Classifications

• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
  • C09K8/00—Compositions for drilling of boreholes or wells; Compositions for treating boreholes or wells, e.g. for completion or for remedial operations
  • C09K8/02—Well-drilling compositions
  • C09K8/32—Non-aqueous well-drilling compositions, e.g. oil-based
  • C09K8/36—Water-in-oil emulsions
• • G—PHYSICS
  • G02—OPTICS
  • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
  • G02B6/00—Light guides; Structural details of arrangements comprising light guides and other optical elements, e.g. couplings
• • G—PHYSICS
  • G02—OPTICS
  • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
  • G02B6/00—Light guides; Structural details of arrangements comprising light guides and other optical elements, e.g. couplings
  • G02B6/0001—Light guides; Structural details of arrangements comprising light guides and other optical elements, e.g. couplings specially adapted for lighting devices or systems
  • G02B6/0005—Light guides; Structural details of arrangements comprising light guides and other optical elements, e.g. couplings specially adapted for lighting devices or systems the light guides being of the fibre type
  • G02B6/0008—Light guides; Structural details of arrangements comprising light guides and other optical elements, e.g. couplings specially adapted for lighting devices or systems the light guides being of the fibre type the light being emitted at the end of the fibre
• • G—PHYSICS
  • G02—OPTICS
  • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
  • G02B6/00—Light guides; Structural details of arrangements comprising light guides and other optical elements, e.g. couplings
  • G02B6/0001—Light guides; Structural details of arrangements comprising light guides and other optical elements, e.g. couplings specially adapted for lighting devices or systems
  • G02B6/0096—Light guides; Structural details of arrangements comprising light guides and other optical elements, e.g. couplings specially adapted for lighting devices or systems the lights guides being of the hollow type
• • G—PHYSICS
  • G02—OPTICS
  • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
  • G02B6/00—Light guides; Structural details of arrangements comprising light guides and other optical elements, e.g. couplings
  • G02B6/10—Light guides; Structural details of arrangements comprising light guides and other optical elements, e.g. couplings of the optical waveguide type
• • G—PHYSICS
  • G02—OPTICS
  • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
  • G02B6/00—Light guides; Structural details of arrangements comprising light guides and other optical elements, e.g. couplings
  • G02B6/24—Coupling light guides
  • G02B6/26—Optical coupling means
  • G02B6/262—Optical details of coupling light into, or out of, or between fibre ends, e.g. special fibre end shapes or associated optical elements
• • G—PHYSICS
  • G02—OPTICS
  • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
  • G02B6/00—Light guides; Structural details of arrangements comprising light guides and other optical elements, e.g. couplings
  • G02B6/0001—Light guides; Structural details of arrangements comprising light guides and other optical elements, e.g. couplings specially adapted for lighting devices or systems

Definitions

• the invention describes new drilling fluid based on ester oils and invert drilling muds based thereon, which are characterized by high ecological compatibility and, at the same time, good standing and usage properties.
• An important area of application for the new drilling fluid systems is offshore drilling for the development of petroleum and / or natural gas, whereby the invention is particularly concerned with providing technically usable drilling fluids with high ecological compatibility .
• the use of the new drilling fluid systems is particularly important in the marine area, but is not limited to this.
• the new systems can Spül ⁇ very general use found in 'landge ⁇ assisted drilling, for example in geothermal drilling, water drilling, geoscientific drilling and mine drilling.
• the ester-based drilling oil fluids selected according to the invention substantially simplify the ⁇ cotoxic problem area.
• Oil-based drilling fluids are generally used as so-called invert emulsion slurries, which consist of a three-phase system: oil, water and finely divided solids. These are preparations of the type of W / O emulsions, i.e. H . the aqueous phase is heterogeneously finely dispersed in the closed oil phase.
• a plurality of additives are provided to stabilize the overall system and to set the desired performance properties, in particular emulsifiers or emulsifier systems, weighting agents, fluid loss additives, alkali reserves, viscosity regulators and the like.
• emulsifiers or emulsifier systems weighting agents, fluid loss additives, alkali reserves, viscosity regulators and the like.
• Oil-based drilling fluids were initially based on diesel oil fractions containing aromatics.
