CN111194329A - 包含反应性阻燃剂的刚性聚氨酯泡沫 - Google Patents
包含反应性阻燃剂的刚性聚氨酯泡沫 Download PDFInfo
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- CN111194329A CN111194329A CN201880049383.8A CN201880049383A CN111194329A CN 111194329 A CN111194329 A CN 111194329A CN 201880049383 A CN201880049383 A CN 201880049383A CN 111194329 A CN111194329 A CN 111194329A
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- China
- Prior art keywords
- insulation
- carbon atoms
- polyol
- flame retardant
- rigid polyurethane
- 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.)
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- 150000001412 amines Chemical class 0.000 description 5
- KTLIMPGQZDZPSB-UHFFFAOYSA-N diethylphosphinic acid Chemical compound CCP(O)(=O)CC KTLIMPGQZDZPSB-UHFFFAOYSA-N 0.000 description 5
- 150000002334 glycols Chemical class 0.000 description 5
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 239000003960 organic solvent Substances 0.000 description 5
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 5
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- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 4
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- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
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- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
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- RXPQRKFMDQNODS-UHFFFAOYSA-N tripropyl phosphate Chemical compound CCCOP(=O)(OCCC)OCCC RXPQRKFMDQNODS-UHFFFAOYSA-N 0.000 description 1
- CQXYINNETWHZTR-UHFFFAOYSA-N tritert-butyl phosphate Chemical compound CC(C)(C)OP(=O)(OC(C)(C)C)OC(C)(C)C CQXYINNETWHZTR-UHFFFAOYSA-N 0.000 description 1
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Classifications
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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
- 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
- C08G18/2805—Compounds having only one group containing active hydrogen
- C08G18/2815—Monohydroxy compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/49—Phosphorus-containing compounds
- C08K5/51—Phosphorus bound to oxygen
- C08K5/53—Phosphorus bound to oxygen bound to oxygen and to carbon only
- C08K5/5313—Phosphinic compounds, e.g. R2=P(:O)OR'
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B65—CONVEYING; PACKING; STORING; HANDLING THIN OR FILAMENTARY MATERIAL
- B65D—CONTAINERS FOR STORAGE OR TRANSPORT OF ARTICLES OR MATERIALS, e.g. BAGS, BARRELS, BOTTLES, BOXES, CANS, CARTONS, CRATES, DRUMS, JARS, TANKS, HOPPERS, FORWARDING CONTAINERS; ACCESSORIES, CLOSURES, OR FITTINGS THEREFOR; PACKAGING ELEMENTS; PACKAGES
- B65D83/00—Containers or packages with special means for dispensing contents
