JP2015512979A - 相分離を有する2kポリウレタン系 - Google Patents
相分離を有する2kポリウレタン系 Download PDFInfo
- Publication number
- JP2015512979A JP2015512979A JP2014559166A JP2014559166A JP2015512979A JP 2015512979 A JP2015512979 A JP 2015512979A JP 2014559166 A JP2014559166 A JP 2014559166A JP 2014559166 A JP2014559166 A JP 2014559166A JP 2015512979 A JP2015512979 A JP 2015512979A
- Authority
- JP
- Japan
- Prior art keywords
- component polyurethane
- polyurethane composition
- composition
- composition according
- polyols
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 239000004814 polyurethane Substances 0.000 title claims abstract description 40
- 229920002635 polyurethane Polymers 0.000 title claims abstract description 40
- 238000005191 phase separation Methods 0.000 title description 6
- 239000000203 mixture Substances 0.000 claims abstract description 106
- 229920005862 polyol Polymers 0.000 claims abstract description 53
- 150000003077 polyols Chemical class 0.000 claims abstract description 49
- 239000000654 additive Substances 0.000 claims abstract description 10
- 239000005056 polyisocyanate Substances 0.000 claims abstract description 10
- 229920001228 polyisocyanate Polymers 0.000 claims abstract description 10
- 125000003118 aryl group Chemical group 0.000 claims abstract description 4
- 229920005903 polyol mixture Polymers 0.000 claims abstract description 4
- 239000000835 fiber Substances 0.000 claims description 37
- 239000003054 catalyst Substances 0.000 claims description 21
- 238000000034 method Methods 0.000 claims description 18
- 239000011159 matrix material Substances 0.000 claims description 17
- 238000006243 chemical reaction Methods 0.000 claims description 16
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- KORSJDCBLAPZEQ-UHFFFAOYSA-N dicyclohexylmethane-4,4'-diisocyanate Chemical compound C1CC(N=C=O)CCC1CC1CCC(N=C=O)CC1 KORSJDCBLAPZEQ-UHFFFAOYSA-N 0.000 description 2
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- 229920001610 polycaprolactone Polymers 0.000 description 1
- 239000004632 polycaprolactone Substances 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920005604 random copolymer Polymers 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 125000001302 tertiary amino group Chemical group 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 239000012974 tin catalyst Substances 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 238000001721 transfer moulding Methods 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
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- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
- 150000004072 triols Chemical class 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
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- 239000000080 wetting agent Substances 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
Classifications
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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
- C08G18/4829—Polyethers containing at least three hydroxy groups
-
- 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
- B29C45/00—Injection moulding, i.e. forcing the required volume of moulding material through a nozzle into a closed mould; Apparatus therefor
- B29C45/0001—Injection moulding, i.e. forcing the required volume of moulding material through a nozzle into a closed mould; Apparatus therefor characterised by the choice of material
