TWI469999B - 製備含有異氰酸酯二聚體(uretdione)基團之高反應性聚胺甲酸酯組成物之乾混合法 - Google Patents
製備含有異氰酸酯二聚體(uretdione)基團之高反應性聚胺甲酸酯組成物之乾混合法 Download PDFInfo
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- TWI469999B TWI469999B TW98103014A TW98103014A TWI469999B TW I469999 B TWI469999 B TW I469999B TW 98103014 A TW98103014 A TW 98103014A TW 98103014 A TW98103014 A TW 98103014A TW I469999 B TWI469999 B TW I469999B
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- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
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- 229920006324 polyoxymethylene Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 239000005077 polysulfide Substances 0.000 description 1
- 229920001021 polysulfide Polymers 0.000 description 1
- 150000008117 polysulfides Polymers 0.000 description 1
- 229920006295 polythiol Polymers 0.000 description 1
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 1
- 229920001289 polyvinyl ether Polymers 0.000 description 1
- 238000010944 pre-mature reactiony 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
- ZEKIXPPWVVMOMQ-UHFFFAOYSA-M propanoate;tetraethylazanium Chemical compound CCC([O-])=O.CC[N+](CC)(CC)CC ZEKIXPPWVVMOMQ-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
- FOWDZVNRQHPXDO-UHFFFAOYSA-N propyl hydrogen carbonate Chemical compound CCCOC(O)=O FOWDZVNRQHPXDO-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
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- 208000024794 sputum Diseases 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance 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
- GFZMLBWMGBLIDI-UHFFFAOYSA-M tetrabutylphosphanium;acetate Chemical compound CC([O-])=O.CCCC[P+](CCCC)(CCCC)CCCC GFZMLBWMGBLIDI-UHFFFAOYSA-M 0.000 description 1
- HLZKNKRTKFSKGZ-UHFFFAOYSA-N tetradecan-1-ol Chemical compound CCCCCCCCCCCCCCO HLZKNKRTKFSKGZ-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
- 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
- YNOWBNNLZSSIHM-UHFFFAOYSA-N tris(oxiran-2-ylmethyl) benzene-1,2,4-tricarboxylate Chemical compound C=1C=C(C(=O)OCC2OC2)C(C(=O)OCC2OC2)=CC=1C(=O)OCC1CO1 YNOWBNNLZSSIHM-UHFFFAOYSA-N 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc 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)
Description
本發明關於一種可在低溫下固化之含有異氰酸酯二聚體基團的聚胺甲酸酯組成物,更特定地關於聚胺甲酸酯粉末塗覆組成物及黏著劑組成物,本發明也關於製備彼等之方法及其用途。
外部或內部封端之異氰酸在室溫下為固體,其在可熱交聯之聚胺甲酸酯(PU)粉末塗料及黏著劑組成物中係頗有價值的交聯劑。
舉例之,德國專利DE-A 27 35 497號揭示具有顯著耐候安定性及熱安定性之PU粉末塗料。製法揭示於德國專利DE-A 27 12 931號之交聯劑係由含有異氰酸酯基團之經ε-己内醯胺-封端的異佛樂酮二異氰酸酯所組成。同時也知悉的是含有胺甲酸乙酯、縮二脲或尿素基團之聚異氰酸酯,彼等之異氰酸酯基團也同樣被封端。
