Phosphorus-containing water-soluble flame retardant and preparation method thereof

A flame retardant, water-soluble technology, applied in the field of water-soluble flame retardants and their preparation, can solve the problems of affecting the stress transfer between the interface and the units on both sides, the large amount of additive flame retardants, poor mechanical properties and durability, etc. Achieve the effect of avoiding the problem of migration and precipitation, simple preparation method and excellent flame retardant performance

Pending Publication Date: 2021-11-12
THE UNIV OF NOTTINGHAM NINGBO CHINA +1
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Problems solved by technology

At present, phosphorus-based flame retardants are mainly additive types. Compounds such as red phosphorus, phosphoric acid esters, and ammonium phosphates can be used as additive-type flame retardants in epoxy resin systems, but the amount of additive-type flame retardants is large. The flame retardant effect is greatly affected by the dispersion, and it is easy to migrate and precipitate from the matrix material during use, which affects the flame retardant effect and the overall performance of the material
[0006] Due to the non-hydrophilic nature of epoxy resin, the interface compatibility of the composite material is poor, which affects the stress transfer between the interface and the units on both sides, resulting in poor mechanical properties and durability of the product, causing the material to be easily separated under load. Layers and fractures limit the further development and application of such materials (such as: Wang Ge, Gu Shaohua, Zhang Wenfu, Wang Cuicui, etc. Research progress on interface modification of plant fiber reinforced epoxy resin composites[J]. Journal of Central South University of Forestry and Technology, 2020,40(07):144-152)

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  • Phosphorus-containing water-soluble flame retardant and preparation method thereof
  • Phosphorus-containing water-soluble flame retardant and preparation method thereof
  • Phosphorus-containing water-soluble flame retardant and preparation method thereof

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preparation example Construction

[0052] Another aspect of the embodiments of the present invention provides a method for preparing a phosphorus-containing water-soluble flame retardant, which includes:

[0053] Polyethyleneimine (PEI) shown in the general formula (II) structure, the monovalent aldehyde compound shown in the general formula (III) structure and the phosphoric acid ester compound shown in the general formula (IV) structure are mixed and reacted to prepare Obtain described water-soluble flame retardant, described compound has general formula (I) structure:

[0054] in:

[0055]

[0056] in:

[0057] R 1 selected from hydrogen, substituted or unsubstituted C 1 -C 20 Alkyl, substituted or unsubstituted C 2 -C 20 Alkenyl, substituted or unsubstituted C 6 -C 20 Aryl, substituted or unsubstituted C 2 -C 20 Heteroaryl, substituted or unsubstituted C 4 -C 20 Carbocyclyl, substituted or unsubstituted C 2 -C 20 Heterocyclyl, or C 3 -C 8 Cycloalkyl;

[0058] R 2 selected from

[0...

Embodiment 1

[0090] (1) Preparation of water-soluble flame retardant: 100 molar parts of polyethyleneimine, 26 molar parts of vanillin, 26 molar parts of 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxidized The mixture of dopo (DOPO) was dissolved in methanol, and the system was reacted at 120°C for 12 hours to obtain a water-soluble flame retardant (FR-1), whose structural formula is as follows:

[0091]

[0092] After testing, the proton nuclear magnetic resonance spectrum is as follows:

[0093] 1 H NMR (500MHz, Methanol-d 4 )δ7.99(d, J=6.6Hz, 1H), 7.67(s, 1H), 7.49 (d, J=0.9Hz, 1H), 7.38(s, 1H), 6.96(d, J=0.8Hz, 1H), 3.82(s,3H), 3.05(s,1H), 2.88–2.59(m,19H), 1.74–1.64(m,2H), 1.44(s,1H), indicating that FR-1 was synthesized.

[0094] (2) Preparation of flame-retardant plant fiber reinforced epoxy resin composite material: 12 parts by mass of FR-1 was dissolved in water to prepare a flame retardant solution, and 100 parts by mass of ramie fabric was soaked in the flame retardant a...

Embodiment 2

[0099] (1) Preparation of water-soluble flame retardant: 100 molar parts of polyethyleneimine, 20 molar parts of n-butyraldehyde, 20 molar parts of 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10- A mixture of oxides (DOPO) was dissolved in ethanol, and the system was reacted at 100°C for 8 hours to obtain a water-soluble flame retardant (FR-2), whose structural formula is as follows:

[0100]

[0101] After testing, the proton nuclear magnetic resonance spectrum is as follows:

[0102] 1 H NMR (500MHz, Methanol-d 4 )δ8.02–7.97(m,2H),7.93(s,1H),7.59(s,1H),7.49(d,J=0.8Hz,2H),7.38(d,J=2.0Hz,2H), 3.77(d,J=6.0Hz,1H),3.71(d,J=10.0Hz,1H),3.11(s,0H),3.05(s,1H),2.96(s,1H),2.86(s,1H ),2.83–2.74 (m,7H),2.75(dd,J=2.6,1.3Hz,3H),2.74–2.69(m,6H),2.72–2.63(m,7H),2.65–2.59(m,3H ), 2.51(d, J=2.3Hz, 1H), 1.84(d, J=7.4Hz, 2H), 1.76(d, J=5.1Hz, 2H), 1.71–1.64(m, 3H), 1.44(d , J=0.7Hz, 1H), 1.38(d, J=9.4Hz, 2H), 0.93(s, 4H), indicating that FR-2 was synthesized.

[0103] (2) Preparation of f...

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Abstract

The invention discloses a phosphorus-containing water-soluble flame retardant and a preparation method thereof. The phosphorus-containing water-soluble flame retardant has a structure as shown in a general formula (I) in the specification. The phosphorus-containing water-soluble flame retardant has higher nitrogen element and phosphorus element contents, has excellent flame retardant property, and can realize a halogen-free flame retardant effect. Compared with a common flame retardant, the compound disclosed by the invention can be used as a reaction type epoxy resin co-curing agent due to the amido group, and can play a cross-linking curing role in epoxy resin. Meanwhile, the water-soluble flame retardant can be infiltrated in the plant fiber reinforced material to the greatest extent, so that the water-soluble flame retardant disclosed by the invention can solve the interface problem of the plant fiber reinforced epoxy resin composite material to the greatest extent, and the interlaminar shear strength is at least improved by 58.5% or above.

Description

technical field [0001] The invention belongs to the field of materials, and in particular relates to a phosphorus-containing water-soluble flame retardant and a preparation method thereof. Background technique [0002] Plant fiber reinforced composite materials have become one of the research hotspots in the field of composite materials. Natural plant fiber reinforcement has excellent characteristics such as low price, light weight, high specific strength and specific stiffness, and can be naturally degraded. It is an important reinforcement for the preparation of environmentally friendly green composite materials. Material. [0003] Epoxy resin is one of the commonly used composite matrix materials in composite materials. Its molecular structure usually contains two or more epoxy groups, which are mainly formed by the reaction of epichlorohydrin with alcohols or phenols. have to. The highly reactive epoxy groups in epoxy resin allow it to react with a variety of active hy...

Claims

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Application Information

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IPC IPC(8): C08G73/02D06M15/61C08J5/06C08L63/00C08L1/02D06M101/06
CPCC08G73/0206D06M15/61C08J5/06C08J2363/00C08J2301/02D06M2101/06D06M2200/30
Inventor 益小苏张力月孟润生肖勇民汪泽湘
Owner THE UNIV OF NOTTINGHAM NINGBO CHINA
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