CN103242647B - Flame-retardant heat-resistant polyurethane foaming plastic and preparation method thereof - Google Patents

Flame-retardant heat-resistant polyurethane foaming plastic and preparation method thereof Download PDF

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CN103242647B
CN103242647B CN201310152248.5A CN201310152248A CN103242647B CN 103242647 B CN103242647 B CN 103242647B CN 201310152248 A CN201310152248 A CN 201310152248A CN 103242647 B CN103242647 B CN 103242647B
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flame
polyol
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heat
polyurethane foaming
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CN103242647A (en
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朱秀玲
井健
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Dalian University of Technology
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Abstract

The invention belongs to high molecular materials and in particular relates to flame-retardant heat-resistant polyurethane foaming plastic. The polymer, namely the flame-retardant heat-resistant polyurethane foaming plastic, contains a residue structure obtained after reaction of heterocyclic polyol and polyisocyanate, and a flame retardant or flame-retardant polyol is added in the preparation process. The flame-retardant heat-resistant polyurethane foaming plastic is prepared by carrying out a reaction on heterocyclic substances, polyester or polyester polyol, polyisocyanate, flame-retardant polyol and the like, or adding the flame retardant instead of the flame-retardant polyol. As the heterocyclic structure is introduced in polyurethane, except for the characteristics of the common polyurethane foaming plastic, the flame-retardant heat-resistant polyurethane foaming plastic further has excellent heat resistance, corrosion resistance and more excellent mechanical property and is high-grade flame-retardant polyurethane foaming plastic; and a preparation process of the flame-retardant heat-resistant polyurethane foaming plastic is environment-friendly and non-toxic. The defects that the existing polyurethane is low in heat resistance, poor in flame retardance and the like are overcome; and the flame-retardant heat-resistant polyurethane foaming plastic can be dried at low temperature, is convenient to use and high in cost performance and can be widely applied to the fields of industrial construction materials, high-grade building materials, heat-preservation and heat-insulation materials and the like.

Description

A kind of flame-proof heat-resistant urethane foam and preparation method thereof
Technical field
The present invention relates to a kind of urethane foam, belong to technical field of polymer materials.
Background technology
Urethane has excellent wear-resisting, heatproof, scratch resistance, solvent resistant, radiation hardness, low temperature elasticity, has excellent mechanical performance and molecular designing, is widely used in the fields such as porous plastics, rubber, fiber, coating, ink, tackiness agent, leather.Major part urethane is all inflammable material, and be the protection people security of the lives and property, developing flame retardant polyurethane in recent years becomes focus.Reach fire-retardant object mainly through adding fire retardant at present, and there is shortcomings such as easily moving, flame retardant effect is not lasting in small molecules fire retardant, even can destroy the physicals of urethane resin own.In recent years, polyurethane for time, add part band ignition-proof element monomer, intrinsic flame retardant polyurethane can be prepared, the shortcoming of additive flame flame-retardant polyurethane can be overcome, give urethane resin Good All-around Property simultaneously.
Rigid urethane foam has the character such as light weight, heat-insulation and heat-preservation, sound-absorbing buffering, is widely used in national economy every profession and trade, comprises each fields such as building, traffic, packaging, national defence.But general rigid urethane foam compressive strength is low, and mechanical property is poor, uses as structured material and be very limited.The same with most macromolecular material, rigid urethane foam is flammable, discharges the highly toxic substance such as carbon monoxide, prussic acid, therefore prepare flame-retardant polyurethane foam plastic extremely urgent during burning.Traditional method adds halogen system thing to carry out fire-retardant, but halogen system thing generates more smog, corrosive gases and toxic gas when burning, and works the mischief to human body and environment, therefore urgently develops environment friendly halogen-free fireproof urethane foam.Add nano material, polynite or carbon nanotube etc. by physics in recent years carry out fire-retardant and play enhancement, but the some mechanical performance of meeting expendable material.
summary of the invention:
The object of the invention is in order to overcome the shortcoming that in prior art, urethane foam thermotolerance is high, not inflammable, or additional halogen flame, discharges toxic gas during burning, the defect that the amount of being fuming is large, thus provide a kind of flame-proof heat-resistant urethane foam, environment friendly non-halogen, excellent fireproof performance; The present invention also provides its preparation method in addition, and technique is simple, easy handling.
