JP2020500990A - 熱可塑性ポリウレタンマトリックス樹脂 - Google Patents
熱可塑性ポリウレタンマトリックス樹脂 Download PDFInfo
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- JP2020500990A JP2020500990A JP2019530498A JP2019530498A JP2020500990A JP 2020500990 A JP2020500990 A JP 2020500990A JP 2019530498 A JP2019530498 A JP 2019530498A JP 2019530498 A JP2019530498 A JP 2019530498A JP 2020500990 A JP2020500990 A JP 2020500990A
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- 0 Oc1ccc(*c(cc2)ccc2O)cc1 Chemical compound Oc1ccc(*c(cc2)ccc2O)cc1 0.000 description 1
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- 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
- C08G18/30—Low-molecular-weight compounds
- C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
- C08G18/3203—Polyhydroxy compounds
- C08G18/3206—Polyhydroxy compounds aliphatic
- C08G18/3209—Aliphatic aldehyde condensates and hydrogenation products thereof
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- 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
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/30—Low-molecular-weight compounds
- C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
- C08G18/3203—Polyhydroxy compounds
- C08G18/3206—Polyhydroxy compounds aliphatic
-
- 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
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- 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
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- 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
- C08G18/30—Low-molecular-weight compounds
- C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
- C08G18/3203—Polyhydroxy compounds
- C08G18/3215—Polyhydroxy compounds containing aromatic groups or benzoquinone groups
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- 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
-
- 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
- C08G18/487—Polyethers containing cyclic groups
- C08G18/4879—Polyethers containing cyclic groups containing aromatic 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
- C08G18/65—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen
- C08G18/6505—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen the low-molecular compounds being compounds of group C08G18/32 or polyamines of C08G18/38
- C08G18/6511—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen the low-molecular compounds being compounds of group C08G18/32 or polyamines of C08G18/38 compounds of group C08G18/3203
-
- 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
- C08G18/65—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen
- C08G18/66—Compounds of groups C08G18/42, C08G18/48, or C08G18/52
- C08G18/6603—Compounds of groups C08G18/42, C08G18/48, or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38
-
- 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
-
- 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
- B29C70/06—Fibrous reinforcements only
-
- 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
- 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
