CN1223641C - 可固化涂料组合物 - Google Patents
可固化涂料组合物 Download PDFInfo
- Publication number
- CN1223641C CN1223641C CNB011089040A CN01108904A CN1223641C CN 1223641 C CN1223641 C CN 1223641C CN B011089040 A CNB011089040 A CN B011089040A CN 01108904 A CN01108904 A CN 01108904A CN 1223641 C CN1223641 C CN 1223641C
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- Prior art keywords
- reaction
- acid
- group
- polyester
- amino formic
- Prior art date
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- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical group NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 title claims abstract description 39
- 229920000728 polyester Polymers 0.000 title claims abstract description 34
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 title claims description 5
- 229920000642 polymer Polymers 0.000 title abstract description 7
- 238000006243 chemical reaction Methods 0.000 claims description 66
- 239000002253 acid Substances 0.000 claims description 31
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 27
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 26
- 150000001875 compounds Chemical class 0.000 claims description 21
- 239000000203 mixture Substances 0.000 claims description 19
- 239000008199 coating composition Substances 0.000 claims description 16
- 239000003795 chemical substances by application Substances 0.000 claims description 14
- 229910021529 ammonia Inorganic materials 0.000 claims description 13
- 150000005676 cyclic carbonates Chemical group 0.000 claims description 13
- 125000000524 functional group Chemical group 0.000 claims description 12
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 7
- 239000000908 ammonium hydroxide Substances 0.000 claims description 7
- 239000007795 chemical reaction product Substances 0.000 claims description 3
- 229920005862 polyol Polymers 0.000 abstract description 4
- 150000003077 polyols Chemical class 0.000 abstract description 4
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 22
- 239000002904 solvent Substances 0.000 description 22
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- -1 alkyl carbamate Chemical compound 0.000 description 17
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- 239000000126 substance Substances 0.000 description 9
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- 239000000049 pigment Substances 0.000 description 6
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- 230000002378 acidificating effect Effects 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 5
- 150000008064 anhydrides Chemical group 0.000 description 5
- 229910052799 carbon Inorganic materials 0.000 description 5
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- SVTBMSDMJJWYQN-UHFFFAOYSA-N 2-methylpentane-2,4-diol Chemical compound CC(O)CC(C)(C)O SVTBMSDMJJWYQN-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
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- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 description 4
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- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
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- 238000004132 cross linking Methods 0.000 description 4
- 238000001723 curing Methods 0.000 description 4
- 125000003700 epoxy group Chemical group 0.000 description 4
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 4
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 4
- 238000012423 maintenance Methods 0.000 description 4
- XNLICIUVMPYHGG-UHFFFAOYSA-N pentan-2-one Chemical compound CCCC(C)=O XNLICIUVMPYHGG-UHFFFAOYSA-N 0.000 description 4
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 4
- 229920000058 polyacrylate Polymers 0.000 description 4
- 150000003141 primary amines Chemical class 0.000 description 4
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 229920000877 Melamine resin Polymers 0.000 description 3
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 3
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 3
- 229920001807 Urea-formaldehyde Polymers 0.000 description 3
- 150000008065 acid anhydrides Chemical class 0.000 description 3
- 238000007171 acid catalysis Methods 0.000 description 3
- GZCGUPFRVQAUEE-SLPGGIOYSA-N aldehydo-D-glucose Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O GZCGUPFRVQAUEE-SLPGGIOYSA-N 0.000 description 3
- 229920003232 aliphatic polyester Polymers 0.000 description 3
- 150000001721 carbon Chemical group 0.000 description 3
- 239000001569 carbon dioxide Substances 0.000 description 3
- 229910002092 carbon dioxide Inorganic materials 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 239000002131 composite material Substances 0.000 description 3
- 125000000753 cycloalkyl group Chemical group 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 3
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- 229920005906 polyester polyol Polymers 0.000 description 3
- 239000005056 polyisocyanate Substances 0.000 description 3
- 229920001228 polyisocyanate Polymers 0.000 description 3
- 239000004814 polyurethane Substances 0.000 description 3
- 229920002635 polyurethane Polymers 0.000 description 3
- 150000003839 salts Chemical group 0.000 description 3
- 238000007711 solidification Methods 0.000 description 3
- 230000008023 solidification Effects 0.000 description 3
- 239000002966 varnish Substances 0.000 description 3
- ARXKVVRQIIOZGF-UHFFFAOYSA-N 1,2,4-butanetriol Chemical compound OCCC(O)CO ARXKVVRQIIOZGF-UHFFFAOYSA-N 0.000 description 2
- UXFQFBNBSPQBJW-UHFFFAOYSA-N 2-amino-2-methylpropane-1,3-diol Chemical compound OCC(N)(C)CO UXFQFBNBSPQBJW-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 2
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 2
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- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 2
- 125000002339 acetoacetyl group Chemical group O=C([*])C([H])([H])C(=O)C([H])([H])[H] 0.000 description 2
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- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
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- 238000002242 deionisation method Methods 0.000 description 2
- 239000012975 dibutyltin dilaurate Substances 0.000 description 2
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- 239000000945 filler Substances 0.000 description 2
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- JFCQEDHGNNZCLN-UHFFFAOYSA-N glutaric acid Chemical compound OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 2
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- 229940051250 hexylene glycol Drugs 0.000 description 2
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- 239000012948 isocyanate Substances 0.000 description 2
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- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 2
- LVHBHZANLOWSRM-UHFFFAOYSA-N itaconic acid Chemical compound OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 2
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- BKIMMITUMNQMOS-UHFFFAOYSA-N nonane Chemical compound CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 2
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- KJFMBFZCATUALV-UHFFFAOYSA-N phenolphthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C(=O)O1 KJFMBFZCATUALV-UHFFFAOYSA-N 0.000 description 2
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/40—Polyesters derived from ester-forming derivatives of polycarboxylic acids or of polyhydroxy compounds, other than from esters thereof
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- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/68—Polyesters containing atoms other than carbon, hydrogen and oxygen
- C08G63/685—Polyesters containing atoms other than carbon, hydrogen and oxygen containing nitrogen
- C08G63/6854—Polyesters containing atoms other than carbon, hydrogen and oxygen containing nitrogen derived from polycarboxylic acids and polyhydroxy compounds
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- C09D167/00—Coating compositions based on polyesters obtained by reactions forming a carboxylic ester link in the main chain; Coating compositions based on derivatives of such polymers
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- Y10T428/31551—Of polyamidoester [polyurethane, polyisocyanate, polycarbamate, etc.]
