JP2011511109A - ドライブレンドでの高反応性ウレトジオン基含有ポリウレタン組成物の製造方法 - Google Patents
ドライブレンドでの高反応性ウレトジオン基含有ポリウレタン組成物の製造方法 Download PDFInfo
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- JP2011511109A JP2011511109A JP2010544601A JP2010544601A JP2011511109A JP 2011511109 A JP2011511109 A JP 2011511109A JP 2010544601 A JP2010544601 A JP 2010544601A JP 2010544601 A JP2010544601 A JP 2010544601A JP 2011511109 A JP2011511109 A JP 2011511109A
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- FISRGBICZQXBOD-UHFFFAOYSA-N methane phosphoric acid Chemical compound C.C.OP(O)(O)=O FISRGBICZQXBOD-UHFFFAOYSA-N 0.000 description 1
- JDZSWRCOINFOQI-UHFFFAOYSA-M methyl(triphenyl)azanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[N+](C=1C=CC=CC=1)(C)C1=CC=CC=C1 JDZSWRCOINFOQI-UHFFFAOYSA-M 0.000 description 1
- OGGXBSGFTTXROS-UHFFFAOYSA-M methyl(triphenyl)azanium;chloride Chemical compound [Cl-].C=1C=CC=CC=1[N+](C=1C=CC=CC=1)(C)C1=CC=CC=C1 OGGXBSGFTTXROS-UHFFFAOYSA-M 0.000 description 1
- GGSHUYPVVIISTD-UHFFFAOYSA-M methyl(triphenyl)azanium;iodide Chemical compound [I-].C=1C=CC=CC=1[N+](C=1C=CC=CC=1)(C)C1=CC=CC=C1 GGSHUYPVVIISTD-UHFFFAOYSA-M 0.000 description 1
- AWTHIIUZRKZUJY-UHFFFAOYSA-M methyl(tripropyl)azanium;bromide Chemical compound [Br-].CCC[N+](C)(CCC)CCC AWTHIIUZRKZUJY-UHFFFAOYSA-M 0.000 description 1
- ZUCOWQZUGKUQCH-UHFFFAOYSA-M methyl(tripropyl)azanium;chloride Chemical compound [Cl-].CCC[N+](C)(CCC)CCC ZUCOWQZUGKUQCH-UHFFFAOYSA-M 0.000 description 1
- UARUINOVQHEYKN-UHFFFAOYSA-M methyl(tripropyl)azanium;iodide Chemical compound [I-].CCC[N+](C)(CCC)CCC UARUINOVQHEYKN-UHFFFAOYSA-M 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- OEIJHBUUFURJLI-UHFFFAOYSA-N octane-1,8-diol Chemical compound OCCCCCCCCO OEIJHBUUFURJLI-UHFFFAOYSA-N 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- AHHWIHXENZJRFG-UHFFFAOYSA-N oxetane Chemical compound C1COC1 AHHWIHXENZJRFG-UHFFFAOYSA-N 0.000 description 1
- PTLZMJYQEBOHHM-UHFFFAOYSA-N oxiran-2-ylmethyl dodecanoate Chemical compound CCCCCCCCCCCC(=O)OCC1CO1 PTLZMJYQEBOHHM-UHFFFAOYSA-N 0.000 description 1
- KYVUJPJYTYQNGJ-UHFFFAOYSA-N oxiran-2-ylmethyl hexadecanoate Chemical compound CCCCCCCCCCCCCCCC(=O)OCC1CO1 KYVUJPJYTYQNGJ-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 238000007719 peel strength test Methods 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- ZLLNYWQSSYUXJM-UHFFFAOYSA-N phenol tetraphenylphosphanium Chemical compound C1(=CC=CC=C1)O.C1(=CC=CC=C1)[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1 ZLLNYWQSSYUXJM-UHFFFAOYSA-N 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- YVURAEQQLUQPFO-UHFFFAOYSA-N phosphoric acid;styrene Chemical class OP(O)(O)=O.C=CC1=CC=CC=C1 YVURAEQQLUQPFO-UHFFFAOYSA-N 0.000 description 1
