EP2196562A1 - Compositions pour dégraisser des surfaces dures - Google Patents

Compositions pour dégraisser des surfaces dures Download PDF

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Publication number
EP2196562A1
EP2196562A1 EP08021577A EP08021577A EP2196562A1 EP 2196562 A1 EP2196562 A1 EP 2196562A1 EP 08021577 A EP08021577 A EP 08021577A EP 08021577 A EP08021577 A EP 08021577A EP 2196562 A1 EP2196562 A1 EP 2196562A1
Authority
EP
European Patent Office
Prior art keywords
hydroxyl
stands
degreasing
acetals
carbon atoms
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.)
Withdrawn
Application number
EP08021577A
Other languages
German (de)
English (en)
Inventor
Joaquin Bigorra Llosas
Carles Estevez
Lidia Galiá
Josep Castells
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.)
Cognis IP Management GmbH
Institut Universitari de Ciencia i Tecnologia
Institut Univ De Ciencia I Technologia SA
Original Assignee
Cognis IP Management GmbH
Institut Universitari de Ciencia i Tecnologia
Institut Univ De Ciencia I Technologia SA
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 Cognis IP Management GmbH, Institut Universitari de Ciencia i Tecnologia, Institut Univ De Ciencia I Technologia SA filed Critical Cognis IP Management GmbH
Priority to EP08021577A priority Critical patent/EP2196562A1/fr
Publication of EP2196562A1 publication Critical patent/EP2196562A1/fr
Withdrawn legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C23—COATING 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
    • C23G—CLEANING OR DE-GREASING OF METALLIC MATERIAL BY CHEMICAL METHODS OTHER THAN ELECTROLYSIS
    • C23G5/00—Cleaning or de-greasing metallic material by other methods; Apparatus for cleaning or de-greasing metallic material with organic solvents
    • C23G5/02—Cleaning or de-greasing metallic material by other methods; Apparatus for cleaning or de-greasing metallic material with organic solvents using organic solvents
    • C23G5/032—Cleaning or de-greasing metallic material by other methods; Apparatus for cleaning or de-greasing metallic material with organic solvents using organic solvents containing oxygen-containing compounds
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D7/00—Compositions of detergents based essentially on non-surface-active compounds
    • C11D7/22—Organic compounds
    • C11D7/26—Organic compounds containing oxygen
    • C11D7/264—Aldehydes; Ketones; Acetals or ketals
    • 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
    • C11D7/267—Heterocyclic compounds