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- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
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Abstract
本申请公开了一种可固化涂料组合物,其特征在于它包括:(1)一种聚酯,它是包括下列化合物的混合物的反应产物:(a)有至少一个氨基甲酸基侧基的多元醇,和(b)多元酸,和(2)一种具有多个与上述氨基甲酸侧基反应的官能基的固化剂。
Description
本发明涉及可固化涂料组合物,特别涉及含聚合物的可固化涂料组合物。
有氨基甲酸官能基因的聚合物和低聚物已用于各种可固化组合物中。例如在U.S.Patent 5,356,669和WO 94/10211中描述了氨基甲酸官能丙烯酸类聚合物。这些聚合物可用氨基甲酸官能丙烯酸类单体加成聚合或通过羟基官能丙烯酸类与氨基甲酸烷基酯转氨基甲酰化来制备。JP 51/4124描述了用羟基官能聚酯转氨基甲酰化制备的氨基官能聚酯。
聚酯现在广泛用于可固化组合物如涂料组合物中。这些树脂提供了许多有益的性能如良好的寿命,良好的挠性,通过并入适当的离子或非离子稳定基团在含水体系中良好的分散性,耐冲击强度,良好的粘性和其他物理性能如应力释放。与用于可固化组合物的聚酯树脂有关的一个方法是向其中并入足够量的官能基以获得所需的固化特性。羟基是在可固化组合物常规的官能基。但有侧羟基的聚酯树脂很难制备,因为在聚酯生成期间侧羟基将与酸基反应而消耗掉。羟官能基通常通过使用多元醇封端剂如三羟甲基丙烷并入到聚酯树脂中,获得端OH,但不能获得侧OH。这类树脂在固化时仅提供有限的交联密度。虽然交联密度通过使用支化聚酯可增加一些。该支化聚酯通过将三官能或多官能多无醇或多元酸并到聚酯反应混合物中制备。但由于凝胶作用支化度常常受限制。在可固化聚酯树脂体系中低交联密度通常必须使用高分子量树脂来补偿,而该高子量树脂更像热塑性树脂而不像热固性树脂。
氨基甲酸官能聚酯被描述在JP 51/4124。该文献描述了通过典型的羟基官能聚酯与氨基甲酸酯的酯基转移制备有氨基甲酸端基的聚酯的方法。
因此,本发明涉及制备有氨基甲酸侧基的聚酯聚合物或低聚物的新方法。
按照本发明,提供一种制备聚酯聚合物或低聚物的方法,
包括有至少一个氨基甲酸侧基的多元醇与多元酸反应以生成带有氨基甲酸侧基的聚酯。
在本发明另一个实施方案中,提供用上述方法制得的聚合物或低聚物。
在本发明第三个实施方案中,提供包括上述氨基甲酸官能聚酯和可与氨基甲酸反应的固化剂的涂料组合物。
有至少一个氨基甲酸基的多元醇可用各种方法制备。一种方法是有多个环状碳酸酯基的化合物与氨、氢氧化铵或伯胺反应以将环状碳酸酯基开环。该开环反应将每个环状碳酸酯环转化成羟基和氨基甲酸侧基。
有多个环状碳酸酯基的化合物可用几种方法制备。一种方法是多异氰酸酯或多酐与环状碳酸羟烷基酯反应。环状碳酸羟烷基酯可用许多方法来制备。一些环状碳酸羟烷基酯如碳酸3-羟丙基酯(即碳酸甘油酯)可商购。环状碳酸酯化合物可用几种不同方法的任何一种来制备。一种方法为将含环氧基化合物与CO2,优选在有催化剂加压下反应。有用的催化剂包括任何活化环氧乙烷环的化合物如叔胺的季盐(如溴化四甲基铵),锡或磷配合盐(如CH3)3SNI:(CH3)4PI)。在这类催化剂存在下环氧化物也可与β-丁内酯反应。在另一种方法中,二元醇如甘油在至少为80℃(通常在回流下)和催化剂(如碳酸钾)存在下与碳酸二乙酯反应生成碳酸羟烷基酯,另外,含下式结构的1,2-二元醇酮缩醇的官能化合物在至少60℃下,优选有痕量酸存在下用水开环,以生成1,2-乙二醇,然后再与碳酸二乙基酯反应生成环状碳酸酯。
从本领域可知,环状碳酸酯通常为5或6元环。优选5元环,因为它们易于合成和可商购。
用于本发明中优选的环状碳酸羟烷基酯可用下式表示:
其中R是1-18碳原子,优选1-6个碳原子,更优选1-3个碳原子羟烷基,R可被1个或多个其他取代基如保护后的胺或不饱和基团取代。更优选R是-CmH2mOH其中羟基可为伯或仲羟基,和m是1到8,再优选R是-(CH2)P-OH其中羟基是伯羟基和p是1到2。
与环状碳酸羟烷酯反应的有机多异氰酸酯基本上可为任何多异氰酸酯且优选二异氰酸酯,烃二异氰酸酯或取代的烃二异氰酸酯。许多这类有机二异氰酸酯在本领域是已知的,包括对苯二异氰酸酯,联苯-4,4’-二异氰酸酯,甲苯二异氰酸酯,3,3’-二甲基-4,4’-联苯二异氰酸酯,1,4-四亚甲基二异氰酸酯,1,6-六亚甲基二异氰酸酯,2,2,4-三甲基己-1,6-二异氰酸酯,亚甲基二(苯异氰酸酯),1,5-萘二异氰酸酯,双(异氰酸根合乙基富马酸酯),异佛尔酮二异氰酸酯(IPDI),四亚甲基二异氰酸酯,和亚甲基-二-(4-环己基异氰酸酯)。也可使用二元醇如乙二醇或1,2-丁二醇等的异氰酸酯终端的加成物。这些加成物可通过大于1摩尔二异氰酸酯如上述的二异氰酸酯与1摩尔二元醇反应以形成更长链的二异氰酸酯。另外,二元醇也可与二异氰酸酯一同加入。
虽然优选二异氰酸酯,但其他多官能异氰酸酯也可使用,例子是1,2,4-苯三异氰酸酯和多亚甲基多苯异氰酯。
