EP0533552A1 - Lubricating and desinfecting solution for containers conveyor chain the food industry and process for its use - Google Patents

Lubricating and desinfecting solution for containers conveyor chain the food industry and process for its use Download PDF

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Publication number
EP0533552A1
EP0533552A1 EP92402521A EP92402521A EP0533552A1 EP 0533552 A1 EP0533552 A1 EP 0533552A1 EP 92402521 A EP92402521 A EP 92402521A EP 92402521 A EP92402521 A EP 92402521A EP 0533552 A1 EP0533552 A1 EP 0533552A1
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EP
European Patent Office
Prior art keywords
etheramine
lubricant
water
solution according
acid
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.)
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Application number
EP92402521A
Other languages
German (de)
French (fr)
Other versions
EP0533552B1 (en
Inventor
Joseph Schapira
Jacques Vincent
Jean-Claude Gamet
Catherine Geneix
Brigitte Caire
Christian Boiziau
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.)
Compagnie Francaise de Produits Industriels SA
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Compagnie Francaise de Produits Industriels SA
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    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M173/00Lubricating compositions containing more than 10% water
    • C10M173/02Lubricating compositions containing more than 10% water not containing mineral or fatty oils
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M125/00Lubricating compositions characterised by the additive being an inorganic material
    • C10M125/18Compounds containing halogen
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    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M125/00Lubricating compositions characterised by the additive being an inorganic material
    • C10M125/24Compounds containing phosphorus, arsenic or antimony
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    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M129/00Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen
    • C10M129/02Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen having a carbon chain of less than 30 atoms
    • C10M129/04Hydroxy compounds
    • C10M129/06Hydroxy compounds having hydroxy groups bound to acyclic or cycloaliphatic carbon atoms
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    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M129/00Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen
    • C10M129/02Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen having a carbon chain of less than 30 atoms
    • C10M129/16Ethers
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    • C10M129/00Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen
    • C10M129/02Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen having a carbon chain of less than 30 atoms
    • C10M129/26Carboxylic acids; Salts thereof
    • C10M129/28Carboxylic acids; Salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M129/30Carboxylic acids; Salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having 7 or less carbon atoms
    • C10M129/32Carboxylic acids; Salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having 7 or less carbon atoms monocarboxylic
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    • C10M129/00Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen
    • C10M129/02Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen having a carbon chain of less than 30 atoms
    • C10M129/26Carboxylic acids; Salts thereof
    • C10M129/28Carboxylic acids; Salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M129/30Carboxylic acids; Salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having 7 or less carbon atoms
    • C10M129/36Carboxylic acids; Salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having 7 or less carbon atoms containing hydroxy groups
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    • C10M129/02Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen having a carbon chain of less than 30 atoms
    • C10M129/26Carboxylic acids; Salts thereof
    • C10M129/28Carboxylic acids; Salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M129/38Carboxylic acids; Salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having 8 or more carbon atoms
    • C10M129/40Carboxylic acids; Salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having 8 or more carbon atoms monocarboxylic
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    • C10M129/02Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen having a carbon chain of less than 30 atoms
    • C10M129/26Carboxylic acids; Salts thereof
    • C10M129/48Carboxylic acids; Salts thereof having carboxyl groups bound to a carbon atom of a six-membered aromatic ring
    • C10M129/50Carboxylic acids; Salts thereof having carboxyl groups bound to a carbon atom of a six-membered aromatic ring monocarboxylic
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    • C10M133/02Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of less than 30 atoms
    • C10M133/04Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M133/06Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M133/08Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups
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    • C10M145/00Lubricating compositions characterised by the additive being a macromolecular compound containing oxygen
    • C10M145/18Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M145/24Polyethers
    • C10M145/26Polyoxyalkylenes
    • C10M145/36Polyoxyalkylenes etherified
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    • C10M2201/02Water
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    • C10M2201/08Inorganic acids or salts thereof
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    • C10M2201/08Inorganic acids or salts thereof
    • C10M2201/081Inorganic acids or salts thereof containing halogen
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    • C10M2201/08Inorganic acids or salts thereof
    • C10M2201/082Inorganic acids or salts thereof containing nitrogen
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    • C10M2201/08Inorganic acids or salts thereof
    • C10M2201/084Inorganic acids or salts thereof containing sulfur, selenium or tellurium
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    • C10M2201/085Phosphorus oxides, acids or salts
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    • C10M2207/02Hydroxy compounds
    • C10M2207/021Hydroxy compounds having hydroxy groups bound to acyclic or cycloaliphatic carbon atoms
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    • C10M2207/121Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of seven or less carbon atoms
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    • C10M2207/122Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of seven or less carbon atoms monocarboxylic
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    • C10M2207/10Carboxylix acids; Neutral salts thereof
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    • C10M2207/10Carboxylix acids; Neutral salts thereof
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    • C10M2207/125Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of eight up to twenty-nine carbon atoms, i.e. fatty acids
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    • C10N2050/00Form in which the lubricant is applied to the material being lubricated
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    • C10N2070/00Specific manufacturing methods for lubricant compositions
    • C10N2070/02Concentrating of additives

