EP2687580B1 - Uhr - Google Patents

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Publication number
EP2687580B1
EP2687580B1 EP12177174.5A EP12177174A EP2687580B1 EP 2687580 B1 EP2687580 B1 EP 2687580B1 EP 12177174 A EP12177174 A EP 12177174A EP 2687580 B1 EP2687580 B1 EP 2687580B1
Authority
EP
European Patent Office
Prior art keywords
mol
add
water
dioxolane
elements
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.)
Active
Application number
EP12177174.5A
Other languages
English (en)
French (fr)
Other versions
EP2687580A1 (de
Inventor
Patrick EGGLI
Sylvain Huot-Marchand
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.)
Breitling AG
Original Assignee
Breitling AG
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Filing date
Publication date
Application filed by Breitling AG filed Critical Breitling AG
Priority to EP12177174.5A priority Critical patent/EP2687580B1/de
Publication of EP2687580A1 publication Critical patent/EP2687580A1/de
Application granted granted Critical
Publication of EP2687580B1 publication Critical patent/EP2687580B1/de
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
    • C10M105/08—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing oxygen
    • C10M105/18—Ethers, e.g. epoxides
    • G—PHYSICS
    • G04—HOROLOGY
    • G04B—MECHANICALLY-DRIVEN CLOCKS OR WATCHES; MECHANICAL PARTS OF CLOCKS OR WATCHES IN GENERAL; TIME PIECES USING THE POSITION OF THE SUN, MOON OR STARS
    • G04B31/00—Bearings; Point suspensions or counter-point suspensions; Pivot bearings; Single parts therefor
    • G04B31/08—Lubrication
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/04—Ethers; Acetals; Ortho-esters; Ortho-carbonates
    • C10M2207/046—Hydroxy ethers
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/06—Oiliness; Film-strength; Anti-wear; Resistance to extreme pressure
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/06—Instruments or other precision apparatus, e.g. damping fluids

