WO2000075213A1 - Procede de fabrication d'un polyurethanne thermodurcissable a partir d'un polyurethanne thermoplastique et polyurethanne thermodurci susceptible d'etre obtenu par ledit procede - Google Patents
Procede de fabrication d'un polyurethanne thermodurcissable a partir d'un polyurethanne thermoplastique et polyurethanne thermodurci susceptible d'etre obtenu par ledit procede Download PDFInfo
- Publication number
- WO2000075213A1 WO2000075213A1 PCT/FR2000/001534 FR0001534W WO0075213A1 WO 2000075213 A1 WO2000075213 A1 WO 2000075213A1 FR 0001534 W FR0001534 W FR 0001534W WO 0075213 A1 WO0075213 A1 WO 0075213A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- thermoplastic polyurethane
- tpu
- polyurethane
- mixture
- transformation
- Prior art date
Links
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
- C08G18/83—Chemically modified polymers
-
- 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
- C08G18/2805—Compounds having only one group containing active hydrogen
- C08G18/288—Compounds containing at least one heteroatom other than oxygen or nitrogen
- C08G18/289—Compounds containing at least one heteroatom other than oxygen or nitrogen containing silicon
-
- 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
- C08G18/0895—Manufacture of polymers by continuous processes
-
- 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
- C08G18/798—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing urethdione 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
- C08G18/83—Chemically modified polymers
- C08G18/837—Chemically modified polymers by silicon containing compounds
Definitions
- the invention relates to a process for manufacturing a thermosetting polyurethane after transformation, from a thermoplastic polyurethane. It also relates to the thermoset polyurethane after transformation, capable of being obtained by said process.
- thermoplastic materials are used for the production of certain products, such as tubes for transporting hot fluids, electric cables, solid wheels, seals, silent blocks, shoe soles, etc.
- Thermoplastics are used in these different applications, in particular for their ease of implementation and their quality at room temperature, flexibility and mechanical resistance.
- these materials have the disadvantage of being not very resistant to heat, so that the
- thermosetting materials if they are effectively heat resistant, remain difficult to shape, so that their use is limited.
- the objective has therefore been to develop materials exhibiting the physical characteristics and the ease of transformation of thermoplastic materials endowed with the thermomechanical characteristics of thermosetting materials, and in particular their resistance to temperature.
- thermosetting polymer by modifying easily transformable thermoplastic polymers to allow them to crosslink after transformation into a finished product.
- a first method consists in mixing and extruding a polymer, and in particular a polyethylene with a peroxide.
- a polymer and in particular a polyethylene with a peroxide.
- such a method has the disadvantage not only of being feasible from a limited number of polyethylene, but also requires very expensive industrial installations.
- Another method consists in irradiating a polymer at 80 to 200 K gray exposure doses.
- this type of treatment is very expensive, that it tends to destroy rather than to improve the polymers used.
- Another process consists in grafting a hydrolysable organo-silane comprising at least one unsaturated chain of the vinyl type in the presence of an initiator of grafting of the vinyl functions, and in particular the peroxide, and of a polycondensation catalyst of the silane functions.
- the hydrolysis and polycondensation of the silane functions allow the crosslinking of the polymer to obtain the thermoset form.
- Polyethylenes are preferred, polymers of the thermoplastic polyurethane (TPU) type, which have very satisfactory mechanical characteristics depending on the applications envisaged. However, all known common TPUs lose their mechanical characteristics at a temperature of around 70 ° C. Thermosetting polyurethanes can also be used, which however remain very difficult to work.
- TPU thermoplastic polyurethane
- the problem posed is therefore to develop a process for manufacturing polyurethane retaining the processing conditions for thermoplastic polyurethanes (TPU) while retaining the main mechanical characteristics and adding improved thermal resistance superior to the thermal resistance of crosslinked polyethylenes.
- TPU thermoplastic polyurethanes
- the reaction with the amine causes the main macromolecular chains to break.
- the silanes are grafted at each of the ends of the different fragments according to the following reaction scheme:
- the invention provides a method of manufacturing a thermosetting polyurethane after transformation, from a thermoplastic polyurethane according to which grafting, using a bonding agent, onto macromolecules of thermoplastic polyurethane, a hydrolysable organo-silane of general formula:
- R 3 alkyl ahphatic, alkyl aromatic; n>1; R 4 being an organic radical capable of reacting with said binding agent, which comprises at least two isocyanate functions, the polyurethane thermoplastic obtained being able, after transformation, to self-crosslink in contact with water molecules so as to become thermosetting.
