CN104211966A - Method for preparing phosphorus-containing fire-retardant silicone oil - Google Patents
Method for preparing phosphorus-containing fire-retardant silicone oil Download PDFInfo
- Publication number
- CN104211966A CN104211966A CN201410470957.2A CN201410470957A CN104211966A CN 104211966 A CN104211966 A CN 104211966A CN 201410470957 A CN201410470957 A CN 201410470957A CN 104211966 A CN104211966 A CN 104211966A
- Authority
- CN
- China
- Prior art keywords
- silicone oil
- phosphorus
- molar amount
- add
- retardant silicone
- 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.)
- Granted
Links
- 239000003063 flame retardant Substances 0.000 title claims abstract description 35
- 229920002545 silicone oil Polymers 0.000 title claims abstract description 29
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 title claims abstract description 19
- 229910052698 phosphorus Inorganic materials 0.000 title claims abstract description 19
- 239000011574 phosphorus Substances 0.000 title claims abstract description 19
- 238000000034 method Methods 0.000 title abstract description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 16
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims abstract description 14
- 238000006243 chemical reaction Methods 0.000 claims abstract description 13
- 238000003756 stirring Methods 0.000 claims abstract description 12
- 238000010438 heat treatment Methods 0.000 claims abstract description 11
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims abstract description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 7
- 239000001257 hydrogen Substances 0.000 claims abstract description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 7
- 238000002360 preparation method Methods 0.000 claims abstract description 6
- 230000001681 protective effect Effects 0.000 claims abstract description 6
- 239000007789 gas Substances 0.000 claims abstract description 5
- 239000007788 liquid Substances 0.000 claims abstract description 5
- LGQLOGILCSXPEA-UHFFFAOYSA-L nickel sulfate Chemical compound [Ni+2].[O-]S([O-])(=O)=O LGQLOGILCSXPEA-UHFFFAOYSA-L 0.000 claims abstract description 5
- 229910000363 nickel(II) sulfate Inorganic materials 0.000 claims abstract description 5
- 239000000203 mixture Substances 0.000 claims abstract description 3
- 150000003017 phosphorus Chemical class 0.000 claims abstract 2
- 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 32
- 239000003054 catalyst Substances 0.000 claims description 4
- KZTMRRGWEOKICD-UHFFFAOYSA-N hydroxymethoxy-n-propanoylphosphonamidic acid Chemical compound CCC(=O)NP(O)(=O)OCO KZTMRRGWEOKICD-UHFFFAOYSA-N 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 2
- 229920000742 Cotton Polymers 0.000 abstract description 18
- 239000004744 fabric Substances 0.000 abstract description 17
- 239000000463 material Substances 0.000 abstract description 6
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 abstract description 5
- 229910052710 silicon Inorganic materials 0.000 abstract description 5
- 239000010703 silicon Substances 0.000 abstract description 5
- 239000000675 fabric finishing Substances 0.000 abstract description 4
- 238000009962 finishing (textile) Methods 0.000 abstract description 4
- 239000008204 material by function Substances 0.000 abstract description 3
- 239000012752 auxiliary agent Substances 0.000 abstract 2
- ANLZTHUPELWALK-UHFFFAOYSA-N [hydroxymethyl(propanoyl)amino]phosphonic acid Chemical compound C(CC)(=O)N(CO)P(=O)(O)O ANLZTHUPELWALK-UHFFFAOYSA-N 0.000 abstract 1
- 238000009833 condensation Methods 0.000 abstract 1
- 230000005494 condensation Effects 0.000 abstract 1
- 238000001704 evaporation Methods 0.000 abstract 1
- 238000001914 filtration Methods 0.000 abstract 1
- 239000003921 oil Substances 0.000 abstract 1
- 239000010902 straw Substances 0.000 abstract 1
- 238000001291 vacuum drying Methods 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 10
- 239000001301 oxygen Substances 0.000 description 10
- 229910052760 oxygen Inorganic materials 0.000 description 10
- 239000012153 distilled water Substances 0.000 description 4
- 239000004753 textile Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 239000000126 substance Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000000498 cooling water Substances 0.000 description 2
