CN1668625A - 环氧稳定的聚磷酸酯组合物 - Google Patents
环氧稳定的聚磷酸酯组合物 Download PDFInfo
- Publication number
- CN1668625A CN1668625A CN03816592.9A CN03816592A CN1668625A CN 1668625 A CN1668625 A CN 1668625A CN 03816592 A CN03816592 A CN 03816592A CN 1668625 A CN1668625 A CN 1668625A
- Authority
- CN
- China
- Prior art keywords
- composition
- epoxy
- poly phosphate
- arylidene
- phenyl
- 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
- 239000000203 mixture Substances 0.000 title claims abstract description 27
- 229920000388 Polyphosphate Polymers 0.000 title claims abstract description 18
- 239000001205 polyphosphate Substances 0.000 title claims abstract description 18
- 235000011176 polyphosphates Nutrition 0.000 title claims abstract description 18
- 239000004593 Epoxy Substances 0.000 claims abstract description 24
- 239000002253 acid Substances 0.000 claims abstract description 12
- 125000003118 aryl group Chemical group 0.000 claims abstract description 4
- 125000002877 alkyl aryl group Chemical group 0.000 claims abstract description 3
- YXALYBMHAYZKAP-UHFFFAOYSA-N 7-oxabicyclo[4.1.0]heptan-4-ylmethyl 7-oxabicyclo[4.1.0]heptane-4-carboxylate Chemical group C1CC2OC2CC1C(=O)OCC1CC2OC2CC1 YXALYBMHAYZKAP-UHFFFAOYSA-N 0.000 claims description 5
- MNAHQWDCXOHBHK-UHFFFAOYSA-N 1-phenylpropane-1,1-diol Chemical group CCC(O)(O)C1=CC=CC=C1 MNAHQWDCXOHBHK-UHFFFAOYSA-N 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 150000003014 phosphoric acid esters Chemical class 0.000 claims description 4
- 239000000654 additive Substances 0.000 claims description 3
- 230000000996 additive effect Effects 0.000 claims description 2
- 125000001118 alkylidene group Chemical group 0.000 claims description 2
- 239000002131 composite material Substances 0.000 claims 3
- 125000003968 arylidene group Chemical group [H]C(c)=* 0.000 claims 1
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinyl group Chemical group C1(O)=CC(O)=CC=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 claims 1
- -1 phosphate ester Chemical class 0.000 abstract description 8
- 229910019142 PO4 Inorganic materials 0.000 abstract description 4
- 239000010452 phosphate Substances 0.000 abstract description 4
- 150000002148 esters Chemical class 0.000 abstract description 2
- 125000002947 alkylene group Chemical group 0.000 abstract 1
- 125000000732 arylene group Chemical group 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 description 12
- 229920005989 resin Polymers 0.000 description 11
- 239000011347 resin Substances 0.000 description 11
- 238000000034 method Methods 0.000 description 6
- 230000007062 hydrolysis Effects 0.000 description 5
- 238000006460 hydrolysis reaction Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- OECTYKWYRCHAKR-UHFFFAOYSA-N 4-vinylcyclohexene dioxide Chemical compound C1OC1C1CC2OC2CC1 OECTYKWYRCHAKR-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000003063 flame retardant Substances 0.000 description 3
- 235000021317 phosphate Nutrition 0.000 description 3
- 239000003381 stabilizer Substances 0.000 description 3