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 1
- 239000006223 plastic coating Substances 0.000 description 1
- YBTMSVKMINMVAZ-UHFFFAOYSA-N pocl3 benzene Chemical compound ClP(Cl)(Cl)=O.C1=CC=CC=C1 YBTMSVKMINMVAZ-UHFFFAOYSA-N 0.000 description 1
- 229920001748 polybutylene Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920006324 polyoxymethylene Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920005591 polysilicon Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920001289 polyvinyl ether Polymers 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- AOLHFTSRLXHBNU-UHFFFAOYSA-M propanoate;tetrabutylazanium Chemical compound CCC([O-])=O.CCCC[N+](CCCC)(CCCC)CCCC AOLHFTSRLXHBNU-UHFFFAOYSA-M 0.000 description 1
- XNWSMNKRGNKRKP-UHFFFAOYSA-M propanoate;tetramethylazanium Chemical compound CCC([O-])=O.C[N+](C)(C)C XNWSMNKRGNKRKP-UHFFFAOYSA-M 0.000 description 1
- VTIZRIDYIWLCRE-UHFFFAOYSA-M propanoate;tetrapropylazanium Chemical compound CCC([O-])=O.CCC[N+](CCC)(CCC)CCC VTIZRIDYIWLCRE-UHFFFAOYSA-M 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000003892 spreading Methods 0.000 description 1
- 230000007480 spreading Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 150000005622 tetraalkylammonium hydroxides Chemical class 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- MCZDHTKJGDCTAE-UHFFFAOYSA-M tetrabutylazanium;acetate Chemical compound CC([O-])=O.CCCC[N+](CCCC)(CCCC)CCCC MCZDHTKJGDCTAE-UHFFFAOYSA-M 0.000 description 1
- WGYONVRJGWHMKV-UHFFFAOYSA-M tetrabutylazanium;benzoate Chemical compound [O-]C(=O)C1=CC=CC=C1.CCCC[N+](CCCC)(CCCC)CCCC WGYONVRJGWHMKV-UHFFFAOYSA-M 0.000 description 1
- SNMZANHSFVMKKA-UHFFFAOYSA-M tetrabutylazanium;formate Chemical compound [O-]C=O.CCCC[N+](CCCC)(CCCC)CCCC SNMZANHSFVMKKA-UHFFFAOYSA-M 0.000 description 1
- DPKBAXPHAYBPRL-UHFFFAOYSA-M tetrabutylazanium;iodide Chemical compound [I-].CCCC[N+](CCCC)(CCCC)CCCC DPKBAXPHAYBPRL-UHFFFAOYSA-M 0.000 description 1
- HJBZFPLBRXFZNE-UHFFFAOYSA-M tetrabutylphosphanium fluoride hydrofluoride Chemical compound F.[F-].CCCC[P+](CCCC)(CCCC)CCCC HJBZFPLBRXFZNE-UHFFFAOYSA-M 0.000 description 1
- GFZMLBWMGBLIDI-UHFFFAOYSA-M tetrabutylphosphanium;acetate Chemical compound CC([O-])=O.CCCC[P+](CCCC)(CCCC)CCCC GFZMLBWMGBLIDI-UHFFFAOYSA-M 0.000 description 1
- WHDWTYUVZOXXKX-UHFFFAOYSA-M tetrabutylphosphanium;formate Chemical compound [O-]C=O.CCCC[P+](CCCC)(CCCC)CCCC WHDWTYUVZOXXKX-UHFFFAOYSA-M 0.000 description 1
