CN100349902C - 含异氰酸酯基团的硅烷的制备方法 - Google Patents
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Abstract
本发明公开了一种主要应用于高档聚氨酯密封胶以及改性聚氨酯树脂的含异氰酸酯基团的硅烷的制备方法,主要包括如步骤:(1)采用氨基硅烷和碳酸酯为原料,在碱性催化剂作用下反应生成含硅基有机氨基甲酸酯的混合物;(2)然后用中和试剂中和上述的反应混合物;(3)将上述混合物过滤后,得到含硅基有机氨基甲酸酯的清液;(4)最后对上述的清液进行减压精馏裂解,制得含异氰酸酯基团的硅烷。本发明的优点是:工艺路线简单,原料价廉易得,毒性低;同时少量固体盐形成,基本对环境没有什么污染。产品含异氰酸酯基团的硅烷的纯度大于98%,收率在90%以上,反应选择性高,达97%以上。
Description
技术领域
本发明涉及到一种含异氰酸酯基团的硅烷的制备方法。
背景技术
含异氰酸酯基团的硅烷主要应用于高档聚氨酯密封胶以及改性聚氨酯树脂等。对含异氰酸酯基团的硅烷的合成研究中,主要采取氯硅烷和异氰酸钠或者钾盐在醇溶剂存在下,反应生成含异氰酸酯基团的硅烷,或者直接采用硅氢化合物与不饱和异氰酸酯,在贵金属铂、钯等催化剂作用下合成含异氰酸酯基团硅烷。这两种方法都存在原材料稀少并且价格昂贵,同时如异氰酸钠或者钾盐原料属巨毒原料,因而给研究或者生产带来诸多不便。
发明内容
本发明针对上述技术缺陷,提出适合于生产含异氰酸酯基团的硅烷的一种新工艺方法。
本发明所述方法的主要原理如下:
将氨基硅烷慢慢加入到碳酸酯中,搅拌下进行化学反应,静置,加入中和试剂中和,过滤分盐,得到无色清液。对此无色清液减压精馏,收集130~140℃/1~10kPa的馏分,经过FR-IR红外光谱仪器分析,在2210~2267cm-1出现强而尖吸收峰,经过确定是O=C=N-基团吸收峰。
本发明采用的主要步骤为:
(1)采用氨基硅烷和碳酸酯为原料,在碱性催化剂作用下反应生成含硅基有机氨基甲酸酯的混合物;
(2)然后用中和试剂中和上述的反应混合物;
(3)将上述混合物过滤后,得到含硅基有机氨基甲酸酯的清液;
(4)最后对上述的清液进行减压精馏裂解,制得含异氰酸酯基团的硅烷。
上述反应物中,氨基硅烷与碳酸酯的摩尔比为1∶10~10∶1。
上述的氨基硅烷为如下结构式表示:
NH2RSiX(3-a)R1 a
上式中,R为饱和烷基,其碳链长度为C1~C12;R1为烷基,其碳链长度为C1~C12,或为芳基或芳烷基;a为0~3整数;X为烷氧基基团、烷基硅氧基基团或者烷氧基取代的烷氧基基团。
上述的碳酸酯为如下结构式表示:
R2是相同的或者不相同的烷基基团或芳基基团,烷基基团碳链长度有C1~C12;芳基基团碳链长度有C6~C12;R’为氢或烷基基团,其中,烷基基团碳链长度为C1~C12;R”为氢或烷基基团,其中,烷基基团碳链长度为C1~C12。
上述的碱性催化剂为M(OR3)y,其中,M为碱金属——如Na、K等、碱土金属——如镁、钙等、第三主族元素——如铝等、或者过渡金属——如钛、锆等;R3为不同或者相同的烷基基团,其碳链长度为C1~C10;y为1~4的整数。并且催化剂的用量占反应物总重量的0~6%,但不为0。
上述的中和试剂为盐酸、磷酸、冰乙酸、丙酸、丁酸、己酸、油酸、马来酸、富马酸或琥珀酸中的一种。
另外,本发明所述的硅基有机氨基甲酸酯为如下结构式表示:
其中:R为饱和烷基,其碳链长度为C1~C12;R2为烷基基团,其碳链长度为C1~C12;或是芳基基团,其碳链长度有C6~C12;R1为烷基基团,其碳链长度为C1~C12;或是芳基基团或芳烷基基团;X为烷氧基基团、烷基硅氧基基团或烷氧基取代的烷氧基基团;a为0~3的整数。
本发明所述的含异氰酸酯基团的硅烷可用如下结构式表示:
其中:R为饱和烷基,其碳链长度为C1~C12;R1为烷基基团,其碳链长度为C1~C12;或是芳基基团或芳烷基基团;X为烷氧基基团、烷基硅氧基基团或烷氧基取代的烷氧基基团;a为0~3的整数。