Definitions

  • the subject of the invention is a lubricating and disinfecting solution for a container conveyor chain in the food industry.
  • the solution according to the invention is more particularly intended for the lubrication of conveyor chains for bottles, or other packaging for packaging, in the beverage industries, such as, for example, breweries, mineral waters, fruit juices or wine.
  • bottles or other containers are transported, before or after filling, on chains, most of which are made of stainless steel. These chains are treated, continuously or in sequence, with lubricating solutions.
  • the lubrication thus obtained makes it possible, in the case of conveying bottles, to reach high rates on packaging installations, namely up to 80,000 bottles per hour or more.
  • This type of solution can also, by its nature, become on the chains an excellent substrate for the growth of bacteria or other microorganisms, and there is often a development, between the links and below the chains of vases or "slimes" making the above-mentioned cleanings doubly necessary which are not always easy to carry out.
  • EP-A-0 372 628 and EP-A-0 384 282 which recommend the use in solutions of the kind in question of fatty alkylamines for the first and d 'secondary and / or tertiary amines for the second.
  • anionic or nonionic surfactants has been recommended in European patent application EP-A-0 044 458 to avoid the formation of calcium soap.
  • the lubricating and disinfecting solution according to the invention is characterized in that it comprises an effective amount of at least one etheramine of formulas: RO- (CH2) 3-NH2 (1) or RO- (CH2) 3-NH (CH2) 3-NH2 (2) in which R represents an alkyl chain, saturated or unsaturated, branched at C6 to C21.
  • the lubrication and disinfection process for a container conveyor chain in the food industry is characterized by the fact that a lubricant and disinfectant solution according to the invention is applied to a conveyor chain in the food industry.
  • a lubricant and disinfectant solution according to the invention is applied to a conveyor chain in the food industry.
  • the etheramine of formula (1) or (2) is completely or partially neutralized up to a pH of 5 to 9, preferably 6 to 8, using an organic acid chosen from the group comprising acetic, hydroxyacetic acids , gluconic, lactic, benzoic, C8 to C20 fatty acids, such as coconut fatty acid or oleic acid, or using a mineral acid chosen from the group comprising phosphoric and hydrochloric acids; preferably, the neutralization is carried out using acetic acid or gluconic acid.
  • the solution according to the invention comprises a surfactant, preferably nonionic, chosen from non-foaming or low foaming products.
  • Such an agent improves the cleaning efficiency of the solution at the same time as it facilitates the formulation.
  • the solution according to the invention comprises, to facilitate the formulation but also to improve the aging behavior, a water-soluble solvent chosen from alcohols with a short chain from C1 to C8 and, preferably, from C2 or C3, in particular ethanol, n-propanol or isopropanol and the glycol ethers of the group comprising the methyl, ethyl, butyl or phenyl ethers of propylene- or dipropylene- or tripropylene glycol, as well as same ethers of ethylene- or diethylene glycol, in particular those known under the trademarks NAPSOL (BP Chemicals) and DOWANOL (Dow Chemical).
  • a water-soluble solvent chosen from alcohols with a short chain from C1 to C8 and, preferably, from C2 or C3, in particular ethanol, n-propanol or isopropanol and the glycol ethers of the group comprising the methyl, ethyl, butyl or phenyl ethers of prop
  • the solution according to the invention comprises disinfectant additives active with regard to particular bacterial strains, agents modifying the viscosity of the solution and dyes.
  • the solution according to the invention prepared at a concentration of 0.2 to 1% by volume, contains at least one etheramine of formula (1) and / or (2) as well as optionally a surfactant and a water-soluble solvent.
  • E, F, G, M The bactericidal efficacy was confirmed in the presence of hard water for four other solutions in accordance with the invention (E, F, G, M) and the results are collated in Table II below.
  • E F G H Isotridecyloxypropylamine (TOMAH PA 17) 10 10 10 15 80% acetic acid 2.6 3.2 3.1 4.6 Ethylene glycol butyl ether 5 5 5 5 5 5 5 5 5 5 5 5 5 5 Tridecyl alcohol 10 OE (LAUROXAL 10 from Witco Chemical) 4 - - 4 Lauric alcohol 20 OE (REMCOPAL 20 from Gerland) - - 4 - Water - - qs 100 - pH as 8.0 6.0 6.0 6.0 Efficiency on E. Coli in hard water at 30 ° TH (AFNOR NF T72 171 standard) 0.25% 0.25% 0.25% ⁇ 0.1%
  • the "glide” provided by the lubricating solutions was measured on a stainless steel pilot chain advancing at a rate of 0.33 m / s and with the aid of which the slip resistance expressed by an index I, d is evaluated.
  • '' a train of six bottles (one liter glass bottles filled with water).
  • the six bottles whose behavior is examined are attached to each other by a rope connected to a dynamometer, itself connected to a plotter and a digital sensor, for example of the brand SEDEME.
  • the index I is a number without unit and which has meaning only in comparison with lubrication with water alone.
  • the index is equal to zero when no traction is exerted on the dynamometer; at this time, the sensor is set to zero.
  • test was carried out on the one hand, a solution according to the prior art (Ref. 3) and, on the other hand, on the solutions according to the invention identified above, namely C, D, F , G and H, the solution Ref. 3 and the solutions according to the invention being at a concentration of 0.6% in water.
  • compositions in accordance with the invention have performances equivalent to those of known solutions based on soap.
  • the COD expressed in mg of oxygen per liter was determined for two solutions at 1% by weight in water, obtained from a concentrate in accordance with the invention, on the one hand, and of a concentrate according to the prior art based on soap, on the other hand.

Abstract

Lubricating and disinfecting solution for a receptacle conveyor line in the agri-foodstuffs industry, characterised in that it comprises an effective quantity of at least one ether amine of formulae: R-O-(CH2)3-NH2 (1> or RO-(CH2)3-NH(CH2)3-NH2 (2> in which R denotes a C6-C21 branched, saturated or unsaturated alkyl chain.

Description

L'invention a pour objet une solution lubrifiante et désinfectante pour chaîne transporteuse de récipients dans l'industrie agro-alimentaire.The subject of the invention is a lubricating and disinfecting solution for a container conveyor chain in the food industry.

Elle vise également le procédé pour la mise en oeuvre de cette solution et le concentré à partir duquel elle est préparée.It also relates to the process for the implementation of this solution and the concentrate from which it is prepared.

La solution selon l'invention est plus particulièrement destinée à la lubrification de chaînes transporteuses de bouteilles, ou autres emballages de conditionnement, dans les industries de la boisson, comme par exemple les brasseries, les eaux minérales, les jus de fruits ou le vin.The solution according to the invention is more particularly intended for the lubrication of conveyor chains for bottles, or other packaging for packaging, in the beverage industries, such as, for example, breweries, mineral waters, fruit juices or wine.

Dans les industries en question, les bouteilles ou autres contenants sont transportés, avant ou après remplissage, sur des chaînes dont la plupart sont en acier inoxydable. Ces chaînes sont traitées, en continu ou par séquences, par des solutions lubrifiantes.In the industries in question, bottles or other containers are transported, before or after filling, on chains, most of which are made of stainless steel. These chains are treated, continuously or in sequence, with lubricating solutions.

