CN110945047A - 柔性聚氨酯泡沫用的反应性阻燃剂 - Google Patents
柔性聚氨酯泡沫用的反应性阻燃剂 Download PDFInfo
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- CN110945047A CN110945047A CN201880049392.7A CN201880049392A CN110945047A CN 110945047 A CN110945047 A CN 110945047A CN 201880049392 A CN201880049392 A CN 201880049392A CN 110945047 A CN110945047 A CN 110945047A
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- Prior art keywords
- carbon atoms
- flexible polyurethane
- polyol
- polyurethane foam
- monohydroxy
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- 239000011496 polyurethane foam Substances 0.000 title claims abstract description 47
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- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims abstract description 39
- 229910052698 phosphorus Inorganic materials 0.000 claims abstract description 39
- 239000011574 phosphorus Substances 0.000 claims abstract description 39
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- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 claims description 16
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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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- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
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- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 3
- 229930006000 Sucrose Natural products 0.000 description 3
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- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
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- 239000003381 stabilizer Substances 0.000 description 1
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- UFDHBDMSHIXOKF-UHFFFAOYSA-N tetrahydrophthalic acid Natural products OC(=O)C1=C(C(O)=O)CCCC1 UFDHBDMSHIXOKF-UHFFFAOYSA-N 0.000 description 1
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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
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
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- 239000013638 trimer Substances 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
- ASLWPAWFJZFCKF-UHFFFAOYSA-N tris(1,3-dichloropropan-2-yl) phosphate Chemical compound ClCC(CCl)OP(=O)(OC(CCl)CCl)OC(CCl)CCl ASLWPAWFJZFCKF-UHFFFAOYSA-N 0.000 description 1
- 239000010456 wollastonite Substances 0.000 description 1
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- 239000011592 zinc chloride Substances 0.000 description 1
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 1
Classifications
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- 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'
