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  • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
  • C08G18/00—Polymeric products of isocyanates or isothiocyanates
  • C08G18/02—Polymeric products of isocyanates or isothiocyanates of isocyanates or isothiocyanates only
  • C08G18/022—Polymeric products of isocyanates or isothiocyanates of isocyanates or isothiocyanates only the polymeric products containing isocyanurate groups
• • C—CHEMISTRY; METALLURGY
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  • C08G18/00—Polymeric products of isocyanates or isothiocyanates
  • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
  • C08G18/08—Processes
  • C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
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  • C08G18/00—Polymeric products of isocyanates or isothiocyanates
  • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
  • C08G18/08—Processes
  • C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
  • C08G18/12—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step using two or more compounds having active hydrogen in the first polymerisation step
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  • C08G18/00—Polymeric products of isocyanates or isothiocyanates
  • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
  • C08G18/08—Processes
  • C08G18/16—Catalysts
  • C08G18/166—Catalysts not provided for in the groups C08G18/18 - C08G18/26
  • C08G18/168—Organic compounds
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  • C08G18/00—Polymeric products of isocyanates or isothiocyanates
  • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
  • C08G18/08—Processes
  • C08G18/16—Catalysts
  • C08G18/18—Catalysts containing secondary or tertiary amines or salts thereof
  • C08G18/1825—Catalysts containing secondary or tertiary amines or salts thereof having hydroxy or primary amino groups
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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  • C08G18/00—Polymeric products of isocyanates or isothiocyanates
  • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
  • C08G18/08—Processes
  • C08G18/16—Catalysts
  • C08G18/18—Catalysts containing secondary or tertiary amines or salts thereof
  • C08G18/1875—Catalysts containing secondary or tertiary amines or salts thereof containing ammonium salts or mixtures of secondary of tertiary amines and acids
• • 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
  • C08G18/00—Polymeric products of isocyanates or isothiocyanates
  • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
  • C08G18/08—Processes
  • C08G18/16—Catalysts
  • C08G18/22—Catalysts containing metal compounds
  • C08G18/225—Catalysts containing metal compounds of alkali or alkaline earth metals
• • C—CHEMISTRY; METALLURGY
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  • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
  • C08G18/00—Polymeric products of isocyanates or isothiocyanates
  • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
  • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
  • C08G18/40—High-molecular-weight compounds
  • C08G18/48—Polyethers
  • C08G18/4804—Two or more polyethers of different physical or chemical nature
  • C08G18/4812—Mixtures of polyetherdiols with polyetherpolyols having at least three hydroxy 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
  • C08G18/00—Polymeric products of isocyanates or isothiocyanates
  • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
  • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
  • C08G18/40—High-molecular-weight compounds
  • C08G18/48—Polyethers
  • C08G18/4825—Polyethers containing two hydroxy 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
  • C08G18/00—Polymeric products of isocyanates or isothiocyanates
  • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
  • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
  • C08G18/40—High-molecular-weight compounds
  • C08G18/48—Polyethers
  • C08G18/4829—Polyethers containing at least three hydroxy 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
  • C08G18/00—Polymeric products of isocyanates or isothiocyanates
  • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
  • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
  • C08G18/40—High-molecular-weight compounds
  • C08G18/48—Polyethers
  • C08G18/4833—Polyethers containing oxyethylene units
  • C08G18/4837—Polyethers containing oxyethylene units and other oxyalkylene units
  • C08G18/4841—Polyethers containing oxyethylene units and other oxyalkylene units containing oxyethylene end 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
  • C08G18/00—Polymeric products of isocyanates or isothiocyanates
  • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
  • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
  • C08G18/72—Polyisocyanates or polyisothiocyanates
  • C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
  • C08G18/75—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic
  • C08G18/751—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring
  • C08G18/752—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group
  • C08G18/753—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group containing one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group having a primary carbon atom next to the isocyanate or isothiocyanate group
  • C08G18/755—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group containing one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group having a primary carbon atom next to the isocyanate or isothiocyanate group and at least one isocyanate or isothiocyanate group linked to a secondary carbon atom of the cycloaliphatic ring, e.g. isophorone diisocyanate
• • 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
  • C08G18/00—Polymeric products of isocyanates or isothiocyanates
  • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
  • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
  • C08G18/72—Polyisocyanates or polyisothiocyanates
  • C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
  • C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
  • C08G18/7657—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings
  • C08G18/7664—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings containing alkylene polyphenyl groups