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 238000007598 dipping method Methods 0.000 description 2
- 238000004043 dyeing Methods 0.000 description 2
- 238000007730 finishing process Methods 0.000 description 2
- CMOAHYOGLLEOGO-UHFFFAOYSA-N oxozirconium;dihydrochloride Chemical compound Cl.Cl.[Zr]=O CMOAHYOGLLEOGO-UHFFFAOYSA-N 0.000 description 2
- 238000011056 performance test Methods 0.000 description 2
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 2
- 229920001296 polysiloxane Polymers 0.000 description 2
- 238000003825 pressing Methods 0.000 description 2
- 238000005096 rolling process Methods 0.000 description 2
- 238000002791 soaking Methods 0.000 description 2
- 238000010276 construction Methods 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 229920001002 functional polymer Polymers 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000005871 repellent Substances 0.000 description 1
- 229920005573 silicon-containing polymer Polymers 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
Landscapes
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Fireproofing Substances (AREA)
Abstract
Description
技术领域 technical field
本发明涉及一种新型含磷阻燃性硅油的制备方法,属于有机硅阻燃剂制备技术领域和新型印染助剂技术领域，可应用于棉织物整理，赋予其阻燃性。 The invention relates to a preparation method of a novel phosphorus-containing flame retardant silicone oil, which belongs to the technical field of organosilicon flame retardant preparation and novel printing and dyeing auxiliaries, and can be applied to cotton fabric finishing to endow it with flame retardancy.
背景技术 Background technique
有机硅聚合物作为一种功能性高分子材料，由于其独特的结构和性能，已经成为建筑、纺织、汽车、日化等行业必需的材料之一。因此，对有机硅及其衍生物的研究正在不断深入，有机硅的应用领域也在不断拓展，逐渐形成了一类重要的化工产品体系。硅油分为甲基有机硅油和改性有机硅油。甲基有机硅油为二甲基硅油，其分子结构中不含活性基团，限制了其在化工产品中的应用；改性有机硅油是二甲基硅油分子中的部分甲基被各种有机基团取代后得到的特种硅油，活性基团或功能基团的引入，赋予了硅油新的特性，拓展了其在各个领域的应用。在纺织印染行业，其分子结构决定了有机硅分子的柔性和弹性，通常被用作织物的拒水整理剂、柔软剂等。有机硅阻燃剂是一种生态友好、高效抑烟型阻燃剂，其能够赋予材料优异的阻燃性能，如低燃速、低释热和防滴落等，在一些材料的阻燃研究中得到应用。硅元素和磷元素有很好的阻燃协同作用，因此，若将有机硅进行改性，在有机硅分子中引入阻燃元素磷，可以制备出具有高效阻燃性能的含磷有机硅阻燃剂。经检索，目前国内外专利和文献尚未报道本发明涉及的新型含磷阻燃性硅油，而此新型硅油在工业上特别是棉织物整理方面具有广泛的应用价值和前景。 As a functional polymer material, silicone polymer has become one of the necessary materials in construction, textile, automobile, daily chemical and other industries due to its unique structure and performance. Therefore, the research on organosilicon and its derivatives is deepening, and the application field of organosilicon is also expanding, gradually forming an important chemical product system. Silicone oil is divided into methyl silicone oil and modified silicone oil. Methyl silicone oil is dimethyl silicone oil, and its molecular structure does not contain active groups, which limits its application in chemical products; modified silicone oil is part of the methyl group in the dimethyl silicone oil molecule replaced by various organic groups. The introduction of active groups or functional groups endows silicone oil with new characteristics and expands its application in various fields. In the textile printing and dyeing industry, its molecular structure determines the flexibility and elasticity of silicone molecules, and it is usually used as a water-repellent finishing agent and softener for fabrics. Silicone flame retardant is an eco-friendly, high-efficiency smoke-suppressing flame retardant, which can endow materials with excellent flame-retardant properties, such as low burning rate, low heat release and anti-dripping, etc. It is used in the flame-retardant research of some materials be applied in. Silicon and phosphorus elements have a good flame retardant synergistic effect. Therefore, if the organic silicon is modified and the flame retardant element phosphorus is introduced into the organic silicon molecule, a phosphorus-containing organic silicon flame retardant with high flame retardant performance can be prepared. agent. After retrieval, the novel phosphorus-containing flame-retardant silicone oil involved in the present invention has not been reported in domestic and foreign patents and literatures at present, and this novel silicone oil has wide application value and prospect in industry, especially in cotton fabric finishing.
