TW201540739A - 經矽烷改質之甲醯胺 - Google Patents
經矽烷改質之甲醯胺 Download PDFInfo
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- TW201540739A TW201540739A TW104102943A TW104102943A TW201540739A TW 201540739 A TW201540739 A TW 201540739A TW 104102943 A TW104102943 A TW 104102943A TW 104102943 A TW104102943 A TW 104102943A TW 201540739 A TW201540739 A TW 201540739A
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- WOZZOSDBXABUFO-UHFFFAOYSA-N tri(butan-2-yloxy)alumane Chemical compound [Al+3].CCC(C)[O-].CCC(C)[O-].CCC(C)[O-] WOZZOSDBXABUFO-UHFFFAOYSA-N 0.000 description 1
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- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-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
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- 229910052725 zinc Inorganic materials 0.000 description 1
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- IFNXAMCERSVZCV-UHFFFAOYSA-L zinc;2-ethylhexanoate Chemical compound [Zn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O IFNXAMCERSVZCV-UHFFFAOYSA-L 0.000 description 1
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- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
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- C07F7/1804—Compounds having Si-O-C linkages
- C07F7/1872—Preparation; Treatments not provided for in C07F7/20
- C07F7/1888—Preparation; Treatments not provided for in C07F7/20 by reactions involving the formation of other Si-linkages, e.g. Si-N
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G18/12—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step using two or more compounds having active hydrogen in the first polymerisation step
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- 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
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- C08G18/2805—Compounds having only one group containing active hydrogen
- C08G18/288—Compounds containing at least one heteroatom other than oxygen or nitrogen
- C08G18/289—Compounds containing at least one heteroatom other than oxygen or nitrogen containing silicon
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- 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
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- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/73—Polyisocyanates or polyisothiocyanates acyclic
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- 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
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- C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
- C08G18/7614—Polyisocyanates or polyisothiocyanates cyclic aromatic containing only one aromatic ring
- C08G18/7621—Polyisocyanates or polyisothiocyanates cyclic aromatic containing only one aromatic ring being toluene diisocyanate including isomer mixtures
-
- 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
- C08G18/7806—Nitrogen containing -N-C=0 groups
- C08G18/7818—Nitrogen containing -N-C=0 groups containing ureum or ureum derivative groups