-
- 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
- B29C45/00—Injection moulding, i.e. forcing the required volume of moulding material through a nozzle into a closed mould; Apparatus therefor
- B29C45/17—Component parts, details or accessories; Auxiliary operations
- B29C45/1701—Component parts, details or accessories; Auxiliary operations using a particular environment during moulding, e.g. moisture-free or dust-free
-
- 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
- B29C70/42—Shaping or impregnating by compression not applied for producing articles of definite length, i.e. discrete articles
- B29C70/46—Shaping or impregnating by compression not applied for producing articles of definite length, i.e. discrete articles using matched moulds, e.g. for deforming sheet moulding compounds [SMC] or prepregs
- B29C70/48—Shaping or impregnating by compression not applied for producing articles of definite length, i.e. discrete articles using matched moulds, e.g. for deforming sheet moulding compounds [SMC] or prepregs and impregnating the reinforcements in the closed mould, e.g. resin transfer moulding [RTM], e.g. by vacuum
-
- 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
- C08G18/18—Catalysts containing secondary or tertiary amines or salts thereof
- C08G18/20—Heterocyclic amines; Salts thereof
- C08G18/2009—Heterocyclic amines; Salts thereof containing one heterocyclic ring
- C08G18/2027—Heterocyclic amines; Salts thereof containing one heterocyclic ring having two nitrogen atoms in the ring
-
- 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
- C08G18/24—Catalysts containing metal compounds of tin
- C08G18/242—Catalysts containing metal compounds of tin organometallic compounds containing tin-carbon bonds
-
- 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
- C08G18/797—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing carbodiimide and/or uretone-imine groups
-
- 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
- C08J5/24—Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs
- C08J5/249—Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs characterised by the additives used in the prepolymer mixture
-
- 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
- C08K7/00—Use of ingredients characterised by shape
- C08K7/02—Fibres or whiskers
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
- B29K—INDEXING SCHEME ASSOCIATED WITH SUBCLASSES B29B, B29C OR B29D, RELATING TO MOULDING MATERIALS OR TO MATERIALS FOR MOULDS, REINFORCEMENTS, FILLERS OR PREFORMED PARTS, e.g. INSERTS
- B29K2075/00—Use of PU, i.e. polyureas or polyurethanes or derivatives thereof, as moulding material
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Manufacturing & Machinery (AREA)
- Mechanical Engineering (AREA)
- Composite Materials (AREA)
- Inorganic Chemistry (AREA)
- Polyurethanes Or Polyureas (AREA)
- Reinforced Plastic Materials (AREA)
Abstract
Description
成分A
ポリエーテルトリオール(アミン不含、Mn 約350)
成分B
MDI 異性体混合物
NCO:OH比 1.5:1
粘度: 開始時 190mPas
5分 270mPas
10分 480mPas
成分AおよびBを、0.2%DABCOと共に、1.15:1のNCO:OH比で混合した。
Claims (14)
- ・10〜80重量%の、200g/mol〜3000g/molの数平均分子量を有する少なくとも1種のポリオール、
・5〜70重量%の少なくとも1種の芳香族ポリイソシアネート、
・0〜15重量%の添加剤
を含有する二成分型ポリウレタン組成物であって、
ここで、該組成物は2:1〜1:2のNCO:OH比を有し、該組成物は20〜3000mPas(EN ISO 2555、ブルックフィールド粘度計、25℃)の粘度を有し、混合後に相不相溶性を示し、ポリオール混合物の官能性は2.3より大きい、二成分型ポリウレタン組成物。 - 前記混合物は、1000mPas(25℃)より低い粘度を有することを特徴とする、請求項1に記載の二成分型ポリウレタン組成物。