- OXQXGKNECHBVMO-UHFFFAOYSA-N 7-oxabicyclo[4.1.0]heptane-4-carboxylic acid Chemical compound C1C(C(=O)O)CCC2OC21 OXQXGKNECHBVMO-UHFFFAOYSA-N 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- 125000006267 biphenyl group Chemical group 0.000 description 2
- 239000012757 flame retardant agent Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 125000006353 oxyethylene group Chemical group 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 239000011574 phosphorus Substances 0.000 description 2
- 229920005668 polycarbonate resin Polymers 0.000 description 2
- 239000004431 polycarbonate resin Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- MUTGBJKUEZFXGO-OLQVQODUSA-N (3as,7ar)-3a,4,5,6,7,7a-hexahydro-2-benzofuran-1,3-dione Chemical compound C1CCC[C@@H]2C(=O)OC(=O)[C@@H]21 MUTGBJKUEZFXGO-OLQVQODUSA-N 0.000 description 1
- 150000005207 1,3-dihydroxybenzenes Chemical class 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- BNDNAARXJVXTED-UHFFFAOYSA-N 7-oxabicyclo[4.1.0]heptan-4-yl 4-methyl-7-oxabicyclo[4.1.0]heptane-4-carboxylate Chemical compound C1CC2OC2CC1OC(=O)C1(C)CC2OC2CC1 BNDNAARXJVXTED-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 239000004902 Softening Agent Substances 0.000 description 1
- 239000004809 Teflon Substances 0.000 description 1
- 229920006362 Teflon® Polymers 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 229940058344 antitrematodals organophosphorous compound Drugs 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000004646 arylidenes Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- ZJIPHXXDPROMEF-UHFFFAOYSA-N dihydroxyphosphanyl dihydrogen phosphite Chemical compound OP(O)OP(O)O ZJIPHXXDPROMEF-UHFFFAOYSA-N 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 description 1
- 238000011010 flushing procedure Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 125000005456 glyceride group Chemical group 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 150000002903 organophosphorus compounds Chemical class 0.000 description 1
- 150000002924 oxiranes Chemical class 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical class OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical compound FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
Classifications
-
- 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
- C07F9/025—Purification; Separation; Stabilisation; Desodorisation of organo-phosphorus compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Epoxy Resins (AREA)
- Epoxy Compounds (AREA)
Abstract
一种聚磷酸酯组合物，其主要由聚磷酸酯和有效量的用于降低组合物总酸值的环脂族环氧组合物组成。其中磷酸酯用如上通式表示，其中R是芳基和烷芳基，R′是亚芳基、亚芳基－亚烷基－亚芳基、或亚烷基，n为约1～约5。
Description
发明背景
现知将环氧化合物作为稳定剂加入用作功能流体的一磷酸酯化合物中。描述这种方法的专利的例子包括：W.F.Gentit的美国专利3,637,507、M.L.Burrous的美国专利3,932,294和W.F.Gentit等的美国专利3,941,708。
现知一类完全不同的聚磷酸酯化合物，其具有如下通式：
其中n按平均值其范围约1～约5；R为芳基，如苯基或烷芳基；和R′为亚芳基(例如间苯二酚的衍生物)、亚芳基-亚烷基-亚芳基(例如双酚A的衍生物)、或亚烷基(例如新戊亚基)。这些磷酸酯例如可用作阻燃剂和作为塑料的增塑剂。它们易于水解产生磷酸，而磷酸是不期望的降解产物。这些酸种类会导致聚碳酸酯树脂的分解。