• ester oils of the type concerned do not behave in the same way as the mineral oil fractions based on pure hydrocarbons used to date. Ester oils of any constitution are subject to practical use in the W / O invert drilling muds of a partial hydrolysis. This forms free carboxylic acids. These in turn react with the alkaline constituents that are always present in drilling fluid systems of the type affected here - for example. B. with the alkali reserve used for corrosion protection - to the corresponding salts.
• salts of strongly hydrophilic bases and the acids in the range from about C 12 to 24 predominantly found in oils of natural origin are known to be compounds with comparatively high H LB values, in particular for adjusting and stabilizing O / W emulsions to lead .
• the alkali reserve it is essential that the use of strongly hydrophilic bases such as alkali hydroxide and / or diethanamine be avoided.
• the addition of lime (calcium hydroxide or lime) and / or the concomitant use of zinc oxide or comparable zinc compounds is provided as the alkali reserve.
• an additional restriction is also required here. If the undesired thickening of the oil-based invert rinsing system is to be prevented in practical operation, the amount of the alkalizing additive and in particular the amount of lime must be limited. According to the disclosure of the older applications mentioned, the maximum amount envisaged is about 2 lb / bbl oil rinse.
• the teaching of the present invention is based on further considerations and findings which are unknown in the field of invert drilling fluids with a closed oil phase which are concerned here.
• the teaching according to the invention takes into account the fact that drilling fluids containing ester oils of the type concerned here are subject to limited partial hydrolysis in practical operation, so that inevitably increasingly free carboxylic acids form as a hydrolysis product and sooner or later reach a critical or - at least endangered state of aging , which forms as an undesirable thickening of the drilling fluid.
• the teaching according to the invention is based on the concept of using an additional additive in invert drilling fluids of the type concerned here, which is suitable for keeping the desired theological data of the drilling fluid in the required range, even if increasingly more or more or even excessive amounts of free carboxylic acid are formed by partial ester hydrolysis.
• the teaching of the invention not only wants to trap the free carboxylic acids formed in a harmless form, but also, if desired, convert them into valuable components with stabilizing or emulsifying properties for the overall system.
• the invention accordingly relates to the use of basic and for in a first embodiment Salt formation with carboxylic acids enabled amine compounds of pronounced oleophilic nature and at most limited solubility in water as an additive in W / O invert drilling oil slurries, the ester oils in the closed oil phase and, together with the disperse aqueous phase, emulsifiers, weighting agents, fluid loss additives and, if desired, further additives contain, to protect the drilling oil sludge against unwanted thickening in use and / or to improve their flowability.
• the invention relates to W / OI invert drilling fluids which are suitable for the offshore development of petroleum or natural gas deposits and which, in a closed oil phase containing ester oils, comprise a disperse aqueous phase together with emulsifiers, weighting agents, fluid Loss additives and, if desired, further conventional additives, the invention in this embodiment being characterized in that the drilling fluids contain, as an additional additive, basic amine compounds which are capable of salt formation with carboxylic acids, are of a pronounced oleophilic nature and have a maximum solubility in water.
• the addition of the additives according to the invention gives the drilling muds protection against undesired thickening in use and is generally suitable for improving their flowability.
• the invention is directed to additive mixtures which are suitable for the stated purpose in drilling fluids containing ester oils and which contain the basic amine compounds which are capable of salt formation with carboxylic acids and which are distinctly oleophilic in nature and at most limited in water solubility in a solvent miscible with the oil phase. So-called nonpolluting oils are preferred as solvents, the ester oils in particular being of particular importance here.
• the anti-aging agents based on the oleophilic basic amine compounds are expedient in concentrations of at least about 20% by weight. -%, preferably in amounts of at least about 50 wt. -% in front .
• the core of the teaching according to the invention in all of its embodiments is the knowledge that the carboxylic acids which are inevitably liberated in practical operation by partial hydrolysis of the ester oils are intercepted when the anti-aging agents based on oleophilic basic amine compounds are also used, without resulting in any Disruption of the theological properties of invert mud.
• suitable amine compounds By selecting suitable amine compounds, it is even possible to form valuable stabilizing and / or emulsifying mixture components in situ by means of the salt formation now occurring.
• the oleophilic basic t amine compounds can be added to the drilling fluid systems from the start and / or they can be added to them during use. It has been shown that by adding or.
• Basic amine compounds with shorter carbon wedges are known to be to a considerable extent water-soluble and, if appropriate, water-miscible in any proportions.