- B65D83/14—Containers or packages with special means for dispensing contents for delivery of liquid or semi-liquid contents by internal gaseous pressure, i.e. aerosol containers comprising propellant for a product delivered by a propellant
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Abstract
本发明提供经阻燃的刚性聚氨酯泡沫,其包括多元醇和异氰酸酯泡沫形成组分、以及作为阻燃剂的二烷基含磷化合物(即反应性单羟基官能的二烷基次膦酸酯)的反应产物,所述二烷基含磷化合物在所述刚性聚氨酯泡沫中起到作为高效的反应性阻燃剂的作用。
Description
相关申请的交叉引用
本申请要求2017年7月24日提交的序列号62/536,260的美国临时专利申请的权益,该美国临时专利申请的全部内容并入本文中作为参考。
技术领域
本公开提供反应性二烷基含磷化合物(即羟基官能的二烷基次膦酸酯)的使用,该化合物当与多元醇和异氰酸酯反应时在刚性聚氨酯泡沫(泡沫体,foam)中充当高效的反应性阻燃剂。本发明进一步提供所述羟基官能的二烷基次膦酸酯反应并引入到刚性聚氨酯泡沫的聚合物基体中的经阻燃的聚氨酯刚性泡沫。措辞“耐火剂”和“阻燃剂”在本文中可互换地使用。
背景技术
溴化的或基于磷的阻燃剂已知为高度有效的,并且在很多情形中是用于降低合成材料例如刚性聚氨酯泡沫的火灾风险的唯一选项。然而,多年来,与日俱增的公众和政府对化学品(和特别地阻燃剂)的监督力度一直在增加。目标是朝向更加可持续的、反应性的、聚合的和/或无卤素的新产品。如果阻燃剂反应到聚合物基体中并无法浸出,则监督力度将大为减弱。
因此,对于具有这样的特征的用于刚性聚氨酯的反应性含磷耐火剂存在需求:高的磷含量、澄清(透明,clear)的浅色、以及良好的与在聚氨酯工业中使用的聚醚多元醇和聚酯多元醇的相容性。
发明内容
本发明提供一种刚性聚氨酯泡沫,其包括反应性的二烷基含磷单羟基官能的化合物阻燃剂,所述阻燃剂拥有高度令人满意的阻燃特性并具有良好的与刚性聚氨酯泡沫形成用体系的多元醇组分的相容性。应理解,如本文中使用的措辞“刚性聚氨酯泡沫形成用体系”包括多元醇、异氰酸酯、如本文中所述的单羟基官能的二烷基次膦酸酯化合物。所述单羟基官能的二烷基次膦酸酯化合物通过其单羟基官能团而具有充分的反应性,并且比二-或三-羟基官能的二烷基次膦酸酯化合物可更容易配制(formulate)。已经预料不到地发现,本文中的反应性单羟基官能的二烷基次膦酸酯化合物尽管其羟基官能团的含量较低,但例如通过与刚性聚氨酯泡沫形成用体系的异氰酸酯组分进行反应可反应并引入到刚性聚氨酯泡沫的聚合物结构中,而不破坏刚性聚氨酯泡沫的性质。这意味着,本发明阻燃剂被整合(集成)到刚性泡沫基质中,使得它不释放到环境中并不太可能渗透通过活组织细胞膜,并因此不造成健康危害。本发明进一步提供上述的刚性聚氨酯泡沫形成用体系,其包括但不限于本文中所述的反应性二烷基含磷单羟基官能的化合物。
如本文中使用的术语“聚氨酯”理解为包括聚氨酯和聚异氰脲酸酯两种材料。本领域技术人员能够在聚氨酯材料和聚异氰脲酸酯材料之间进行区分并且在本文中将不讨论所述区别。
如本文中使用的术语“泡沫”指的是刚性、半刚性和单组分(OCF)聚氨酯和聚异氰脲酸酯泡沫。作为包括经反应的通式(I-A)和/或(I-B)的单羟基官能的二烷基次膦酸酯化合物、基本上由其组成、或由其组成的本文中描述的(或本文中请求保护的)刚性聚氨酯泡沫在本文中均被理解为包含前述式作为反应性材料,即前述式反应到刚性聚氨酯材料的结构中,在该情形中前述式可不或将不以如本文中所述的相同结构式存在,而将作为二醇和/或多元醇、异氰酸酯和本文中所述结构式的反应产物存在于刚性聚氨酯材料中,其中通式(I-B)代表包含至少一个含磷基团的多醇经部分磷酰化(磷酸化,phosphorylation)的含磷二醇和/或多元醇反应产物的组。
将理解,如本文中使用的术语“刚性的”包括以聚氨酯和聚异氰脲酸酯配制剂形式的刚性泡沫、半刚性泡沫和单组分泡沫。
将理解,如本文中使用的术语“多元醇”也可能定义为二醇和/或多元醇。
如本文中使用的措辞“单组分泡沫”(OCF)被理解为如下的现场(原位,in-situ)聚氨酯泡沫(DIN 18159):其是湿气(水分)固化性的,并且容纳在加压容器中、优选地在一次性加压容器(气溶胶罐)中且可包括多元醇、异氰酸酯和如本文中所述的阻燃剂或阻燃剂共混物。聚氨酯的OCF可在建筑行业中用于密封、隔离体和组装意图,例如在涉及密封接缝、屋顶表面、窗和门方面使用,但不限于此。
在一个实施方式中,所述OCF可由异氰酸酯预聚物制备,所述异氰酸酯预聚物又由多元醇与有机二异氰酸酯和/或多异氰酸酯在泡沫稳定剂和催化剂以及任选的增塑剂、本文中所述的阻燃剂和其它添加剂的存在下反应而制备。OCF反应进行的反应在加压容器中在液化气存在下发生。在所述预聚物形成之后,可将泡沫以经计量的量通过阀门排出。所述泡沫具有乳脂状稠度并在例如来自空气的环境水分的作用下固化,在该过程中经历体积增大(单组分泡沫)。在刚要施加所述泡沫之前,还可从另外的加压容器添加活化剂。所述活化剂提供较快的泡沫无粘固化(双组分泡沫)。所述活化剂可为短链二醇,例如乙二醇、丙二醇、丁烷-1,4-二醇或甘油。
本发明的阻燃剂共混物提供阻燃有效量的(A)通式(I-A)和(I-B)的单羟基官能的二烷基次膦酸酯化合物、和通式(I-B)的包含至少一个含磷基团的多醇部分磷酰化的含磷二醇和/或多元醇反应产物的组,其中式(I-A)为:
其中:
R1和R2选自包含1至4个碳原子的线型或支化的烷基,例如甲基、乙基、丙基、异丙基、丁基和异丁基,优选地甲基或乙基,更优选地R1和R2两者均为乙基;和,
k可为0或1;
R3选自氢,包含2至约8个碳原子、优选地2至4个碳原子的单羟基封端的线型或支化的亚烷基;和,
前提是当k为零时,R3为单羟基封端的线型或支化的亚烷基,且当k为1时,R3为氢,和
当X为时,R4和R5各自独立地选自H,包含1至8个碳原子、优选地1至约4个碳原子的线型或支化的烷基和最优选地甲基、乙基或丙基的任一者,包含2至8个碳原子、优选地2至约4个碳原子的线型或支化的烯基,包含1至8个碳原子的经卤素取代的烷基,包含1至8个碳原子、优选地1至约4个碳原子的烷氧基,包含6至12个碳原子、优选地6至约8个碳原子的芳基,和包含7至16个碳原子、优选地7至约12个碳原子的烷基芳基,或者R4和R5彼此成键而形成包含4至约8个碳原子、优选地6个碳原子的环烷基;和其中式(I-B)为:
其中:
R1和R2独立地选自包含1至4个碳原子的线型或支化的烷基,例如选自甲基、乙基、丙基、异丙基、丁基和异丁基,优选地甲基或乙基,更优选地R1和R2两者均为乙基;和,