发明内容 Contents of the invention
本发明的目的在于制备一种含磷阻燃性硅油，可应用于棉织物整理或制备功能材料的助剂，赋予棉织物或功能材料良好的阻燃性，其合成方法简单，原料易得，应用方便；制备的含磷阻燃性硅油具有下列分子结构： The object of the present invention is to prepare a kind of phosphorus-containing flame-retardant silicone oil, which can be applied to cotton fabric finishing or preparation of functional materials, and endows cotton fabrics or functional materials with good flame retardancy. The synthesis method is simple and the raw materials are easy to obtain. Easy to use; the prepared phosphorus-containing flame-retardant silicone oil has the following molecular structure:
本发明的含磷阻燃性硅油的制备方法，按如下步骤操作： The preparation method of the phosphorus-containing flame-retardant silicone oil of the present invention operates as follows:
将装有冷凝管、温度计、滴液漏斗的四口烧瓶反应装置固定在恒温加热磁力搅拌器中，在氮气保护环境中，加入0.05倍摩尔量的催化剂硫酸镍，10～12倍摩尔量的溶剂正己烷和1～1.2倍摩尔量的N-羟甲基膦酰基丙酰胺，并在室温下搅拌均匀，然后将含1倍摩尔量活性氢的含氢硅油滴加到混合物中，打开恒温加热磁力搅拌器加热，通入氮气作为保护气体，在100℃下反应10～12h；反应完成后，加入2～3倍摩尔量的甲苯，搅拌均匀后，所得溶液经过滤、旋转蒸发再真空干燥得淡黄色粘稠液体，其化学反应如下： Fix the four-necked flask reaction device equipped with a condenser, a thermometer, and a dropping funnel in a constant temperature heating magnetic stirrer, and in a nitrogen protection environment, add 0.05 times the molar amount of catalyst nickel sulfate, and 10 to 12 times the molar amount of the solvent n-Hexane and 1 to 1.2 times the molar amount of N-hydroxymethylphosphonopropionamide, and stir evenly at room temperature, then add hydrogen-containing silicone oil containing 1 times the molar amount of active hydrogen to the mixture, and turn on the constant temperature heating magnetic force Heat with a stirrer, feed nitrogen as a protective gas, and react at 100°C for 10-12 hours; after the reaction is completed, add 2-3 times the molar amount of toluene, stir evenly, and filter the obtained solution, rotary evaporate and vacuum-dry to obtain a thin Yellow viscous liquid, its chemical reaction is as follows:
目标产物即为含磷阻燃性硅油。 The target product is phosphorus-containing flame-retardant silicone oil.