• the amine compounds selected according to the invention are characterized by markedly limited solubility in water with simultaneous formation of their oleophilic character.
• Their water solubility at room temperature is generally below about 10% by weight and in the preferred embodiment does not exceed about 5% by weight.
• those oleophilic amine compounds which have very low limit values for their water solubility at room temperature.
• An important limit is around 1% by weight, preferably less than about 0.1 wt. -%.
• Basic amines which are particularly important for the invention can be mentioned as being practically water-insoluble.
• Oleophilic amines of the type described can generally be used insofar as they are capable of salt formation with the carboxylic acids released during the ester hydrolysis and are preferably soluble in the oil phase.
• preference is given in this large range of objectively suitable amine compounds to ecologically comparatively harmless compounds.
• Aromatic amines are generally less suitable on the basis of these considerations, so that in a further preferred embodiment of the invention oleophilic amine compounds are used which are at least predominantly free of aromatic constituents.
• Suitable compounds for carrying out the teaching according to the invention can generally be assigned to the groups of aliphatic, cycloaliphatic and / or heterocyclic amines.
• the respective representatives can contain one or more N groups which are capable of forming salts with carboxylic acids.
• Amine compounds of the type described can be nitrogen-containing saturated hydrocarbon compounds, but amine hydrocarbons which contain one or more olefinically unsaturated groups in at least one of their hydrocarbon members are also suitable.
• a first group includes primary, secondary and tertiary amines with one or more N atoms, the ratio of hydrocarbon groups to amine groups in the respective compound being chosen so that the conditions given above for limited water solubility and pronounced oleophilicity are met .
• the number ratio C / N is at least about 5 or better 6, but is preferably above this.
• amines of the type affected here which are readily available industrially, there are often 1 or 2 comparatively long-chain hydrocarbon radicals on the amino nitrogen and - if present - the methyl radicals on the remainder. Typical examples of the type concerned here contain 1 nitrogen atom per molecule.
• N H groups present are alkoxylated with, for example, ethylene oxide and / or propylene oxide or. higher homologues, e.g. B. Butylene oxide, oligo-alkoxide groups are introduced.
• long-chain primary and / or secondary amines are sufficiently oleophilic even when introducing up to about 8 to 10 EO and / or PO groups that they can be considered for use in the sense of the invention.
• Technically easily accessible amine compounds for use in the context of the invention are derived from the epoxidation of olefinically unsaturated hydrocarbon compounds. with subsequent introduction of the N function by adding “to the epoxy group.
• the implementation of the epoxidized intermediate components with primary u ⁇ d / or secondary amines with the formation of the corresponding alkanolamines is of particular importance.
• Also suitable for opening the epoxy ring are polyamines, in particular lower polyamines of the type corresponding to alkylene diamines.
• aminoamides which are composed of preferably long-chain carboxylic acids and polyfunctional, derive in particular lower amines of the aforementioned type. It is important here that at least one of the amino functions is not bound in the amide form, but is retained as a potentially acid-forming basic amino group. Both here and in all the cases described above, the basic amino groups, when they are formed as secondary or tertiary amino groups, can contain, in addition to the oleophilic part of the molecule, hydroxyalkyl substituents and here in particular lower hydroxyalkyl substituents with up to 5, preferably with up to 3, carbon atoms exhibit .
• Suitable N-basic starting components for the production of such addition products with long-chain oleophilic molecule constituents are monoethanolamine and / or diethanolamine.
• suitable additives for the purposes of the invention are reaction products from the epoxidation of long-chain olefins having, for example, 8 to 36, in particular about 10 to 18, carbon atoms and mono- and / or diethanolamine.
• Alpha-standing olefins of the type mentioned can be of particular importance as a starting material for the epoxidation and the subsequent conversion to the secondary and / or tertiary amine with hydroxyalkyl groups on the N atom.
• heterocyclic additives for regulating the flow properties of drilling muds in the sense of the invention are the imidazoline compounds.
• Alkylpyridines can also be significant from this heterocyclic group.
• the additives based on oleophilic basic amine compounds for the purposes of the invention are preferably added to the drilling fluids in amounts not exceeding about 10 Ib / bbI and preferably in amounts not exceeding 5 Ib / bbI.
• the amount used can be determined, inter alia, by the shape of the use intended in practice. Different variants are possible here, which can also be connected to each other.