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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
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- 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
- B65D83/38—Details of the container body
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/30—Phosphinic acids [R2P(=O)(OH)]; Thiophosphinic acids ; [R2P(=X1)(X2H) (X1, X2 are each independently O, S or Se)]
- C07F9/32—Esters thereof
- C07F9/3205—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/3211—Esters of acyclic saturated acids which can have further substituents on alkyl
-
- 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
- C08G18/08—Processes
- C08G18/14—Manufacture of cellular products
-
- 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
- C08G18/08—Processes
- C08G18/16—Catalysts
- C08G18/161—Catalysts containing two or more components to be covered by at least two of the groups C08G18/166, C08G18/18 or C08G18/22
- C08G18/163—Catalysts containing two or more components to be covered by at least two of the groups C08G18/166, C08G18/18 or C08G18/22 covered by C08G18/18 and C08G18/22
- C08G18/165—Catalysts containing two or more components to be covered by at least two of the groups C08G18/166, C08G18/18 or C08G18/22 covered by C08G18/18 and C08G18/22 covered by C08G18/18 and C08G18/24
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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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- C08G18/08—Processes
- C08G18/16—Catalysts
- C08G18/18—Catalysts containing secondary or tertiary amines or salts thereof
-
- 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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- C08G18/24—Catalysts containing metal compounds of tin
- C08G18/244—Catalysts containing metal compounds of tin tin salts of carboxylic acids
-
- 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
- C08G18/288—Compounds containing at least one heteroatom other than oxygen or nitrogen
-
- 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
- C08G18/40—High-molecular-weight compounds
- C08G18/4009—Two or more macromolecular compounds not provided for in one single group of groups C08G18/42 - C08G18/64
- C08G18/4018—Mixtures of compounds of group C08G18/42 with compounds of group C08G18/48
-
- 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
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Abstract
本发明提供在柔性聚氨酯泡沫中充当非常高效的反应性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。本发明进一步提供包括所述单羟基官能的二烷基次膦酸酯与多元醇和异氰酸酯泡沫形成组分的反应产物的防火聚氨酯组合物。
Description
相关申请的交叉引用