- C08G18/7831—Nitrogen containing -N-C=0 groups containing ureum or ureum derivative groups containing biuret groups
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- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
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- C08G18/8009—Masked polyisocyanates masked with compounds having at least two groups containing active hydrogen with compounds of C08G18/32 with compounds of C08G18/3203
- C08G18/8012—Masked polyisocyanates masked with compounds having at least two groups containing active hydrogen with compounds of C08G18/32 with compounds of C08G18/3203 with diols
- C08G18/8019—Masked aromatic polyisocyanates
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- C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
- C09D175/04—Polyurethanes
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- C09D183/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Coating compositions based on derivatives of such polymers
- C09D183/16—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Coating compositions based on derivatives of such polymers in which all the silicon atoms are connected by linkages other than oxygen atoms
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- C09J183/00—Adhesives based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Adhesives based on derivatives of such polymers
- C09J183/16—Adhesives based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Adhesives based on derivatives of such polymers in which all the silicon atoms are connected by linkages other than oxygen atoms
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- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Polyurethanes Or Polyureas (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Sealing Material Composition (AREA)
- Paints Or Removers (AREA)
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Abstract
本發明係關於一種新穎經矽烷改質之甲醯胺聚合物及/或預聚合物,用於黏結及/或密封各種基板材料,例如金屬、木頭、玻璃及/或塑膠材料。又,另外提供一種反應性單組份黏合系統,其包含根據本發明的經矽烷改質之甲醯胺聚合物。
Description
本發明係關於一種新穎之式(I)及式(IV)的經矽烷改質之甲醯胺預聚合物,用於塗層、黏結及/或密封各種基板材料,例如金屬、木頭、玻璃及/或塑膠材料。又,另外提供一種反應性單組份黏合系統,其包含按照本發明之式(I)及/或式(IV)的經矽烷改質之甲醯胺預聚合物。
經矽烷改質之聚合物多年來已為人所知,而以經矽烷改質之預聚合物或聚合物為基底的密封材料或黏合劑已證實適合用於多種應用,例如汽車製造、窗戶或結構飾面的密封步驟。
一般而言,經矽烷改質之聚合物(處理之前為預聚合物的形式)視為包含矽烷基團的聚合物,該矽烷基團具有可水解自由基,且不同於矽烷,其聚合物骨架並未大致由O-Si-O-Si鏈構成,而是由C-C鏈構成,在大多數情況下會插入雜原子和其他複合尿烷、乙醚、酯、尿素、醯胺和其他結構單元。在水分的作用下,矽烷基團的自由基,例如通常為乙酸或烷氧基,會由於形成反應性矽烷醇而水解,然後藉由水、醇或乙酸裂解反應而濃縮和硬化以形成高分子量架構。
此等經矽烷改質之聚合物的值大致上代表其特定性質。換言之,包含經矽烷改質之聚合物的塗層材料、黏合劑或密封材料之特徵為不需要複雜的預處理即對各種基板展現強大黏合性(不需要底膠)。原因是OH基團通常會出現在無機基板表面且可與在水分的作用下形成之聚合物的反應性矽烷醇反應。換言之,經矽烷改質之聚合物的性質可藉由聚合物骨架的輔助調整成適用於各種不同應用。
因此,目前市售的經矽烷改質之聚尿烷和聚尿素係以高分子量骨架為基底,其製造方法為:(i)使含NCO的預聚合物與胺基矽烷反應;或(ii)使OH封端的預聚合物,例如聚乙醚、聚尿烷或聚酯,與NCO官能的矽烷反應,如下列式圖示所示:
然而,以經矽烷改質之聚尿素為基底的塗層材料、黏合劑和密封材料之缺點為其預聚合物具有高黏度。由於高黏度,經矽烷改質之聚尿素只能用於有限範圍,原因是使用塗層或密封材料時,通常必須以液體或膏狀的形式施加至待塗層或黏合的基板部分。因此,過於黏稠的預聚合物難以或無法作為塗層材料、黏合劑及/或密封材
料。
此外,作為矽烷交聯後之終端產品而獲得的塗層、黏結及/或密封之硬度程度在特定應用中扮演重要角色。若為經矽烷改質之聚尿素,通常可獲得具有高硬度程度的終端產品。另一方面,經矽烷改質之聚尿烷在硬化後提供較軟的終端產品。然而,由於必須使用相對昂貴的NCO官能化之矽烷先驅物,因此難以採用經濟實惠的方式來合成具有高矽烷含量的經矽烷改質之聚尿烷。