n1为等于或大于1的整数且n2为一,优选地n1为约1至约5,和
Z2为源自二醇或多元醇的化合价为n1+n2的部分并且具有如下通式:
其中R选自:
和其中各R6独立地为H或为1至4个碳原子的烷基,x为0或≥1、优选地1至4、更优选地x=1,y为2或3;z为2至5的整数;且,m≥1、优选地m=1。
本文中还提供用于制备这些化合物的方法。
式(I-A)的化合物可通过式(II)的单羟基官能的二烷基次膦酸与具有氧杂环丙烷基团的化合物的反应而制备,其中式(II)为:
其中R1和R2为所定义的。
式(I-A)的化合物还可通过式(III)的二烷基次膦酰卤与脂族二醇的反应而制备,其中式(III)为:
和其中R1和R2为所定义的,且A为氯或溴。
本发明的含磷的二醇和/或多元醇,例如式I-B的那些,可通过式(III)的二烷基次膦酰卤与脂族二醇和/或多元醇的反应而制备。
本发明的反应性单羟基官能的二烷基次膦酸酯拥有高的磷含量,具有良好的水解和热稳定性,展现良好的与刚性聚氨酯泡沫形成用体系的二醇和/或多元醇组分的相容性,并且在刚性聚氨酯泡沫中可作为高效的反应性阻燃剂使用。
本发明进一步提供经阻燃的刚性聚氨酯,其包括所述含磷的单羟基官能的化合物在于刚性聚氨酯泡沫形成用体系中反应而形成刚性聚氨酯泡沫之后的反应性残基。本文中的含磷的单羟基官能的化合物可单独地或者以与彼此之间的预混物和/或与其它阻燃剂(包括含卤素阻燃剂和含磷阻燃剂)的预混物的形式在刚性聚氨酯泡沫形成用体系中使用。
本发明所有以上和其它特征和优势藉由下面的其优选实施方式的说明性且非限制性的详细描述将更好地被理解。
优选实施方式的详细描述
在一个实施方式中,式(I-A)的单羟基官能的二烷基次膦酸酯可为更具体的式(I-A-1)或(I-A-2)的那些,其中式(I-A-1)为:
其中R1和R2、Z、k和R3如上定义;和,
其中式(I-A-2)为:
和其中R1、R2、R4和R5如上定义。
在本文中的一个实施方式中,本发明的式(I-A)的单羟基官能的二烷基次膦酸酯通过式(II)的二烷基次膦酸与式(IV)的具有氧杂环丙烷基团的化合物的反应而制备,该式(IV)为
其中:
R4和R5如上定义。
在本文中的一个其它实施方式中,本发明的式(I-A)的单羟基官能的二烷基次膦酸酯通过式(III)的二烷基次膦酰卤与式(V)的脂族二醇的反应而制备:
HO-(Z)K-R3 (V)
其中Z、R3和下标k如上定义。
本发明的含磷的二醇和/或多元醇,例如式(I-B)的那些,通过式(III)的二烷基次膦酰卤与脂族二醇或多元醇的反应而制备。
在本发明方法中作为初始材料使用的二烷基次膦酸(II)和二烷基次膦酰卤(III)在本领域中多半是公知的。式(II)的化合物可例如通过相应的二烷基次膦酰卤(III)的水解而获得。后者可例如通过美国专利No.3,104,259中记载的方法制备,该美国专利的全部内容并入本文中作为参考。
在用于制备本发明的式(I-A)或者更特别地(I-A-1)或(I-A-2)的化合物的方法中使用的具体的氧杂环丙烷化合物选自但不限于例如环氧乙烷、环氧丙烷、1,2-环氧丁烷、1,2-环氧戊烷、1,2-环氧己烷、1,2-环氧-5-己烯、1,2-环氧-2-甲基丙烷、1,2-环氧辛烷、缩水甘油基甲基醚、缩水甘油基异丙基醚、缩水甘油基异丁基醚、缩水甘油基庚基醚、缩水甘油基2-乙基己基醚、缩水甘油基烯丙基醚、三羟甲基丙烷三缩水甘油基醚、氧化苯乙烯、氧化环己烯、表氯醇、及其组合。更优选地,使用环氧乙烷、环氧丙烷和1,2-环氧丁烷作为所述氧杂环丙烷化合物。
在用于制备本发明的式(I-A)或更特别地(I-A-1)或(I-A-2)的化合物的方法中使用的具体的脂族二醇选自但不限于例如乙二醇、一缩二乙二醇、二缩三乙二醇、丙二醇、一缩二丙二醇、二缩三丙二醇、1,3-丙烷二醇、1,4-丁烷二醇、2-丁烯-1,4-二醇、1,5-戊烷二醇、1,6-己烷二醇、1,8-辛烷二醇和分子量至多为700的其它二醇。
在用于制备本发明的含磷的多元醇的方法中使用的脂族二醇和/或多元醇通常可为分别具有至少两个或至少三个反应性氢原子的任意适合的二醇和/或多元醇,实例为具有2或3到6(优选地2、3和4)的官能度和优选地约100至约700的分子量的那些。具体的脂族二醇和/或多元醇可选自非聚合物多醇例如三羟甲基丙烷、三羟甲基乙烷或甘油。
优选地,根据本发明使用的二醇和/或多元醇为聚醚二醇和/或多元醇。这类二醇和/或多元醇通过一种或多种环氧烷烃(例如环氧乙烷和环氧丙烷)与包含一个或多个活性氢原子的适合反应物(例如醇、胺和酸)的开环加成反应而获得;更特别地,所述反应物可选自二醇、三醇、酚醛树脂、季戊四醇、山梨糖醇、蔗糖、二亚乙基三胺等。聚酯多元醇也可根据本发明使用;这类多元醇通过羧酸、二羧酸(或多羧酸)(例如己二酸、苯二甲酸等)与二醇或三醇的缩合反应而获得。在用于制备本发明的含磷的单醇、二醇或多元醇的方法中使用的脂族二醇和/或多元醇选自聚合物二醇和/或多元醇例如聚醚多元醇、聚酯多元醇及其混合物。
在与单羟基二烷基次膦酸(II)的反应中使用的氧杂环丙烷化合物的量为相对于单羟基二烷基次膦酸而言5-300%摩尔过量、和优选地50-100%摩尔过量。使用相对于单羟基二烷基次膦酸而言大于100%摩尔过量的氧杂环丙烷化合物因需要回收大量的氧杂环丙烷而并非明智的。
取决于参与所述反应的二烷基次膦酸和氧杂环丙烷,本发明的式(I-A)或更特别地(I-A-1)或(I-A-2)的单羟基官能的二烷基次膦酸酯具有约8-18重量%的磷含量和约150-315mg KOH/g的羟值。
对于具有尽可能高的磷含量的目标单羟基官能的二烷基次膦酸酯(I-A)或更特别地(I-A-1)或(I-A-2)的制备,使单羟基二烷基次膦酸(II)中具有最高磷含量的单羟基-二烷基次膦酸与环氧乙烷和环氧丙烷反应是优选的。
因此,具有特别有价值的性质的式(I-A)或更特别地(I-A-1)或(I-A-2)的化合物为其中R1和R2各自为乙基的那些。
所述反应在40℃至120℃之间、和优选地在70℃至90℃之间的温度进行。在低于40℃的温度下,所述反应变得不可接受地慢。另一方面,应用高于120℃的温度是不建议的,因为在这样的温度下可形成不期望的分解产物。
在一种优选实施方式中,二烷基次膦酰卤(III)与脂族二醇的反应在过量二醇的介质中进行。
在与二烷基次膦酰卤(III)的反应中使用的二醇化合物的量通常为每1摩尔二烷基次膦酰卤2至10摩尔、和优选地4至8摩尔的摩尔过量。需要相对大的过量的所述二醇以使不期望的甘醇和二醇的不具有羟基的双(二烷基次膦酸酯)的形成最少化。使用每1摩尔二烷基次膦酰卤大于10摩尔的摩尔过量的二醇化合物因需要回收大量二醇而并非明智的。