本申请要求2017年7月24日提交的、序列号为62/536,260的美国临时专利申请的权益,该申请在此并入作为参考。
技术领域
本公开在此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用途,其在与多元醇和异氰酸酯反应时,在柔性聚氨酯泡沫(泡沫体,foam)中充当高效的反应性阻燃剂。本发明进一步提供防火的柔性聚氨酯泡沫,其中所述羟基官能的二烷基次膦酸酯反应并引入到柔性聚氨酯泡沫的聚合物基体中。措辞“防火剂”和“阻燃剂”在本文中可互换地使用。
背景技术
已知的是,溴化的或基于磷的阻燃剂是高度有效的并且在很多情形中是用于降低合成材料例如柔性聚氨酯泡沫的起火(火灾)风险的唯一选项。然而,提升的公众和政府对化学品(和特别是阻燃剂)的监督力度在近些年来一直在增强。目的是朝向更加可持续的、反应性的、聚合物的和/或不含卤素的新产品。如果阻燃剂反应到聚合物基体中并且无法浸出,则监督力度将大大减弱。
因此,对于这样的用于柔性聚氨酯的反应性的含磷防火剂存在需求:其拥有特征诸如高的磷含量、透明的浅色以及与在聚氨酯工业中使用的聚醚多元醇和聚酯多元醇的良好的相容性。
发明内容
本发明提供反应性二烷基含磷单羟基官能的化合物,其拥有非常令人满意的阻燃特性且具有与柔性聚氨酯泡沫形成体系的多元醇组分的良好的相容性。如本文中使用的表述“柔性聚氨酯泡沫形成体系”将理解为包括多元醇、异氰酸酯和如本文中描述的反应性二烷基含磷单羟基官能的化合物。所述单羟基官能的二烷基次膦酸酯化合物通过它们的单个羟基官能团而具有充分的反应性,并且与二-或三-羟基官能的二烷基次膦酸酯化合物相比更容易配制(formulate)。令人惊讶地发现,尽管本文的反应性单羟基官能的二烷基次膦酸酯化合物的羟基官能团的含量较低,但其可以例如通过与柔性聚氨酯泡沫形成体系的异氰酸酯组分的反应而进行反应并引入到柔性聚氨酯泡沫的聚合物结构中,而不破坏柔性聚氨酯泡沫的弹性性质。这意味着,本发明的阻燃剂变成一体化(整合)到柔性泡沫基体中,使得它们不释放到环境中并且不太可能渗透通过活组织的细胞膜,并且因此不造成健康危害。本发明进一步提供上述柔性聚氨酯泡沫形成体系,包括但不限于本文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“泡沫”指的是柔性聚氨酯泡沫。本文中描述为或本文中主张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(通式(I-B)代表多醇(多元醇,polyalcohol)经部分磷酰化(磷酸化,phosphorylation)的包含至少一个含磷基团的含磷二元醇和/或多元醇反应产物的组)、基本由其组成、或由其组成的柔性聚氨酯泡沫在本文中均理解为包含前述式作为反应性材料,即前述式反应到柔性聚氨酯材料的结构中,在该情形中前述式可不以或将不以如本文中所描述的相同结构式存在,而是将作为二元醇和/或多元醇、异氰酸酯和本文中描述的结构式的反应产物存在于柔性聚氨酯材料中。
本文使用的术语“多元醇”将理解为还可能定义为二元醇和/或多元醇。
本发明提供通式(I-A)和(I-B)的单羟基官能的二烷基次膦酸酯化合物、以及通式(I-B)的包含至少一个含磷基团的多醇的部分磷酰化的含磷二元醇和/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1-4个碳原子的直链或支化的烷基,例如甲基、乙基、丙基、异丙基、丁基和异丁基,优选甲基或乙基,更优选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2-4个碳原子的单羟基封端的直链或支化的亚烷基;和
条件是当k为0时,R3为所述单羟基封端的直链或支化的亚烷基且当k为1时,R3为氢,并且
当X为时,R4和R5各自独立地选自H,包含1-8个碳原子、优选1至约4个碳原子的直链或支化的烷基,且最优选甲基、乙基或丙基的任一者,包含2-8个碳原子、优选2至约4个碳原子的直链或支化的烯基,包含1-8个碳原子的卤素取代的烷基,包含1-8个碳原子、优选1至约4个碳原子的烷氧基,包含6-12个碳原子、优选6至约8个碳原子的芳基,和包含7-16个碳原子、优选7至约12个碳原子的烷芳基,或R4和R5彼此成键而形成包含4至约8个碳原子、优选6个碳原子的环烷基;以及其中式(I-B)为:
其中:
R1和R2独立地选自包含1-4个碳原子的直链或支化的烷基,例如甲基、乙基、丙基、异丙基、丁基和异丁基,优选甲基或乙基,更优选R1和R2两者均为乙基;和
n1为等于或大于1的整数,且n2为1,优选n1为1至约5,和
Z2为源自二元醇或多元醇的具有化合价n1+n2的部分,并且为以下通式:
其中R选自:
以及其中各R6独立地为H或1-4个碳原子的烷基,x为0或≥1,优选1-4,更优选x=1,y为2或3;z为2-5的整数;和m≥1,优选m=1。
本文还提供制备这些化合物的工艺。
新的式(I-A)化合物可通过式(II)的单羟基官能的二烷基次膦酸和具有氧杂环丙烷基团的化合物反应而制备,其中式(II)为:
其中R1和R2如定义的。
式(I-A)化合物也可以通过式(III)的二烷基次膦酰卤和脂族二元醇反应而制备,其中式(III)为:
以及其中R1和R2如定义的,且A为氯或溴。
本发明的含磷二元醇和/或多元醇例如式I-B的那些可通过式(III)的二烷基次膦酰卤和脂族二元醇和/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的稳定性、呈现良好的与柔性聚氨酯泡沫形成体系的二元醇和/或多元醇组分的相容性、并且在柔性聚氨酯泡沫中可作为高效的反应性阻燃剂使用。
本发明进一步提供防火柔性聚氨酯,其包括所述含磷单羟基官能的化合物在柔性聚氨酯泡沫形成体系中反应而形成柔性聚氨酯泡沫之后的反应性残余物(残基)。本文的含磷单羟基官能的化合物可在柔性聚氨酯泡沫形成体系中单独地或者以与彼此之间和/或与其它阻燃剂(包括含卤素阻燃剂和含磷阻燃剂)的混合物使用。
本发明所有的以上和其它特征和优势通过下面的对其优选实施方式的说明性和非限制性的详细描述将被更好地理解。
具体实施方式
