EP2238193A1 - Verfahren zur herstellung hochreaktiver uretdiongruppenhaltiger polyurethanzusammensetzungen im dryblend - Google Patents
Verfahren zur herstellung hochreaktiver uretdiongruppenhaltiger polyurethanzusammensetzungen im dryblendInfo
- Publication number
- EP2238193A1 EP2238193A1 EP08872017A EP08872017A EP2238193A1 EP 2238193 A1 EP2238193 A1 EP 2238193A1 EP 08872017 A EP08872017 A EP 08872017A EP 08872017 A EP08872017 A EP 08872017A EP 2238193 A1 EP2238193 A1 EP 2238193A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- compositions according
- compositions
- component
- acid
- proportion
- 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.)
- Ceased
Links
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- 239000004408 titanium dioxide Substances 0.000 description 1
- IPILPUZVTYHGIL-UHFFFAOYSA-M tributyl(methyl)azanium;chloride Chemical compound [Cl-].CCCC[N+](C)(CCCC)CCCC IPILPUZVTYHGIL-UHFFFAOYSA-M 0.000 description 1
- DXJLCRNXYNRGRA-UHFFFAOYSA-M tributyl(methyl)azanium;iodide Chemical compound [I-].CCCC[N+](C)(CCCC)CCCC DXJLCRNXYNRGRA-UHFFFAOYSA-M 0.000 description 1
- SEACXNRNJAXIBM-UHFFFAOYSA-N triethyl(methyl)azanium Chemical compound CC[N+](C)(CC)CC SEACXNRNJAXIBM-UHFFFAOYSA-N 0.000 description 1
- GRVPDGGTLNKOBZ-UHFFFAOYSA-M triethyl(methyl)azanium;bromide Chemical compound [Br-].CC[N+](C)(CC)CC GRVPDGGTLNKOBZ-UHFFFAOYSA-M 0.000 description 1
- NDPWCNORTYFYDW-UHFFFAOYSA-M triethyl(methyl)azanium;iodide Chemical compound [I-].CC[N+](C)(CC)CC NDPWCNORTYFYDW-UHFFFAOYSA-M 0.000 description 1
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
- GNMJFQWRASXXMS-UHFFFAOYSA-M trimethyl(phenyl)azanium;bromide Chemical compound [Br-].C[N+](C)(C)C1=CC=CC=C1 GNMJFQWRASXXMS-UHFFFAOYSA-M 0.000 description 1
- YFHICDDUDORKJB-UHFFFAOYSA-N trimethylene carbonate Chemical compound O=C1OCCCO1 YFHICDDUDORKJB-UHFFFAOYSA-N 0.000 description 1
- ZNEOHLHCKGUAEB-UHFFFAOYSA-N trimethylphenylammonium Chemical compound C[N+](C)(C)C1=CC=CC=C1 ZNEOHLHCKGUAEB-UHFFFAOYSA-N 0.000 description 1
- 150000004072 triols Chemical class 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
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
- C08G18/77—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
- C08G18/08—Processes
- C08G18/16—Catalysts
- C08G18/166—Catalysts not provided for in the groups C08G18/18 - C08G18/26
- C08G18/168—Organic compounds
-
- 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
- C08G18/1875—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
- C08G18/28—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
- C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
-
- 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
- C08G2150/00—Compositions for coatings
- C08G2150/20—Compositions for powder coatings
Definitions
- Hydroxyl-terminated, polyaddition compounds containing uretdione groups are the subject of EP 669 353. Due to their functionality of two, they have improved resistance to solvents.
- the powder coating compositions based on these polyisocyanates containing uretdione groups have in common that they do not emit volatile compounds during the curing reaction. However, the baking temperatures are at least 180 ° C at a high level.
- uretdione-bearing polyisocyanates to uretdione hardeners A) includes the reaction of the free NCO groups with hydroxyl-containing monomers or polymers, such as.
- polyesters polythioethers, polyethers, polycaprolactams, polyepoxides, polyester amides, polyurethanes or low molecular weight di-, tri- and / or tetra alcohols as chain extenders and optionally monoamines and / or monoalcohols as chain terminators and has been described frequently (EP 669 353, EP 669 354, DE 30 30 572, EP 639 598 or EP 803 524).
- the hardeners may also have isocyanurate, biuret, allophanate, urethane and / or urea structures.
- the proportion of the catalysts B) in the composition according to the invention is preferably 0.1 to 5 wt .-%, preferably from 0.3 to 3 wt .-%, based on the total composition.
- Tetraethylammonium benzoate and tetrabutylammonium hydroxide are particularly preferably used as catalyst B).