已公开了解决上述降解问题的各种方法。通用电器公司的欧洲专利909,790公开了向包括所述磷酸酯和所述树脂的组合物中加入酸清除剂，如环氧化合物。T.Koyama的美国专利5,871,570公开了相似的方法，其中不包括卤素的环氧化合物被加到聚碳酸酯树脂组合物中，所述的组合物含有机磷型阻燃剂和其他添加剂。日本公开专利申请2001/2945公开了将脂环族环氧化合物加到也含有机磷型阻燃剂的树脂组合物中。这些常规方法中，仅当其在成为也预期含有阻燃剂树脂体系的情况下，环氧化合物才被加入聚磷酸酯中。
当其形成后在其制备过程中的某位置可用另一种方法将环氧化合物加到聚磷酸酯中。Daihachi的PCT申请专利2001/12638描述了先用环氧化合物然后用碱性水溶液处理磷酸酯化合物。S.Kawata的美国专利5,616,768公开了用环氧化合物处理粗制磷酸酯产物、在水存在下加热得到的产物、用水冲洗得到的产物、然后除去残留水。日本公开专利申请2001/151,786公开了芳族磷酸酯组合物，其通过加入二亚磷酸双(2，4-二-叔丁基苯基)季戊四醇酯和3，4-环氧环己基甲基3，4-环氧环己烷羧酸酯来稳定。
日本专利公开2001/131,392(2001年5月15日)阐述了包括有机磷化合物和环氧化合物的阻燃剂组合物，其酸值为1或更低。
发明内容：
本申请涉及通过加入某类环氧稳定剂而被稳定的聚磷酸酯组合物。本发明将聚磷酸酯/环氧稳定剂预混合，然后加到基材树脂中(例如工程树脂)来稳定最终的阻燃树脂制剂。
此处选择的环氧稳定剂为一种或多种具有C6～C10环脂族环的环脂族环氧化合物。它们为脂环族环氧化合物，其中脂环族环氧结构单元通过键合单元连接，其中的键合单元可为二氧杂环己烷，或羧基结构单元。有用的环脂族环氧化合物的例子包括：3，4-环氧环己基甲基3，4-环氧环己烷羧酸酯，其以ERL-4221(Union Carbide Corporation的商标)和ARALDITECY-179(Ciba-Geigy的商标)购买；六氢邻苯二甲酸酐的二环氧甘油脂，其以CY-184(Ciba-Geigy的商标)购买；二(3，4-环氧环己基甲基)己二酸，其以ERL-4299(Union Carbide Corporation的商标)购买；二氧化乙烯基环己烯(ERL-4206)；一氧化乙烯基环己烯；和2-[3，4-环氧环己基-5，5-螺-3，4-环氧]-环己烷-间-二氧杂环己烷(ERL-4234)。通常，这类环氧组份选自环脂族环氧化物(包括双环氧化合物)。这类结构的例子如下：
ERL-4221 ERL-4299
ERL-4206
单氧化乙烯基环乙烯
ERL-4234
优选向这些聚磷酸酯中加入3，4-环氧环己基甲基3，4-环氧环己烷羧酸酯(从Union Carbide购买的型号为ERL 4221)，防止在高温和高湿度下生成酸，得到高水解稳定性的聚磷酸酯，如果需要，然后可将其加到树脂中以稳定得到的树脂。
一般地讲，环氧化合物的用量为聚磷酸酯组合物质量的约0.01wt％～约1％。聚磷酸酯和环氧添加剂的混合物可有益地在高于约室温～150℃下分别保持约8小时～约15分钟。
本发明稳定的聚磷酸酯组合物，例如在90℃下用水处理35天后，酸度没有增加，从而表明其具有极好的水解稳定性。
通过下述实施例可更好地理解本申请。
实施例1
双酚A双(二苯基磷酸酯)，497.5g，酸值为0.059mg KOH/g，和2.5g的3，4-环氧环己基甲基3，4-环氧环己烷羧酸酯(从Union Carbide购买的商标为ERL-4221)在40℃下混合，并搅拌4小时。然后测量的酸值为0.044mg KOH/g。
实施例2
将与实施例1等量的相同的双酚A双(二苯基磷酸酯)，其酸值为0.059mg KOH/g，和2.5g从Dow Chemical购买的DER-732型环氧树脂(聚乙二醇环氧树脂)在40℃下混合，并搅拌4小时。然后测量的酸值为0.047mg KOH/g。
环氧稳定的聚磷酸酯的水解稳定性试验
通过下面测试过程来比较所述材料与未经处理材料的水解稳定性：
向1升树脂瓶加入400g所述磷酸酯和4g(1wt.％)的去离子水。该树脂罐安装有机械搅拌器(玻璃棒，TEFLON碳氟化合物浆片)和确保系统气密性的橡胶隔片。将瓶浸在93℃的油浴中。以120～150rpm的转速搅拌混合物。
定期取样以分析总酸值(TAN)。使用约0.01M的氢氧化钠溶液滴定至浅绿色终点，使用萘酚苯指示剂(ASTM方法D948)。数据总结如下：
结果
| 时间(天) | 未处理的BDP(mg.KOH/g) | 样品1(mg.KOH/g) | 样品2(mg.KOH/g) |
| 0 | 0.059 | 0.044 | 0.047 |
| 2 | 0.074 | 0.001 | 0.035 |
| 7 | 0.127 | 0.001 | 0.475 |
| 9 | 0.159 | 0.001 | 0.608 |
| 13 | 0.246 | 0.001 | 1.147 |
| 15 | 0.317 | 0.001 | 1.140 |
| 23 | 0.85 | 0.002 | -- |
| 30 | 1.39 | 0.002 | -- |
| 35 | 2.07 | 0.003 | -- |
上述实施例仅提供了本发明的某些优选实施方式，因此不应当理解为对本发明的限制。本发明的保护范围参见所附权利要求。
Claims (9)
1.一种稳定的聚磷酸酯组合物，其主要由聚磷酸酯和有效量的用于降低组合物总酸值的环脂族环氧组合物组成。
2.根据权利要求1的组合物，其中磷酸酯可用如下通式表示：
其中R选自芳基和烷芳基，R′选自亚芳基、亚芳基-亚烷基-亚芳基和亚烷基，n为约1～约5。
3.根据权利要求2的组合物，其中R为苯基，-O-R-O-为双酚A部分。
4.根据权利要求2的组合物，其中R为苯基，-O-R-O-为间苯二酚部分。
5.根据权利要求2的组合物，其中R为苯基，-O-R-O-为新戊基乙二醇部分。
6.根据权利要求2的组合物，其中R为2，6-二甲苯酚。
7.根据权利要求1～6中任一项的组合物，其中环氧组合物为3，4-环氧环己基甲基3，4-环氧环己烷羧酸酯。
8.根据权利要求1～6中任一项的组合物，其中环氧组合物的用量为聚磷酸酯组合物重量的约0.01％～约1％。
9.根据权利要求1～6中任一项的组合物，其中聚磷酸酯和环氧添加剂一起可在温度为约高于室温～150℃下分别保持约8小时～约15分钟。
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10/144,568 | 2002-05-13 | ||
| US10/144,568 US6717005B2 (en) | 2002-05-13 | 2002-05-13 | Epoxy-stabilized polyphosphate compositions |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN1668625A true CN1668625A (zh) | 2005-09-14 |
Family
ID=29400360
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN03816592.9A Pending CN1668625A (zh) | 2002-05-13 | 2003-05-06 | 环氧稳定的聚磷酸酯组合物 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US6717005B2 (zh) |