Ces solutions sont en général obtenues à partir de concentrés, par dilution avec de l'eau jusqu'à de faibles concentrations, de l'ordre de 0,2 à 1% en poids; elles sont appliquées par l'intermédiaire d'un ensemble de buses de pulvérisation sur toutes les chaînes de l'installation.These solutions are generally obtained from concentrates, by dilution with water to low concentrations, of the order of 0.2 to 1% by weight; they are applied via a set of spray nozzles to all the chains in the installation.

La lubrification ainsi obtenue permet, dans le cas de convoyage de bouteilles, d'atteindre des cadences importantes sur les installations de conditionnement, à savoir jusqu'à 80 000 bouteilles par heure ou plus.The lubrication thus obtained makes it possible, in the case of conveying bottles, to reach high rates on packaging installations, namely up to 80,000 bottles per hour or more.

Certaines des solutions déjà connues sont à base de savons, de potassium ou autres, et sont sensibles à la dureté de l'eau; une quantité insuffisante de séquestrant dans leur solution entraîne une formation de savon de calcium qui finit par obstruer les canalisations amenant la solution de lubrifiant; par conséquent, le savon de calcium formé nuit à la glisse des bouteilles, rendant obligatoires de fréquents nettoyages.Some of the solutions already known are based on soaps, potassium or others, and are sensitive to the hardness of water; an insufficient quantity of sequestrant in their solution leads to the formation of calcium soap which eventually clogs the pipes bringing the lubricant solution; therefore, the soap calcium formed interferes with the sliding of the bottles, making frequent cleaning compulsory.

Ce type de solution peut aussi, de par sa nature, devenir sur les chaînes un excellent substrat pour la croissance de bactéries ou autres microorganismes, et on assiste souvent à un développement, entre les maillons et en dessous des chaînes de vases ou "slimes" rendant doublement nécessaires les susdits nettoyages qui ne sont pas toujours faciles à réaliser.This type of solution can also, by its nature, become on the chains an excellent substrate for the growth of bacteria or other microorganisms, and there is often a development, between the links and below the chains of vases or "slimes" making the above-mentioned cleanings doubly necessary which are not always easy to carry out.

L'évolution vers une meilleure hygiène dans les industries agro-alimentaires et notamment dans le domaine de la boisson a conduit à la mise au point de solutions du genre en question dispensant des fréquents nettoyages et permettant d'empêcher la prolifération de microorganismes.The trend towards better hygiene in the food industry and in particular in the beverage sector has led to the development of solutions of the kind in question providing frequent cleaning and making it possible to prevent the proliferation of microorganisms.

On peut citer, à cet égard, les demandes de brevet européen EP-A-0 372 628 et EP-A-0 384 282 qui préconisent la mise en oeuvre dans les solutions du genre en question d'alkylamines grasses pour la première et d'amines secondaires et/ou tertiaires pour la seconde.We can cite, in this regard, European patent applications EP-A-0 372 628 and EP-A-0 384 282 which recommend the use in solutions of the kind in question of fatty alkylamines for the first and d 'secondary and / or tertiary amines for the second.

L'utilisation d'agents tensio-actifs anioniques ou non ioniques a été préconisée dans la demande de brevet européen EP-A- 0 044 458 pour éviter la formation de savon de calcium.The use of anionic or nonionic surfactants has been recommended in European patent application EP-A-0 044 458 to avoid the formation of calcium soap.

Pour tenir compte des exigences toujours croissantes des utilisateurs, la Société Demanderesse a poursuivi ses recherches en vue de la mise au point d'une solution du genre en question répondant encore mieux que celles qui existent déjà à l'ensemble des desiderata de la pratique selon lesquels les arrêts de la chaîne transporteuse pour des nettoyages doivent être réduits au strict minimum, voire supprimés et la prolifération microbienne doit être totalement contrôlée.In order to take account of the ever increasing requirements of users, the Applicant Company has continued its research with a view to developing a solution of the kind in question which meets even better than those which already exist for all the requirements of the practice according to which stops the conveyor chain for cleaning must be reduced to the absolute minimum, or even eliminated and microbial growth must be fully controlled.

Et elle a eu le mérite de trouver qu'il était possible d'atteindre ce but, c'est-à-dire de réaliser simultanément les opérations de lubrification et de désinfection des chaînes transporteuses, notamment sans phénomènes de bouchage, d'empêcher ainsi le développement de "slimes", de limiter au maximum le nombre d'opérations de nettoyages intermédiaires et d'autoriser de par les performances de glisse obtenues des cadences importantes, dès lors que l'on a recours, dans les solution et procédé du genre en question, à une quantité efficace d'étheramine aliphatique de formules:

        R-O-(CH₂)₃-NH₂   (1)


ou

        RO-(CH₂)₃-NH(CH₂)₃-NH₂   (2)


dans lesquelles R représente une chaîne alkyle, saturée ou insaturée, ramifiée en C₆ à C₂₁.
And it had the merit of finding that it was possible to achieve this goal, that is to say to simultaneously carry out the operations of lubrication and disinfection of the conveyor chains, in particular without phenomena clogging, thus preventing the development of "slimes", limiting as much as possible the number of intermediate cleaning operations and authorizing, by virtue of the sliding performance obtained at high rates, as soon as use is made, in solutions and processes of the kind in question, to an effective amount of aliphatic etheramine of formulas:

RO- (CH₂) ₃-NH₂ (1)


or

RO- (CH₂) ₃-NH (CH₂) ₃-NH₂ (2)


in which R represents an alkyl chain, saturated or unsaturated, branched at C₆ to C₂₁.

Par conséquent, la solution lubrifiante et désinfectante conforme à l'invention est caractérisée par le fait qu'elle comporte une quantité efficace d'au moins une étheramine de formules:

        R-O-(CH₂)₃-NH₂   (1)


ou

        RO-(CH₂)₃-NH(CH₂)₃-NH₂   (2)


dans lesquelles R représente une chaîne alkyle, saturée ou insaturée, ramifiée en C₆ à C₂₁.
Consequently, the lubricating and disinfecting solution according to the invention is characterized in that it comprises an effective amount of at least one etheramine of formulas:

RO- (CH₂) ₃-NH₂ (1)


or

RO- (CH₂) ₃-NH (CH₂) ₃-NH₂ (2)


in which R represents an alkyl chain, saturated or unsaturated, branched at C₆ to C₂₁.