• the rheology * regulating additive is added to the drilling mud in a substantial amount from the beginning. It can then take on a double function.
• the invention forms the alkali reserve of the drilling fluid to intercept any ingress of acidic constituents such as CO_ and / or H_S
• the basic amine compound which may be in a large excess, absorbs the carboxylic acid fractions formed by hydrolysis to the extent of their formation and converts them into the corresponding oil-soluble salts.
• the invention initially works with the ester oil-based mud without " addition of the additives according to the invention - for example in the sense of the teaching of the earlier patent applications mentioned at the outset.... [D 8523 and D 8524) by the beginning of increasing the viscosity values, the additive according to the invention is used to regulate the
• Rheology metered batchwise or continuously to the drilling fluid This can be done easily during the drilling process. It is obvious that any combination of the metering of the additive according to the invention before and during the operation of the drilling or the use of the drilling fluid are possible between these two extremes. If suitable amine compounds which form effective emu igators systems are selected, it is even possible to save emulsifier parts in the oil portion to be replenished and instead to use the amine salts with emulsifier action which arise in situ to stabilize the overall system.
• the amine compounds can be added to the invert drilling muds directly or indirectly. For example, they can be incorporated into the oil phase containing ester oil beforehand, or they can be added to the overall system as such.
• additive concentrates are prepared, which are then used in particular during operation Drilling mud can be added.
• These are solutions of the oleophilic amine compounds in suitable solvents at preferred concentrations of the additive of at least about 20% by weight, but preferably of at least about 50% by weight.
• suitable solvents are nonpolluting oils that can be homogeneously incorporated into the drilling mud. Ester oils are particularly suitable here, for example those of the type described in the two older applications mentioned.
• the amount of the amine-based additives selected according to the invention can be reduced to the range required by the ester hydrolysis in the continuous process.
• only a slight excess of the oleophilic amine base is used, and the portion consumed by salt formation is metered in batches or continuously during the drilling process.
• the addition of amine base can, for example, in the range from 0.1 to 2 Ib / bbI (amine base / drilling fluid) or even less.
• ester oils are esters of monofunctional carboxylic acids or carboxylic acid mixtures and monofunctional alcohols, in particular the ester types described in detail in the older applications mentioned. To complete the disclosure of the invention, essential characteristics of such esters or ester mixtures are briefly summarized here.
• ester oils which are at least about 60% by weight, based on the carboxylic acid mixture, of esters of aliphatic C ... monocarboxylic acids and, if desired, the rest, to a lesser extent, of minor amounts of shorter-chain aliphatic and / or longer-chain, then in particular 1- and / or poly-unsaturated monocarboxylic acids.
• Estersutton ⁇ is preferred in the temperature range of 0 to "5 C a Brookfield (RVT) viscosity in the range not above 50 mPas, preferably not above 40 mPas vor ⁇ and have, in particular of at most about 30 mPas.
• the in Esters used in drilling mud show solidification values (pour point and pour point) below - 10 C, preferably below - 15 C and in particular have flash points above 100 C, preferably above 150 C.
• the carboxylic acids present in the ester or ester mixture are at least predominantly straight-chain and They are preferably of vegetable origin and can be derived from appropriate triglycerides such as coconut oil, palm kernel oil and / or baseball oil.
• the alcohol residues of the esters used conduct in particular from straight-chain and / or branched saturated alcohols with preferably 4 to 10 carbon atoms.
• These alcohol components can also be of vegetable and / or animal origin and have been obtained by reductive hydrogenation of corresponding carboxylic acid esters.
• ester oils is derived from olefinically 1- and / or polyunsaturated monocarboxylic acids with 16 to 24 carbon atoms or their mixtures with subordinate amounts of other, in particular saturated monocarboxylic acids and monofunctional alcohols with 2 to 12 carbon atoms. These ester oils are also flowable and pumpable in the temperature range from 0 to 5 ° C.
• ester oils are also flowable and pumpable in the temperature range from 0 to 5 ° C.
• are particularly useful ester of this type which has become more than 70 wt .-%, preferably more than 80 wt .-% and in particular more than 90 wt -.% Of olefinically ß ungesreli13 saturated carboxylic acids the range of _ C. derive ü .
• the solidification values are below - 10 ° C, preferably below - 15 C, while the flash points are above 100 C and preferably above 160 ° C.