經矽烷改質之聚合物中的單分子構造NCO成分另外在此鍵結中扮演重要角色:由於有不可忽略的異氰酸酯蒸汽壓(即使在室溫亦同),可能危害健康或至少有刺激性的異氰酸酯蒸汽即使在噴灑應用期間亦會產生。因此,有必要開發一種反應性預聚合物,其大致不含異氰酸酯單體且在任何情況下皆低於按照災害物質技術規定(TRGS)430(3/2009版本)的暴露極限值(總反應性異氰酸酯基濃度),亦即0.018毫克/立方公尺NCO,較佳為低於0.01毫克/立方公尺,特佳為低於0.001毫克/立方公尺。
因此,本發明之目的在於提供一種經改良的單組份黏合及/或塗層系統,其使用價格低廉且易於取得之起始材料,該系統盡可能不危害健康且大致避免已知經矽烷改質之聚合物的上述問題。
茲此特別提供一種反應性單組份黏合系統,其具有低黏性和低結晶性因而易於處理,同時允許終端產物具有高化學安定性。另外,亦需要一種聚合終端產品,其可廉價製造且各種特性均勻分佈,例
如具有特定程度的硬化和化學安定性。
本發明係關於一種如申請專利範圍第1項的式(I)之化合物,適合作為各種基板材料(例如金屬、木頭、玻璃及/或塑膠材料)的經改良塗層、黏結及/或密封之單組份黏合系統/塗層系統。
在最後的硬化狀態,本發明提供藉由-Si-O-Si-橋接而縮合的聚合物作為永久塗層、黏合劑及/或密封材料。
本發明進一步提供製造式(I)及式(IV)之化合物的方法。
按照本發明,提供式(I)的化合物:
其中在式(I)中:Y代表m價的分子自由基,其為由單異氰酸酯(m=1)、聚異氰酸酯(m>1)或含異氰酸酯基團的預聚合物(m=從1至20)之m個NCO自由基所還原的結構單元;R1代表至少雙價的選擇性取代之線性或支鏈脂肪族、脂環族、芳脂及/或芳香族結構單元,其具有從1至12個碳原子,其中一或多個非鄰接亞甲基可由O或S取代;R2和R3相互獨立分別代表選擇性取代之線性或支鏈脂肪族基,其具有從1至12個碳原子;n代表從0至2的整數;及
m代表從1至20的數字。
在按照本發明的一具體實例中,提供式(I)的化合物。
在按照本發明的另一具體實例中,提供一種製造式(I)的化合物之方法,其包含使式(Ia)的經矽烷改質之甲醯胺與式Y-(NCO)m的異氰酸酯反應:
其中Y、R1、R2、R3、n和m如申請專利範圍第1項的定義。
在按照本發明的另一具體實例中,提供一種反應性單組份黏合系統及/或塗層系統,包含至少一種式(I)的化合物。
按照本發明,式(I)的化合物用於製造黏合劑和密封材料、塗漆、塗層、塗料、油墨及/或印刷油墨。
在按照本發明的另一具體實例中,提及對按照本發明的反應性單組份黏合系統之用途,用於金屬、木頭、木頭為主材料、玻璃、皮革、紡織品、塑膠材料、礦物材料、軟木、纖維、混凝土、紙、硬紙板和薄膜之黏結及/或密封。
按照本發明,另外揭示一種複合物,由按照本發明的單組份黏合系統所黏合。
在本案中使用的「脂環族」一詞係指不屬於芳香族化合物的碳環族或雜環化合物,例如環烷烴、環烯烴或氧雜-、硫雜-、氮雜-或
三氮雜-環烷烴。其特定實例為插入一或兩個N或O原子的環己基、環戊基及其衍生物,例如嘧啶、吡嗪、四氫哌喃或四氫呋喃。
在本發明中使用的「芳脂」一詞係指由芳基取代的烷基自由基,例如苄基、苯基乙基、二苯基等。
本案中的「選擇性取代」或「取代」係特別指由-F、-Cl、-I、-Br、-OH、-OCH3、-OCH2CH3、-O-正丙基或-O-異丙基、-OCF3、-CF3、-S-C1-6-烷基及/或其他線性或支鏈脂肪族、脂環族、芳脂及/或芳香族結構單元(其具有從1至12個碳原子且選擇性由雜原子連結)取代相關結構單元。較佳為其係指由鹵素(特別是-F、-Cl)、C1-6-烷氧基(特別是甲氧基和乙氧基)、羥基、三氟甲基和三氟甲氧基進行之取代。
本案中使用的「低分子量」一詞係指分子量未超過約800克.莫耳-1的化合物。
本案中使用的「高分子量」一詞係指分子量超過約800克.莫耳-1的化合物。
若化合物的分子量並非由明確定義的結構式計算而得,例如聚合物,則在每一例中應該將分子量視為平均分子量。
本案中使用的「單異氰酸酯」係指由A-NCO表示的化合物,其中A代表具有6至50個碳原子的芳香族、芳脂、脂肪族或環脂肪族。
本案中使用的「聚異氰酸酯」一詞係指具有的NCO官能性較佳為2的芳香族、芳脂、脂肪族或環脂肪族聚異氰酸酯,特別是二-和三-異氰酸酯。
本案中使用的「單體」一詞係指具有官能性基團的低分子化合物,用於合成低聚物及/或(預)聚合物且具有明確的分子量。
本案中使用的「低聚物」一詞係指僅部分同類型或不同類型的單體互相重複連接的化合物。
本案中使用的「預聚合物」一詞係指具有官能性基團的低聚化合物,用於聚合物的最終合成。
本案中使用的「聚合物」一詞係指高分子化合物,其中的相同類型或不同類型之單體、低聚物及/或預聚合物互相重複連接,而且可具有不同程度的聚合化、分子量分佈或鏈長度。
按照本發明的具體實例詳情如下所示。
在一具體實例中,提供通式(I)的化合物:
其中在式(I)中:Y代表m價的分子自由基,其為由單異氰酸酯(m=1)、聚異氰酸酯(m>1)或含異氰酸酯基團的預聚合物(m=從1至20)之m個NCO自由基所還原的結構單元;R1代表至少雙價的選擇性取代之線性或支鏈脂肪族、脂環族、芳脂及/或芳香族結構單元,其具有從1至12個碳原子,其中一或多個非鄰接亞甲基可由O或S取代;R2和R3相互獨立分別代表選擇性取代之線性或支鏈脂肪族基,其具有從1至12個碳原子;
n代表從0至2的整數;及m代表從1至20的數字,其中m亦可為分數。
在按照本發明的一具體實例中,結構單元Y為衍生自單異氰酸酯的自由基。此種單異氰酸酯的實例為己基異氰酸酯、6-氯己基異氰酸酯、正辛基異氰酸酯、環己基異氰酸酯、2-乙基己基異氰酸酯、2,3,4-甲基環己基異氰酸酯、3,3,5-三甲基環己基異氰酸酯、2-降莰基-甲基異氰酸酯、癸基異氰酸酯、十二基異氰酸酯、十四基異氰酸酯、十六基異氰酸酯、十八基異氰酸酯、3-丁氧基丙基異氰酸酯、3-(2-乙基己基氧基)-丙基異氰酸酯、苯基異氰酸酯、甲苯基異氰酸酯、氯苯基異氰酸酯(2,3,4-異構物)、二氯苯基異氰酸酯、4-硝基苯基異氰酸酯、3-三氟甲基苯基異氰酸酯、苄基異氰酸酯、二甲基苯基異氰酸酯(市售混合物和個別異構物)、4-十二基癸基苯基異氰酸酯、4-環己基-苯基異氰酸酯、1-萘基異氰酸酯、異氰酸基-醯胺,其溶於1莫耳二異氰酸酯和1莫耳單羧酸,較佳為甲苯二異氰酸酯、二苯基甲烷二異氰酸酯和十六基亞甲基二異氰酸酯,其中含較佳為至少6個碳原子的脂肪族單羧酸,例如(6-異氰酸基-己基)-硬酯酸醯胺、(3-異氰酸基甲苯基)-硬酯酸醯胺、(6-異氰酸基己基)-苯甲醯胺,在每一例中單獨使用或是混合複數單異氰酸酯使用。
在按照本發明的另一具體實例中,結構單元Y係衍生自聚異氰酸酯的自由基。作為聚異氰酸酯,可使用熟習相關技術者所知悉之包括NCO官能性較佳為2的芳香族、芳脂、脂肪族或環脂肪族聚異氰酸酯。此等亦可具有亞氨基氧雜二嗪二酮、異氰尿酸酯、尿丁二酮、尿烷、尿甲酸酯、雙尿、尿素、氧二嗪三酮、氧唑啉酮、醯基尿及/或碳二醯亞胺結構。
