WO2017129529A1 - Compositions de résine active modifiées et leur utilisation pour le revêtement d'agents de soutènement - Google Patents

Compositions de résine active modifiées et leur utilisation pour le revêtement d'agents de soutènement Download PDF

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Publication number
WO2017129529A1
WO2017129529A1 PCT/EP2017/051337 EP2017051337W WO2017129529A1 WO 2017129529 A1 WO2017129529 A1 WO 2017129529A1 EP 2017051337 W EP2017051337 W EP 2017051337W WO 2017129529 A1 WO2017129529 A1 WO 2017129529A1
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WIPO (PCT)
Prior art keywords
reactive resin
resin composition
proppant
flowable
atoms
Prior art date
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PCT/EP2017/051337
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German (de)
English (en)
Inventor
Sebastian Knör
Daniel Calimente
Arndt Schlosser
Original Assignee
Wacker Chemie Ag
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Wacker Chemie Ag filed Critical Wacker Chemie Ag
Priority to US16/071,991 priority Critical patent/US11078410B2/en
Priority to JP2018539327A priority patent/JP2019510096A/ja
Priority to CN201780007823.9A priority patent/CN108495909A/zh
Priority to EP17701463.6A priority patent/EP3408346A1/fr
Priority to KR1020187024413A priority patent/KR102104024B1/ko
Publication of WO2017129529A1 publication Critical patent/WO2017129529A1/fr

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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
    • C09K8/60—Compositions for stimulating production by acting on the underground formation
    • C09K8/80—Compositions for reinforcing fractures, e.g. compositions of proppants used to keep the fractures open
    • C09K8/805—Coated proppants
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L61/00—Compositions of condensation polymers of aldehydes or ketones; Compositions of derivatives of such polymers
    • C08L61/04—Condensation polymers of aldehydes or ketones with phenols only
    • C08L61/06—Condensation polymers of aldehydes or ketones with phenols only of aldehydes with phenols
    • 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
    • C09K8/60—Compositions for stimulating production by acting on the underground formation
    • C09K8/62—Compositions for forming crevices or fractures
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/04—Polysiloxanes
    • C08G77/14—Polysiloxanes containing silicon bound to oxygen-containing groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/42—Block-or graft-polymers containing polysiloxane sequences
    • C08G77/445—Block-or graft-polymers containing polysiloxane sequences containing polyester sequences
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/42—Block-or graft-polymers containing polysiloxane sequences
    • C08G77/46—Block-or graft-polymers containing polysiloxane sequences containing polyether sequences