Definitions

  • the present invention relates to the field of mechanical watchmaking. It relates more particularly to a timepiece comprising at least two elements in contact and relatively movable relative to each other, at least one of said elements having a contact surface with the other element which is lubricated by means of a lubricating composition.
  • the present invention also relates to such a lubricant composition, the use of chemical compounds as a lubricating agent and new chemical compounds.
  • a timepiece comprising at least two elements in contact and relatively movable relative to each other, it is necessary to lubricate the surfaces in contact with these elements to ensure as little friction as possible between these two elements.
  • lubricating oils comprising lubricants with a low coefficient of friction, less than or equal to 0.1.
  • a lubricating agent is, for example, mixtures of polyalphaolefin type synthetic oils associated with a glycerol ester, namely glycerol monooleate (GMO).
  • the lubricating oils used in the timepieces must be altered as little as possible and retain their lubricant properties for a generally accepted period of at least 4 years.
  • Such contact surfaces comprise at least one oxide layer on the surface, and are for example made of alumina or zirconia, and more particularly of ruby or sapphire, materials traditionally used in the watch industry for bearings or pallets of 'anchor.
  • the agent lubricant being a compound containing one or more hydrophilic groups chosen from C 3 -C 9 polyols having at least one third of OH groups relative to the number of carbon atoms.
  • a preferred compound is glycerol.
  • These compounds are agents with a very low coefficient of friction, the coefficients obtained being less than 0.06.
  • these compounds have the disadvantage of deteriorating over time. In particular, they promote the development of microorganisms that will degrade the lubricant composition but also promote corrosion of the parts of the watch.
  • oils used for the lubrication of timepieces are very fluid. Such oils have a natural tendency to migrate in case of deficient surface preparation. This migration would be catastrophic for the operation of the movement, so that these oils require the application of a layer of epilame, which complicates the steps of mounting a timepiece.
  • the present invention also relates to a lubricant composition according to the claims.
  • glycerol ethers have the advantage of making it possible to obtain lubricant compositions that are stable over time, while guaranteeing tribological properties equal to or greater than those of known lubricating compositions.
  • the present invention relates to a timepiece comprising at least two elements in contact and relatively movable relative to each other, at least one of said elements having a contact surface which is lubricated by means of a lubricating composition.
  • said lubricating composition comprises at least one glycerol ether chosen from the group comprising and their mixtures.
  • the contact surface of at least one of the two elements in contact may be metal, metal alloy or plastic. So, the contact surface of at least one of the two elements in contact may be ferrous or cuprous alloy and have a surface coating electrochemically deposited, chemical, plasma or other.
  • a surface tension modification layer preventing the spreading of the lubricant composition. It is also possible to perform diffusion treatments.
  • the contact surface of at least one of the two lubricated elements by means of a lubricating composition may exhibit affinity with hydrophilic groups.
  • the contact surface having an affinity with hydrophilic groups of at least one of the two elements is made of an oxide-based material.
  • an oxide may be chosen from the group comprising, for example, aluminum oxide and zirconium oxide.
  • the contact surface having an affinity with hydrophilic groups of at least one of the two elements is made of ruby or sapphire.
  • the counterpart may be a ferrous alloy, cuprous or other, coated or uncoated, treated or not.
  • the contact surface of each of the two elements has an affinity with hydrophilic groups, as defined above.
  • one of the elements of the timepiece is an anchor pallet and the other element is an escape wheel. It is also possible to advantageously lubricate a mobile axis (for example a wheel element or a pendulum) pivoting in a clock stone.
  • a mobile axis for example a wheel element or a pendulum
  • the lubricating composition also comprises all the necessary additives traditionally used in lubricating compositions, and in particular in lubricating compositions used in the field of horology.
  • the lubricating composition may comprise viscosity control agents, other complementary base oils, antioxidants, anti-wear and high-pressure additives and / or corrosion inhibitors.
  • the present invention also relates to the use as a lubricating agent in a lubricant composition for lubricating a contact surface of at least one element in contact with another element of a timepiece, said elements being relatively movable relative to one another. relative to the other, at least one glycerol ether as defined below, including their mixtures.
  • the present invention also relates to a chemical compound of formula:
  • isotridecanol into a flask. Add 0.01 mol of sodium metal and heat to 100 ° C. Once the sodium is completely dissolved, add 0.2 mol of 2,2-dimethyl-4-glycidyloxymethyl-1,3-dioxolane in 30 minutes at 100 ° C with stirring. Heat at this temperature for another 5 hours. Cool to room temperature, wash with 200 mL of water. Dry the organic phase over magnesium sulphate, filtered through buchner. 210 g of are obtained. The excess isotridecanol is separated by distillation, eb.
  • the lubricant is deposited in superabundant quantity.
  • the average coefficient of friction is measured over the first 10 meters.
  • the glycerol ethers are stable over time so that the lubricating composition according to the invention is not altered over time, unlike glycerol.
  • certain compounds used according to the invention have high viscosities at ambient temperature (consistency of a grease) and make it possible to formulate lubricating compositions with a high viscosity at ambient temperature (consistency of a grease). Consequently, the compounds used according to the invention make it possible not to use an epilame in order to prevent the spreading of the lubricating composition.
  • the Synt-A-Lube TM 9010 oil used in the comparative tribometric example, the 9415 grease used in the comparative watch example or the glycerol-based lubricating compositions are fluid or very fluid, so that require the use of an epilame.
  • the amplitude of a rocker lubricated by one of the lubricant compositions according to the invention is measured (conventional lubrication of the rock of pivoting of the balance shaft).
  • the amplitude of a balance wheel is also measured, the escapement having been lubricated by one of the lubricating compositions according to the invention (conventional lubrication of the teeth of the escape wheel).
  • the amplitudes are measured in degrees, the measurements being made on a representative sample of movements, with the same equipment.
  • Lubrication of the exhaust Lubricant Composition comprising a 50/50 mixture of compounds VII and X Moebius 9415 Average gain Horizontal 323 309 5% Vertical 311 290 7%
  • Lubrication of the balance Lubricant Composition comprising compound VII Composition comprising a 70/20 mixture of compounds VII and X Moebius 9010 Average gain Horizontal 316 318 310 2% Vertical 287 287 277 3%
  • the lubricating compositions according to the invention are therefore more advantageous than the known oils because they hold in place without resorting to an epilame, they do not deteriorate over time, while having tribological properties equal to or better than those of known oils. .

