CN1350018A - 基于ipdi、hdi、其异氰脲酸酯类与胺的新型聚脲类 - Google Patents
基于ipdi、hdi、其异氰脲酸酯类与胺的新型聚脲类 Download PDFInfo
- Publication number
- CN1350018A CN1350018A CN01125870A CN01125870A CN1350018A CN 1350018 A CN1350018 A CN 1350018A CN 01125870 A CN01125870 A CN 01125870A CN 01125870 A CN01125870 A CN 01125870A CN 1350018 A CN1350018 A CN 1350018A
- Authority
- CN
- China
- Prior art keywords
- polyureas
- ipdi
- hdi
- acid ester
- ipd
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 title claims abstract description 14
- 150000001412 amines Chemical class 0.000 title claims abstract description 12
- 239000005058 Isophorone diisocyanate Substances 0.000 title claims description 12
- 235000013877 carbamide Nutrition 0.000 title description 5
- 150000003672 ureas Chemical class 0.000 title description 5
- 150000007971 urates Chemical class 0.000 title 1
- 229920002396 Polyurea Polymers 0.000 claims abstract description 23
- 239000005057 Hexamethylene diisocyanate Substances 0.000 claims abstract description 20
- RNLHGQLZWXBQNY-UHFFFAOYSA-N 3-(aminomethyl)-3,5,5-trimethylcyclohexan-1-amine Chemical compound CC1(C)CC(N)CC(C)(CN)C1 RNLHGQLZWXBQNY-UHFFFAOYSA-N 0.000 claims abstract description 19
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 claims abstract description 17
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 claims abstract description 16
- -1 isocyanuric acid ester Chemical class 0.000 claims description 15
- 239000002904 solvent Substances 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 6
- 239000011248 coating agent Substances 0.000 claims description 5
- 238000000576 coating method Methods 0.000 claims description 5
- 239000003973 paint Substances 0.000 claims description 5
- 150000002148 esters Chemical class 0.000 claims description 4
- 239000007787 solid Substances 0.000 claims description 4
- 238000010992 reflux Methods 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- 238000013019 agitation Methods 0.000 claims description 2
- 238000001816 cooling Methods 0.000 claims description 2
- 238000001035 drying Methods 0.000 claims description 2
- 239000004922 lacquer Substances 0.000 claims description 2
- 238000000034 method Methods 0.000 claims description 2
- 239000002994 raw material Substances 0.000 claims description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 239000003795 chemical substances by application Substances 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 230000004927 fusion Effects 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000004984 aromatic diamines Chemical class 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000006261 foam material Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000123 paper Substances 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 230000001131 transforming effect Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-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