取决于参与所述反应的二烷基次膦酰卤和二醇,本发明的式(I-A)或更特别地(I-A-1)或(I-A-2)的单羟基官能的二烷基次膦酸酯具有约2-18重量%的磷含量和约150-450mg KOH/g的羟值。
对于具有尽可能高的磷含量的目标单羟基官能的二烷基次膦酸酯(I-A)或更特别地(I-A-1)或(I-A-2)的制备,使二烷基次膦酰卤(III)中具有最高磷含量的二烷基次膦酰卤与乙二醇反应是优选的。
因此,具有特别有价值的性质的式(I-A-1)的化合物是其中R1和R2各自为乙基,k为1,n为1,Y为–CH2CH2–,且R3为氢的化合物。
所述反应在25℃至120℃之间、和优选地在50℃至90℃之间的温度进行。施加低于25℃的温度导致低的产率。另一方面,施加高于120℃的温度是不建议的,因为在这样的温度下可形成不期望的分解产物。另外,为加快反应可使用催化剂例如MgCl2或ZnCl2。
在一种优选实施方式中,二烷基次膦酰卤(III)与脂族二醇的反应在强碱例如氢氧化钠或氢氧化钾存在下在有机溶剂和过量脂族醇两者的介质中进行。所述有机溶剂选自芳族化合物。尤其适合的芳族溶剂为氯苯、邻二氯苯、均三甲苯、以及特别地甲苯和二甲苯。在所述方法中使用的碱的有效量在每1摩尔二烷基次膦酰卤(III)1-1.2摩尔、和优选地1-1.05摩尔的范围中。
氢氧化钠或钾可以固体形式使用。由所述二醇和所述碱之间的反应产生的水应在加入二烷基次膦酰卤(III)之前尽可能地从反应混合物中除去。
在一种优选实施方式中,二烷基次膦酰卤(III)与脂族二醇和/或多元醇的反应通过改变所述二醇和/或多元醇的部分磷酰化的程度而实施。根据本发明的含磷的二醇和/或多元醇包含至少一个含磷基团。该含磷基团为式(III-A)的基团:
其中:
其中R1和R2为所定义的,和其中波浪线表示经由氧原子与二醇或多元醇的键。
本发明的含磷的二醇和/或多元醇还可包括两个或更多个式(III-A)的含磷基团,其中这些含磷基团可相同或不同。
二烷基次膦酰卤(III)与脂族二醇和/或多元醇的反应可在有机碱存在下进行,所述有机碱选自但不限于叔胺例如三乙胺、吡啶、二异丙基乙基胺、1-甲基咪唑。碱的用量与二烷基次膦酰卤(III)是等摩尔的。所述碱也可相对于二烷基次膦酰卤过量使用。所述反应典型地在惰性有机溶剂介质中进行。对于磷酰化适合的溶剂为但不限于卤化烃,例如二氯甲烷、氯仿或1,2-二氯乙烷。另外的适合溶剂为醚例如二烷或四氢呋喃。另外的适合溶剂为烃例如己烷或甲苯。
在一种优选实施方式中,二烷基次膦酰卤(III)与脂族二醇和/或多元醇的反应在强的无机碱例如氢氧化钠或氢氧化钾存在下在有机溶剂例如氯苯、均三甲苯以及特别地甲苯和二甲苯的介质中进行。
在所述方法中使用的所述碱的有效量在每1摩尔二烷基次膦酰卤(III)1-1.2摩尔、和优选地1-1.05摩尔的范围内。氢氧化钠或钾可以固体形式使用。由所述二醇和/或多元醇与所述碱之间的反应产生的水应在加入二烷基次膦酰卤(III)之前尽可能地从所述反应混合物中除去。
可调节二烷基次膦酰卤(III)和二醇和/或多元醇的量,使得达到期望的官能化程度。二醇和/或多元醇的部分磷酰化可通过使用二烷基次膦酰卤(III)对二醇和/或多元醇的基于其官能度的小于化学计量的量而实现。通过该方式,二醇和/或多元醇中OH基团的仅一部分与二烷基次膦酰卤反应。
本发明的含磷的二醇和/或多元醇(在本文中也记为部分磷酰化的二醇和/或多元醇)具有1的残留平均OH-官能度(在其磷酰化之后)和约200至约1000的分子量。取决于参与所述反应的二烷基次膦酰卤和二醇和/或多元醇以及它们之间的摩尔比,本发明的含磷的二醇和/或多元醇具有约4-20重量%的磷含量和约20-800mg KOH/g的羟值。
二醇和/或多元醇的磷酰化反应在0℃至100℃之间、和优选地在10℃至90℃之间的温度进行。施加低于0℃的温度导致低的反应速率。另一方面,施加高于100℃的温度是不建议的,因为在这样的温度下,可形成不期望的分解产物。
本发明的单羟基官能的二烷基次膦酸酯化合物可用作反应性阻燃剂。在一个非限制性实施方式中,将磷酯(含磷酯,phosphorus ester)化合物与本发明的单羟基官能的二烷基次膦酸酯化合物组合可为有用的。磷酯的一些非限制性实例为磷酸三乙酯、磷酸三丙酯、磷酸三异丙酯、磷酸三丁酯、磷酸三叔丁基酯、磷酸三(2-乙基己基)酯、磷酸三辛基酯、甲基膦酸二甲酯、丙基膦酸二甲酯、乙基膦酸二乙酯、羟甲基膦酸二乙酯、N,N-双(2-羟乙基)氨基甲基膦酸二乙酯、磷酸三(氯丙基)酯、磷酸三(二氯丙基)酯、磷酸芳基/烷基酯、磷酸三芳基酯、双磷酸酯、低聚磷酸酯、及其组合。
对于刚性聚氨酯泡沫,将本发明的羟基官能的二烷基次膦酸酯任选地与包含羟基的溴化产品一起使用是优选的,而对于聚异氰脲酸酯泡沫,不使用卤化阻燃剂是优选的。
如本文中所述的阻燃剂或阻燃剂共混物可原样地、或者作为与卤化或非卤化产品的混合物使用。更优选的是,羟基官能的二烷基次膦酸酯或其与磷酸酯的共混物与包含羟基的反应性溴化产品组合的组合物。对于刚性聚氨酯(PU)泡沫,优选地使用与溴化产品的混合物,而对于聚异氰脲酸酯(PIR)泡沫,优选地使用纯产物。
根据本发明与羟基官能的二烷基次膦酸酯组合使用的优选的溴化阻燃剂包括由式(VI)表示的一种或多种三溴苯酚封端的化合物
其中:
n为范围在0至5之间的、和更优选地范围在0至4之间的整数。
这样的化合物还可成功地溶解在羟基官能的二烷基次膦酸酯(本发明提供的液体组合物)中而不改变该组合物的稳定性,使得所得组合物在环境温度下在长的储存期内保持溶液形式。市售的式(VI)的三溴苯酚封端的化合物由Dead Sea Bromine Group以商品名称F-3014生产。
羟基官能的二烷基次膦酸酯相对于所述组合物的总重量的重量浓度优选地在10-60%之间、和更优选地在20-40%之间。
还已经发现,室温下为固体的三溴新戊基醇,一种由式(VII)的结构表示的阻燃剂,也可成功地溶解在羟基官能的二烷基次膦酸酯(本发明提供的液体组合物)中而不改变该组合物的稳定性,使得所得组合物在环境温度下在长的储存期内保持溶液形式:
优选地,三溴新戊醇的重量浓度在10-60%之间的范围内、和更优选地在20-40%之间的范围内,相对于所述组合物的总重量。三溴新戊醇可以商品名称FR-513购自Dead Sea Bromine Group。
本发明组合物尤其地可用作聚氨酯和聚异氰脲酸酯泡沫的阻燃剂。如上解释的,本发明提供的液体组合物为包含与如下组合的式(I-A、或更特别地(I-A-1)或(I-A-2))或者(I-B)的羟基官能的二烷基次膦酸酯的溶液:与式(VI)的化合物或另行地与三溴新戊醇(VII))、和优选地作为式(I-A、或更特别地(I-A-1)或(I-A-2))或者(I-B)的羟基官能的二烷基次膦酸酯的溶质的式(VI)和式(VII)化合物两者,并且因此可直接地加入到用于制备聚氨酯和聚异氰脲酸酯泡沫的反应物的液态混合物,于是所述混合物的共混操作被相当大地简化并且在所述混合物中容易地获得待反应的组分的均匀分布。