具体实施方式： Detailed ways:
实施例1： Example 1:
（1）将装有冷凝管、温度计、滴液漏斗的一只250mL四口烧瓶反应装置固定在恒温加热磁力搅拌器中，在氮气保护环境中，加入0.8g(0.005mol)催化剂硫酸镍和130mL(1mol)正己烷，再加入21.1g (0.1mol)N-羟甲基膦酰基丙酰胺，室温下搅拌均匀，然后将16.9g(0.1mol)含氢硅油加入滴液漏斗中，打开恒温加热磁力搅拌器加热，通入氮气作为保护气体，在100℃下反应10h；反应完成后，加入41.6mL(0.3mol)甲苯，搅拌均匀后，所得溶液经过滤、旋转蒸发再真空干燥得淡黄色粘稠液体，即为含磷的阻燃性硅油，产率为75.21%。 (1) Fix a 250mL four-neck flask reaction device equipped with a condenser, a thermometer and a dropping funnel in a constant temperature heating magnetic stirrer, and add 0.8g (0.005mol) of catalyst nickel sulfate and 130mL of (1mol) n-hexane, then add 21.1g (0.1mol) N-hydroxymethylphosphonopropionamide, stir well at room temperature, then add 16.9g (0.1mol) hydrogen-containing silicone oil into the dropping funnel, turn on the constant temperature heating magnetic Heat the stirrer, feed nitrogen as a protective gas, and react at 100°C for 10 hours; after the reaction is completed, add 41.6mL (0.3mol) toluene, stir evenly, and filter the resulting solution, rotary evaporate and vacuum-dry to obtain a light yellow viscous The liquid is phosphorus-containing flame-retardant silicone oil, and the yield is 75.21%.
（2）根据GB/T5455-1997纺织品阻燃试验极限氧指数法（LOI）测试整理后织物的极限氧指数。 (2) According to GB/T5455-1997 Textile Flame Retardancy Test Limiting Oxygen Index (LOI) method, the limiting oxygen index of the finished fabric is tested.
取1g的氯氧化锆于烧杯中，加入50g的蒸馏水溶解，称取40g合成的含磷阻燃性硅油，加入100g的蒸馏水，搅拌均匀，调节pH为6，配置成整理液。整理工艺如下：剪取15×15cm纯棉布样，室温下用台式气压电动小轧车进行二浸二压，轧余率为85％，每次浸渍时间4分钟，浸轧后将布样在100℃下预烘3 min，然后在170℃下烘焙3min，取出布样冷却水洗，室温晾干。 Take 1g of zirconium oxychloride in a beaker, add 50g of distilled water to dissolve, weigh 40g of synthetic phosphorus-containing flame-retardant silicone oil, add 100g of distilled water, stir well, adjust the pH to 6, and configure it as a finishing solution. The finishing process is as follows: cut a 15×15cm pure cotton cloth sample, carry out two dipping and two pressing at room temperature with a small electric padding machine with a desktop air pressure, and the excess rolling rate is 85%, and the soaking time is 4 minutes each time. Pre-bake at 100°C for 3 minutes, then bake at 170°C for 3 minutes, take out the cloth sample, wash it with cooling water, and dry it at room temperature.
阻燃性能测试： Flame retardant performance test:
根据GB/T5455-1997，极限氧指数(LOI)≥26% 的属于难燃材料。整理后的纯棉试样的LOI≥33%,具有良好的阻燃性能。 According to GB/T5455-1997, the limiting oxygen index (LOI) ≥ 26% is a flame retardant material. The LOI of the finished cotton sample is more than 33%, which has good flame retardancy.
由表中结果可以看出，经新型含磷阻燃性硅油整理的棉织物具有较高的极限氧指数，阻燃性能较未整理棉织物有很大提高。 It can be seen from the results in the table that the cotton fabric treated with the new phosphorus-containing flame-retardant silicone oil has a higher limiting oxygen index, and its flame-retardant performance is greatly improved compared with the untreated cotton fabric.
