CN101410431A - 包含脲基甲酸酯改性的异氰酸酯的聚氨酯弹性体 - Google Patents
包含脲基甲酸酯改性的异氰酸酯的聚氨酯弹性体 Download PDFInfo
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- CN101410431A CN101410431A CNA2007800045212A CN200780004521A CN101410431A CN 101410431 A CN101410431 A CN 101410431A CN A2007800045212 A CNA2007800045212 A CN A2007800045212A CN 200780004521 A CN200780004521 A CN 200780004521A CN 101410431 A CN101410431 A CN 101410431A
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- 229920003225 polyurethane elastomer Polymers 0.000 title claims abstract description 11
- 239000012948 isocyanate Substances 0.000 title claims description 19
- 150000002513 isocyanates Chemical class 0.000 title claims description 15
- AVWRKZWQTYIKIY-UHFFFAOYSA-N urea-1-carboxylic acid Chemical compound NC(=O)NC(O)=O AVWRKZWQTYIKIY-UHFFFAOYSA-N 0.000 title abstract description 10
- 239000005056 polyisocyanate Substances 0.000 claims abstract description 66
- 229920001228 polyisocyanate Polymers 0.000 claims abstract description 66
- 238000000034 method Methods 0.000 claims abstract description 38
- 229920000570 polyether Polymers 0.000 claims abstract description 20
- 239000004721 Polyphenylene oxide Substances 0.000 claims abstract description 18
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 14
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 14
- 150000002894 organic compounds Chemical class 0.000 claims abstract description 7
- -1 carbon atom fatty alcohol Chemical class 0.000 claims description 66
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 31
- 229910052799 carbon Inorganic materials 0.000 claims description 21
- 239000000049 pigment Substances 0.000 claims description 18
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 claims description 17
- 239000005057 Hexamethylene diisocyanate Substances 0.000 claims description 15
- 150000001412 amines Chemical class 0.000 claims description 15
- 239000000654 additive Substances 0.000 claims description 14
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 claims description 14
- 238000006243 chemical reaction Methods 0.000 claims description 12
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 claims description 9
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- 239000003795 chemical substances by application Substances 0.000 description 13
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- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 11
- 239000005058 Isophorone diisocyanate Substances 0.000 description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
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- RKMGAJGJIURJSJ-UHFFFAOYSA-N 2,2,6,6-Tetramethylpiperidine Substances CC1(C)CCCC(C)(C)N1 RKMGAJGJIURJSJ-UHFFFAOYSA-N 0.000 description 9
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- 239000001257 hydrogen Substances 0.000 description 5
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- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 5
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- LCZVSXRMYJUNFX-UHFFFAOYSA-N 2-[2-(2-hydroxypropoxy)propoxy]propan-1-ol Chemical compound CC(O)COC(C)COC(C)CO LCZVSXRMYJUNFX-UHFFFAOYSA-N 0.000 description 4
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 4
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- KXBFLNPZHXDQLV-UHFFFAOYSA-N [cyclohexyl(diisocyanato)methyl]cyclohexane Chemical compound C1CCCCC1C(N=C=O)(N=C=O)C1CCCCC1 KXBFLNPZHXDQLV-UHFFFAOYSA-N 0.000 description 4
- 125000003368 amide group Chemical group 0.000 description 4
- 150000001408 amides Chemical class 0.000 description 4
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 4
- 239000012964 benzotriazole Substances 0.000 description 4
- 229910052797 bismuth Inorganic materials 0.000 description 4