- C08G18/791—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing isocyanurate groups
- C08G18/792—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing isocyanurate groups formed by oligomerisation of aliphatic and/or cycloaliphatic isocyanates or isothiocyanates
-
- 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
- C08G18/30—Low-molecular-weight compounds
- C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
- C08G18/3225—Polyamines
- C08G18/3234—Polyamines cycloaliphatic
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyurethanes Or Polyureas (AREA)
- Paints Or Removers (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
本发明涉及一种基于异佛尔酮二异氰酸酯(IPDI)、六亚甲基二异氰酸酯(HDI)和/或其异氰脲酸酯与胺,特别是异佛尔酮二胺(IPD)的新的聚脲类。
Description
技术领域
本发明涉及一种基于异佛尔酮二异氰酸酯(IPDI)、六亚甲基二异氰酸酯(HDI)和/或其异氰脲酸酯与胺，特别是异佛尔酮二胺(IPD)的新型聚脲类。
背景技术
聚脲类是众所周知的，可在下列技术领域作为粘合剂使用：木材和纸、发泡材料，以及作为色漆和涂料用的树脂(Houben-Weyl E20/2(1987)，pp.1721～1751；Houben-Weyl XIV/2(1963)，pp.165～171)。
发明内容
本发明的目的是发现一种在粉末涂料的标准固化温度150～220℃条件下保持为稳定固态形式同时不释放显著数量(≤2％)有机物质或水的新型聚脲类。
本发明的目的是一种基于异佛尔酮二异氰酸酯(IPDI)和/或六亚甲基二异氰酸酯(HDI)和/或其异氰脲酸酯与胺的聚脲类，其NCO/NH2比例等于0.9～1.1∶1，平均分子量至少为5000。
该新型聚脲类包含异佛尔酮二异氰酸酯(IPDI)、六亚甲基二异氰酸酯(HDI)与胺，特别是异佛尔酮二胺(IPD)，作为其起始化合物。IPDI和/或HDI既可以二异氰酸酯也可以异氰脲酸酯的形式使用。这里，这些异氰酸酯或者它们的异氰脲酸酯的混合物也是有利并适合的。
所有脂族、(环)脂族、环脂族和芳族二胺和/或多胺(C5～C18)，优选异佛尔酮二胺(IPD)，均可在本发明范围内使用。
一般而言，制成的聚脲类的NCO/NH2比例介于0.9～1.1∶1。在加入等摩尔数量，即NCO/NH2比例等于1∶1时，将获得具有最大交联度的固态和脆性聚合物，它仅当高于240℃时熔融并伴随分解，且不溶于溶剂。
本发明范围内优选的聚脲类是那些包含IPD与IPDI异氰脲酸酯和/或HDI异氰脲酸酯及其混合物的聚脲类。
本发明另一个目的是制造基于IPDI、HDI和胺，特别是IPD的聚脲类的方法，其中在诸如甲苯之类溶剂中使用胺，在搅拌下向其中加入异氰酸酯，需要的话也是以溶剂稀释后的。为实现完全转化，反应混合物在溶剂回流的条件下加热2～3h，然后冷却，分离(过滤)出生成的聚合物，然后在真空下在130～170℃干燥3～6h。
本发明聚脲类可用作油漆工业的原料，特别是制造挥发性漆、色漆和涂料。
具体实施方式
下面将通过实例更详细地说明本发明。
实施例
一般制造过程
70gIPD，以1000mL甲苯稀释后加入到备有搅拌器、滴液漏斗和加热罩的2L三颈烧瓶中。随后，当量(NH2∶NCO＝1∶1)数量的对应异氰酸酯或混合物以相同数量甲苯稀释后逐渐滴加到该胺溶液中。如此加毕后，反应混合物在回流下加热2h。冷却至室温后，滤出相应固体(聚脲)并在真空下干燥(在130～170℃3～6h)。
聚脲实施例(数据单位为重量份数)
1)VESTANAT T1890，Degussa-Hüls AG2)DESMODUR N330，Bayer AG
| IPD | IPDI | IPDI-三聚体1) | HDI-三聚体2) | |
| PH-1 | 70 | - | 183 | - |
| PH-2 | 70 | - | - | 138 |
| PH-3 | 70 | 61 | 61 | - |
| PH-4 | 70 | - | 91 | 69 |
所有产物均为白色/无色、脆性固体，不溶于标准溶剂中，仅在高于240℃熔融，伴随出现分解。
当上面所描述的聚脲类被用于例如粉末涂料时，将产物研磨并过筛至≤100μm是有利的。
Claims (12)
1.一种基于异佛尔酮二异氰酸酯(IPDI)和/或六亚甲基二异氰酸酯(HDI)和/或其异氰脲酸酯与胺的聚脲，其NCO/NH2比例等于0.9～1.1∶1，平均分子量至少为5000。
2.权利要求1的聚脲，它包含IPDI和异佛尔酮二胺(IPD)。
3.权利要求1的聚脲，它包含IPDI的异氰脲酸酯和IPD。
4.权利要求1的聚脲，它包含IPDI与IPDI异氰脲酸酯的混合物和IPD。
5.权利要求1的聚脲，它包含HDI和IPD。
6.权利要求1的聚脲，它包含HDI的异氰脲酸酯和IPD。
7.权利要求1的聚脲，它包含HDI与HDI异氰脲酸酯的混合物和IPD。