| EP (1) | EP1554292A2 (zh) |
| JP (1) | JP4481246B2 (zh) |
| CN (1) | CN1668625A (zh) |
| AU (1) | AU2003304244A1 (zh) |
| TW (1) | TW200404867A (zh) |
| WO (1) | WO2005000994A2 (zh) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7166736B2 (en) * | 2002-05-07 | 2007-01-23 | Supresta Llc | Neopentylglycol bis(diaryl phosphate) esters |
| AU2003286760A1 (en) * | 2002-10-31 | 2004-06-07 | Akzo Nobel N.V. | Method of retaining the hydrolytic stability of flame retarded polymer composition |
| US20090217705A1 (en) * | 2008-02-29 | 2009-09-03 | Filippov Andrey V | Temperature control of glass fusion by electromagnetic radiation |
| TWI475052B (zh) * | 2011-12-22 | 2015-03-01 | Frx Polymers Inc | 寡聚膦酸酯及包含該寡聚膦酸酯之組成物 |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3637507A (en) | 1968-02-12 | 1972-01-25 | Stauffer Chemical Co | Aircraft hydraulic fluid and method of controlling acid buildup therein with acid acceptor |
| US3932294A (en) | 1974-01-11 | 1976-01-13 | Chevron Research Company | Functional fluid containing a hydrolysis suppressor |
| US3941708A (en) | 1974-02-11 | 1976-03-02 | Stauffer Chemical Company | Hydraulic fluid antioxidant system |
| US4696963A (en) | 1985-10-10 | 1987-09-29 | Great Lakes Chemical Corporation | Halogenated alkyl phosphate esters and polymer systems incorporating them |
| US4992496A (en) | 1987-09-03 | 1991-02-12 | Fmc Corporation | Flame retardant modified polyphenylene oxide composition |
| DE69318555T3 (de) | 1992-06-11 | 2008-02-21 | Solutia Inc. | Funktionelle fluessigkeit |
| US5616768A (en) | 1994-06-23 | 1997-04-01 | Daihachi Chemical Industry Co., Ltd. | Process for purifying phosphoric esters |
| JPH08319406A (ja) | 1995-05-26 | 1996-12-03 | Kanegafuchi Chem Ind Co Ltd | 難燃性樹脂組成物 |
| US6613820B2 (en) * | 1997-08-29 | 2003-09-02 | General Electric Company | Polycarbonate resin composition |
| MY121010A (en) * | 1997-08-29 | 2005-12-30 | Sabic Innovative Plastics Ip | Polycarbonate resin composition |
| SG85605A1 (en) | 1997-10-16 | 2002-01-15 | Gen Electric | Flame resistant compositions of polycarbonate and monovinylidene aromatic compounds |
| JP2001002945A (ja) | 1999-06-23 | 2001-01-09 | Asahi Chem Ind Co Ltd | 安定化された難燃性樹脂組成物 |
| JP4518601B2 (ja) | 1999-11-05 | 2010-08-04 | 旭化成ケミカルズ株式会社 | 難燃剤組成物とそれを用いた樹脂組成物の製造法 |
| JP4089998B2 (ja) | 1999-11-22 | 2008-05-28 | 大八化学工業株式会社 | 熱安定性に優れた縮合型芳香族ホスフェート組成物 |
| MXPA02011080A (es) | 2000-05-09 | 2003-03-10 | Solutia Inc | Composiciones de fluidos funcionales, que contienen depuradores expoxidicos de acidos. |
| JP2005502588A (ja) * | 2001-02-08 | 2005-01-27 | アクゾ ノーベル ナムローゼ フェンノートシャップ | リン酸エステルの精製方法 |
-
2002
- 2002-05-13 US US10/144,568 patent/US6717005B2/en not_active Expired - Lifetime
-
2003
- 2003-05-06 WO PCT/US2003/014147 patent/WO2005000994A2/en not_active Application Discontinuation
- 2003-05-06 EP EP03816981A patent/EP1554292A2/en not_active Withdrawn
- 2003-05-06 JP JP2005503251A patent/JP4481246B2/ja not_active Expired - Fee Related