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 4
- 229910052500 inorganic mineral Inorganic materials 0.000 description 4
- LGRLWUINFJPLSH-UHFFFAOYSA-N methanide Chemical compound [CH3-] LGRLWUINFJPLSH-UHFFFAOYSA-N 0.000 description 4
- 239000011707 mineral Substances 0.000 description 4
- 238000006116 polymerization reaction Methods 0.000 description 4
- 229920002635 polyurethane Polymers 0.000 description 4
- 239000004814 polyurethane Substances 0.000 description 4
- 150000003335 secondary amines Chemical class 0.000 description 4
- UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 4
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 4
- BUZADCOBPZFEQO-UHFFFAOYSA-N 1,1-bis(methylamino)urea Chemical compound CNN(C(=O)N)NC BUZADCOBPZFEQO-UHFFFAOYSA-N 0.000 description 3
- AIDLAEPHWROGFI-UHFFFAOYSA-N 2-methylbenzene-1,3-dicarboxylic acid Chemical compound CC1=C(C(O)=O)C=CC=C1C(O)=O AIDLAEPHWROGFI-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
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- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
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- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 3
- 150000007942 carboxylates Chemical class 0.000 description 3
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
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- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 3
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- IKEHOXWJQXIQAG-UHFFFAOYSA-N 2-tert-butyl-4-methylphenol Chemical compound CC1=CC=C(O)C(C(C)(C)C)=C1 IKEHOXWJQXIQAG-UHFFFAOYSA-N 0.000 description 2
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- 239000005012 oleoresinous Substances 0.000 description 1
- NDLPOXTZKUMGOV-UHFFFAOYSA-N oxo(oxoferriooxy)iron hydrate Chemical compound O.O=[Fe]O[Fe]=O NDLPOXTZKUMGOV-UHFFFAOYSA-N 0.000 description 1
- GNRSAWUEBMWBQH-UHFFFAOYSA-N oxonickel Chemical compound [Ni]=O GNRSAWUEBMWBQH-UHFFFAOYSA-N 0.000 description 1
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- NQPDZGIKBAWPEJ-UHFFFAOYSA-N pentanoic acid group Chemical group C(CCCC)(=O)O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- DGBWPZSGHAXYGK-UHFFFAOYSA-N perinone Chemical compound C12=NC3=CC=CC=C3N2C(=O)C2=CC=C3C4=C2C1=CC=C4C(=O)N1C2=CC=CC=C2N=C13 DGBWPZSGHAXYGK-UHFFFAOYSA-N 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
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- 230000000704 physical effect Effects 0.000 description 1
- JTHRRMFZHSDGNJ-UHFFFAOYSA-N piperazine-2,3-dione Chemical compound O=C1NCCNC1=O JTHRRMFZHSDGNJ-UHFFFAOYSA-N 0.000 description 1
- 150000003053 piperidines Chemical class 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
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- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- IZMJMCDDWKSTTK-UHFFFAOYSA-N quinoline yellow Chemical compound C1=CC=CC2=NC(C3C(C4=CC=CC=C4C3=O)=O)=CC=C21 IZMJMCDDWKSTTK-UHFFFAOYSA-N 0.000 description 1
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- JOUDBUYBGJYFFP-FOCLMDBBSA-N thioindigo Chemical compound S\1C2=CC=CC=C2C(=O)C/1=C1/C(=O)C2=CC=CC=C2S1 JOUDBUYBGJYFFP-FOCLMDBBSA-N 0.000 description 1
- AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 1
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- 239000012745 toughening agent Substances 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
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- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- 150000004072 triols Chemical class 0.000 description 1
- 229960004418 trolamine Drugs 0.000 description 1
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- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052984 zinc sulfide Inorganic materials 0.000 description 1