Definitions

  • the present invention is related to the area of metal treatment and refers to new degreasing compositions, a method for degreasing hard surfaces and the use of green solvents for degreasing operations.
  • chlorinated solvents such as trichloroethanol, chloroform, methyl chloride, CFC-113, HFCs, HCFCs, CO 2 jets, scCO 2 semi-aqueous solvents, alkaline cleaning agents, emulsifying detergent-based cleaners, and aliphatic hydrocarbon based solvents and azeotropic mixtures have been proposed to replace the widely used current industrial standard, namely trichloroethylene.
  • trichloroethanol chloroform
  • methyl chloride CFC-113
  • HFCs HCFCs
  • CO 2 jets scCO 2 semi-aqueous solvents
  • alkaline cleaning agents alkaline cleaning agents
  • emulsifying detergent-based cleaners emulsifying detergent-based cleaners
  • aliphatic hydrocarbon based solvents and azeotropic mixtures have been proposed to replace the widely used current industrial standard, namely trichloroethylene.
  • none of the proposed alternatives fully satisfy the key industrial needs of the metal finishing sector.
  • the object of the present invention has been to develop new compositions allowing to perform metal degreasing operations in highly variable settings, with metal parts of different size and shape, minimizing diffuse emission, release of contaminated air during loading and unloading, and solvent release from cleaned metal parts.
  • the use of these compositions should also avoid the generation of large waste streams, allowing to establish an easy and cost effective process in order to recycle solvent and rinsing water and ultimately delivering parts adequately conditioned for immediate use in subsequent steps of the metal finishing process.
  • the present invention intends to replace commercial degreasing solvents known from the market by new compositions being more efficient, safer and friendlier to the environment.
  • the present invention refers to new degreasing compositions comprising at least one glycerol acetal or ketal according to general formula (Ia) or (Ib) in which R 1 stands for hydrogen or an hydroxyl group, and R 2 and R 3 independently from each other mean hydrogen, an hydrocarbon radical having 1 to 22 carbon atoms, and 0 or up to 3 double bonds - optionally substituted by an amine, hydroxyl, phenyl or hydroxyphenyl group.
  • R 1 stands for hydrogen or an hydroxyl group
  • R 2 and R 3 independently from each other mean hydrogen, an hydrocarbon radical having 1 to 22 carbon atoms, and 0 or up to 3 double bonds - optionally substituted by an amine, hydroxyl, phenyl or hydroxyphenyl group.
  • Another object of the present invention relates to a method for the degreasing of hard surfaces, characterised in that said surfaces are brought into contact with at least one organic solvent selected from the group consisting of glycerol acetals or ketals according to general formula (Ia) or (Ib) in which R 1 stands for hydrogen or an hydroxyl group, and R 2 and R 3 independently from each other mean hydrogen, an hydrocarbon radical having 1 to 22 carbon atoms, and 0 or up to 3 double bonds - optionally substituted by an amine, hydroxyl, phenyl or hydroxyphenyl group.
  • organic solvent selected from the group consisting of glycerol acetals or ketals according to general formula (Ia) or (Ib) in which R 1 stands for hydrogen or an hydroxyl group, and R 2 and R 3 independently from each other mean hydrogen, an hydrocarbon radical having 1 to 22 carbon atoms, and 0 or up to 3 double bonds - optionally substituted by an amine, hydroxyl, phenyl or
  • Acetals and ketals are obtained by condensation of alcohols and aldehydes or ketones respectively.
  • the alcohol is a diol the formation of cyclic, 6-membered or 5-membered structures takes place.
  • acetals or ketals are those obtained from the condensation of glycerol, 1-2,propandiol or 1,3-propandiol with lower aldehydes like for example formalin, acetaldehyde, propanal, butanal, pentanal, or fatty aldehydes comprising 6 to 22 carbon atoms, like capronal, laurylaldehyde, myristylaldehyde, palmitylaldehyde, stearylaldehyde, oleyl aldehyde, behenyl aldehyde, erucylaldehyde and the like.
  • lower aldehydes like for example formalin, acetaldehyde, propanal, butanal, pentanal, or fatty aldehydes comprising 6 to 22 carbon atoms, like capronal, laurylaldehyde, myristylaldehyde, palmitylaldehyde
  • Suitable ketals are obtained from lower aliphatic ketones like for example acetone or fatty ketones like distearyl ketone.
  • the preferred products are glycerol acetals, in particular those obtained from aliphatic aldehydes having 1 to 6 carbon atoms, more in particular the ones with 3 to 6 carbon atoms like glycerol propanal or glycerol iso-butyral.
  • the hard surfaces represent metal surfaces, such as those used in the manufacture of automotive and building components.
  • the glycerol acetals or ketals which are used as so-called “green solvents” serve as degreasing agents in order to remove all greases and stains, in particular the preservatives from the surfaces. This can be done either by tipping the parts into the solvent or - more convenient - by spraying. Once degreasing has taken place, the acetals or ketals are collected and reused several times without purification.
  • glycerol acetals and ketals show excellent performance in removing stains, grease and especially preservatives from hard surfaces.
  • Another object of the present invention is therefore directed to the use of glycerol acetals or ketals according to general formula (Ia) or (Ib) in which R 1 stands for hydrogen or an hydroxyl group, and R 2 and R 3 independently from each other mean hydrogen, an hydrocarbon radical having 1 to 22 carbon atoms, and 0 or up to 3 double bonds - optionally substituted by an amine, hydroxyl, phenyl or hydroxyphenyl group, as degreasing agents for hard surfaces.
  • R 1 stands for hydrogen or an hydroxyl group
  • R 2 and R 3 independently from each other mean hydrogen, an hydrocarbon radical having 1 to 22 carbon atoms, and 0 or up to 3 double bonds - optionally substituted by an amine, hydroxyl, phenyl or hydroxyphenyl group, as degreasing agents for hard surfaces.
  • the degreasing process consists of the following phases:
  • the solvent can be reused several times without loss of efficacy. At the end of its useful life, the solvent can be recycled by distillation with yields higher than 80%.
  • Figure 1 shows the fundamental aspects of the degreasing process.
  • Removal Efficacy measures the degree of removal of organic materials (grease and/or solvent) from the surface of metal parts.
  • Removal efficacy screening test remove the grease of ten metallic greased pieces by degreasing process. The standard procedure was done by bringing the solvent into contact with the metal surface, more particular by immersion without agitation during 10 minutes in one volume of fresh solvent followed by three consecutive washing cycles by immersion in clean water. The amount of organic material (grease and/or solvent) that was not eliminated by the assayed procedure was determined by direct weight after removal of organic residues from the metallic parts by standard cleaning procedure with trichloroethylene.