- DFQPZDGUFQJANM-UHFFFAOYSA-M tetrabutylphosphanium;hydroxide Chemical compound [OH-].CCCC[P+](CCCC)(CCCC)CCCC DFQPZDGUFQJANM-UHFFFAOYSA-M 0.000 description 1
- CBXCPBUEXACCNR-UHFFFAOYSA-N tetraethylammonium Chemical compound CC[N+](CC)(CC)CC CBXCPBUEXACCNR-UHFFFAOYSA-N 0.000 description 1
- YMBCJWGVCUEGHA-UHFFFAOYSA-M tetraethylammonium chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC YMBCJWGVCUEGHA-UHFFFAOYSA-M 0.000 description 1
- UQFSVBXCNGCBBW-UHFFFAOYSA-M tetraethylammonium iodide Chemical compound [I-].CC[N+](CC)(CC)CC UQFSVBXCNGCBBW-UHFFFAOYSA-M 0.000 description 1
- GTCDARUMAMVCRO-UHFFFAOYSA-M tetraethylazanium;acetate Chemical compound CC([O-])=O.CC[N+](CC)(CC)CC GTCDARUMAMVCRO-UHFFFAOYSA-M 0.000 description 1
- DDDVBYGLVAHHCD-UHFFFAOYSA-M tetraethylazanium;formate Chemical compound [O-]C=O.CC[N+](CC)(CC)CC DDDVBYGLVAHHCD-UHFFFAOYSA-M 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- UFDHBDMSHIXOKF-UHFFFAOYSA-N tetrahydrophthalic acid Natural products OC(=O)C1=C(C(O)=O)CCCC1 UFDHBDMSHIXOKF-UHFFFAOYSA-N 0.000 description 1
- DDFYFBUWEBINLX-UHFFFAOYSA-M tetramethylammonium bromide Chemical compound [Br-].C[N+](C)(C)C DDFYFBUWEBINLX-UHFFFAOYSA-M 0.000 description 1
- MRYQZMHVZZSQRT-UHFFFAOYSA-M tetramethylazanium;acetate Chemical compound CC([O-])=O.C[N+](C)(C)C MRYQZMHVZZSQRT-UHFFFAOYSA-M 0.000 description 1
- IEVVGBFMAHJELO-UHFFFAOYSA-M tetramethylazanium;benzoate Chemical compound C[N+](C)(C)C.[O-]C(=O)C1=CC=CC=C1 IEVVGBFMAHJELO-UHFFFAOYSA-M 0.000 description 1
- WWIYWFVQZQOECA-UHFFFAOYSA-M tetramethylazanium;formate Chemical compound [O-]C=O.C[N+](C)(C)C WWIYWFVQZQOECA-UHFFFAOYSA-M 0.000 description 1
- RXMRGBVLCSYIBO-UHFFFAOYSA-M tetramethylazanium;iodide Chemical compound [I-].C[N+](C)(C)C RXMRGBVLCSYIBO-UHFFFAOYSA-M 0.000 description 1
- PXJUBOLFJDSAQQ-UHFFFAOYSA-M tetrapropylazanium;acetate Chemical compound CC([O-])=O.CCC[N+](CCC)(CCC)CCC PXJUBOLFJDSAQQ-UHFFFAOYSA-M 0.000 description 1
- QOHLYFXRPYZSJX-UHFFFAOYSA-M tetrapropylazanium;benzoate Chemical compound [O-]C(=O)C1=CC=CC=C1.CCC[N+](CCC)(CCC)CCC QOHLYFXRPYZSJX-UHFFFAOYSA-M 0.000 description 1
- LENBOWGJEQXFCI-UHFFFAOYSA-M tetrapropylazanium;formate Chemical compound [O-]C=O.CCC[N+](CCC)(CCC)CCC LENBOWGJEQXFCI-UHFFFAOYSA-M 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- DHAWHVVWUNNONG-UHFFFAOYSA-M tributyl(methyl)azanium;bromide Chemical compound [Br-].CCCC[N+](C)(CCCC)CCCC DHAWHVVWUNNONG-UHFFFAOYSA-M 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
- GRVPDGGTLNKOBZ-UHFFFAOYSA-M triethyl(methyl)azanium;bromide Chemical compound [Br-].CC[N+](C)(CC)CC GRVPDGGTLNKOBZ-UHFFFAOYSA-M 0.000 description 1