這些外部封端之系統的缺點在於熱交聯反應期間封端劑的消去。因該封端劑可能釋出到環境中,在生態及工作場所的安全基礎上必須特別設法潔淨流出的空氣並回收該封端劑。此外,這些交聯劑屬低反應性,需要高於170℃之固化溫度。
德國專利DE-A 30 30 539號及DE-A 30 30 572號揭示加成聚合之化合物的製法,該等化合物含有異氰酸酯二聚體基團且末端之異氰酸酯基團係用一元醇或一元胺以不可逆方式封端。特別的缺點係該等交聯劑的鏈終止組份,其將導致PU粉末塗層內的低網絡密度,並因此減輕耐溶劑性。
含有異氰酸酯二聚體基團之以羥基為末端之加成聚合化合物係為歐洲專利EP 669 353號之標的。由於彼等的兩個官能度,使其展現增進之耐溶劑性。以這些含有異氰酸酯二聚體基團之聚異氰酸酯為基礎的粉末塗覆組成物共有的特徵為,固化期間彼等不會釋出任何揮發性化合物。然而,烘烤溫度係在較高溫度,亦即在至少180℃。
在PU粉末塗覆組成物中使用脒作為觸媒係揭示於歐洲專利EP 803 524號。雖然這些觸媒確實會使固化溫度減低,但彼等卻呈現相當可觀的黃化,而這對塗層部份通常是有害的。黃化原因推測是脒中反應性氮原子所致。這些氮原子能與大氣的氧反應而形成N-氧化物,是造成變色的原因。歐洲專利EP 803 524號也提及已用在此目的之其他觸媒,但並沒有顯示對固化溫度的任何影響。此類觸媒包括聚胺甲酸酯化學中已知的有機金屬觸媒,如二月桂酸二丁錫(DBTL),或其他之三級胺類,如1,4-二氮雜雙環[2.2.2]辛烷(DABCO)。
專利WO 00/34355號主張以金屬乙醯丙酮鹽為基礎之觸媒:如乙醯丙酮鋅。此類觸媒確實能降低含有異氰酸酯二聚體基團之聚胺甲酸酯粉末塗覆組成物的固化溫度,但彼等之反應產物主要為脲基甲酸酯(allophanates)(M. Gedan-Smolka,F. Lehmann,D. Lehmann“New catalysts for the low temperature curing of uretdione powder coatings”International Waterborne
,High solids and Powder Coatings Symposium,New Orleans
,21-23 February 2001)。脲基甲酸酯係一莫耳醇與二莫耳異氰酸酯的反應產物,而在習知之胺甲酸乙酯化學中係一莫耳醇與一莫耳異氰酸酯反應。由於是形成不需要之脲基甲酸酯,所以破壞了在技術及經濟上有價值之異氰酸酯基團。
某些觸媒會促進異氰酸酯二聚體基團再斷裂至某一程度,當使用含有異氰酸酯二聚體基團之固化劑時,粉末塗料或黏著劑組成物之固化溫度可相當地減低。由於低固化溫度,就會減低儲存安定性。然而,早熟的反應將導致最終特性減低。
乾燥混合物(乾混合物)之製造已眾所周知。然而,因為該等混合物之不均勻性,最終特性的再現性一慣地是不足夠的(Pieter Gillis de Lange in“Powder Coatings Chemistry and Technology”Vincentz Network Hanover,2004,p. 168,p.214)。所以,對顯著改良此不足的再現性的方法存有需求。
因此,本發明之目標係找到一種即使在非常低溫下也可固化且含有異氰酸酯二聚體基團的高反應性聚胺甲酸酯組成物,此外,該等聚胺甲酸酯組成物展現與眾不同的儲存安定性,且更特別適於塑料及高光澤或消光、光穩定性及耐候穩定性粉末塗料及黏著劑的製造。同時,這些組成物應能以再現方式製備。
令人驚訝地頃發現,上文確定之需求的綜合全貌可透過本發明而達成。
因此,本發明首先提供一種具有熔點高於40℃之粉狀組成物,其包含A)至少一種含有異氰酸酯二聚體基團之固化劑,B)至少一種季銨鹽或鏻鹽,C)至少一種環氧化物或乙醯丙酮鹽形式之輔觸媒,D)至少一種單體、寡聚物或聚合物型之一元醇或多元醇,若需要時,E)至少一種單體或聚合物形式之酸,及若需要時,F)輔助劑及添加劑及/或另外之觸媒。
本發明之組成物具有高反應性,及另外地還有儲存安定性之優點。此乃表示本發明之組成物的NCO含量在室溫下儲存四週後減少不多於25%。
較佳地,固化劑A)係以芳族、脂族、(環)脂族及/或脂環族(cycloaliphatic)之聚異氰酸酯及含羥基的化合物為基礎,其中游離NCO含量小於5重量%且異氰酸酯二聚體基團含量為1至25重量%(以C2
N2
O2
計算,分子量84)。
含有異氰酸酯二聚體基團之聚異氰酸酯已為人所熟知,舉例之,係揭示於美國專利4,476,054號、4,912,210號、4,929,724號及歐洲專利0 417 603號。使異氰酸酯二聚合為異氰酸酯二聚體之工業上相關製程的全面性概述係由J. Prakt. Chem. 336(1994)185-200提供。通常使異氰酸酯轉化為異氰酸酯二聚體係在可溶性二聚合觸媒存在下發生,例如二烷胺基吡啶、三烷基膦、三胺化磷或咪唑。此反應可隨意地在溶劑中進行,但以沒有溶劑為較佳,當所欲之轉化率達成時可藉由添加觸媒毒而停止反應。過量的單體異氰酸酯在短路徑蒸發作用之後可被分離。若觸媒具充分揮發性,在單體分離的同時反應混合物就可釋出觸媒。在此情況中不需要加入觸媒毒。原則上,寬廣範圍的異氰酸酯適用於製備含有異氰酸酯二聚體基團之聚異氰酸酯。根據本發明較佳地係使用異佛樂酮二異氰酸酯(IPDI)、六亞甲基二異氰酸酯(HDI)、2-甲基戊烷二異氰酸酯(MPDI)、二異氰酸基環己基甲烷(H12
MDI)、2,2,4-三甲基六亞甲基二異氰酸酯/2,4,4-三甲基六亞甲基二異氰酸酯(TMDI)、降冰片烷二異氰酸酯(NBDI)、亞甲基二苯基二異氰酸酯(MDI)、苯甲胺二異氰酸酯(TDI)及四甲基亞二甲苯基二異氰酸酯(TMXDI)。極佳地係使用IPDI及HDI。
