of secondary aluminium feedstock i.e. scrap
  • requires low carbon contamination ⁇ ⁇ 2%.
  • Using this bio-based solvent to clean the aluminium scrap may not only remove GHG emissions during smelting but also allow the use of electrical furnace technologies (e.g. induction furnaces). These two factors will allow a potential zero greenhouse gas production route for aluminium recycling.
  • the bio-based solvent can be used to clean electronics printed circuit board (PCB) recycling.
  • PCB printed circuit board
  • a method of cleaning a substrate surface using the bio-based solvent described above comprising to immerse the substrate in the bio-based solvent or adding the bio-based solvent to said substrate surface for at least 1 minute.
  • the substrate may be immersed in the bio-based solvent/the bio-based solvent may be added to the substrate surface for at least 1 minute, or for at least 10 minutes, or for up to 60 minutes.
  • the bio-based solvent may have a temperature of -4 to 35°C when used in the method.
  • This temperature range is optimized based on the known flash points of ethyl acetate and crude turpentine, in conjunction with maximising the penetrating power of the solvent while maximising safety.
  • the substrate surface may be immersed in the bio-based solvent during agitation.
  • Agitation can be used to enhance the cleaning with the bio-based solvent and may be performed e.g. by using ultrasonication, or conventional stirring means, or by using rotating/vibrating metal brushes in contact with the substrate surface, while substrate is submerged in the solvent.
  • the substrate surface may be immersed in the bio-based solvent during mechanical processing of the substrate surface.
  • the substrate surface may be mechanically processed while being immersed in the bio-based solvent. This may for example be accomplished by using rotating/vibrating brushes (of metal) in contact with the substrate surface.
  • the substrate surface may be pre-treated before being immersed in the bio-based solvent or before the bio-based solvent is added to the substrate surface, the pre-treatment step comprising of one or more of:
  • the one or more pre-treatment steps may enhance the cleaning with the bio-based solvent.
  • Heating and cooling the substrate surface may comprise to heat the substrate surface to at least 80°C, then allowing the surface to cool to ⁇ 35°C, preferably repeating the process a few times.
  • Mechanically processing the substrate surface may comprise to brush the substrate surface with e.g. metal brushes, e.g. at room temperature for up to 60 min.
  • the mechanical processing step may alternatively or additionally comprise mechanical agitation of the substrate in a ball bearing hopper, e.g. at room temperature for up to 60 min. Exposing the substrate surface to UV light may e.g. be performed at room temperature for up to 60 min.
  • a bio-based cleaning solvent comprising a mixture of ethyl acetate and crude turpentine, wherein the ethyl acetate and crude turpentine mixture constitutes at least 95 vol.% of the bio-based solvent and wherein a ratio of ethyl acetate to crude turpentine in the bio-based solvent is varied between 5:95 to 95:5 vol.%.
  • the first sample was an aluminium profile with a powder coating on a surface thereof and the second sample was an aluminium plate with a plastic film coating on a surface thereof. Both samples were exposed to the solvent for 10 minutes at room temperature with added agitation through ultrasonication.
  • Three solvent mixture ratios of ethyl acetate:crude turpentine were investigated: 30:70; 50:50 and 70:30 vol.% (solvent comprised 100 vol.% of ethyl acetate and crude turpentine). The results are shown in Figs 1 and 2 , as well as in Table 1.
  • Fig. 1 shows optical microscopy pictures of the aluminium substrate surface with a powder coating (thickness of coating less than 1 mm) treated with a solvent comprising ethyl acetate and crude turpentine in (a) a ratio of 30:70 vol.%, in (b) a ratio of 50:50 vol.%, and in (c) a ratio of 70:30 vol.%. It was shown that the powder coating was disrupted and delaminated from the aluminium substrate when exposed to a solvent comprising a ratio of ethyl acetate to crude turpentine of 50:50 vol.%. At 70 vol.% ethyl acetate, complete delamination of the powder coating was observed. The coated film could easily be removed with tweezers from the aluminium substrate, as shown in (d) in Fig. 1 .
  • Fig. 2 shows optical microscopy pictures of the aluminium substrate surface plastic film coating (thickness 30-150 ⁇ m) treated with a solvent comprising ethyl acetate and crude turpentine in (a) a ratio of 30:70 vol.%, in (b) a ratio of 50:50 vol.%, and in (c) a ratio of 70:30 vol.%.
  • Exposed aluminium is seen for all samples treated with the solvent in the three detailed ratios, showing the efficacy of coating removal.
  • a reference untreated sample is shown (d) where the plastic film can be seen.
  • Residual total organic carbon content (TOC) (%), measured by a total organic carbon analyser, is shown in Table 1. The measurements showed that sample 1 and sample 2 were effectively cleaned of any carbon contaminants, as the residual total carbon content of the treated surfaces equals the total carbon content of the pristine reference aluminium sample.
  • Table 1 Sample ID Type of organic contaminant Treated with X:Y ratio Ethyl acetate:Crude Turpentine Total organic carbon (TOC) % Treated Untreated Aluminium 1 Powder coating 70:30 0.02 % 3.03 % Aluminium 2 Plastic film 70:30 0.01 % 0.98 % Reference, casted aluminium None - 0.01 %
  • the bio-based solvent comprising a mixture of ethyl acetate and crude turpentine could efficiently remove organic carbon contaminants from aluminium substrates by a mild exposure at room temperature for just 10 minutes under agitation. Most efficient operation was observed at higher ethyl acetate compositions (i.e. > 50%).

