CN1708503A - 低聚磷酸酯组合物结晶的延迟 - Google Patents

低聚磷酸酯组合物结晶的延迟 Download PDF

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Publication number
CN1708503A
CN1708503A CN200380102119.XA CN200380102119A CN1708503A CN 1708503 A CN1708503 A CN 1708503A CN 200380102119 A CN200380102119 A CN 200380102119A CN 1708503 A CN1708503 A CN 1708503A
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Prior art keywords
bridge joint
oligomeric phosphate
alkylene
bridged
phosphate composition
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谢尔盖·列夫奇克
杰拉尔德·R·阿莱西奥
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Ripplewood Phosphorus US LLC
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Akzo Nobel NV
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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
    • C08K5/52—Phosphorus bound to oxygen only
    • C08K5/521—Esters of phosphoric acids, e.g. of H3PO4
    • C08K5/523—Esters of phosphoric acids, e.g. of H3PO4 with hydroxyaryl compounds
    • 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
    • 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
    • C07F9/06—Phosphorus compounds without P—C bonds
    • C07F9/08—Esters of oxyacids of phosphorus
    • C07F9/09—Esters of phosphoric acids
    • C07F9/12—Esters of phosphoric acids with hydroxyaryl compounds
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K21/00—Fireproofing materials
    • C09K21/06—Organic materials
    • C09K21/12—Organic materials containing phosphorus
    • 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
    • C08K2201/00—Specific properties of additives
    • C08K2201/014—Additives containing two or more different additives of the same subgroup in C08K

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Molecular Biology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Biochemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Polymers & Plastics (AREA)
  • Medicinal Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Compositions Of Macromolecular Compounds (AREA)

Abstract

本发明提供了延迟低聚磷酸酯组合物结晶的方法，其中在一段时间内，与贮存包括亚芳基桥接的低聚磷酸酯组合物而不含亚烷基桥接的二磷酸酯的组合物相比，贮存包括亚芳基桥接的低聚磷酸酯组合物和有效量的亚烷基桥接的二磷酸酯的共混物延迟了结晶的发生。

Description

低聚磷酸酯组合物结晶的延迟
技术领域
本发明涉及含有亚芳基桥接的低聚磷酸酯阻燃剂的组合物的结晶的延迟，该组合物可用作例如工程树脂中的阻燃添加剂。
背景技术
亚芳基桥接的低聚磷酸酯组合物如双酚A二(二苯基磷酸酯)在贮存时倾向于结晶，如W.B.Harrod等人的美国专利6,319,432第2栏第1-5行所述。已知在工程树脂如含聚碳酸酯的聚合物组合物中使用这种低聚磷酸酯作为阻燃剂。还已知使用亚烷基桥接的组合物和亚芳基桥接的组合物的共混物(例如，参见PCT专利公开WO96/11977，该文献没有说明或暗示通过添加这种亚烷基桥接的低聚磷酸酯组合物来延迟亚芳基桥接的低聚磷酸酯组合物的结晶，这将在下文阐述)。
发明内容
本发明涉及通常随时间的进行而结晶的亚芳基桥接的低聚磷酸酯组合物的结晶的延迟，通过将足够量的亚烷基桥接的低聚磷酸酯添加到亚芳基桥接的低聚磷酸酯组合物中实现这一技术效果。
结晶行为可得到改善的亚芳基桥接的低聚磷酸酯组合物如下式所示：
其中R1，R2，R3，R4各自为芳基或取代的芳基，X是衍生自包括亚芳基部分的二醇的桥接基团，n优选为约1-约5。上式中的基团-O-X-O-可衍生自如氢醌、间苯二酚和双酚A的二醇。
上述类型的磷酸酯组合物在贮存时，其结晶通过向其中引入有效量(约10重量％-约80重量％)的下式所示的亚烷基桥接的低聚磷酸酯组合物可得到延迟，
其中R1，R2，R3，R4各自为芳基或取代的芳基，X是衍生自包括亚烷基部分的二醇的桥接基团，n优选为1。上式中的基团-O-X-O-可衍生自如新戊二醇的二醇。
尽管亚烷基桥接的二磷酸酯与亚芳基桥接的低聚磷酸酯组合物的混合物已在先前的用于改善低聚磷酸酯阻燃剂的粘度的PCT WO96/11996中公开，但是亚烷基桥接的二磷酸酯延迟结晶的这一效果是意想不到的。上述PCT公开没有讨论当亚烷基桥接的二磷酸酯与亚芳基桥接的低聚磷酸酯组合物的共混物在一段时间内贮存时所述亚烷基桥接的二磷酸酯的效果，例如，纯的亚芳基桥接的低聚磷酸酯组合物在贮存一段时间后通常会结晶。
如上所述，用于本文应用的优选的亚烷基桥接的二磷酸酯为下式表示的新戊二醇二(二苯基磷酸酯)，
这一产品最优选为含有多于80重量％的上式所示的二磷酸酯、低于5重量％的环状产品 以及低于8重量％的三苯基磷酸酯的液体产品。
本发明进一步通过以下实施例进行说明。
具体实施方式
实施例1-6
双酚A二(二苯基磷酸酯)，“BDP”，和新戊二醇二(二苯基磷酸酯)，“NDP”以下表1所示的不同比例进行混合。在55℃和70℃下测量单一的芳族二磷酸酯及其共混物的粘度。将BDP/NDP的混合物倾入到50ml试管中，盖上盖子并置于-15℃的实验室冷冻机中。以与处理BDP/NDP的混合物相同的方式处理单一的BDP和单一的DNP(实施例1和2，作为比较例)。粘度测量结果以及冷冻测量结果如表1所示。
    #     芳族二磷酸酯               粘度，厘泊   冷冻时间天数
    55℃     70℃
    1   BDP     420     181     1天
    2   NDP     50     26     ＞300
    3   BDP/NDP＝4∶1     229     97     ＞300
    4   BDP/NDP＝3∶2     178     71     ＞300
    5   BDP/NDP＝2∶3     98     47     ＞300
    6   BDP/NDP＝1∶4     71     36     ＞300
BDP：双酚A二(二苯基磷酸酯)
NDP：新戊二醇二(二苯基磷酸酯)
NDP也有助于显著地降低BDP的粘度，其有益于芳族二磷酸酯的处理，特别有益于在化合过程中使芳族二磷酸酯泵入到挤出物中。
BDP/NDP混合物在低温下长期贮存时不结冻，因此这些混合物在贮存时不需要受热罐，在运输时不需要热跟踪线路。
上述实施例仅是说明本发明的某些实施方案，其不构成对本发明的限制。本发明的范围在权利要求书中阐述。

