CN106674436A - Preparation method of flame-retardant sound insulation type ultraviolet light cured polyurethane foamed plastic - Google Patents
Preparation method of flame-retardant sound insulation type ultraviolet light cured polyurethane foamed plastic Download PDFInfo
- Publication number
- CN106674436A CN106674436A CN201611156363.XA CN201611156363A CN106674436A CN 106674436 A CN106674436 A CN 106674436A CN 201611156363 A CN201611156363 A CN 201611156363A CN 106674436 A CN106674436 A CN 106674436A
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- China
- Prior art keywords
- diisocyanate
- sound insulation
- fire
- preparation
- insulation type
- 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.)
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- 239000003063 flame retardant Substances 0.000 title claims abstract description 43
- 238000009413 insulation Methods 0.000 title claims abstract description 39
- 229920003023 plastic Polymers 0.000 title claims abstract description 33
- 238000002360 preparation method Methods 0.000 title claims abstract description 27
- 229920002635 polyurethane Polymers 0.000 title claims abstract description 19
- 239000004814 polyurethane Substances 0.000 title claims abstract description 18
- 239000004033 plastic Substances 0.000 title claims abstract description 14
- 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 title abstract description 8
- 238000001723 curing Methods 0.000 claims abstract description 23
- 229920001568 phenolic resin Polymers 0.000 claims abstract description 21
- 239000005011 phenolic resin Substances 0.000 claims abstract description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 16
- 125000005442 diisocyanate group Chemical group 0.000 claims abstract description 15
- 150000005846 sugar alcohols Polymers 0.000 claims abstract description 15
- 239000004114 Ammonium polyphosphate Substances 0.000 claims abstract description 11
- 235000019826 ammonium polyphosphate Nutrition 0.000 claims abstract description 11
- 229920001276 ammonium polyphosphate Polymers 0.000 claims abstract description 11
- 239000003085 diluting agent Substances 0.000 claims abstract description 11
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 claims abstract description 9
- 239000003054 catalyst Substances 0.000 claims abstract description 7
- 239000004088 foaming agent Substances 0.000 claims abstract description 7
- 229920000877 Melamine resin Polymers 0.000 claims abstract description 3
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 claims abstract description 3
- 239000006260 foam Substances 0.000 claims description 32
- 239000000047 product Substances 0.000 claims description 23
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 20
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 14
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 12
- 239000000203 mixture Substances 0.000 claims description 12
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 11
- -1 tripolycyanamide Substances 0.000 claims description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 9
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- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 6
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- TUOBEAZXHLTYLF-UHFFFAOYSA-N [2-(hydroxymethyl)-2-(prop-2-enoyloxymethyl)butyl] prop-2-enoate Chemical compound C=CC(=O)OCC(CO)(CC)COC(=O)C=C TUOBEAZXHLTYLF-UHFFFAOYSA-N 0.000 claims description 5
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical group CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 claims description 5
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- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 claims description 4
- 239000000843 powder Substances 0.000 claims description 4
- 150000005206 1,2-dihydroxybenzenes Chemical class 0.000 claims description 3
- 239000005057 Hexamethylene diisocyanate Substances 0.000 claims description 3
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 3
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 claims description 3
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- KSBAEPSJVUENNK-UHFFFAOYSA-L tin(ii) 2-ethylhexanoate Chemical compound [Sn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O KSBAEPSJVUENNK-UHFFFAOYSA-L 0.000 claims description 3
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 claims description 3
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 3
- 239000003643 water by type Substances 0.000 claims description 3
- AXIWPQKLPMINAT-UHFFFAOYSA-N 1-ethyl-2,3-diisocyanatobenzene Chemical compound CCC1=CC=CC(N=C=O)=C1N=C=O AXIWPQKLPMINAT-UHFFFAOYSA-N 0.000 claims description 2
- GVEDOIATHPCYGS-UHFFFAOYSA-N 1-methyl-3-(3-methylphenyl)benzene Chemical group CC1=CC=CC(C=2C=C(C)C=CC=2)=C1 GVEDOIATHPCYGS-UHFFFAOYSA-N 0.000 claims description 2
- GWZMWHWAWHPNHN-UHFFFAOYSA-N 2-hydroxypropyl prop-2-enoate Chemical compound CC(O)COC(=O)C=C GWZMWHWAWHPNHN-UHFFFAOYSA-N 0.000 claims description 2