- NIUZJTWSUGSWJI-UHFFFAOYSA-M triethyl(methyl)azanium;chloride Chemical compound [Cl-].CC[N+](C)(CC)CC NIUZJTWSUGSWJI-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
- 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
- MQAYPFVXSPHGJM-UHFFFAOYSA-M trimethyl(phenyl)azanium;chloride Chemical compound [Cl-].C[N+](C)(C)C1=CC=CC=C1 MQAYPFVXSPHGJM-UHFFFAOYSA-M 0.000 description 1
- YFHICDDUDORKJB-UHFFFAOYSA-N trimethylene carbonate Chemical compound O=C1OCCCO1 YFHICDDUDORKJB-UHFFFAOYSA-N 0.000 description 1
- 150000004072 triols Chemical class 0.000 description 1
- 239000008096 xylene Substances 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
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
A)少なくとも1つのウレトジオン基含有硬化剤、
B)少なくとも1つの第四級アンモニウム塩、又はホスホニウム塩、
C)エポキシド又はアセチルアセトネートの形での少なくとも1つの助触媒、
D)少なくとも1つのモノマー、オリゴマー若しくはポリマーのモノアルコール又はポリアルコール、場合により
E)モノマー又はポリマー形態の少なくとも1つの酸、及び場合により
F)助剤及び添加剤、及び/又はさらなる触媒
を含む、融点が40℃超の粉末組成物である。
OH価はDIN53240−2により測定される。
a)A)、C)、及びD)から成る均質混合物
DYNACOLL 7330(成分D)61.65gを、120℃で鋼製の器(サーモスタット調整)内に装入し、そして約1時間で撹拌しながら溶融させる。引き続き同一の温度で、VESTAGON BF 9030(成分A)35.35gを部分量で添加し、そして約1.5〜2時間、後撹拌する。その後、さらにAraldit PT 910(成分C)1gを添加し、そしてさらに15分、撹拌する。均質な溶融物が出来次第、生成物を移し替えることが出来る。冷ました溶融物を家庭用粉砕機(Braun社、4142型)内で予備粉砕し、その後に粉砕する。粉砕工程はローター式高速ミル(Rotor-Schnell-Muehle)(Fritsch社Pulverisette 14型)を用いて、液体窒素を用いながら行う。N2による冷却が原因で、ミル内での生成物の接着は防止される。湿ってしまった生成物はこの後、真空乾燥棚で室温で乾燥させなければならない(50mbar)。生成物が乾燥し次第(その流動性を視覚的に判断して)、その生成物を分析ふるい分け機(Retsch社、AS200 Basic型)に入れ、そして<63μmの粒径にふるい分けする。
TEAB(成分B)50gを、脱塩水150mlとともに500mlの丸底フラスコに装入し、そして室温で5分以内に溶融させる。その後、Sipernat 2200(担体)50gをこれに加え、そしてロータリーエバポレータを用いて50℃、約6mbarで蒸発させる。可能な限り乾燥させた生成物を、混合器内で微粉砕し、そして真空乾燥棚内で50℃(50mbar)で質量定数まで後乾燥させる。引き続き、この生成物を粉砕し、<63μmにふるい分けする。
均質化され、微粉砕された、A)、C)、及びD)から成る混合物(実施例1a)98gを、工程b)からの混合物2gと一緒に、1lのタービュラ−プラスチック容器内に秤量し、そして30分間、揺動式混合機(Bachhofen AG製、Turbula, System Schatz型)を用いて46回転/分で混合する。この後、混合物を乾燥板に広げ、そして約15〜20分間80℃で焼結させる。その後再度粉砕し、そして100〜200μmの粒径にふるい分けする。融点が約90℃、NCO含分が4.40%(理論値:4.37%)の粉末が得られる。NCO価は4週間後でも、室温でほぼ一定(4.20%)のままであり、このことは本発明による混合物の貯蔵安定性を証明している。
DYNACOLL 7330 61.65gを、120℃で鋼製の器(サーモスタット調整)内に装入し、そして約1時間以内に撹拌しながら溶融させる。引き続き、同一の温度でVESTAGON BF 9030 35.35g、PT 910 1g、及びTEABとSipernatとから成る混合物2gを添加する。
木綿織布から、110mm×110mmの大きさの布を二枚切り取る。木綿布の下半分に粉末組成物を、100mm×50mmの接着すべき範囲に、メッシュ幅160μm未満のふるいを用いて散布する。その負荷量は、約30g/m2である。その粉末を5分間熱風炉内で、粉末の融点を10℃超える温度で織布表面に焼結させる。冷却後、接着剤で予備被覆された木綿布を、被覆されていない布とプレス機内で140℃の温度で10分間、10barの圧力で積層化させる。1日後に織布複合体から、幅15mm、長さ110mmの試験片を切り取り、この際に接着長さは50mmである。外側の試験片は両方とも退けられる(verworfen)。
本発明による組成物1c)に対する繊維接着は、Fmax値が6.9Nという良好な接着性をもたらす。本発明によるものではない組成物1d2)は、もはや溶融することができず、従って接着には用いることができない。
Claims (15)