本发明的优点是:工艺路线简单,原料价廉易得,同时少量固体盐形成,基本对环境没有什么污染。产品含异氰酸酯基团的硅烷的纯度大于98%,收率在90%以上,反应选择性高,达97%以上。
实施例
下面利用实施例对本发明作进一步的描述。
例一
在盛有碳酸二甲酯108g的三口烧瓶中,搅拌下加入催化剂甲醇钠7g,在室温下滴加氨丙基三甲氧基硅烷180g,滴加时间为1小时,保温3小时。取样测定总碱度0.05mol/g,并通过计算加入冰乙酸0.84g中和催化剂以及未反应的氨丙基三甲氧基硅烷。过滤得到滤液,减压精馏收集130℃/20mmHg馏分192g,通过GC-14C检测,纯度大于98%,收率95.5%。通过红外光谱分析,在2210~2276cm-1有强而尖吸收峰,证明为N=C=O基团特征吸收峰。
例二
在盛有碳酸丙烯酯158g的三口烧瓶中,搅拌下加入催化剂乙醇镁9.2g,在室温下滴加氨丙基三乙氧基硅烷221g,滴加时间为1小时,于50℃保温3小时。取样测定总碱度0.08,并通过计算加入冰乙酸1.35g中和催化剂以及未反应的氨丙基三乙氧基硅烷。过滤得到滤液,减压精馏收集130~140℃/1~10kPa馏分230g,通过GC-14C检测,纯度98.5%,收率93.1%,通过红外光谱分析,在2276cm-1有强而尖吸收峰,证明为N=C=O基团特征吸收峰。
例三
在盛有碳酸乙烯酯100g的三口烧瓶中,搅拌下加入催化剂乙醇铝7.8g,在室温下滴加氨丙基三乙氧基硅烷221g,滴加时间为1小时,于50℃保温3小时。取样测定总碱度0.13mol/kg,并通过计算加入冰乙酸2.19g中和催化剂以及未反应的氨丙基三乙氧基硅烷。过滤得到滤液,减压精馏收集130~140℃/1~10kPa馏分225g,通过GC-14C检测,纯度98%以上,收率91.1%,通过红外光谱分析,在2276cm-1有强而尖吸收峰,证明为N=C=O基团特征吸收峰。
Claims (9)
1、含异氰酸酯基团的硅烷的制备方法,其特征在于:主要包括如下步骤:
(1)采用氨基硅烷和碳酸酯为原料,在碱性催化剂作用下反应生成含硅基有机氨基甲酸酯的混合物;
(2)然后用中和试剂中和上述的反应混合物;
(3)将上述混合物过滤后,得到含硅基有机氨基甲酸酯的清液;
(4)最后对上述的清液进行减压精馏裂解,制得含异氰酸酯基团的硅烷。
2、如权利要求1所述的制备方法,其特征在于:所述的氨基硅烷与碳酸酯的摩尔比为1∶10~10∶1。
3、如权利要求1所述的制备方法,其特征在于:所述的氨基硅烷为如下结构式表示:
NH2RSiX(3-a)R1 a
上式中,R为饱和烷基,其碳链长度为C1~C12;R1为烷基,其碳链长度为C1~C12,或为芳基或芳烷基;a为0~3整数;X为烷氧基基团、烷基硅氧基基团或者烷氧基取代的烷氧基基团。
5、如权利要求1所述的制备方法,其特征在于:所述的碱性催化剂为M(OR3)y,其中,M为碱金属、碱土金属、第三主族元素或过渡金属;R3为不同或者相同的烷基基团,其碳链长度为C1~C10;y为1~4的整数;并且催化剂的用量占反应物总重量的0~6%,但不为0。
6、如权利要求1所述的制备方法,其特征在于:所述的中和试剂为盐酸、磷酸、冰乙酸、丙酸、丁酸、己酸、油酸、马来酸、富马酸或琥珀酸中的一种。
7、如权利要求1所述的制备方法,其特征在于:步骤(4)所述的减压精馏裂解的温度范围为100℃~200℃;减压真空度范围为:0~100mmHg,但不为0。
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JP4778844B2 (ja) * | 2006-06-20 | 2011-09-21 | 三井化学株式会社 | 珪素含有イソシアネート化合物の製造方法 |
CN101307067B (zh) * | 2007-05-16 | 2012-10-24 | 张家港市国泰华荣化工新材料有限公司 | 异氰酸酯基烷氧基硅烷的制备方法 |
CN101066978A (zh) * | 2007-06-01 | 2007-11-07 | 张家港市华盛化学有限公司 | 异氰酸酯烷基硅烷的制备方法 |