实施例2： Example 2:
（1）将装有冷凝管、温度计、滴液漏斗的一只250mL四口烧瓶反应装置固定在恒温加热磁力搅拌器中，加入0.8g(0.005mol)催化剂硫酸镍和130mL(1mol)正己烷，再加入25.3g (0.12mol)N-羟甲基膦酰基丙酰胺，室温下搅拌均匀，然后将16.9g(0.1mol)含氢硅油加入滴液漏斗中，打开恒温加热磁力搅拌器加热，通入氮气作为保护气体，在100℃下反应12h。反应完成后，加入41.6mL(0.3mol)甲苯，搅拌均匀后，所得溶液经过滤、旋转蒸发再真空干燥得淡黄色粘稠液体，即为含磷的阻燃性硅油，产率为76.43%。 (1) Fix a 250mL four-neck flask reaction device equipped with a condenser, a thermometer, and a dropping funnel in a constant temperature heating magnetic stirrer, add 0.8g (0.005mol) of catalyst nickel sulfate and 130mL (1mol) of n-hexane, Then add 25.3g (0.12mol) of N-hydroxymethylphosphonopropionamide, stir well at room temperature, then add 16.9g (0.1mol) of hydrogen-containing silicone oil into the dropping funnel, turn on the constant temperature heating magnetic stirrer to heat, and pass in Nitrogen was used as a protective gas, and the reaction was carried out at 100°C for 12h. After the reaction was completed, 41.6 mL (0.3 mol) of toluene was added, and after stirring evenly, the resulting solution was filtered, rotary evaporated, and then vacuum-dried to obtain a light yellow viscous liquid, which was phosphorus-containing flame-retardant silicone oil, with a yield of 76.43%.
（2）根据GB/T5455-1997纺织品阻燃试验极限氧指数法（LOI）测试整理后织物的极限氧指数。 (2) According to GB/T5455-1997 Textile Flame Retardancy Test Limiting Oxygen Index (LOI) method, the limiting oxygen index of the finished fabric is tested.
取1g的氯氧化锆于烧杯中，加入50g的蒸馏水溶解，称取40g合成的含磷阻燃性硅油，加入100g的蒸馏水，搅拌均匀，调节pH为6，配置成整理液。整理工艺如下：剪取15×15cm纯棉布样，室温下用台式气压电动小轧车进行二浸二压，轧余率为85％，每次浸渍时间4分钟，浸轧后将布样在100℃下预烘3 min，然后在170℃下烘焙3min，取出布样冷却水洗，室温晾干。 Take 1g of zirconium oxychloride in a beaker, add 50g of distilled water to dissolve, weigh 40g of synthetic phosphorus-containing flame-retardant silicone oil, add 100g of distilled water, stir well, adjust the pH to 6, and configure it as a finishing solution. The finishing process is as follows: cut a 15×15cm pure cotton cloth sample, carry out two dipping and two pressing at room temperature with a small electric padding machine with a desktop air pressure, and the excess rolling rate is 85%, and the soaking time is 4 minutes each time. Pre-bake at 100°C for 3 minutes, then bake at 170°C for 3 minutes, take out the cloth sample, wash it with cooling water, and dry it at room temperature.
阻燃性能测试： Flame retardant performance test:
根据GB/T5455-1997，极限氧指数(LOI)≥26% 的属于难燃材料。整理后的纯棉试样的LOI≥33%,具有良好的阻燃性能。 According to GB/T5455-1997, the limiting oxygen index (LOI) ≥ 26% is a flame retardant material. The LOI of the finished cotton sample is more than 33%, which has good flame retardancy.