多异氰酸酯和环状碳酸羟烷酯可在本领域已知的醇和异氰酸酯的条件下反应。
与环状碳酸羟烷基酯反应的多酸酐包括大量的本领域已知的化合物,例如,六氢化邻苯二甲酸酐,甲基六氢化邻苯二甲酸酐,马来酐,谷氨酸酐,1,2,4,5-双-酸酐环己烷。该反应通常在至少为80℃,优选98~120℃,在锡金属催化剂存在下进行。
有多个环状碳酸酯基的化合物也容易通过多环氧化物与二氧化碳反应转化环氧基成环状碳酸酯基。多环氧化物是本领域公知的。有用多环氧化物包括通过与表卤醇也可与环氧线性酚醛清漆反应而环氧化的三羟甲基丙烷。低聚或聚合的多环氧化物如含甲基丙烯酸缩水甘油酯的丙烯酸类低聚物或聚合物或环氧基封端的多缩水甘油基醚也可使用。其他多环氧化物,例如,环氧线性酚醛清漆也可使用。像其他环氧化物一样,环氧线性酚醛清漆可与二氧化碳反应以生成环状碳酸酯化合物。
虽然线性聚酯主要以有2个供酯化反应的官能基为基,带有多个3个官能基的环状碳酸酯也可提供支化聚酯。例如在二异氰酸酯如异佛尔酮二异氰酸酯上的异氰酸基可与多元醇加成以生成四官能醇,该醇被表卤醇环氧化以生成四官能多环氧化物,然后再与二氧化碳反应生成四官能环状碳酸酯。其他多官能度的多环氧化物,例如四(4-缩水甘油基氧苯基)乙烷也可与CO2反应生成多环状碳酸酯。
有多个环状碳酸酯基的化合物与氨、氢氧化铵或伯胺反应。该反应在温和的条件(例如,0-60℃,在水,甲醇或其他已知的溶剂中)下反应。与氨或氢氧化铵反应生成件氨基甲酸酯且是优选的。与件胺反应生成仲(N-取代的)氨基甲酸酯。氨,氢氧化铵或伯胺与环状碳酸酯基的开环反应生成如上所述的氨基甲酸基和伯或仲羟基,该羟基在本发明下一步中参加在生成聚氨酯反应中。这样获得的反应产物包括氨基甲酸侧基和端羟基。
制备有至少一个氨基甲酸侧基的多醇的另一种方法是环状碳酸羟烷酯与氨、氢氧化铵或伯胺反应。该反应如上述的带多个环状碳酸酯基化合物的开环反应一样进行。所得的化合物有两个羟基和一个氨基甲酯侧基。
在本发明聚酯上的氨基甲酸侧基可以是伯或仲基。伯氨基甲酸基可用下式表示:
仲氨基甲酸基可用下式表示:
其中R是1-8,优选1-4,更优选1个碳原子的取代或未取代烷基,或环脂肪烃基。应该明白术语烷基和环烷基包括取代的烷基和环烷基如卤素取代的烷基或环烷基或不饱和基取代的烷基,但应避免选择对固化后材料有不利影响的取代基。伯氨基甲酸基是经使用氨或氢氧化铵作为开环反应物在上述环碳酸酯的开环反应中生成的。
按照本发明,包括带至少一个氨基甲酸侧基的多元醇和多酸的混合物以生成聚酯。用于实施本发明的多元酸可在脂肪或芳香部分含2到34个碳原子和至少2个,优选不多于4个羧基,羧基也可为酸酐基形式。多元酸可以是多元酸本身或在聚酯反应期间能被含氨基甲酸基的二元醇或其他多元醇开环以形成用于聚酯缩合反应的酸基的多元酸的环状酸酐。有用的多元酸的例子包括邻苯二甲酸酐、对苯二甲酸酐、间苯二酸,己二酸,丁二酸,戊二酸,富马酸,马来酸,环己二酸,1,2,4-苯三酸酐,壬二酸,癸二酸,二聚酸,1,2,4,5-苯四酸二酐,取代的马来酸和富马酸如柠康酸,氯代马来酸或中康酸和取代的丁二酸如阿康酸和衣康酸。多元酸的混合物也可使用。
聚酯反应混合物能包括补加的多醇。这类补加的多醇的量由聚酯所需的氨基甲酸官能度值决定。有用的多元醇通常有大于2个,优选2到约10个,更优选约2到8碳原子及2到约6,优选2到约4个羟基。一些优选的多元醇的例子是下列的一个或多个:新戊二醇,乙二醇,丙二醇,丁二醇,六亚甲基二醇,1,2-环己烷二甲醇,1,3-环己烷二甲醇,1,4-环己烷二甲醇,三羟甲基丙烷,季戊四醇,新戊二醇羟基新戊酸酯,二乙二醇,三乙二醇,四乙二醇,二丙二醇,多丙二醇,己二醇,2-甲基-2-乙基-1,3-丙二醇,2-乙基-1,3-己二醇,1,3-戊二醇,硫二甘醇,1,3-丙二醇,1,3-丁二醇,2,3-丁二醇,1,4-丁二醇,2,2,4-三甲基-1,3-戊二醇,1,2-环己二醇,1,3-环己二醇,1,4-环己二醇,丙三醇,三羟甲基丙烷,三羟甲基乙烷,1,2,4-丁三醇,1,2,6-己三醇,二季戊四醇,三季戊四醇,甘露糖醇,山梨醇,甲基苷,本领域技术人员显而易见的化合物和它们的混合物。根据最终树脂所需性质,一些其他多元醇可并到反应混合物中如脂肪多元醇,酚类多元醇(例如氢醌,酚酞,双酚A),低聚或聚合多元醇(例如预成聚酯多元醇)。另外,其他化合物如反应调节剂,催化剂,溶剂,分散剂等本领域已知的化合物也可并入。
可选择多元酸及多元醇和任何其他活性化合物的比例以获得酸基终端聚酯或羟基终端聚酯。这可通过使用化学计量过量的多元酸或醇来实现。
如果水溶性是需要的,重要的是将水稳定基团嵌入到聚酯中。这可通过将水稳定的多醚多元醇并到反应混合物中以使它们并列聚酯中或通过在反应混合物中使用二甲醇丙酸作为多元醇来实现。
通过在聚酯反应混合物中使用过量的多元酸或多元醇组分,中间体聚酯树脂可制成具有羟基或酸基端基。树脂的端基然后可通过这些端基与本领域已知的过量的封端剂反应来控制。如果中间体树脂是酸端基,单或多官能醇可用来在所需阶段(通过测定粘度和异氰酸基浓度来确定)终止反应(将游离酸基封端)。多官能醇如乙二醇,三羟甲基丙烷和羟基终端的聚酯也可以这样方式使用。在仅有氨基甲酸基官能度而无羟基官能度的树脂中,中间体聚酯树脂优选用单官能醇(例如正丁醇)封端。同样,羟端基中间体树脂可通过与过量的单或多官能酸反应来封端。
