CN109651589B - 一种含n、p阻燃水性聚氨酯的制备方法 - Google Patents

一种含n、p阻燃水性聚氨酯的制备方法 Download PDF

Info

Publication number
CN109651589B
CN109651589B CN201811524760.7A CN201811524760A CN109651589B CN 109651589 B CN109651589 B CN 109651589B CN 201811524760 A CN201811524760 A CN 201811524760A CN 109651589 B CN109651589 B CN 109651589B
Authority
CN
China
Prior art keywords
flame
retardant
hours
reacting
waterborne 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.)
Active
Application number
CN201811524760.7A
Other languages
English (en)
Other versions
CN109651589A (zh
Inventor
姚伯龙
陈昆
刘嘉成
胡旭灿
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Jiangnan University
Original Assignee
Jiangnan University
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Jiangnan University filed Critical Jiangnan University
Priority to CN201811524760.7A priority Critical patent/CN109651589B/zh
Publication of CN109651589A publication Critical patent/CN109651589A/zh
Application granted granted Critical
Publication of CN109651589B publication Critical patent/CN109651589B/zh
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • 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
    • C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
    • C08G18/75—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic
    • C08G18/751—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring
    • C08G18/752—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group
    • C08G18/753—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group containing one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group having a primary carbon atom next to the isocyanate or isothiocyanate group
    • C08G18/755—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group containing one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group having a primary carbon atom next to the isocyanate or isothiocyanate group and at least one isocyanate or isothiocyanate group linked to a secondary carbon atom of the cycloaliphatic ring, e.g. isophorone diisocyanate
    • 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
    • C08G18/30—Low-molecular-weight compounds
    • C08G18/34—Carboxylic acids; Esters thereof with monohydroxyl compounds
    • C08G18/348—Hydroxycarboxylic 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
    • C08G18/30—Low-molecular-weight compounds
    • C08G18/38—Low-molecular-weight compounds having heteroatoms other than oxygen
    • C08G18/3878—Low-molecular-weight compounds having heteroatoms other than oxygen having phosphorus
    • C08G18/3889—Low-molecular-weight compounds having heteroatoms other than oxygen having phosphorus having nitrogen in addition to phosphorus
    • 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
    • C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
    • C08G18/44—Polycarbonates
    • 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
    • C08G18/61—Polysiloxanes
    • 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
    • C08G18/65—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen
    • C08G18/66—Compounds of groups C08G18/42, C08G18/48, or C08G18/52
    • C08G18/6633—Compounds of group C08G18/42
    • C08G18/6659—Compounds of group C08G18/42 with compounds of group C08G18/34
    • 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
    • C08G18/67—Unsaturated compounds having active hydrogen
    • C08G18/671—Unsaturated compounds having only one group containing active hydrogen
    • C08G18/672—Esters of acrylic or alkyl acrylic acid having only one group containing active hydrogen
    • C08G18/673—Esters of acrylic or alkyl acrylic acid having only one group containing active hydrogen containing two or more acrylate or alkylacrylate ester groups

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Polyurethanes Or Polyureas (AREA)
  • Compositions Of Macromolecular Compounds (AREA)

Abstract

一种含N、P阻燃水性聚氨酯的制备方法，属于高分子材料技术领域。本发明通过六氯环三磷氰与三聚氰胺发生取代反应生成阻燃的十二臂型阻燃单体，然后合成多臂型阻燃水性聚氨酯。磷腈类化合物其结构中的磷、氮元素具有协同阻燃效应，故可得到较好的热稳定性和阻燃性能，而且在热分解时不产生毒性较大的物质，符合人们对阻燃剂低毒、低污染、低腐蚀性的要求。