這些帶有異氰酸酯二聚體基團之異氰酸酯轉化為含有異氰酸酯二聚體基團的固化劑A)牽涉到游離NCO基團與作為鏈伸長劑之含羥基單體或聚合物的反應,該等含羥基單體或聚合物諸如聚酯類、聚硫醚類、聚醚類、聚己內醯胺類、聚環氧化物、聚酯醯胺類、聚胺甲酸酯或低分子量二-、三-及/或四-醇類,若需要時,一元胺及/或一元醇可作為鏈終止劑,此一轉化作用已經常被揭示(專利EP 669 353號、EP 669 354號、DE 30 30 572號、EP 639 598號或EP 803 524號)。而以聚酯類及單體型二元醇較佳。除了異氰酸酯二聚體基團,該等固化劑也可含有異氰酸酯、縮二脲、脲基甲酸酯、胺甲酸乙酯及/或尿素結構。
固化劑之實例包括VESTAGON BF 9030、VESTAGON BF 1320及VESTAGON 1540(所有都屬於Evonik Degussa GmbH公司)及Crelan EF 403(Bayer AG公司)。特別佳的是VESTAGON BF 9030及VESTAGON BF 1320。
更特別地,組份A之比例以全部組成物計為5-99重量%,以10-80%重量較佳,20-50%重量更佳。
特定為組份B)之季銨鹽或鏻鹽係充當為觸媒。因此,觸媒B)較佳地為具有鹵素或有機或無機酸陰離子為抗衡離子之四烷基銨鹽或鏻鹽。適當觸媒之實例為甲酸四甲銨、乙酸四甲銨、丙酸四甲銨、丁酸四甲銨、苯甲酸四甲銨、甲酸四乙銨、乙酸四乙銨、丙酸四乙銨、丁酸四乙銨、苯甲酸四乙銨、甲酸四丙銨、乙酸四丙銨、丙酸四丙銨、丁酸四丙銨、苯甲酸四丙銨、甲酸四丁銨、乙酸四丁銨、丙酸四丁銨、丁酸四丁銨及苯甲酸四丁銨,以及乙酸四丁基鏻、甲酸四丁基鏻及乙酸乙基三苯基鏻、苯並三唑化四丁基鏻、苯酚化四苯基鏻及癸酸三己基十四烷基鏻、氟化四甲銨、氟化四乙銨、氟化四丁銨、氟化四辛銨、氟化苄基三甲銨、氫氧化四丁基鏻、氟化四丁基鏻、氯化四丁銨、溴化四丁銨、碘化四丁銨、氯化四乙銨、溴化四乙銨、碘化四乙銨、氯化四甲銨、溴化四甲銨、碘化四甲銨、氯化苄基三甲銨、氯化苄基三乙銨、氯化苄基三丙銨、氯化苄基三丁銨、氯化甲基三丁銨、氯化甲基三丙銨、氯化甲基三乙銨、氯化甲基三苯銨、氯化苯基三甲銨、溴化苄基三甲銨、溴化苄基三乙銨、溴化苄基三丙銨、溴化苄基三丁銨、溴化甲基三丁銨、溴化甲基三丙銨、溴化甲基三乙銨、溴化甲基三苯銨、溴化苯基三甲銨、碘化苄基三甲銨、碘化苄基三乙銨、碘化苄基三丙銨、碘化苄基三丁銨、碘化甲基三丁銨、碘化甲基三丙銨、碘化甲基三乙銨、碘化甲基三苯銨及碘化苯基三甲銨,氟化四甲銨、氟化四乙銨、氟化四丁銨、氟化四辛銨及氟化苄基三甲銨。這些觸媒可單獨或以混合物方式添加。彼等也可被包封或以聚合方式附接。該等觸媒可含有結晶化的水,在計算所用之觸媒量時該水是不算在內;換句話說,水量需扣除。
在本發明之另一具體實施例中,前述之觸媒也可應用成為固體載體,如二氧化矽。此舉將使可磨性增加,同時也較易於加工處理。基於此目的,觸媒係溶解於適當的惰性溶劑(如水)及對應數量的適當固體載體中,該數量通常和所添加之觸媒正好相同,載體之實例可為Sipernat 2200(取自Evonik Degussa GmbH公司之二氧化矽)。也適當的載體係其他沉澱或烟燻型二氧化矽。舉例之,這些可分別購自Evonik Degussa GmbH公司之商品名SipernatTM
或AEROSILTM
。接著在溶劑中混合,並除去溶劑。為了此一目的,可適度地藉由適於分離溶劑之所有技術性裝置來處理,例如乾燥箱、蒸餾裝置或其他噴霧乾燥器。所得之產物變得容易處理,不再容易黏住,並更加易於充分的研磨及篩分。
在本發明之組成物中觸媒B)的比例以全部組成物計較佳地為0.1至5重量%,以0.3至3重量%更佳。特別佳的是使用苯甲酸四乙銨及氫氧化四丁銨作為觸媒B)。
在C)下之適當輔觸媒為環氧化物或乙醯丙酮鹽。環氧化物組群之實例包括縮水甘油醚類及酯類、脂族環氧化物、以雙酚A為基礎之二縮水甘油醚類、及甲基丙烯酸縮水甘油酯。此類環氧化物之實例有異氰尿酸三縮水甘油基(TGIC,商品名Araldit 810,Huntsman公司)、對苯二甲酸二縮水甘油酯與偏苯三甲酸三縮水甘油酯之混合物(商品名Araldit PT 910及912,Huntsman公司)、叔碳酸(versatic acid)縮水甘油酯(商品名Kardura E10,Shell公司)、3’,4’-環氧基環己烷甲酸3,4-環氧基環己基甲酯(ECC),以雙酚A為基礎之二縮水甘油醚(商品名EPIKOTE 828,Shell公司)、乙基己基縮水甘油醚、丁基縮水甘油醚、季戊四醇四縮水甘油醚(商品名Polypox R16,UPPC AG公司)及其他具有游離環氧基之Polypox產品。此外,也適當的有單一或聚異氰酸酯及縮水甘油醇之反應產物。
另外適當之輔觸媒包括金屬乙醯丙酮鹽,實例有乙醯丙酮鋰或乙醯丙酮鋅。
較佳地,該輔觸媒為Araldit PT 910及Araldit PT 912。當然,也可行的是使用上述輔觸媒之混合物作為組份C)。作為組份C)之輔觸媒的比例以全部組成物計更特別地為0.1至5重量%,以0.3至3重量%較佳。
本發明的方案之一包括上述觸媒B)或輔觸媒C)的聚合物型附接。舉例之,觸媒B)或輔觸媒C)可以化學方式附接到固化劑A)或醇D)中。基於此目的,輔觸媒C)之環氧化物基團可與羥基聚酯D)之酸基團反應。或者,氫氧化四烷基銨B)可與羥基聚酯D)之酸基團反應而生成鹽。
觸媒或輔觸媒二者可額外地被殼層環繞,並因此被包封。舉例之,微包封之實例可於“Microencapsulation and Particle Coating”Center for Professional Advancement(conference proceedngs),Amsterdam 2005中查到。特別適當之殼層物質包括聚合物,實例有聚酯類、聚烯烴、聚丙烯酸酯類、聚醚類、聚胺甲酸酯類、聚碳酸酯類、聚乙烯基醚類及在所述文獻中特定之其他聚合物。
此外,關於基本組份D),本發明之組成物含有單體、寡聚物或聚合物型之一元醇或多元醇。在反應條件下,這些醇類與固化劑之官能基團(異氰酸酯二聚體)反應並發生交聯。特別適當之單體醇類為具有分子量至少32公克/莫耳之一-、二-或多元醇。