上述聚異氰酸酯係以熟習相關技術者所知悉的具有脂肪族、環脂肪族、芳脂及/或芳香族鍵結之異氰酸酯基的二-或三-異氰酸酯為基底,製造方法可為使用光氣亦可為不使用光氣。此種二-和三-異氰酸酯的實例為1,4-二異氰酸基丁烷、1,5-二異氰酸基戊烷、1,6-二異氰酸基己烷(HDI)、2-甲基-1,5-二異氰酸基戊烷、1,5-二異氰酸基-2,2-二甲基戊烷、2,2,4-或2,4,4-三甲基-1,6-二異氰酸基己烷、1,10-二異氰酸基癸烷、1,3-和1,4-二異氰酸基環己烷、1,3-和1,4-雙-(異氰酸基甲基)-環己烷、1-異氰酸基-3,3,5-三甲基-5-異氰酸基甲基環-己烷(異佛酮二異氰酸酯,IPDI)、4,4'-二異氰酸基二環己基甲烷(Desmodur® W,Bayer AG,Leverkusen,DE)、4-異氰酸基甲基-1,8-辛烷二異氰酸酯(三異氰酸基壬烷,TIN)、二異氰酸基-1,3-二甲基環己烷(H6XDI)、1-異氰酸基-1-甲基-3-異氰酸基甲基環己烷、1-異氰酸基-1-甲基-4-異氰酸基甲基環己烷、雙-(異氰酸基甲基)-降莰烷、1,5-萘二異氰酸酯、1,3-和1,4-雙-(2-異氰酸基-丙-2-基)-甲苯(TMXDI)、2,4-和2,6-二異氰酸基甲苯(TDI),特別是2,4-和2,6-同分異構物和市售兩種異構物的混合物、2,4'-和4,4'-二異氰酸基二苯基甲烷、1,5-二異氰酸基萘、1,3-雙(異氰酸基甲基)甲苯(XDI)和上述化合物的任意混合物。
特佳為聚異氰酸酯具有的平均NCO官能性為從2.0至5.0,最特佳為從2.3至4.5,且異氰酸酯基團含量較佳為從5.0至27.0重量%,特佳為從14.0至24.0重量%,單體二異氰酸酯含量較佳為低於1重量%,特佳為低於0.5重量%。
較佳為可使用上述類型的聚異氰酸酯或聚異氰酸酯混合物,其僅包含脂肪族及/或環脂肪族鍵結的異氰酸酯基。
特佳為上述類型的聚異氰酸酯係基於十六基亞甲基二異氰酸酯、異佛酮二異氰酸酯、同分異構物雙-(4,4'-異氰酸基環己基)-甲烷、2,4-和2,6-二異氰酸基甲苯、2,4'-和4,4'-二異氰酸基二苯基甲烷及其混合物。
在按照本發明的其他具體實例中,結構單元Y係為衍生自帶有異氰酸酯基團的預聚合物之自由基。此可特別為聚尿烷預聚合物。按照本發明製造帶有異氰酸酯基團Y-(NCO)m的聚尿烷預聚合物時,使一或多種上述聚異氰酸酯與一種或多種多元醇反應。
作為適合的多元醇,可使用聚尿烷化學中為熟習相關技術者所知悉的所有多元醇,其中多元醇較佳為具有平均OH官能性1.5,特佳為從1.8至2.5。
此等可為例如低分子量二醇(例如1,2-乙二醇、1,3-或1,2-丙二醇、1,4-丁二醇、2,2,4-三甲基戊二醇)、三醇(例如甘油、三羥甲基丙烷)和四醇(例如季戊四醇)、聚乙醚多元醇、聚酯多元醇、聚丙烯酸多元醇及聚碳酸多元醇。較佳的多元醇為以聚乙醚為基底的上述類型之物質。
使用聚乙醚多元醇時,較佳為使用平均分子量Mn為從300至20,000克/莫耳的聚乙醚多元醇,特佳為從1000至12,000克/莫耳,最特佳為從2000至6000克/莫耳。
此外,較佳為具有平均OH官能性1.9,特佳為1.95。
此等聚乙醚的OH官能性較佳為<6,特佳為<4,最特佳為<
2.2。
同樣適合的多元醇為源自適合醇類和酸類之縮合反應的聚酯多元醇。作為醇類一級和二-一級二醇,可使用例如乙二醇、二乙二醇、三乙二醇、1,2-丙二醇、二丙二醇、1,3-丁二醇、1,4-丁二醇、1,6-己二醇或新戊二醇,以及高氫醇類,例如三羥甲基丙烷、三羥甲基乙烷或季戊四醇。適合的縮合配偶體為酸成分,例如肥酸或苯二甲酸。使用乙基己酸錫(II)或四烷氧鈦及上述類型的二醇或三醇等金屬催化劑作為起始劑對ε-己內酯或甲基-ε-己內酯進行開環聚合化亦會產生適合的聚酯多元醇。因此,聚酯多元醇的長度可由所使用的己內酯單元數量決定。
聚酯多元醇的較佳分子量(平均量)為1000克/莫耳。聚酯多元醇的較佳官能性為從2至3。
聚丙烯酸多元醇亦適合製造按照本發明的預聚合物。聚丙烯酸多元醇的平均分子量為從200至10,000克/莫耳,特佳為從200至6000克/莫耳,最特佳為從200至2500克/莫耳。所使用的聚丙烯酸多元醇之官能性較佳為從1.6至3.8,特佳為從1.8至3.5。此等聚丙烯酸多元醇的OH量較佳為從15至150,特佳為從20至100,最特佳為從40至80毫克KOH/克。適用者例如Acryflow® P60和P90(來自Lyondell,US的市售產品)。
脂肪族聚碳酸多元醇亦是合成按照本發明的預聚合物時所考慮的對象。已知聚碳酸多元醇可從光氣與多元醇的縮合反應或從適合的有機碳酸與多元醇的酯交換反應獲得。可考慮的有機碳酸酯為芳基、烷基和伸烷基碳酸酯及其混合物。可提及的實例為二苯基碳酸酯(DPC)、二甲基碳酸酯(DMC)、二乙基碳酸酯(DEC)和乙烯碳酸酯。
可考慮的多元醇為聚酯多元醇部分提及的多元醇。所使用的聚碳酸多元醇之官能性較佳為從1.6至3.8,特佳為從1.8至3.5。此等聚碳酸多元醇的平均分子量較佳為從100至6000克/莫耳,特佳為從100至4000克/莫耳。OH數量取決於聚碳酸酯多元醇的官能性,通常為從20至900毫克KOH/克。
其他適合的多元醇例如亦為EP-A 0 689 556和EP-A 0 937 110中描述的特定多元醇,例如可藉由環氧化物開環使環氧化脂肪酸與脂肪族或芳香族多元醇反應而獲得。
亦可使用含羥基的聚丁二烯作為多元醇。
製造按照本發明的聚尿烷預聚合物Y-(NCO)m時所使用的方法原則上為已知的聚尿烷化學方法。因此,使多元醇(個別或混合物形式)與多餘聚異氰酸酯(個別或混合物形式)反應,選擇性使用催化劑及/或輔助物質及添加劑。將均質反應混合物攪拌直到達到固定的NCO值。然後,藉由持續蒸餾移除任何未反應的聚異氰酸酯。
本發明中持續的蒸餾方法係指僅部分來自上述方法步驟的預聚合物短暫暴露至較高的溫度,而尚未經過蒸餾方法的預聚合物維持在較低的溫度。較高的溫度係指在相應特定壓力下會使揮發性成分蒸發的溫度。
進行蒸餾的溫度較佳為低於170℃,特佳為從110至170℃,最特佳為從125至145℃,且壓力低於20毫巴,特佳為低於10毫巴,最特佳為從0.05至5毫巴。
尚未經過蒸餾方法之含預聚合物的反應混合物之溫度較佳為從0至60℃,特佳為從15至40℃,最特佳為從20至40℃。
在本發明的較佳具體實例中,蒸餾溫度及尚未經過蒸餾方法之
含預聚合物的反應混合物之溫度的差異為至少5℃,特佳為至少15℃,最特佳為從15至40℃。
蒸餾的執行速率較佳為將體積增量的待蒸餾之含預聚合物的反應混合物暴露在蒸餾溫度下低於10分鐘,特佳為低於5分鐘,然後選擇性藉由主動冷卻返回蒸餾之前含預聚合物的反應混合物之起始溫度。溫度負載較佳為使蒸餾之前的反應混合物之溫度或蒸餾之後的預聚合物之溫度為至少5℃,特佳為至少15℃,最特佳為從15至40℃,高於所套用的蒸餾溫度。
較佳的持續蒸餾技術為分子、降膜及/或薄膜蒸餾(相關資訊請參閱例如Chemische Technik,Wiley-VCH,Volume 1,5th edition,pages 333-334)。
降膜式蒸發器包含靜止的長管束,待蒸發的液體從上方流入其中且呈膜狀向下流動。藉由蒸汽在管壁處加熱。蒸汽泡形成於管內且連同液體向下流動而確保擾流狀態。蒸汽和液體會在分離器容器底部分離。
薄膜蒸發器為適合用於僅可短暫暴露於熱源之溫度敏感物質的蒸發之儀器。待蒸發的液體從上方流入管內經過夾套加熱。該液體在管內以膜狀流動。在管內,懸於軸上的刮刷器會旋轉確保固定的薄膜厚度。較佳為使用具有上述參數的薄膜蒸餾作為連續蒸餾技術。