Description

一种含N、P阻燃水性聚氨酯的制备方法
技术领域
本发明一种含N、P阻燃水性聚氨酯的制备方法，涉及一种多臂型水性聚氨酯的制备方法，具体内容是十二臂型阻燃单体的制备和阻燃水性聚氨酯的制备，属于高分子材料技术领域。
背景技术
材料的阻燃是长期以来科学研究中的重要课题。传统卤素阻燃剂在阻燃过程中会产生有毒物质，为了满足目前对环境保护的要求，阻燃剂的无卤化已成为发展趋势。近年来，含磷阻燃剂因其优异的阻燃性能，逐渐成为研究者的研究热点。环三磷腈化合物是一类由磷、氮原子以单、双键交替键合而成的环状化合物，分子中有三个磷原子，通过在磷原子上连接不同的官能团，得到不同的功能性化合物。磷腈类化合物其结构中的磷、氮元素具有协同阻燃效应，故可得到较好的热稳定性和阻燃性能，而且在热分解时不产生毒性较大的物质，符合人们对阻燃剂低毒、低污染、低腐蚀性的要求。
发明内容
本发明在于克服现有技术的不足，提供一种含N、P阻燃水性聚氨酯的制备方法。该方法中通过六氯环三磷氰与三聚氰胺发生取代反应生成阻燃的十二臂型阻燃单体，然后合成多臂型阻燃水性聚氨酯。
本发明的技术方案：一种含N、P阻燃水性聚氨酯的制备方法，包括如下步骤：
（1）十二臂型阻燃单体的制备：加入适量的六氯环三磷氰到装有搅拌棒的四颈烧瓶中，然后加入与氯等摩尔的缚酸剂，加热到90℃，再取一定量的三聚氰胺用适量的N-甲基吡咯烷酮超声溶解，滴加到反应烧瓶中，反应13h。再将产物抽滤，得到固体用乙醇和去离子水各洗三遍，离心，抽滤，放入真空烘箱中干燥24h，得到淡黄色粉末，即为一种十二臂型阻燃单体。
该合成步骤中缚酸剂可以为碳酸钾，碳酸钠，三乙胺中的一种。
（2）水性阻燃聚氨酯的制备：称取适量的异佛尔酮二异氰酸酯（IPDI）放入装有搅拌棒的四颈烧瓶中，加入二月桂酸二丁基锡（DBTDL），通入氮气。第一步滴加一定量的聚碳酸酯二元醇（PCDL）和端羟基聚醚改性硅油（PDMS），加热到45℃，反应2.5h。第二步升温到67℃，滴加一定量的2，2-二羟甲基丁酸（DMPA），反应3h。第三步加入4-甲氧基苯酚（MEHQ），滴加一定量的季戊四醇三丙烯酸酯（PETA），反应4h。第四步滴加一定量的上述自制的十二臂型阻燃单体，反应5h。第五步让温度降至室温，在600r/min高速搅拌下加入适量的三乙胺（TEA），反应35min。最后，加入一定量的去离子水进行乳化，高速搅拌2h后，静置24h，得到淡蓝色的含N、P阻燃水性聚氨酯。
本发明的有益效果：所得产品具有较好的热稳定性和阻燃性能，而且在热分解时不产生毒性较大的物质，符合人们对阻燃剂低毒、低污染、低腐蚀性的要求。
具体实施方式
实施例1
（1）一种十二臂型阻燃单体的制备：加入10.41g的六氯环三磷氰到装有搅拌棒的四颈烧瓶中，加入20mL的N-甲基吡咯烷酮搅拌溶解，然后加入24.84g的碳酸钾，加热到90℃，再取22.68g的三聚氰胺用20mL的N-甲基吡咯烷酮超声溶解，以2滴每秒的速度滴加到反应烧瓶中，反应13h。反应结束将产物抽滤，得到固体用乙醇和去离子水各洗三遍，离心，抽滤，放入真空烘箱中干燥24h，得到淡黄色粉末，即为一种十二臂型阻燃单体。
（2）一种水性阻燃聚氨酯的制备：称取35.56g的异佛尔酮二异氰酸酯（IPDI）放入装有搅拌棒的四颈烧瓶中，加入12-15滴二月桂酸二丁基锡（DBTDL），通入氮气。第一步滴加32g的聚碳酸酯二元醇（PCDL）和13.45g的端羟基聚醚改性硅油（PDMS），加热到45℃，反应2.5h。第二步升温到67℃，滴加5.36g的2，2-二羟甲基丁酸（DMPA），反应3h。第三步加入3-4滴4-甲氧基苯酚（MEHQ），滴加12g的季戊四醇三丙烯酸酯（PETA），反应4h。第四步滴加2.1g的上述自制的十二臂型阻燃单体，反应5h。第五步让温度降至室温，在高速搅拌下加入4.6g的三乙胺（TEA），反应35min。最后，加入200g的去离子水进行乳化，高速搅拌2h后，静置24h，得到淡蓝色的含N、P阻燃水性聚氨酯。

Claims (3)