  • C08G18/7671—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings containing alkylene polyphenyl groups containing only one alkylene bisphenyl group
• • 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
  • C08G18/00—Polymeric products of isocyanates or isothiocyanates
  • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
  • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
  • C08G18/72—Polyisocyanates or polyisothiocyanates
  • C08G18/77—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur
  • C08G18/78—Nitrogen
  • C08G18/79—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates
  • C08G18/791—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing isocyanurate groups
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
  • C08K3/00—Use of inorganic substances as compounding ingredients
  • C08K3/01—Use of inorganic substances as compounding ingredients characterized by their specific function
  • C08K3/013—Fillers, pigments or reinforcing additives
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
  • C08K3/00—Use of inorganic substances as compounding ingredients
  • C08K3/02—Elements
  • C08K3/04—Carbon
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
  • C08K3/00—Use of inorganic substances as compounding ingredients
  • C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
  • C08K3/20—Oxides; Hydroxides
  • C08K3/22—Oxides; Hydroxides of metals
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
  • C08K3/00—Use of inorganic substances as compounding ingredients
  • C08K3/34—Silicon-containing compounds
  • C08K3/36—Silica
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
  • C08K5/00—Use of organic ingredients
  • C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
  • C08K5/0016—Plasticisers
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
  • C08L75/00—Compositions of polyureas or polyurethanes; Compositions of derivatives of such polymers
  • C08L75/04—Polyurethanes
  • C08L75/08—Polyurethanes from polyethers
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
  • C08K3/00—Use of inorganic substances as compounding ingredients
  • C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
  • C08K3/20—Oxides; Hydroxides
  • C08K3/22—Oxides; Hydroxides of metals
  • C08K2003/2206—Oxides; Hydroxides of metals of calcium, strontium or barium
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
  • C08K3/00—Use of inorganic substances as compounding ingredients
  • C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
  • C08K3/20—Oxides; Hydroxides
  • C08K3/22—Oxides; Hydroxides of metals
  • C08K2003/2227—Oxides; Hydroxides of metals of aluminium

Definitions

• Natural and synthetic rubber is obtained through vulcanization, leading to durable elastomers.
• Rubber has a low glass transition temperature and a good dimensional stability with a high elastic recovery after pressure.
• rubber is particularly suitable for elastic seals or dampening materials, for example as a component of shock absorbers in vehicle construction. Over time, however, rubber tends to become brittle due to oxidation by air and loses its elasticity, which means that the rubber has to be replaced regularly.
• Polyurethanes are elastic plastics that are widely used in industry. They have a good elasticity and an adjustable hardness from soft-elastic to tough-elastic, i.e.
• the term consideringurethane group” refers to a functional group of the
• the content of urethane groups in the cured polymer is being calculated from the content of hydroxyl groups which have reacted with isocyanate groups thereby forming urethane groups in the cured polymer, whereby the molecular weight of the urethane group is 59 g/mol (-NH-CO-O-).
• the molar content of urethane groups within the cured polymer fully corresponds to the molar content of hydroxyl groups of the polyols employed in the synthesis of the isocyanate-functional polymer to be cured within the polyisocyanurate plastic, from which the mass percentage of urethane groups within this cured polymer can be calculated.
• the term crizomycin-content“ refers to the content of isocyanate groups in weight-% of a molecule, a polymer or a composition.
• room temperature refers to a temperature of 23°C.
• polyether chains consisting of oxy-1 , 2-propylene units or of poly(oxy-1 ,2-propylene) chains which are endcapped with a certain amount of oxyethylene units.
• Such materials are readily available and of high hydrophobicity, allowing polyisocyanurate plastics of high dimensional and hydrolytic stability.
• the polyether chains consist of oxy-1 ,2-propylene units.
• the content of isocyanurate groups, in relation to the total polymer is 1 to 6 weight-%, preferably 1 .2 to 5 weight-%, more preferably 1.4 to 4 weight-%, particularly 1 .5 to 3 weight-%.
• the cured polymer contains moieties after removal of the two isocyanate groups selected from the group consisting of the isomeric diphenylmethane diisocyanates (MDI), the isomeric toluene diisocyanates (TDI), naphthalene-1 ,5- diisocyanate (NDI), 1 ,5-pentane diisocyanate (PDI), 1 ,6-hexane diisocyanate (HD I), isophorone diisocyanate (IPDI), the isomeric dicyclohexylmethane diisocyanates (H12MDI) and mixtures thereof.
• MDI isomeric diphenylmethane diisocyanates
• TDI isomeric toluene diisocyanates
• NDI naphthalene-1 ,5- diisocyanate
• PDI naphthalene-1 ,5- diisocyanate
• PDI 1 ,5-p
• the amount of fillers, in relation to the total plastic is at least 50 weight-%, preferably at least 60 weight-%, more preferably at least 70 weight-%, particularly at least 80 weight-%, whereby the poly- isocyanurate plastic optionally further contains at least one plasticizer.
• Preferred fillers for such a high filler load are mineral fillers with a mean particle size of more than 1 pm.
• fillers selected from graphite, aluminium oxide, aluminium hydroxide, boron nitride, aluminium nitride, magnesium oxide, magnesium hydroxide and zinc oxide, and
• Such a plastic has a particularly high thermal conductivity.
• a polyisocyanurate plastic which contains, in relation to the total plastic, an amount of carbon black of at least 20 weight-%, preferably at least 30 weight-%.
• a plastic is particularly suitable for the use as a shock absorbing plastic. It has a particularly high strength and toughness and is particularly suitable for encasing the steel springs of shock absorbers for vehicles. It enables durable shock absorbing properties and a high dimensional stability after compression in a broad temperature range.