- R 4 is chosen from the group comprising the radicals NH 2 , NH, SH, OH, phenol, epoxy.
- R 4 is understood for any organic radical capable of reacting with an isocyanate function.
- the process of the invention has another advantage which is that of being able to adapt to all types of TPU, including esters, ethers, carbonates and caprolactones.
- the TPU chosen can be either aliphatic or aromatic.
- the organosilane is aminopropyltrimethoxysilane, of formula:
- This succession of reactions makes it possible to fix the hydrolyzable silane groups on the TPU chain without degrading it.
- the fact of grafting several silanes onto the same TPU chain can also promote subsequent crosslinking.
- thermoplastic polyurethane obtained self-crosslinks with moisture by hydrolysis and polycondensation of the silane functions grafted on the various macro-molecular chains of TPU (conventional reaction of hydrolysis and condensation of silanes).
- diisocyanate it is advantageous to use an aromatic, cycloaliphatic, ahphatic diisocyanate or their dimers.
- TDI 1-3 diisocyanatomethylbenzene
- 2,4'-MDI (1 isocyanato-2 (4-isocyanatophenyl) methylbenzene
- 4.4 'MDI 1, 1 - methylene bis (4-isocyanatobenzene)
- 2,4-TDI 2,4 di-isocyanato-1-methylbenzene
- PPDI 1, 4-diisocyanatobenzene
- H, 2 is advantageously chosen
- MDI (1,1-methylene bis (4-isocyanatocyclohexane)).
- diisocyanates above which can be used in the process of the invention is not exhaustive.
- HDI (1,6-diisocyanatohexane), CHDI (trans-1,4-diisocyanatocyclohexane), IPDI (5-isocyanato-l- (isocyanatomethyl) -1,3,3-trimethylcyclohexane) can also be used.
- TMDI (1,6-diisocyanato-2,2,4 (or 2,4,4) -trimethylhexane)
- m-TMXDI (1,3-bis (1-isocyanato-1-methylethylbenzene)
- p-TMXDI (1- isocyanato-1-methylethylbenzene)
- NDI 1,5-diisocyanatonaphthalene
- polymeric MDI isocyanic acid, polymethylene polyphenylene ester
- Desmodur R l,, l "-méthyllidynetris (4-isocyanatobenzene)
- Desmodur RI 4-isocyanatophenol phosphorothioate (3: 1) ester
- the concentration of binding agent necessary for the manufacture of TPU is between 0.1 and 30% by weight of TPU, advantageously between 3 and 4% by weight.
- the amount of binding agent is insufficient to avoid cutting the main chains of TPU. This results in a loss of the thermomechanical properties of the crosslinked polymer.
- the concentration of organosilane necessary to obtain a thermosetting polyurethane after transformation is between 0.05 and 15% by weight of TPU, advantageously 2%.
- the density of the mesh is not sufficient to obtain an insoluble product.
- thermoplastic polyurethane and binder A mixture of thermoplastic polyurethane and binder is reacted at a temperature between 120 and 220 ° C so as to obtain a reactive TPU; - The reactive TPU mixture is then brought into contact with an organo-silane;
- thermoplastic polyurethane obtained can then be either granulated or transformed so as to obtain profiles of determined shape.
- This type of reaction can be carried out in one or two stages, in different reactors of the extruder, calendering, mixing tank, etc. type.
- the extruder When the process of the invention is carried out by extrusion, a single or twin-screw machine is used as the extruder, the profile of which is easily adaptable to each transformed TPU.
- the extruder has at least two mixing zones and at least three temperature zones.
- the maximum temperature imposed during the extrusion process is between 120 and 220 ° C depending on the nature of the TPU.
- the latter is introduced with the molecule comprising at least one isocyanate function, then the hydrolyzable organosilane is introduced into a zone located between 0 and 0.5 times the total length of the screw.
- the mixture to be extruded is granulated at the extruder outlet or directly transformed so as to obtain profiles of determined shape.
- the process has the advantage of providing semi-finished products which can again be used in another processing process, such as extrusion, calendering, injection, etc.
- thermosetting TPU after transformation can also be obtained by calendering or passing through an internal mixer of the Brabender type or any other processing machine which shears the material between 120 and 220 ° C.
- thermoplastic polyurethane and bonding agent at a temperature between 20 and 60 ° C, advantageously! 40 ° C;
- thermoplastic polyurethane and organosilane at a temperature between 20 and 60 ° C;
- thermoplastic polyurethane obtained is then either granulated or directly transformed.
- thermosetting polyurethane after transformation capable of being obtained by the process described above.
- FIG. 1 is a chromatographic analysis of TPU grafted according to Example 1.