Claims (5)

1.在一段时间内，与贮存包含亚芳基桥接的低聚磷酸酯组合物而不含有亚烷基桥接的二磷酸酯的组合物相比，贮存包含亚芳基桥接的低聚磷酸酯组合物和有效量的亚烷基桥接的二磷酸酯的共混物用于延迟结晶发生的时间的方法。
2.根据权利要求1所述的方法，其中亚芳基桥接的低聚磷酸酯组合物含有衍生自双酚A的桥接基团。
3.根据权利要求1所述的方法，其中亚烷基桥接的二磷酸酯含有衍生自新戊二醇的桥接基团。
4.根据权利要求1所述的方法，其中亚芳基桥接的低聚磷酸酯组合物含有衍生自双酚A的桥接基团，并且其中亚烷基桥接的二磷酸酯含有衍生自新戊二醇的桥接基团。
5.根据权利要求1-4中任一项所述的方法，其中在共混物中亚烷基桥接的二磷酸酯的含量相对于亚芳基桥接的低聚磷酸酯组合物为约10重量％-约80重量％。
CN200380102119.XA 2002-10-26 2003-10-25 低聚磷酸酯组合物结晶的延迟 Pending CN1708503A (zh)

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WO2019082930A1 (ja) * 2017-10-25 2019-05-02 株式会社Adeka 結晶化遅延剤、これを含有する組成物、オレフィン系樹脂組成物、その成形品、およびオレフィン樹脂の結晶化の遅延方法

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DE3367782D1 (en) * 1982-10-12 1987-01-08 Ciba Geigy Ag Fire-retarding compositions
US4433071A (en) * 1982-12-14 1984-02-21 Stauffer Chemical Company Flame and dripping ember retardant flexible polyurethane foams
GB8528294D0 (en) * 1985-11-16 1985-12-18 Bp Chem Int Ltd Flame retardant phenolic foams
US5086082A (en) * 1989-09-27 1992-02-04 Pmc, Inc. Ignition resistant polyurethane foams with melamine
US6855275B1 (en) * 1989-11-14 2005-02-15 Ripplewood Phosphorus U.S. Llc Viscosity modification of high viscosity flame retardants
US5547614A (en) * 1989-11-14 1996-08-20 Akzo Nobel N.V. Flame retardant mixture of polybrominated diphenyl oxide and organic diphosphate
EP0778864B1 (en) * 1994-08-30 2000-04-12 Akzo Nobel N.V. Fog reduction in polyurethane foam using phosphate esters
WO1996011996A1 (en) * 1994-10-13 1996-04-25 Akzo Nobel Nv Viscosity modification of high viscosity flame retardants
CA2202164C (en) * 1994-10-13 2007-09-04 Paul Y. Moy Polycarbonate-containing polymers flame retarded with oligomeric phosphate esters
US5750756A (en) * 1994-11-01 1998-05-12 Akzo Nobel Nv Process for the formation of hydrocarbyl bis(hydrocarbyl phosphate)
US6319432B1 (en) * 1999-06-11 2001-11-20 Albemarle Corporation Bisphenol-A bis(diphenyl phosphate)-based flame retardant
US20050222284A1 (en) * 2002-05-07 2005-10-06 Williams Barbara A Synergistic flame retardant blends for polyurethane foams
AU2003286760A1 (en) * 2002-10-31 2004-06-07 Akzo Nobel N.V. Method of retaining the hydrolytic stability of flame retarded polymer composition

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WO2004039818A1 (en) 2004-05-13
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