- BQZJOQXSCSZQPS-UHFFFAOYSA-N 2-methoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OC)C(=O)C1=CC=CC=C1 BQZJOQXSCSZQPS-UHFFFAOYSA-N 0.000 claims description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 2
- MHABMANUFPZXEB-UHFFFAOYSA-N O-demethyl-aloesaponarin I Natural products O=C1C2=CC=CC(O)=C2C(=O)C2=C1C=C(O)C(C(O)=O)=C2C MHABMANUFPZXEB-UHFFFAOYSA-N 0.000 claims description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 2
- OKKRPWIIYQTPQF-UHFFFAOYSA-N Trimethylolpropane trimethacrylate Chemical group CC(=C)C(=O)OCC(CC)(COC(=O)C(C)=C)COC(=O)C(C)=C OKKRPWIIYQTPQF-UHFFFAOYSA-N 0.000 claims description 2
- 230000018044 dehydration Effects 0.000 claims description 2
- 238000006297 dehydration reaction Methods 0.000 claims description 2
- 229940113088 dimethylacetamide Drugs 0.000 claims description 2
- 239000002270 dispersing agent Substances 0.000 claims description 2
- 239000003999 initiator Substances 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 238000000016 photochemical curing Methods 0.000 claims description 2
- 239000010703 silicon Substances 0.000 claims description 2
- 229910052710 silicon Inorganic materials 0.000 claims description 2
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims 8
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- LBDSQNRQXIKAGX-UHFFFAOYSA-N (2-methyl-3-prop-2-enoyloxypropyl) prop-2-enoate Chemical class C=CC(=O)OCC(C)COC(=O)C=C LBDSQNRQXIKAGX-UHFFFAOYSA-N 0.000 claims 1
- HVVWZTWDBSEWIH-UHFFFAOYSA-N [2-(hydroxymethyl)-3-prop-2-enoyloxy-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(CO)(COC(=O)C=C)COC(=O)C=C HVVWZTWDBSEWIH-UHFFFAOYSA-N 0.000 claims 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N alpha-methacrylic acid Natural products CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 8
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- 239000004753 textile Substances 0.000 abstract description 2
- 239000004566 building material Substances 0.000 abstract 1
- 238000003912 environmental pollution Methods 0.000 abstract 1
- 229920005830 Polyurethane Foam Polymers 0.000 description 12
- 239000011496 polyurethane foam Substances 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
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- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
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- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
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- 229910052736 halogen Inorganic materials 0.000 description 2
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- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 2
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- 239000007983 Tris buffer Substances 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F283/00—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
- C08F283/006—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to polymers provided for in C08G18/00
- C08F283/008—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to polymers provided for in C08G18/00 on to unsaturated polymers
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
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- 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
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Abstract
The invention relates to a preparation method of flame-retardant sound insulation type ultraviolet light cured polyurethane foamed plastic. According to the preparation method, melamine, pentaerythritol and ammonium polyphosphate are taken as an additive flame retardant, water is taken as a foaming agent, double-bond polyhydric alcohol containing melamine-phenolic resin (component B) is prepared from a catalyst, an active diluent, the flame retardant and the foaming agent, and a polyurethane foamed product with good flame retardance and sound insulation property is prepared from liquefied diisocyanate, the component B, a diisocyanate and the active diluent. The flame-retardant sound insulation type ultraviolet light cured polyurethane foamed plastic has the advantages that the flame retardance and sound insulation property are good, the radiation curing can be realized, the environmental pollution is low, the process is simple, the cost is low, the curing speed of a product is high, and the like; the flame-retardant sound insulation type ultraviolet light cured polyurethane foamed plastic can meet various demands required by the development of polyurethane foamed plastic products and can be used as a flame-retardant sound-insulation type foamed polyurethane product to be applied to the fields of building materials, electronic products, textiles and electric wires and cables.
Description
Technical field
The invention belongs to Functional polymer materials technology field, and in particular to a kind of fire-retardant sound insulation type ultraviolet curing urethane
The preparation method of foam plasticss.
