WO2019063294A1 - Composites de polyuréthane - Google Patents

Composites de polyuréthane Download PDF

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Publication number
WO2019063294A1
WO2019063294A1 PCT/EP2018/074631 EP2018074631W WO2019063294A1 WO 2019063294 A1 WO2019063294 A1 WO 2019063294A1 EP 2018074631 W EP2018074631 W EP 2018074631W WO 2019063294 A1 WO2019063294 A1 WO 2019063294A1
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WO
WIPO (PCT)
Prior art keywords
diphenylmethane diisocyanate
polyurethane composition
polyurethane
composition according
isocyanate
Prior art date
Application number
PCT/EP2018/074631
Other languages
English (en)
Inventor
Zhen Yu QIAN
Xue Dong Li
Yang Chun ZHOU
Jian Feng XU
Original Assignee
Basf Se
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 Basf Se filed Critical Basf Se
Priority to KR1020207012741A priority Critical patent/KR20200062302A/ko
Priority to CN201880061079.5A priority patent/CN111183166B/zh
Priority to AU2018340584A priority patent/AU2018340584A1/en
Publication of WO2019063294A1 publication Critical patent/WO2019063294A1/fr

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Classifications

    • 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
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29C—SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
    • B29C70/00—Shaping composites, i.e. plastics material comprising reinforcements, fillers or preformed parts, e.g. inserts
    • B29C70/04—Shaping composites, i.e. plastics material comprising reinforcements, fillers or preformed parts, e.g. inserts comprising reinforcements only, e.g. self-reinforcing plastics
    • B29C70/28—Shaping operations therefor
    • B29C70/40—Shaping or impregnating by compression not applied
    • B29C70/50—Shaping or impregnating by compression not applied for producing articles of indefinite length, e.g. prepregs, sheet moulding compounds [SMC] or cross moulding compounds [XMC]
    • B29C70/52—Pultrusion, i.e. forming and compressing by continuously pulling through a die
    • 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
    • C08G18/10—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
    • 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
    • C08G18/64—Macromolecular compounds not provided for by groups C08G18/42 - C08G18/63
    • C08G18/6415—Macromolecular compounds not provided for by groups C08G18/42 - C08G18/63 having nitrogen
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
    • C08J5/04—Reinforcing macromolecular compounds with loose or coherent fibrous material
    • C08J5/0405—Reinforcing macromolecular compounds with loose or coherent fibrous material with inorganic fibres
    • C08J5/043—Reinforcing macromolecular compounds with loose or coherent fibrous material with inorganic fibres with glass fibres
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J9/00—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2375/00—Characterised by the use of polyureas or polyurethanes; Derivatives of such polymers
    • C08J2375/04—Polyurethanes
    • C08J2375/06—Polyurethanes from polyesters
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2375/00—Characterised by the use of polyureas or polyurethanes; Derivatives of such polymers
    • C08J2375/04—Polyurethanes
    • C08J2375/08—Polyurethanes from polyethers