Le procédé de lubrification et de désinfection pour chaîne transporteuse de récipients dans l'industrie agroalimentaire est caractérisé par le fait que l'on applique, sur une chaîne transporteuse dans l'industrie agro-alimentaire, une solution lubrifiante et désinfectante conforme à l'invention comportant une quantité efficace d'au moins une étheramine de formules:

        R-O-(CH₂)₃-NH₂   (1)


ou

        RO-(CH₂)₃-NH(CH₂)₃-NH₂   (2)


dans lesquelles R représente une chaîne alkyle, saturée ou insaturée, ramifiée en C₆ à C₂₁.
The lubrication and disinfection process for a container conveyor chain in the food industry is characterized by the fact that a lubricant and disinfectant solution according to the invention is applied to a conveyor chain in the food industry. comprising an effective amount of at least one etheramine of formulas:

RO- (CH₂) ₃-NH₂ (1)


or

RO- (CH₂) ₃-NH (CH₂) ₃-NH₂ (2)


in which R represents an alkyl chain, saturated or unsaturated, branched at C₆ to C₂₁.

Selon un mode de réalisation avantageux de la solution conforme à l'invention, l'étheramine de formule (1) ou (2), en vue d'améliorer sa solubilité dans l'eau ainsi que ses propriétés lubrifiantes et désinfectantes, est neutralisée en totalité ou partiellement jusqu'à un pH de 5 à 9, de préférence de 6 à 8, à l'aide d'un acide organique choisi dans le groupe comprenant les acides acétique, hydroxyacétique, gluconique, lactique, benzoïque, les acides gras en C₈ à C₂₀, tels que l'acide gras de coprah ou l'acide oléique, ou à l'aide d'un acide minéral choisi dans le groupe comprenant les acides phosphorique et chlorhydrique; de préférence, la neutralisation est réalisée à l'aide de l'acide acétique ou de l'acide gluconique.According to an advantageous embodiment of the solution according to the invention, the etheramine of formula (1) or (2), with a view to improving its solubility in water as well as its lubricating and disinfecting properties, is completely or partially neutralized up to a pH of 5 to 9, preferably 6 to 8, using an organic acid chosen from the group comprising acetic, hydroxyacetic acids , gluconic, lactic, benzoic, C₈ to C₂₀ fatty acids, such as coconut fatty acid or oleic acid, or using a mineral acid chosen from the group comprising phosphoric and hydrochloric acids; preferably, the neutralization is carried out using acetic acid or gluconic acid.

Selon un autre mode de réalisation avantageux, la solution conforme à l'invention comprend un agent tensioactif, de préférence non ionique, choisi parmi les produits non ou peu moussants.According to another advantageous embodiment, the solution according to the invention comprises a surfactant, preferably nonionic, chosen from non-foaming or low foaming products.

Un tel agent permet d'améliorer l'efficacité nettoyante de la solution en même temps qu'il en facilite la formulation.Such an agent improves the cleaning efficiency of the solution at the same time as it facilitates the formulation.

Selon un autre mode de réalisation avantageux, la solution conforme à l'invention comprend, pour faciliter la formulation mais également pour améliorer le comportement au vieillissement, un solvant hydrosoluble choisi parmi les alcools à chaîne courte en C₁ à C₈ et, de préférence, en C₂ ou C₃, notamment l'éthanol, le n-propanol ou l'isopropanol et les éthers de glycols du groupe comprenant les éthers méthylique, éthylique, butylique ou phénylique du propylène- ou du dipropylène- ou du tripropylène-glycol, ainsi que les mêmes éthers de l'éthylène- ou du diéthylèneglycol, notamment ceux connus sous les marques de fabrique NAPSOL (BP Chemicals) et DOWANOL (Dow Chemical).According to another advantageous embodiment, the solution according to the invention comprises, to facilitate the formulation but also to improve the aging behavior, a water-soluble solvent chosen from alcohols with a short chain from C₁ to C₈ and, preferably, from C₂ or C₃, in particular ethanol, n-propanol or isopropanol and the glycol ethers of the group comprising the methyl, ethyl, butyl or phenyl ethers of propylene- or dipropylene- or tripropylene glycol, as well as same ethers of ethylene- or diethylene glycol, in particular those known under the trademarks NAPSOL (BP Chemicals) and DOWANOL (Dow Chemical).

Selon un autre mode de réalisation avantageux, la solution conforme à l'invention comporte des additifs désinfectants actifs à l'égard de souches bactériennes particulières, des agents modifiant la viscosité de la solution et des colorants.According to another advantageous embodiment, the solution according to the invention comprises disinfectant additives active with regard to particular bacterial strains, agents modifying the viscosity of the solution and dyes.

Selon un autre mode de réalisation avantageux, la solution conforme à l'invention, préparée à une concentration de 0,2 à 1% en volume, contient au moins une étheramine de formule (1) et/ou (2) ainsi qu'éventuellement un agent tensio-actif et un solvant hydrosoluble.According to another advantageous embodiment, the solution according to the invention, prepared at a concentration of 0.2 to 1% by volume, contains at least one etheramine of formula (1) and / or (2) as well as optionally a surfactant and a water-soluble solvent.

La solution conforme à l'invention peut être commercialisée sous la forme d'un concentré caractérisé par le fait qu'il est constitué comme suit:

  • étheramine: 5 à 20% en poids, de préférence de 10 à 17%,
  • agent tensio-actif peu moussant: 2 à 10% en poids,
  • solvant de type alcool ou éther de glycol: 2 à 10% en poids,
  • eau q.s.p. 100%.
The solution according to the invention can be marketed in the form of a concentrate, characterized in that it is constituted as follows:
  • etheramine: 5 to 20% by weight, preferably 10 to 17%,
  • low foaming surfactant: 2 to 10% by weight,
  • solvent of alcohol or glycol ether type: 2 to 10% by weight,
  • water qs 100%.

Le susdit concentré conduit à la susdite solution prête à l'emploi par dilution avec les quantités appropriées d'eau.The above concentrate leads to the above ready-to-use solution by dilution with the appropriate quantities of water.

Pour cette dilution, on peut avoir recours aussi bien à une eau adoucie (0 à 10°TH) qu'à une eau dure de 30°TH par exemple.For this dilution, we can use both softened water (0 to 10 ° TH) and hard water of 30 ° TH for example.