Background technology
In polyurethaness product, most of is polyurethane foam class product.Polyurethane foam has light weight, softness, absolutely
Edge, ventilative, nontoxic, resilience are good, compression is little, moisture-proof ageing-resistant performance is excellent, and oil resistant, organic solvent-resistant, sound insulation,
Various good characteristics such as insulation are used widely in productive life.The density of flexible polyurethane foam is little, specific surface
Well, oxygen index (OI) only has 16 to larger, the adiabatic life of product, easily burns, while a large amount of toxic gas and flue dust are produced, once there is fire
Calamity, is likely to result in huge loss.The urgent of flame resistant material is essential with the enforcement of countries in the world security legislation and using department
Ask, develop anti-flammability flexible polyurethane foam, improve its safety in utilization.Have polyurethane by various methods
Fire resistance is always the much-talked-about topic in materialogy field, and at present, external research level can make polyurethane flexible foam not
In the case of affecting other properties, oxygen index (OI) reaches 30 or so, and can cross and realize industrialization, domestic research level and state at present
There is certain gap on border.Had been reported that using the monomer containing halogen-phosphorus or oligomer at present as ultraviolet light cross-linking body
The fire retardant of system, achieves good using effect, but, the fire retardant of halogen can produce poisonous and corrosion in burning
Property gas, the people that is exposed in acid poison can be made like that to suffocate, and damage the equipment of costliness.Noise is acknowledged as contemporary generation
One of the three big public hazards on boundary.The harm of noise on human class is very big, and not only danger is the auditory system of rank of nobility people, makes one tired, deaf, sternly
Ghost image rings the quality of life of resident, but also can accelerate the aging of building frame for movement, affect equipment and instrument precision and
Service life.Especially for the foam article for special vehicle, sound insulation value is even more very important important step.
The resin of ultraviolet light cross-linking solidification is obtained a wide range of applications in increasing field, particularly in foam plasticss
Industry, to replace the polyurethane product of traditional thermal-initiated polymerization.As other synthetic resin, the major defect of these resins
Also reside in their inflammability, and traditional fire proofing be use the method for machinery mixing using fire retardant matter as additive with
Obtained from resin alloy, but can cause to be crosslinked difficult and serious degraded after adding the inorganic filler of high-load, particularly
In ultraviolet light cross-linking system, this problem is especially serious.
Chinese invention patent（CN 01113573.5）Disclose the resistance of radiation-curable phosphorus contained ultra-branched polyurethane acrylate
Combustion agent and preparation method, react the phosphate ester trihydroxylic alcohol to be formed as response matrix with phosphoric acid and epoxide, by " pre-polymerization method "
Or " one-step method " adds the monohydroxy end-capss of diisocyanate and radiation-curable, the radiation-curable for obtaining is phosphorous super
Branched polyurethanes acrylate as fire retarding agent energy fast setting under ultraviolet irradiation, obtains clear hard cured film, with construction step
Suddenly the features such as simply, film and base material adhesive force are good, flame retarding efficiency is high, the outstanding advantages of this kind of invention are that it will not when being heated
Harmful gass are released, is so-called eco-friendly material, therefore has been obtained extensive attention and interest.But the invention is not yet related to
Fire retardant and preparation method thereof of the monomer or oligomer of Nitrogen element or halogen-containing-phosphorus as ultraviolet light cross-linking system
Problem.
International patent of invention（WO 9502004）Report by poly phosphate dihydroxylic alcohols and diisocyanate and hydroxy
Linear phosphorous urethane acrylate is made in acid esters reaction, adds light trigger and multi-functional acrylate as crosslinking
Radiation curing article formulations made by agent.Such an approach achieves radiation curable halogen-free fire-retardant, but as which is linear molecule,
A large amount of functional group propenoic acid esters be must be added to as cross-linking agent, regulation system viscosity and processing characteristics is improved, but most of propylene
Acid ester monomer has zest, is detrimental to health to skin；And the addition of acrylate monomer can affect the solidification speed of system
The mechanical property of rate and product.
The content of the invention
It is an object of the invention to provide a kind of preparation method of fire-retardant sound insulation type ultraviolet curing urethane foam plasticss, gram
Take the disadvantages mentioned above of prior art.
A kind of fire-retardant sound insulation type ultraviolet curing urethane foam plasticss that the present invention is provided, using tripolycyanamide, season penta
, used as addition sex flame retardant, water first synthesizes a kind of resin containing melamine-phenolic as foaming agent for tetrol and ammonium polyphosphate
Modified polyalcohol, then it is prepared into one kind using certain step with catalyst, reactive diluent, fire retardant and foaming agent
The polyhydric alcohol containing melamine-phenolic resin with double bond（Component B）, then will liquefy diisocyanate（Component A）, component B
The good polyurethane flexible foam of a kind of fire-retardant and sound insulation value is mixed to get with certain proportion with light trigger, reactive diluent
Plastic.