在反應中,聚異氰酸酯的NCO基團對多元醇的OH基團的當量比較佳為從10:1至2:1,特佳為從7:1至2:1。
所選的反應溫度為從0℃至250℃,較佳為從20℃至140℃,最特佳為從40℃至100℃。
按照本發明的方法誠然亦可在有芳香族化合物、氯化芳香族化合物、酯或氯化碳水化合物等溶劑的環境下進行。
為了加速尿烷化,可使用已知的催化劑,例如有機金屬化合物、胺類(例如三級胺)或金屬化合物,例如辛酸鉛、琥珀酸汞、三氟甲烷磺酸鋅、辛酸錫或二月桂酸二丁錫。若以附隨方式使用催化劑,添加量較佳為從0.001至5重量%,特佳為從0.002至2重量%,以待反應的聚異氰酸酯和多元醇總量為基準。
較佳為可提供式(I)和(III)之化合物,其中:R代表亞甲基(-CH2-)、乙烯(-CH2CH2-)、丙烯(-CH2CH2CH2-)、亞異佛爾酮基、4,4'-二環己基亞甲基、雙(環己烯)、4,4'-雙伸苯基、鄰、間、對甲伸苯基或己烯(特別是-CH2CH2CH2CH2CH2CH2-),且特別較佳為正己烯;R1代表亞甲基(-CH2-)或丙烯(特別是正丙烯-CH2CH2CH2-),特佳為正丙烯;R2和R3相互獨立分別代表甲基或乙基,較佳為乙基;且n代表從0至2的整數。
特佳為可提供式(I)及/或(III)之化合物:R代表亞異佛爾酮基、4,4'-二環己基亞甲基、雙(環己烯)、雙伸苯基、甲伸苯基或正己烯;R1代表正丙烯;R2和R3相互獨立分別代表甲基或乙基;且n代表從0至2的整數。
最特佳為可提供式(III)之化合物,其中R為亞異佛爾酮基、甲
伸苯基或正己烯,R1為正丙烯,R2和R3為甲基,且n=0。
按照本發明的式(I)之化合物適合作為黏合材料、黏合劑及/或密封材料的結合劑。
式(I)的化合物之黏度(在23℃)為從100至1,000,000mPa.s,較佳為從1000至500,000mPa.s,特佳為從5000至300,000mPa.s。
由存在醯基尿基,相較於包含尿素基團的類似化合物,按照本發明的式(I)之化合物具有較低的黏性。如同熟習相關技術者所知悉,結果為帶來改良的管理性或進一步加工著色的塗層,或是更妥善埋入用於製造黏合劑或密封材料的白堊等填充劑。
按照本發明的式(I)之化合物可藉由以下兩階段方法製造:
較佳為先將多餘甲酸烷基酯R'O-CHO逐滴加進胺基H2NR1-Si(R2)n(OR3)3-n,R'較佳為代表具有從1至4個碳原子的烷基。甲酸甲酯或乙基甲酸特佳為作為甲酸烷基酯R'O-CHO。在甲酸烷基的沸點溫度,較佳為使1莫耳胺基與從1.01至6莫耳的多餘甲酸烷基酯R'O-CHO反應,特佳為從1.05至4莫耳。當反應完成時,藉由薄膜蒸餾以蒸餾分離出多餘甲酸烷基酯R'O-CHO和獲得的醇
類R'-OH,且選擇性蒸餾分離出獲得的產物(Ia)。
再者,使式(Ia)的化合物與Y-(NCO)m反應,較佳為在惰性環境下,溫度為從20至200℃,較佳為從40至160℃。因此,較佳為使用兩個成分時,其異氰酸酯基團對甲醯胺基團的當量比為從至少1:10至不超過40:1,較佳為從1:5至不超過30:1,特佳為從1:2至不超過25:1。可在溶液中或無溶劑環境下進行反應。
製造具有式(I)的化合物時,可不使用催化劑。然而,亦可選擇性加入已知的催化劑以便加速反應。可用的催化劑例如三級胺,例如三乙基胺、三丁胺、二甲基苄基胺、二乙基苄基胺、砒啶、甲基吡啶、二環己基甲基胺、二甲基-環己基胺、N,N,N',N'-四甲基二胺基二乙基乙醚、雙-(二甲基胺基丙基)-尿素、N-甲基-或N-乙基-嗎福啉、N-椰油基嗎福啉、N-環己基嗎福啉、N,N,N',N'-四甲基乙烯二胺、N,N,N',N'-四甲基-1,3-丁烷二胺、N,N,N',N'-四甲基-1,6-己烷二胺、五甲基二乙烯三胺、N-甲基派啶、正二甲基-胺基乙基派啶、N,N'-二甲基哌嗪、N-甲基-N'-二甲基胺基哌嗪、1,2-二甲基咪唑、2-甲基咪唑、N,N-二甲基咪唑-ß-苯基乙基胺、1,4-二氮雜雙環-(2,2,2)-辛烷(DABCO)和雙-(N,N-二甲基胺基乙基)己二酸;脒,例如1,5-二氮雜雙環[4.3.0]壬烯(DBN)、1,8-二氮雜-雙環(5.4.0)十一-7-烯(DBU)和2,3-二甲基-3,4,5,6-四氫嘧啶;烷醇胺化合物,例如三乙醇胺、三異丙醇胺、N-甲基二乙醇胺、N-乙基-二乙醇胺、二甲基胺基乙醇和2-(N,N-二甲基胺基乙氧基)乙醇;N,N',N"-三-(二烷基胺基烷基)十六基氫三吖嗪,例如N,N',N"-三-(二甲基胺基丙基)-s-十六基氫三吖嗪、雙(二甲基胺基乙基)乙醚;及金屬鹽,例如以傳統的金屬氧化狀態形成之鐵、鉛、鉍、鋅及/或錫的無機及/或有機化合物,例如氯化
鐵(II)、氯化鐵(III)、2-乙基己酸鉍(III)、辛酸鉍(III)、新癸酸鉍(III)、氯化鋅、2-乙基己酸鋅、三氟甲磺酸鋅(II)、辛酸錫(II)、乙基己酸錫(II)、棕櫚酸錫(II)、二月桂基二丁基錫(IV)(DBTL)、二氯二丁基錫(IV)或辛酸鉛。
所使用的較佳催化劑為上述類型的三級胺、脒及錫化合物或鋅化合物。特佳的催化劑為1,4-二氮雜雙環-(2,2,2)-辛烷(DABCO)、1,5-二氮雜雙環[4.3.0]壬烯(DBN)、1,8-二氮雜雙環(5.4.0)十一-7-烯(DBU)及二月桂基二丁基錫(IV)(DBTL)和三氟甲磺酸鋅(II)。
上述實例提及的催化劑在反應中可獨立使用或以任意混合物的形式使用,其使用量(如果有的話)為從0.001至1.0重量%,較佳為從0.01至0.5重量%,以所使用催化劑總量佔所使用起始化合物的總量之百分比來計算。
可使用例如滴定分析法判定NCO含量以監控反應方法。當達到所需的NCO含量時,反應即結束。
按照此方式製造的式(I)之化合物為清澈、大致無色的產物,且按照所選起始材料,該化合物為低至高黏度液體且其單體起始二異氰酸酯的殘餘量低於1.0重量%,較佳為低於0.5重量%,特佳為低於0.3重量%,以反應產物的總質量為基準。
可藉由加入甲醇移除任何仍然可偵測到的殘餘NCO含量。
在按照本發明的製造過程中,為了避免式(I)的化合物之矽烷基過早交聯,建議添加水受體。例如,可使用原甲酸酯,例如三乙基原甲酸;乙烯基矽烷,例如乙烯基三甲氧基矽烷;或有機膦酸酯,例如二丁基膦酸酯。若有需要,所使用的水受體量最高達5重量%,較佳為最高達2重量%,以起始材料的總量為基準。
若使用催化劑及/或水受體,可在實際反應開始前將其加進起始化合物。然而,亦可在反應中的任何所需時點即時將此等輔助物質加進反應混合物。
在較佳的具體實例中,在此描述的方法會在氮等保護氣體環境下發生。
按照本發明,在此揭示之式(I)的經矽烷改質之聚合物可用於製造黏合劑和密封材料、塗漆、塗層、塗料、油墨及/或印刷油墨。
此方法的優點在於式(I)的經矽烷改質之聚合物的特性可經藉由改變所使用式Y-(NCO)m的結構而調整以用於各種不同的應用。
按照本發明,式(I)的化合物係用於反應性單組份黏合系統。反應性單組份黏合系統之特徵為包含至少一個式(I)的化合物。
在濕氣或水的作用下,矽烷基的可水解自由基會發生水解,然後隨著水解而產生矽烷的交聯(硬化)。