- 2003-05-06 AU AU2003304244A patent/AU2003304244A1/en not_active Abandoned
- 2003-05-06 CN CN03816592.9A patent/CN1668625A/zh active Pending
- 2003-05-13 TW TW092112938A patent/TW200404867A/zh unknown
Also Published As
| Publication number | Publication date |
|---|---|
| JP2006510739A (ja) | 2006-03-30 |
| AU2003304244A1 (en) | 2005-01-13 |
| EP1554292A2 (en) | 2005-07-20 |
| JP4481246B2 (ja) | 2010-06-16 |
| AU2003304244A8 (en) | 2005-01-13 |
| US6717005B2 (en) | 2004-04-06 |
| US20030212287A1 (en) | 2003-11-13 |
| TW200404867A (en) | 2004-04-01 |
| WO2005000994A2 (en) | 2005-01-06 |
| WO2005000994A3 (en) | 2005-04-28 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP1627896B1 (de) | Intumeszenzbrandschutzbeschichtung enthaltend Phosphor/Stickstoff-Flammschutzmittel und ein Phosphinsäuresalz | |
| CN100562541C (zh) | 阻燃型有机硅改性丙烯酸树脂乳液及其制备方法 | |
| EP2563877B1 (de) | Flammschutzmittel-stabilisator-kombination für thermoplastische und duroplastische polymere | |
| EP2563876B1 (de) | Flammschutzmittel-stabilisator-kombination für thermoplastische und duroplastische polymere | |
| CN1656165A (zh) | 用于聚氨酯泡沫的(烷基取代)三芳基磷酸酯与含磷阻燃剂的共混物 | |
| US7910665B2 (en) | Composition of epoxy resin and epoxy-reactive polyphosphonate | |
| US6242631B1 (en) | Triaryl phosphate ester composition | |
| KR20090004917A (ko) | 난연제 첨가제 조성물 및 그의 용도 | |
| EP0778864A1 (en) | Fog reduction in polyurethane foam using phosphate esters | |
| CN1795223A (zh) | 用于环氧树脂的聚膦酸酯阻燃固化剂 | |
| JP2015507029A (ja) | 難燃性コポリエーテルエステル組成物、及びこれを含む物品 | |
| JP5319717B2 (ja) | 希土類トリス（有機リン誘導体）の安定溶液 | |
| CN1668625A (zh) | 环氧稳定的聚磷酸酯组合物 | |
| CA2409858C (en) | Polyester resin composition and process for the preparation thereof | |
| CN111518316A (zh) | 环保塑料阻燃剂、制备方法及其在塑料中的应用 | |
| US7759522B2 (en) | Process for purification of phosphate esters | |
| WO1996011996A1 (en) | Viscosity modification of high viscosity flame retardants | |
| KR20050062756A (ko) | 에폭시로 안정화된 폴리포스페이트 조성물 | |
| US4664828A (en) | Antiwear additives for functional fluids | |
| JPH021761A (ja) | ホスホン酸のリチウム塩を含むポリマー組成物及び該リチウム塩 | |
| JP2001064511A (ja) | 室温硬化性オルガノポリシロキサン組成物及びその製造方法 | |
| US6855275B1 (en) | Viscosity modification of high viscosity flame retardants | |
| CN114262429B (zh) | 一种低烟量碳酸酯组合物的制备方法及其应用 | |
| EP1115728B1 (en) | Triaryl phosphate ester composition | |
| CN1315924C (zh) | 保持阻燃聚合物组合物水解稳定性的方法 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| ASS | Succession or assignment of patent right |
Owner name: LE GI PROEKT VODOKHOZYAJSTVENN Free format text: FORMER OWNER: AKZO NOBEL NV Effective date: 20060811 |
|
| C41 | Transfer of patent application or patent right or utility model | ||
| TA01 | Transfer of patent application right |
Effective date of registration: 20060811 Address after: American New York Applicant after: Supresta LLC Address before: Holland Arnhem Applicant before: Akzo Nobel NV |
|
| C02 | Deemed withdrawal of patent application after publication (patent law 2001) | ||
| WD01 | Invention patent application deemed withdrawn after publication |