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Phosphorus-nitrogen-containing flame retardant with hydroxyl group as well as preparation method and application of flame retardant

A flame retardant, hydroxyl technology, applied in the field of phosphorus nitrogen-containing flame retardants and their preparation, can solve the problems of small molecule precipitation and poor compatibility

Pending Publication Date: 2021-03-05
GUANGDONG GUANGSHAN NEW MATERIALS CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although additive flame retardants have the advantage of being easy to use, and phosphorus-based flame retardants can be used with nitrogen-based flame retardants, additive flame retardants are poorly compatible with resins, and there will be a small amount of corrosion over time. Molecular precipitation phenomenon, and some additive flame retardants are easily soluble in water, therefore, additive flame retardants cannot achieve true environmental protection and flame retardancy

Method used

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  • Phosphorus-nitrogen-containing flame retardant with hydroxyl group as well as preparation method and application of flame retardant
  • Phosphorus-nitrogen-containing flame retardant with hydroxyl group as well as preparation method and application of flame retardant
  • Phosphorus-nitrogen-containing flame retardant with hydroxyl group as well as preparation method and application of flame retardant

Examples

Experimental program
Comparison scheme
Effect test

preparation example 1

[0070] A phosphorus and nitrogen-containing flame retardant with hydroxyl, the structure is as follows:

[0071]

[0072] The preparation method is as follows:

[0073] Put 1mol diethanolamine, 1mol hydroxymethyl dimethyl phosphite, 500mL ethanol, 0.1mol sodium hydroxide and 0.1g DMAP into a three-port 2000mL glass reactor with a stirring device, heat up to ethanol reflux, and react for 24 hours under stirring. After the completion, wash with water until neutral, and remove impurities to obtain the phosphorus-nitrogen-containing flame retardant with the above structure.

[0074] 1 H NMR (400MHz, DMSO-d6): δ=4.26-4.28(t,2H,-OH),3.63-3.66(m,4H,-N-CH 2 -C H 2 -OH),3.47-3.49(d,6H,-P-O-CH 3 ),2.82-2.84(d,2H,-P-C H 2 -)2.53-2.55(t,4H,-N-C H 2 -CH 2 -OH).

preparation example 2

[0076] A phosphorus and nitrogen-containing flame retardant with hydroxyl, the structure is as follows:

[0077]

[0078] The preparation method is as follows:

[0079] Put 1mol 2,2-bis(4-hydroxy-3-aminophenyl)propane, 2.1mol trimethyl phosphate, 200mL DMF, 0.1mol sodium hydroxide and 0.1g DMAP into a three-port 500mL glass reactor with stirring device , heated to ethanol reflux, reacted for 24 hours under stirring, washed with water until neutral after the reaction, and removed impurities to obtain the phosphorus-nitrogen-containing flame retardant with the above structure.

[0080] 1 H NMR (400MHz, DMSO-d6): δ=9.77-9.80(s,2H,-OH),6.51-6.60(dd,6H,ph-H),4.38-4.42(s,2H,-NH-), 3.80-3.84(d,12H,-P-O-CH 3 ),1.65-1.72(s,6H,-CH 3 ).

preparation example 3

[0082] A phosphorus and nitrogen-containing flame retardant with hydroxyl, the structure is as follows:

[0083]

[0084] The preparation method is as follows:

[0085] Put 1mol 4-(2-hydroxyethylamino)phenol, 2.1mol trimethyl phosphate, 200mL DMF, 0.1mol sodium hydroxide and 0.1g DMAP into a three-port 500mL glass reactor with stirring device, heat up to ethanol reflux, React under stirring for 24 hours, wash with water until neutral after the reaction, and remove impurities to obtain the phosphorus-nitrogen-containing flame retardant with the above structure.

[0086] 1 H NMR (400MHz, DMSO-d6): δ=9.39-9.41 (s, 1H, ph-OH), 6.72-6.64 (m, 2H, ph-H close to -OH), 6.50-6.42 (m, 2H ,ph-H),4.64-4.68(t,1H,-OH),3.76-3.80(d,6H,-P-O-CH 3 ),3.55-3.60(m,2H,-CH 2 -OH),3.24-3.27(t,2H,-N-CH 2 -).

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Abstract

The invention provides a phosphorus-nitrogen-containing flame retardant with a hydroxyl group as well as a preparation method and application of the flame retardant. The phosphorus-nitrogen-containingflame retardant has a structure as shown in a formula I. Molecular chains of the flame retardant provided by the invention have both phosphorus element and nitrogen element, and the phosphorus and nitrogen elements have a synergistic flame retardant effect, so that the flame retardant effect of the flame retardant provided by the invention can be improved. Meanwhile, the flame retardant with a hydroxyl group can be used as a reaction monomer or a chain extender to participate in the reaction, and finally, phosphorus-nitrogen-containing groups can exist in a reaction system in the form of chemical bonds, namely, the phosphorus-nitrogen-containing flame retardant provided by the invention can realize permanent flame retardance.

Description

technical field [0001] The invention belongs to the technical field of flame retardants, and relates to a phosphorus-nitrogen-containing flame retardant with hydroxyl groups, a preparation method and application thereof. Background technique [0002] Flame retardants are functional additives that impart flame retardancy to flammable polymers; they are divided into additive flame retardants and reactive flame retardants according to the application method. According to the composition, additive flame retardants mainly include inorganic flame retardants, halogen flame retardants (organic chlorides and organic bromides), phosphorus flame retardants (red phosphorus, phosphoric acid esters and halogenated phosphoric acid esters, etc.) and nitrogen Department of flame retardants, etc. [0003] Since halogenated flame retardants generate more smoke and release irritating and corrosive gases during combustion, pollute the environment and endanger human health; the European Union ha...

Claims

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Application Information

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IPC IPC(8): C07F9/24C07F9/40C07F9/6506C08G18/32C08G77/30C08G63/692C08L67/02
CPCC07F9/4075C07F9/4006C07F9/2408C07F9/247C07F9/6506C08G18/3889C08G77/30C08G63/6928C08L67/02C08L2201/02
Inventor 潘庆崇
Owner GUANGDONG GUANGSHAN NEW MATERIALS CO LTD
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