Definitions

  • the present invention relates to modified
  • Reactive resin compositions and their use as
  • the fracking process is used in the extraction of oil and gas and is a method for the generation, widening and stabilization of cracks in the rock of a deposit in the deep underground, with the aim of increasing the permeability of
  • uncoated proppants are brittle and do not have the necessary compressive strength for conveying at great depths.
  • the breakage of the proppant under the high pressure fines are released, which clog the cracks and the oil or
  • Supporting agents have improved resistance compared to the uncoated proppants.
  • the effect of the coating e.g. with organic resins, but is limited by the fact that the available coatings themselves are very brittle and also tend to break or flake.
  • WO2008088449 A2 discloses a possibility for reducing the brittleness of coatings of such particles, wherein thermosetting reactive resins such as epoxy resins with block copolymers and coupling agents are added so as to achieve an improvement in the impact resistance of the coating.
  • thermosetting reactive resins such as epoxy resins with block copolymers and coupling agents are added so as to achieve an improvement in the impact resistance of the coating.
  • the toughener is also an expensive and expensive to produce block polymers.
  • oleophilic and hydrophobic resins for example, epoxy resins and silicone resins.
  • the coated particles improve the oil yield and reduce the amount
  • a disadvantage is the complicated process.
  • various resins such as phenolic resins are used, for example, as reinforcing fillers
  • US5422183A discloses particles for use as support materials in fracking processes, which also has a two-layered structure
  • US20140124200A discloses the use of hybrid materials made by chemically combining organic resins and silicone resins for coating support materials.
  • the disadvantage here is the use of expensive silicone resins, an additional, complex process for chemical modification and difficult to control product quality in the reaction of two branched polymers.
  • Coatings that use a reaction resin, which in itself already have a relatively low brittleness for example, epoxy resins.
  • W02010060861A1 describes, for example, a homogeneous reaction resin that a
  • Epoxy resin at least one organopolysiloxane homogeneously distributed by means of a silicone organocopolymer which as
  • the object of the present invention was therefore to provide a suitable method for toughening the very brittle phenolic and melamine reactive resins and providing them of cost-effective coating compositions for proppants, a process for coating proppant and the
  • the reactive resin compositions according to the invention comprise (A) 80-99.8% by weight of at least one reactive resin
  • (B) has at least 3 consecutive Si-O units
  • R 1 contains at least 4 atoms selected from the group of C, N, P, O and S, and in R 1 at least 2 of these atoms must be C, and
  • (B) is in flowable form at 20 ° C, or by heating in a temperature range up to 250 ° C
  • the critical stress intensity factor is the Klc value of the invention
  • Reactive resin composition at least 0.55 MN / m 3 2 ,
  • the Tg ( glass transition temperature) of the invention
  • Reactive resin composition is preferably in the range 0 ° C to 250 ° C, preferably in the range 50 ° C to 230 ° C, more preferably in the range 80 ° C to 180 ° C.
  • Tg is defined here as the maximum of tan delta.
  • Reactive resin composition only a reactive resin (A).
  • the reactive resins (A) must have a solid non-sticky
  • the coating can be essentially
  • Coating can also be only partially cured or provided with other reactive groups, so that a
  • Suitable reaction resins (A) according to the invention are all phenolic and melamine resins which are provided with a sufficient number of suitable reactive groups for a curing reaction.
  • Reaction resins (A) which preferably condensation products of aldehydes, e.g. Formaldehyde, with melamine, or with phenol. Curing is usually carried out by increasing the temperature with elimination of water.
  • reaction resins (A) but also all others which are suitable for the production of thermosetting plastics, can be modified in the manner proposed according to the invention and can be obtained according to
  • thermosets with significantly improved resistance to breakage and impact, with other essential properties characteristic of the thermosets, such as strength, heat resistance and chemical resistance, in the
  • the preferred reactive resins (A) are the phenol-formaldehyde resins. These reactive resins (A) include thermosetting ones
  • Resole type phenolic resins and phenolic novolac resins which can be rendered heat reactive by the addition of catalyst and formaldehyde.
  • the reactive resins (A) can either be completely cured during the coating of the proppant particles be cured or only partially cured. Supporting agents with only partially hardened coating harden only after the
  • Particularly preferred reactive resins (A) are phenol novolak resins. These are available for example from Plastics
  • Hexamethylenetetramine is the preferred material as (C) for this function because it serves as both catalyst and formaldehyde source.
  • (A) is used in amounts of at least 80 wt .-%, preferably of at least 88 wt .-%, particularly preferably at least 94 wt .-% and in amounts of at most 99.8 wt .-% and preferably at most 99.5 Weight%.
  • Reactive resin composition only an organopolysiloxane (B).
  • (B) preferably has at least 5, more preferably at least 10, consecutive Si-O units.
  • the ratio of the sum of the C atoms to the sum of the Si atoms in (B) is at least 2.05, preferably at least 2.1 and more preferably at least 3 and preferably at most 40, more preferably at most 20, particularly preferably at most 10.
  • Linear or cyclic (B) may be slightly branched or slightly bridged by an organic radical.
  • the average number of bridging or Branching sites per molecule is preferably -S 4, preferably -S 2, particularly preferably -S 1, very particularly preferably ⁇ 1,
  • (B) is preferably a linear organopolysiloxane.
  • the average number of Si atoms per molecule (B) is preferably less than 1000, preferably less than 200, particularly preferably less than 100.
  • (B) is used in amounts of at least 0.2 wt .-% and at most 20 wt .-%. Preferably from at least 0.5 wt .-% and at most 12 wt .-% and particularly preferably of at most 6 wt. -%.
  • (B) Another important property of (B) is that it is in a flowable form at 20 ° C, or is meltable by heating in a temperature range up to 250 ° C, and thereby can be made into a flowable form.