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以为更具体的式(I-A-1)或(I-A-2)的那些,其中式(I-A-1)为:
其中R1和R2、Z、k及R3如上面定义的;和
其中式(I-A-2)为:
以及其中R1、R2、R4和R5如上面定义的。
在本文的一个实施方式中,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)的二烷基次膦酸和具有氧杂环丙烷基团的式(IV)的化合物反应而制备,其中式(IV)为:
式(IV)
其中:
R4和R5如上面定义的。
在本文的一个另外的实施方式中,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)的二烷基次膦酰卤和式(V)的脂族二元醇反应而制备:
HO-(Z)K-R3 (V)
其中Z、R3和下标k为如上所限定的。
本发明的含磷二元醇和/或多元醇例如式I-B的那些通过式(III)的二烷基次膦酰卤和脂族二元醇或多元醇的反应制备。
在本发明的工艺中作为起始材料使用的二烷基次膦酸(II)和二烷基次膦酰卤(III)多半是本领域中所熟知的。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(其内容通过引用并入本文中)中描述的方法制备。
在用于制备本发明的式(I-A)或更具体地(I-A-1)或(I-A-2)的化合物的工艺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)或更具体地(I-A-1)或(I-A-2)的化合物的工艺中使用的具体的脂族二元醇选自但不限于,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-丙二醇、1,4-丁二醇、2-丁烯-1,4-二醇、1,5-戊二醇、1,6-己二醇、1,8-辛二醇和具有最高至700的分子量的其它二元醇。
用于制备本发明的含磷多元醇的工艺中使用的脂族二元醇和/或多元醇可分别通常为具有至少两个或至少三个反应性氢原子的任何合适的二元醇和/或多元醇,实例为具有2或3-6、优选地2、3和4的官能度和优选地约100到约700的分子量的那些。具体的脂族二元醇和/或多元醇可选自非聚合物多元醇,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元醇和/或多元醇为聚醚二元醇和/或多元醇。这类二元醇和/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)和合适的含一个或多个活性氢原子的反应物(例如醇、胺和酸)的开环加成反应获得;更具体地,所述反应物可选自二元醇、三元醇、酚醛清漆树脂、季戊四醇、山梨糖醇、蔗糖、二亚乙基三胺等。根据本发明还可使用聚酯多元醇;这类多元醇通过羧酸、二羧酸(或多羧酸)例如己二酸、苯二甲酸等和二元醇或三元醇的缩合反应获得。用于制备本发明的含磷一元醇、二元醇或多元醇的工艺中使用的脂族二元醇和/或多元醇选自聚合物二元醇和/或多元醇,例如聚醚多元醇、聚酯多元醇和它们的混合物。
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相对于单羟基二烷基次膦酸(II)为5-300%摩尔过量的、和优选为50-100%摩尔过量的。使用相对于单羟基二烷基次膦酸(II)大于100%摩尔过量的氧杂环丙烷化合物由于需要回收大量的氧杂环丙烷而是不合意的。
取决于对于所述反应所消耗的二烷基次膦酸和氧杂环丙烷,本发明的式(I-A)或者更具体地(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作为目标的单羟基官能的二烷基次膦酸酯(I-A)或更具体地(I-A-1)或(I-A-2)的制备而言,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进行反应是优选的。
因此,式(I-A)或更具体地(I-A-1)或(I-A-2)中具有特别有价值的性质的化合物为如下那些:其中R1、和R2各自为乙基。
所述反应在介于40℃和120℃之间、和优选地介于70℃和90℃之间的温度下进行。在低于40℃的温度下,所述反应变为不可接受地慢。另一方面,施加高于120℃的温度是不可取的,因为在这样的温度下可形成不期望的分解产物。
在一种优选的实施方式中,二烷基次膦酰卤(III)和脂族二元醇的反应在过量二元醇的介质中进行。
在与二烷基次膦酰卤(III)的反应中使用的二元醇化合物的量通常为每1摩尔二烷基次膦酰卤2-10摩尔、和优选地4-8摩尔的摩尔过量。为了使不期望的不具有羟基的二醇类(glycols)和二元醇的双(二烷基次膦酸)酯的形成最小化,需要这些二元醇的相对大的过量。使用每1摩尔二烷基次膦酰卤的大于10摩尔的摩尔过量的二元醇化合物由于需要回收大量的二元醇而是不合意的。
取决于对于所述反应所消耗的二烷基次膦酰卤和二元醇,本发明的式(I-A)或者更具体地(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。
为了制备具有尽可能高的磷含量的作为目标的单羟基官能的二烷基次膦酸酯(I-A)、或者更具体地(I-A-1)或(I-A-2),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和乙二醇进行反应是优选的。
因此,式(I-A-1)的具有特别有价值的性质的化合物为如下的:其中R1和R2各自为乙基,k为1,n为1,Y为–CH2CH2–,且R3为氢。
所述反应在介于25℃和120℃之间、和优选地介于50℃和90℃之间的温度下进行。施加低于25℃的温度导致低产率。另一方面,施加高于120℃的温度是不可取的,因为在这样的温度下可形成不期望的分解产物。另外,为了加快反应,可使用催化剂例如MgCl2或ZnCl2。
在一种优选的实施方式中,二烷基次膦酰卤(III)和脂族二元醇的反应在强碱例如氢氧化钠或氢氧化钾的存在下在有机溶剂和过量的脂族醇两者的介质中进行。所述有机溶剂选自芳族化合物。特别合适的芳族溶剂为氯苯、邻-二氯苯、莱以及特别地甲苯和二甲苯。在所述工艺中采用的碱的有效量在每1mol二烷基次膦酰卤(III)的1-1.2mol、和优选地1-1.05mol的范围内。