8.权利要求1的聚脲，它包含IPDI异氰脲酸酯与HDI异氰脲酸酯的混合物和IPD。
9.权利要求1～8中至少一项的聚脲，其特征在于，
它以固体形式存在，并且不溶于溶剂。
10.制造权利要求1～9的、基于IPDI和/或HDI和/或其异氰脲酸酯与胺的聚脲类的方法，其特征在于，在溶剂中使用胺，在搅拌下向其中加入异氰酸酯，需要的话也是以溶剂稀释的，然后在溶剂回流的条件下加热2～3h，然后冷却，分离出生成的聚合物，然后在真空下在130～170℃干燥3～6h。
11.权利要求1～8的聚脲类作为油漆工业原料的应用。
12.权利要求1～8的聚脲类用于制造挥发性漆、色漆和涂料的应用。
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10042322.1 | 2000-08-29 | ||
| DE10042322A DE10042322A1 (de) | 2000-08-29 | 2000-08-29 | Neue Polyharnstoffe auf der Basis von IPDI, HDI, deren Isocyanurate und Aminen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN1350018A true CN1350018A (zh) | 2002-05-22 |
Family
ID=7654124
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN01125870A Pending CN1350018A (zh) | 2000-08-29 | 2001-08-28 | 基于ipdi、hdi、其异氰脲酸酯类与胺的新型聚脲类 |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US20020040763A1 (zh) |
| EP (1) | EP1184399A3 (zh) |
| JP (1) | JP2002069149A (zh) |
| CN (1) | CN1350018A (zh) |
| AU (1) | AU3893401A (zh) |
| BR (1) | BR0103725A (zh) |
| CA (1) | CA2356006A1 (zh) |
| DE (1) | DE10042322A1 (zh) |
| HK (1) | HK1044162A1 (zh) |
| TW (1) | TW553824B (zh) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2012000944A1 (en) | 2010-06-29 | 2012-01-05 | Bayer Materialscience Ag | Aliphatic polyurea coating, the method for preparing the same and the use thereof |
| CN104650322A (zh) * | 2015-02-18 | 2015-05-27 | 中国科学院长春应用化学研究所 | 一种二氧化碳基聚脲高分子材料的制备方法 |
| CN109401579A (zh) * | 2018-09-20 | 2019-03-01 | 中北大学 | 一种非异氰酸酯聚脲粉末涂料的制备方法 |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4550259B2 (ja) * | 2000-12-01 | 2010-09-22 | 日本ペイントマリン株式会社 | エポキシ塗料組成物並びに防食塗装方法及び被塗物 |
| EP1336629A3 (de) * | 2002-02-16 | 2003-10-15 | Degussa AG | Verfahren zur Herstellung von Urethan(meth)acrylaten |
| DE10221047A1 (de) | 2002-05-10 | 2003-11-27 | Degussa | Verfahren zur lösemittelfreien,kontinuierlichen Herstellung von Polyharnstoffen |
| DE10233104A1 (de) * | 2002-07-20 | 2004-01-29 | Degussa Ag | Verwendung von PUR-Pulverlacken für Coil Coating-Beschichtungen mit mattem Erscheinungsbild |
| US7572508B2 (en) | 2004-07-12 | 2009-08-11 | Acushnet Company | Polyurea coatings for golf equipment |
| EP1626061A1 (de) * | 2004-08-11 | 2006-02-15 | Rhein Chemie Rheinau GmbH | Verfahren zur Herstellung pulverförmiger (Poly)harnstoffe |
| KR100728388B1 (ko) * | 2007-02-14 | 2007-06-13 | 듀라케미 (주) | 방청방수용 지방족화합물계 폴리우레아 코팅제 |
| JP6499022B2 (ja) * | 2015-06-11 | 2019-04-10 | 本田技研工業株式会社 | 輸送機器部材用ポリウレア架橋粒子及び摺動部材 |
| EP3723839B1 (en) | 2017-12-11 | 2025-02-05 | Innovative Surface Technologies, Inc. | Polyurea copolymer coating compositions and methods |