DE102012219324A1 (de) * | 2012-10-23 | 2014-04-24 | Evonik Industries Ag | Zusammensetzungen umfassend alkoxysilanhaltige Isocyanateund saure Stabilisatoren |
DE102014223823A1 (de) * | 2014-11-21 | 2016-05-25 | Wacker Chemie Ag | Herstellung von isocyanatfunktionellen Organosilanen |
CN109503647B (zh) * | 2017-09-15 | 2021-09-21 | 张家港市国泰华荣化工新材料有限公司 | 3-异氰酸酯基丙基三甲氧基硅烷的制法 |
CN108586516B (zh) * | 2018-06-06 | 2021-02-26 | 上海东大化学有限公司 | 一种氨基甲酸酯基烷氧基硅烷及异氰酸酯基烷氧基硅烷的制备方法 |
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Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4625012A (en) * | 1985-08-26 | 1986-11-25 | Essex Specialty Products, Inc. | Moisture curable polyurethane polymers |
JPH08218053A (ja) * | 1995-02-09 | 1996-08-27 | Mitsui Toatsu Chem Inc | タイル用一液型ウレタン系接着剤 |
US5623044A (en) * | 1992-10-13 | 1997-04-22 | Essex Specialty Products, Inc. | Polyurethane sealant compositions |
WO2002068501A2 (en) * | 2001-02-23 | 2002-09-06 | Henkel Loctite Corporation | Mixed alkoxysilyl functional polymers |
-
2003
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Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4625012A (en) * | 1985-08-26 | 1986-11-25 | Essex Specialty Products, Inc. | Moisture curable polyurethane polymers |
CN86103179A (zh) * | 1985-08-26 | 1987-03-04 | 埃塞克斯特殊产品公司 | 水可固化的聚氨酯聚合物的制备方法及其应用 |
US5623044A (en) * | 1992-10-13 | 1997-04-22 | Essex Specialty Products, Inc. | Polyurethane sealant compositions |
JPH08218053A (ja) * | 1995-02-09 | 1996-08-27 | Mitsui Toatsu Chem Inc | タイル用一液型ウレタン系接着剤 |
WO2002068501A2 (en) * | 2001-02-23 | 2002-09-06 | Henkel Loctite Corporation | Mixed alkoxysilyl functional polymers |
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