• Such a polyisocyanate plastic has particularly high shock absorbing properties.
• the layer thickness of the inventive polyisocyanate plastic is at least 1 mm, preferably at least 2 mm, more preferably at least 4 mm, particularly at least 5 mm, whereby “layer thickness” means the smallest dimension in relation to length, width and height of the polyisocyanurate plastic.
• Such a plastic has a high dimensional stability in connection with a low compression set and is able to dampen vibrations and other mechanical deformations effectively.
• the inventive polyisocyanate plastic has a particularly high dimensional stability with a low compression set.
• the deformation after compression at 70 °C is less than 50 %, preferably less than 40 %, particularly less than 30 %, determined with a cylindrical sample of 13 mm in diameter and 6 mm in height after compressing the sample by 25 % in height to 4.5 mm at 70 °C for 94 hours, followed by cooling the compressed sample to room temperature, releasing the pressure and measuring the loss in height in % based on the compressed height of 1 .5 mm.
• composition which is provided in step i) contains at least one isocyanate- functional polymer with at least 75 weight-% of polyether chains, 1 to 5.2 weight-% of urethane groups and 0.7 to 4 weight-% of isocyanate groups.
• the composition contains at least one drying agent, particularly calcium oxide. Calcium oxide reacts with water to form calcium hydroxide, thereby preventing water, which might be contained in the fillers, from reacting with isocyanate groups upon storage of the composition.
• Catalysts which are solid at room temperature are preferably used as a solution in a suitable liquid, preferably in glycol or diethyleneglycol and/or in a plasticizer.
• the amount of the added trimerisation catalyst, in relation to the total polyisocya- nurate plastic which is obtained, is preferably 0.01 to 5 weight-%, more preferably 0.02 to 3 weight-%, particularly 0.05 to 1 weight-%.
• the catalyst in step ii) can be added by any possible mixing procedure.
• the addition of the catalyst in step ii) is performed by a static or a dynamic mixing procedure.
• the catalyst is added in a diluted form, particularly as part of a catalyst component which further contains plasticizers and optionally fillers.
• the curing in step iii) can be performed at ambient or at elevated temperatures, preferably at a temperature of 5 to 100 °C, more preferably 10 to 90 °C, particularly 15 to 80 °C.
• the composition with the mixed-in catalyst is preferably in contact with one or more than one substrates, preferably moisture-tight substrates, which cover substantially the whole surface of the mixed material.
• the surface of the mixed material is preferably not or only to a minimal extent exposed to moisture from the air during curing.
• Figure 1 shows the curves of the storage modulus and the loss modulus of example 2 vs temperature, determined with DMTA measurement as described.
• Table 2 Composition and properties of Compositions C-1 to C-5.
• DMTA measurements were done using a Rheoplus MCR 302 instrument from Anton Paar on striped samples (width 2.5 mm, length 8.5 mm, thickness 2 mm), which were cut from the cured film prepared to determine the mechanical properties.
• the measurement conditions were: measurement in shear mode, excitation frequency of 1 Hz and heating rate of 5 K/min.
• the samples were cooled to -100°C and heated to 200°C with determination of the storage modulus and the loss modulus, whereby the temperature at the maximum of the loss modulus was read as the Tg value (glass transition temperature).
• Table 7 Dimensional stability after compression at 70 °C of the Examples 1 and 2 in comparison to a commercial polyurethane material.
• Table 8 Pot life of Example 3 at different catalyst concentrations and temperatures.
• the Shore A hardness was determined according to DIN 53505 with cylindrical samples of 20 mm diameter and a thickness of 6 mm which had been cured covered by a PTFE-coated foil and a metal lid for 7 days in standard climate. The aspect was visually determined at samples which were prepared for the Shore A measurement by judging the surface and cutting them to expose the material inside.
• the thermal conductivity was determined according to ASTM D5470-12 on samples cured during 7 days under standard climatic conditions.
• a TIM (thermal interface material) testing device obtained from Zentrum fur Warmemanagement, Stuttgart, Germany
• Sample dimensions were: Diameter 30 mm, thicknesses 2 mm and 6 mm.
• the pressure parameters of the measurements were 1 , 2, 3, 5, 7, 10 bar.

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• Chemical & Material Sciences (AREA)
• Health & Medical Sciences (AREA)
• Chemical Kinetics & Catalysis (AREA)
• Medicinal Chemistry (AREA)
• Polymers & Plastics (AREA)
• Organic Chemistry (AREA)
• Polyurethanes Or Polyureas (AREA)
• Compositions Of Macromolecular Compounds (AREA)

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• 2023
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  • 2023-09-08 WO PCT/EP2023/074745 patent/WO2024052537A1/en not_active Ceased
  • 2023-09-08 EP EP23768815.5A patent/EP4587494A1/de active Pending
  • 2023-09-08 CN CN202380055618.5A patent/CN119585332A/zh active Pending
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