- NHXVNEDMKGDNPR-UHFFFAOYSA-N zinc;pentane-2,4-dione Chemical compound [Zn+2].CC(=O)[CH-]C(C)=O.CC(=O)[CH-]C(C)=O NHXVNEDMKGDNPR-UHFFFAOYSA-N 0.000 description 1
- DRDVZXDWVBGGMH-UHFFFAOYSA-N zinc;sulfide Chemical compound [S-2].[Zn+2] DRDVZXDWVBGGMH-UHFFFAOYSA-N 0.000 description 1
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Abstract
本发明涉及包含脲基甲酸酯改性的异氰酸酯的聚氨酯弹性体及其生产方法。这些弹性体包含多异氰酸酯组分与异氰酸酯-活性组分在一种或多种催化剂存在下的反应产物,所述多异氰酸酯组分包含NCO基团含量约为15-35%的脲基甲酸酯改性的脂(环)族多异氰酸酯或其预聚物,所述异氰酸酯-活性组分包含一种或多种不含胺基的聚醚多元醇,和含有两个羟基且不含有胺基的低分子量有机化合物。
Description
发明背景
本发明涉及耐候性提高的聚氨酯弹性体及其生产方法。
通过反应注塑(即RIM)技术生产聚氨酯模塑制品是众所周知的,并且例如在美国专利4218543中进行了描述。RIM方法涉及一种填充模具的技术,通过该技术在非常短的时间内使用高输出量、高压计量设备将高活性液体起始组分在它们已经在所谓的“完全控制混合头”中混合后注入到模具中。
在通过RIM方法生产聚氨酯模塑制品中,反应混合物通常包含A部分和B部分,A部分基于多异氰酸酯,B部分基于含异氰酸酯-活性氢原子的有机化合物,以及合适的增链剂、催化剂、发泡剂和其它添加剂。适用于工业RIM方法的多异氰酸酯是芳族异氰酸酯,例如二苯基甲烷-4,4′-二异氰酸酯(即MDI)。虽然各种专利在描述为适用于RIM方法的一长列异氰酸酯中大致揭示了脂环族异氰酸酯,但是几乎没有专利提及使用脂环族异氰酸酯的任何工作实施例。
美国专利4,772,639描述了在闭合模具中,在催化剂和助剂存在下,使有机多异氰酸酯与含有异氰酸酯-活性氢原子的有机化合物反应而生产聚氨酯模塑制品的方法。所述异氰酸酯组分是基于(a1)(i)1-异氰酸酯-3,3,5-三甲基-5-异氰酸甲酯基环己烷(IPDI)和(ii)通过使1,6-己二异氰酸酯的一部分异氰酸酯基进行三聚制备的含异氰脲酸酯基的多异氰酸酯的混合物,或者(a2)(i)IPDI和(iii)通过使1,6-己二异氰酸酯和IPDI的混合物的一部分异氰酸酯基进行三聚制备的含异氰脲酸酯基的多异氰酸酯。这些反应混合物被大致揭示为适合用于RIM加工。
美国专利4,642,320揭示了制备模塑聚合物的方法,该方法包括在闭合模具内使包含(a)、(b)和(c)的反应混合物反应,其中(a)是含活性氢的物质,包括平均当量重量至少为500的伯胺或仲胺封端的聚醚,(b)是至少一种增链剂,(c)是脂(环)族多异氰酸酯、多异硫氰酸酯或它们的混合物,其中NCX指数约为0.6-1.5。该方法需要组分(a)的至少25%、优选50%的活性氢原子以胺氢的形式存在。所有实施例揭示了在高模具温度和长脱模时间下的基于HDI预聚物与胺封端的聚醚和二乙基甲苯二胺的体系。
美国专利4,764,543揭示了使用非常快速反应的脂族多胺的脂族RIM体系。该专利限于基于脂环族二胺和聚醚(其是胺封端的聚醚)的增链剂,以及与脂族基连接的多异氰酸酯的全部聚脲体系。
美国专利4,269,945中也揭示了RIM体系。这些体系基于包含多异氰酸酯、含羟基多元醇和特定的增链剂的组合物。特定的增链剂包含(1)至少一种选自下组的组分:(a)基本不含脂族胺氢原子的含羟基物质和(b)基本不含脂族胺氢原子的含有至少两个芳族胺氢原子的含芳族胺物质;和(2)至少一种具有至少一个伯胺基且平均脂族胺氢官能度约为2-16的含脂族胺物质。芳族多异氰酸酯和脂(环)族多异氰酸酯被揭示都适用于该方法。在该专利的所有工作实施例中都使用本质上可能为聚合物的芳族异氰酸酯。
美国专利5,260,346还揭示了通过RIM法制备弹性体的反应体系。这些体系需要脲基甲酸酯改性的多异氰酸酯、含羟基的多元醇和其中胺基邻位中的至少一个被低级烷基取代基取代的芳族多胺。
美国专利5,502,147描述了基于脂(环)族异氰酸酯的RIM体系。这些脂(环)族异氰酸酯在25℃的粘度小于20,000mPa·s,NCO官能度为2.3-4.0,并且被以下基团改性:异氰脲酸酯基、缩二脲基、氨基甲酸酯基、脲基甲酸酯基、碳二亚胺基、噁二嗪-三酮基、脲二酮基和它们的混合物。B部分包含高分子量多元醇和低分子量增链剂,其中OH∶NH之比为1∶1至25∶1。
共同转让的美国专利5,502,150揭示了一种RIM方法,该方法使用官能度小于2.3、NCO含量为5-25%、单体含量小于2重量%的1.6-己二异氰酸酯预聚物。该预聚物与高分子量异氰酸酯-活性化合物、选自二醇和氨基醇的增链剂、含有不超过1个脂族胺氢原子的基于羟基的交联化合物反应。
美国专利5,656,677和6,242,555中还揭示了光稳定的聚氨酯。U.S.5,656,677的聚氨酯包含在增链剂和/或交联剂以及特定的催化剂体系存在下,脂(环)族异氰酸酯与含异氰酸酯-活性氢原子的化合物的反应产物。所述催化剂体系包含1)至少一种有机铅化合物,2)至少一种有机铋化合物和/或3)至少一种有机锡化合物。U.S.6,242,555揭示的光稳定的弹性体包含A)NCO基团含量为24.5-34%的异佛尔酮二异氰酸酯三聚体/单体混合物与B)异氰酸酯-活性组分在C)至少一种选自有机铅(II)、有机铋(III)和有机锡(IV)化合物的催化剂存在下的反应产物。
美国专利5,770,674揭示了一种由聚氨酯/脲组合物生产窗密封垫(windowgaskets)的方法。这些组合物包含以下物质的反应产物:NCO官能度为2.0-4.0的脂(环)族多异氰酸酯;异氰酸酯-活性组分,包含含有羟基、胺基或它们的混合物的较高分子量有机化合物;选自二醇、伯胺、仲胺、氨基醇和它们的混合物的低分子量增链剂;得到的组合物的交联密度至少为0.3摩尔/千克。
共同转让的2005年12月15日提交的美国申请序列11/300,958中揭示了快速固化脂族RIM弹性体。这些弹性体包含(1)NCO基团含量约为20-45重量%、官能度约为2.0-2.7且包含三聚的脂(环)族多异氰酸酯的异氰酸酯组分,以及(2)不含胺基团的高分子量聚醚多元醇和也不含胺基团的低分子量化合物,并且存在(3)一种或多种催化剂。
也共同转让的2006年12月15日提交的美国申请序列11/304,265涉及耐候性改善的聚氨酯弹性体。这些弹性体包含(1)NCO基团含量约为20-45重量%、官能度约为2.0-2.7且包含三聚的脂(环)族多异氰酸酯的异氰酸酯组分,以及(2)具有低不饱和度的高分子量聚醚多元醇、不含胺基团的低分子量化合物和任选的胺起始的低分子量化合物,并且存在(3)一种或多种催化剂。
共同转让的2005年12月15日提交的美国申请序列11/300,957中也揭示了聚氨酯弹性体。这些弹性体包含(1)脲基甲酸酯改性的异氰酸酯或其预聚物,(2)具有低不饱和度的高分子量聚醚多元醇,不含胺基团的低分子量化合物,和任选的胺起始的低分子量化合物,并且存在(3)一种或多种催化剂。
本发明的优点包括在不需要基于铅的催化剂的情况下,提高了固化,并且简化了催化。另外,本发明的弹性体表现出改进的挠曲模量。还认为这些弹性体表现出改善的耐候性。
发明概述
本发明涉及聚氨酯弹性体及其生产方法。
这些聚氨酯弹性体包含(A)与(B)在(C)和任选的(D)存在下的反应产物:
(A)多异氰酸酯组分,其包含(I)NCO基团含量约为15-35重量%、优选约为15-25重量%的脲基甲酸酯改性的多异氰酸酯,其包含(1)和(2)的反应产物:
(1)NCO基团含量约为25-60%、优选约为30-50%的脂(环)族多异氰酸酯组分,
(2)选自下组的有机醇:含有约1-36个碳原子的脂族醇、含有约5-24个碳原子的脂环族醇和含有约7-12个碳原子的芳族醇,其中醇基不直接与芳族碳原子连接;
(B)异氰酸酯-活性组分,其包含:
(1)以(B)的100重量%为基准计,约70-90重量%的一种或多种聚醚多元醇,其官能度约为2-8(优选为2-4)、分子量约为1000-8000(优选为2000-6000),并且不含(伯、仲和/或叔)胺基;
(2)以(B)的100重量%为基准计,约10-30重量%的一种或多种有机化合物,其分子量约为62-400(优选为62-90),羟基官能度为2-3,并且不含(伯、仲和/或叔)胺基;