A kind of preparation method of fire-retardant sound insulation type ultraviolet curing urethane foam plasticss proposed by the present invention, concrete steps
It is as follows：
(1) the liquefaction diisocyanate of 40~60 weight portions is put into into beaker, and beaker sealing is put into into 50~60 DEG C of baking ovens
In, 20~40 more than min are stood, with thermometer measure liquefaction diisocyanate actual temperature, the reality of the diisocyanate that liquefies
Temperature is more than 50 DEG C, makes component A use；
(2) equipped with mechanical agitator, reflux condensing tube and nitrogen protection three-necked bottle in add 5~25 g tripolycyanamide and
20~40 g formalins（37% mass fraction）, stirring after being passed through nitrogen, oil bath heating 20~40 minutes obtains melamine
Amine-phenolic resin prepolymer；
(3) to step（2）80~120 mL deionized waters of addition in the melamine-phenolic resin prepolymer for obtaining, 0.2~
0.6 g PEG400s adjust pH value to 4~5 with acetic acid solution in advance as dispersant, solution system is heated to into 55~
75℃.Now prepolymer is added in there-necked flask, then is reacted 10~20 minutes, stopped reaction is quickly cooled down with frozen water, by institute
The product dispersion multiple high speed pellets of centrifugal precipitation mechanism are obtained, adds deionized water to disperse again, recentrifuge precipitation is obtained
White powder product, obtains final product the polyhydric alcohol containing melamine-phenolic resin；
(4) to step（3）5~15 g catechols and 0.01 are added in the polyhydric alcohol containing melamine-phenolic resin for obtaining
Temperature is risen to 80~100 DEG C by~0.1 g p-methyl benzenesulfonic acid, and is reacted 12~36 hours under magnetic stirring, reaction terminating
Afterwards, plus 5 in the product~10 g KH-570 silane couplers after being to slowly warm up to 110 DEG C, equilibrium temperature opens vacuum means
Put, after evacuation 1~3 h of dehydration is carried out to system, product is poured out, sealing preserve is simultaneously cooled to room temperature, obtains final product with double bond
Polyhydric alcohol containing melamine-phenolic resin；
(5) by step（4）The polyhydric alcohol containing melamine-phenolic resin with double bond that obtains, cross-linking agent, catalyst, silicon
Oil, water, tripolycyanamide, ammonium polyphosphate, tetramethylolmethane and organic solvent, with 100：(5~15)：(0.5~2.5)：(0.1~
1)：(0.5~2.5)：(10~20):(20~30):(8~15)：The weight ratio mixing of (80~120), and with 5O~250 r/
The speed mechanical of min stirs 5~30 min, system is sufficiently mixed uniformly, makes B component use；
(6) with mechanical stirring device with the speed of 100~30O r/min quickly by step（1）The component A that obtains, step（5）
B component, diluent and the ultraviolet initiator for obtaining in beaker with（40~60）：（80~120）：（15~25）：（0.5~
5) weight is poured into than 0.5~5 min of mixing, after foam surface refers to and does, is placed directly within
Irradiate under ultra-violet lamp, carry out 0.5~2 h of photocuring, finally place products into again in 105~115 DEG C of baking ovens ripening 0.5~
1.5 h, then take out from baking oven, are cooled to room temperature, obtain final product a kind of fire-retardant and good polyurethane flexible foam of sound absorption qualities
Plastics.
In the present invention, in step (1), described liquefaction diisocyanate can be aromatic diisocyanate, such as first
Benzene -2,4- diisocyanate, Toluene-2,4-diisocyanate, 6- diisocyanate, 4,4 '-methyl diphenylene diisocyanate, two isocyanide of 1,5- naphthalenes
Acid esters, ethylbenzene diisocyanate, 4,6- XDIs, 3,3 '-dimethyl diphenyl -4,4 '-diisocyanate or 3,
It is 3 '-dimethyl -4,4 '-methyl diphenylene diisocyanate, or aliphatic diisocyanate, such as hexamethylene diisocyanate, six sub-
Methyl diisocyanate, cyclohexyl diisocyanate, 4,4 '-dicyclohexyl methyl hydride diisocyanate or different two Carbimide. of Buddhist ketone
Ester etc..