- A)少なくとも1つのウレトジオン基含有硬化剤、
B)少なくとも1つの第四級アンモニウム塩、又はホスホニウム塩、
C)エポキシド又はアセチルアセトネートの形での少なくとも1つの助触媒、
D)少なくとも1つのモノマー、オリゴマー若しくはポリマーのモノアルコール又はポリアルコール、場合により
E)モノマー又はポリマー形態の少なくとも1つの酸、及び場合により
F)助剤及び添加剤、及び/又はさらなる触媒
を含む、融点が40℃超の粉末組成物。 - 前記硬化剤A)が芳香族、脂肪族、(環式)脂肪族、及び/又は脂環式ポリイソシアネート、及び遊離NCO含分が5質量%未満で、かつウレトジオン基含分が1〜25質量%のヒドロキシ基含有化合物をベースとすることを特徴とする、請求項1に記載の組成物。
- A)の割合が、全組成物に対して5〜99質量%であることを特徴とする、請求項1又は2に記載の組成物。
- B)が、対イオンとしてハロゲン又は有機若しくは無機の酸アニオンを有するテトラアルキルアンモニウム塩又はホスホニウム塩であることを特徴とする、請求項1から3までのいずれか1項に記載の組成物。
- B)の割合が、全組成物に対して0.1〜5質量%であることを特徴とする、請求項1から4までのいずれか1項に記載の組成物。
- テトラエチルアンモニウムベンゾエート及びテトラブチルアンモニウムヒドロキシドをB)として使用することを特徴とする、請求項1から5までのいずれか1項に記載の組成物。
- 成分C)の割合が、全組成物に対して0.1〜5質量%であることを特徴とする、請求項1から6までのいずれか1項に記載の組成物。
- 成分D)としてポリエステルを使用することを特徴とする、請求項1から7までのいずれか1項に記載の組成物。
- 成分D)として、OH価が15〜150であり、かつ平均分子量が500〜8000g/molのヒドロキシ基含有ポリエステルを使用することを特徴とする、請求項1から8までのいずれか1項に記載の組成物。
- 成分D)の割合が、全組成物に対して1〜95質量%であることを特徴とする、請求項1から9までのいずれか1項に記載の組成物。
- 成分F)として均展剤、光安定剤、充填剤、及び顔料を使用することを特徴とする、請求項1から10までのいずれか1項に記載の組成物。
- 請求項1から11までのいずれか1項に記載の粉末組成物の製造方法であって、
各成分A)〜F)の乾燥混合、又は各成分A)〜F)の均質混合物の乾燥混合を含むが、ただし成分B)及びC)は同一の均質混合物には存在しない、前記製造方法。 - 請求項1から11までのいずれか1項に記載の粉末組成物を含む、接着剤組成物、粉末塗料、金属被覆組成物、木材被覆組成物、ガラス被覆組成物、皮革被覆組成物、及びプラスチック被覆組成物。
- 金属基材、プラスチック基材、ガラス基材、木材基材、繊維機材、紙基材、又は皮革基材、繊維複合材の接着を製造するための、請求項1から11までのいずれか1項に記載の粉末組成物の使用。
- 金属基材、プラスチック基材、ガラス基材、木材基材、又は皮革基材上に塗料被覆を製造するための、請求項1から11までのいずれか1項に記載の粉末組成物の使用。
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DE102008007386.5 | 2008-02-01 | ||
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 |
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EP (1) | EP2238193A1 (ja) |
JP (1) | JP6108652B2 (ja) |
KR (1) | KR20100115750A (ja) |
CN (1) | CN101497686B (ja) |
CA (1) | CA2713399A1 (ja) |
DE (1) | DE102008007386A1 (ja) |
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Families Citing this family (23)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
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 (en) | 2020-10-16 | 2024-04-10 | Tosoh Corp | POLYCARBONATE RESIN AND METHOD FOR PREPARING THE SAME, COMPOSITION AND METHOD FOR PREPARING THE SAME, URETHANE RESIN AND AQUEOUS URETHANE RESIN DISPERSION |
Citations (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2003238891A (ja) * | 2002-02-11 | 2003-08-27 | Degussa Ag | ポリウレタン粉末塗料組成物、その製造方法、その硬化のための触媒並びに木材被覆組成物、皮革被覆組成物、プラスチック被覆組成物及び金属被覆組成物 |
JP2004331954A (ja) * | 2003-05-03 | 2004-11-25 | Degussa Ag | 高反応性ポリウレタン粉末塗料組成物、その製造方法、該組成物のための効果触媒、粉末塗料被覆層の製造のための粉末塗料硬化剤、ポリマー及び触媒の使用並びに被覆組成物 |
JP2004331952A (ja) * | 2003-05-03 | 2004-11-25 | Degussa Ag | 高反応性ポリウレタン粉末塗料組成物、その製造方法、該組成物のための効果触媒、粉末塗料被覆層の製造のための粉末塗料硬化剤、ポリマー及び触媒の使用並びに被覆組成物 |