(C)一种或多种符合以下通式的催化剂:
式中:m表示3-8、优选3-4的整数;
n表示3-8、优选3-5的整数;
(D)一种或多种添加剂(包括紫外线稳定剂、颜料等)。
组分(A)和(B)的相对量使得所得弹性体的异氰酸酯指数约为100-120、优选为105-110。
在本发明的另一个实施方式中,脲基甲酸酯改性的多异氰酸酯可以进一步与官能度约为2-6、分子量约为60-4000的异氰酸酯-活性组分反应,形成预聚物。所得预聚物的NCO基团含量一般约为10-30重量%。这些脲基甲酸酯改性的脂(环)族多异氰酸酯的预聚物也可以用作依据本发明的组分(A)。
生产这些聚氨酯弹性体的方法包括通过反应注塑技术使反应混合物反应。该反应混合物如上所述。
发明详述
适用于本发明的多异氰酸酯包含(I)至少一种脲基甲酸酯改性的脂(环)族多异氰酸酯。本发明的多异氰酸酯还可以包括这些脲基甲酸酯改性的脂(环)族多异氰酸酯的预聚物。
适用于本发明的合适的脲基甲酸酯改性的多异氰酸酯的NCO基团含量通常约为15-35重量%,优选约为15-25重量%。这些脲基甲酸酯改性的多异氰酸酯包含(1)和(2)的反应产物:(1)NCO基团含量约为25-60重量%的脂(环)族多异氰酸酯;(2)选自脂族醇、脂环族醇和芳族醇的有机醇。
适合在制备本发明的脲基甲酸酯改性的多异氰酸酯(A)(1)中用作组分(1)的脂(环)族多异氰酸酯包括例如1,4-丁二异氰酸酯、1,6-己二异氰酸酯、2,2,4-三甲基-1,6-己二异氰酸酯、1,12-十二烷二异氰酸酯、环己烷-1,3-和-1,4-二异氰酸酯、1-异氰酸基-2-异氰酸甲酯基环戊烷、1-异氰酸基-3-异氰酸甲酯基-3,5,5-三甲基环己烷(即异佛尔酮二异氰酸酯或IPDI)、二-(4-异氰酸基环己基)甲烷,2,4′-二环己基甲烷二异氰酸酯、1,3-和1,4-二-(异氰酸甲酯基)环己烷、二-(4-异氰酸基-3-甲基环己基)甲烷、α,α,α′,α′-四甲基-1,3-和/或-1,4-苯二亚甲基二异氰酸酯,1-异氰酸基-1-甲基-4(3)-异氰酸甲酯基环己烷、二环己基甲烷-4,4’-二异氰酸酯、2,4-和/或2,6-六氢甲苯二异氰酸酯、和它们的混合物。优选异氰酸酯包括1,6-己二异氰酸酯、二环己基甲烷-4,4’-二异氰酸酯和1-异氰酸基-3-异氰酸甲酯基-3,5,5-三甲基环己烷。
合适的有机醇包括脂族醇、脂环族醇和芳族醇,其中醇基不直接与芳族碳原子连接。适合在制备脲基甲酸酯改性的多异氰酸酯中用作组分(2)的脂族醇包括那些含有约1-36个碳原子、优选约1-8个碳原子的脂族醇。合适的脂环族醇包括那些含有约5-24个碳原子、优选约6-10个碳原子的脂环族醇。合适的芳族醇包括那些含有约7-12个碳原子、优选约8-10个碳原子的芳族醇。在适用于本发明的芳族醇中,醇基不直接与芳族碳原子连接。
合适的有机醇的一些例子包括例如:脂族醇。例如甲醇、乙醇、丙醇、异丙醇、正丁醇、异丁醇、正戊醇、1-甲基丁醇、十六烷醇、2-甲氧基乙醇、2-溴-乙醇等;脂环族醇,例如环己醇、环戊醇、环庚醇、羟甲基环己醇等;其中醇基不直接与芳族碳原子连接的芳族醇例如苄醇、2-苯氧基乙醇、肉桂醇、对溴苄醇等。
1,6-己二异氰酸酯(HDI)的脲基甲酸酯改性的多异氰酸酯的NCO含量通常为15-45重量%,优选为20-30重量%。二环己基甲烷二异氰酸酯(rMDI)的脲基甲酸酯改性的多异氰酸酯的NCO含量通常为15-35重量%,优选为20-30重量%。异佛尔酮二异氰酸酯(IPDI)的脲基甲酸酯改性的多异氰酸酯的NCO含量通常为15-35重量%,优选为20-30重量%。
适用于本发明的脂(环)族多异氰酸酯的脲基甲酸酯改性的多异氰酸酯通过已知的方法制备。在约60-120℃的温度下,在脲基甲酸酯催化剂存在下,使脂(环)族多异氰酸酯与合适的有机醇反应,形成脲基甲酸酯改性的多异氰酸酯。合适的脲基甲酸酯催化剂包括例如乙酰丙酮锌、2-乙基己酸锌、环烷酸钴、亚油树脂酸铅(lead linoresinate)等。通常,这些催化剂被中和或通过加入催化剂终止剂终止以避免对随后的反应造成不利的影响。合适的催化剂终止剂包括酸性物质,例如无水盐酸、硫酸、二(2-乙基己基)磷酸氢酯、苯甲酰氯、路易斯(Lewis)酸等。终止剂通常以每摩尔脲基甲酸酯催化剂约2当量酸性终止剂的比例加入。
在本发明的另一个实施方式中,上述这些脲基甲酸酯改性的多异氰酸酯的预聚物也适合用作多异氰酸酯组分。这些预聚物的NCO基团含量通常约为10-35重量%,优选约为12-25重量%。而且,这些预聚物的官能度通常至少约为2。这些预聚物的官能度通常还不超过约6。本发明的脲基甲酸酯改性的多异氰酸酯的预聚物的制备包括使上述这些脲基甲酸酯改性的脂(环)族多异氰酸酯与合适的异氰酸酯-活性化合物反应,所述异氰酸酯-活性化合物例如聚醚多元醇、聚酯多元醇、或低分子量多元醇,包括二醇和三醇。适用于本发明的异氰酸酯-活性化合物的分子量通常约为60-4000,羟基官能度约为2-6。
依据本发明,适用于形成脲基甲酸酯改性的多异氰酸酯的预聚物的异氰酸酯-活性化合物的分子量通常至少约为60,优选至少约为75,更优选至少约为100,最优选至少约为130。这些异氰酸酯-活性化合物的分子量还通常小于或等于约4,000,优选小于或等于约1,000,更优选小于或等于约400,最优选小于或等于约200。可用于本发明的异氰酸酯-活性化合物的分子量可以在这些上限值和下限值的任意组合的范围内,包括这些上限值和下限值,例如约60-4,000,优选约75-1,000,更优选约100-400,最优选约130-200。
依据本发明,适用于形成脲基甲酸酯改性的多异氰酸酯的预聚物的异氰酸酯-活性化合物的羟基官能度通常至少约为2,并且通常小于或等于约6,优选小于或等于约4,更优选小于或等于约3。可用于本发明的异氰酸酯-活性化合物的羟基官能度可以在这些上限值和下限值的任何组合的范围内,包括这些上限值和下限值,例如约2-6,优选约2-4,更优选约2-3。
合适的异氰酸酯-活性化合物的例子包括聚醚多元醇、聚酯多元醇、低分子量多元醇,包括二醇、三醇等。显然,上述对分子量和官能度的限值适用于这些类型化合物中的每一种化合物。所有这些化合物都是聚氨酯化学领域中已知的。
合适的聚醚多元醇可通过合适的含有活性氢原子的起始化合物与环氧烷烃反应来制备,所述环氧烷烃例如环氧乙烷、环氧丙烷、环氧丁烷、氧化苯乙烯、四氢呋喃、表氯醇和它们的混合物。合适的含活性氢原子的起始化合物包括例如乙二醇、丙二醇、丁二醇、己二醇、辛二醇、新戊二醇、环己烷二甲醇、2-甲基-1,3-丙二醇、2,2,4-三甲基-1,3-戊二醇、三甘醇、四甘醇、聚乙二醇、双丙甘醇、聚丙二醇、二丁二醇、聚丁二醇、丙三醇、三羟甲基丙烷、季戊四醇、水、甲醇、乙醇、1,2,6-己三醇、1,2,4-丁三醇、三羟甲基乙烷、甘露醇、山梨糖醇、甲基葡糖苷、蔗糖、苯酚、间苯二酚、氢醌、1,1,1-或1,1,2-三-(羟基苯基)-乙烷等化合物。
合适聚酯多元醇包括例如多元醇(优选二元醇,任选地存在三元醇)和多元(优选二元)羧酸的反应产物。还可以不使用这些游离的多元羧酸,而使用相应的多元羧酸酐或相应的多元羧酸与低级醇的酯或它们的混合物来生产聚酯。多元羧酸可以是脂族、脂环族、芳族和/或杂环族多元羧酸,它们可以是不饱和的或者被例如卤原子取代。用于制备聚酯的多元羧酸和多元醇是已知的,在例如美国专利4,098,731和3,726,952中进行了描述,这些专利文献的全部内容通过参考结合于此。
在上述美国专利中还揭示了合适的聚硫醚、聚缩醛、聚碳酸酯和其它多羟基化合物。最后,可依据本发明使用的许多不同化合物的典型例子可见例如High Polymers,第XVI卷,″Polyurethanes,Chemistry and Technology,″Saunders-Frisch,Interscience Publishers,纽约,伦敦,第I卷,1962,第32-42页和第44-54页,和第II卷,1964,第5-6页和第198-199页;以及Kunststoff-Handbuch,第VII卷,Vieweg-Hochtlen,Carl Hanser Verlag,Munich,1966,第45-71页。
适用于制备预聚物的低分子量多元醇包括例如二醇、三醇、四醇和它们的低分子量烷氧基化产物。这些低分子量多元醇包括2-甲基-1,3-丙二醇、乙二醇、1,2-和1,3-丙二醇、1,3-和1,4-和2,3-丁二醇、1,6-己二醇、1,10-癸二醇、二甘醇、三甘醇、四甘醇、双丙甘醇、三丙二醇、丙三醇、三羟甲基丙烷、新戊二醇、环己烷二甲醇、2,2,4-三甲基戊烷-1,3-二醇、季戊四醇等。这些化合物的烷氧基化产物也可用于制备预聚物。依据本发明,优选的用于形成预聚物的异氰酸酯-活性化合物是三羟甲基丙烷和三丙二醇。