由表中结果可以看出，经含磷阻燃性硅油整理的棉织物具有较高的极限氧指数，阻燃性能较未整理棉织物有很大提高，含磷阻燃性硅油具有良好的阻燃性能。 It can be seen from the results in the table that the cotton fabric treated with phosphorus-containing flame-retardant silicone oil has a higher limiting oxygen index, and its flame-retardant performance is greatly improved compared with that of untreated cotton fabric. Phosphorus-containing flame-retardant silicone oil has good flammability.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201410470957.2A CN104211966B (en) | 2014-09-16 | 2014-09-16 | A kind of preparation method of phosphor-containing flame-proof silicone oil |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201410470957.2A CN104211966B (en) | 2014-09-16 | 2014-09-16 | A kind of preparation method of phosphor-containing flame-proof silicone oil |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN104211966A true CN104211966A (en) | 2014-12-17 |
| CN104211966B CN104211966B (en) | 2016-09-28 |
Family
ID=52093895
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201410470957.2A Active CN104211966B (en) | 2014-09-16 | 2014-09-16 | A kind of preparation method of phosphor-containing flame-proof silicone oil |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN104211966B (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106700920A (en) * | 2017-01-22 | 2017-05-24 | 太原理工大学 | Reaction type polysiloxane flame-retardant coating and preparation method thereof |
| CN109293923A (en) * | 2018-09-26 | 2019-02-01 | 黄山市强力化工有限公司 | A kind of flame-retardant modified silicone oil, preparation method and application thereof |
| CN109943077A (en) * | 2019-03-13 | 2019-06-28 | 长沙集智创新工业设计有限公司 | A kind of preparation process of modified silica-gel sealing ring |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2995594A (en) * | 1958-12-23 | 1961-08-08 | Union Carbide Corp | Process for making phosphorus-containing silicon compounds |
| JPH07216091A (en) * | 1994-01-27 | 1995-08-15 | Toray Dow Corning Silicone Co Ltd | Method for producing siloxanyl-phosphate |
| CN102408570A (en) * | 2011-10-12 | 2012-04-11 | 青岛大学 | Preparation method of novel organic silicone oil water repellent agent used for cotton fabric |
| CN102504264A (en) * | 2011-10-08 | 2012-06-20 | 青岛大学 | Preparation method of flame retarding antibacterial agent |
| CN103265577A (en) * | 2013-05-20 | 2013-08-28 | 青岛大学 | Preparation method of novel flame retardant for cotton |
-
2014
- 2014-09-16 CN CN201410470957.2A patent/CN104211966B/en active Active
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2995594A (en) * | 1958-12-23 | 1961-08-08 | Union Carbide Corp | Process for making phosphorus-containing silicon compounds |
| JPH07216091A (en) * | 1994-01-27 | 1995-08-15 | Toray Dow Corning Silicone Co Ltd | Method for producing siloxanyl-phosphate |
| CN102504264A (en) * | 2011-10-08 | 2012-06-20 | 青岛大学 | Preparation method of flame retarding antibacterial agent |
| CN102408570A (en) * | 2011-10-12 | 2012-04-11 | 青岛大学 | Preparation method of novel organic silicone oil water repellent agent used for cotton fabric |
| CN103265577A (en) * | 2013-05-20 | 2013-08-28 | 青岛大学 | Preparation method of novel flame retardant for cotton |
Non-Patent Citations (5)
| Title |
|---|
| E. LECOEUR.，ET AL.: ""Optimization of monoguanidine dihydrogen phosphate and amino"", 《POLYMER DEGRADATION AND STABILITY》 * |
| JUHUA YE, ET AL.: ""Novel phosphorus-containing hyperbranched polysiloxane and its high"", 《POLYMER DEGRADATION AND STABLITY》 * |
| 丁洋，等: ""阻燃型磷酸酯聚硅氧烷的合成与应用"", 《精细化工》 * |
| 周惠祥，等: ""AFLAMMITKWB在全棉耐久阻燃加工中的应用"", 《印染》 * |
| 董朝红，等: ""反应型含磷氮元素的聚硅氧烷的制备及其对棉织物拒水阻燃性能"", 《功能材料》 * |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106700920A (en) * | 2017-01-22 | 2017-05-24 | 太原理工大学 | Reaction type polysiloxane flame-retardant coating and preparation method thereof |
| CN106700920B (en) * | 2017-01-22 | 2019-05-17 | 太原理工大学 | A kind of response type polysiloxanes flame retardant coating and preparation method thereof |