  • Reactive resin composition means that they are in a physical state of aggregation permitting distribution on the surface of the proppant (made flowable by preheating to 250 ° C or in one
  • the organic radical R 1 has at least 4 atoms, preferably at least 6 atoms, more preferably at least 7 atoms selected from the group of C, N, P, O and S, and of which at least 2 of these atoms are C, are preferred at least 3 of these atoms are C.
  • non-substituted radicals R 1 are alkyl radicals, such as n-butyl, iso-butyl, tert. Butyl, n-pentyl, iso-pentyl, neo-pentyl, tert. Pentyl radical, hexyl radicals, such as the n-hexyl radical, heptyl radicals, such as the n-heptyl radical, octyl radicals, such as the n-octyl radical and iso-octyl radicals, such as the 2,2,4-trimethylpentyl radical, nonyl radicals, such as the n-nonyl radical,
  • Decyl radicals such as the n-decyl radical
  • dodecyl radicals such as the n-dodecyl radical
  • octadecyl radicals such as the n-octadecyl radical
  • Alkenyl radicals such as cyclopentyl, cyclohexyl, cycloheptyl radicals and methylcyclohexyl radicals;
  • Aryl radicals such as the phenyl-naphthyl and anthryl and phenanthryl radicals;
  • Alkaryl radicals such as o-, m-, p-tolyl, xylyl and
  • Ethylphenyl radicals Aralkyl radicals, such as the benzyl radical, the alpha- and the ß-phenylethyl radical.
  • non-substituted R 1 are the following radicals phenyl, a-phenylethyl, n-octyl, n-dodecyl, n-hexadecyl, n-octadecyl.
  • substituted radicals R 1 are haloalkyl radicals, such as the perfluorohexylethyl radical; Haloaryl radicals, such as the o-, m- and p-chlorophenyl radical, and all unsubstituted radicals R 1 mentioned above which are substituted by the following groups: mercapto groups, epoxy-functional groups,
  • Aminoethylamino groups iso-cyanato groups, aryloxy groups, acryloxy groups, methacryloxy groups, hydroxy groups and
  • substituted R 1 is the 10-carboxydecyl radical. Further examples of substituted radicals R are short
  • Alkyl radicals such as the methyl, ethyl, n-propyl, iso-propyl
  • alkenyl radicals such as the vinyl and the allyl radical, preferably with mercapto groups, epoxy-functional groups, carboxy groups, keto groups, enamine groups, amino groups, Aminoethylamino phenomenon, iso Cyanato groups, aryloxy groups, acryloxy groups, methacryloxy groups, hydroxy groups and
  • Halogen groups may be substituted, with the proviso that the substituted radicals R 1 contains at least 4 atoms selected from the group of C, N, P, 0 and S, wherein at least two C atoms must be included.
  • Preferred substituted radicals R 1 are hydroxypropyl and mercaptopropyl.
  • R 2 is a divalent hydrocarbon radical having 1 to 10
  • Ether oxygen atom may be interrupted
  • R 3 is a hydrogen atom or a monovalent one
  • Preferred epoxy radicals are the glycidoxypropyl radical and the 3,4-epoxycyclohexylethyl radical.
  • R 1 are amino radicals of the general formula
  • R 7 is a hydrogen atom, an alkyl radical having 1 to 8
  • R 8 is a divalent hydrocarbon radical having 1 to 6
  • Carbon atoms preferably an alkylene radical having 1 to 6 carbon atoms,
  • n 0, 1, 2, 3 or 4, preferably 0 or 1.
  • Further preferred substituted radicals R are polyether radicals of the general formula
  • R 9 denotes a hydrocarbon radical having 1 to 6 carbon atoms or H, preferably Me or H,
  • u is 0 or an integer from 1 to 16, preferably 1 to 4,
  • v is 0 or an integer from 1 to 35, preferably 1 to 25, and
  • w is 0 or an integer from 1 to 35, preferably 1 to 25,
  • x is 0 or an integer from 1 to 35, preferably 1 to 25
  • R 1 are organic polymer radicals with formation of a polysiloxane-containing copolymer. These copolymers may be block or graft copolymers. Examples of suitable organic parts include, but are not limited to, polycaprolactone, polyesters, polyvinyl acetates, polystyrenes, polymethyl methacrylates.
  • the organic part is preferably a (co) polymer
  • Vinyl acetate, methyl methacrylate or aliphatic polyester Particularly preferred is polycaprolactone.
  • the block copolymers contain a siloxane unit having a molecular weight of 1,000-10,000 g / mol, preferably 1,500-5,000 g / mol, more preferably 2,000-4,000 g / mol.
  • radicals R are polyether radicals, epoxy particularly preferably the glycidoxypropyl radical and the 3,4- Epoxycyclohexylethyl radical, and organic polymer radicals, particularly preferably a polycaprolactone radical.
  • Another object of the present invention is the
  • Reactive resins are suitable, is described for example in the following textbook: Polymer Handbook. Volume 2, 4 Ed .; J. Brandrup, E.H. Immergut, E.A. Grulke; John Wiley & Sons, Inc., 1999 (ISBN 0-471-48172-6).
  • Suitable mixers are, for example, laboratory stirrers,
  • Plant mixer, or dissolver, or rotor-stator systems, or even extruders, rollers, 3-roller chair, etc. can dissolve when dispersed in whole or in part in (A). Undissolved components are present as the second phase in (A) dispersed. The mean size of these domains is
  • Another object of the present invention is the
  • Coatings and for the production of molded parts, workpieces and foams Coatings and for the production of molded parts, workpieces and foams.
  • inventive Reactive resin composition used for coating proppants.
  • Another object of the present invention is the
  • Reactive resin compositions are used.
  • inventive reactive resin composition melted by heating to 250 ° C and therefore flowable together with or without at least one curing agent (C) and with or without at least one additive (D), applied to the proppant
  • the order of addition of the components (A), (B), (C) and (D) is variable, with the proviso that the component (B) is mixed before a substantial hardening of the reactive resin occurs. This has the advantage that a short-term adaptation of the ratios of (A) to (B) in a simple and straightforward way can be done at any time.
  • Supporting means is thus characterized in that
  • coated according to the invention support (A) with a suitable solvent, proppant and (B).
  • Mixture can optionally hardener (C) and possibly different Additives (D) are added. Subsequently, the solvent is evaporated off and the so coated adhesives are cured.
  • the order of addition of components (A), (B), (C) and (D) is variable.
  • a suitable proppant such as sand is preheated to about 170-260 ° C. In a mixer is then the
  • Reactive resin composition according to the invention a suitable hardener (C) and optionally various additives (D) are added.
  • a suitable proppant such as sand is preheated to about 170-260 ° C.
  • a suitable hardener C
  • optionally various additives D
  • this layer is first partially or completely cured.
  • Reactive resin composition applied and partially or fully cured again.