一类优选用于本发明的多异氰酸酯包括脲基甲酸酯改性的脂(环)族多异氰酸酯的预聚物。这些多异氰酸酯通过以下方法制备:首先形成如上所述的脲基甲酸酯改性的脂(环)族多异氰酸酯,然后使脲基甲酸酯改性的多异氰酸酯与合适的异氰酸酯-活性化合物反应,形成预聚物。该反应在聚氨酯化学领域中是众所周知的,可以通过例如以下方法进行:将反应物加热到约40℃至150℃、优选约50℃至100℃的温度,得到所需的预聚物。显然,使用相对于异氰酸酯-活性化合物过量的脲基甲酸酯改性的多异氰酸酯。
优选的依据本发明的脲基甲酸酯改性的多异氰酸酯包括那些选自下组的多异氰酸酯:1,6-己二异氰酸酯、异佛尔酮二异氰酸酯和二环己基甲烷二异氰酸酯。所得脲基甲酸酯改性的1,6-己二异氰酸酯的预聚物的NCO基团含量约为12-35,优选约为15-25,官能度约为2-6,优选约为2-3。所得脲基甲酸酯改性的异佛尔酮二异氰酸酯的预聚物的NCO基团含量约为10-35,优选约为15-25,官能度约为2-6,优选约为2-3。所得脲基甲酸酯改性的二环己基甲烷二异氰酸酯的预聚物的NCO基团含量约为10-35,优选约为15-25,官能度约为2-6,优选约为2-3。
依据本发明,在生产上述的一些异氰酸酯过程中本身产生的异氰酸酯残余物不适用于本发明的异氰酸酯组分。这些残余物是生产异氰酸酯组分过程中不希望有的副产物。
适合用作本发明的组分(B)(1)的化合物包括例如聚醚多元醇。适用于本发明的高分子量聚醚是已知的,可通过例如以下方法得到:四氢呋喃或环氧化物(例如环氧乙烷、环氧丙烷、环氧丁烷、氧化苯乙烯或表氯醇)在合适的催化剂(例如BF3或KOH)存在下进行聚合,或者将这些环氧化物(优选环氧乙烷和环氧丙烷)以混合物的形式,单独或相继地用化学方法加成到含活性氢原子的合适的起始化合物上。合适的起始化合物的例子包括但不限于丙二醇、丙三醇、乙二醇、丁二醇、二甘醇、三甘醇、双丙甘醇、三丙二醇、水、三羟甲基丙烷、四甘醇、季戊四醇、双酚A、蔗糖、山梨糖醇等。
本领域普通技术人员将认识到,这些类型的聚醚多元醇含有的不饱和度较高。
优选的聚醚包括例如那些基于二官能或三官能起始物的烷氧基化产物(优选环氧乙烷和/或环氧丙烷的),所述二官能或三官能起始物例如水、乙二醇、丙二醇、丙三醇、三羟甲基丙烷等。
适合用作本发明的(B)(1)的化合物包括那些分子量约为1,000-8,000、优选为2,000-约6,000,羟基官能度约为2-8、优选约为2-4的化合物。依据本发明,适用于本发明的组分(B)(1)的化合物不含伯胺、仲胺和/或叔胺基。
适合用作本发明的(B)(2)的化合物包括那些分子量约为62-400,羟基官能度约为2或3且不含伯胺、仲胺和/或叔胺基的化合物。这些化合物的分子量优选约为62-90。
适合用作本发明的组分(B)(2)的化合物的一些例子包括例如2-甲基-1,3-丙二醇、乙二醇、1,2-和1,3-丙二醇、1,3-和1,4-和2,3-丁二醇、1,6-己二醇、1,10-癸二醇、二甘醇、三甘醇、四甘醇、双丙甘醇、三丙二醇、四丙二醇、环己烷二甲醇和2,2,4-三甲基戊烷-1,3-二醇、三羟甲基丙烷、季戊四醇、丙三醇之类的化合物。优选的二醇包括例如乙二醇和三羟甲基丙烷。
依据本发明,组分(A)与组分(B)的反应在(C)符合以下通式的一种或多种催化剂存在下进行:
式中:
m表示3-8、优选3-4的整数;
n表示3-8、优选3-5的整数。
符合上述通式的合适的催化剂的一些例子包括1,8-二氮杂-7-二环[5.4.0]十一碳-7-烯(即DBU)、1,5-二氮杂二环[4.4.0]癸-5-烯(即DBD)、1,5-二氮杂二环[4.3.0]壬-5-烯(即DBN)、1,8-二氮杂二环[7.5.0]十四碳-8-烯、1,8-二氮杂二环[7.4.0]十三碳-8-烯、1,8-二氮杂二环[7.3.0]十二碳-8-烯等。
依据本发明,以组分(B)的100重量%为基准计,符合上述结构的催化剂的含量应该至少约为0.1-6.0重量%,优选约为0.5-2.5重量%,更优选约为1-1.5重量%。
依据本发明,还可以存在已知的适用于制备聚氨酯的其它催化剂。合适的催化剂包括例如已知的金属羧酸盐、金属卤化物、羧酸铵、锡-硫催化剂和叔胺催化剂。适用于这些催化剂的金属包括但不限于锡、铋、铅、汞等。在这些催化剂中,优选使用羧酸锡和/或叔胺与上述“二氮杂二环”催化剂的组合。
合适的金属羧酸盐包括:羧酸锡,例如二月桂酸二甲基锡、二月桂酸二丁基锡、二-2-乙基己酸二丁基锡、马来酸二丁基锡;羧酸铋,例如三新癸酸铋。一些合适的金属卤化物的例子包括例如卤化锡,特别是锡的氯化物,例如二氯化二甲基锡和二氯化二丁基锡。合适的羧酸铵的例子包括例如2-乙基己酸三甲基-羟乙基铵(即Dabco TMR)。如上所述,二月桂酸二甲基锡和二月桂酸二丁基锡之类的羧酸锡是优选与上述特定通式的催化剂联合使用的金属羧酸盐催化剂。其它合适的催化剂包括锡-硫催化剂,例如二月桂基硫醇二烷基锡,例如二月桂基硫醇二丁基锡和二月桂基硫醇二甲基锡。合适的叔胺催化剂的一些例子包括三乙胺、三亚乙基二胺、三丁胺、N-甲基吗啉、N-乙基吗啉、三乙醇胺、三异丙醇胺、N-甲基二乙醇胺、N-乙基二乙醇胺和N,N-二甲基乙醇胺之类的化合物。
依据本发明的优选实施方式,优选使用符合上述通式的催化剂和一种或多种羧酸锡催化剂的组合。优选的羧酸锡包括二月桂酸二甲基锡和/或二月桂酸二丁基锡。
当依据本发明的优选实施方式使用两种或多种催化剂的组合时,催化剂的总量通常应该落在之前所述的数量范围内。换句话说,以组分(B)的100重量%为基准计,所有催化剂的总量应该至少约为0.1-6.0重量%、优选约为0.5-2.5重量%,更优选约为1-1.5重量%。如果具有符合上述通式的结构的胺催化剂与羧酸锡催化剂的优选组合用于本发明,则优选(上述结构的)胺催化剂的含量为50-90重量%,羧酸锡催化剂的含量为10-50重量%,这些重量百分数之和等于催化剂组分的100重量%。更具体地,通常使符合特定通式的胺催化剂占0.1-6.0重量%的全部催化剂的50-90重量%;而羧酸锡催化剂占0.1-6.0重量%的全部催化剂的约10-50重量%,各催化剂的重量百分数之和等于催化剂的100重量%。
适用于本发明的稳定剂包括光稳定剂,该光稳定剂考虑包括能够防止本发明的弹性体发生明显的泛黄现象的任何已知组合物。本发明中使用的光稳定剂可以理解为包括位阻胺光稳定剂、紫外线(UV)吸收剂和/或抗氧化剂。
位阻胺光稳定剂的一些例子包括但不限于例如那些由2,2,6,6-四烷基哌啶部分得到的化合物,其它类型的位阻胺,例如那些含有吗啉酮、哌嗪酮、哌嗪二酮、噁唑烷、咪唑啉等的位阻胺。合适的位阻胺光稳定剂的具体例子包括例如,但不限于:二(2,2,6,6-四甲基-4-哌啶基)癸二酸酯、二(1,2,2,6,6-五甲基-4-哌啶基)癸二酸酯、2-甲基-2-(2,2,6,6-四甲基-4-哌啶基)氨基-N-(2,2,6,6-四甲基-4-哌啶基)丙酰胺、2-(3,5-二叔丁基-4-羟基苄基)-2-正丁基丙二酸二(1,2,2,6,6-五甲基-4-哌啶基)酯、1,2,3,4-丁烷四羧酸四(2,2,6,6-四甲基-4-哌啶基)酯、聚[{6-(1,1,3,3-四甲基丁基)亚氨基-1,3,5-三嗪-2,4-二基}{(2,2,6,6-四甲基-4-哌啶基)亚氨基}六亚甲基-{(2,2,6,6-四甲基-4-哌啶基)亚氨基}]、聚[(6-吗啉代-1,3,5-三嗪-2,4-二基){(2,2,6,6-四甲基-4-哌啶基)亚氨基}六亚甲基{(2,2,6,6-四甲基-4-哌啶基)亚氨基}]、琥珀酸二甲酯和1-(2-羟乙基)-4-羟基-2,2,6,6-四甲基哌啶的缩聚物、N,N-二(3-氨基丙基)乙二胺和2,4-二[N-丁基-N-(1,2,2,6,6-五甲基-4-哌啶基)氨基]-6-氯-1,3,5-三嗪的缩聚物、1,2,2,6,6-五甲基-4-哌啶醇(piperidinol)和3,9-二(2-羟基-1,1-二甲基乙基)-2,4,8,10-四氧杂螺[5.5]十一烷与1,2,3,4-丁烷四羧酸和二(1-辛氧基-2,2,6,6-四甲基-4-哌啶基)癸二酸酯的缩聚物。
苯并呋喃酮(benzofranone)稳定剂包括例如5,7-二叔丁基-3-(3,4-二甲基苯基)-3H-苯并呋喃-2-酮等的化合物。氨基脲稳定剂包括例如1,6-六亚甲基二(N,N-二甲基氨基脲)、4,4′-(亚甲基二-对-亚苯基)二(N,N-二乙基氨基脲)、4,4′-(亚甲基二-对-亚苯基)二(N,N-二乙基氨基脲)、4,4′-(亚甲基二-对-亚苯基)二(N,N-二异丙基氨基脲)、α,α-(对-苯二亚甲基)-二(N,N-二甲基氨基脲)、1,4-亚环己基二(N,N-二甲基氨基脲)等。