Dans ce qui suit, on montre l'intérêt de la solution conforme à l'invention du point de vue de ses qualités bactéricides et levuricides, du point de vue de l'absence de dépôts lors du fonctionnement, du point de vue de la qualité de la "glisse" obtenue sur chaîne transporteuse et du point de vue de la diminution de la DCO (à savoir la "demande chimique en oxygène") obtenue par rapport aux solutions classiques à base de savon.In what follows, we show the interest of the solution according to the invention from the point of view of its bactericidal and yeasticidal qualities, from the point of view of the absence of deposits during operation, from the point of view of the quality of the "sliding" obtained on the conveyor chain and from the point of view of the reduction of the COD (namely the "chemical oxygen demand") obtained compared to conventional solutions based on soap.

1. Efficacité bactéricide et levuricide 1. Bactericidal and yeasticidal efficacy

Cette efficacité a été démontrée en utilisant, pour la solution conforme à l'invention, des étheramines de marque commerciale TOMAH (Société EXXON CHEMICAL).This efficacy has been demonstrated by using, for the solution in accordance with the invention, etheramines of the commercial brand TOMAH (Company EXXON CHEMICAL).

Dans le tableau I ci-après, on a indiqué la constitution de quatre (A, B, C, D) solutions conformes à l'invention, leur pH et leur efficacité bactéricide en eau déminéralisée en comparaison avec celle de deux compositions de l'art antérieur (Réf. 1 et Réf. 2).

Figure imgb0001
In Table I below, the constitution of four (A, B, C, D) solutions according to the invention is indicated, their pH and their bactericidal efficacy in demineralized water in comparison with that of two compositions of the prior art (Ref. 1 and Ref. 2).
Figure imgb0001

L'efficacité bactéricide a été confirmée en présence d'eau dure pour quatre autres solutions conformes à l'invention (E, F, G, M) et les résultats sont réunis dans le tableau II ci-après. TABLEAU II E F G H Isotridécyloxypropylamine (TOMAH PA 17) 10 10 10 15 Acide acétique à 80% 2,6 3,2 3,1 4,6 Ether n butylique de l'éthylèneglycol 5 5 5 5 Alcool tridécylique 10 OE (LAUROXAL 10 de Witco Chemical) 4 - - 4 Alcool laurique 20 OE (REMCOPAL 20 de Gerland) - - 4 - Eau - - qsp 100 - pH tel que 8,0 6,0 6,0 6,0 Efficacité sur E. Coli en eau dure à 30°TH (norme AFNOR NF T72 171) 0,25% 0,25% 0,25% < 0,1% The bactericidal efficacy was confirmed in the presence of hard water for four other solutions in accordance with the invention (E, F, G, M) and the results are collated in Table II below. TABLE II E F G H Isotridecyloxypropylamine (TOMAH PA 17) 10 10 10 15 80% acetic acid 2.6 3.2 3.1 4.6 Ethylene glycol butyl ether 5 5 5 5 Tridecyl alcohol 10 OE (LAUROXAL 10 from Witco Chemical) 4 - - 4 Lauric alcohol 20 OE (REMCOPAL 20 from Gerland) - - 4 - Water - - qs 100 - pH as 8.0 6.0 6.0 6.0 Efficiency on E. Coli in hard water at 30 ° TH (AFNOR NF T72 171 standard) 0.25% 0.25% 0.25% <0.1%

2. Efficacité du point de vue de l'absence de dépôts 2. Effectiveness from the point of view of the absence of deposits

L'avantage des solutions conformes à l'invention par rapport aux solutions de l'art antérieur, par exemple à base d'amines grasses (brevets EP-A-0 372 628 et US-A-4 839 067) est montré par un test selon lequel on observe le comportement des solutions à 0,6% en volume (d'une part, selon l'art antérieur et d'autre part, selon l'invention) dans une eau déminéralisée ajustée à 500 ppm en ions sulfate (il est rappelé que les eaux industrielles contiennent en général entre 50 et 150 ppm d'ions sulfate).The advantage of the solutions according to the invention compared to the solutions of the prior art, for example based on fatty amines (patents EP-A-0 372 628 and US-A-4 839 067) is shown by a test according to which the behavior of the solutions at 0.6% by volume (on the one hand, according to the prior art and on the other hand, according to the invention) in demineralized water adjusted to 500 ppm in sulfate ions ( it is recalled that industrial waters generally contain between 50 and 150 ppm of sulfate ions).

Les résultats sont réunis dans le tableau III ci-après. TABLEAU III Solution selon l'art antérieur à base d'amine grasse (type oleylamine ou oleyl propylène diamine) . Solution très trouble après 24 heures . Dépôt important après 7 jours. Solution conforme à l'invention, l'amine grasse étant remplacée par une étheramine TOMAH . Solution trouble après 24 heures . Trouble mais sans dépôt arès 7 jours The results are collated in Table III below. TABLE III Solution according to the prior art based on fatty amine (oleylamine or oleyl propylene diamine type) . Very cloudy solution after 24 hours . Large deposit after 7 days. Solution according to the invention, the fatty amine being replaced by a TOMAH etheramine . Cloudy solution after 24 hours . Trouble but no deposit after 7 days

Il s'ensuit de ce résultat que le bouchage de buses peut être évité grâce à l'utilisation des solutions conformes à l'invention.It follows from this result that the clogging of nozzles can be avoided through the use of solutions according to the invention.

3. Efficacité du point de vue de la "glisse" 3. Effectiveness from the point of view of "sliding"

La "glisse" apportée par les solutions lubrifiantes a été mesurée sur une chaîne pilote en acier inoxydable avançant à une cadence de 0,33 m/s et à l'aide de laquelle on évalue la résistance au glissement exprimée par un indice I, d'un train de six bouteilles (bouteilles en verre d'un litre remplies d'eau).The "glide" provided by the lubricating solutions was measured on a stainless steel pilot chain advancing at a rate of 0.33 m / s and with the aid of which the slip resistance expressed by an index I, d is evaluated. '' a train of six bottles (one liter glass bottles filled with water).