Definitions

  • the present invention relates to a polyurethane composition, a polyurethane composite comprising said polyurethane composition and a reinforced material, and an article produced from said polyurethane composite.
  • Polyurethane (PU) composites are nowadays used in many applications because of their broad properties. Particularly, polyurethane composites exhibit excellent performance and unique advantages in pultrusion process compared with the traditional structure materials such as concrete, steel, aluminum, and conventional thermosetting resins.
  • the pultrusion process is a continuous process for producing fiber-reinforced profiles, wherein the fibers are impregnated by polyurethane composition in an open bath or in a closed injection box, and then shaped and hardened.
  • polyurethane has various advantages, its relatively short processing time makes it challenging to produce large size parts by pultrusion process, such as bridge components, large artificial wood, large pole structure, complex window profile, reefer container, etc.
  • CN104045806A discloses a polyurethane composition for preparing a polyurethane com- posite, comprising: a) a polyisocyanate component, wherein the polyisocyanate component comprises 2,2'-diphenylmethane diisocyanate and 2,4'-diphenylmethane diisocyanate; and b) an isocyanate reactive component.
  • US2013/0309924A1 discloses a reinforced pultruded polyurethane obtainable via reacting A) polyether polyols, B) epoxides with C) organic polyisocyanates.
  • US8,663,414B2 discloses a pultrusion resin system, comprising a) a di- or polyisocyanate, b) a compound having at least two groups reactive toward an isocyanate, c) a catalyst, d) a polybasic acid having a functionality greater than or equal to 2 and, optionally, e) a further auxiliary or additive, where a boiling point of the polybasic acid is at least 200°C at standard pressure and the polybasic acid is soluble in the compound having at least two groups reactive toward an isocyanate.
  • the present invention provides a polyurethane composition, comprising
  • an isocyanate reactive compound comprising 2,2'-diphenylmethane diisocyanate (2,2'-MDI) and 2,4'- diphenylmethane diisocyanate (2,4'-MDI), and the amount of 2,2'-diphenylmethane diisocyanate is in the range of 10-100wt% based on the total weight of 2,2'-diphenylmethane diisocyanate and 2,4'-diphenylmethane diisocyanate.
  • the present invention provides a polyurethane composite, comprising:
  • the present invention also provides an article produced from said polyurethane composite above.
  • the polyurethane compositions of the present invention have prolonged gel time such that the polyurethane compositions are particularly suitable for producing large size parts such as bridge components, large artificial wood, large pole structure, complex window profile, reefer container, etc.
  • a polyurethane composition comprising: (1 ) an isocyanate; and (2) an isocyanate reactive compound; wherein the isocyanate comprises 2,2'-diphenylmethane diisocyanate and 2,4'- diphenylmethane diisocyanate, and the amount of 2,2'-diphenylmethane diisocyanate is in the range of 10-100wt%, preferably 15-70wt%, more preferably 20-50wt%, still more preferably 20- 30wt% based on the total weight of 2,2'-diphenylmethane diisocyanate and 2,4'- diphenylmethane diisocyanate.
  • the total amount of 2,2'-diphenylmethane diisocyanate and 2,4'-diphenylmethane diisocyanate is in the range of 50-100wt%, preferably 60-90wt%, more preferably 60-80wt% based on the total weight of the isocyanate.
  • the polyurethane composition can be compact or foam.
  • the polyurethane composition has a free rise density of from 30g/l to 900g/l.
  • the isocyanate can comprise the mixtures of monomeric diphenylmethane diisocyanates and of diphenylmethane diisocyanate homologs having a greater number of rings (polymeric MDI), tolylene diisocyanate (TDI), for example tolylene diisoyanate isomers such as tolylene 2,4- or 2,6-diisocyanate, or a mixture of these, naphthylene diisocyanate (NDI), or a mixture thereof, preferably 2,2'-diphenylmethane diisocyanate, 2,4'-diphenylmethane diisocyanate, 4,4'- diphenylmethane diisocyanate (4,4'-MDI), polymeric MDI, or combination thereof.
  • polymeric MDI polymeric MDI
  • TDI tolylene diisocyanate
  • NDI naphthylene diisocyanate
  • the isocyanate reactive compound also termed “polyols” for the purposes of this invention, can comprise any of the compounds having at least two groups reactive toward isocyanates, examples being OH, SH, NH, Nhb, -COON, and CH-acidic groups.
  • Isocyanate reactive compounds are known to the person skilled in the art and are described by way of example in "Kunststoffhandbuch, 7, Polyurethane” [Plastics Handbook, 7, Po- lyurethanes] Carl Hanser-Verlag, 3rd edition, 1993, chapter 3.1 .
  • Examples of the isocyanate reactive compounds are polyetherols or polyesterols.
  • the isocyanate reactive compounds can be polyetherols or polyesterols comprising secondary OH groups, an example being polypropylene oxide.
  • the functionality of these polyetherols or polyesterols is preferably from 2 to 4, particularly preferably from 2 to 3.
  • polyetherols and/or polyesterols having from 2 to 8 hydrogen atoms reactive toward isocyanate and to use low-molecular-weight polyols, such as glycerol, dipropylene glycol, and/or tripropylene glycol.