在本文中的另一实施方式中,溴化阻燃剂选自溴化双酚A化合物、溴化双酚S化合物、溴化双酚F化合物、溴化双酚A碳酸酯低聚物、溴化双酚A环氧树脂、封端的溴化双酚A环氧树脂、脂族溴化醇和二醇类、二溴新戊二醇、溴化苯二甲酸酯和四溴苯二甲酸酯二醇、溴化磷酸酯、溴化酚、溴化苯二甲酸、及其组合。
根据本发明使用的溴化阻燃剂的量取决于在聚氨酯泡沫所需的阻燃程度和物理性质之间的关系而变化。然而,溴化阻燃剂通常以基于100重量份聚氨酯泡沫1至50重量份的量使用。在量小于1重量份中,无法赋予期望的阻燃性。超过50重量份的量带来足够的阻燃性但可损害所得泡沫的成型或成形产品的物理性质。因此,在上述范围外的量是不优选的。从在阻燃性和物理性质之间保持良好平衡的观点看,所述量在实践中落在3至30份的范围内。取决于最终用途应用,可组合使用两种或更多种溴化阻燃剂。
因此,本发明的阻燃剂组合物可作为如下的预制浓缩物使用:其(通过连续、不连续或喷雾方法)可加入到适于获得刚性聚氨酯泡沫或聚异氰脲酸酯泡沫的标准配制剂。
在另一方面中,本发明提供羟基官能的二烷基次膦酸酯(I-A)或更特别地(I-A-1)或(I-A-2)或者I-B与卤化或非卤化产品(或两者)的组合物。
本发明的阻燃剂组合物中通式I-A中式(I-A-1)或(I-A-2)的化合物和其它产品之间的重量比在1:9至9:1之间、和更优选地在30-70%之间。溴化阻燃剂例如三溴新戊醇(FR-513)和由式(VI)表示的三溴苯酚封端的化合物可包括在本发明组合物中,使得本发明的阻燃剂组合物中本发明的羟基官能的二烷基次膦酸酯、三溴新戊醇(VII)和由式(VI)表示的三溴苯酚封端的化合物的重量浓度分别地在10-50wt%、10-50wt%和10-50wt%的范围内。
在一个实施方式中,提供式(I-A)、(I-A-1)、(I-A-2)或(I-B)的单羟基官能的二烷基次膦酸酯与如本文中所述的磷酸酯化合物的阻燃剂共混物,使得羟基官能的二烷基次膦酸酯和磷酸酯组分(如果存在的话)与包含羟基的反应性溴化产品(例如上述的非限制性实例)共混。
本发明的单羟基官能的二烷基次膦酸酯化合物当单独地或与磷酸酯化合物一起引入到刚性聚氨酯泡沫中时为高效的反应性阻燃剂。应注意,本发明的阻燃剂共混物可在宽的异氰酸酯指数(在本文中缩写为MDI或TDI)内使用。该指数指的是在配制剂中实际使用的异氰酸酯相对于理论上需要的异氰酸酯的化学计量的量的以百分数表示的比率。
本文中的刚性聚氨酯泡沫包含典型的阻燃有效量的阻燃剂(即单羟基官能的二烷基次膦酸酯)。典型地,以提供聚合物(即刚性聚氨酯泡沫)中的总磷浓度为在基于所述聚合物的总重量的0.3至15wt%范围内的量施加所述次膦酸酯。优选地,所述聚合物中的总磷浓度在1至10wt%的范围内、和更优选地在1.5至5wt%的范围内,基于刚性聚氨酯聚合物的总重量。最优选地,本发明的次膦酸酯的用量至少对于符合DIN 4102B2测试和/或LOI易燃性测试方法的现行要求是足够的。
除刚性泡沫外,还存在另一种可用类型的泡沫,其通常归类为半刚性,其在本文中归类到刚性的概括性总定义内。作为汽车乘客舱和其它地方中的冲击吸收用材料使用的所述刚性和半刚性泡沫通常通过使多异氰酸酯与泡沫多元醇和交联剂例如三羟甲基丙烷的混合物反应而制成。
尽管所有的聚氨酯泡沫(刚性或半刚性)的制造均涉及在异氰酸酯基团和羟基基团之间相同的基本化学反应,但是各类型的泡沫向制造者呈现的问题却不同。该差异常常与必须总是在气体产生和聚合物凝胶化之间实现的平衡有关。这些问题的很多可通过适当地选择辅助剂例如发泡剂、催化剂、表面活性剂、泡沫稳定剂等而至少部分地解决。
如本文中使用的刚性聚氨酯泡沫由官能度高至8的较高度支化的较低当量重量的聚醚/聚酯多元醇制成。与在柔性泡沫中相比,在刚性聚氨酯泡沫中需要较高浓度的芳族多异氰酸酯。通过本发明方法可获得的刚性聚氨酯泡沫优选地具有10-50kg/m3、更优选地20-40kg/m3的芯密度。
如本文中使用的刚性泡沫使用聚醚和聚酯多元醇两者制成。对于刚性聚氨酯泡沫(PUR),使用官能度非常高的多元醇(>3),对于聚异氰脲酸酯(PIR)泡沫,为弥补较高的脆性而使用官能度较低的多元醇(<3)。本文中使用的多元醇具有400-800的分子量。如本文中使用的刚性聚氨酯泡沫的特征为:具有2.0磅/立方英尺或更低的芯泡沫密度、95-99%范围内的闭孔含量、在10℃时的6.0-8.0ft2.h.°F/Btu.in的初始耐热性,主要用在隔离体应用中。
一直在汽车、热隔离体和用于很多意图的其它工业中使用刚性泡沫。例如,刚性泡沫一直用于结构增强、防止腐蚀、以及阻尼(衰减)声音和振动。这些泡沫典型地通过将反应性泡沫配制剂施加到零件(部件)并容许所述配制剂原位发泡而形成。该零件在施加所述泡沫时通常已经组装到车辆上。这意味着,所述泡沫配制剂必须易于混合和分配,必须在其从所述零件流掉前快速地固化,并且优选地在适度温度下引发固化。为使工人的化学暴露最少化,所述配制剂在挥发性有机化合物、特别地挥发性异氰酸酯和胺方面优选是低的。所述各组分优选地为在室温下可长期储存稳定的。
应用于泡沫的术语半刚性为本领域中使用的标准术语。通常,这样的泡沫配制成非常轻的密度,而刚性闭孔材料承受负荷但当经历冲击力时容易断裂。
本发明的刚性聚氨酯泡沫的制造方法可包括将所述二醇和/或多元醇组分和/或所述异氰酸酯组分或催化剂和式(IA)、(I-A-1)、(I-A-2)和(I-B)的阻燃剂材料的一种或多种(可计量并泵送到常规混合器皿中)组合,并然后可容易地将所得混合物移动到聚合位点以用在模具、板料操作等中。
也可将所述反应性阻燃剂在与异氰酸酯反应物组合之前与二醇和/或多元醇反应物预混。将反应性阻燃剂材料和异氰酸酯混合、之后将这样的混合物与二醇和/或多元醇反应物组合也在本发明的范围内。然而,如果将异氰酸酯和前述的阻燃剂材料混合并容许其在室温下静置相当长的(substantial)时段,则反应可发生。如在权利要求和本说明书中使用的“反应产物”在一个实施方式中可包括使前述方法的任一种中的刚性聚氨酯泡沫形成用体系的内容物反应,并进一步可包括使反应性阻燃剂经由预聚物技术反应,例如使过量的异氰酸酯与多元醇反应以形成异氰酸酯封端的预聚物、并然后进一步使所述预聚物与本文中所述的反应性阻燃剂和任选的非反应性阻燃剂反应。
本文中所述的式(IA)、(I-A-1)、(I-A-2)和(I-B)的阻燃剂材料可记为异氰酸酯-反应性(NCO-反应性)材料,即它们可通过羟基与异氰酸酯反应。