Landscapes

  • 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)
EP24175462.1A 2024-05-13 2024-05-13 Solvant de nettoyage d'origine biologique comprenant un mélange d'acétate d'éthyle et de térébenthine brute Pending EP4650428A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
EP24175462.1A EP4650428A1 (fr) 2024-05-13 2024-05-13 Solvant de nettoyage d'origine biologique comprenant un mélange d'acétate d'éthyle et de térébenthine brute
PCT/EP2025/062817 WO2025237856A1 (fr) 2024-05-13 2025-05-12 Solvant de nettoyage à base biologique comprenant un mélange d'acétate d'éthyle et de térébenthine brute

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
EP24175462.1A EP4650428A1 (fr) 2024-05-13 2024-05-13 Solvant de nettoyage d'origine biologique comprenant un mélange d'acétate d'éthyle et de térébenthine brute

Publications (1)

Publication Number Publication Date
EP4650428A1 true EP4650428A1 (fr) 2025-11-19

Family

ID=91076794

Family Applications (1)

Application Number Title Priority Date Filing Date
EP24175462.1A Pending EP4650428A1 (fr) 2024-05-13 2024-05-13 Solvant de nettoyage d'origine biologique comprenant un mélange d'acétate d'éthyle et de térébenthine brute

Country Status (2)

Country Link
EP (1) EP4650428A1 (fr)
WO (1) WO2025237856A1 (fr)

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2003055605A (ja) * 2001-08-15 2003-02-26 Fujii Yoshi Tsusho Kk 芳香族炭化水素を含まない塗料用溶剤
US8414797B2 (en) 2009-01-29 2013-04-09 Greensolve, Llc Solvent systems and methods of producing high flash point solvent systems including terpenes
CN104744406A (zh) * 2015-02-10 2015-07-01 广西民族大学 利用重质松节油制备环氧石竹烯及分离长叶烯的方法
CN106479753A (zh) * 2016-08-30 2017-03-08 成都市翻鑫家科技有限公司 一种环保清洗剂

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2003055605A (ja) * 2001-08-15 2003-02-26 Fujii Yoshi Tsusho Kk 芳香族炭化水素を含まない塗料用溶剤
US8414797B2 (en) 2009-01-29 2013-04-09 Greensolve, Llc Solvent systems and methods of producing high flash point solvent systems including terpenes
CN104744406A (zh) * 2015-02-10 2015-07-01 广西民族大学 利用重质松节油制备环氧石竹烯及分离长叶烯的方法
CN106479753A (zh) * 2016-08-30 2017-03-08 成都市翻鑫家科技有限公司 一种环保清洗剂

Also Published As

Publication number Publication date
WO2025237856A1 (fr) 2025-11-20

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