舉例之,一元醇為甲醇、乙醇、正-丙醇、異丙醇、正-丁醇、異丁醇、第二-丁醇、異構的戊醇類、己醇類、辛醇類及壬醇類、正-癸醇、正-十二烷醇、正-十四烷醇、正-十六烷醇、正-十八烷醇、環己醇、異構的甲基環己醇類及羥甲基環己烷。
舉例之,二元醇為乙二醇、三乙二醇、丁烷-1,4-二醇、戊烷-1,5-二醇、己烷-1,6-二醇、3-甲基戊烷-1,5-二醇、新戊基二醇、2,2,4(2,4,4)-三甲基己二醇及羥基三甲基乙酸新戊基二醇酯。
舉例之,三元醇為三羥甲基丙烷、二一三羥甲基丙烷、三羥甲基乙烷、己烷-1,2,6-三醇、丁烷-1,2,4-三醇、三(β-羥乙基)-異氰尿酸酯、季戊四醇、甘露醇或山梨醇。
在寡聚物或聚合物型醇之組群中,較佳地係使用具有OH數為5至500(單位為毫克KOH/公克)之聚酯類、聚醚類、聚丙烯酸酯類、聚胺甲酸酯類及/或聚碳酸酯類。
更特別地係使用自羧酸與較佳地多元醇所合成之聚酯類作為組份D)。較佳地用於製備這些聚酯之羧酸類本質上可為脂族、脂環族、芳族及/或雜環系者,若需要也可為不飽和及/或經鹵素原子取代者。可提及之實例包括下述:丁二酸、己二酸、辛二酸、十二烷二酸、十四烷二酸、壬二酸、癸二酸、苯二甲酸、對苯二甲酸、異苯二甲酸、偏苯三甲酸、均苯四甲酸、四氫苯二甲酸、六氫苯二甲酸、六氫對苯二甲酸、二-及四氯基苯二甲酸、內亞甲基四氫苯二甲酸、戊二酸、順丁烯二酸及反丁烯二酸(及可取得的話,彼等之酐類)、對苯二甲酸二甲酯、對苯二甲酸雙乙二醇酯,以及環狀一元羧酸如苯甲酸、對-第三-丁基苯甲酸或六氫苯甲酸。
適當於製備聚酯D)之多元醇的實例包括乙二醇、1,2-及1,3-丙二醇、1,4-及2,3-丁二醇、二-β-羥乙基丁二醇、1,6-己二醇、1,8-辛二醇、新戊二醇、環己二醇、1,4-雙(羥甲基)丙烷、2-甲基丙烷-1,3-二醇、2-甲基戊烷-1,5-二醇、2,2,4(2,4,4)-三甲基己烷-1,6-二醇、丙三醇、三羥甲基丙烷、三羥甲基乙烷、己烷-1,2,6-三醇、丁烷-1,2,4-三醇、三(β-羥乙基)異氰酸酯、季戊四醇、甘露醇及山梨醇,也可為二乙二醇、三乙二醇、四乙二醇、二丙二醇、聚丙二醇、聚丁二醇、苯二甲醇及羥基三甲基乙酸新戊二醇酯。
此外,内酯類之單酯及聚酯如ε-己内酯、或羥基羧酸類如羥基三甲基乙酸、ε-羥基癸酸、ε-羥基己酸、硫代乙醇酸也可用作為製備聚合物D)之起始物質。
再者,上述之多元羧酸及/或其衍生物與聚苯酚(如對苯二酚、雙酚A、4,4’-二羥基聯苯或雙(4-羥苯基)碸)之聚酯類、或碳酸之聚酯類也適用,該碳酸之聚酯類係自對苯二酚、二羥苯基丙烷、對-苯二甲醇、乙二醇、丁二醇或己烷-1,6-二醇、及其他多元醇藉由典型縮合反應(例如與光氣或碳酸二乙酯及/或二苯酯之反應)而獲得,或藉由已知方式之聚合反應自環狀碳酸酯如碳酸乙二醇酯或碳酸亞乙烯基酯中獲得。如眾所周知,含有碳酸基團之範例性聚合物D)可藉由使分子量範圍為62至300公克/莫耳之範例性二元或三元醇與碳酸二芳酯(如碳酸二苯酯)、光氣,或較佳地環狀碳酸酯(如碳酸伸丙酯或碳酸2,2-二甲基伸丙酯(NPC))或此類環狀碳酸酯之混合物反應而獲得。特別佳之碳酸二醇酯係從那些以所述之二元為起始分子並使NPC的開環的反應而製備。
同樣地也適用作為製備聚合物D)之起始物質有矽酸之聚酯類、磷酸之聚酯類(例如來自甲烷-、乙烷-、β-氯乙烷-、苯-或苯乙烯-磷酸、-磷醯氯或-磷酸酯與上述種類之多元醇及多酚)、硼酸之聚酯類、聚矽氧烷,如藉由使二烷基二氯基矽烷與水進行水解及隨後以多元醇處理而獲得之產物,及藉由使聚矽氧烷二氫化物與烯烴(如烯丙醇或丙烯酸)進行加成反應而獲得之產物。
可用作為組份D)之可能的聚酯之其他實例為多元羧酸與縮水甘油基化合物之反應產物,例如專利DE-A 24 10 513號所揭示者。
可使用之縮水甘油基化合物的實例為2,3-環氧基-1-丙醇與具有4至18個碳原子之一元酸類的酯類(諸如有棕櫚酸縮水甘油酯、月桂酸縮水甘油酯及硬脂酸縮水甘油酯)、具有4至18個碳原子之環氧烷(如環氧丁烷),以及縮水甘油基醚類(如辛基縮水甘油基醚)。
上述之聚酯類可依習知方式藉由在100至270℃下(以130至230℃較佳)及惰性氣體氣氛下以熔融或共沸程序進行縮合作用而獲得,舉例之,其係說明於Methoden der Organischen Chemie(Houben-Weyl);volume 14/2,pages 1 to 5,21 to 23,40 to 44,Georg Thieme Verlag,Stuttgart,1963,或說明於C.R. Martens,Alkyd Resins,pages 51 to 59,Reinhold Plastics Appl. Series,Reinhold Publishing Comp.,New York 1961。
適當之聚合物D)進一步包括羥基-官能基聚醚類及聚碳酸酯類。舉例之,較佳之聚醚類可藉由使環氧化物如環氧乙烷、環氧丙烷、環氧丁烷、氧雜環丁烷、3,3-雙(氯甲基)氧雜二環丁烷、四氫呋喃、氧化苯乙烯或二羥苯基丙烷之2,5-雙-環氧基丙基醚進行加成聚合而製備;或藉由在路易士酸如三氟化硼存在下進行陽離子性聚合反應而製備;或藉由與鹼金屬氫氧化物或鹼金屬醇鹽進行陰離子性聚合反應而製備;或藉由適當地在混合物中或連續地使這些環氧化物與含有反應性氫原子之起始組份進行加成反應而製備,這些含有反應性氫原子之起始組份諸如醇類或胺類,也可為水、乙二醇、聚1,3-或1,2-、1,3-或1,2-二醇、戊二醇、己二醇、十二烷基二醇、三羥甲基丙烷、丙三醇、苯胺、氨、乙醇胺、乙二胺、二(β-羥丙基)甲胺、及羥烷基化酚類如二(β-羥乙氧基)間苯二酚。
此外,也適用作為聚合物D)者有聚胺甲酸酯化學中已知且含有對異氰酸基團呈反應性之羥基之分子量範圍在250至8500公克/莫耳之聚硫醚類、聚縮醛類、聚環氧化物、聚酯醯胺類或聚胺甲酸酯類。