在制造本文中所述的刚性聚氨酯泡沫中使用的二醇和/或多元醇可包括任何有机多元醇(包括二醇、多元醇),并且可使用具有可与异氰酸酯反应的氢原子的聚醚、聚酯、聚酯酰胺、曼尼希(mannich)基多元醇。通常,这些材料具有范围为约400至约800的分子量并且具有2至约10或更多个羟基/分子和范围为约7.0至约15的重量百分比羟基含量。它们通常具有约350到高至600或甚至700的羟值。
在多元醇类反应物中,酸值应该小于10,通常尽可能地接近于0。所述材料简称为“多元醇”反应物。可用的含活性氢的二醇和/或多元醇包括大家族的加成化合物,其在将环氧乙烷、环氧丙烷、1,2-和2,3-环氧丁烷、或其它环氧烷烃加成(加入)到例如二醇、二元醇和多元醇(示例为乙二醇、丙二醇、甘油、甲基葡糖苷、蔗糖、山梨糖醇、己烷三醇、三羟甲基丙烷、季戊四醇)以及各种烷基胺和亚烷基二胺及多亚烷基多胺等这样的活性氢化合物时产生。取决于聚氨酯的预期用途,可将不同量的这些环氧烷烃加成到所指出的基础二醇、多元醇或胺分子。
例如,在制造刚性泡沫中使用的二醇和/或多元醇也可以甘油为代表,向甘油加入足够的环氧丙烷以得到约8.0%的最终羟基含量。这样的材料将具有约450的分子量。
通过选择二醇和/或多元醇分子和相继加入的环氧烷烃的量控制柔性的所述技术在本领域中为公知的。
除了可作为基础多元醇分子起到加成环氧烷烃并由此产生用于与异氰酸酯反应的“多元醇”分子的作用的甘醇等之外,还可使用包含具有可对环氧烷烃反应的氢的伯和/或仲胺基团的初始分子。此处同样地,环氧烷烃的加入量取决于最终的聚氨酯产品的预期用途。
可作为含活性氢的分子起到与环氧化物反应的作用的代表性胺为具有1至约6或更多个氨基氮的那些,其实例为乙胺、亚乙基二胺(乙二胺)、二亚乙基三胺、三亚乙基四胺、四亚丙基五胺和其它线型饱和的脂族亚烷基胺,重要要求为环氧烷烃可加成到其的至少两个、和优选地更多个、即3至8或10个活性氢位点。
还公知的是,作为在制备聚氨酯体系中使用的活性氢化合物,使用由多官能酸或酸酐和多官能醇通过酯化类型反应制备出的带有羟基的分子。这些化合物通常称为聚酯多元醇。在制造这些聚酯多元醇中使用的典型酸为马来酸、苯二甲酸、琥珀酸、富马酸、四氢苯二甲酸、氯菌酸和四氯苯二甲酸。典型的二醇和/或多元醇为乙二醇、丙二醇、丁二醇、一缩二乙二醇和一缩二丙二醇,以及聚乙二醇、聚丙二醇、和甘油、三羟甲基丙烷、己烷三醇、季戊四醇、山梨糖醇等。在适用的情况下,上述的酸按需可以酸酐的形式使用。
在制造聚酯多元醇中,使各种多官能酸或酸酐或其混合物的任意者与二醇、二元醇或多元醇或者其混合物的任意者在使用按化学计量过量的羟基的情况下反应,使得最终多元醇产物主要包含羟基端基团(末端基团)。通过本领域技术人员所知晓的一种或多种技术容易地改变羟基官能度和百分比羟基的程度以提供期望的多元醇。
在制造刚性聚氨酯的领域和技术中,使用称为预聚物技术的技术也是已知的。它是这样的一种技术:实施在制造刚性聚氨酯中涉及的反应的一部分,产生分子量增大的预聚物,取决于制造该预聚物中使用的化学计量,所得的端基团为羟基或异氰酸酯基。然后,使用该预聚物通过如下而制备最终的刚性聚氨酯产物:使其与异氰酸酯或多元醇反应,这取决于所述预聚物的末端基团是如上所述的羟基还是异氰酸酯基。
宽泛地,可使用现有技术的具有自由反应性氢和特别地羟基的聚酯、异氰酸酯改性的-聚酯预聚物、聚酯酰胺、异氰酸酯改性的聚酯酰胺、亚烷基二醇、异氰酸酯改性的亚烷基二醇、聚氧化亚烷基二醇、异氰酸酯改性的聚氧化亚烷基二醇等的任意者制造本文中所述的聚氨酯。
可使用的异氰酸酯的实例包括迄今为止一直用于制造刚性聚氨酯泡沫的具有两个或更多个异氰酸酯基团的那些。这样的异氰酸酯化合物的实例包括芳族异氰酸酯、脂族异氰酸酯和脂环族异氰酸酯,及这样的异氰酸酯的两种或更多种的混合物,以及通过这样的异氰酸酯的改性获得的改性的异氰酸酯。这样的异氰酸酯的具体实例为甲苯二异氰酸酯、二苯基甲烷二异氰酸酯、多亚甲基多亚苯基多异氰酸酯(粗MDI)、亚二甲苯基二异氰酸酯、异佛尔酮二异氰酸酯和六亚甲基二异氰酸酯;以及这样的异氰酸酯的改性产物,例如碳二亚胺改性产物、缩二脲改性产物、二聚物和三聚物。也可使用由这样的异氰酸酯和含活性氢化合物获得的带有末端异氰酸酯基团的预聚物。
在一个实施方式中,刚性聚氨酯泡沫的异氰酸酯指数范围可为约400至约150、更优选地约375至约175、和最优选地约350至约200。
作为本发明的刚性聚氨酯泡沫形成用组合物中的发泡剂,根据发泡产品所需的性质适宜地选择迄今为止在这样的组合物中使用的已知发泡剂。
在本发明中,视情况需要,还使用交联剂。
作为交联剂,具有至少两个拥有活性氢的官能团例如羟基、伯氨基或仲氨基的化合物是优选的。然而,在其中使用多元醇化合物作为交联剂的情形中,以下内容考虑在内。即,具有至少50mg KOH/g的羟值和多于四个官能团的多元醇化合物被视为所述交联剂,并且不满足此的多元醇被视为上述多元醇混合物中多元醇的任一种(多元醇(1)、(2)或其它多元醇)。此外,两种或更多种交联剂可一起使用。作为具体实例,例如可提到多羟基醇例如葡萄糖、山梨糖醇或蔗糖;具有加成到多羟基醇的环氧烷烃的多元醇;胺化合物例如单乙醇胺、二乙醇胺、亚乙基二胺、3,5-二乙基-2,4(或2,6)-二氨基甲苯(DETDA)、2-氯-对亚苯基二胺(CPA)、3,5-双(甲基巯基)-2,4(或2,6)-二氨基甲苯、1-三氟甲基-4-氯-3,5-二氨基苯、2,4-甲苯二胺、2,6-甲苯二胺、双(3,5-二甲基-4-氨基苯基)甲烷、4,4'-二氨基二苯基甲烷、间亚二甲苯基二胺、1,4-二氨基己烷、1,3-双(氨基甲基)环己烷或异佛尔酮二胺;以及通过将环氧烷烃加成到其而获得的化合物。
当使用以上交联剂时,甚至在例如使用大量发泡剂制造具有低密度的刚性泡沫的情形中,发泡稳定性也将是良好的,并且制造这样的刚性泡沫将是可能的。尤其当使用具有高分子量的二醇和/或多元醇时,制造过去一直被认为难以发泡的具有低密度的刚性泡沫是可能的。此外,当使用交联剂时,相较于不使用其的情形,耐久性将得以改善。在本发明中使用具有高分子量的二醇和/或多元醇的情形中,可容易地改善发泡稳定性,当使用具有相对高的分子量、例如至少4000的分子量的化合物时尤其如此。
水是这样的发泡剂的典型实例;其它实例包括二氯甲烷、正丁烷、异丁烷、正戊烷、异-戊烷、二甲基醚、丙酮、二氧化碳等。取决于发泡的聚氨酯的期望的密度和其它性质,这些和其它发泡剂可单独地或以两种或更多种的组合通过本领域中知晓的方式使用。
发泡剂的用量没有特别限制但通常会在0.1至30重量份/100重量份泡沫形成用组合物的二醇和/或多元醇组分的范围内。优选地,发泡剂的量会是这样的,提供0.8-2.5磅/立方英尺、和优选地0.9-2.0磅/立方英尺的泡沫密度。