可伴隨地使用加速矽烷基水解及縮合的催化劑。此種催化劑係為熟習相關技術者所知悉。可使用例如酸,例如硫酸、對甲苯磺酸、三氟甲烷磺酸、乙酸、三氟乙酸和二丁基磷酸;鹼,例如N-取代脒,例如1,5-二氮雜雙環[4.3.0]壬5-烯(DBN)和1,5-二氮雜雙環[5.4.0]十一-7-烯(DBU),但亦可使用金屬鹽和金屬螯合物,例如四異丙基鈦酸、四丁基鈦酸、乙醯丙酮酸鈦(IV)、三仲丁醇鋁、乙醯丙酮酸鋁、三氟甲磺酸鋁或三氟甲磺酸錫。
若有的話,所使用的催化劑成份最高達5重量%,較佳為最高達2重量%,以所使用經矽烷改質之預聚合物的重量為基準。按照所使用催化劑的性質和重量,從按照本發明的式(I)之化合物製造的
單組份黏合系統會在廣泛的溫度範圍產生硬化,例如從-20至200℃,較佳為從0至180℃,特佳為從20至160℃。
作為反應配偶體選擇性加進按照本發明的反應性單組份黏合系統,亦可為任何所需的其他可水解矽烷化合物,例如四甲氧基矽烷、四乙氧基矽烷、甲基三甲氧基矽烷、甲基三乙氧基矽烷、乙基三乙氧基矽烷、異丁基三甲氧基矽烷、異丁基三乙氧基矽烷、辛基三乙氧基矽烷、辛基三甲氧基矽烷、(3-環氧丙基氧基丙基)-甲基二乙氧基矽烷、(3-環氧丙基氧基丙基)三甲氧基矽烷、苯基三甲氧基矽烷、苯基三乙氧基矽烷或US 4 499 150中所述類型的矽烷官能共聚合物,或是此等矽烷化合物的混合物。
本發明的反應性單組份黏合系統可同樣選擇性包含在先前技術中已知的其他添加劑及/或輔助物質。例如顏料、抗氧化劑、水受體、填充劑、助滑添加劑、助流劑、流變添加劑、泡沫安定劑、疏水劑、空氣孔隙形成劑、黏合強化添加劑(黏合促進劑)、配合劑、防老化劑、阻燃劑及/或紫外線安定劑。
作為適合填充劑,可以提及例如碳黑、沈澱矽石、熱解矽石、礦物白堊和熱解白堊。可以提及的適合塑化劑之實例為苯二甲酸酯、肥酸酯、苯酚的烷基磺酸酯、磷酸酯或高分子量的聚丙二醇。
作為水受體,特別是可以提及烷氧矽基化合物,例如乙烯三甲氧基矽烷、甲基三甲氧基矽烷、異丁基三甲氧基矽烷、十六基癸基三甲氧基矽烷。
作為黏合促進劑,使用已知的官能矽烷,例如上述類型的胺基矽烷,亦可為N-胺基乙基-3-胺基丙基-三甲氧基-及/或N-胺基乙基-3-胺基丙基甲基二甲氧基-矽烷、環氧基矽烷及/或巰基矽烷。
按照本發明的式(I)之化合物除了作為單組份黏合系統,亦可作為例如添加劑而加進一般單組份及/或雙組份聚尿烷黏合系統。
若將如上所述之按照本發明的反應性單組份黏合系統預先施加於待黏合的基板,則由於上述交聯,基板會產生永久黏合或密封。
對於待黏合的基板之表面,可能必須採用物理、化學及/或物理化學方法進行預處理。按照本發明,建議例如施加底膠或黏合促進劑成分,但此舉並非必要。因此,亦可在一具體實例中略過。
適合藉由按照本發明的反應性單組份黏合系統而進行黏結及/或密封的適合基板為金屬、玻璃、木頭、混凝土、石頭、陶瓷、紡織品及/或塑膠材料。待黏合的基板可為相同或不同。
在較佳的具體實例中,按照本發明的反應性單組份黏合系統係用於黏結及/或密封金屬、玻璃及/或塑膠材料。
適合的金屬基板通常可由相關領域常見的所有金屬或合金製造。較佳為使用鋁、不銹鋼、鋼、鈦、含鐵金屬及合金等金屬。待黏合的基板可另外由不同金屬構成。
待黏合的塑膠基板為例如聚碳酸酯(PC)、聚醯胺、聚氯乙烯、聚尿烷、聚乙酸乙烯酯、聚丙烯酸酯或聚丙烯酸甲酯、聚乙烯、聚苯乙烯、聚丙烯及/或聚酯,例如聚對苯二甲酸丁二酯(PBT)及/或聚對苯二甲酸乙二酯(PET)。
可對基板額外上漆或印刷。
待黏合的基板可進一步具有使用獲得的複合材料所需的的任何所需形式。基板最簡單的形式為平面。然而,亦可使用按照本發明的反應性單組份黏合系統黏合三維基板。
按照本發明亦提供一種複合材料,其藉由按照本發明的反應性單組份黏合系統而黏合,定義如上。
以下實例係用於說明本發明,但不應將其解讀成為專利保護範圍之限制。
除非另外說明,否則所有百分比皆與重量有關。
NCO成份係按照DIN EN ISO 11909採用滴定方式判定。
OH值係按照DIN 53240-2:2007-11採用滴定方式判定,酸值係按照DIN 3682 5判定。OH含量係從經由分析判定的OH值計算。
剩餘單體含量係按照DIN EN ISO 10283採用附內部標準的氣相層析進行量測。
分子量係按照DIN 55672-1採用膠透層析對照聚苯乙烯標準而決定(膠透層析(GPC)-第1部分:以四氫呋喃(THF)作為溶析液),差別在於所使用的流速為0.6毫升/分鐘,而非1.0毫升/分鐘。
所有黏度量測係按照DIN EN ISO 3219使用來自Anton Paar Germany GmbH(DE)的Physica MCR 51流變計來進行。
將1075.8克(6莫耳)的3-胺基丙基三甲氧基矽烷置於室溫下的
氮氣環境中,並放置於具有溫度計、KPG攪拌器、回流冷凝器和滴液漏斗的燒瓶。逐滴加入378.6克(6.3莫耳)的甲酸甲酯並加以攪拌,且溫度不超過50℃。當放熱反應消失,在室溫下繼續攪拌4個小時,然後在減壓環境下(0.1毫巴,50℃)蒸餾分離出多餘甲酸甲酯及獲得的甲醇。最後獲得黏度在23℃下為11mPa.s的無色液體。
將99.6克(0.6莫耳)的3-胺基丙基甲基二甲氧基矽烷置於室溫下的氮氣環境中,並放置於具有溫度計、KPG攪拌器、回流冷凝器和滴液漏斗的燒瓶。逐滴加入40.3克(0.67莫耳)的甲酸甲酯並加以攪拌,且溫度不超過50℃。當放熱反應消失,在室溫下繼續攪拌4個小時,然後在減壓環境下(0.1毫巴,50℃)蒸餾分離出多餘甲酸甲酯及獲得的甲醇。最後獲得無色液體。
將221.4克(1莫耳)的3-胺基丙基三乙氧基矽烷置於室溫下的氮氣環境中,並放置於具有溫度計、KPG攪拌器、回流冷凝器和滴液漏斗的燒瓶。逐滴加入77.8克(1.05莫耳)的甲酸乙酯並加以攪拌,且溫度不超過50℃。當放熱反應消失,在室溫下繼續攪拌4個小時,然後在減壓環境下(0.1毫巴,80℃)蒸餾分離出多餘甲酸乙酯及獲得的乙醇。最後獲得黏度在23℃下為13mPa.s的無色液體。
將497.9克(2.6莫耳)的3-胺基丙基甲基二乙氧基矽烷置於室溫下的氮氣環境中,並放置於具有溫度計、KPG攪拌器、回流冷凝器和滴液漏斗的燒瓶。逐滴加入212.1克(2.8莫耳)的甲酸乙酯並加以攪拌,且溫度不超過50℃。當放熱反應消失,在室溫下繼續攪拌
4個小時,然後在減壓環境下(0.1毫巴,80℃)蒸餾分離出多餘甲酸乙酯及獲得的乙醇。最後獲得無色液體。最後獲得黏度在23℃下為12mPa.s的無色液體。
將154.5克(0.915莫耳)的1,6-二異氰酸基己烷和25毫克(30ppm)的三氟甲磺酸鋅(II)置於60℃下的氮氣環境中,並放置於具有溫度計、KPG攪拌器、回流冷凝器和滴液漏斗的燒瓶。逐滴加入469.5克的聚丙二醇(OH值:112毫克KOH/克)和201克的聚乙醚(OH值:52毫克KOH/克)。在60℃下攪拌反應混合物直到達到固定的異氰酸酯含量(3.0重量%)。然後計量加入142.8克(0.69莫耳)的N-(3-三甲氧基矽烷基丙基)甲醯胺(來自實例1),在80℃下攪拌反應混合物直到再也無法使用滴定分析偵測到其他異氰酸酯含量為止。加入32毫克的二丁基磷酸酯使獲得的矽烷封端預聚合物安定,並加入2.14克的乙烯三甲氧基矽烷作為水受體。獲得的黏合劑為清澈無色物質且在23℃下黏度為21,000mPa.s。