特別佳的是使用具有OH數為15至150且平均分子量為500至8000公克/莫耳之含羥基聚酯類作為組份D)。
當然也可行的是使用上述單體、寡聚物及/或聚合物之混合物。這些聚合物可為無定形或部份結晶。組份D)之比例以全部組成物計更特別地介於1與95重量%之間,以2至50重量%較佳。
本發明之組成物可進一步包含至少一種單體或聚合物形式之酸(組份E)。適用於本發明目的之酸類包括所有具有布忍斯特(Broenstedt)或路易士酸特性之固體或液體、有機或無機、單體或聚合物型化合物。可提及之實例包括下述:硫酸、乙酸、苯甲酸、丙二酸、對苯二甲酸、及具有酸值至少20之共聚酯或共聚醯胺。若存在時,該等酸之比例以全部組成物計更特別地為0.1至10重量%。
本發明之組成物可進一步包含常用於塗料或黏著劑技術之輔助劑及添加劑,及/或另外之觸媒作為組份F)。此類輔助劑及添加劑之實例為流動控制劑如聚矽氧烷或丙烯酸酯、光穩定劑如空間性位阻胺、或其他輔助劑如專利EP 669 353號所揭示者。而且,也可行的是以填充劑及顏料作為輔助劑,例如二氧化鈦,舉例之,其存在量以全部組成物計為至高50重量%。若存在時,所述之輔助劑及添加劑的比例以全部組成物計更特別地為0.001至55重量%。
隨意地,在聚胺甲酸酯化學中已知種類之額外觸媒也可存在。這些主要為有機金屬觸媒,諸如二月桂酸二丁錫、或其他之三級胺如1,4-二氮雜二環[2.2.2]辛烷,其量更特別地為0.001至1重量%。
同樣地本發明係提供一種用於製備本發明之粉狀組成物的方法,其包含乾混合個別組份A)至F),或乾混合個別組份A)至F)之均勻混合物,其先決條件是組份B)及C)並不存在於該相同之均勻混合物中。
所以,本發明之方法係以乾混合本發明之組成物的個別組份或個別組份之混合物為基礎。本發明之乾混合物係一所有組份完全熔融或所有組份並沒有完全溶解的混合物。結果,此類乾混合物並沒有完全均勻。乾燥混合之操作可在任何熟諳此藝者已知且適於此目的之混合器中進行。更特別地,討論中之混合器包含所有種類的攪拌桶(如混合器)、搖動型混合器(如Turbular)及其他能在室溫下混合粉狀組成物之組合件。
在最簡單的情況下使個別組份乾混合,換句話說在沒有溶劑下混合,以製備本發明之粉狀組成物。在本發明方法之選擇性具體實施例中,係使該組成物之個別組份的均勻混合物互相乾混合。但在該方法的變異情況下,組份B)及C)必須不存在於相同之均勻混合物中,使得以避免不想要的初步反應。均勻混合物係一於溶劑或熔融體中之混合物。為了製造組份混合物,各組份之均勻化可於適當組合裝置(例如可加熱攪拌桶、揉合設備或其他擠壓機)中進行,且不超過溫度上限120℃至130℃。較佳地是組份A)及D)一起用於一均勻混合物。較佳的是組份C)加入此A)及D)之均勻混合物中。其後,各別地或一起地研磨該等組份或組份混合物,並篩分。篩分之最大粒度為200微米,以100微米較佳。隨後,在適當之混合設備(如Turbular)中小心地使所有已研磨及篩分之組份互相乾燥混合。若需要時,此混合物可在剛好低於熔點的高溫下於額外步驟中再次地燒結在一起,然後依次地研磨及篩分至所欲之大小。
同樣地,本發明提供含有本發明之組成物的黏著劑組成物,及本發明之組成物於金屬、塑料、玻璃、木材、紡織品、紙或皮革基材、纖維複合材料或其他耐熱性基材上產生黏著性結合的用途。
同樣地,本發明提供含有本發明之組成物的粉末塗覆材料,及本發明之組成物在金屬、塑料、玻璃、木材或皮革基材或其他耐熱性基材上產生表面塗層之用途。
同樣地,本發明提供含有本發明之組成物的金屬-塗覆組成物(更特別地其係用於車體、摩托車及腳踏車、建築組件及家用電器)、木材-塗覆組成物、玻璃-塗覆組成物、皮革-塗覆組成物或塑料-塗覆組成物。
在本發明用途之內文中,本發明之組成物係以適當方式施加在基材上,例如藉由噴霧、流化床燒結或散射。將現成可噴霧之粉末施加在適當基材係根據已知之方法而進行,例如藉由靜電粉末噴霧、流化床燒結、或靜電流化床燒結。在黏著性結合之情況中,該粉末係施加在那些欲接合的基材上,然後互相施壓。施加後,藉由在60至220℃下加熱1至60分鐘使該等受塗覆之工件固化,以在80至160℃達6至30分鐘為較佳。
縱使沒有進一步談論,可假定的是熟諳此藝者應能寬廣地利用上述之說明。因此,較佳之具體實施例及實施例僅只是以敘述性說明來解釋,無論如何這些敘述性說明都不具限制性結果。本發明將利用實施例並於下文中解說。本發明之選擇性具體實施例可用類推的方法獲得。
OH數係根據DIN 53240-2測量。經由此方法,在4-二甲胺基吡啶觸媒存在下使試樣與乙酐反應,以使羥基團乙醯化。此舉產生每一羥基有一分子之乙酸,然而過量之乙酐在隨後的水解作用中產生兩分子的乙酸。乙酸之消耗係藉由滴定分析來測量平行操作之主要數值及空白試驗值間之差異而得。
NCO值係經由添加二丁胺以濕式化學方式測量,隨後靠著溴酚藍的指示使用鹽酸來滴定過量之二丁胺。所用之溶劑可為異丙醇與水的混合物。
異氰酸酯二聚體含量係經由添加丁胺以濕式化學方式測量,隨後靠著溴酚藍的指示使用鹽酸滴定過量之丁胺。所用之溶劑可為異丙醇與水的混合物。
在120℃(恆溫器設定)下將61.65公克之DYNACOLL 7330(組份D)放入鋼鍋中並攪拌約1小時使之熔融。隨後,在相同溫度下以一份方式加入35.35公克之VESTAGON BF 9030(組份A)並持續攪拌約1.5-2小時。其後,加入1公克之Araldit PT 910(組份C)並攪拌15分鐘以上。當均勻之熔融物出現時,就可分配產物。在家用攪碎機(Braun,型號4142)中使冷卻之熔融物進行初步的切碎,隨後研磨。研磨操作係在一經由液態氮協助之快速轉子研磨機(Fritsch,Pulverisette 14)中進行。N2
冷卻可防止產物在研磨機中黏著。其後,已變得潮濕之產物必須在真空乾燥櫥(50毫巴)中及室溫下乾燥。當產物乾燥(以視覺上沒有流動性來評估)後,將之放在分析性篩分機(Restch,型號AS200基本型)中並篩分至粒度<63微米。