| US20240218108A1 (en) * | 2022-12-29 | 2024-07-04 | Si Group, Inc. | Polyurea and Method of Making Using an Amine Compound |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3143060A1 (de) * | 1981-10-30 | 1983-05-11 | Chemische Werke Hüls AG, 4370 Marl | Pulverlacke auf der basis von blockierten isophorondiisocyanataddukten |
| DE3814531A1 (de) * | 1988-04-29 | 1989-11-09 | Bayer Ag | Farbmittel |
| CA2151672C (en) * | 1994-06-24 | 2007-05-29 | Dudley Joseph Ii Primeaux | Preparation of sprayable aliphatic polyurea elastomers having improved properties |
| US5856420A (en) * | 1996-04-17 | 1999-01-05 | Arco Chemical Technology, L.P. | Bis(isobutyraldimine) of 1,4-diaminobutane in HDI trimer and biuret-based coatings |
| US6013755A (en) * | 1997-03-11 | 2000-01-11 | Huntsman Petrochemical Corporation | Method of preparing an aliphatic polyurea spray elastomer system |
| US6399736B1 (en) * | 1997-03-11 | 2002-06-04 | Huntsman Petrochemical Corporation | Method of preparing spray elastomer systems |
| DE19831307A1 (de) * | 1998-07-13 | 2000-01-20 | Degussa | Harnstoff- und uretdiongruppenhaltige Polyadditionsverbindungen, ein Verfahren zu ihrer Herstellung sowie deren Verwendung |
-
2000
- 2000-08-29 DE DE10042322A patent/DE10042322A1/de not_active Withdrawn
-
2001
- 2001-04-27 AU AU38934/01A patent/AU3893401A/en not_active Abandoned
- 2001-07-12 EP EP01116975A patent/EP1184399A3/de not_active Withdrawn
- 2001-08-24 TW TW090120858A patent/TW553824B/zh active
- 2001-08-27 CA CA002356006A patent/CA2356006A1/en not_active Abandoned
- 2001-08-28 US US09/939,686 patent/US20020040763A1/en not_active Abandoned
- 2001-08-28 JP JP2001258303A patent/JP2002069149A/ja active Pending
- 2001-08-28 BR BR0103725-0A patent/BR0103725A/pt not_active Application Discontinuation
- 2001-08-28 CN CN01125870A patent/CN1350018A/zh active Pending
-
2002
- 2002-07-31 HK HK02105642.9A patent/HK1044162A1/zh unknown
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2012000944A1 (en) | 2010-06-29 | 2012-01-05 | Bayer Materialscience Ag | Aliphatic polyurea coating, the method for preparing the same and the use thereof |
| CN104650322A (zh) * | 2015-02-18 | 2015-05-27 | 中国科学院长春应用化学研究所 | 一种二氧化碳基聚脲高分子材料的制备方法 |
| CN109401579A (zh) * | 2018-09-20 | 2019-03-01 | 中北大学 | 一种非异氰酸酯聚脲粉末涂料的制备方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| EP1184399A2 (de) | 2002-03-06 |
| JP2002069149A (ja) | 2002-03-08 |
| BR0103725A (pt) | 2002-05-21 |
| AU3893401A (en) | 2002-03-07 |
| EP1184399A3 (de) | 2003-10-01 |
| TW553824B (en) | 2003-09-21 |
| HK1044162A1 (zh) | 2002-10-11 |
| US20020040763A1 (en) | 2002-04-11 |
| DE10042322A1 (de) | 2002-03-14 |
| CA2356006A1 (en) | 2002-02-28 |
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