Landscapes

  • Chemical & Material Sciences (AREA)
  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Health & Medical Sciences (AREA)
  • Emergency Medicine (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Chemistry (AREA)
  • Lubricants (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Claims (4)

  1. Uhr, umfassend mindestens zwei Element in Kontakt und relativ zueinander beweglich, wobei mindestens eines der Elemente eine Kontaktfläche mit dem anderen Element aufweist, die mit einer schmierenden Zusammensetzung geschmiert wird, dadurch gekennzeichnet, dass die schmierende Zusammensetzung mindestens einen Glycerinether umfasst, der aus der Gruppe ausgewählt ist, die umfasst
    Figure imgb0033
    Figure imgb0034
    Figure imgb0035
    Figure imgb0036
    Figure imgb0037
    Figure imgb0038
    Figure imgb0039
     und deren Gemische.
  2. Uhr nach vorangehendem Anspruch, dadurch gekennzeichnet, dass eines der Elemente eine Ankerpalette und das andere Element ein Hemmungsrad ist.
  3. Verwendung als Schmiermittel in einer schmierenden Zusammensetzung, um eine Kontaktfläche mindestens eines Elements im Kontakt mit einem anderen Element einer Uhr zu schmieren, wobei die Elemente relativ zueinander beweglich sind, mindestens eines Glycerinethers, der aus der Gruppe ausgewählt ist, die umfasst
    Figure imgb0040
    Figure imgb0041
    Figure imgb0042
    Figure imgb0043
    Figure imgb0044
    Figure imgb0045
    Figure imgb0046
     und deren Gemischen.
  4. Chemische Verbindung der Formel
    Figure imgb0047
EP12177174.5A 2012-07-19 2012-07-19 Uhr Active EP2687580B1 (de)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP12177174.5A EP2687580B1 (de) 2012-07-19 2012-07-19 Uhr

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
EP12177174.5A EP2687580B1 (de) 2012-07-19 2012-07-19 Uhr

Publications (2)

Publication Number Publication Date
EP2687580A1 EP2687580A1 (de) 2014-01-22
EP2687580B1 true EP2687580B1 (de) 2018-04-11

Family

ID=46651385

Family Applications (1)

Application Number Title Priority Date Filing Date
EP12177174.5A Active EP2687580B1 (de) 2012-07-19 2012-07-19 Uhr

Country Status (1)

Country Link
EP (1) EP2687580B1 (de)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2017003634A1 (en) * 2015-06-30 2017-01-05 Exxonmobil Chemical Patents Inc. Lubricant compositions comprising diol functional groups and methods of making and using same
EP3192853B1 (de) * 2016-01-15 2023-04-26 Sikemia Oberflächenbehandlungsverfahren zum erzeugen einer oleophoben und/oder hydrophoben beschichtung
KR20190140474A (ko) * 2017-05-09 2019-12-19 닛산 가가쿠 가부시키가이샤 에폭시 화합물의 제조방법

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20040018948A1 (en) * 2002-07-17 2004-01-29 Unilever Home & Personal Care Usa, Division Of Conopco, Inc. Skin care cosmetic methods of sebum control using carboxyalkylates of branched alcohols and/or alkoxylates thereof
CN102031178A (zh) * 2010-12-24 2011-04-27 淄博德丰化工有限公司 低硫柴油润滑性添加剂及其制备方法
US20110105439A1 (en) * 2008-07-31 2011-05-05 Kao Corporation Ceramide Production Promoter
US20110308426A1 (en) * 2009-03-24 2011-12-22 E.I. Du Pont De Nemours And Company Pigmented inkjet ink comprising a bleed control agent
WO2012080682A1 (fr) * 2010-12-17 2012-06-21 Fonds De Developpement Des Filieres Des Oleagineux Et Proteagineux Fidop Procede de preparation d'ether de polyol

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4659772A (en) * 1983-09-27 1987-04-21 Union Carbide Corporation Novel polymer/polyols and uses thereof
US20060183652A1 (en) * 2004-12-10 2006-08-17 Takashi Fujitsu Lubricating oil composition
EP2082014B1 (de) 2006-11-02 2018-02-14 Rolex Sa Watch

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20040018948A1 (en) * 2002-07-17 2004-01-29 Unilever Home & Personal Care Usa, Division Of Conopco, Inc. Skin care cosmetic methods of sebum control using carboxyalkylates of branched alcohols and/or alkoxylates thereof
US20110105439A1 (en) * 2008-07-31 2011-05-05 Kao Corporation Ceramide Production Promoter
US20110308426A1 (en) * 2009-03-24 2011-12-22 E.I. Du Pont De Nemours And Company Pigmented inkjet ink comprising a bleed control agent
WO2012080682A1 (fr) * 2010-12-17 2012-06-21 Fonds De Developpement Des Filieres Des Oleagineux Et Proteagineux Fidop Procede de preparation d'ether de polyol
CN102031178A (zh) * 2010-12-24 2011-04-27 淄博德丰化工有限公司 低硫柴油润滑性添加剂及其制备方法

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