可以固体形式采用钠或钾的氢氧化物。应该在加入二烷基次膦酰卤(III)之前将由所述二元醇和所述碱之间的反应产生的水尽可能多地从反应混合物除去。
在一种优选的实施方式中,二烷基次膦酰卤(III)和脂族二元醇和/或多元醇的反应通过改变所述二元醇和/或多元醇的部分磷酰化的程度而进行。根据本发明的含磷二元醇和/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如定义的,和其中波浪线表示经由氧原子至二元醇或多元醇的键。
本发明的含磷二元醇和/或多元醇还可包含两个或更多个式(III-A)的含磷基团,其中这些含磷基团可为相同的或不同的。
二烷基次膦酰卤(III)和脂族二元醇和/或多元醇的反应可在有机碱的存在下进行,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。所使用的碱的量与二烷基次膦酰卤(III)是等摩尔的。还可以相对于二烷基次膦酰卤过量地使用所述碱。所述反应典型地在惰性有机溶剂的介质中进行。对于所述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。另外适合的溶剂为醚例如二烷或四氢呋喃。另外适合的溶剂为烃例如己烷或甲苯。
在一种优选的实施方式中,二烷基次膦酰卤(III)和脂族二元醇和/或多元醇的反应在强的无机碱例如氢氧化钠或氢氧化钾的存在下在有机溶剂例如氯苯、莱、以及特别地甲苯和二甲苯的介质中进行。
在所述工艺中采用的碱的有效量在每1mol二烷基次膦酰卤(III)的1-1.2mol、和优选地1-1.05mol的范围内。可以固体形式使用钠或钾的氢氧化物。应该在加入二烷基次膦酰卤(III)之前将由所述二元醇和/或多元醇和所述碱之间的反应产生的水尽可能多地从反应混合物除去。
可调节二烷基次膦酰卤(III)和二元醇和/或多元醇的量使得达到期望的官能化程度。所述二元醇和/或多元醇的部分磷酰化可通过使用二烷基次膦酰卤(III)对二元醇和/或多元醇基于其官能度的小于化学计量的量而实现。以这种方式,二元醇和/或多元醇中OH基团的仅一部分与二烷基次膦酰卤反应。
本发明的含磷二元醇和/或多元醇(在本文也描述为部分磷酰化的二元醇和/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。取决于对于所述反应所消耗的二烷基次膦酰卤和二元醇和/或多元醇以及它们之间的摩尔比,本发明的含磷二元醇和/或多元醇具有约4-20重量%的磷含量和约20-800mg KOH/g的羟值。
二元醇和/或多元醇的磷酰化反应在介于0℃和100℃之间、和优选地介于10℃和90℃之间的温度下进行。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℃的温度是不可取的,因为在这样的温度下可形成不期望的分解产物。
以下实例说明本发明的某些化合物的制备和这些化合物在柔性聚氨酯泡沫中作为阻燃剂的用途两者的具体实施方式。
本发明的化合物可作为反应性阻燃剂使用。所述阻燃剂可按原样(按制备时,as-is)或者作为与卤化或非卤化的产物的混合物使用。对于柔性聚氨酯泡沫,优选的是,本发明的不含卤素的羟基官能的二烷基次膦酸酯以纯的形式使用或者与其他不含卤素的产品一起使用。
本发明的化合物当引入到柔性聚氨酯泡沫中时是高效的反应性阻燃剂。应该指出,本发明的化合物可在宽的异氰酸酯指数(其在本文中缩写为MDI或TDI)内使用。所述指数指的是配制剂中实际使用的异氰酸酯相对于所需的异氰酸酯的理论化学计量量的以百分数计的比率。
本文的柔性聚氨酯泡沫包含典型的阻燃剂有效量的本发明组合物。典型地,本发明组合物以提供基于聚合物(即,所述柔性聚氨酯泡沫)的总重量的在0.3-15重量%范围内的聚合物中的总磷浓度的量施加。优选地,聚合物中的总磷浓度在1-10重量%的范围内、和更优选地在1.5-5重量%的范围内,基于柔性聚氨酯聚合物的总重量。最优选地,本发明的反应性阻燃剂的使用量至少足以满足可燃性测试方法MVSS 302的现行要求。
通过适当地选择组分和条件,制造在关于柔性程度的性质方面可变化的柔性聚氨酯泡沫。因此,柔性泡沫通常使用水作为主起泡剂(发泡剂)由具有20-80的羟值的聚合物二元醇或三元醇制成。
本发明的柔性聚氨酯泡沫可包含适当选择的助剂,例如催化剂、表面活性剂、泡沫稳定剂等。
如本文中使用的柔性聚氨酯泡沫使用具有3,000-约6,000分子量的二元醇和/或多元醇(如本文中所描述的二元醇和/或多元醇)例如通过将环氧丙烷加成到甘油制备的聚醚三元醇制成。如本文中使用的柔性聚氨酯泡沫的特征在于,其具有至多30%的芯冲击回弹性和-80℃到-60℃的玻璃化转变点。这里,柔性聚氨酯泡沫优选地具有至多40质量%的硬链段含量。常规的柔性聚氨酯泡沫具有2.5磅/立方英尺(PCF)或更低的泡沫堆密度(体密度)且具有10-90lb/50in2范围内的泡沫硬度或IFD(其按照测试方法ASTM 3574-Test B1测量)。
制备本发明的柔性氨酯泡沫的方法可以包括将二元醇和/或多元醇组分和/或异氰酸酯组分或催化剂以及本文中描述的式(I-A)、(I-A-1)、(I-A-2)和(I-B)的阻燃剂材料的一种或多种组合,其可计量且泵送到共同的混合容器中,且然后所得混合物可容易地移动到聚合位点以在模具、板料操作等中使用。
本文的本发明的反应性阻燃剂还可在与异氰酸酯反应物组合之前与二元醇和/或多元醇反应物进行预混合。在将该反应性阻燃剂材料和异氰酸酯混合之后将这样的混合物和二元醇和/或多元醇反应物组合也在本发明范围内。然而,如果将异氰酸酯和前述的阻燃剂材料混合并且使其在室温下静置相当长的(substantial)时期,则反应可发生。如在本文的权利要求书和说明书中使用的“反应产物”在一个实施方式中可以包括使在任一前述方法中的柔性氨酯泡沫形成体系的内容物反应,并且可以进一步包括使所述反应性阻燃剂经由预聚合物技术反应,诸如例如,使过量的异氰酸酯和多元醇反应形成异氰酸酯封端的预聚物并且然后使该预聚物进一步与本文的反应性阻燃剂反应。
本文中描述的式(I-A)、(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进行反应。