The present invention seeks to be achieved through the following technical solutions: a kind of flame-proof heat-resistant urethane foam, it is characterized in that, containing heterocycle polyvalent alcohol and the reacted residues Structures of polyisocyanates in its polymkeric substance, add fire retardant or flame-proof polyol during preparation, in polymer molecular chain, comprise following structural unit:
formula I
Wherein, m, q are positive integers, and n is 0 and positive integer;
R 1, R 2, R 3, R 4for H, C 1~ C 6alkyl, alkoxyl group, halogen atom (F, Cl, Br, I), thiazolinyl or phenyl etc., they are identical or different structure;
When X is-NHCO-, R 8, R 9be polyisocyanates remove-(polyisocyanates structural formula is OCN-R for the residue of NCO group 8-NCO, OCN-R 9-NCO), be C 4~ C 16aliphatic group, alicyclic radical, C 6~ C 18aryl radical, they are identical or different structure;
X be chemical bond or-CO-time, R 8, R 9for chemical bond or C 4~ C 16aliphatic group or C 6~ C 18aryl radical, R 8, R 9it is identical or different structure;
Y 1being the residue that polyvalent alcohol removes-OH, is alkyl, alkoxyl group, alkyl or alkoxyl group etc. containing ester bond or carbonic acid ester bond;
When n ≠ 0, Y 2being the residue (flame-proof polyol structural formula is HO-Y-OH) that the reaction-type flame-retarding polyvalent alcohol of phosphorous, nitrogen or silicon removes-OH, is phosphoric acid ester, the phosphite polyols of phosphorous, nitrogen or silicon; Work as n=0, add fire retardant during polyreaction and improve flame retardant resistance;
Ar 1, Ar 2be remove in polyisocyanates-(polyisocyanates structural formula is OCN-Ar for the residue of NCO group 1-NCO), be C 4~ C 16aliphatic group, alicyclic radical, C 6~ C 18aryl radical, they are identical or different structures.
The preparation method of a kind of flame-proof heat-resistant of the present invention urethane foam is as follows: calculate in mass ratio, by 100 parts of polyethers or polyester polyol, 5-80 part heterocycle polyvalent alcohol, 0-70 part flame-proof polyol or 5-150 part fire retardant, 0.01-5 part whipping agent, 0-60 part ionic liquid, 0.01-5 part suds-stabilizing agent silicone oil, 0.02-3 part catalyzer and 0-15 part linking agent, be uniformly mixed at 15-30 DEG C, add the polyisocyanates with two or more isocyanate group, polyisocyanates and polyol mole ratio are 1.02:1-3:1, be uniformly mixed rear injection 10-45 DEG C of mould to foam, through 20-120 DEG C of slaking, namely fire-retardant heterocycle urethane foam is obtained.
Described heterocycle polyol structure is as follows:
（A）
Or (B)
P is 0-10 integer;
G is H ,-OH ,-COOH ,-NCO;
X is chemical bond ,-NHCO-, carbonyl-CO-;
R 1, R 2|, R 3, R 4for C 1~ C 6alkylidene group, alkoxyl group, halogen atom (F, Cl, Br, I) or alkylene, they are identical or different structures;
R 8, R 9for chemical bond or be C 4~ C 16aliphatic group, alicyclic radical, C 6~ C 18aryl radical, R 8, R 9it is identical or different structure.
Described heterocycle polyvalent alcohol A can be prepared by following methods:
Work as X, R 8, R 9when being chemical bond, G=H, heterocycle polyvalent alcohol A are diazanaphthalene biphenyl ketone bis-phenol;
When X is carbonyl-CO-, R 8, R 9for C 4~ C 16aliphatic group, alicyclic radical, C 6~ C 18aryl radical, R 8, R 9be identical or different structure, G is-OH or-COOH, and now, heterocycle polyvalent alcohol A method for making is as follows: by diazanaphthalene biphenyl ketone bis-phenol and excessive C 1-C 16binary of fatty acids (or hydroxycarboxylic acid), carries out reaction 1-24h at 50-150 DEG C, and reaction can add protonic acid, Louis acid catalysis or not add catalyzer, obtains product be heterocycle polyvalent alcohol A through separating and filtering.