适用于本发明的紫外线(UV)稳定剂包括以下化合物,例如2-(3-叔丁基-2-羟基-5-甲基-苯基)-5-氯苯并三唑、2-(3,5-二叔丁基-2-羟基苯基)-苯并三唑、2-(2-羟基-5-甲基苯基)苯并三唑、2-(2-羟基-5-叔辛基苯基)苯并三唑、2-(3,5-二叔戊基-2-羟基苯基)-苯并三唑、2-[2-羟基-3,5-二(α,α-二甲基苄基)苯基]苯并三唑、2-羟基-4-辛氧基二苯甲酮、2-羟基-4-甲氧基二苯甲酮、2,4-二叔丁基苯基-3,5-二叔丁基-4-羟基苯甲酸酯、3,5-二叔丁基-4-羟基苯甲酸正十六烷酯、2-氰基-3,3-二苯基丙烯酸乙酯、2,4-二羟基二苯甲酮、2,2′,4,4′-四羟基-二苯甲酮、2-(2-羟基-4-辛氧基苯基)苯并三唑、2-[2-羟基-3,5-二(α,α-二甲基苄基)苯基]-2H-苯并三唑、2-(3,5-二叔丁基-2-羟基苯基)-5-氯苯并三唑、3-[3-叔丁基-5-(2H-苯并三唑-2-基)-4-羟基苯基]丙酸甲酯和聚乙二醇(分子量:约300)的缩合物、羟基苯基-苯并三唑衍生物、2-(4,6-二苯基-1,3,5-三嗪-2-基)-5-己氧基苯酚和2-[4,6-二(2,4-二甲基苯基)-1,3,5-三嗪-2-基]-5-辛氧基苯酚等,以及它们的混合物。
可用于本发明的合适的抗氧化剂的一些例子包括以下化合物,例如3,5-二叔丁基-4-羟基氢化肉桂酸正十八烷酯;四(3,5-二叔丁基-4-羟基氢化肉桂酸)新戊四基(neopentanetetrayl)酯;3,5-二叔丁基-4-羟基苄基-膦酸二(正十八烷基)酯;1,3,5-三(3,5-二叔丁基-4-羟基苄基)异氰脲酸酯;1,3,5-三甲基-2,4,6-三(3,5-二叔丁基-4-羟基苄基)苯;二(3-甲基-5-叔丁基-4-羟基氢化肉桂酸)3,6-二氧杂八亚甲基酯;2,2′-亚乙基(ethylidene)-二(4,6-二叔丁基苯酚);1,3,5-三(2,6-二甲基-4-叔丁基-3-羟基苄基)异氰脲酸酯;1,1,3,-三(2-甲基-4-羟基-5-叔丁基苯基)丁烷;1,3,5-三[2-(3,5-二叔丁基-4-羟基氢化肉桂酰氧基(hydrocinnamoyloxy))乙基]异氰脲酸酯;3,5-二-(3,5-二叔丁基-4-羟基-苄基)(2,4,6-三甲基苯酚)(mesitol);1-(3,5-二叔丁基-4-羟基苯胺基)-3,5-二(辛硫基)-s-三嗪;N,N′-六亚甲基-二(3,5-二叔丁基-4-羟基氢化肉桂酰胺);二[3,3-二(3-叔丁基-4-羟基苯基)丁酸亚乙酯;二(3,5-二叔丁基-4-羟基氢化肉桂酰基)酰肼;N,N-二-(C12-C24烷基)-N-甲基-胺氧化物;等等。可用作本发明的抗氧化剂的其它合适的化合物包括烷基化单苯酚,例如2,6-二叔丁基-4-甲基苯酚、2-叔丁基-4,6-二甲基苯酚、2,6-二环戊基-4-甲基苯酚、2,6-二(十八烷基)-4-甲基苯酚、2,4,6-三环己基苯酚、2,6-二叔丁基-4-甲氧基甲基苯酚等等;烷基化的氢醌,例如2,6-二叔丁基-4-甲氧基苯酚、2,5-二叔丁基-氢醌、2,5-二叔戊基氢醌、2,6-二苯基-4-十八烷氧基苯酚等;羟基化的硫代二苯基醚,例如2,2′-硫代-二(6-叔丁基-4-甲基苯酚)、2,2′-硫代-二(4-辛基苯酚)、4,4′-硫代-二(6-叔丁基-2-甲基苯酚)等;亚烷基(alkylidene)-双酚,例如2,2′-亚甲基-二(6-叔丁基-4-甲基苯酚)、2,2′-亚甲基-二(4-甲基-6-环己基苯酚)、2,2′-亚甲基-二(6-壬基-4-甲基苯酚)、2,2′-亚甲基-二[6-(α-甲基苄基)-4-壬基苯酚]、2,2′-亚甲基-二[6-(α,α-二甲基苄基)-4-壬基苯酚]、4,4′-亚甲基-二(2,6-二叔丁基-苯酚)、2,6-二(3-叔丁基-5-甲基-2-羟基苄基)-4-甲基苯酚、1,1,3-三(5-叔丁基-4-羟基-2-甲基苯基)丁烷、二(3-叔丁基-4-羟基-5-甲基苯基)二环戊二烯、二[2-(3′-叔丁基-2′-羟基-5′-甲基苄基)-6-叔丁基-4-乙基苯基]对苯二甲酸酯等;苄基化合物,例如1,3,5-三(3,5-二叔丁基-4-羟基苄基)-2,4,6-三甲基苯、二(3,5-二叔丁基-4-羟基苄基)硫醚、二(4-叔丁基-3-羟基-2,6-二甲基苄基)-二硫醇对苯二甲酸酯等;酰基氨基苯酚,例如4-羟基-N-月桂酰苯胺(4-hydroxy-lauric acidanilide)、4-羟基-N-硬脂酰苯胺(4-hydroxy-stearic acid anillide)、2,4-二-辛基巯基-6-(3,5-叔丁基-4-羟基苯胺基)-s-三嗪等;β-(3,5-二叔丁基-4-羟基苯基)丙酸的酰胺,例如N,N′-二(3,5-二叔丁基-4-羟基苯基丙酰基)六亚甲基二胺等;二芳基胺,例如二苯胺、N-苯基-1-萘胺、N-(4-叔辛基苯基)-1-萘胺等。
依据本发明,可以含有一种或多种颜料和/或染料,包括有机和无机化合物。合适的无机颜料包括,例如:氧化物颜料,诸如铁氧化物、二氧化钛、镍氧化物、铬氧化物和钴蓝、以及锌硫化物、群青、稀土族的硫化物、钒酸铋、以及被认为对本发明来说是颜料的炭黑。具体的炭黑是通过气体或炉法得到的酸性至碱性炭黑,以及化学表面改性的炭黑,例如含磺基(sulfo)或羧基的炭黑。合适的有机颜料包括例如单偶氮、双偶氮、色淀偶氮(1aked azo)、β-萘酚、萘酚AS(Naphthol AS)、苯并咪唑酮、重氮缩合物、偶氮金属配合物、异吲哚啉酮和异吲哚啉系列、以及例如来自酞菁、喹吖啶酮、苝、索兰士林(perinone)、硫靛、蒽醌、二噁嗪、喹酞酮和二酮基吡咯并吡咯系列的多环颜料。合适的颜料还包括上述颜料的固溶体,有机和/或无机颜料与有机和/或无机颜料的混合物,例如炭黑涂布的金属、云母或滑石颜料,例如CVD涂布了氧化铁的云母,以及上述颜料相互形成的混合物。其它合适的颜料包括色淀染料,诸如含有磺基和/或羧基的染料的Ca、Mg和Al色淀。也合适的是已知的来自偶氮金属配合物颜料或它们的互变异构形式的颜料。其它合适的颜料包括,例如,铝、锌或镁的金属薄片颜料。也可能金属薄片,特别是铝薄片也许是叶状或非叶状的。
可用于本发明的其它合适的添加剂包括表面活性添加剂,例如乳化剂和泡沫稳定剂。例子包括N-硬脂基-N′,N′-二-羟乙基脲、油基聚氧乙烯酰胺、硬脂基二乙醇酰胺、异硬脂基二乙醇酰胺、聚氧乙烯二醇单油酸酯、季戊四醇/己二酸/油酸酯、油酸的羟基乙基咪唑衍生物、N-硬脂基丙二胺、蓖麻油磺酸酯的钠盐或脂肪酸的钠盐。磺酸如十二烷基苯磺酸或二萘基甲磺酸以及脂肪酸的碱金属盐或铵盐也可用作表面活性添加剂。
合适的泡沫稳定剂包括水溶性聚醚硅氧烷。这些化合物的结构通常使得环氧乙烷和环氧丙烷的共聚物被连接在聚二甲基硅氧烷基上。例如,在美国专利2,764,565中描述了这类泡沫稳定剂。除了泡沫稳定剂和表面活性剂外,可用于本发明的模塑组合物的其它添加剂包括已知的包含氮的发泡剂、泡孔调节剂、阻燃剂、增塑剂、增粘剂、填料和增强剂,例如纤维或薄片形式的玻璃或碳纤维。
还可以在本发明的RIM方法中使用已知的内脱模剂,例如硬脂酸锌。如本领域普通技术人员所知,在RIM方法中,将异氰酸酯和含活性氢的化合物混合,然后注入到模具中,在该模具中使反应物完全反应。
本发明的模塑产品通过RIM方法使组分在闭合模具中反应来制备。可使用常规加工技术在异氰酸酯指数约为90-120(优选100-110)的情况下对本发明的组合物进行模塑。术语“异氰酸酯指数(通常也称为NCO指数)”在本文中定义为异氰酸酯的当量数除以含异氰酸酯-活性氢的物质的总当量数再乘以100。
通常,在RIM方法中,将两个独立的物流充分混合,然后注入合适的模具中,但是可以使用超过两个的物流。第一物流含有多异氰酸酯组分,而第二物流含有异氰酸酯-活性组分和要包含的任何其它添加剂。
以下实施例进一步详细说明本发明组合物的制备和应用。在上文中陈述的本发明的精神或范围不受这些实施例的限制。本领域技术人员容易理解,可用以下制备步骤的条件和过程的已知变化来制备这些组合物。除非另有说明,所有温度是℃,所有份数和百分数分别是重量份数和重量百分数。
实施例
以下组分用在本申请的实施例中:
异氰酸酯A:通过使3148克(28.3当量)IPDI与172克(2.3当量)异丁醇反应来制备基于IPDI和异丁醇的脲基甲酸酯。所得脲基甲酸酯的NCO含量为30.1%。然后,通过向上述脲基甲酸酯中加入196克(2.0当量)三羟甲基丙烷来制备脲基甲酸酯的预聚物。所得预聚物的NCO含量为25.9重量%。
多元醇A:聚醚多元醇,其标称官能度约为3,OH值约为28,分子量约为6000,包含丙三醇与环氧丙烷的反应产物,用环氧乙烷封端,在KOH催化剂存在下制得。
EG:乙二醇
催化剂A:二月桂酸二甲基锡催化剂,可以Fomrez UL-28从通用有机硅公司(GE Silicones)购得