  • Reactive resin composition in portions in several steps without substantial intermediate curing of the individual portions and only at the end of a partial or complete curing. This therefore only leads to a single layer.
  • Suitable proppants are known to those skilled in the art for a long time and can for the inventive Coating be used.
  • Supporting agents are usually hard, high-strength particles such as sand or gravel from rocks such as limestone, marble, dolomite, granite, etc., but also glass beads, ceramic particles, ceramic balls and
  • the proppant particles have a substantially spherical or spherical shape, since they leave enough space for the crude oil or gas
  • sand is particularly preferably used as a proppant.
  • the proppant particles have an average size of 5,000 to 50 ⁇ m, more preferably one
  • Suitable hardeners are known to those skilled in the art for a long time and are according to the
  • a preferred novolak curing agent (C) is urotropin. (C) and thus also urotropin is typically used in amounts of between 8 and 20% by weight, based on the amount of reactive resin composition according to the invention.
  • urotopin is applied as an aqueous solution to the melt of the reactive resin. Such methods are also known to those skilled in the art and described for example in US4732920.
  • Suitable additives (D) have also long been known to the person skilled in the art. Non-exhaustive examples are anti-static agents, release agents, adhesion promoters, etc.
  • Suitable proppants, hardeners (C) and additives (D) are described for example in US4732920 and US2007 / 0036977 AI.
  • the type and specification of the proppant, type and specification of the reactive resin (A), organopolysiloxane (B), hardener (C) and optionally additives (D) the type of mixing and coating process must Order of addition of the
  • a change in the proppant may require an adjustment of the coating process and / or the hardener used (C) and additives (D).
  • the surface of the proppant may be completely or partially coated. Preferably appear in the investigation with the
  • Reactive resin composition coated more preferably at least 50%.
  • the essential part of the coating on the proppant according to the invention is 0.1 to 100 ⁇ thick, preferably 0.1 to 30 ⁇ , more preferably 1 to 20 ⁇ . Preference is given to the proppants of the invention having less than three layers of the invention
  • Reactive resin composition coated Particularly preferred with only one layer.
  • the reactive resin composition according to the invention is preferably used in amounts of 0.1-20% by weight, based on the weight of the
  • Supporting agent used Preferably from 0.5-10% by weight and more preferably from 1-5% by weight.
  • Another object of the present invention is the
  • the reactive resin composition according to the invention has
  • the cured reactive resin composition of the present invention has improved toughness, elasticity and ductility at the same hardness. This makes it more resistant
  • the reactive resin composition of the present invention has improved as a hardened coating for proppant
  • Supporting agent more resistant to stress such as
  • Another advantage of the coating according to the invention lies in its deformability, so that it often does not break even when breaking the brittle proppant grains themselves and thus encloses or holds together the resulting fines such as a plastic shell and thus their total release
  • the oil or gas flow can be maintained longer. This results in decisive economic benefits and environmental protection.
  • Polysiloxane-polycaprolactone block copolymer of melting point 50 ° C and about 30-50 Si-O units) were added and stirred at 420 rpm for 10 minutes.
  • the liquid mass is poured hot onto a PTFE film and mechanically comminuted, thus producing a granulate.
  • SIPELL® RE 63 F a polydimethylsiloxane having glycidoxypropylmethylsiloxy units and about 100-160 Si-O units;
  • silicone oil 1 a trimethylsiloxy-endstopped polydimethylsiloxane having about 75-85 Si-O units consisting of dimethylsiloxy units and an average of 2.5 glycidoxypropylmethylsiloxy units and an average of 2.5
  • silicone oil 2 an a, co-functional silicone oil having about 15-20 Si-O units and hydroxy (polyethyleneoxy) end groups of about 10
  • organopolysiloxanes (B) uniformly and finely in the reactive resin. If a second phase is formed, this is essentially in the form of spherical droplets.
  • the non-inventive polysiloxane from Comparative Example VI is not homogeneously dispersible and forms unevenly distributed streaks in the reactive resin.
  • Comparative Example C2 is unmodified novolac “Resin 14772" (Plastics Engineering Company, Sheboygan, USA)
  • Example 6 The solutions of Example 6 are 12 mm high in one
  • Klc value increased (determination analogous to the above-mentioned description), which represents a measure of improved toughness.
  • inventively modified resins are more elastic and have a reduced Tg compared to the unmodified phenolic resin.
  • Q-PANEL test panels on the brushed side were cleaned 3 times with acetone and then vented for 1 h in a fume hood. Subsequently, 3 ml of the corresponding phenolic resin solution from Example 6 were added to each plate and spread with a 100 ym knife and then the solvent was evaporated in a fume hood overnight.
  • the samples were placed in a cold oven, heated to 160 ° C with rinsing with nitrogen within 3 hours, kept at this temperature for 2 h and cooled to 23 ° C overnight.
  • Coating be considered in isolated form. One receives a statement to the elasticity, impact resistance and
  • Comparative Examples an approximately 50 ⁇ thick, hardened layer of the unmodified resin Resin 14772 (Plastics Engineering Company, Sheboygan, USA) and the non-inventive resin of Comparative Example VI.
  • the coated panels were tested on an Erichsen ball impact tester, Model 304-ASTM, and the results were visually evaluated by a trained examiner: To do this, drop a ball onto the back of the panel from a defined, variable height of fall (each duplicate at different locations). The impact energy is calculated from the height of fall multiplied by
  • the cured coatings of the present invention have significantly improved resilience, impact strength, and fracture toughness compared to the unmodified
  • extrinsic impact modifiers are not suitable for the very brittle, glassy reactive resins such as phenolic resins
  • Reactive resin composition causes a more uniform and effective coating of the surface of the proppant.
  • Example 8 was tested according to DIN EN ISO 13503-2 at 14000 PSI and 18000 PSI pressure. The result is shown in Table 4. Table 4
  • modified reactive resins did not allow a fundamental conclusion that this automatically leads to an improvement in the pressure resistance.