  • the OH number of these compounds is usually in the range from 30 to 2000 mg KOH/g, preferably in the range from 40 to 1000 mg KOH/g.
  • the average OH number of all of the isocyanate reactive compound used here having at least two groups reactive toward isocyanates is from 100 to 1000 mg KOH/g, preferably from 300 to 900 mg KOH/g.
  • the polyetherols are obtained by known processes, for example via anionic polymerization of alkylene oxides with addition of at least one starter molecule comprising from 2 to 8, preferably from 2 to 6, and particularly preferably from 2 to 4, reactive hydrogen atoms, in the presence of catalysts.
  • Catalysts used can comprise alkali metal hydroxides, such as sodium hydroxide or potassium hydroxide, or alkali metal alcoholates, such as sodium methoxide, sodi- urn ethoxide, potassium ethoxide, or potassium isopropoxide, or, in the case of cationic polymerization, Lewis acids, such as antimony pentachloride, boron trifluoride etherate, or bleaching earth.
  • Other catalysts that can be used are double-metal cyanide compounds, known as DMC catalysts.
  • the alkylene oxides used preferably comprise one or more compounds having from 2 to 4 carbon atoms in the alkylene moiety, e.g. tetrahydrofuran, ethylene oxide, propylene 1 ,2-oxide, butylene 1 ,2-oxide or butylene 2,3-oxide, in each case alone or in the form of a mixture, and preferably propylene 1 ,2-oxide and/or ethylene oxide, in particular propylene 1 ,2-oxide.
  • tetrahydrofuran ethylene oxide
  • propylene 1 ,2-oxide butylene 1 ,2-oxide or butylene 2,3-oxide
  • propylene 1 ,2-oxide and/or ethylene oxide in particular propylene 1 ,2-oxide.
  • starter molecules examples include ethylene glycol, diethylene glycol, glycerol, trimethylolpropane, pentaerythritol, sugar derivatives, such as sucrose, hexitol derivati- ves, such as sorbitol, methylamine, ethylamine, isopropylamine, butylamine, benzylamine, aniline, toluidine, toluenediamine, naphthylamine, ethylenediamine, diethylenetriamine, 4,4'- methylenedianiline, 1 ,3-propanediamine, 1 ,6-hexanediamine, ethanolamine, diethanolamine, triethanolamine, and also other di- or polyhydric alcohols, or di- or polybasic amines.
  • sugar derivatives such as sucrose, hexitol derivati- ves, such as sorbitol, methylamine, ethylamine, isopropylamine, butylamine,
  • polyester alcohols used are mostly produced via condensation of polyhydric alcohols having from 2 to 12 carbon atoms, e.g. ethylene glycol, diethylene glycol, butanediol, trimethylolpropane, glycerol, or pentaerythritol, with polybasic carboxylic acids having from 2 to 12 car- bon atoms, e.g.
  • succinic acid glutaric acid, adipic acid, suberic acid, azelaic acid, sebacic acid, decanedicarboxylic acid, maleic acid, fumaric acid, phthalic acid, isophthalic acid, terephthalic acid, and the isomers of naphthalenedicarboxylic acids, or their anhydrides.
  • hydrophobic substances are substances insoluble in water which comprise a nonpolar organic moiety, and which also have at least one reactive group selected from hydroxy, carboxylic acid, carboxylic ester, or a mixture thereof.
  • the equivalent weight of the hydrophobic materials is preferably from 130 to 1000 g/mol.
  • materials that can be used are fatty acids, such as stearic acid, oleic acid, palmitic acid, lauric acid, or linoleic acid, and also fats and oils, e.g. castor oil, maize oil, sunflower oil, soybean oil, coconut oil, olive oil, or tall oil.
  • the proportion of the hydrophobic substances, based on the total monomer content of the polyester alcohol is preferably from 1 to 30 mol %, particularly preferably from 4 to 15 mol %.
  • the functionality of the polyesterols used is preferably from 1.5 to 5, particularly preferably from 1.8 to 3.5.
  • the isocyanate-reactive compounds comprise po- lyetherols, in particular exclusively polyetherols.
  • the actual average functionality of the po- lyetherols is preferably from 2 to 4, particularly preferably from 2.5 to 3.5, in particular from 2.8 to 3.2, and their OH number is preferably from 300 to 900 mg KOH/g, and their content of se- condary OH groups is preferably at least 50%, with preference at least 60%, with particular preference at least 70% and in particular at least 80%.
  • the polyetherol used here preferably comprises polyetherol based on glycerol as starter and on propylene-1 ,2-oxide.
  • the polyurethane composition can further comprise additives.
  • Said additives can comprise any of the auxiliaries and additives known for producing polyurethanes. Examples that may be mentioned are surfactant, release agents, coupling agents, fillers, dyes, pigments, flame retar- dants, hydrolysis stabilizers, viscosity reducers, water scavengers, antifoaming agents, and also substances having fungistatic and bacteriostatic action. Substances of this type are known and are described by way of example in "Kunststoffhandbuch, Band 7, Polyurethane” [Plastics Handbook, volume 7, Polyurethanes] Carl Hanser Verlag, 3rd edition 1993, chapter 3.4.4 and 3.4.6 to 3.4.1 1 .
  • viscosity reducers examples include y-butyrolactone, propylene carbonate, and also reactive diluents, such as dipropylene glycol, diethylene glycol, and tripropylene glycol.