JP2005120374A (ja) * | 2003-10-15 | 2005-05-12 | Degussa Ag | 高反応性ポリウレタン−粉末塗料組成物、その製造方法、その使用、被覆組成物及び金属被覆物 |
JP2005126713A (ja) * | 2003-10-22 | 2005-05-19 | Degussa Ag | ポリウレタン−粉体塗料組成物、その製法、エポキシ基を末端基とするウレトジオン基含有重付加化合物とヒドロキシ基含有ポリマーとからの組成物のポリウレタン−粉体塗料組成物のための使用、被覆組成物および金属被覆 |
US20050239992A1 (en) * | 2004-04-27 | 2005-10-27 | Degussa Ag | Polyurethane composition which contains an uretdione group |
WO2005105879A1 (de) * | 2004-04-27 | 2005-11-10 | Degussa Ag | Uretdiongruppenhaltige polyurethanzusammensetzungen, welche bei niedriger temperatur härtbar sind und (teil-)kristalline harze enthalten |
US7019088B1 (en) * | 1998-12-10 | 2006-03-28 | Bayer Materialscience Ag | Hardenable materials which contain uretdione groups, method for the production and processing thereof, and their utilization |
WO2006040225A1 (de) * | 2004-10-07 | 2006-04-20 | Degussa Ag | Hoch reaktive uretdiongruppenhaltige polyurethanzusammensetzungen |
DE102006004077A1 (de) * | 2006-01-28 | 2007-08-02 | Degussa Gmbh | Verfahren zur Herstellung von hoch reaktiven uretdiongruppenhaltigen Polyurethanverbindungen |
JP2007530757A (ja) * | 2004-04-02 | 2007-11-01 | バイエル・マテリアルサイエンス・アクチェンゲゼルシャフト | 分離産物を含まない、低焼付温度を有するポリウレタン粉末被覆剤 |
US20070282089A1 (en) * | 2004-03-06 | 2007-12-06 | Degussa Ag | Method for producing solid highly-reactive polyurethane compositions containing uretdione groups |
Family Cites Families (25)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2220509A1 (en) | 1973-03-05 | 1974-10-04 | Du Pont | Glycidyl diesters of unsatd. dibasic acids - for coating compsns of low solvent content |
US3933759A (en) * | 1974-12-20 | 1976-01-20 | E. I. Du Pont De Nemours & Company | Heat-activatable, storage-stable polyurethane powders |
DE2712931A1 (de) | 1977-03-24 | 1978-09-28 | Veba Chemie Ag | Isocyanuratgruppen - und endstaendig- blockierte isocyanatgruppen - enthaltende verbindungen |
DE2735497A1 (de) | 1977-08-06 | 1979-02-15 | Veba Chemie Ag | Pulverfoermige polyurethanlacke |
DE3030572A1 (de) | 1980-08-13 | 1982-03-18 | Chemische Werke Hüls AG, 4370 Marl | Verfahren zur herstellung von uretdiongruppenhaltigen polyadditionsprodukten sowie die danach hergestellten produkte |
DE3030539A1 (de) | 1980-08-13 | 1982-04-01 | Chemische Werke Hüls AG, 4370 Marl | Verfahren zur herstellung von abspaltfreien polyurethan-pulverlacken sowie die danach hergestellten lacke |
DE3030513A1 (de) | 1980-08-13 | 1982-03-18 | Chemische Werke Hüls AG, 4370 Marl | Verfahren zur herstellung eines isocyanuratfreien uretdions aus isophorondiisocyanat sowie das danach hergestellte uretdion |