催化剂B:1,8-二氮杂(diazo)二环(5.4.0)十一碳-7-烯,可以Polycat DBU从空气产品(Air Products)公司购得
表面活性剂A:硅氧烷表面活性剂,可以Niax L-1000从通用有机硅公司(GE Silicones)购得
颜料A:炭黑多元醇分散体颜料,可以Colormatch DR-20845从塑料颜色公司(Plasticolors Corp)购得
紫外稳定剂:紫外线稳定剂的组合,可以Tinuvin B 75从汽巴公司(CibaCorp.)购得
一般步骤:
使用上述各组分生产反应注塑制品。使用的具体材料和各材料的量示于下表1中。
使用小型RIM(MiniRIM)圆柱形机器对实施例1-2的聚氨酯形成体系进行注塑。将异氰酸酯-活性物质和各种添加剂放入到机器的B部分中,将适量的异氰酸酯组分装入到A部分中。对小型RIM装配亨尼克(Hennecke)mq8混合头。将B部分预热到90°F,将A部分加热到90°F。将物料以约200巴的注射压力和400克/秒的注射速率注入。将物料注入到加热到约165°F的3×200×300毫米的平板模具中。在60秒保压时间(dwell time)后,将部件脱模。依据ASTM标准测定物理性能。
在本申请的工作实施例中使用以下ASTM测试方法。
表1:实施例1-2的配方
配方 | 实施例1 | 实施例2 |
多元醇A | 80 | 88 |
EG | 20 | 12 |
催化剂A | 1 | 1 |
催化剂B | 2 | 2 |
表面活性剂A | 1 | 1 |
紫外稳定剂 | 5 | 5 |
颜料A | 5 | 5 |
Iso A | 116.8 | 736 |
异氰酸酯指数 | 105 | 105 |
凝胶时间(秒) | 4 | 8 |
注射时间(秒) | 1 | 1 |
脱模时间(秒) | 5 | 5 |
板密度(pcf) | 68 | 68 |
样品数 | 6 | 6 |
表2:实施例1-2的性能:
性能 | 实施例1 | 实施例2 |
密度(pcf) | 61.8 | 66.35 |
挠曲模量(psi) | 25,750 | 3,906 |
硬度-肖氏A@1秒 | 96 | 87 |
硬度-肖氏D@1秒 | 55 | 36 |
撕裂强度-冲模C(pli) | 433.1 | 352.8 |
拉伸强度(psi) | 2387 | 1956 |
伸长(%) | 259.1 | 366.3 |
虽然在前文中为了说明起见对本发明进行了详细的描述,但应理解,这些详细描述仅仅是为了说明,在不偏离本发明的精神和范围的情况下本领域技术人员可对其进行修改,本发明仅由权利要求书限定。
Claims (20)
1.一种生产聚氨酯弹性体的方法,该方法包括通过反应注塑技术使反应混合物反应,所述反应混合物包含:(A)与(B),并且存在(C)和任选的(D):
(A)多异氰酸酯组分,其包含(I)NCO基团含量约为15-35重量%的脲基甲酸酯改性的多异氰酸酯,其包含(1)和(2)的反应产物:
(1)NCO基团含量约为25-60%的脂(环)族多异氰酸酯,
(2)选自下组的有机醇:含有1-36个碳原子的脂族醇、含有5-24个碳原子的脂环族醇和含有约7-12个碳原子的芳族醇,其中醇基不直接与芳族碳原子连接;
(B)异氰酸酯-活性组分,其包含:
(1)以(B)的100重量%为基准计,约70-90重量%的一种或多种聚醚多元醇,其官能度约为2-8,分子量约为1000-8000,并且不含胺基;
(2)以(B)的100重量%为基准计,约10-30重量%的一种或多种有机化合物,其分子量约为62-400,羟基官能度为2-3,并且不含胺基;
(C)一种或多种符合以下通式的催化剂:
式中:m表示3-8的整数;
n表示3-8的整数;
(D)一种或多种添加剂;
其中组分(A)和(B)的相对量使得异氰酸酯指数约为90-120。
2.如权利要求1所述的方法,其特征在于,(A)所述多异氰酸酯组分包含一种预聚物,该预聚物包含(I)与(II)的反应产物:
(I)脲基甲酸酯改性的多异氰酸酯,其NCO基团含量约为15-35重量%,
(II)异氰酸酯-活性组分,其官能度约为2-6,分子量约为60-4000,
其中所得预聚物的NCO基团含量约为10%-35%。
3.如权利要求1所述的方法,其特征在于,所述脂(环)族多异氰酸酯选自下组:1-异氰酸基-3-异氰酸甲酯基-3,5,5-三甲基环己烷、二环己基甲烷-4,4’-二异氰酸酯和1,6-己二异氰酸酯。
4.如权利要求2所述的方法,其特征在于,所述脂(环)族多异氰酸酯选自下组:1-异氰酸基-3-异氰酸甲酯基-3,5,5-三甲基环己烷、二环己基甲烷-4,4’-二异氰酸酯和1,6-己二异氰酸酯。
5.如权利要求1所述的方法,其特征在于,(B)(1)的官能度为2-4,分子量为2000-6000。
6.如权利要求1所述的方法,其特征在于,(B)(2)的分子量为62-90。
7.如权利要求1所述的方法,其特征在于,(C)包含1,8-二氮杂二环(5.4.0)十一碳-7-烯。
8.如权利要求1所述的方法,其特征在于,(C)还包含锡催化剂。
9.如权利要求1所述的方法,其特征在于,(D)所述一种或多种添加剂包含一种或多种选自下组的稳定剂:抗氧化剂、位阻胺光稳定剂和紫外线稳定剂。
10.如权利要求1所述的方法,其特征在于,(D)所述一种或多种添加剂包含一种或多种颜料和/或染料。
11.一种聚氨酯弹性体,其包含(A)与(B)在(C)和任选的(D)存在下的反应产物:
(A)多异氰酸酯组分,其包含(I)NCO基团含量约为15-35重量%的脲基甲酸酯改性的多异氰酸酯,其包含(1)和(2)的反应产物:
(1)NCO基团含量约为25-60%的脂(环)族多异氰酸酯,
(2)选自下组的有机醇:含有1-36个碳原子的脂族醇、含有5-24个碳原子的脂环族醇和含有约7-12个碳原子的芳族醇,其中醇基不直接与芳族碳原子连接;
(B)异氰酸酯-活性组分,其包含:
(1)以(B)的100重量%为基准计,约70-90重量%的一种或多种聚醚多元醇,其官能度约为2-8,分子量约为1000-8000,且不含胺基;
(2)以(B)的100重量%为基准计,约10-30重量%的一种或多种有机化合物,其分子量约为62-400,羟基官能度为2-3,并且不含胺基;
(C)一种或多种符合以下通式的催化剂:
式中:m表示3-8的整数;
n表示3-8的整数;
(D)一种或多种添加剂;
其中组分(A)和(B)的相对量使得异氰酸酯指数约为90-120。
12.如权利要求11所述的弹性体,其特征在于,(A)所述多异氰酸酯组分包含一种预聚物,该预聚物包含(I)与(II)的反应产物:
(I)脲基甲酸酯改性的多异氰酸酯,其NCO基团含量约为15-35重量%,
(II)异氰酸酯-活性组分,其官能度约为2-6,分子量约为60-4000,
其中所得预聚物的NCO基团含量约为10%-35%。
13.如权利要求11所述的弹性体,其特征在于,所述脂(环)族多异氰酸酯选自下组:1-异氰酸基-3-异氰酸甲酯基-3,5,5-三甲基环己烷、二环己基甲烷-4,4’-二异氰酸酯和1,6-己二异氰酸酯。
14.如权利要求12所述的弹性体,其特征在于,所述脂(环)族多异氰酸酯选自下组:1-异氰酸基-3-异氰酸甲酯基-3,5,5-三甲基环己烷、二环己基甲烷-4,4’-二异氰酸酯和1,6-己二异氰酸酯。
15.如权利要求11所述的弹性体,其特征在于,(B)(1)的官能度为2-4,分子量为2000-6000。
16.如权利要求11所述的弹性体,其特征在于,(B)(2)的分子量为62-90。
17.如权利要求11所述的弹性体,其特征在于,(C)包含1,8-二氮杂二环(5.4.0)十一碳-7-烯。
18.如权利要求11所述的弹性体,其特征在于,(C)还包含锡催化剂。
19.如权利要求11所述的弹性体,其特征在于,(D)所述一种或多种添加剂包含一种或多种选自下组的稳定剂:抗氧化剂、位阻胺光稳定剂和紫外线稳定剂。
20.如权利要求11所述的弹性体,其特征在于,(D)所述一种或多种添加剂包含一种或多种颜料和/或染料。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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US11/350,316 US20070185302A1 (en) | 2006-02-08 | 2006-02-08 | Polyurethane elastomers comprising allophanate modified isocyanates |
US11/350,316 | 2006-02-08 |
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US (1) | US20070185302A1 (zh) |