1.一种含N、P阻燃水性聚氨酯的制备方法，其特征在于包括如下步骤：
（1）十二臂型阻燃单体的制备：加入适量的六氯环三磷氰到装有搅拌棒的四颈烧瓶中，然后加入与氯等摩尔的缚酸剂，加热到90℃；再取一定量的三聚氰胺用适量的N-甲基吡咯烷酮超声溶解，滴加到烧瓶中，反应13h；再将产物抽滤，所得固体用乙醇及去离子水各洗三遍，离心，抽滤，放入真空烘箱中干燥24h，得到淡黄色粉末，即为一种十二臂型阻燃单体；
（2）阻燃水性聚氨酯的制备：称取适量的异佛尔酮二异氰酸酯IPDI放入装有搅拌棒的四颈烧瓶中，加入二月桂酸二丁基锡DBTDL，通入氮气；第一步滴加一定量的聚碳酸酯二元醇PCDL和端羟基聚醚改性硅油PDMS，加热到45℃，反应2.5h；第二步升温到67℃，滴加一定量的2，2-二羟甲基丁酸DMBA，反应3h；第三步加入4-甲氧基苯酚MEHQ，滴加一定量的季戊四醇三丙烯酸酯PETA，反应4h；第四步滴加一定量的上述步骤（1）制备的十二臂型阻燃单体，反应5h；第五步让温度降至室温，在600r/min搅拌下加入适量的三乙胺TEA，反应35min；最后，加入一定量的去离子水进行乳化，高速搅拌2h后，静置24h，得到淡蓝色的含N、P阻燃水性聚氨酯。
2.根据权利要求1所述含N、P阻燃水性聚氨酯的制备方法，其特征在于，具体步骤如下：
（1）十二臂型阻燃单体的制备：加入10.41g的六氯环三磷氰到装有搅拌棒的四颈烧瓶中，加入20mL的N-甲基吡咯烷酮搅拌溶解，然后加入24.84g的碳酸钾，加热到90℃，再取22.68g的三聚氰胺用20mL的N-甲基吡咯烷酮超声溶解，以2滴每秒的速度滴加到烧瓶中，反应13h；反应结束将产物抽滤，所得固体用乙醇及去离子水各洗三遍，离心，抽滤，放入真空烘箱中干燥24h，得到淡黄色粉末，即为一种十二臂型阻燃单体；
（2）阻燃水性聚氨酯的制备：称取35.56g的异佛尔酮二异氰酸酯IPDI放入装有搅拌棒的四颈烧瓶中，加入12-15滴二月桂酸二丁基锡DBTDL，通入氮气；第一步滴加32g的聚碳酸酯二元醇PCDL和13.45g的端羟基聚醚改性硅油PDMS，加热到45℃，反应2.5h；第二步升温到67℃，滴加5.36g的2，2-二羟甲基丁酸DMBA，反应3h；第三步加入3-4滴4-甲氧基苯酚MEHQ，滴加12g的季戊四醇三丙烯酸酯PETA，反应4h；第四步滴加2.1g的上述步骤（1）制备的十二臂型阻燃单体，反应5h；第五步让温度降至室温，在600r/min的搅拌速度下加入4.6g的三乙胺TEA，反应35min；最后，加入200g的去离子水进行乳化，高速搅拌2h后，静置24h，得到淡蓝色的含N、P阻燃水性聚氨酯。
3.根据权利要求1所述含N、P阻燃水性聚氨酯的制备方法，其特征在于所述缚酸剂为碳酸钾，碳酸钠，三乙胺中的一种。
CN201811524760.7A 2018-12-13 2018-12-13 一种含n、p阻燃水性聚氨酯的制备方法 Active CN109651589B (zh)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN201811524760.7A CN109651589B (zh) 2018-12-13 2018-12-13 一种含n、p阻燃水性聚氨酯的制备方法

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN201811524760.7A CN109651589B (zh) 2018-12-13 2018-12-13 一种含n、p阻燃水性聚氨酯的制备方法

Publications (2)

Publication Number Publication Date
CN109651589A CN109651589A (zh) 2019-04-19
CN109651589B true CN109651589B (zh) 2021-02-09

Family

ID=66113028

Family Applications (1)

Application Number Title Priority Date Filing Date
CN201811524760.7A Active CN109651589B (zh) 2018-12-13 2018-12-13 一种含n、p阻燃水性聚氨酯的制备方法

Country Status (1)

Country Link
CN (1) CN109651589B (zh)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN111574676B (zh) * 2020-05-21 2022-02-08 上海工程技术大学 阻燃水性聚氨酯乳液的制备方法
CN114890960B (zh) * 2022-05-17 2023-09-15 淮阴师范学院 一种羟基改性三聚氰胺的制备方法及其应用

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101735599A (zh) * 2009-12-24 2010-06-16 华南理工大学 一种紫外光固化有机硅改性聚氨酯水分散体及其制备方法
CN103483589A (zh) * 2013-09-16 2014-01-01 上海交通大学 二维聚膦腈纳米片层及其制备和应用方法
CN103992353A (zh) * 2014-05-04 2014-08-20 常州大学 阻燃剂六丁醇基环三磷腈及制备方法和应用
CN104725428A (zh) * 2014-10-12 2015-06-24 青岛科技大学 三聚氰胺改性聚氨基环三磷腈及其制备方法
CN106700019A (zh) * 2016-12-30 2017-05-24 姚东生 一种三聚氰胺改性水性聚氨酯阻燃树脂及其制备方法