• the esters used in the drilling mud show a Brookfield (RVT) viscosity of not more than 55 mPas, preferably not more than 45 mPas, in the temperature range from 0 to 5 C.
• ester oils of the type concerned here two subclasses can be defined.
• the unsaturated C_ present in the ester is derived.
• g___ ü monocarboxylic acid residues from not more than 35% by weight of 2- and poly-olefinically unsaturated acids, preferably at least about 60% by weight of the acid residues being simply olefinically unsaturated.
• the C. - - ⁇ - monocarboxylic acids present in the ester mixture are derived to more than 45% by weight. -%, preferably more than 55 wt. -% of 2- and / or multiple olefinic unsaturated acids.
• Saturated carboxylic acids in the Ci c / ig range present in the ester mixture advantageously do not make more than about 20% by weight. -% and in particular not more than about 10 parts by weight.
• Saturated carboxylic acid esters are preferably in the range of lower C numbers for the acid residues.
• the present carboxylic acid residues are at least predominantly straight-chain and are preferably of vegetable and / or animal origin.
• Vegetable starting materials are, for example, palm oil, peanut oil, castor oil and in particular rape oil.
• Carbonic acids of animal origin are, in particular, corresponding mixtures of fish oils such as herring oil.
• Invert drilling muds of the type concerned here usually contain, together with the closed oil phase, the finely disperse aqueous phase in amounts of about 5 to 45% by weight and preferably in amounts of about 5 to 25% by weight.
• the range from about 10 to 25% by weight of disperse aqueous phase can be of particular importance.
• plastic viscosity in the range from about 10 to 60 mPas, preferably from about 15 to 40 mPas
• yield point (YP) in the range from about 5 to 40 lb / 100 ft, preferably from about 10 to 25 lb / 100 ft - each determined at 50 ° C.
• Emulsifiers that can be used in practice are systems that are suitable for forming the required W / O emulsions.
• Selected oleophilic fatty acid salts for example those based on amidoamine compounds, are particularly suitable. Examples of this are described in the already cited US Pat. Nos. 4,374,737 and the literature cited therein.
• a particularly suitable type of emulsifier is the product sold by NL Baroid, London, under the trade name "EZ-mul".
• Emulsifiers of the type concerned here are sold commercially as highly concentrated active ingredient preparations and can be used, for example, in amounts of about 2.5 to 5% by weight, in particular in amounts of about 3 to 4% by weight. -% - each based on ester oil phase - are used.
• hydrophobicized lignite is used in particular as a fluid loss additive and thus in particular to form a dense covering of the drilling walls with a largely liquid-impermeable film.
• Suitable amounts are, for example, in the range from about 15 to 20 Ib / bbI or in the range from about 5 to 7% by weight, based on the ester oil phase.
• Drilling fluids of the type concerned here are the viscosity formers commonly used, a cationically modified, finely divided bentonite which can be used in particular in amounts of about 8 to 10 lb / bbl or in the range of about 2 to 4% by weight, based on the ester oil phase.
• the weighting agent usually used in the relevant practice for setting the required pressure equalization is barite, the additional amounts of which are adapted to the respectively expected conditions of the bore. For example, it is possible to Adding barite increases the specific weight of the drilling fluid to values in the range up to approximately 2.5 and preferably in the range from approximately 1.3 to 1.6.
• the disperse aqueous phase is loaded with soluble salts in invert drilling fluids of the type concerned here.
• Calcium chloride and / or potassium chloride are predominantly used here, the saturation of the aqueous phase at room temperature with the soluble salt being preferred.
• Emulsifiers may also serve to improve the oil wettability of the inorganic weighting agents.
• alkylbenzenesulfonates and imidazoline compounds are further examples. Additional information on the relevant prior art can be found in the following literature references: GB 2 158 437, EP 229 912 and DE 32 47 123.