EP (1) | EP1984418A2 (zh) |
JP (1) | JP2009526122A (zh) |
KR (1) | KR20080100428A (zh) |
CN (1) | CN101410431A (zh) |
BR (1) | BRPI0707555A2 (zh) |
CA (1) | CA2641427A1 (zh) |
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CN111303373A (zh) * | 2020-02-25 | 2020-06-19 | 万华化学集团股份有限公司 | 一种低色度脲基甲酸酯组合物及其制备方法和应用 |
CN114369189A (zh) * | 2021-12-27 | 2022-04-19 | 万华化学集团股份有限公司 | 一种脱卤剂、制备甲苯二异氰酸酯和甲苯二异氰酸酯三聚体的方法 |
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US20070142610A1 (en) * | 2005-12-15 | 2007-06-21 | Harasin Stephen J | Polyurethane elastomers comprising allophanate modified isocyanates |
US8468968B2 (en) | 2009-10-22 | 2013-06-25 | Quest Inspar LLC | Method and apparatus for lining pipes with isocyanate and hydroxyl-amine resin based on castrol or soy oil |
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US4218543A (en) * | 1976-05-21 | 1980-08-19 | Bayer Aktiengesellschaft | Rim process for the production of elastic moldings |
US4269945A (en) * | 1980-01-24 | 1981-05-26 | The Dow Chemical Company | Reaction injection molded polyurethanes employing aliphatic amine chain extenders |
US4642320A (en) * | 1983-11-02 | 1987-02-10 | The Dow Chemical Company | Reaction injection molded polyureas employing high molecular weight amine-terminated polyethers |
EP0275010B1 (de) * | 1987-01-14 | 1991-11-21 | Bayer Ag | Verfahren zur Herstellung von Polyurethan-Formteilen |
US4764543A (en) * | 1987-08-03 | 1988-08-16 | The Dow Chemical Company | Microcellular foamed or reaction injection molded polyurethane/polyureas employing amine terminated polymers and diamine chain extenders |
GB9125918D0 (en) * | 1991-12-05 | 1992-02-05 | Ici Plc | Reaction system for preparing polyurethane/polyurea |
US5502147A (en) * | 1993-12-21 | 1996-03-26 | Bayer Corporation | Aliphatic rim elastomers |
US5502150A (en) * | 1994-06-29 | 1996-03-26 | Bayer Corporation | Linear HDI urethane prepolymers for rim application |
CA2174305C (en) * | 1995-06-07 | 2007-07-03 | Ronald A. Cageao | Method of producing gaskets from polyurethane/urea compositions and gaskets produced therefrom |
IN1997CH00157A (zh) * | 1996-10-01 | 2006-06-09 | Recticel | |
US20070142610A1 (en) * | 2005-12-15 | 2007-06-21 | Harasin Stephen J | Polyurethane elastomers comprising allophanate modified isocyanates |
-
2006
- 2006-02-08 US US11/350,316 patent/US20070185302A1/en not_active Abandoned
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2007
- 2007-02-05 EP EP07763413A patent/EP1984418A2/en not_active Withdrawn
- 2007-02-05 RU RU2008131912/04A patent/RU2008131912A/ru not_active Application Discontinuation
- 2007-02-05 CN CNA2007800045212A patent/CN101410431A/zh active Pending
- 2007-02-05 BR BRPI0707555-3A patent/BRPI0707555A2/pt not_active Application Discontinuation
- 2007-02-05 CA CA002641427A patent/CA2641427A1/en not_active Abandoned
- 2007-02-05 JP JP2008554305A patent/JP2009526122A/ja not_active Withdrawn
- 2007-02-05 KR KR1020087019352A patent/KR20080100428A/ko not_active Application Discontinuation
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CN111303373A (zh) * | 2020-02-25 | 2020-06-19 | 万华化学集团股份有限公司 | 一种低色度脲基甲酸酯组合物及其制备方法和应用 |
CN114369189A (zh) * | 2021-12-27 | 2022-04-19 | 万华化学集团股份有限公司 | 一种脱卤剂、制备甲苯二异氰酸酯和甲苯二异氰酸酯三聚体的方法 |
CN114369189B (zh) * | 2021-12-27 | 2023-12-19 | 万华化学集团股份有限公司 | 一种脱卤剂、制备甲苯二异氰酸酯和甲苯二异氰酸酯三聚体的方法 |
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WO2007092459A3 (en) | 2008-08-28 |
JP2009526122A (ja) | 2009-07-16 |
RU2008131912A (ru) | 2010-03-20 |
KR20080100428A (ko) | 2008-11-18 |
WO2007092459A2 (en) | 2007-08-16 |
CA2641427A1 (en) | 2007-08-16 |
US20070185302A1 (en) | 2007-08-09 |
BRPI0707555A2 (pt) | 2011-05-10 |
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