DE3437635A1 (de) | 1984-10-13 | 1986-04-17 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von uretdiongruppen aufweisenden verbindungen, die nach diesem verfahren erhaeltlichen verbindungen und ihre verwendung bei der herstellung von polyurethankunststoffen |
EP0288021B1 (en) * | 1987-04-24 | 1992-12-16 | Ppg Industries, Inc. | Stretched microporous material |
DE3739549C2 (de) | 1987-11-21 | 1994-10-27 | Huels Chemische Werke Ag | Verfahren zur Herstellung (cyclo)aliphatischer Uretdione |
DE3930669A1 (de) | 1989-09-14 | 1991-03-28 | Basf Ag | Verfahren zur herstellung von uretdiongruppen aufweisenden polyisocyanaten |
DE4327573A1 (de) | 1993-08-17 | 1995-02-23 | Bayer Ag | Uretdion-Pulverlackvernetzer mit niedriger Schmelzviskosität |
DE4406444A1 (de) | 1994-02-28 | 1995-08-31 | Huels Chemische Werke Ag | Hydroxyl- und uretdiongruppenhaltige Polyadditionsprodukte und Verfahren zu ihrer Herstellung sowie deren Verwendung zur Herstellung abspaltfreier Polyurethan-Pulverlacke hoher Reaktivität und die danach hergestellten Polyurethan-Pulverlacke |
DE4406445C2 (de) | 1994-02-28 | 2002-10-31 | Degussa | Verfahren zur Herstellung von uretdiongruppenhaltigen Polyadditionsprodukten und deren Verwendung in Polyurethan-Lacksystemen |
DE19616496A1 (de) | 1996-04-25 | 1997-10-30 | Bayer Ag | Abspaltfreier Polyurethan-Pulverlack mit niedriger Einbrenntemperatur |
DE10346957A1 (de) | 2003-10-09 | 2005-05-04 | Degussa | Hochreaktive, flüssige uretdiongruppenhaltige Polyurenthansysteme, die bei niedriger Temperatur härtbar sind |
DE10346958A1 (de) | 2003-10-09 | 2005-05-12 | Degussa | Uretdiongruppenhaltige Polyurethanzusammensetzungen, welche bei niedriger Temperatur härtbar sind |
DE102004011005A1 (de) | 2004-03-06 | 2005-09-22 | Degussa Ag | Bei niedriger Temperatur härtbare uretdiongruppenhaltige Polyurethanzusammensetzungen |
DE102004062588A1 (de) | 2004-12-24 | 2006-07-06 | Degussa Ag | Hochreaktive uretdiongruppenhaltige Polyurethanzusammensetzungen auf Basis von 1,4-Diisocyanatocyclohexylmethan |
DE102005013329A1 (de) | 2005-03-23 | 2006-11-16 | Degussa Ag | Niedrigviskose uretdiongruppenhaltige Polyadditionsverbindungen, Verfahren zur Herstellung und Verwendung |
DE102006042494A1 (de) * | 2006-09-07 | 2008-03-27 | Evonik Degussa Gmbh | Bei niedriger Temperatur härtbare, uretdiongruppenhaltige Polyurethanzusammensetzungen mit quartären Ammoniumhalogeniden |
DE102006045003A1 (de) * | 2006-09-23 | 2008-03-27 | Bayer Materialscience Ag | Polyurethan-Pulverlack |
US20080265201A1 (en) | 2007-04-26 | 2008-10-30 | Degussa Gmbh | Low-temperature-curable polyurethane compositions with uretdione groups, containing polymers based on polyols that carry secondary oh groups |