Les six bouteilles dont le comportement est examiné sont attachées les unes aux autres par un filin relié à un dynamomètre, lui-même connecté à une table traçante et à un capteur digital, par exemple de la marque SEDEME.The six bottles whose behavior is examined are attached to each other by a rope connected to a dynamometer, itself connected to a plotter and a digital sensor, for example of the brand SEDEME.

L'indice I est un nombre sans unité et qui n'a de signification que par comparaison avec la lubrification avec de l'eau seule.The index I is a number without unit and which has meaning only in comparison with lubrication with water alone.

L'indice est égal à zéro lorsqu'aucune traction ne s'exerce sur le dynamomètre; à ce moment, le capteur est réglé à la valeur zéro.The index is equal to zero when no traction is exerted on the dynamometer; at this time, the sensor is set to zero.

Ensuite, un essai est réalisé en lubrifiant la chaîne avec de l'eau à 30°TH; dans ces conditions, le capteur indique une valeur I égale à 5,5.Then, a test is carried out by lubricating the chain with water at 30 ° TH; under these conditions, the sensor indicates a value I equal to 5.5.

On a constaté, par ailleurs, que l'intervalle entre I = 0 et I = 5,5 correspondait à toute l'échelle du papier de la table traçante et on s'est assuré, lors des différents essais effectués avec les solutions à tester que les valeurs relevées dans ces essais sur le papier sont bien proportionnelles aux indications numériques fournies par le capteur.It has also been found that the interval between I = 0 and I = 5.5 corresponds to the entire scale of the plotter paper and we have ensured, during the various tests carried out with the solutions to be tested that the values recorded in these tests on paper are well proportional to the digital indications provided by the sensor.

Plus l'indice mesuré est faible, plus les forces de frottement diminuent et meilleure est la glisse.The lower the measured index, the more the friction forces decrease and the better the glide.

Le test a été effectué sur, d'une part, une solution selon l'art antérieur (Réf. 3) et, d'autre part, sur les solutions conformes à l'invention identifiées plus haut, à savoir C, D, F, G et H, la solution Réf. 3 et les solutions conformes à l'invention étant à la concentration de 0,6% dans l'eau.The test was carried out on the one hand, a solution according to the prior art (Ref. 3) and, on the other hand, on the solutions according to the invention identified above, namely C, D, F , G and H, the solution Ref. 3 and the solutions according to the invention being at a concentration of 0.6% in water.

Les résultats sont réunis dans le tableau IV ci-après. TABLEAU IV Solutions testées Indice I Réf. 3 (formule commerciale classique à environ 16% de savon) 1,45 C 1,45 D 1,45 F 1,50 G 1,30 H 1,50 sans solution lubrifiante (eau seule) 5,50 The results are collated in Table IV below. TABLE IV Solutions tested Index I Ref. 3 (classic commercial formula with approximately 16% soap) 1.45 VS 1.45 D 1.45 F 1.50 G 1.30 H 1.50 without lubricant solution (water only) 5.50

De ce tableau, il résulte que les compositions conformes à l'invention ont des performances équivalentes à celles des solutions connues à base de savon.From this table, it follows that the compositions in accordance with the invention have performances equivalent to those of known solutions based on soap.

4. Efficacité du point de vue de la DCO obtenue 4. Effectiveness from the point of view of the COD obtained

On a déterminé la DCO exprimée en mg d'oxygène par litre pour deux solutions à 1% en poids dans l'eau, obtenues à partir d'un concentré conforme à l'invention, d'une part, et d'un concentré selon l'art antérieur à base de savon, d'autre part.The COD expressed in mg of oxygen per liter was determined for two solutions at 1% by weight in water, obtained from a concentrate in accordance with the invention, on the one hand, and of a concentrate according to the prior art based on soap, on the other hand.

Les résultats obtenus à l'aide du test conforme à la norme AFNOR NF T 90-101 sont réunies dans le tableau V. TABLEAU V Solution lubrifiante selon l'art antérieur à 16% de savon environ environ 8500 Solution lubrifiante conforme à l'invention à base d'étheramine 3 à 5000 selon les solutions The results obtained using the test in accordance with standard AFNOR NF T 90-101 are collated in table V. TABLE V Lubricant solution according to the prior art with approximately 16% soap about 8500 Etheramine-based lubricant solution according to the invention 3 to 5000 depending on the solutions

Ces résultats montrent l'avantage des solutions conformes à l'invention par rapport aux solutions selon l'art antérieur, avantage important dans le cadre de l'amélioration du comportement des produits vis-à-vis de l'environnement.These results show the advantage of the solutions according to the invention compared to the solutions according to the prior art, an important advantage in the context of improving the behavior of the products with respect to the environment.

Claims (8)

Solution lubrifiante et désinfectante pour chaîne transporteuse de récipients dans l'industrie agro-alimentaire, caractérisée par le fait qu'elle comporte une quantité efficace d'au moins une étheramine de formules:

        R-O-(CH₂)₃-NH₂   (1)

ou

        RO-(CH₂)₃-NH(CH₂)₃-NH₂   (2)

dans lesquelles R représente une chaîne alkyle, saturée ou insaturée, ramifiée en C₆ à C₂₁.
Lubricating and disinfecting solution for container conveyor chain in the food industry, characterized in that it comprises an effective amount of at least one etheramine of formulas:

RO- (CH₂) ₃-NH₂ (1)

or

RO- (CH₂) ₃-NH (CH₂) ₃-NH₂ (2)

in which R represents an alkyl chain, saturated or unsaturated, branched at C₆ to C₂₁.
Procédé de lubrification et de désinfection pour chaîne transporteuse de récipients dans l'industrie agro-alimentaire, caractérisé par le fait que l'on applique, sur une chaîne transporteuse dans l'industrie agro-alimentaire, une solution lubrifiante et désinfectante comportant une quantité efficace d'au moins une étheramine de formules:

        R-O-(CH₂)₃-NH₂   (1)

ou

        RO-(CH₂)₃-NH(CH₂)₃-NH₂   (2)

dans lesquelles R représente une chaîne alkyle, saturée ou insaturée, ramifiée en C₆ à C₂₁.
Lubrication and disinfection process for container conveyor chain in the food industry, characterized in that a lubricant and disinfectant solution comprising an effective amount is applied to a conveyor chain in the food industry at least one etheramine of formulas:

RO- (CH₂) ₃-NH₂ (1)

or

RO- (CH₂) ₃-NH (CH₂) ₃-NH₂ (2)

in which R represents an alkyl chain, saturated or unsaturated, branched at C₆ to C₂₁.
Solution lubrifiante et désinfectante selon la revendication 1, caractérisée par le fait que l'étheramine est neutralisée en totalité ou partiellement jusqu'à un pH de 5 à 9, de préférence de 6 à 8, ou bien à l'aide d'un acide organique choisi dans le groupe comprenant les acides acétique, hydroxyacétique, gluconique, lactique, benzoique, les acides gras en C₈ à C₂₀, tels que l'acide gras de coprah ou l'acide oléique, ou bien à l'aide d'un acide minéral choisi dans le groupe comprenant les acides phosphorique et chlorhydrique.Lubricant and disinfectant solution according to claim 1, characterized in that the etheramine is completely or partially neutralized up to a pH of 5 to 9, preferably 6 to 8, or else using an acid organic selected from the group comprising acetic, hydroxyacetic, gluconic, lactic, benzoic acids, C₈ to C₂₀ fatty acids, such as coconut fatty acid or oleic acid, or else using an acid mineral chosen from the group comprising phosphoric and hydrochloric acids. Solution lubrifiante et désinfectante selon la revendication 1, caractérisée par le fait que l'étheramine est neutralisée à l'aide de l'acide acétique ou de l'acide gluconique.Lubricant and disinfectant solution according to claim 1, characterized in that the etheramine is neutralized using acetic acid or gluconic acid. Solution lubrifiante et désinfectante selon la revendication 1, caractérisée par le fait qu'elle comprend un agent tensio-actif, de préférence non ionique, choisi parmi les produits non ou peu moussants.Lubricant and disinfectant solution according to claim 1, characterized in that it comprises a surfactant, preferably nonionic, chosen from non-foaming or low foaming products. Composition lubrifiante et désinfectante selon la revendication 1, caractérisée par le fait qu'elle comprend un solvant hydrosoluble choisi parmi, d'une part, les alcools à chaîne courte en C₁ à C₈ et, de préférence, en C₂ ou C₃, du groupe comprenant l'éthanol, le n-propanol ou l'isopropanol et, d'autre part, les éthers de glycols du groupe comprenant les éthers méthylique, éthylique, butylique ou phénylique du propylène- ou du dipropylène- ou du tripropylène-glycol, ainsi que les mêmes éthers de l'éthylène- ou du diéthylèneglycol, de même que ceux connus sous les marques de fabrique NAPSOL (BP Chemicals) et DOWANOL (Dow Chemical).Lubricant and disinfectant composition according to claim 1, characterized in that it comprises a water-soluble solvent chosen from, on the one hand, the short-chain alcohols C₁ to C₈ and, preferably, C₂ or C₂, from the group comprising ethanol, n-propanol or isopropanol and, on the other hand, the glycol ethers of the group comprising the methyl, ethyl, butyl or phenyl ethers of propylene- or dipropylene- or tripropylene glycol, as well as the same ethers of ethylene- or diethylene glycol, as well as those known under the trademarks NAPSOL (BP Chemicals) and DOWANOL (Dow Chemical). Solution lubrifiante et désinfectante selon l'une des revendications 1 et 3 à 6, caractérisée par le fait qu'elle est préparée à une concentration de 0,2 à 1% en volume et qu'elle contient au moins une étheramine de formule (1) et/ou (2) ainsi qu'éventuellement un agent tensio-actif et un solvant hydrosoluble.Lubricant and disinfectant solution according to one of Claims 1 and 3 to 6, characterized in that it is prepared at a concentration of 0.2 to 1% by volume and that it contains at least one etheramine of formula (1 ) and / or (2) as well as optionally a surfactant and a water-soluble solvent. Concentré propre à fournir, par dilution avec une quantité appropriée d'eau, la solution lubrifiante et désinfectante selon la revendication 7, caractérisé par le fait qu'il est constitué comme suit: - étheramine: 5 à 20% en poids, de préférence de 10 à 17%, - agent tensio-actif peu moussant: 2 à 10% en poids, - solvant de type alcool ou éther de glycol: 2 à 10% en poids, - eau q.s.p. 100%. Concentrate capable of supplying, by dilution with an appropriate quantity of water, the lubricating and disinfecting solution according to claim 7, characterized in that it is constituted as follows: - etheramine: 5 to 20% by weight, preferably from 10 to 17%, - low foaming surfactant: 2 to 10% by weight, - solvent of alcohol or glycol ether type: 2 to 10% by weight, - water qs 100%.
EP92402521A 1991-09-16 1992-09-15 Lubricating and desinfecting solution for containers conveyor chain the food industry and process for its use Expired - Lifetime EP0533552B1 (en)

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FR9111384 1991-09-16
FR9111384A FR2681312A1 (en) 1991-09-16 1991-09-16 LUBRICATING AND DISINFECTING SOLUTION FOR TRANSPORTING CHAIN OF CONTAINERS IN THE AGRO-FOOD INDUSTRY AND METHOD FOR ITS IMPLEMENTATION