- C08K3/34—Silicon-containing compounds
- C08K3/346—Clay
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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)
- Mechanical Engineering (AREA)
- Composite Materials (AREA)
- Manufacturing & Machinery (AREA)
- Polyurethanes Or Polyureas (AREA)
- Reinforced Plastic Materials (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Abstract
Description
(i)式(I)
nは0、1、2または3、好ましくは0であり;
ここで、n=0、2または3の場合、R1、R1’、R2およびR2’のうちの少なくとも1つは置換または非置換のC1−4アルキルである]
の少なくとも1つのC3−8アルカンジオール;
(ii)少なくとも1つのポリイソシアネート;および
(iii)少なくとも1つのアルコキシル化芳香族ジオール
を含む、熱可塑性ポリウレタンマトリックス樹脂組成物に関する。
1)繊維材料を含む外型を供給する工程;
2)本発明による熱可塑性ポリウレタンマトリックス樹脂組成物を、好ましくは加圧下で、前記型に導入する工程;および
3)140℃まで、好ましくは60〜120℃の温度で前記組成物を硬化させる工程;
を含む、本発明による繊維強化複合材料の製造方法に関する。
(i)式(I)
nは0、1、2または3、好ましくは0であり;
ここで、n=0、2または3の場合、R1、R1’、R2およびR2’のうちの少なくとも1つは置換または非置換のC1−4アルキルである]
の少なくとも1つのC3−8アルカンジオール、;
(ii)少なくとも1つのポリイソシアネート;および
(iii)少なくとも1つのアルコキシル化芳香族ジオール
を含む。
のものである。
1)繊維材料を含む外型を供給する工程;
2)ポリウレタンマトリックス樹脂組成物を前記型に、好ましくは加圧下で導入する工程;および
3)140℃まで、好ましくは60〜120℃の温度で前記組成物を硬化させる工程
を含む、繊維強化複合材料の製造方法も提供する。
Claims (10)
- (a)n=0;および/または
(b)R1’またはR2’または両方はHであり;および/または
(c)R1および/またはR2はメチルおよびエチルから選択され、好ましくはメチルである
請求項1に記載の組成物。 - 式(I)の前記ジオールは、2,3−ブタンジオール、2,3−ペンタンジオール、2,3−ヘキサンジオール、3,4−ヘキサンジオール、1,2−プロパンジオール、1,3−プロパンジオール、1,2−ブタンジオール、1,2−ペンタンジオール、1,2−ヘキサンジオール、好ましくは2,3−ブタンジオールおよび1,2−プロパンジオールからなる群から選択され、より好ましくは2,3−ブタンジオールである、請求項1または2に記載の組成物。
- 成分(i)および(iii)を合わせたOH基と前記ポリイソシアネート(ii)のNCO基とのモル比は、2:1〜1:10、好ましくは2:1〜1:5、最も好ましくは2:1〜1:2である、請求項1〜3のいずれかに記載の組成物。
- 少なくとも1つのポリイソシアネートは、芳香族ポリイソシアネートから、好ましくは4,4'−ジフェニルメタンジイソシアネート、2,4'−ジフェニルメタンジイソシアネート、ポリメリック4,4'−ジフェニルメタンジイソシアネート、ポリメリック2,4'−ジフェニルメタンジイソシアネート、および前記の混合物からなる群から選択される、請求項1〜4のいずれかに記載の組成物。
- 前記熱可塑性ポリウレタンマトリックス樹脂組成物は少なくとも1つの触媒をさらに含む、請求項1〜6のいずれかに記載の組成物。
- 請求項1〜7のいずれかに記載の硬化熱可塑性ポリウレタンマトリックス樹脂組成物と繊維材料とを含む繊維強化複合材料であって、繊維材料が前記繊維強化複合材料の全体積に基づいて、30体積%超の割合で含まれることを特徴とする、繊維強化複合材料。
- 1)前記繊維材料を含む外型を供給する工程;
2)請求項1〜7のいずれかに記載の熱可塑性ポリウレタンマトリックス樹脂組成物を、好ましくは加圧下で、前記型に導入する工程;および
3)140℃まで、好ましくは60〜120℃の温度で前記組成物を硬化させる工程
を含む、請求項8に記載の繊維強化複合材料の製造方法。 - 鉄道車両、自動車車両、航空機、船、宇宙船、モーターバイク、自転車、スポーツ用品、運動器具、携帯電話およびラップトップの筐体、ヘルメット、機能性衣類、靴、橋および建物における建設部材、または風力タービン翼における、請求項1〜7のいずれかに記載の組成物、または請求項8に記載の繊維強化複合材料の使用。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP16202563.9A EP3333209B1 (en) | 2016-12-07 | 2016-12-07 | Thermoplastic polyurethane matrix resin |
EP16202563.9 | 2016-12-07 | ||
PCT/EP2017/080998 WO2018104145A1 (en) | 2016-12-07 | 2017-11-30 | Thermoplastic polyurethane matrix resin |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2020500990A true JP2020500990A (ja) | 2020-01-16 |
JP7177056B2 JP7177056B2 (ja) | 2022-11-22 |
Family
ID=57681231
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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JP2019530498A Active JP7177056B2 (ja) | 2016-12-07 | 2017-11-30 | 熱可塑性ポリウレタンマトリックス樹脂 |
Country Status (7)
Country | Link |
---|---|
US (1) | US11312810B2 (ja) |
EP (1) | EP3333209B1 (ja) |
JP (1) | JP7177056B2 (ja) |
CN (1) | CN110072903B (ja) |
CA (1) | CA3045711A1 (ja) |
MX (1) | MX2019006473A (ja) |