聚酯反应通常在140℃和260℃之间进行3到15小时,使用或不使用酸酯化反应催化剂,如0.01到2.0%(重量)的磷酸或甲苯磺酸。反应任选在一种溶剂如本领域公知的芳烃存在下进行。反应可以单级或多级如二级来进行。这样制备的聚酯通常有1000到60000的数均分子量。
按本发明制备的树脂可掺入到可固化组合物如涂料组合物中。在本发明的可固化组合物中。固化通过氨基官能化聚酯组分与组分(2)反应来进行。组分(2)是有多个与聚酯上氨基甲酸侧基反应的官能基化合物。这类活性基团包括在氨基塑料交联剂或其他化合物如酚/甲醛加合物上的羟甲基或甲基烷氧基,硅氧烷基和酸酐基。固化剂的例子包括密胺甲醛树脂(包括单体的或聚合的密胺树脂和部分或全部烷基化的密胺树脂),脲树脂(例如,羟甲基脲类如脲甲醛树脂,烷氧基脲类如丁基化脲甲醛树脂),聚酸酐(如聚丁二酸酐),和聚硅氧烷类(如,三甲氧基硅氧烷),氨基塑料树脂如密胺甲醛树脂或脲甲醛树脂是特别优选的。
在可固化组合物中,可任选使用溶剂。虽然本发明的组合物可以基本上为固体粉末或分散体使用,但通常希望该组合物基本上为液态,这可使用溶剂来实现。这种溶剂应对氨基甲酸官能基树脂和固化剂都起到溶剂的作用。通常,根据组分溶解度特性,溶剂可以是任何有机溶剂和/或水。在一优选的实施方案中,溶剂是极性有机溶剂。更优选,溶剂是极性脂肪溶剂或极性芳香溶剂。再优选,溶剂是酮,酯,乙酸酯,非极性酰胺,非极性亚砜或非极性胺。有用溶剂的例子包括甲乙酮,甲异丁酮,乙酸间-戊基酯,乙二醇丁基醚-乙酸酯,丙二醇单甲醚乙酸酯,二甲苯,N-甲基吡咯烷酮或芳烃的混合物。在另一个优选的实施方案中,溶剂是水或水与少量助溶剂的混合物。
用于实施本发明的可固化组合物可包括催化剂以提高固化反应。例如,当使用氨基塑料化合物特别是单体密胺时,强酸催化剂可用来提高固化反应。这类催化剂是本领域公知的且包括例如对-甲苯磺酸,二壬基萘二磺酸,十二烷基苯磺酸,磷酸苯酯,马来酸单丁基酯,磷酸丁酯和羟基磷酸酯。强酸催化剂常常例如用胺来保护,可用于本发明中的其他催化剂包括路易斯酸,锌盐和锡盐。
在本发明一优选实施方案中,可固化组合物中溶剂量为约0.01%~99%(重量),优选约10%~60%(重量),更优选约30%~50%(重量)。
涂料组合物可用本领域已知的大量方法涂到物品上。这些方法包括例如喷涂,浸涂,辊涂,幕涂等。对于汽车表盘,优选喷涂。
任何附加使用的试剂例如表面活性剂,填料稳定剂,润湿剂,分散剂,粘合促进剂,UV吸收剂,HALS等都可并入列涂料组合物中。虽然这些试剂是先有技术中公知的,使用量必须控制以避免对涂料性质有不利影响。
按照本发明的可固化涂料优选用于高光泽涂料中和/或作为颜色+透明度的复合涂料的透明涂层使用。用于本文中的高光泽涂料是有20°的光泽度(ASTMD 523-89)或DOI为至少80(ASTME430-91)的涂料。用于本文中的高光涂涂料也可作为颜色+透明度复合涂料的底涂层来使用。
当本发明的涂料组合物作为高光泽度的颜料漆涂料时,颜料可为任何有机或无机化合物或色料,填料,金属或其他无机薄片材料如云母或铝溥片和其他类型通常称为颜料的材料。颜料基于组分A和B的总固体量为1%到100%(重量)(即颜料:B为0.1到1)。
当本发明的涂料组合物用作颜色+透明度的复合涂料的透明涂层时,颜料底层涂层组分可为本领域已知的大量类型的任一种,而且无须详细解释。用于底层涂层的本领域已知的聚合物包括丙烯酸类聚合物,乙烯类聚合物,聚氨酯,聚碳酸酯,聚酯,醇酸树脂和聚硅氧烷。优选的聚合物包括丙烯酸类聚合物和聚氨酯。在一优选的本发明实施方案中,底涂层组合物也使用氨基甲酸官能丙烯酸类聚合物。底涂层聚合物可为热塑性的,但优选是可交联的且包括一种或多种可交联官能基。这类基团包括例如,羟基,异氰酸基,胺基,环氧基,丙烯酸基,乙烯基,硅烷基和乙酰乙酸基。这些基团可用这样的方式保护,以使它们在所需的固化条件下通常为升温下可脱保护并为交联反应使用。有用的可交联官能基包括羟基,环氧基,酸基,酸酐基,硅烷基和乙酰乙酸基。优选的可交联官能基包括羟官能基和氨基官能基。
底涂层可为自交联的或需要与聚合物官能剂反应的另外的交联剂。
当聚合物包括羟基官能基时,例如交联剂可为氨基塑料树脂,异氰酸基和保护的异氰酸基(包括异氰脲酸基类)和酸或酸酐官能交联剂。
描述在本文中的涂料组合物优选置于固化涂料涂层的条件下。虽然可使用各种固化方法,但优选热固化。通常热固化通过将涂布后的物品暴露在高温(主要由热辐射源提供)下来进行。固化温度将随用于交联剂中的特定保护剂而变化,但通常在93℃到177℃之间。本发明的化合物在比较低的固化温度下仍是反应性的。这样,在优选的实施方案中,对于保护的酸催化体系,因化温度优选在115℃到150℃之间,更优选在115℃到138℃之间。对于未保护酸催化体系,固化温度优选在82℃到99℃。固化时间随所用的具体组分,和物理参数如层的厚度而变化,但典型的固化时间对保护的催化体系为15到60分钟,优选15-25分钟;对未保护酸催化体系为10-20分钟。
本发明进一步用下列实施例来描述。
实施例1制备有至少一个氨基甲酸侧基的多元醇