將50公克TEAB(組份B)和150毫升完全去離子水一起放入500毫升圓底瓶中,在超過5分鐘期間此最初之進料便在室溫下溶解。其後,加入50公克Sipernat 2200(載體)並在50℃及約6毫巴下於旋轉蒸發器內進行濃縮。在混合器中分割此極大的乾燥產物,隨後在50℃之真空乾燥櫥(50毫巴)中乾燥至質量不變。隨後使之研磨並篩分至粒度<63微米。
稱重98公克己均勻化且粉碎之A)、C)及D)的均勻混合物(實施例1a),並和2公克步驟b)之混合物一起放入1公升Turbula塑膠容器中,在46rpm之搖動型混合器(Bachhofen AG,Turbula型式,Schatz system)中混合30分鐘。其後,將該混合物分佈於金屬乾燥板上並在80℃下部份燒結約15-20分鐘。之後,再次研磨並篩分至粒度為100-200微米。此舉可獲得具有熔點約90℃且NCO含量為4.40%(理論值:4.37%)之粉末。縱使在室溫下4週之久,NCO值實質上還維持不變(4.20%),其可證明本發明之混合物的儲存穩定性。
在120℃(恆溫器設定)下將61.65公克之DYNACOLL 7330放入鋼鍋中並攪拌約1小時使之熔融。隨後,在相同溫度下加入35.35公克之VESTAGON BF 9030、1公克PT 910及2公克TEAB及Sipernat之混合物。
d1) 在超過15分鐘期間並在此溫度下使該混合物進行凝膠化。
d2) 若在10分鐘內將溫度降低至室溫,接著加入最後組份,研磨並篩分至100-200微米後,其結果是獲得具有NCO含量2.60%(理論值:4.37%)之粉末。在室溫下4週後,NCO值降至1.90%,且該粉末不再能完全溶解。
自綿織物中裁切兩塊已量好110公釐×110公釐之布。將該粉狀組成物散塗在一塊棉布的下半區,藉助於一具有網目尺寸小於160微米之篩網在110公釐×50公釐的面積處進行黏合。施加之重量約為30公克/平方公尺。在比該粉末之熔點高10℃的溫度下於熱空氣烤箱中使織物表面上之粉末燒結5分鐘。
冷卻後,並於140℃溫度之壓機中在10巴壓力下使該具有初步塗覆之黏著劑的棉布與未塗覆之布層合達10分鐘。一天後,從該織物結合物中裁切己量好15公釐寬110公釐長之試驗用布條,黏合長度為50公釐。丟棄兩塊外部的布條。
關於剝離強度之試驗,將未黏合之織物布條的末端固定在拉力試驗機之夾具的頂部及底部,並根據DIN EN 28510在180°角度下以50公釐/分鐘之速度分離。報告之數字係以5次測量之平均值作為最大值力Fmax,單位為N。大於4N之力Fmax,黏合劑結合便視為良好。
用於本發明之組成物1c)的紡織品黏合產生良好的黏著力,具有6.9N之Fmax值。非本發明之組成物1 d2)不再能熔融,所以不能用為黏合劑結合。
Claims (20)
- 一種製備具有熔點大於40℃之粉狀組成物的方法,其中該粉狀組成物包含A)至少一種含有異氰酸酯二聚體(uretdione)基團之固化劑,B)至少一種季銨鹽或鏻鹽,C)至少一種環氧化物或乙醯丙酮鹽形式之輔觸媒,D)至少一種單體、寡聚物或聚合物型之一元醇或多元醇,若需要時,E)至少一種單體或聚合物形式之酸,及若需要時,F)輔助劑及添加劑及/或另外之觸媒,該方法包含乾混合個別組份A)至F),或乾混合個別組份A)至F)之均勻混合物,其先決條件是組份B)與C)不存在於相同的均勻混合物中。
- 如申請專利範圍第1項之方法,其中該固化劑A)係以具有游離NCO含量小於5重量%且異氰酸酯二聚體基團含量為1至25重量%之芳族、脂族、(環)脂族及/或脂環族(cycloaliphatic)的聚異氰酸酯及含羥基化合物為基礎。
- 如申請專利範圍第1或2項之方法,其中A)之比例以全部組成物計為5-99重量%。
- 如申請專利範圍第1項之方法,其中B)包含帶有鹵素或有機或無機酸陰離子作為抗衡離子之四烷基銨鹽或鏻鹽。
- 如申請專利範圍第4項之方法,其中B)之比例以全部組成物計為0.1至5重量%。
- 如申請專利範圍第4項之方法,其中使用苯甲酸 四乙銨及氫氧化四丁銨作為B)。
- 如申請專利範圍第1項之方法,其中C)之比例以全部組成物計為0.1至5重量%。
- 如申請專利範圍第1項之方法,其中使用聚酯類作為組份D)。
- 如申請專利範圍第8項之方法,其中使用具有OH數為15至150且平均分子量為500至8000公克/莫耳之含羥基聚酯類作為組份D)。
- 如申請專利範圍第8項之方法,其中組份D)之比例以全部組成物計介於1與95重量%之間。
- 如申請專利範圍第1項之方法,其中使用流動控制劑、光穩定劑、填充劑及顏料作為組份F)。
- 一種黏著劑組成物,其包含由如申請專利範圍第1至11項中任一項之方法所製得的粉狀組成物。
- 一種粉末塗覆材料,其包含由如申請專利範圍第1至11項中任一項之方法所製得的粉狀組成物。
- 一種金屬-塗覆組成物,其包含由如申請專利範圍第1至11項中任一項之方法所製得的粉狀組成物。
- 一種木材-塗覆組成物,其包含由如申請專利範圍第1至11項中任一項之方法所製得的粉狀組成物。
- 一種玻璃-塗覆組成物,其包含由如申請專利範圍第1至11項中任一項之方法所製得的粉狀組成物。
- 一種皮革-塗覆組成物,其包含由如申請專利範圍第1至11項中任一項之方法所製得的粉狀組成物。
- 一種塑料-塗覆組成物,其包含由如申請專利範圍第1至11項中任一項之方法所製得的粉狀組成物。
- 一種使用由如申請專利範圍第1至11項中任一項之方法所製得的粉狀組成物於金屬、塑料、玻璃、木材、紡織品、紙或皮革基材或纖維複合材料上產生黏著性結合的用途。
- 一種使用由如申請專利範圍第1至11項中任一項之方法所製得的粉狀組成物在金屬、塑料、玻璃、木材或皮革基材上產生表面塗層之用途。
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