在制造本文中描述的柔性聚氨酯泡沫中使用的二元醇和/或多元醇可包括任何有机多元醇(包括二元醇、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、聚酯酰胺多元醇。通常,这些材料具有约62-约5,000范围内的分子量且具有每分子2-约10或更多个羟基和约0.5-约25%范围内的重量百分比的羟基含量。它们通常具有约50到最高500或甚至700的羟值。
在聚酯多元醇类型的反应物中,酸值应该小于10,通常尽可能地接近于0。这些材料被简单地称为“多元醇”反应物。可用的含活性氢的二元醇和/或多元醇包括当将环氧乙烷、环氧丙烷、1,2-和2,3-环氧丁烷、或其它环氧烷烃加成到这样的活性氢化合物例如二元醇、二醇类和多元醇(其以乙二醇、丙二醇、甘油、甲基葡糖苷、蔗糖、山梨糖醇、己三醇、三羟甲基丙烷、季戊四醇为代表)以及多种烷基胺和亚烷基二胺、和多亚烷基多胺等时得到的一大族加合物化合物。取决于聚氨酯的预期意图,可将不同量的这些环氧烷烃加成到所提及的基础二元醇、多元醇或胺分子。
例如,制造柔性泡沫中使用的二元醇和/或多元醇可恰好以如下甘油为代表:将足够的环氧丙烷加成到该甘油以得到约1.7%的最终羟基含量。这样的材料将具有约3,000的分子量且具有约1甘油对50环氧丙烷的甘油对环氧丙烷摩尔比。
通过选择二元醇和/或多元醇分子和随后加成的环氧烷烃的量来控制柔性的这一技术对于本领域技术人员是熟知的。
除了可充当用于环氧烷烃的加成的基础多元醇分子且由此产生用于与异氰酸酯反应的“多元醇”分子的二醇类等之外,还可使用包含具有对环氧烷烃有反应性的氢的伯和/或仲胺基团的起始分子。这里同样地,加成的环氧烷烃的数量取决于最终聚氨酯产品的预期用途。在本文的柔性聚氨酯产品中,将使用环氧烷烃以产生具有较低羟基含量例如约0.1%到约5%或10%的多元醇。
可充当含活性氢的分子与环氧化物进行反应的代表性的胺为具有1到约6或更多个氨基氮的那些,其实例为乙基胺、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脂族亚烷基胺,重要的要求(前提)是有至少两个、和优选地更多个(比如说3-8或10个)环氧烷烃可加成至其的活性氢位点。
使用由多官能酸或酸酐和多官能醇通过酯化类型反应而制备的带有羟基的分子作为在制备聚氨酯体系中使用的活性氢化合物也是熟知的。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。典型的二元醇和/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、聚乙二醇、聚丙二醇、甘油、三羟甲基丙烷、己三醇、季戊四醇、山梨糖醇等。在可得到的情况下,如果期望可以酸酐的形式使用上述酸。
在制造聚酯多元醇中,使多种多官能的酸或酸酐或其混合物的任意种和二元醇、二醇类或多元醇或其混合物的任意种在使用化学计量过量的羟基的情况下进行反应,使得最终的多元醇产物主要包含羟基末端基团。通过本领域技术人员已知的技术和技能容易地改变羟基官能团的程度和百分比羟基以提供期望的多元醇。
在制造柔性聚氨酯的领域和技术中,使用所谓的预聚物技术也是已知的。其是这样的技术:其中进行在制造柔性聚氨酯中涉及的反应的一部分,产生分子量增加的预聚物,且取决于在制造该预聚物中使用的化学计量,所得末端基团为羟基或异氰酸酯。然后,使用该预聚物通过使其与异氰酸酯或多元醇(这取决于所述预聚物的端基是如上提到的羟基还是异氰酸酯)进行反应而制备最终的柔性聚氨酯产品。
概括地说,可采用现有技术的具有自由的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来制造本文中描述的聚氨酯。
可使用的异氰酸酯的实例包括迄今一直用于制造柔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、以及这样的异氰酸酯的两种或更多种的混合物、和通过将这样的异氰酸酯改性获得的改性异氰酸酯。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、聚亚甲基聚亚苯基多(聚)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-改性的产物、缩二脲-改性的产物、二聚物和三聚物。还可使用由这样的异氰酸酯和含活性氢的化合物获得的具有末端异氰酸酯基团的预聚物。
在一个实施方式中,柔性聚氨酯泡沫的异氰酸酯指数范围可为约130-约80、更优选地约120-约90、和最优选地约115-约95。
作为本发明的柔性聚氨酯泡沫形成组合物中的发泡剂,根据发泡产品所需的性质适当地选择在这样的组合物中迄今使用的已知发泡剂。
在本发明中,视情况需要还使用交联剂。
作为所述交联剂,拥有至少两个具有活性氢的官能团(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所述交联剂的情形中,考虑到以下。即,具有至少50mg KOH/g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,且不满足此的多元醇被视为上述多元醇混合物的多元醇(多元醇(1)、(2)或其它多元醇)的任一种。此外,两种或更多种交联剂可一起使用。作为具体的实例,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(甲硫基)-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,甚至在其中使用例如大量发泡剂制造具有低密度的柔性泡沫的情形中,发泡稳定性将是良好的,并且制造这样的柔性泡沫将是可能的。特别地当使用具有高分子量的二元醇和/或多元醇时,制造过去常常被认为难以发泡的具有低密度的柔性泡沫是可能的。此外,当使用所述交联剂时,与其中不使用其的情形相比,持久性将改善。在其中如在本发明中使用具有高分子量的二元醇和/或多元醇的情形中,可容易地改善发泡稳定性,当使用具有相对高分子量、例如至少4000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、二甲醚、丙酮、二氧化碳等。取决于发泡聚氨酯的期望密度和其它性质,这些和其它发泡剂可以本领域中已知的方式单独地或者以两种或更多种的组合使用。