一个三颈圆底烧瓶装有一个指形真空冷凝器,搅拌器,装有多孔碎玻璃片的氨进气管和热电偶。该装置然后放在一金属容器中,该容器作为冷浴装有干冰、水、丙酮和氯化钠以控制反应温度。将环状碳酸羟烷酯(GlycarR)与等摩尔量的甲醇装入反应器。反应组分温度降到15℃,此时鼓氨气到反应器直至反应温度增至32℃。此时继续搅拌反应物并冷却到15℃。该操作连续进行直到在红外谱图上不再有碳酸酯峰。
当所有的Glycar转化成二元醇氨基甲酸酯后,改装反应装置以便进行加热汽提。加热汽提在室温下开始以防止崩沸或体系膨胀。在28英寸汞高下缓慢升温(体系允许的)到80℃。真空汽提结束并吹扫气相色谱的氨和甲醇。
实施例2 制备带有氨基甲酸官能侧基的线性芳/脂肪聚酯多元醇
一个3颈圆底烧瓶装有一5块多孔板的精馏柱,搅拌器,带有50毫升溶剂阱的Claiscn应接器,冷凝器,氨进气管和热电偶。该反应器装有下列组分:
组分
重量
二聚脂肪酸Empol1010 1612.34
甲苯(共沸溶剂) 100.00
1,6-己二醇 673.14
邻苯二甲酸 462.80
氨基甲酸基甘醇 227.51
二甲基锡二月桂酯
0.50
2976.29
搅拌器在低速下打开。将50克甲苯加到收集阱中并缓慢加热到137.7℃。当反应达到137.7℃时,在该温度下保持2.5小时(观察到甲苯和水的共沸物)。保持2.5小时后,缓慢升温到170℃,此时观察到很强的甲苯和水的共沸物。将反应温度在170℃保持8小时,此时测定第一酸数。然后每隔1小时测定一次酸数直到反应达到(5~10)AN或(0.089~0.178)毫当量/克。当反应达到预定酸数后,用水馏出甲苯直到所有的甲苯被收集。将反应冷却到100℃,并加入800克Exxate800到反应物中,将浴连续冷却到室温。
实施例3 制备带氨基甲酸官能侧基的线性芳/脂肪聚酯多醇。
一个3颈圆底烧瓶装有一5块多孔板的精馏柱,搅拌器,带有50毫升溶剂阱的Claiscn应接器,冷凝器,氨进气管和热电偶。该反应器装有下列组分:
组分
重量
二聚酸EmpolR 1010 2022.71
甲苯(共沸溶剂) 100.00
1,6-己二醇 673.14
邻苯二甲酸 499.35
氨基甲酸基甘醇 136.35
二丁基锡二月桂酸酯
0.50
3378.03
搅拌器在低速下打开。将50克甲苯加到收集阱中并缓慢加热到137.7℃。当反应达到137.7℃时,在该温度下保持2.5小时(观察到甲苯和水的共沸物)。保持2.5小时后,缓慢升温到170℃,此时观察到很强的甲苯和水的共沸物。将反应温度在170℃保持8小时,此时测定第一酸数。然后每隔1小时测定一次酸数直到反应达到(5~8)AN或(0.089~0.143)毫当量/克。当反应达到预定酸数后,用水馏出甲苯直到所有的甲苯被收集。将反应冷却到100℃,并加入900克ExxateR 800到反应物中,将浴连续冷却到室温。
实施例4 制备带有氨基甲酸官能侧基的线性脂肪聚酯多醇
一个3颈圆底烧瓶装有一5块多孔板的精馏柱,搅拌器,带有50毫升溶剂阱的Claiscn应接器,冷凝器,氨进气管和热电偶。该反应器装有下列组分:
组分
重量
二聚酸Empol1010 2022.71
甲苯(共沸溶剂) 100.00
1,6-己二醇 719.12
己二醇 499.35
氨基甲酸基甘醇 136.35
二丁基锡二月桂酸酯
0.50
3478.03
搅拌器在低速下打开。将50克甲苯加到收集阱中并缓慢加热到137.7℃。当反应达到137.7℃时,在该温度下保持4小时(观察到甲苯和水的共沸物)。保持4小时后,缓慢升温到170℃,此时观察到很强的甲苯和水的共沸物。将反应温度在170℃保持8小时,此时测定第一酸数。然后每隔1小时测定一次酸数直到反应达到(5~10)AN或(0.089~0.178)毫当量/克。当反应达到预定酸数后,用水馏出甲苯直到所有的甲苯被收集。将反应冷却到100℃,并加入900克Exxate800到反应物中,将浴连续冷却到室温。
实施例5 制备带有氨基甲酸侧官能基的溶剂分散的聚酯/聚氨酯
一个3颈圆底烧瓶装有一个冷凝器、搅拌器、氮进气管和热电偶。该反应器装有下列组分:
组分
重量
带有氨基甲酸侧官能基
的聚酯多元醇(见实施例1) 1732.49
甲丙酮 362.69
新戊二醇 176.52
异佛尔酮二异氰酸酯(IPDI) 651.70
甲乙酮 143.00
在所有上述组分加到反应器中后,将反应混合物加热到99.8℃。当反应进行到有轻微放热时,反应温度升到约107.0℃。放热后,反应温度在(107.0-110)℃下保持3小时。此时测定第一NCO数。目标值为(0.24~0.25)meg NCO/克树脂。当NCO数处于该范围加入101.68克三羟甲基丙烷(TMP),此时为反应封端阶段。在TMP加入后,将反应保持1.5小时并测定最终NCO数。当NCO数被测定不再有时,反应结束,将反应物冷却到87.7℃,此时加入1036.23g Exxate800并结束反应。
实施例6 带有氨基甲酸侧基的水分散的聚酯/聚氨酯
一个3颈圆底烧瓶装有一个冷凝器、搅拌器、氮进气管和热电偶。该反应器装有下列组分:
组分
重量
带有氨基甲酸侧官能基
的聚酯多元醇(见实施例1) 1732.49
甲丙酮 362.69
新戊二醇 138.11
异佛尔酮二异氰酸酯(IPDI) 651.70
二甲基丙酸 53.41