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DE102008007386A DE102008007386A1 (de) | 2008-02-01 | 2008-02-01 | Verfahren zur Herstellung hochreaktiver uretdiongruppenhaltiger Polyurethanzusammensetzungen im Dryblend |
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TW200948841A TW200948841A (en) | 2009-12-01 |
TWI469999B true TWI469999B (zh) | 2015-01-21 |
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TW98103014A TWI469999B (zh) | 2008-02-01 | 2009-01-23 | 製備含有異氰酸酯二聚體(uretdione)基團之高反應性聚胺甲酸酯組成物之乾混合法 |
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US (1) | US8702899B2 (zh) |
EP (1) | EP2238193A1 (zh) |
JP (1) | JP6108652B2 (zh) |
KR (1) | KR20100115750A (zh) |
CN (1) | CN101497686B (zh) |
CA (1) | CA2713399A1 (zh) |
DE (1) | DE102008007386A1 (zh) |
TW (1) | TWI469999B (zh) |
WO (1) | WO2009095117A1 (zh) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
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US11939426B2 (en) | 2020-10-16 | 2024-03-26 | Tosoh Corporation | Polycarbonate polyol and method for producing same, composition and method for producing same, urethane resin and aqueous urethane resin dispersion |
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Publication number | Priority date | Publication date | Assignee | Title |
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DE102007062316A1 (de) * | 2007-12-21 | 2009-06-25 | Evonik Degussa Gmbh | Reaktive Isocyanatzusammensetzungen |
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US9133377B2 (en) * | 2010-05-20 | 2015-09-15 | A. Raymond Et Cie | Adhesive polyurethane powder capable of being activated by heat |
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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 |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20050090636A1 (en) * | 2003-10-22 | 2005-04-28 | Degussa Ag | High-reactivity polyurethane powder coating compositions based on epoxy-terminated polyaddition compounds containing uretdione groups |
US20050239992A1 (en) * | 2004-04-27 | 2005-10-27 | Degussa Ag | Polyurethane composition which contains an uretdione group |
CN1878810A (zh) * | 2004-04-27 | 2006-12-13 | 德古萨公司 | 含有脲二酮基、能够在低温下固化且包括(部分)结晶树脂的聚氨酯组合物 |
CN1878815A (zh) * | 2004-10-07 | 2006-12-13 | 德古萨公司 | 含脲二酮基的高反应性聚氨酯组合物 |
CN1930205A (zh) * | 2004-03-06 | 2007-03-14 | 德古萨公司 | 用于制备含缩脲二酮基团的固体高反应性聚氨酯组合物的方法 |
Family Cites Families (32)
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 |
DE19856878A1 (de) | 1998-12-10 | 2000-06-15 | Inst Polymerforschung Dresden | Härtbare uretdiongruppenhaltige Massen und ein Verfahren zu ihrer Herstellung und Verarbeitung sowie ihre Verwendung |