本文中的聚氨酯泡沫形成用组合物可优选地包含迄今为止对于聚氨酯泡沫的制造所知晓或使用的催化剂的任一种以及催化剂的组合。可用的催化剂的实例包括氢氧化钠,乙酸钠,叔胺或产生叔胺的材料,例如三甲基胺、三亚乙基二胺、N-甲基吗啉、N,N-二甲基环己基胺和N,N-二甲基氨基乙醇。还适用的是,金属化合物例如烷基羧酸烃锡(hydrocarbon tin alkyl carboxylate)、二乙酸二丁基锡、二辛酸二丁基锡、二月桂酸二丁基锡和辛酸亚锡;以及旨在促进异氰酸酯的三聚的其它化合物,例如2,4,6-三(N,N-二甲基氨基-甲基)苯酚、1,3,5-三(N,N-二甲基-3-氨基丙基)-S-六氢三嗪、辛酸钾、乙酸钾以及催化剂例如和
按需可用很多其它类型的催化剂代替以上列举的那些。催化剂的用量可有利地在0.05-5重量百分比或更大的范围内,基于泡沫形成用混合物中二醇和/或多元醇的总重量。
在制造根据本发明的半刚性泡沫中应用的NCO指数为126-180、和优选地130-175。在制造根据本发明的刚性泡沫中应用的NCO指数为181-350、和优选地200-300。通常理解,聚氨酯泡沫的NCO指数为约80-130,而异脲酸酯泡沫的NCO指数为约200-350。
半刚性泡沫的密度可在8至180、和优选地8-80、和最优选地8-48kg/m3的范围内。
刚性泡沫的密度可在8至180、和优选地8-80、和最优选地8-48kg/m3的范围内。
可加入包括有机表面活性剂和基于有机硅的表面活性剂在内的表面活性剂以起到作为泡孔稳定剂的作用。一些代表性材料以名称SF-1109、L-520、L-521和DC-193(它们通常为聚硅氧烷聚氧基亚烷基嵌段共聚物)销售。还包括包含聚氧化亚乙基-聚氧化亚丁基嵌段共聚物的有机表面活性剂。如下是尤为期望的:使用少量表面活性剂使发泡用反应混合物稳定化直至它固化。在本文中可使用的其它表面活性剂为长链醇的聚乙二醇醚,长链的烯丙基酸式硫酸酯、烷基磺酸酯、烷基芳基磺酸的叔胺或烷醇胺盐,及其组合。这样的表面活性剂以足以使发泡反应稳定化而对抗坍塌和大的不均匀泡孔的形成的量使用。典型地,基于作为整体的所述配制剂约0.2至约3wt%的表面活性剂总量对于该意图是足够的。然而,以较高的量包括某些表面活性剂例如可获自Air Products and Chemicals,Inc.的DABCO DC-5598在一些实施方式中可为期望的。鉴于此,在本发明配制剂中,可以在基于二醇和/或多元醇组分0-6wt.%范围内的任意量包括表面活性剂。
最后,在本文中所述的聚氨酯泡沫形成用配制剂中可包括其它添加剂例如填料和颜料。这些在非限制性实施方式中可包括硫酸钡、碳酸钙、石墨、炭黑、二氧化钛、氧化铁、微球、氧化铝三水合物、硅灰石、精制(prepared)玻璃纤维(断掉的(dropped)或连续的)、聚酯纤维、其它聚合物纤维、其组合等。本领域技术人员会认识到采用本发明配制剂制造刚性聚氨酯泡沫的典型且适宜的手段和方法而不需要进一步的指南,所述刚性聚氨酯泡沫尽管仍然落在所附权利要求的范围内但展现或受益于期望性质和/或加工改造。
刚性泡沫在汽车和其它工业中一直用于很多意图。例如,刚性泡沫一直用于结构增强、防止腐蚀以及阻尼声音和振动。这些泡沫典型地通过将反应性泡沫配制剂施加到零件并容许所述配制剂原位发泡而形成。所述零件当施加所述泡沫时通常已经组装到车辆上。这意味着,所述泡沫配制剂必须易于混合和分配,必须在其从所述零件流掉之前快速地固化,和优选地在适度温度下引发固化。为使工人的化学暴露最少化,所述配制剂在挥发性有机化合物、特别地挥发性异氰酸酯和胺方面优选地是低的。各组分优选地在室温下是长期储存稳定的。
应用到泡沫的术语半刚性为本领域中使用的标准术语。通常,这样的泡沫具有在刚性和柔性泡沫之间的玻璃化转变温度(Tg)。
本文中所述的刚性聚氨酯泡沫可在各种制品例如汽车隔离体、用于墙壁面板和屋顶面板构筑的面板隔离体、以及用于墙壁面板和屋顶面板的现场浇注和喷雾发泡隔离体的构筑和成形中使用。
刚性和半刚性聚氨酯泡沫具有很多应用,例如仿木材和结构性材料。另外,刚性聚氨酯泡沫可在如下应用中使用:例如隔离体、构筑和包装;微孔多泡聚氨酯泡沫,例如鞋类和衬垫;以及粘弹性("记忆")聚氨酯泡沫化学品,在空气过滤器中和作为用于扬声器的装饰性饰面,在层压机上制造的带有适合的饰面或隔汽层(防潮层)的泡沫板,通过压片、成型和喷涂技术施加的罐和管隔离体,用于冷藏机、冷冻机、热水器的隔离体,漂浮和包装中的用途。所述隔离体还可包括窗和门隔离体。
所述隔离体可以任意结构组件例如屋顶或墙壁使用。还提供屋顶结构体,其包括支撑结构面层(主结构板)和隔离面板(例如位于结构面层上的上述那些)的托梁,其中任选地在其上安置盖板,并然后在其上施加防水层例如卷材屋面或沥青等,并然后在其上施加常规的屋顶覆盖物例如木瓦、瓷砖等。
还提供墙壁结构体,其包括与结构支撑部件(例如木、钢或混凝土梁、单层或多个刚性泡沫隔离板(例如聚异氰脲酸酯泡沫板))连接在一起的框架,所述结构支撑部件固定到所述框架外部以形成连续外部墙壁,其中这样的连接和固定通过紧固件例如钉子、螺丝、铆钉等实现,和其中存在在结构支撑部件之间形成的间隔,并且隔离体位于如此形成的间隔内,并任选地将墙壁板紧固到框架内部以形成内表面。
下面的实施例说明本发明的某些化合物的制备和这些化合物在刚性聚氨酯泡沫中作为反应性阻燃剂的效用两者的具体实施方式。
实施例
制备实施例1
向装备有机械搅拌器、油加热器和正位移实验室泵的2-升带夹套的哈斯特洛伊(hastelloy)反应器加入二乙基次膦酸(779g,6.38摩尔)并密封。将所述反应器加热到45℃的内部温度。将环氧丙烷(743g,12.77摩尔)经由所述泵经过两小时加入到所述反应器,同时温度维持在65℃以下。随后,将所述反应器内部温度升高到90℃并在该温度维持三小时。使过量的环氧丙烷蒸发并将残留物使用刮板式薄膜蒸发器在125℃夹套温度下在真空(300-500毫托)下蒸馏。收集作为澄清无色液体的目标级分。相对于初始的二乙基次膦酸的产率为90%。产物为二乙基次膦酸的羟基官能的酯的两种异构体的混合物,31P NMR(乙酸-d4,ppm):66.8–67.7;并且具有0.4mg KOH/g的酸#和15.9%的磷含量。
制备实施例2
向带有加热套、机械搅拌器、回流冷凝器、汲取管、J-CHEM控制器和热电偶、以及碱洗气器的1-升烧瓶加入二乙基次膦酸(469g、3.84摩尔)。将所述烧瓶加热到80℃并将来自加压气瓶的环氧乙烷经过五个小时通过汲取管加入到所述反应器中。环氧乙烷对二乙基次膦酸的最终摩尔比为1.33。将反应混合物在80℃保持另外三小时。进一步将氮气通过所述汲取管以除去过量的环氧乙烷。在150℃和200毫托下完成残留物的间歇式蒸馏,产生澄清液体(400g)。产物为二乙基次膦酸的2-羟乙基酯,31P NMR(CDCl3,ppm):79;并且具有0.4mgKOH/g的酸#。