| CN109293923A (en) * | 2018-09-26 | 2019-02-01 | 黄山市强力化工有限公司 | A kind of flame-retardant modified silicone oil, preparation method and application thereof |
| CN109943077A (en) * | 2019-03-13 | 2019-06-28 | 长沙集智创新工业设计有限公司 | A kind of preparation process of modified silica-gel sealing ring |
Also Published As
| Publication number | Publication date |
|---|---|
| CN104211966B (en) | 2016-09-28 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Liu et al. | Durable flame retardant cellulosic fibers modified with novel, facile and efficient phytic acid-based finishing agent | |
| Liu et al. | A novel durable flame retardant cotton fabric produced by surface chemical grafting of phosphorus-and nitrogen-containing compounds | |
| CN106700081B (en) | Polysiloxane flame retardant containing nitrogen, phosphorus and silicon and preparation method thereof | |
| CN105348326B (en) | A kind of N P fire proofings and preparation method thereof and the application in textile | |
| Wang et al. | Properties of flame-retardant cotton fabrics: Combustion behavior, thermal stability and mechanism of Si/P/N synergistic effect | |
| CN105178006B (en) | A kind of reactive flame retardant of phosphorus-nitrogen containing silicon and preparation method and application | |
| CN103881134B (en) | DOPO (9,10-dihydID-9-oxa-10-phosphaphenanthrene-10-oxide)-derived phosphorus-nitrogen flame retardant as well as preparation method and application thereof | |
| CN104211966B (en) | A kind of preparation method of phosphor-containing flame-proof silicone oil | |
| Wang et al. | Influence of hydroxyl-terminated phosphoramidates on the flame retardancy of microfiber synthetic leather | |
| Sun et al. | Preparation of a novel flame retardant containing triazine groups and its application on cotton fabrics | |
| CN104911910A (en) | Preparation method of cellulose fabric having antibacterial and inflaming-retarding functions | |
| Zhang et al. | Synthetic novel, convenient and eco-friendly Si/P/N synergistic treatment agent to improve the flame retardancy and thermal stability of cotton fabrics | |
| CN103788378A (en) | Polyphosphamide fire retardant with bicyclic phosphate structure and preparation method thereof | |
| Shan et al. | A novel DDPSi-FR flame retardant treatment and its effects on the properties of wool fabrics | |
| CN102011309B (en) | Multifunctional flame retardant as well as preparation and application thereof | |
| Lv et al. | Synthesis of a melamine‐cyclotriphosphazene derivative and its application as flame retardant on cotton gauze | |
| CN101457475B (en) | Method for preparing melamine phosphonate flame-retardant-anti-crease integrated dressing agent for cotton | |
| Su et al. | Fabricating of flame retardant and antibacterial lyocell fabric based on thiamine pyrophosphate modification | |
| WO2007032277A1 (en) | Phosphorus compound, use thereof and flame-retardant polyester fiber | |
| Zuo et al. | Construction of PAN composite fibers with flame retardant, smoke suppression and enhanced mechanical properties based on self-assembled supramolecular network | |
| Choe et al. | Preparation and characterization of durable flame retardant cotton fabrics using phosphorylation reaction of cellulose with ammonium etidronate | |
| WO2009153034A1 (en) | Phosphoramidate flame retardants | |
| CN102504264A (en) | Preparation method of flame retarding antibacterial agent | |
| Wang et al. | Synthesis of a phosphoramidate flame retardant and its flame retardancy on cotton fabrics | |
| CN104926882B (en) | A kind of fire retardant based on three phosphonitrile of naphthylamines basic ring and preparation method thereof |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant | ||
| TR01 | Transfer of patent right |
Effective date of registration: 20171226 Address after: Wujiang District of Suzhou City, Jiangsu province Shengze town 215228 Nanhuan Patentee after: Jinlun (Suzhou) Weaving Co. Ltd. Address before: 266071 Shandong city of Qingdao province Ningxia City Road No. 308 Patentee before: Qingdao University |
|
| TR01 | Transfer of patent right |