所使用发泡剂的量没有特别限制但是通常将在0.1-20重量份的范围内,相对于100重量份的泡沫形成组合物的二元醇和/或多元醇组分。优选地,发泡剂的量将是这样的,其提供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组合物可优选地包含迄今已知或用于制造聚氨酯泡沫的催化剂的任一种和所述催化剂的组合。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。还可应用的是,金属化合物,例如烃烷基羧酸锡(hydrocarbon tin alkylcarboxylate)、二丁基二乙酸锡、二丁基二辛酸锡、二丁基二月桂酸锡和辛酸亚锡;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,和催化剂例如DABCO和POLYCAT
如果期望,可用很多其它类型的催化剂代替以上列出的那些。使用的催化剂的量可有利地在0.05-5重量百分比或更大的范围内,基于泡沫形成混合物中二元醇和/或多元醇的总重量。
在制造根据本发明的柔性泡沫中应用的异氰酸酯(NCO)指数为95-125且优选为100-120。通常理解的是聚氨酯泡沫的NCO指数为约80-130。
本文的柔性聚氨酯泡沫的密度可在14-80、优选16-55、且最优选20-40kg/m3的范围内。
可加入表面活性剂(其包括有机表面活性剂和基于有机硅的表面活性剂)以充当泡孔(cell)稳定剂。一些代表性的材料以名称SF-1109、L-520、L-521和DC-193销售,它们通常为聚硅氧烷聚氧化亚烷基嵌段共聚物。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。使用少量的表面活性剂使发泡反应混合物稳定化直至其固化是特别期望的。本文中可用的其它表面活性剂为长链醇的聚乙二醇醚、长链烯丙基酸硫酸酯的叔胺或烷醇胺盐、烷基磺酸酯、烷基芳基磺酸、及其组合。这样的表面活性剂以足以使发泡反应稳定化而抵抗坍塌和大的不均匀泡孔的形成的量使用。典型地,基于总体配制剂的约0.2-约3重量%的表面活性剂的总量对于该意图是足够的。然而,以更高的量包括一些表面活性剂例如DABCO DC-5598(其可获自Air Products and Chemicals,Inc.)在一些实施方式可能是期望的。鉴于此,在本发明配制剂中可以基于二元醇和/或多元醇组分的0-6重量%范围内的任意量包括表面活性剂。
最后,在本文中描述的聚氨酯泡沫形成配制剂中可包括其它添加剂例如填料和颜料。其在非限制的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、制备的玻璃纤维(滴落的(断掉的,dropped)或连续的)、聚酯纤维、其它聚合物纤维、其组合等。本领域技术人员将认识到使本发明配制剂适于制造柔性聚氨酯泡沫的典型且合适的手段和方法而无需另外的指导,这仍然落在所附权利要求的范围内,但是呈现或受益于期望的性质和/或加工改造。
本文中描述的柔性聚氨酯泡沫,它们可用于构造和形成多种制品,例如家具、寝具、和汽车座垫,更具体地用于家具应用、汽车应用、船只应用、公共汽车座椅应用、列车座椅应用、RV座椅应用、办公家具座椅应用、航空应用、牵引车应用、自行车应用、发动机架应用、压缩机应用、寝具应用、隔离应用、体育用品应用、鞋应用、地毯衬垫应用、包装应用、织物应用、缓冲减震应用、HVAC应用、帐篷应用、救生筏应用、行李应用和手袋应用。
柔性板料聚氨酯泡沫可用于家具例如装有垫子的家具(upholstered furniture)例如衬垫、靠背和扶臂(backs and arms),汽车工业例如汽车和卡车用的座椅和背垫、及顶衬和头枕,用于公共交通(例如公共汽车和飞机)座椅以及用在牵引车、自行车和摩托车的座椅的任意者中,以及安全轮胎的支承环,和其他汽车内部构件;寝具例如床垫,作为隔音材料,汽车内部构件例如扶手、方向盘和变速杆捏手,鞋底,和运动用品。
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泵的2升带夹套的哈斯特洛伊(哈氏合金,hastelloy)反应器中装入二乙基次膦酸(779g,6.38mol)并密封。将所述反应器加热至45℃的内部温度。将环氧丙烷(743g,12.77mol)在两个小时经由泵加入所述反应器中并使温度保持低于65℃。随后将反应器的内部温度上升至90℃并在此保持3小时。使过量的环氧丙烷蒸发,并将残留物使用刮膜蒸发器在125℃夹套温度下在真空(300-500毫托)下蒸馏。收集目标级分,为澄清无色液体。相对于起始的二乙基次膦酸,产率为90%。所述产物为羟基官能的二乙基次膦酸酯的两种异构体的混合物,31P NMR(乙酸-d4,ppm):66.8–67.7;并具有0.4mg KOH/g的酸值及15.9%的磷含量。
制备实施例2
向装备有加热套、机械搅拌器、回流冷凝器、汲取管(dip tube)、J-CHEM控制器和热电偶,以及碱洗器的1升烧瓶中装入二乙基次膦酸(469g,3.84mol)。将烧瓶加热至80℃并将来自加压罐的环氧乙烷在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。将反应混合物保持在80℃另外三小时。进一步使氮气通过汲取管以除去过量环氧乙烷。在150℃和200毫托下完成残留物的间歇蒸馏,得到澄清液体(400g)。产物为二乙基次膦酸的2-羟基乙基酯,31P NMR(CDCl3,ppm):79;并且具有0.4mgKOH/g的酸值。
本发明的新化合物的应用通过其在柔性聚氨酯泡沫的标准配制剂中用作阻燃剂(应用实施例3)得到证实。
除了新的阻燃剂化合物外,在聚氨酯泡沫的制备中还使用以下组分:
材料 | 制造商 |
Voranol 8136聚醚多元醇 | Dow |
Desmophen 60WB01聚酯多元醇 | Covestro |
Niax A-1胺催化剂 | Momentive |
Niax C-131NPF | Momentive |