- the proportion of co-catalysts as component C) is in particular 0.1 to 5 wt .-%, preferably 0.3 to 3 wt .-%, based on the
- ethylene glycol 1, 2- and 1, 3-propylene glycol, 1, 4- and 2,3-butylene glycol, di-ß-hydroxyethylbutandiol, 1, 6- hexanediol, 1, 8-octanediol, neopentyl glycol, cyclohexanediol, bis- (1, 4-hydroxymethyl) -propane, 2-methylpropanediol-1, 3.
- polyesters of the abovementioned polycarboxylic acids or derivatives thereof and polyphenols such as hydroquinone, bisphenol A, 4,4'-dihydroxybiphenyl or bis (4-hydroxyphenyl) sulfone, or polyesters of Carbonic acid consisting of hydroquinone, diphenylolpropane, p-xylylene glycol, ethylene glycol, butanediol or hexanediol-1, 6 and other polyols by conventional condensation reactions, eg. B.
- polyphenols such as hydroquinone, bisphenol A, 4,4'-dihydroxybiphenyl or bis (4-hydroxyphenyl) sulfone
- polyesters of Carbonic acid consisting of hydroquinone, diphenylolpropane, p-xylylene glycol, ethylene glycol, butanediol or hexanediol-1, 6 and other polyols by conventional condensation reactions, e
- polymers D) are also z.
- polythioethers polyacetals, polyepoxides, polyester or polyurethanes in the molecular weight range from 250 to 8500 g / mol, which have isocyanate-reactive hydroxyl groups suitable.
- Powder sintered in a hot air oven to the tissue surface Powder sintered in a hot air oven to the tissue surface.
- the two outer stripes are discarded.
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Paints Or Removers (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Polyurethanes Or Polyureas (AREA)
Abstract
Description
Claims
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE102008007386A DE102008007386A1 (de) | 2008-02-01 | 2008-02-01 | Verfahren zur Herstellung hochreaktiver uretdiongruppenhaltiger Polyurethanzusammensetzungen im Dryblend |
PCT/EP2008/065823 WO2009095117A1 (de) | 2008-02-01 | 2008-11-19 | Verfahren zur herstellung hochreaktiver uretdiongruppenhaltiger polyurethanzusammensetzungen im dryblend |
Publications (1)
Publication Number | Publication Date |
---|---|
EP2238193A1 true EP2238193A1 (de) | 2010-10-13 |
Family
ID=40344865
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP08872017A Ceased EP2238193A1 (de) | 2008-02-01 | 2008-11-19 | Verfahren zur herstellung hochreaktiver uretdiongruppenhaltiger polyurethanzusammensetzungen im dryblend |
Country Status (9)
Country | Link |
---|---|
US (1) | US8702899B2 (de) |
EP (1) | EP2238193A1 (de) |
JP (1) | JP6108652B2 (de) |
KR (1) | KR20100115750A (de) |
CN (1) | CN101497686B (de) |
CA (1) | CA2713399A1 (de) |
DE (1) | DE102008007386A1 (de) |
TW (1) | TWI469999B (de) |
WO (1) | WO2009095117A1 (de) |
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DE102007062316A1 (de) * | 2007-12-21 | 2009-06-25 | Evonik Degussa Gmbh | Reaktive Isocyanatzusammensetzungen |
DE102008002703A1 (de) | 2008-06-27 | 2009-12-31 | Evonik Degussa Gmbh | Hochreaktive, Uretdiongruppen haltige Polyurethanzusammensetzungen, die metallfreie Acetylacetonate enthalten |
US8790755B2 (en) * | 2009-11-27 | 2014-07-29 | Sunstar Engineering Inc. | Adhering method using electrostatic powder adhesive, and powder adhesive to be used in adhering method |
US9133377B2 (en) * | 2010-05-20 | 2015-09-15 | A. Raymond Et Cie | Adhesive polyurethane powder capable of being activated by heat |
DE102010041247A1 (de) * | 2010-09-23 | 2012-03-29 | Evonik Degussa Gmbh | Verfahren zur Herstellung von lagerstabilen Polyurethan-Prepregs und daraus hergestellte Formkörper aus Polyurethanzusammensetzung in Lösung |