將154.5克(0.915莫耳)的1,6-二異氰酸基己烷和25毫克(30ppm)的DBTL(二月桂基二丁基錫)置於60℃下的氮氣環境中,並放置於具有溫度計、KPG攪拌器、回流冷凝器和滴液漏斗的燒瓶。逐滴加入469.5克的聚丙二醇(OH值:112毫克KOH/克)和201克的聚乙醚(OH值:52毫克KOH/克)。在60℃下攪拌反應混合物直到達到固定的異氰酸酯含量(3.0重量%)。然後計量加入123.7克(0.69莫耳)的3-胺基丙基三甲氧基矽烷在80℃下攪拌反應混合物直到再也
無法使用滴定分析偵測到其他異氰酸酯成份為止。加入32毫克的二丁基磷酸酯使獲得的矽烷封端預聚合物安定,並加入2.14克的乙烯三甲氧基矽烷作為水受體。獲得的黏合劑為雲霧狀白濁物質且在23℃下黏度為100,000mPa.s。
將519.0克的Desmodur® N 75 BA(來自Bayer MaterialScience AG的聚異氰酸酯(溶於乙酸丁酯之以1,6-二異氰酸基己烷75%為基底的雙尿);異氰酸酯含量16.5重量%)連同50ppm的1,4-二氮雜雙環-(2,2,2)-辛烷置於80℃下的氮氣環境中,並放置於具有溫度計、KPG攪拌器、回流冷凝器和滴液漏斗的燒瓶。逐滴加入518.0克(2.8莫耳)的N-(3-三甲氧基矽烷基丙基)甲醯胺(來自實例1)並加以攪拌。當添加完成時,在80℃下攪拌反應混合物直到再也無法使用滴定分析偵測到其他異氰酸酯成份為止。最終黏合劑在23℃下黏度為6240mPa.s。
為了進一步處理,將黏合劑調整成含乙酸丁酯的50%固體成分,並加入來自BASF的0.25% Lupragen® N 700(1,8-二氮雜雙環-5,4,0-十一-7-烯);使用刀具將整體產物在玻璃板上平鋪成50微米的層厚度(濕)。在23℃且相對濕度為50%下乾燥4小時後,該塗層呈觸感乾燥,且經過4天後展現出對二甲苯、1-甲氧基-2-乙酸丙酯、乙酸乙酯和丙酮的良好溶劑抗性。
將578.0克的Desmodur® L75(來自Bayer MaterialScience AG的聚異氰酸酯(溶於乙酸乙酯之以1,6-二異氰酸基己烷75%為基底的雙尿);異氰酸酯成份為13.3重量%)連同50ppm的1,4-二氮雜雙環
-(2,2,2)-辛烷置於80℃下的氮氣環境中,並放置於具有溫度計、KPG攪拌器、回流冷凝器和滴液漏斗的燒瓶。逐滴加入522.0克(2.5莫耳)的N-(3-三甲氧基矽烷基丙基)甲醯胺(來自實例1)並加以攪拌。當添加完成時,在80℃下攪拌反應混合物直到再也無法使用滴定分析偵測到其他異氰酸酯成份為止。獲得的黏合劑在23℃下黏度為92,000mPa.s。
為了進一步處理,將黏合劑調整成含乙酸乙酯的50%固體成分,並加入來自BASF SE的0.25% Lupragen® N 700(1,8-二氮雜雙環-5,4,0-十一-7-烯);使用刀具將整體產物在玻璃板上平鋪成50微米的層厚度(濕)。在23℃且相對濕度為50%下乾燥4小時後,該塗層呈觸感乾燥,且經過4天後展現出對二甲苯、1-甲氧基-2-乙酸丙酯、乙酸乙酯和丙酮的良好溶劑抗性。
將201.6克(1.2莫耳)的1,6-二異氰酸基己烷置於80℃下的氮氣環境中,並放置於具有溫度計、KPG攪拌器、回流冷凝器和滴液漏斗的燒瓶,按比例加入87.6克(0.6莫耳)的2,2,4-三甲基戊烷-1,3-二醇。然後計量加入346克的乙酸丁酯作為溶劑以及52毫克的三乙基胺作為催化劑。當達到固定的異氰酸酯含量(8.2重量%),逐滴加入248.4克(1.2莫耳)的N-(3-三甲氧基矽烷基丙基)甲醯胺(來自實例1),並在80℃下攪動該批料直到再也無法使用滴定分析偵測到其他異氰酸酯成份為止。獲得的清澈黏合劑在固體成分50%下黏度為41mPa.s。
為了進一步處理,將來自BASF SE的0.25% Lupragen® N 700(1,8-二氮雜雙環-5,4,0-十一-7-烯)加進黏合劑,使用刀具將整體產物
在玻璃板上平鋪成50微米的層厚度(濕)。在23℃且相對濕度為50%下乾燥4小時後,該塗層呈觸感乾燥,且經過4天後展現出對二甲苯、1-甲氧基-2-乙酸丙酯、乙酸乙酯和丙酮的良好溶劑抗性。
將201.6克的1,6-二異氰酸基己烷置於80℃下的氮氣環境中,並放置於具有溫度計、KPG攪拌器、回流冷凝器和滴液漏斗的燒瓶,按比例加入87.6克(0.6莫耳)的2,2,4-三甲基戊烷-1,3-二醇。然後計量加入346克的乙酸丁酯作為溶劑以及52毫克的三乙基胺作為催化劑。當達到固定的異氰酸酯含量(8.2重量%),逐滴加入215.1克(1.2莫耳)的3-胺基丙基三甲氧基矽烷。開始添加作業後,即使進一步稀釋使固體成分低於50%,反應混合物亦會立即呈雲霧狀且該批料會在室溫下固化。無法進一步處理該批料作為漆黏合劑。
為了評估來自實例9的預聚合物之應用特性,以如下配方進行處理:
為了準備該配方,將填充劑(來自Solvay的Socal® U1S2)、塑化劑(來自Exxon的JayflexTM DINP)和乾燥劑(來自Evonik的Dynasylan® VTMO)加進黏合劑,使用附牆壁刮料器的真空溶解器以
3000轉/分進行攪拌。然後加入黏合促進劑(來自Evonik的Dynasylan® 1146),以1000轉/分攪拌5分鐘進行混合。最後,以1000轉/分攪拌催化劑(來自BASF SE的Lupragen® N700),最後再將完成的混合物暴露於真空環境下的空氣。
為了評估物理特性,按照DIN EN ISO 11600在玻璃板上準備厚度為2毫米的薄膜及測試樣品兩者。按照DIN 53505對薄膜測試蕭氏硬度。按照DIN EN ISO 11600在23℃下量測50%伸長率下的模數。
結果如下:
Claims (13)
- 一種通式(I)的化合物:
- 如申請專利範圍第1項的化合物,其中R2和R3相互獨立分別代表甲基或乙基。
- 如申請專利範圍第1或2項的化合物,其中Y代表分子自由基,其為由單異氰酸酯(m=1)、聚異氰酸酯(m>1)或含異氰酸酯基團 的預聚合物(m=從1至20)之m個NCO自由基所還原的結構單元,R1代表丙基,R2和R3相互獨立分別代表甲基或乙基,而n代表從0至2的整數。
- 一種製造式(I)的化合物之方法,包含使式(Ia)的化合物與式Y-(NCO)m的結構單元反應:
- 一種對如申請專利範圍第1至4項中任一項的化合物之用途,其係用於製造黏合劑和密封材料、塗漆、塗層、塗料、油墨及/或印刷油墨。
- 一種反應性單組份黏合系統,包含至少一種如申請專利範圍第1至5項中任一項的化合物。
- 一種如申請專利範圍第6項的反應性單組份黏合系統之用途,其係用於金屬、木頭、木頭為主材料、玻璃、皮革、紡織品、塑膠材料、礦物材料、軟木、纖維、混凝土、紙、硬紙板和薄膜之黏結及/或密封。
- 一種套組,其包含如申請專利範圍第6項的反應性單組份黏合系統,用於金屬、木頭、木頭為主材料、玻璃、皮革、紡織品、塑膠材料、礦物材料、軟木、纖維、混凝土、紙、硬紙板和薄膜之黏結及/或密封。
- 一種複合物,其係由如申請專利範圍第6項的反應性單組份黏合系統或如申請專利範圍第8項的套組所黏合。
- 一種反應性單組份塗層系統,包含如申請專利範圍第1至5項中任一項的至少一種化合物。
- 一種如申請專利範圍第10項的反應性單組份塗層系統之用途,其係用於金屬、木頭、木頭為主材料、玻璃、皮革、紡織品、塑膠材料、礦物材料、軟木、纖維、混凝土、紙、硬紙板和薄膜之塗層。