甲乙酮 158.00
在所有上述组分加到反应器中后,将反应混合物加热到99.8℃。当反应进行到有轻微放热时,反应温度升到约107.2℃。放热后,反应温度在(107.0-110)℃下保持3小时。此时测定第一NCO数。目标值为(0.23~0.24)meq NCO/克树脂。当NCO数处于该范围加入92.99克三羟甲基丙烷(TMP),此时为反应封端阶段。在TMP加入后,将反应保持1.5小时并测定最终NCO数。当NCO数被测定不再有时,反应结束,将反应物冷却到87.0℃,此时加入200.34g丁基纤维素。将反应进一步冷却到82.0℃,此时加入34.9g二甲基乙醇胺(DMEA)并混合1小时以完成反应的盐化阶段。放置后,将混合物冷却到67.0℃,此时加入50.47g ExxateR和2867.41克去离子(DI)水。在加入DI水后,混合反应混合物2小时以完成树脂在水相的分散。
本发明已参照其优选实施方案进行详细描述。但应该明白在本发明的精神和范围内可作各种变化和变型。
Claims (4)
1.一种可固化涂料组合物,其特征在于它包括:
(1)一种聚酯,它是包括下列化合物的混合物的反应产物:
(a)有至少一个氨基甲酸基侧基的多元醇,和
(b)多元酸,和
(2)一种具有多个与上述氨基甲酸侧基反应的官能基的固化剂。
2.根据权利要求1的可固化涂料组合物,其特征在于固化剂是氨基塑料。
3.根据权利要求2的可固化涂料组合物,其特征在于氨基塑料是密胺树脂。
4.按照权利要求1的可固化涂料组合物,其特征在于化合物(1)(a)是(i)和(ii)的反应产物:
(i)有多个环状碳酸酯基的化合物或环状碳酸羟烷酯,
(ii)氨,氢氧化铵或伯胺。
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US361245 | 1989-06-05 | ||
US08/361,245 US5532061A (en) | 1994-12-21 | 1994-12-21 | Carbamate-functional polyester polymer or oligomer having pendant carbomate groups |
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CN95120874A Division CN1073583C (zh) | 1994-12-21 | 1995-12-20 | 带有氨基甲酸侧基的氨基甲酸官能聚酯聚合物或低聚物 |
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CN95120874A Expired - Fee Related CN1073583C (zh) | 1994-12-21 | 1995-12-20 | 带有氨基甲酸侧基的氨基甲酸官能聚酯聚合物或低聚物 |
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US (1) | US5532061A (zh) |
EP (1) | EP0718339B1 (zh) |
JP (1) | JP3429934B2 (zh) |
KR (1) | KR100353302B1 (zh) |
CN (2) | CN1223641C (zh) |
AU (1) | AU692004B2 (zh) |
BR (1) | BR9505969A (zh) |
CA (1) | CA2165025C (zh) |
DE (1) | DE69533101T2 (zh) |
ES (1) | ES2222460T3 (zh) |
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WO1995029947A1 (en) * | 1994-04-29 | 1995-11-09 | Ppg Industries, Inc. | Flexible aminoplast-curable film-forming compositions providing films having resistance to acid etching |
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US5759694A (en) * | 1996-09-04 | 1998-06-02 | Ppg Industries, Inc. | Carbamate functional polymers and oligomers and coating compositions containing same |
US5922475A (en) * | 1997-04-29 | 1999-07-13 | Ppg Industries Ohio, Inc. | Color-plus-clear composite coating compositions containing alkylolated or etherified carbanate functional polymers |