Niax DMP | Momentive |
Niax L-537XF | Momentive |
Niax L-620 | Momentive |
Dabco 33LV胺催化剂 | Air Products |
T-9辛酸亚锡催化剂 | Air products |
TDI 80 | Everchem Specialty Chemicals |
TDI 65 | Everchem Specialty Chemicals |
新的FR产品(来自实施例1) | ICL |
Fyrol FR-2,Fyrol A300-TB | ICL |
应用实施例3
通过将多元醇和来自制备实施例1的新的FR产品混合来制备泡沫样品。将包括水、胺催化剂、有机硅表面活性剂和锡催化剂(除了异氰酸酯之外)的配制剂的余下组分加入到多元醇/FR产品混合物并以如下条件搅拌到其中:对于聚醚泡沫在2000rpm下搅拌30秒,对于聚酯泡沫在1000rpm下搅拌60秒。在剧烈搅拌下将异氰酸酯添加和引入到反应混合物中,之后马上将全部反应混合物随即倒入8x8x5”(20x20x20 cm)的箱子中并容许其充分上升。对于聚醚泡沫,将箱子然后放在通风橱中24小时,从而在室温下固化;对于聚酯泡沫,首先将箱子放在110℃烘箱中并固化10分钟,接着在室温固化24小时。除去泡沫样品顶部和底部的0.5”,以及泡沫的纸衬侧面。然后切割样品并测试易燃性,包括联邦机动车辆安全标准No.302(Federal Motor Vehicle Safety Standard No.302,FMVSS 302),根据VDA 277的排放测试。
表1和2呈现泡沫制剂的成分、参数和测试的结果
表1.聚醚柔性泡沫配制剂体系和测试结果
SE=自熄灭性试样,被点燃但在进入时区之前自熄灭
表2.聚酯柔性泡沫配制剂体系和测试结果
尽管参考某些实施方式对本发明已经进行描述,但是本领域技术人员将理解,可作出各种各样的改变并且对于其要素可用等同物替代而不偏离本发明的范围。另外,为了使特定的场景或材料适用于本发明的教导可作出很多变更而不偏离其实质范围。因此,其意指本发明不受限于作为用于实施本发明而联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的范围内的所有实施方式。
Claims (20)
1.经阻燃的柔性聚氨酯泡沫,其包括多元醇、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的反应产物:
其中:
R1和R2选自包含1-4个碳原子的直链或支化的烷基;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直链或支化的亚烷基;和
条件是当k为0时,R3为所述单羟基封端的直链或支化的亚烷基,且当k为1时,R3为氢,和
2.权利要求1的经阻燃的柔性聚氨酯泡沫,其中R1和R2各自为乙基。
4.权利要求3的经阻燃的柔性聚氨酯泡沫,其中R1和R2各自为乙基。
6.权利要求5的经阻燃的柔性聚氨酯泡沫,其中R1和R2各自为乙基。
7.制品,其包括权利要求1的聚氨酯泡沫。
8.包括权利要求7的制品的应用品,其中所述应用品选自家具应用品、汽车应用品、船只应用品、公共汽车座椅应用品、列车座椅应用品、RV座椅应用品、办公家具座椅应用品、航空应用品、牵引车应用品、自行车应用品、发动机架应用品、压缩机应用品、寝具应用品、隔离应用品、体育用品应用品、鞋应用品、地毯衬垫应用品、包装应用品、织物应用品、缓冲减震应用品、HVAC应用品、帐篷应用品、救生筏应用品、行李应用品和手袋应用品,其包含权利要求1的柔性聚氨酯。
9.权利要求8的家具应用品,其为装有垫子的家具。
10.权利要求8的汽车应用品,其选自汽车座垫、顶衬和头枕、汽车和卡车用的背垫、公共汽车座椅、交通工具座椅的底部和靠背靠垫、扶手、安全轮胎的支承环、和其他汽车内部构件。
11.权利要求8的寝具应用品,其选自床垫和床垫顶部应用品。
12.权利要求8的隔离应用品,其为隔音材料。
14.权利要求13的经阻燃的柔性聚氨酯泡沫,其中R1和R2各自为乙基。
15.制品,其包括权利要求13的聚氨酯泡沫。
16.包括权利要求15的制品的应用品,其中所述应用品选自家具应用品、汽车应用品、船只应用品、公共汽车座椅应用品、列车座椅应用品、RV座椅应用品、办公家具座椅应用品、航空应用品、牵引车应用品、自行车应用品、发动机架应用品、压缩机应用品、寝具应用品、隔离应用品、体育用品应用品、鞋应用品、地毯衬垫应用品、包装应用品、织物应用品、缓冲减震应用品、HVAC应用品、帐篷应用品、救生筏应用品、行李应用品和手袋应用品,其包括权利要求1的柔性聚氨酯。
17.权利要求16的家具应用品,其为装有垫子的家具。
18.权利要求16的汽车应用品,其选自汽车座垫、顶衬和头枕、汽车和卡车用的背垫、公共汽车座椅、交通工具座椅的底部和靠背靠垫、扶手、安全轮胎的支承环、和其他汽车内部构件。
19.权利要求16的寝具应用品,其选自床垫和床垫顶部应用品。
20.权利要求16的隔离应用品,其为隔音材料。
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US20210079301A1 (en) | 2021-03-18 |
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JP7182601B2 (ja) | 2022-12-02 |
US10899911B2 (en) | 2021-01-26 |
CN111194329A (zh) | 2020-05-22 |
US20190119468A1 (en) | 2019-04-25 |
WO2019023091A1 (en) | 2019-01-31 |
JP2020528482A (ja) | 2020-09-24 |
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US20190023873A1 (en) | 2019-01-24 |
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