  • Coupling agents that can be used comprise silanes, such as isocyanate silanes, epoxysila- nes, or aminosilanes. Substances of this type are described by way of example in E. P. Plued- demann, Silane Coupling Agents, 2nd ed., Plenum Press, New York, 1991 and in K. L. Mittal, ed., Silanes and Other Coupling Agents, VSP, Utrecht, 1992.
  • silanes such as isocyanate silanes, epoxysila- nes, or aminosilanes. Substances of this type are described by way of example in E. P. Plued- demann, Silane Coupling Agents, 2nd ed., Plenum Press, New York, 1991 and in K. L. Mittal, ed., Silanes and Other Coupling Agents, VSP, Utrecht, 1992.
  • Release agents that can be used are any of the conventional release agents used in producing polyurethanes, examples being long-chain carboxylic acids, in particular fatty acids, such as stearic acid, amines of long-chain carboxylic acids, e.g. stearamide, fatty acid esters, metal salts of long-chain carboxylic acids, e.g. zinc stearate, or silicones.
  • Particularly suitable materials are the internal release agents obtainable specifically for the pultrusion process, e.g. from Axel Plastics or Technick Products.
  • the internal release agents from Technick Products probably comprise phosphoric acid and fatty acids.
  • the internal release agents from Axel Plastics probably comprise fatty acids.
  • the molar ratio of the isocyanate reactive compound to the isocyanate is in the range of 1 :0.5 to 1 :2.
  • Polyurethane composites are also provided, wherein the polyurethane composite comprises:
  • the reinforcing material is a fiber material.
  • the fiber material used can comprise any of the types of continuous-filament fibers.
  • Continuous-filament fiber here means a fiber material the length of which is at least a plurality of meters. These materials are by way of example unwound from rolls.
  • the fiber material used here can comprise individual fibers, known as fiber rovings, braided fibers, fiber mats, fiber scrims, and woven fibers. Particularly in the case of fiber composites, such as braided fibers, twisted fibers, fiber scrims, or woven fibers, there can also be shorter individual fibers comprised within the individual fibers comprised within said fiber structures.
  • the fiber material comprises or is composed of glass fiber, glass mats, carbon fiber, polyester fiber, natural fiber, aramid fiber, basalt fiber, or nylon fiber, and it is particularly preferable to use carbon fibers or glass fibers.
  • the weight ratio of the polyurethane composition to the reinforcing material is in the range of 10:90 to 70:30, preferably 15:85 to 50:50, more preferably 18:82 to 30:70.
  • the polyurethane composites are prepared by mixing components of the polyurethane composition to give a polyurethane reaction mixture, and then impregnating the reinforcing material with the resultant reaction mixture.
  • the present invention also provides an article produced from a polyurethane composite above by pultrusion.
  • the articles are bridge components, large artificial wood, large pole structure, complex window profile, reefer container. Examples
  • Component A and component B are mixed for 1 min using SpeedMixer available from FlackTek Inc. at 25°C. Then, gel time is measured by gel timer available from SHYODU IN- STRU ME NT COMPANY.
  • PU panel sample is prepared by mixing component A and component B for 1 min using SpeedMixer at 25°C, and vacuum pumping for 7 min at 70°C and placing for 8 min at 70°C, then curing for 1 h at 150°C.
  • Comparative example 2 are carried out by same procedure as comparative example 1 except that the amounts of 2,2'-MDI and 2,4'-MDI and their ratio vary.
  • Examples 1 -5 are carried out by same procedure as comparative example 1 according to the components and amounts listed in Table 1 .
  • Comparative example 1 The pure PU resin's mechanical properties of Comparative example 1 , Examples 1 -3 are listed in Table 2.
  • the preparation of PU panel sample can be referred to Comparative example 1 .
  • glass fiber reinforced PU composite is prepared using a mixture of glass fiber and sample from Example 1 by pultrusion process, wherein the content of glass fiber is 80wt% based on the weight of the PU composite.
  • the measured result is shown in Table 3.
  • Example 1 -3 shows that the gel times of Example 1 -3 are significantly greater than that of Comparative example 1 and Comparative example 2, even about 2 times or above of the gel time of Comparative example 1 and Comparative example 2, which indicates that appropriate amount of 2,2'-MDI based on the total amount of 2,2'-MDI and 2,4'-MDI used is important to prolong the processing time. Furthermore, the prolonging of the gel time does not compromise its curing speed.
  • Example 1 , Example 4 and Example 5 show that the gel times become longer with the ratio of 2,2'-MDI/2,4'-MDI increasing even if the total amount of 2,2'-MDI and 2,4'-MDI is about same.
  • PU composite samples are prepared via pultrusion process by impregnating glass fiber (Owens Corning PS4100) with sample of example 1.
  • the physical properties of the PU composites are excellent, as shown in Table 3, which are particularly suitable for producing large size composite parts, e.g. bridge components, large artificial wood, large pole structure, complex window profile, reefer container.