Described flame-proof polyol is phosphoric acid ester or the phosphite polyols of phosphorous, nitrogen or silicon, comprises [(two (2-hydroxyethyl) is amino) methyl] (Fyrol-6), diethyl phosphoric acid (FRC-6) etc.; Described fire retardant is selected from phosphoric acid ester as Triphenyl phosphate, ammonium polyphosphate, polyphosphoric acid aluminium, organic modification montmonrillonite, expanded graphite or the flyash trade waste etc. that is main component with inorganic silicon, aluminium etc.
Described polyisocyanates is: aliphatics or alicyclic ring polyisocyanates, aromatic polyisocyanate, two or more isocyanate mixtures or the modified polyisocyanate obtained by modified polyisocyanate compound.
Described polyethers or polyester polyol are molecular weight 200-3000 and Weighted Average Functionality is polyether glycol or the polyester polyol of 2-4, wherein polyether glycol is selected from polyethylene oxide glycol, polypropylene oxide glycol, PTMG, or the homopolymerization of above-mentioned monomer or copolymer glycols or polyvalent alcohol, polyester polyol is selected from one or more mixtures in polyethylene glycol adipate glycol, poly-hexanodioic acid-BDO esterdiol, polyhexamethylene adipate glycol, polycaprolactone glycol, polycarbonate polyol.
Described whipping agent is conventional polyurethanes whipping agent, is selected from fluorine halohydrocarbon as HCFC-141b, CH 3c-C l2, Skellysolve A, pentamethylene, CO 2or at least one in water;
Described catalyzer is polyurethane foam field conventional catalyst, comprises organotin or tertiary amine compound, is selected from the one or more combination things such as dibutyl tin laurate, dibutyltin diacetate, stannous octoate, triethylamine, trolamine, triethylenediamine;
Described linking agent is TriMethylolPropane(TMP), glycerine, starch, Mierocrystalline cellulose, xylogen, sugar etc.
Described ionic liquid is imidazoles or pyrroline heterocyclic onium cations liquid, and in ionic liquid, anion structure is as follows: , wherein X is F, Cl, Br or I.
The invention has the beneficial effects as follows, in polyurethane structural, introduce heterocycle structure, on the one hand, overcome the shortcoming that current urethane foam thermotolerance is not high, can not use as structured material, give resistance toheat, the mechanical property of urethane resin excellence, meet as structured material service requirements, on the other hand, add fire retardant or flame-proof polyol, prepare flame-proof heat-resistant urethane, cooperative flame retardant effect is provided together with nitrogen heterocyclic structure, its flame retardant effect is by additional fire retardant or add flame-proof polyol reaction acquisition, wherein fire retardant or flame-proof polyol, not halogen-containing, be halogen-free flameproof, environmental protection, nontoxic, the toxic gases such as Dioxins can not be produced in flame, do not generate haloid acid and flue gas is few, thus obtain the flame-proof heat-resistant urethane foam of environmental protection, can be applicable to industrial structure material, top-grade building material, the fields such as heat preserving and insulating material.
accompanying drawing illustrates:
Fig. 1 is urethane foam infrared spectrogram prepared by embodiment 1.
Embodiment
Following examples are that the present invention is described in more detail, instead of limitation of the present invention.
The concrete composition of raw materials of embodiment 1-6 is as following table:
Composition of raw materials table:
Note: catalyst quality is polyvalent alcohol 0.05-5%; Flame-proof polyol consumption is polyvalent alcohol 1-80%; Amount of flame-retardant agent is polyvalent alcohol 10-150%.TMP: TriMethylolPropane(TMP); DMP:2,4,6 one three (dimethylamino methyl) phenol.
embodiment 1
In proportion by polyester polyol, heterocycle polyvalent alcohol A(G=H, X, R 8, R 9be chemical bond), catalyst A-33 0.5g, dibutyl tin laurate 0.5g, silicone oil, flame-proof polyol FRC-6 10g, TMP and water add in reactor, mix at 50 DEG C, add TDI and be uniformly mixed, inject mould and foam, then 50 DEG C of slaking 2h in an oven, namely obtain fire-retardant heterocycle urethane foam product.Limiting oxygen index(LOI) LOI is 28.