• the drilling fluids based on the use of ester oils of the type described are also distinguished by a significantly improved lubricity. This is particularly important if the passage of the drill pipe, and thus also the borehole, deviate from the vertical in bores, for example at greater depths. The rotating drill pipe easily comes into contact with the drill hole and digs into it during operation. Ester oils of the type used according to the invention as an oil phase have a significantly better lubricating effect than the mineral oils previously used. This is another important advantage for the action according to the invention. Examples
• Flash point above 165 C pour point below - 5 ° C, density (20 ° C) from 0.857 to 0.861, iodine number and acid number each below 1, water content below 0.3% and the following viscosity data (Brookfield mPas) in the low temperature range:
• Examples 4 to 10 isobutyl rapeseed oil esters based on a mixture of predominantly unsaturated straight-chain carboxylic acids, which correspond approximately to the following distribution: 60% oleic acid, 20% linoleic acid, 9 to 10% linoienic acid, olefinically unsaturated C 2 O / 22 ⁇ monocarboxylic acids, for example 4%, the rest saturated monocarboxylic acids predominantly in the range C_. fi / _. ".
• the rapeseed oil ester used also has the following characteristics: density (20 ° C.) 0.872 g / cm; Pour point below
• An invert drilling fluid is made in a conventional manner using the following ingredients: -21 -
• the invert drilling fluid is then aged for 16 hours at 125 ° C. in an autoclave in a so-called "roller oven” in order to check the influence of temperature on the stability of the emulsion. Then the viscosity values at 50 ° C are determined again.
• Example 1 The invert drilling fluid of Example 1 is now additionally mixed with 0.5 g of a pronounced oleophilic basic amine.
• the basic amine is the reaction product of an epoxidized C_. _ / 1 ü -alpha-olefins and diethanolamine ("Araphen G2D" of the applicant) are used.
• Invert drilling fluid added the oleophilic basic amine ("Araphen G2D") in an amount of 1 g.
• the values determined on the unaged and aged material are the following:
• Example 4 The approach of Example 4 is repeated, but here the oleophilic basic amine stearylamine is used in an amount of 2 g.
• the values determined on the unaged and aged material are the following:
• the isobutyl rapeseed oil ester is mixed with 1 g of lime, but without the use of oleophilic basic amine compounds.
• the amount of 1 g of lime used in the general formulation is below the threshold value of 2 Ib / bbl, which corresponds to the addition of approximately 1.35 g lime for the formulation used here.
• the theological values determined on the unaged and aged material are as follows:
• Example 6 The formulation of Example 6 are now in addition 2 g of the oleophilic basic amine compound len "Araphen G2D" ⁇ added.
• the theological values determined on the drilling fluid are the following:
• Lime amount above the threshold of about 2 Ib / bbI is triggered during aging.
• Example 8 An invert drilling fluid according to Example 8 is now additionally added with 2 g "Araphen G2D".
• the rheology values determined on the unaged and aged material are the following:
• Example 10 The comparison with the rheology data of Example 8 shows the influence of the oleophilic basic amine compound added according to the invention.
• Example 10 The comparison with the rheology data of Example 8 shows the influence of the oleophilic basic amine compound added according to the invention.
• An invert drilling fluid according to Example 8 is additionally initially treated with 2 g of diethylenetriamine, ie. H. with a pronounced hydrophilic base. Then the rheological data are first determined on the unaged material.
• This invert rinse is then aged at 125 ° C. for 16 hours, as previously indicated. It turns out that the rinse is so thickened that it is not possible to record the rheological data.

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• Physics & Mathematics (AREA)
• General Physics & Mathematics (AREA)
• Optics & Photonics (AREA)
• Chemical & Material Sciences (AREA)
• Oil, Petroleum & Natural Gas (AREA)
• Life Sciences & Earth Sciences (AREA)
• General Life Sciences & Earth Sciences (AREA)
• Engineering & Computer Science (AREA)
• Materials Engineering (AREA)
• Organic Chemistry (AREA)
• Treatment Of Sludge (AREA)
• Lubricants (AREA)
• Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
• Agricultural Chemicals And Associated Chemicals (AREA)
• Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
• Dental Preparations (AREA)
• Detergent Compositions (AREA)
• Nitrogen Condensed Heterocyclic Rings (AREA)
• Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
• Soil Conditioners And Soil-Stabilizing Materials (AREA)

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• 1989
  • 1989-02-09 DE DE3903785A patent/DE3903785A1/de not_active Withdrawn
• 1990
  • 1990-01-31 EP EP90101899A patent/EP0382070B1/de not_active Expired - Lifetime
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  • 1990-01-31 AU AU49579/90A patent/AU627836B2/en not_active Ceased
  • 1990-01-31 DK DK90101899.4T patent/DK0382070T3/da active
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• 1991
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