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WO1995026389A1 (en) * 1994-03-25 1995-10-05 Unilever N.V. Alkaline diamine track lubricants
WO1997045509A1 (en) * 1996-05-31 1997-12-04 Ecolab Inc. Alkyl ether amine conveyor lubricants containing corrosion inhibitors
WO1997045508A1 (en) * 1996-05-31 1997-12-04 Ecolab Inc. Alkyl ether amine conveyor lubricant
WO1998059023A1 (en) * 1997-06-20 1998-12-30 Ecolab Inc. Alkaline ether amine conveyor lubricant
EP0897419A1 (en) * 1997-01-13 1999-02-24 Mobil Oil Corporation Friction reducing additives for fuels and lubricants
BE1011367A3 (en) * 1997-09-12 1999-08-03 Sopura S A Lubricant formulation and use of same
US6247478B1 (en) 1996-11-15 2001-06-19 Ecolab Inc. Cleaning method for polyethylene terephthalate containers
US6260561B1 (en) 1998-08-13 2001-07-17 The Dow Chemical Company Method for using aliphatic amines as cleaners for swimming pools
EP1273653A1 (en) * 2001-07-04 2003-01-08 Polygon Chemie AG Etherdiamines or N-alkyl-diaminopropane or their mixture as lubricants
US6554005B1 (en) 1996-11-15 2003-04-29 Ecolab Inc. Cleaning method for polyethylene terephthalate containers
WO2005014491A1 (en) * 2003-08-05 2005-02-17 Clariant Gmbh Etheramines and their nitriles as biocide for water treatment
WO2005115485A1 (en) * 2004-05-24 2005-12-08 Bausch & Lomb Incorporated Antimicrobial compositions and uses thereof
WO2006066120A1 (en) * 2004-12-17 2006-06-22 Johnsondiversey, Inc. Method of lubricating a conveyor system
US7595288B2 (en) 2004-02-06 2009-09-29 Henkel Kommanditgesellschaft Auf Aktien Antimicrobial metal working fluids
US20150315378A1 (en) * 2012-12-20 2015-11-05 Dow Global Technologies Llc Low emission epoxy curing agents
WO2017042514A1 (en) * 2015-09-10 2017-03-16 Ceca S.A. Ether amine compounds and use thereof as flotation collector
CN108349854A (en) * 2015-10-27 2018-07-31 T·P·戴利 amine beneficiation collecting agent
US11344041B2 (en) 2015-12-30 2022-05-31 Prolacta Bioscience, Inc. Human milk products useful in pre- and post-operative care
US11419342B2 (en) 2013-03-13 2022-08-23 Prolacta Bioscience, Inc. High fat human milk products

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Cited By (32)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1995026389A1 (en) * 1994-03-25 1995-10-05 Unilever N.V. Alkaline diamine track lubricants
WO1997045509A1 (en) * 1996-05-31 1997-12-04 Ecolab Inc. Alkyl ether amine conveyor lubricants containing corrosion inhibitors
WO1997045508A1 (en) * 1996-05-31 1997-12-04 Ecolab Inc. Alkyl ether amine conveyor lubricant
CN1070529C (en) * 1996-05-31 2001-09-05 埃科莱布有限公司 Alkyl ether amine conveyor lubricant containing corrosion inhibitors
CN1068374C (en) * 1996-05-31 2001-07-11 埃科莱布有限公司 Alkyl ether amine conveyor lubricant
US6247478B1 (en) 1996-11-15 2001-06-19 Ecolab Inc. Cleaning method for polyethylene terephthalate containers
US6554005B1 (en) 1996-11-15 2003-04-29 Ecolab Inc. Cleaning method for polyethylene terephthalate containers
EP0897419A1 (en) * 1997-01-13 1999-02-24 Mobil Oil Corporation Friction reducing additives for fuels and lubricants
EP0897419A4 (en) * 1997-01-13 2001-01-17 Mobil Oil Corp Friction reducing additives for fuels and lubricants
US5932526A (en) * 1997-06-20 1999-08-03 Ecolab, Inc. Alkaline ether amine conveyor lubricant
AU743671B2 (en) * 1997-06-20 2002-01-31 Ecolab Inc. Alkaline ether amine conveyor lubricant
CN1097631C (en) * 1997-06-20 2003-01-01 埃科莱布有限公司 Alkaline ether amine conveyor lubricant
WO1998059023A1 (en) * 1997-06-20 1998-12-30 Ecolab Inc. Alkaline ether amine conveyor lubricant
BE1011367A3 (en) * 1997-09-12 1999-08-03 Sopura S A Lubricant formulation and use of same
US6260561B1 (en) 1998-08-13 2001-07-17 The Dow Chemical Company Method for using aliphatic amines as cleaners for swimming pools
EP1273653A1 (en) * 2001-07-04 2003-01-08 Polygon Chemie AG Etherdiamines or N-alkyl-diaminopropane or their mixture as lubricants
WO2005014491A1 (en) * 2003-08-05 2005-02-17 Clariant Gmbh Etheramines and their nitriles as biocide for water treatment
US7595288B2 (en) 2004-02-06 2009-09-29 Henkel Kommanditgesellschaft Auf Aktien Antimicrobial metal working fluids
WO2005115485A1 (en) * 2004-05-24 2005-12-08 Bausch & Lomb Incorporated Antimicrobial compositions and uses thereof
US7632869B2 (en) 2004-05-24 2009-12-15 Bausch & Lomb Incorporated Antimicrobial compositions and uses thereof
WO2006066120A1 (en) * 2004-12-17 2006-06-22 Johnsondiversey, Inc. Method of lubricating a conveyor system
US8119578B2 (en) 2004-12-27 2012-02-21 Diversey, Inc. Method of lubricating a conveyor system
US9469721B2 (en) * 2012-12-20 2016-10-18 Blue Cube Ip Llc Low emission epoxy curing agents
US20150315378A1 (en) * 2012-12-20 2015-11-05 Dow Global Technologies Llc Low emission epoxy curing agents
US11419342B2 (en) 2013-03-13 2022-08-23 Prolacta Bioscience, Inc. High fat human milk products
WO2017042514A1 (en) * 2015-09-10 2017-03-16 Ceca S.A. Ether amine compounds and use thereof as flotation collector
FR3040994A1 (en) * 2015-09-10 2017-03-17 Ceca Sa ETHERAMINE COMPOUNDS AND ITS USE AS A FLOTATION COLLECTOR
CN108137481A (en) * 2015-09-10 2018-06-08 阿肯马法国公司 Ether amines compound and its purposes as flotation agent
US10815337B2 (en) 2015-09-10 2020-10-27 Arkema France Ether amine compounds and use thereof as flotation collector
CN113943226A (en) * 2015-09-10 2022-01-18 阿肯马法国公司 Ether amine compounds and their use as flotation agents
CN108349854A (en) * 2015-10-27 2018-07-31 T·P·戴利 amine beneficiation collecting agent
US11344041B2 (en) 2015-12-30 2022-05-31 Prolacta Bioscience, Inc. Human milk products useful in pre- and post-operative care

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FR2681312B1 (en) 1995-03-10
DE69210728T2 (en) 1997-01-23
EP0533552B1 (en) 1996-05-15
ATE138091T1 (en) 1996-06-15
ES2087482T3 (en) 1996-07-16
FR2681312A1 (en) 1993-03-19
DE69210728D1 (en) 1996-06-20

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