Obtained product detects through following testing method:
Examination of infrared spectrum: adopt the FTIR-430 Spectrometer spectrograph that Japanese JASCO company produces, film reflector or pellet technique test the infrared spectra of urethane foam.
Limiting oxygen index(LOI) is tested according to ASTM D-2863 standard.
3138.43cm in Fig. 1 -1for C-H stretching vibration absorption peak on phenyl ring; 3093.59cm -1and 2978.29cm -1place is CH 2stretching vibration absorption peak; 1722.71cm -1for C=O stretching vibration absorption peak; 1652.72cm -1place is the stretching vibration absorption peak of the C=O on DHPZ; 1597.86 cm -1and 1533.81cm -1place is the stretching vibration absorption peak of C=C on aromatic ring; 1463.35cm -1place is the stretching vibration absorption peak of N-N in DHPZ; 1232.04 cm- 1place is the stretching vibration absorption peak of aryl C-O; 1171.89cm- 1place is the stretching vibration absorption peak of N-C; 1094.30cm -1place is the stretching vibration absorption peak of alkyl C-O.Above result shows successfully to have prepared fire-retardant heterocycle urethane foam.
embodiment 2
By polyether glycol 4110, heterocycle polyvalent alcohol B, dibutyl tin laurate and trolamine 0.2g, bromobutyl methylimidazole salt, silicone oil, 30g flame-proof polyol Fyrol-6, DMP and water add in reactor, mix at 50 DEG C.Add PAPI, be uniformly mixed, inject mould and foam, then 60 DEG C of slaking 1h in an oven, namely obtain fire-retardant heterocycle urethane foam product.Limiting oxygen index(LOI) LOI is 27.
embodiment 3
By polyether glycol 4110, heterocycle polyvalent alcohol A(G=H, X, R 8, R 9be chemical bond), catalyst A-33 0.6g, dibutyl tin laurate 0.3g, phosphorus hexafluoride butyl methyl imidazole salts, silicone oil, 30g flame-proof polyol FRC-6, TMP and water add in reactor, mix at 50 DEG C.Add MDI-100, be uniformly mixed, inject mould and foam, then 80 DEG C of slaking 2h in an oven, namely obtain fire-retardant heterocycle urethane foam product.Limiting oxygen index(LOI) LOI is 30.
embodiment 4
By polyester polyol, heterocycle polyvalent alcohol B, catalyst A-33 0.2g, stannous octoate 0.7g, silicone oil, 20g flyash, DMP and water add in reactor, mix at 50 DEG C.Add PAPI, be uniformly mixed, inject mould and foam, then 50 DEG C of slaking 5h in an oven, namely obtain fire-retardant heterocycle urethane foam product.Limiting oxygen index(LOI) LOI is 28.
embodiment 5
By carbonate polyol, heterocycle polyvalent alcohol A(G=H, X, R 8, R 9be chemical bond), dibutyl tin laurate, silicone oil, 30g wilkinite, TMP and water add in reactor, mix at 50 DEG C.Add NDI, be uniformly mixed, inject mould and foam, then 60 DEG C of slaking 12h in an oven, namely obtain fire-retardant heterocycle urethane foam product.Limiting oxygen index(LOI) LOI is 29.
embodiment 6 (contrast)
By polyether glycol 4110, heterocycle polyvalent alcohol B, bromobutyl methylimidazole salt, catalyst A-33, silicone oil, 30g Triphenyl phosphate, TMP and water add in reactor, mix at 50 DEG C.Add PAPI, be uniformly mixed, inject mould and foam, then 50 DEG C of slaking 6h in an oven, namely obtain fire-retardant heterocycle urethane foam product.Limiting oxygen index(LOI) LOI is 28.

Claims (5)

1. a flame-proof heat-resistant urethane foam, is characterized in that, containing heterocycle material and the reacted residues Structures of polyisocyanates in polymkeric substance, adds fire retardant or flame-proof polyol during preparation;
Wherein the heterocycle structure of matter is as follows:
（A）
Or (B)
P is 0-10 integer;
G is H ,-OH ,-COOH ,-NCO;
X is chemical bond ,-NHCO-, carbonyl-CO-;
R 1, R 2, R 3, R 4for C 1~ C 6alkylidene group, alkoxyl group, halogen atom F, Cl, Br, I or alkylene, they are identical or different structures;
R 8, R 9for chemical bond or be C 4~ C 16aliphatic group, alicyclic radical, C 6~ C 18aryl radical, R 8, R 9it is identical or different structure;
Described polyisocyanates is: aliphatics or alicyclic ring polyisocyanates, aromatic polyisocyanate, two or more isocyanate mixtures or the modified polyisocyanate obtained by modified polyisocyanate compound;
Described flame-proof polyol is phosphoric acid ester or the phosphite polyols of phosphorous, nitrogen or silicon; Fire retardant is selected from phosphoric acid ester.