DE10205608A1 (de) * | 2002-02-11 | 2003-08-21 | Degussa | Bei niedriger Temperatur härtbare feste uretdiongruppenhaltige Polyurethan-Pulverlackzusammensetzungen |
DE10320267A1 (de) * | 2003-05-03 | 2004-11-18 | Degussa Ag | Bei niedriger Temperatur härtbare feste uretdiongruppenhaltige Polyurethan-Pulverlackzusammensetzungen |
DE10320266A1 (de) * | 2003-05-03 | 2004-11-18 | Degussa Ag | Feste Uretdiongruppenhaltige Polyurethan-Pulverlackzusammensetzungen bei niedriger Temperatur härtbar |
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 |
DE10347901A1 (de) | 2003-10-15 | 2005-05-19 | Degussa Ag | Polyurethan-Pulverlackbeschichtungen, welche feste uretdiongruppenhaltige Polyadditionsverbindungen enthalten, und ein Verfahren zu ihrer Herstellung |
DE102004011005A1 (de) | 2004-03-06 | 2005-09-22 | Degussa Ag | Bei niedriger Temperatur härtbare uretdiongruppenhaltige Polyurethanzusammensetzungen |
DE102004017005A1 (de) | 2004-04-02 | 2005-10-20 | Bayer Materialscience Ag | Abspalterfreier Polyurethan-Pulverlack mit niedriger Einbrenntemperatur |
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 |
DE102006004077A1 (de) * | 2006-01-28 | 2007-08-02 | Degussa Gmbh | Verfahren zur Herstellung von hoch reaktiven uretdiongruppenhaltigen Polyurethanverbindungen |
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 (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20050090636A1 (en) * | 2003-10-22 | 2005-04-28 | Degussa Ag | High-reactivity polyurethane powder coating compositions based on epoxy-terminated polyaddition compounds containing uretdione groups |
CN1930205A (zh) * | 2004-03-06 | 2007-03-14 | 德古萨公司 | 用于制备含缩脲二酮基团的固体高反应性聚氨酯组合物的方法 |
US20050239992A1 (en) * | 2004-04-27 | 2005-10-27 | Degussa Ag | Polyurethane composition which contains an uretdione group |
CN1878810A (zh) * | 2004-04-27 | 2006-12-13 | 德古萨公司 | 含有脲二酮基、能够在低温下固化且包括(部分)结晶树脂的聚氨酯组合物 |
CN1878815A (zh) * | 2004-10-07 | 2006-12-13 | 德古萨公司 | 含脲二酮基的高反应性聚氨酯组合物 |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US11939426B2 (en) | 2020-10-16 | 2024-03-26 | Tosoh Corporation | Polycarbonate polyol and method for producing same, composition and method for producing same, urethane resin and aqueous urethane resin dispersion |
Also Published As
Publication number | Publication date |
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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 |
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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