WO (1) | WO2018104145A1 (ja) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
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JP6804487B2 (ja) * | 2018-05-09 | 2020-12-23 | 第一工業製薬株式会社 | 熱可塑性ポリウレタン樹脂製造用2液硬化型組成物、熱可塑性ポリウレタン樹脂および繊維強化樹脂 |
US11865797B2 (en) * | 2018-09-12 | 2024-01-09 | Bauer Hockey, Llc | Method of forming a sporting implement |
Citations (4)
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WO2015144765A1 (de) * | 2014-03-25 | 2015-10-01 | Basf Se | Tpu pneumatikschlauch |
US20160090515A1 (en) * | 2013-05-15 | 2016-03-31 | Sika Technology Ag | Two component polyurethane composition |
JP2016526064A (ja) * | 2013-05-15 | 2016-09-01 | シーカ・テクノロジー・アーゲー | 2剤型ポリウレタン組成物 |
WO2016208284A1 (ja) * | 2015-06-26 | 2016-12-29 | Dic株式会社 | 鋼板表面処理剤、及びその塗膜を有する鋼板 |
Family Cites Families (6)
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JPS5385896A (en) * | 1976-12-30 | 1978-07-28 | Teijin Ltd | Thermoplastic polyurethane resin having improved property and its preparation |
US4387214A (en) | 1981-06-29 | 1983-06-07 | Eastman Kodak Company | Thermosetting powder coating compositions |
US20070129524A1 (en) | 2005-12-06 | 2007-06-07 | Sunkara Hari B | Thermoplastic polyurethanes comprising polytrimethylene ether soft segments |
ES2433107T3 (es) | 2010-12-13 | 2013-12-09 | Lanxess Deutschland Gmbh | Procedimiento para la optimización del comportamiento de cristalización de masas moldeables de poliéster |
EP2818489A1 (de) * | 2013-06-28 | 2014-12-31 | Basf Se | Hydrolysebeständige Polyurethanformkörper |
ES2620980T3 (es) | 2014-09-30 | 2017-06-30 | Henkel Ag & Co. Kgaa | Composiciones que comprenden un material de fibra y un aglutinante termoplástico |
-
2016
- 2016-12-07 EP EP16202563.9A patent/EP3333209B1/en active Active
-
2017
- 2017-11-30 WO PCT/EP2017/080998 patent/WO2018104145A1/en active Application Filing
- 2017-11-30 JP JP2019530498A patent/JP7177056B2/ja active Active
- 2017-11-30 MX MX2019006473A patent/MX2019006473A/es unknown
- 2017-11-30 CN CN201780075320.5A patent/CN110072903B/zh active Active
- 2017-11-30 CA CA3045711A patent/CA3045711A1/en active Pending
-
2019
- 2019-06-03 US US16/429,546 patent/US11312810B2/en active Active
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20160090515A1 (en) * | 2013-05-15 | 2016-03-31 | Sika Technology Ag | Two component polyurethane composition |
JP2016526064A (ja) * | 2013-05-15 | 2016-09-01 | シーカ・テクノロジー・アーゲー | 2剤型ポリウレタン組成物 |
WO2015144765A1 (de) * | 2014-03-25 | 2015-10-01 | Basf Se | Tpu pneumatikschlauch |
WO2016208284A1 (ja) * | 2015-06-26 | 2016-12-29 | Dic株式会社 | 鋼板表面処理剤、及びその塗膜を有する鋼板 |
Also Published As
Publication number | Publication date |
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MX2019006473A (es) | 2019-08-21 |
CN110072903A (zh) | 2019-07-30 |
WO2018104145A1 (en) | 2018-06-14 |
JP7177056B2 (ja) | 2022-11-22 |
US11312810B2 (en) | 2022-04-26 |
CN110072903B (zh) | 2022-07-26 |
US20190284329A1 (en) | 2019-09-19 |
EP3333209A1 (en) | 2018-06-13 |
CA3045711A1 (en) | 2018-06-14 |
EP3333209B1 (en) | 2023-09-20 |
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