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Abstract

L'invention concerne des compositions de résine active modifiées et leur utilisation comme produits de revêtement pour des matériaux de soutènement qui sont utilisés en fracturation hydraulique.
PCT/EP2017/051337 2016-01-28 2017-01-23 Compositions de résine active modifiées et leur utilisation pour le revêtement d'agents de soutènement WO2017129529A1 (fr)

Priority Applications (5)

Application Number Priority Date Filing Date Title
US16/071,991 US11078410B2 (en) 2016-01-28 2017-01-23 Modified reactive resin compositions and use thereof for coating propping agents
JP2018539327A JP2019510096A (ja) 2016-01-28 2017-01-23 改質反応性樹脂組成物、およびプロパント剤コーティング用のその使用
CN201780007823.9A CN108495909A (zh) 2016-01-28 2017-01-23 改性的反应型树脂组合物及其用于涂覆支撑剂的用途
EP17701463.6A EP3408346A1 (fr) 2016-01-28 2017-01-23 Compositions de résine active modifiées et leur utilisation pour le revêtement d'agents de soutènement
KR1020187024413A KR102104024B1 (ko) 2016-01-28 2017-01-23 개질된 반응성 수지 조성물 및 프로판트제를 코팅하기 위한 이의 용도

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Application Number Priority Date Filing Date Title
EP16051792 2016-01-28
EPPCT/2016/051792 2016-01-28

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