- FIG. 2 represents the evolution of the Vicat point after crosslinking as a function of the percentage of binding agent and of the organosilane.
- a TPU twin-screw extruder marketed by GOODRICH under the brand ESTANE 58201 and 4 pcr of diTDI is introduced at the bottom of the hopper.
- the product obtained is stored in ambient air for a fortnight.
- the material is introduced into a TPU solvent and it is found that more than 85% of the material is insoluble, which proves that the crosslinking has indeed taken place and therefore that the grafting has been effective.
- FIG. 1 shows that there is no noticeable difference in molar masses between the base TPU and the grafted TPU, which proves that the TPU chains are not degraded .
- TPU sold by GOODRICH under the brand ESTANE 58201 is introduced into a kneader at 170 ° C. After 2.5 seconds, 2.5 pcr of ⁇ -APS (ethoxysilane) is introduced and after 30 seconds, 4 pcr of TDI are introduced. The melt is cooled.
- ⁇ -APS ethoxysilane
- Example 3 Compared to Example 3, in place of the mixer, a calandrette brought to 120 ° C. is used.
- the TPU sold by GOODRICH under the brand ESTANE 5715 is melted, then 4 pcr of diTDI is introduced after 20 seconds, then 30 seconds later, 2.2 pcr of M-APS (methoxysilane). The melt is cooled.
- Examples 2, 3 and 4 after a few days of exposure to humidity, it is verified that more than 80% of the mass of the materials was each time insoluble and that the initial Vicat point of each material was increased by 40 ° C.
- This process allows the mechanical characteristics of the base polymer to be preserved at temperatures above 40 ° C.
Abstract
Description
Claims
Priority Applications (8)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP00938883A EP1183296B1 (fr) | 1999-06-08 | 2000-06-05 | Procede de fabrication d'un polyurethanne thermodurcissable a partir d'un polyurethanne thermoplastique et polyurethanne thermodurci susceptible d'etre obtenu par ledit procede |
AT00938883T ATE265483T1 (de) | 1999-06-08 | 2000-06-05 | Verfahren zur herstellung eines hitzehärtbaren polyurethans ausgehend von einem thermoplastischen polyurethan und hitzegehärtetes polyurethan, das mittels diesem verfahren hergestellt werden kann |
JP2001502491A JP2003501531A (ja) | 1999-06-08 | 2000-06-05 | 熱硬化性ポリウレタンを熱可塑性ポリウレタンから製造する方法および当該方法を用いて得られる熱硬化性ポリウレタン |
KR1020017015679A KR20020016823A (ko) | 1999-06-08 | 2000-06-05 | 열가소성 폴리우레탄으로부터 열경화성 폴리우레탄제조방법 및 상기 방법을 이용하여 얻을 수 있는 열경화성폴리우레탄 |
CA002375721A CA2375721A1 (fr) | 1999-06-08 | 2000-06-05 | Procede de fabrication d'un polyurethanne thermodurcissable a partir d'un polyurethanne thermoplastique et polyurethanne thermodurci susceptible d'etre obtenu par ledit procede |
DE60010255T DE60010255D1 (de) | 1999-06-08 | 2000-06-05 | Verfahren zur herstellung eines hitzehärtbaren polyurethans ausgehend von einem thermoplastischen polyurethan und hitzegehärtetes polyurethan, das mittels diesem verfahren hergestellt werden kann |
AU54116/00A AU5411600A (en) | 1999-06-08 | 2000-06-05 | Method for producing thermosetting polyurethane from thermoplastic polyurethane and thermoset polyurethane obtained using said method |
US10/013,962 US6861491B2 (en) | 1999-06-08 | 2001-12-10 | Method for producing a thermosetting polyurethane from a thermoplastic polyurethane and thermoset polyurethane obtainable using said method |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR99/07454 | 1999-06-08 | ||
FR9907454A FR2794759B1 (fr) | 1999-06-08 | 1999-06-08 | Procede de fabrication d'un polyurethanne thermodurcissable apres transformation a partir d'un polyurethanne thermoplastique, et polyurethanne thermodurci apres transformation susceptible d'etre obtenu par ledit procede |