- 一種套組,其包含如申請專利範圍第10項的反應性單組份塗層系統,用於金屬、木頭、木頭為主材料、玻璃、皮革、紡織品、塑膠材料、礦物材料、軟木、纖維、混凝土、紙、硬紙板和薄膜之塗層。
- 一種複合物,其係由如申請專利範圍第10項的反應性單組份塗層系統或如申請專利範圍第12項的套組所黏合。
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EP3085719A1 (de) | 2015-04-21 | 2016-10-26 | Covestro Deutschland AG | Hydrophob modifizierter polyisocyanuratkunststoff und verfahren zu dessen herstellung |
JP6811726B2 (ja) | 2015-05-21 | 2021-01-13 | コベストロ、ドイチュラント、アクチエンゲゼルシャフトCovestro Deutschland Ag | ポリウレタンコーティング組成物 |
WO2020089019A1 (de) | 2018-10-30 | 2020-05-07 | Covestro Deutschland Ag | Verfahren zur herstellung eines mehrschicht-lackaufbaus mit einer deckschicht aus silangruppen-enthaltenden prepolymeren |
US20210346912A1 (en) | 2018-10-30 | 2021-11-11 | Covestro Intellectual Property Gmbh & Co. Kg | Multi-layer paint structure with improved layer adhesion |
CN112812680A (zh) * | 2021-01-26 | 2021-05-18 | 广东爱上体育产业股份有限公司 | 一种强渗透型提升水泥混凝土强度的密封底漆及其制备方法 |
Family Cites Families (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4499150A (en) | 1983-03-29 | 1985-02-12 | Ppg Industries, Inc. | Color plus clear coating method utilizing addition interpolymers containing alkoxy silane and/or acyloxy silane groups |
DE3524215A1 (de) | 1985-07-06 | 1987-01-08 | Degussa | N-silylpropyl-n'-acyl-harnstoffe und verfahren zur herstellung |
DE4308097A1 (de) | 1993-03-15 | 1994-09-22 | Henkel Kgaa | Polyol für ein Isocyanat-Gießharz und Beschichtungen |
DE19646424A1 (de) | 1996-11-11 | 1998-05-14 | Henkel Kgaa | Verwendung von Polyolen für Isocyanat-Gießharze und -Beschichtungsmassen |
DE102007032666A1 (de) * | 2007-07-13 | 2009-01-22 | Bayer Materialscience Ag | Allophanat- und Silangruppen enthaltende Polyisocyanate |
US8058463B2 (en) * | 2007-12-04 | 2011-11-15 | E. I. Du Pont De Nemours And Compnay | Fluorosilanes |
DE102009033636A1 (de) * | 2009-07-17 | 2011-01-20 | Bayer Materialscience Ag | Formamide enthaltende Reaktivsysteme |
DE102009047964A1 (de) * | 2009-10-01 | 2011-04-21 | Bayer Materialscience Ag | Hochfunktionelle Allophanat- und Silangruppen enthaltende Polyisocyanate |
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- 2015-01-26 WO PCT/EP2015/051439 patent/WO2015113919A1/de active Application Filing
- 2015-01-26 CN CN201580006602.0A patent/CN105934437B/zh not_active Expired - Fee Related
- 2015-01-26 US US15/112,326 patent/US10040808B2/en not_active Expired - Fee Related
- 2015-01-26 JP JP2016549107A patent/JP6532473B2/ja not_active Expired - Fee Related
- 2015-01-26 EP EP15702206.2A patent/EP3099698B1/de not_active Not-in-force
- 2015-01-29 TW TW104102943A patent/TW201540739A/zh unknown
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EP3099698A1 (de) | 2016-12-07 |
ES2651918T3 (es) | 2018-01-30 |
CN105934437A (zh) | 2016-09-07 |
JP2017506679A (ja) | 2017-03-09 |
CN105934437B (zh) | 2019-03-01 |
EP3099698B1 (de) | 2017-09-13 |
US20160340372A1 (en) | 2016-11-24 |
US10040808B2 (en) | 2018-08-07 |
WO2015113919A1 (de) | 2015-08-06 |
JP6532473B2 (ja) | 2019-06-19 |
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