US5888655A (en) * | 1997-06-30 | 1999-03-30 | Basf Corporation | Primer coating compositions containing carbamate-functional novolac resins |
US5907024A (en) * | 1997-11-12 | 1999-05-25 | Basf Corporation | High solids thermosetting compositions with dual cure mechanism |
US5945499A (en) * | 1997-11-12 | 1999-08-31 | Basf Corporation | High solids thermosetting compositions with dual cure mechanism |
US6624275B2 (en) | 2001-11-02 | 2003-09-23 | Basf Corporation | Water- and organic-soluble carbamate material |
US6624241B2 (en) | 1999-05-21 | 2003-09-23 | Basf Corporation | Waterborne coating compositions containing materials dispersed with water-soluble carbamate materials |
US6624279B2 (en) | 1999-05-21 | 2003-09-23 | Basf Corporation | Water-soluble carbamate materials |
US7205029B2 (en) * | 2000-12-19 | 2007-04-17 | Basf Corporation | Method of providing cured coating films free of popping defects |
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US6716953B2 (en) | 2002-05-16 | 2004-04-06 | Ppg Industries Ohio, Inc. | Etherified carbamate crosslinking agents and their use in curable compositions, particularly film-forming compositions |
US20040087728A1 (en) * | 2002-10-31 | 2004-05-06 | Donald Campbell | Carbamate functional addition polymers and a method for their preparation |
US7232863B2 (en) | 2002-10-31 | 2007-06-19 | Basf Corporation | Functional addition polymers and a method for their preparation |
JP4134756B2 (ja) * | 2003-02-28 | 2008-08-20 | 東海ゴム工業株式会社 | 液封エンジンマウント装置におけるゴムストッパ |
US8686090B2 (en) * | 2003-12-10 | 2014-04-01 | Basf Coatings Gmbh | Use of urea crystals for non-polymeric coatings |
GB2415197A (en) * | 2004-06-18 | 2005-12-21 | Baxenden Chem | Urethane-group containing diol or polyol polymer products and their use as coatings |
US7858190B2 (en) * | 2005-09-15 | 2010-12-28 | Basf Coatings Gmbh | Thermosetting coating compositions with multiple cure mechanisms |
US20080124532A1 (en) * | 2006-11-29 | 2008-05-29 | Basf Corporation | Materials and oligomers in low voc coatings |
DE102007012229A1 (de) * | 2007-03-12 | 2008-09-18 | Basf Se | Verfahren zur Herstellung von Produkten |
US20080293901A1 (en) * | 2007-05-25 | 2008-11-27 | Basf Corporation | Polymers and compounds prepared with alpha-methylene lactones, methods therefor, and coatings |