Related Child Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US10/013,962 Continuation US6861491B2 (en) | 1999-06-08 | 2001-12-10 | Method for producing a thermosetting polyurethane from a thermoplastic polyurethane and thermoset polyurethane obtainable using said method |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2000075213A1 true WO2000075213A1 (fr) | 2000-12-14 |
Family
ID=9546710
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/FR2000/001534 WO2000075213A1 (fr) | 1999-06-08 | 2000-06-05 | Procede de fabrication d'un polyurethanne thermodurcissable a partir d'un polyurethanne thermoplastique et polyurethanne thermodurci susceptible d'etre obtenu par ledit procede |
Country Status (12)
Country | Link |
---|---|
US (1) | US6861491B2 (fr) |
EP (1) | EP1183296B1 (fr) |
JP (1) | JP2003501531A (fr) |
KR (1) | KR20020016823A (fr) |
CN (1) | CN1153795C (fr) |
AT (1) | ATE265483T1 (fr) |
AU (1) | AU5411600A (fr) |
CA (1) | CA2375721A1 (fr) |
DE (1) | DE60010255D1 (fr) |
ES (1) | ES2219348T3 (fr) |
FR (1) | FR2794759B1 (fr) |
WO (1) | WO2000075213A1 (fr) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2010110661A2 (fr) | 2009-03-24 | 2010-09-30 | De Veenvoort B.V. | Matériau de couverture étanche à l'eau et résistant aux intempéries |
WO2020136106A1 (fr) | 2018-12-24 | 2020-07-02 | Basf Se | Adhésif thermofusible de polyuréthane thermoplastique et son utilisation |
Families Citing this family (17)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE10334265A1 (de) * | 2003-07-25 | 2005-02-24 | Basf Ag | Thermoplastisches Polyurethan enthaltend Silangruppen |
DE10334266A1 (de) * | 2003-07-25 | 2005-02-24 | Basf Ag | Thermoplastisches Polyurethan enthaltend Silangruppen |
DE10334264A1 (de) * | 2003-07-25 | 2005-02-24 | Basf Ag | Thermoplastisches Polyurethan enthaltend Silangruppen |
DE102004041141A1 (de) * | 2004-08-24 | 2006-03-02 | Basf Ag | Thermoplastisches Polyurethan enthaltend Silangruppen |
US7417094B2 (en) * | 2004-11-18 | 2008-08-26 | Pripro Polymer, Inc. | Cross-linked thermoplastic polyurethane/polyurea and method of making same |
DE102004060799A1 (de) * | 2004-12-17 | 2006-06-29 | Bayer Materialscience Ag | Thermoplastische Polyurethane und deren Verwendung |
ATE430771T1 (de) * | 2005-03-24 | 2009-05-15 | Medtronic Inc | Modifizierung von thermoplastischen polymeren |
DE102005028056A1 (de) * | 2005-06-16 | 2006-12-21 | Basf Ag | Thermoplastisches Polyurethan enthaltend Isocyanat |
FR2890226B1 (fr) * | 2005-08-26 | 2007-09-28 | Nexans Sa | Cable d'energie et/ou de telecommunication avec gaine en polyurethane thermoplastique reticule |
DE102005041954A1 (de) * | 2005-09-03 | 2007-03-08 | Bayer Materialscience Ag | Alkoxysilan- und spezielle Allophanat-und/oder Biuretgruppen aufweisende Prepolymere, ein Verfahren zu ihrer Herstellung sowie ihre Verwendung |
US7354971B2 (en) * | 2006-01-14 | 2008-04-08 | Bayer Materialscience Ag | Aqueous dispersions |
PL2032621T3 (pl) * | 2006-06-14 | 2020-02-28 | Huntsman International Llc | Sieciowalne termoplastyczne poliuretany |
US8501390B2 (en) | 2006-06-27 | 2013-08-06 | Xiper Innovations, Inc. | Laser engravable flexographic printing articles based on millable polyurethanes, and method |
US20080300069A1 (en) * | 2007-05-30 | 2008-12-04 | Murali Rajagopalan | Golf ball with a thermoset polyurethane cover |
CN106632942B (zh) * | 2016-09-30 | 2019-04-16 | 中国林业科学研究院林产化学工业研究所 | 一种具有自修复功能的热固性聚氨酯及其制备方法 |
CN111574822B (zh) * | 2020-06-04 | 2022-03-01 | 北京浦江兄弟科技有限公司 | 一种聚氨酯疏水薄膜、制备方法及其用途 |
CN116606541A (zh) * | 2023-05-15 | 2023-08-18 | 美瑞新材料股份有限公司 | 一种高强度耐脏污tpu材料及其制备方法 |
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EP0371370A1 (fr) * | 1988-11-29 | 1990-06-06 | Henkel Kommanditgesellschaft auf Aktien | Procédé de préparation et d'utilisation de masses adhésives thermofusibles durcissables par l'humidité |