WO2008138855A1 (de) * | 2007-05-11 | 2008-11-20 | Evonik Degussa Gmbh | Bei niedriger temperatur härtbare, uretdiongruppen aufweisende polyurethanzusammensetzungen enthaltend polymere auf der basis von sekundären oh-gruppen tragenden polyolen |
DE102007062316A1 (de) | 2007-12-21 | 2009-06-25 | Evonik Degussa Gmbh | Reaktive Isocyanatzusammensetzungen |
-
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
Patent Citations (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7019088B1 (en) * | 1998-12-10 | 2006-03-28 | Bayer Materialscience Ag | Hardenable materials which contain uretdione groups, method for the production and processing thereof, and their utilization |
JP2003238891A (ja) * | 2002-02-11 | 2003-08-27 | Degussa Ag | ポリウレタン粉末塗料組成物、その製造方法、その硬化のための触媒並びに木材被覆組成物、皮革被覆組成物、プラスチック被覆組成物及び金属被覆組成物 |
JP2004331954A (ja) * | 2003-05-03 | 2004-11-25 | Degussa Ag | 高反応性ポリウレタン粉末塗料組成物、その製造方法、該組成物のための効果触媒、粉末塗料被覆層の製造のための粉末塗料硬化剤、ポリマー及び触媒の使用並びに被覆組成物 |
JP2004331952A (ja) * | 2003-05-03 | 2004-11-25 | Degussa Ag | 高反応性ポリウレタン粉末塗料組成物、その製造方法、該組成物のための効果触媒、粉末塗料被覆層の製造のための粉末塗料硬化剤、ポリマー及び触媒の使用並びに被覆組成物 |
JP2005120374A (ja) * | 2003-10-15 | 2005-05-12 | Degussa Ag | 高反応性ポリウレタン−粉末塗料組成物、その製造方法、その使用、被覆組成物及び金属被覆物 |
JP2005126713A (ja) * | 2003-10-22 | 2005-05-19 | Degussa Ag | ポリウレタン−粉体塗料組成物、その製法、エポキシ基を末端基とするウレトジオン基含有重付加化合物とヒドロキシ基含有ポリマーとからの組成物のポリウレタン−粉体塗料組成物のための使用、被覆組成物および金属被覆 |
US20070282089A1 (en) * | 2004-03-06 | 2007-12-06 | Degussa Ag | Method for producing solid highly-reactive polyurethane compositions containing uretdione groups |
JP2007530757A (ja) * | 2004-04-02 | 2007-11-01 | バイエル・マテリアルサイエンス・アクチェンゲゼルシャフト | 分離産物を含まない、低焼付温度を有するポリウレタン粉末被覆剤 |
US20050239992A1 (en) * | 2004-04-27 | 2005-10-27 | Degussa Ag | Polyurethane composition which contains an uretdione group |
WO2005105879A1 (de) * | 2004-04-27 | 2005-11-10 | Degussa Ag | Uretdiongruppenhaltige polyurethanzusammensetzungen, welche bei niedriger temperatur härtbar sind und (teil-)kristalline harze enthalten |
WO2006040225A1 (de) * | 2004-10-07 | 2006-04-20 | Degussa Ag | Hoch reaktive uretdiongruppenhaltige polyurethanzusammensetzungen |
DE102006004077A1 (de) * | 2006-01-28 | 2007-08-02 | Degussa Gmbh | Verfahren zur Herstellung von hoch reaktiven uretdiongruppenhaltigen Polyurethanverbindungen |
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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 |
EP2238193A1 (de) | 2010-10-13 |
KR20100115750A (ko) | 2010-10-28 |
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