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  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Emergency Medicine (AREA)
  • General Chemical & Material Sciences (AREA)
  • Materials Engineering (AREA)
  • Mechanical Engineering (AREA)
  • Metallurgy (AREA)
  • Detergent Compositions (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
EP08021577A 2008-12-12 2008-12-12 Compositions pour dégraisser des surfaces dures Withdrawn EP2196562A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP08021577A EP2196562A1 (fr) 2008-12-12 2008-12-12 Compositions pour dégraisser des surfaces dures

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
EP08021577A EP2196562A1 (fr) 2008-12-12 2008-12-12 Compositions pour dégraisser des surfaces dures

Publications (1)

Publication Number Publication Date
EP2196562A1 true EP2196562A1 (fr) 2010-06-16

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ID=40556005

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EP08021577A Withdrawn EP2196562A1 (fr) 2008-12-12 2008-12-12 Compositions pour dégraisser des surfaces dures

Country Status (1)

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EP (1) EP2196562A1 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2013539487A (ja) * 2010-08-12 2013-10-24 セゲティス インコーポレーテッド カルボキシエステルケタール除去組成物、それらの製造方法及びそれらの使用
US20150113860A1 (en) * 2012-04-06 2015-04-30 Eni S.P.A. Fuel compositions comprising hydrophobic derivatives of glycerine

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH06346093A (ja) * 1993-06-08 1994-12-20 Kao Corp 洗浄剤組成物
EP1905767A1 (fr) * 2006-09-28 2008-04-02 Cognis IP Management GmbH Procédé de préparation des acétals de la glycérine

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH06346093A (ja) * 1993-06-08 1994-12-20 Kao Corp 洗浄剤組成物
EP1905767A1 (fr) * 2006-09-28 2008-04-02 Cognis IP Management GmbH Procédé de préparation des acétals de la glycérine

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
SOKOLOWSKI A ET AL: "ACETALS AND EHTERS. 11. SOLUBILITY OF ALKYL-SUBSTITUTED 1,3-DIOXOLANES AND 1,3-DIOXANES IN WATER", JOURNAL OF PHYSICAL CHEMISTRY, AMERICAN CHEMICAL SOCIETY, US, vol. 88, no. 4, 16 February 1984 (1984-02-16), pages 807 - 809, XP000646189, ISSN: 0022-3654 *

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2013539487A (ja) * 2010-08-12 2013-10-24 セゲティス インコーポレーテッド カルボキシエステルケタール除去組成物、それらの製造方法及びそれらの使用
EP2603836A4 (fr) * 2010-08-12 2017-08-02 Segetis, Inc. Compositions d'élimination à base de carboxy ester cétal, procédés de fabrication et utilisations associées
US20150113860A1 (en) * 2012-04-06 2015-04-30 Eni S.P.A. Fuel compositions comprising hydrophobic derivatives of glycerine

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