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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)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Inorganic Chemistry (AREA)
  • Manufacturing & Machinery (AREA)
  • Composite Materials (AREA)
  • Mechanical Engineering (AREA)
  • Polyurethanes Or Polyureas (AREA)
  • Reinforced Plastic Materials (AREA)

Abstract

L'invention concerne une composition de polyuréthane comprenant : (1) un isocyanate ; et (2) un composé réactif à l'isocyanate ; l'isocyanate comprenant du 2,2'-diphénylméthane diisocyanate et du 2,4'-diphénylméthane diisocyanate, et la quantité de 2,2'-diphénylméthane diisocyanate est dans la plage de 10 à 100 % en poids sur la base du poids total de 2,2'-diphénylméthane diisocyanate et 2,4''-diphénylméthane diisocyanate. L'invention concerne également un composite de polyuréthane comprenant ladite composition de polyuréthane et un matériau de renforcement, et un article produit à partir dudit composite de polyuréthane.
PCT/EP2018/074631 2017-09-29 2018-09-12 Composites de polyuréthane WO2019063294A1 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
KR1020207012741A KR20200062302A (ko) 2017-09-29 2018-09-12 폴리우레탄 복합재
CN201880061079.5A CN111183166B (zh) 2017-09-29 2018-09-12 聚氨酯复合材料
AU2018340584A AU2018340584A1 (en) 2017-09-29 2018-09-12 Polyurethane composites

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CN2017104336 2017-09-29
CNPCT/CN2017/104336 2017-09-29

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WO2019063294A1 true WO2019063294A1 (fr) 2019-04-04

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CN (1) CN111183166B (fr)
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CN112011027A (zh) * 2019-05-31 2020-12-01 万华化学（北京）有限公司 一种聚氨酯复合材料制备方法
EP4223826A1 (fr) * 2022-02-08 2023-08-09 Covestro Deutschland AG Composition d'isocyanate et son utilisation

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CN111718460A (zh) * 2020-08-07 2020-09-29 宁波耀众模塑科技有限公司 一种融合碳材质防散发的聚氨酯发泡阻燃剂配方

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