JPH0397750A (ja) * | 1989-09-11 | 1991-04-23 | Showa Electric Wire & Cable Co Ltd | 熱可塑性エラストマ |
EP0478176A1 (fr) * | 1990-09-24 | 1992-04-01 | Lord Corporation | Adhésif pour le verre |
DE4115508A1 (de) * | 1991-05-11 | 1992-11-12 | Inst Technologie Der Polymere | Verfahren zur herstellung von hochmolekularen thermoplastisch verarbeitbaren polyurethanelastomeren mit verbesserter hydrolysebestaendigkeit und verbesserter verschleissfestigkeit |
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DE1745526B2 (de) * | 1967-03-16 | 1980-04-10 | Union Carbide Corp., New York, N.Y. (V.St.A.) | Verfahren zur Herstellung vulkanisierbarer, unter wasserfreien Bedingungen beständiger Polymerisate |
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DE3220866A1 (de) * | 1982-06-03 | 1983-12-08 | Dynamit Nobel Ag, 5210 Troisdorf | Vernetzbare harzmischungen |
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-
1999
- 1999-06-08 FR FR9907454A patent/FR2794759B1/fr not_active Expired - Fee Related
-
2000
- 2000-06-05 DE DE60010255T patent/DE60010255D1/de not_active Expired - Lifetime
- 2000-06-05 CA CA002375721A patent/CA2375721A1/fr not_active Abandoned
- 2000-06-05 JP JP2001502491A patent/JP2003501531A/ja active Pending
- 2000-06-05 KR KR1020017015679A patent/KR20020016823A/ko not_active Application Discontinuation
- 2000-06-05 AT AT00938883T patent/ATE265483T1/de not_active IP Right Cessation
- 2000-06-05 WO PCT/FR2000/001534 patent/WO2000075213A1/fr not_active Application Discontinuation
- 2000-06-05 EP EP00938883A patent/EP1183296B1/fr not_active Expired - Lifetime
- 2000-06-05 CN CNB008085927A patent/CN1153795C/zh not_active Expired - Fee Related
- 2000-06-05 ES ES00938883T patent/ES2219348T3/es not_active Expired - Lifetime
- 2000-06-05 AU AU54116/00A patent/AU5411600A/en not_active Abandoned
-
2001
- 2001-12-10 US US10/013,962 patent/US6861491B2/en not_active Expired - Fee Related
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
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EP0371370A1 (fr) * | 1988-11-29 | 1990-06-06 | Henkel Kommanditgesellschaft auf Aktien | Procédé de préparation et d'utilisation de masses adhésives thermofusibles durcissables par l'humidité |
JPH0397750A (ja) * | 1989-09-11 | 1991-04-23 | Showa Electric Wire & Cable Co Ltd | 熱可塑性エラストマ |
EP0478176A1 (fr) * | 1990-09-24 | 1992-04-01 | Lord Corporation | Adhésif pour le verre |
DE4115508A1 (de) * | 1991-05-11 | 1992-11-12 | Inst Technologie Der Polymere | Verfahren zur herstellung von hochmolekularen thermoplastisch verarbeitbaren polyurethanelastomeren mit verbesserter hydrolysebestaendigkeit und verbesserter verschleissfestigkeit |
Non-Patent Citations (1)
Title |
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PATENT ABSTRACTS OF JAPAN vol. 015, no. 282 (C - 0850) 17 July 1991 (1991-07-17) * |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2010110661A2 (fr) | 2009-03-24 | 2010-09-30 | De Veenvoort B.V. | Matériau de couverture étanche à l'eau et résistant aux intempéries |
WO2020136106A1 (fr) | 2018-12-24 | 2020-07-02 | Basf Se | Adhésif thermofusible de polyuréthane thermoplastique et son utilisation |
Also Published As
Publication number | Publication date |
---|---|
EP1183296A1 (fr) | 2002-03-06 |
JP2003501531A (ja) | 2003-01-14 |
FR2794759A1 (fr) | 2000-12-15 |
US20020169255A1 (en) | 2002-11-14 |
US6861491B2 (en) | 2005-03-01 |
CN1153795C (zh) | 2004-06-16 |
EP1183296B1 (fr) | 2004-04-28 |
DE60010255D1 (de) | 2004-06-03 |
CN1354762A (zh) | 2002-06-19 |
FR2794759B1 (fr) | 2002-07-12 |
ATE265483T1 (de) | 2004-05-15 |
AU5411600A (en) | 2000-12-28 |
KR20020016823A (ko) | 2002-03-06 |
CA2375721A1 (fr) | 2000-12-14 |
ES2219348T3 (es) | 2004-12-01 |
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