DE102011006163A1 (de) | 2011-03-25 | 2012-09-27 | Evonik Degussa Gmbh | Lagerstabile Polyurethan-Prepregs und daraus hergestellte Formkörper aus Polyurethanzusammensetzung mit flüssigen Harzkomponenten |
CN102675589B (zh) * | 2012-05-24 | 2013-08-07 | 黑龙江大学 | 以异氰酸酯基三苯胺为原料制备的电致变色材料及其制备方法 |
CN102702461B (zh) * | 2012-05-24 | 2013-12-25 | 黑龙江大学 | 一种具有电致变色性能的聚氨酯及其制备方法 |
DE102012219324A1 (de) | 2012-10-23 | 2014-04-24 | Evonik Industries Ag | Zusammensetzungen umfassend alkoxysilanhaltige Isocyanateund saure Stabilisatoren |
DE102013204550A1 (de) | 2013-03-15 | 2014-09-18 | Evonik Industries Ag | Verwendung von Polyestern mit inhärentem Flammschutz in Kleb- und Dichtstoffen |
DE102014214130A1 (de) * | 2014-07-21 | 2016-01-21 | Evonik Degussa Gmbh | Hochreaktive, Uretdiongruppen haltige Polyurethanzusammensetzungen, die Carbonatsalze enthalten |
EP3253815B1 (de) | 2015-02-05 | 2022-06-15 | Evonik Operations GmbH | Isocyanatfreie synthese carbonatmodifizierter polymere |
ES2720001T3 (es) | 2015-03-02 | 2019-07-17 | Evonik Degussa Gmbh | Pegamentos con valores de VOC y empañamiento reducidos |
CN107278212B (zh) | 2015-03-02 | 2020-03-10 | 赢创德固赛有限公司 | 具有低voc和雾化值的粘合剂 |
EP3243863A1 (de) | 2016-05-09 | 2017-11-15 | Evonik Degussa GmbH | Verwendung von block-copolymeren in klebstoffen |
CN107011774B (zh) * | 2017-04-10 | 2020-10-02 | 立邦涂料(天津)有限公司 | 一种高硬度粉末涂料组合物及其制备方法和用途 |
CN107236444A (zh) * | 2017-06-05 | 2017-10-10 | 靖江励创信息科技有限公司 | 一种疏水阻燃聚氨酯粉末涂料的制备方法 |
EP3543270A1 (de) | 2018-03-23 | 2019-09-25 | Covestro Deutschland AG | Katalysatorsystem für uretdiondispersionen |
WO2019180128A1 (de) | 2018-03-23 | 2019-09-26 | Covestro Deutschland Ag | Wässrige uretdiongruppenhaltige zusammensetzungen und verfahren zu deren herstellung |
CN108608604B (zh) * | 2018-05-22 | 2020-06-16 | 郑州大学 | 一种塑料废弃物的分离方法 |
EP3636687A1 (de) | 2018-10-12 | 2020-04-15 | Evonik Operations GmbH | Thermisch lösbare reaktivklebstoffe |
CN110305294B (zh) * | 2019-07-15 | 2021-04-20 | 万华化学集团股份有限公司 | 一种存储稳定的含有脲二酮基团的多异氰酸酯的制备方法 |
EP4212337A4 (de) | 2020-10-16 | 2024-04-10 | Tosoh Corp | Polycarbonatharz und verfahren zur herstellung davon, zusammensetzung und verfahren zur herstellung davon, urethanharz und wässrige urethanharzdispersion |
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-
2008
- 2008-02-01 DE DE102008007386A patent/DE102008007386A1/de not_active Withdrawn
- 2008-11-19 JP JP2010544601A patent/JP6108652B2/ja not_active Expired - Fee Related
- 2008-11-19 US US12/809,911 patent/US8702899B2/en not_active Expired - Fee Related
- 2008-11-19 KR KR1020107017113A patent/KR20100115750A/ko not_active Application Discontinuation
- 2008-11-19 WO PCT/EP2008/065823 patent/WO2009095117A1/de active Application Filing
- 2008-11-19 CA CA2713399A patent/CA2713399A1/en not_active Abandoned
- 2008-11-19 EP EP08872017A patent/EP2238193A1/de not_active Ceased
-
2009
- 2009-01-23 TW TW98103014A patent/TWI469999B/zh not_active IP Right Cessation
- 2009-01-24 CN CN200910009944.4A patent/CN101497686B/zh not_active Expired - Fee Related
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Also Published As
Publication number | Publication date |
---|---|
JP2011511109A (ja) | 2011-04-07 |
US8702899B2 (en) | 2014-04-22 |
JP6108652B2 (ja) | 2017-04-05 |
CN101497686A (zh) | 2009-08-05 |
DE102008007386A1 (de) | 2009-08-06 |
US20100263792A1 (en) | 2010-10-21 |
CN101497686B (zh) | 2014-10-22 |
TWI469999B (zh) | 2015-01-21 |
CA2713399A1 (en) | 2009-08-06 |
TW200948841A (en) | 2009-12-01 |
WO2009095117A1 (de) | 2009-08-06 |
KR20100115750A (ko) | 2010-10-28 |
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