- MDIおよびその異性体に由来する少なくとも50mol%のイソシアネート基を含有することを特徴とする、請求項1または2に記載の二成分型ポリウレタン組成物。
- 2.5より大きい平均官能性を有するポリエステルポリオールおよび/または特にポリエーテルポリオールを、ポリオールとして使用することを特徴とする、請求項1〜3のいずれかに記載の二成分型ポリウレタン組成物。
- 錯生成剤としてのポリヒドロキシ化合物を有する、第3級アミンまたはSn化合物、特にSn触媒を、触媒として使用することを特徴とする、ここで、該錯生成剤は環状α-ヒドロキシケトンまたは1-アルキル-2,3,4-トリフェノールから選択される、請求項1〜4のいずれかに記載の二成分型ポリウレタン組成物。
- 架橋された組成物は60℃を超えるガラス転移温度Tgを有することを特徴とする、請求項1〜5のいずれかに記載の二成分型ポリウレタン組成物。
- イソシアネート基の量が、カルボジイミドおよびその誘導体、特にウレトンイミンへの反応により減少することを特徴とする、請求項1〜6のいずれかに記載の二成分型ポリウレタン組成物。
- 架橋された組成物は1000MPaより高いEモジュラスを有することを特徴とする、請求項1〜7のいずれかに記載の二成分型ポリウレタン組成物。
- 繊維材料を有する外部型を提供し、請求項1〜8のいずれかに記載の液状二成分型ポリウレタン組成物を該型中に圧力下で導入し、ここで、該組成物は相不相溶性の状態で導入される、繊維複合材料の製造方法。
- 成形品に基づいて60%(体積%)を超える繊維割合が使用されることを特徴とする、請求項9に記載の方法。
- 充填された型を120℃以下の温度で硬化させることを特徴とする、請求項9または10に記載の方法。
- 組成物を混合直後に脱気することを特徴とする、請求項9〜11のいずれかに記載の方法。
- 少なくとも60%の合成繊維材料、および、請求項1〜8のいずれかに記載の組成物から得られる、40%以下の架橋された二成分型ポリウレタン組成物を含有する、繊維複合材料。
- マトリックス結合剤は60℃を超えるTgを有することを特徴とする、請求項13または14に記載の繊維複合材料。
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EP12157299 | 2012-02-28 | ||
PCT/EP2013/053699 WO2013127732A1 (de) | 2012-02-28 | 2013-02-25 | 2k-polyurethansysteme mit phasentrennung |
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JP2015510011A (ja) * | 2012-02-28 | 2015-04-02 | ヘンケル・アクチェンゲゼルシャフト・ウント・コムパニー・コマンディットゲゼルシャフト・アウフ・アクチェンHenkel AG & Co.KGaA | 高いガラス転移温度を有する2kポリウレタン系 |
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DE102011002809A1 (de) * | 2011-01-18 | 2012-07-19 | Henkel Ag & Co. Kgaa | 2K-PU-Zusammensetzung mit verzögerter Vernetzung |
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ES2620980T3 (es) | 2014-09-30 | 2017-06-30 | Henkel Ag & Co. Kgaa | Composiciones que comprenden un material de fibra y un aglutinante termoplástico |
CA3047871A1 (en) * | 2016-12-28 | 2018-07-05 | Henkel Ag & Co. Kgaa | Two-component polyurethane adhesive |
EP3533530A1 (en) | 2018-03-01 | 2019-09-04 | Henkel AG & Co. KGaA | Process for the production of composite materials at low temperatures |
WO2020102871A1 (pt) * | 2018-11-22 | 2020-05-28 | Formtap Interni Sistemas Automotivos S/A | Aperfeiçoamento introduzido em processo de obtenção de compósitos termo estruturais |
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KR20140129304A (ko) | 2014-11-06 |
EP2820061A1 (de) | 2015-01-07 |
US20140371391A1 (en) | 2014-12-18 |
CN104136476A (zh) | 2014-11-05 |
AU2013225178A1 (en) | 2014-09-18 |
JP6534260B2 (ja) | 2019-06-26 |
CA2863141C (en) | 2021-08-17 |
WO2013127732A1 (de) | 2013-09-06 |
CN104136476B (zh) | 2017-04-19 |
JP2019035088A (ja) | 2019-03-07 |
MX2014010290A (es) | 2014-10-13 |
EP2820061B1 (de) | 2021-07-21 |
KR20140127830A (ko) | 2014-11-04 |
CN104136477A (zh) | 2014-11-05 |
MX365691B (es) | 2019-06-11 |
WO2013127734A1 (de) | 2013-09-06 |
CN104136477B (zh) | 2016-06-29 |
AU2013225176A1 (en) | 2014-09-18 |
EP2820060A1 (de) | 2015-01-07 |
AU2013225178B2 (en) | 2016-01-07 |
MX365277B (es) | 2019-05-29 |
AU2013225176B2 (en) | 2016-01-28 |
CA2863145C (en) | 2021-03-16 |
KR102046197B1 (ko) | 2019-11-18 |
CA2863141A1 (en) | 2013-09-06 |
US20160362516A1 (en) | 2016-12-15 |
ES2885763T3 (es) | 2021-12-15 |
JP2015510011A (ja) | 2015-04-02 |
MX2014010292A (es) | 2014-10-13 |
CA2863145A1 (en) | 2013-09-06 |
US10131738B2 (en) | 2018-11-20 |
US10093766B2 (en) | 2018-10-09 |
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