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3412045A (en) * 1959-12-24 1968-11-19 Hughes Aircraft Co Plastic reaction products of a phosphonitrilic halide and a polyamine
GB1020254A (en) * 1964-06-29 1966-02-16 Shell Int Research Improvements in or relating to polyurethanes
CN104292504A (zh) * 2014-10-14 2015-01-21 河北大学 一种磷腈阻燃剂及其制备方法和应用
CN108193493A (zh) * 2018-01-23 2018-06-22 天台圣安伦地毯有限公司 一种阻燃地毯的制备方法

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101735599A (zh) * 2009-12-24 2010-06-16 华南理工大学 一种紫外光固化有机硅改性聚氨酯水分散体及其制备方法
CN103483589A (zh) * 2013-09-16 2014-01-01 上海交通大学 二维聚膦腈纳米片层及其制备和应用方法
CN103992353A (zh) * 2014-05-04 2014-08-20 常州大学 阻燃剂六丁醇基环三磷腈及制备方法和应用
CN104725428A (zh) * 2014-10-12 2015-06-24 青岛科技大学 三聚氰胺改性聚氨基环三磷腈及其制备方法
CN106700019A (zh) * 2016-12-30 2017-05-24 姚东生 一种三聚氰胺改性水性聚氨酯阻燃树脂及其制备方法

Also Published As

Publication number Publication date
CN109651589A (zh) 2019-04-19

Similar Documents

Publication Publication Date Title
CN105061711B (zh) 一种端基为环氧基的dopo型反应型阻燃剂及其制备方法和应用
CN111072973B (zh) 一种含磷poss及其制备方法以及在阻燃剂中的应用
CN103030770B (zh) 一种环保阻燃型聚氨酯乳液及其制备方法
CN109651589B (zh) 一种含n、p阻燃水性聚氨酯的制备方法
KR101068691B1 (ko) 셀룰로오즈 포스파이트 화합물의 제조방법
CN106432740B (zh) 一种含羟基聚膦酸酯阻燃剂及其制备方法和应用
CN105542160A (zh) 单组份磷-氮双环笼状大分子膨胀型阻燃剂及其制备方法和应用
CN111574676B (zh) 阻燃水性聚氨酯乳液的制备方法
CN103130977A (zh) 一种双组分水性木器漆的聚氨酯多元醇分散体及其制备方法
CN112225865A (zh) 一种疏水阻燃型水性聚氨酯及其制备方法
CN104558683A (zh) 一种含双dopo的环状磷酸酯阻燃剂，制备方法及其应用
CN113354680A (zh) 一种生物基反应型阻燃剂、阻燃水性聚氨酯乳液及制备方法
CN109251293B (zh) 一种含呋喃环侧基的三嗪类聚氨酯成炭剂及其合成方法
CN105238245A (zh) 一种环氧树脂改性的水性聚氨酯阻燃涂料及其制备方法
CN114605906B (zh) 一种含磷硅透明阻燃涂层的制备方法
CN110563944A (zh) 一种聚磷腈共价三嗪聚合物及其制备方法和应用
CN118271938A (zh) 一种基于线性聚磷腈的可光固化阻燃透明涂料的制备方法及其在木制品中的应用
CN116554823B (zh) 一种耐水聚氨酯胶粘剂及其制备方法
CN110862508B (zh) 三嗪基含氟扩链剂改性聚氨酯乳液的制备方法
CN113337004A (zh) 一种新型磷氮dopo衍生物阻燃剂及其合成方法和应用
CN102942586A (zh) 2-甲基丙烯酸乙酯基苯甲基磷酸酯的制备方法
CN113214656B (zh) 一种以八环糊精poss为炭源的膨胀型阻燃剂及其应用
CN111763232B (zh) 一种含有反应基团的磷杂菲/次磷酸盐双基阻燃剂及其制备方法
JP6538578B2 (ja) 難燃性ポリヒドロキシウレタン樹脂及び難燃性被膜
CN113735905A (zh) 一种含有笼状膦酸酯胺有机硅化合物阻燃成炭剂及其制备方法与应用

Legal Events

Date Code Title Description
PB01 Publication
PB01 Publication
SE01 Entry into force of request for substantive examination
SE01 Entry into force of request for substantive examination
GR01 Patent grant
GR01 Patent grant