本发明新化合物的应用通过它们在刚性聚异氰脲酸酯泡沫(应用实施例1)和刚性聚氨酯泡沫(应用实施例2)的标准配制剂中作为阻燃剂的使用而证明。在聚氨酯泡沫的制备中使用以下组分:
应用实施例1
使用新的FR产物制备刚性聚异氰脲酸酯泡沫(PIR,NCO指数250)的方法于下:
通过如下制备泡沫样品:将预先称重的多元醇、水、催化剂、稳定剂、和来自制备实施例1的新的FR产物在烧杯中混合直至形成均匀溶液。然后将戊烷加入到所述溶液中进一步混合。重复该过程直至达到期望的发泡剂重量。在加入和引入MDI之后立即将混合物以2500rpm搅拌6秒并倾倒至8x8x5”(20x20x20 cm)盒中并容许其充分上升。然后将所述盒在通风橱中放置24小时以在室温下固化。然后将样品从所述盒移出、切割成期望尺寸、并对DIN 4201B2以及极限氧指数(LOI)进行测试。
表1总结用于泡沫制备的成分、参数,和测试结果。
表1.聚异氰脲酸酯配方体系
应用实施例2
使用新的FR产物制备刚性聚氨酯泡沫的方法于下:
将预先称重的多元醇、水、催化剂、稳定剂和阻燃剂放置在1000ml一次性聚乙烯(PE)杯子中并混合直至形成均匀溶液。然后将HFC245fa加入到所述溶液中进一步混合。重复该过程直至达到期望的发泡剂重量。在加入MDI之后将混合物立即以2500rpm搅拌3秒,并然后将盛有所有成分的所述杯子放置在通风橱内部的水平台面上并容许其充分上升。在24小时后,然后将样品从所述杯子移出、切割成期望的尺寸、并按照DIN 4201B2和LOI进行测试。
表2总结用于刚性聚氨酯泡沫制备的成分和参数,以及测试结果:
表2.刚性聚氨酯配方体系
尽管参考某些实施方式已经对本发明进行描述,但是本领域技术人员将理解,可做出各种各样的变化并且对其元素可用等同物进行替代而不偏离本发明的范围。另外,为使特定的场景或材料适用于本发明教导,可做出很多改变而不偏离其实质范围。因此,希望本发明不受限于作为用于实施本发明而想到的最佳模式公开的具体实施方式,而是本发明将涵盖落在所附权利要求范围内的所有实施方式。
Claims (22)
1.经阻燃的刚性聚氨酯泡沫,其包括如下物质的反应产物:多元醇、异氰酸酯和阻燃有效量的式(I-A)的单羟基官能的二烷基次膦酸酯化合物:
其中:
R1和R2选自包含1至4个碳原子的线型或支化的烷基;和
k可为0或1;
R3选自氢、包含2至约8个碳原子的单羟基封端的线型或支化的亚烷基;以及,
前提是当k为零时,R3为单羟基封端的线型或支化的亚烷基,且当k为1时,R3为氢,和
2.如权利要求1所述的经阻燃的刚性聚氨酯泡沫,其中R1和R2各自为乙基。
4.如权利要求3所述的经阻燃的刚性聚氨酯泡沫,其中R1和R2各自为乙基。
6.如权利要求5所述的经阻燃的刚性聚氨酯泡沫,其中R1和R2各自为乙基。
7.如权利要求1所述的经阻燃的刚性聚氨酯泡沫,其中所述反应产物为如下物质的反应产物:多元醇、异氰酸酯、阻燃有效量的式(I-A)的单羟基官能的二烷基次膦酸酯化合物以及卤化阻燃剂和/或不同于式(I-A)化合物的另外的磷酯阻燃剂。
8.如权利要求7所述的经阻燃的刚性聚氨酯泡沫,其中所述卤化阻燃剂或另外的磷酯阻燃剂选自三溴新戊醇(FR-513)、三溴苯酚封端的溴化环氧类(F-3014)、溴化的苯二甲酸酯二醇类、磷酸三乙酯、磷酸三(氯异丙基)酯(TCPP)、羟甲基膦酸二乙酯、N,N-双(羟乙基)氨甲基膦酸二乙酯(Fyrol 6)、及其组合。
9.制品,其包括如权利要求1所述的聚氨酯泡沫。
10.应用品,其包括如权利要求9所述的制品,其中所述应用品选自仿木材、隔离体、包装、鞋类、衬垫、粘弹性("记忆")泡沫化学品、用于扬声器的装饰性饰面和空气过滤器、在层压机上制造的泡沫板、饰面或隔汽层、和漂浮应用品。
11.如权利要求10所述的隔离体应用品,其选自汽车隔离体、隔音体、罐和管隔离体、冷藏机隔离体、冷冻机隔离体、热水器隔离体、用于屋顶的面板隔离体、用于墙壁的面板隔离体、天花板隔离体、地板隔离体、以及窗和门隔离体。
12.屋顶结构体或墙壁结构体,其包括如权利要求11所述的用于屋顶的面板隔离体或用于墙壁的面板隔离体。
13.加压的单组分泡沫容器,其包括多元醇、异氰酸酯和阻燃有效量的阻燃剂,所述阻燃剂包括式(I-A)的单羟基官能的二烷基次膦酸酯化合物:
其中:
R1和R2选自包含1至4个碳原子的线型或支化的烷基;和,
k可为0或1;
R3选自氢、包含2至约8个碳原子的单羟基封端的线型或支化的亚烷基;和,
前提是当k为零时,R3为单羟基封端的线型或支化的亚烷基,且当k为1时,R3为氢,以及
15.如权利要求14所述的经阻燃的刚性聚氨酯泡沫,其中R1和R2各自为乙基。
16.如权利要求14所述的经阻燃的刚性聚氨酯泡沫,其中所述反应产物为如下物质的反应产物:多元醇、异氰酸酯、和阻燃有效量的式(I-B)的多醇部分磷酰化的含磷多元醇反应产物、以及卤化阻燃剂和/或不同于由式(I-B)的反应形成的反应产物的另外的磷酯阻燃剂,所述含磷多元醇反应产物包含至少一个含磷基团。
17.如权利要求16所述的经阻燃的刚性聚氨酯泡沫,其中所述卤化阻燃剂或所述另外的磷酯阻燃剂选自三溴新戊醇(FR-513)、三溴苯酚封端的溴化环氧类(F-3014)、溴化的苯二甲酸酯二醇类、磷酸三乙酯、磷酸三(氯异丙基)酯(TCPP)、羟甲基膦酸二乙酯、N,N-双(羟乙基)氨甲基膦酸二乙酯(Fyrol 6)、及其组合。
18.制品,其包括如权利要求14所述的经阻燃的刚性聚氨酯泡沫。
19.应用品,其包括如权利要求18所述的制品,其中所述应用品选自仿木材、隔离体、包装、鞋类、衬垫、粘弹性("记忆")泡沫化学品、用于扬声器的装饰性饰面和空气过滤器、在层压机上制造的泡沫板、饰面或隔汽层、和漂浮应用品。
20.如权利要求19所述的隔离体,其选自汽车隔离体、隔音体、罐和管隔离体、冷藏机隔离体、冷冻机隔离体、热水器隔离体、用于屋顶的面板隔离体、用于墙壁的面板隔离体、天花板隔离体、地板隔离体、以及窗和门隔离体。
21.屋顶结构体或墙壁结构体,其包括如权利要求20所述的用于屋顶的面板隔离体或用于墙壁的面板隔离体。
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CN201880049383.8A Pending CN111194329A (zh) | 2017-07-24 | 2018-07-23 | 包含反应性阻燃剂的刚性聚氨酯泡沫 |
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