2. the preparation method of a kind of flame-proof heat-resistant urethane foam described in claim 1, it is characterized in that, calculate in mass ratio, by 100 parts of polyethers or polyester polyol, 5-80 part heterocycle material, 0-70 part flame-proof polyol or 5-150 part fire retardant, 0.01-5 part whipping agent, 0-60 part ionic liquid, 0.01-5 part suds-stabilizing agent silicone oil, 0.02-3 part catalyzer and 0-15 part linking agent, be uniformly mixed at 15-70 DEG C, add the polyisocyanates with two or more isocyanate group, polyisocyanates and polyol mole ratio are 1.02:1-3:1, be uniformly mixed rear injection 10-45 DEG C of mould to foam, through 20-120 DEG C of slaking, namely flame-retardant polyurethane foam plastic is obtained, the wherein said heterocycle structure of matter is as follows:
（A）
Or (B)
P is 0-10 integer;
G is H ,-OH ,-COOH ,-NCO;
X is chemical bond ,-NHCO-, carbonyl-CO-;
R 1, R 2, R 3, R 4for C 1~ C 6alkylidene group, alkoxyl group, halogen atom F, Cl, Br, I or alkylene, they are identical or different structures;
R 8, R 9for chemical bond or be C 4~ C 16aliphatic group, alicyclic radical, C 6~ C 18aryl radical, R 8, R 9it is identical or different structure; Described flame-proof polyol is phosphoric acid ester or the phosphite polyols of phosphorous, nitrogen or silicon; Fire retardant is selected from phosphoric acid ester; Described polyisocyanates is: aliphatics or alicyclic ring polyisocyanates, aromatic polyisocyanate, two or more isocyanate mixtures or the modified polyisocyanate obtained by modified polyisocyanate compound;
Described polyethers or polyester polyol are molecular weight 200-3000 and Weighted Average Functionality is polyether glycol or the polyester polyol of 2-4, wherein polyether glycol is selected from polyethylene oxide polyol, polyoxypropylene polyol, polytetrahydrofuran ethoxylated polyhydric alcohol, polyester polyol is selected from one or more in polyethylene glycol adipate glycol, poly-hexanodioic acid-BDO esterdiol, polyhexamethylene adipate glycol, polycaprolactone glycol, polycarbonate polyol;
Described whipping agent is conventional polyurethanes whipping agent fluorine halohydrocarbon HCFC-141b CH 3c-C l2, Skellysolve A, pentamethylene, CO 2, water, or wherein two or more composition;
Described catalyzer is polyurethane foam field conventional catalyst organotin or tertiary amine compound;
Described linking agent is TriMethylolPropane(TMP), glycerine, starch, Mierocrystalline cellulose, xylogen or sugar;
Described ionic liquid is imidazoles or pyrroline heterocyclic onium cations liquid, and in ionic liquid, anion structure is as follows: , wherein X is F, Cl, Br or I.
3. the preparation method of a kind of flame-proof heat-resistant urethane foam according to claim 2, is characterized in that: described flame-proof polyol is [(two (2-hydroxyethyl) is amino) methyl] or diethyl phosphoric acid.
4. the preparation method of a kind of flame-proof heat-resistant urethane foam according to claim 2, is characterized in that: described fire retardant is selected from Triphenyl phosphate, ammonium polyphosphate, polyphosphoric acid aluminium, organic modification montmonrillonite, expanded graphite or the flyash trade waste that is main component with inorganic silicon, aluminium.
5. the preparation method of a kind of flame-proof heat-resistant urethane foam according to claim 2, is characterized in that: described catalyzer is selected from one or more in dibutyl tin laurate, dibutyltin diacetate, stannous octoate, triethylamine, trolamine, triethylenediamine.
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