US20090053420A1 (en) * | 2007-08-20 | 2009-02-26 | Basf Corporation | Thermosetting coating compositions with multiple cure mechanisms |
US20090074978A1 (en) * | 2007-09-13 | 2009-03-19 | Basf Corporation | Method of making carbamate functional materials |
US11136469B2 (en) | 2016-07-26 | 2021-10-05 | Ppg Industries Ohio, Inc. | Acid-catalyzed curable coating compositions containing 1,1-di-activated vinyl compounds and related coatings and processes |
EP3401348A1 (en) * | 2017-05-11 | 2018-11-14 | Henkel AG & Co. KGaA | Method for producing functionalized polyesters |
EP3498745A1 (de) * | 2017-12-18 | 2019-06-19 | Covestro Deutschland AG | Flammgeschützte polyurethan-hartschaumstoffe |
CN114058309A (zh) * | 2021-11-08 | 2022-02-18 | 南京南溧新材料有限公司 | 一种生物基ms胶基础树脂及其制备方法 |
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-
1994
- 1994-12-21 US US08/361,245 patent/US5532061A/en not_active Expired - Lifetime
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1995
- 1995-12-12 CA CA 2165025 patent/CA2165025C/en not_active Expired - Fee Related
- 1995-12-14 DE DE1995633101 patent/DE69533101T2/de not_active Expired - Lifetime
- 1995-12-14 EP EP19950119723 patent/EP0718339B1/en not_active Expired - Lifetime
- 1995-12-14 ES ES95119723T patent/ES2222460T3/es not_active Expired - Lifetime
- 1995-12-20 KR KR1019950053037A patent/KR100353302B1/ko not_active IP Right Cessation
- 1995-12-20 AU AU40575/95A patent/AU692004B2/en not_active Ceased
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KR960022667A (ko) | 1996-07-18 |
CN1073583C (zh) | 2001-10-24 |
EP0718339A3 (en) | 1996-10-02 |
JP3429934B2 (ja) | 2003-07-28 |
CA2165025C (en) | 2005-04-26 |
CN1133306A (zh) | 1996-10-16 |
AU692004B2 (en) | 1998-05-28 |
CA2165025A1 (en) | 1996-06-22 |
ES2222460T3 (es) | 2005-02-01 |
DE69533101D1 (de) | 2004-07-08 |
AU4057595A (en) | 1996-06-27 |
DE69533101T2 (de) | 2005-09-22 |
JPH08231695A (ja) | 1996-09-10 |
EP0718339A2 (en) | 1996-06-26 |
BR9505969A (pt) | 1997-12-23 |
KR100353302B1 (ko) | 2003-01-24 |
EP0718339B1 (en) | 2004-06-02 |
CN1492011A (zh) | 2004-04-28 |
US5532061A (en) | 1996-07-02 |
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