In the present invention, the catalyst described in step (5) can be dibutyltin dilaurate, stannous octoate, N-
In methyl morpholine or triethylenediamine any one；Described organic solvent, can be acetone, butanone, dioxane, toluene,
One kind in dimethylbenzene, ethyl acetate, N-Methyl pyrrolidone, N,N-dimethylformamide or DMAC N,N' dimethyl acetamide etc. or
Two or more mixture.
In the present invention, organic solvent described in step (5) selected from gasoline, toluene, dimethylbenzene, dioxane, ethyl acetate,
One or more mixture in butyl acetate or butanone etc..
In the present invention, catalyst described in step (3) is selected from dibutyltin dilaurate, stannous octoate, N- methyl
In quinoline or triethylenediamine any one.
In the present invention, the cross-linking agent described in step (5) is hydroxy functional acrylate, can be specifically（Methyl）Third
Olefin(e) acid -2- hydroxyl ethyl esters,（Methyl）2-hydroxypropyl acrylate, trimethylolpropane diacrylate, three acrylic acid of tetramethylolmethane
In ester, or their arbitrary composition any one.
In the present invention, in the step (5), fire retardant is any one in tripolycyanamide, tetramethylolmethane or ammonium polyphosphate etc.
Or more than one, foaming agent is water.
In the present invention, the light trigger described in step (6) can be that benzophenone, benzoin methyl ether, Alpha-hydroxy are rested in peace
Fragrant ether, Alpha-hydroxy cumene ketone, 4'- (2- hydroxy ethoxies) -2- hydroxy-2-methyl propiophenones, Alpha-hydroxy cyclohexyl benzene
One kind or one in ketone, isopropyl thioxanthone, 2- (4- methylthio phenyl formoxyls) -2- morpholinopropanes or oligomeric-hydroxy-ketone
More than kind.
In the present invention, in the step (6), reactive diluent is acrylate or methacrylate, and acrylate is
Butyl acrylate, methacrylate are trimethylolpropane trimethacrylate, dimethacrylate or 2-
In methyl-1,3-propanediol diacrylate any one.Butyl acrylate, trimethylolpropane tris third have been selected in the present embodiment
Three kinds of reactive diluents such as olefin(e) acid ester (TMPTA) and dimethacrylate (DEGDMA).
A kind of fire-retardant and good polyurethane soft foamed plastics of sound absorption qualities, its formula are constituted, and weight share is calculated as：
The method have the characteristics that：1. the present invention is hindered as addition property using tripolycyanamide, ammonium polyphosphate and tetramethylolmethane etc.
Combustion agent, water can prepare the good fire-retardant sound insulation type ultraviolet curing urethane bubble of fire-retardant and sound insulation value as foaming agent
Foam plastics, when tripolycyanamide, ammonium polyphosphate and tetramethylolmethane addition are respectively 15 parts, 25 parts and 12 parts, polyurethane foam
The fire resistance of foam reaches best, and oxygen index (OI) is 30, belongs to the material from fiery self-extinguishment, meanwhile, obtained polyurethane foam is led to
Cross sound insulation value test, in the range of 125 Hz to the 4O00 Hz its average sound-absorption coefficient 0.9, by its made micropunch
Plate is in, low-frequency region maximum acoustic absorptivity is up to more than 0.95；2. fire-retardant sound insulation type ultraviolet curing urethane of the invention
Foam plasticss are a kind of radiation-curable pre-polymers, can directly be used as fire retardant body, without small molecule blend and resistance
Combustion additive etc., range of application is broader；3. the polyurethane foam plastics obtained in us is greenization preparation technology, nothing
VOA volatilizees, and the pollution to environment is little, and, using ultraviolet light polymerization, curing rate is fast, disclosure satisfy that polyurethane foam plastics
The required curing rate of product development.
The present invention has that fire resistance is good, sound insulation value is good, radiation-hardenable, process is simple little to the pollution of environment, into
The advantages of this low and product quick solidifying, the required various needs of polyurethane foam article development can be met, can be used as resistance
Combustion sound-proof foam polyurethane product is applied to the fields such as construction material, electronic product, textile and electric wire, and market prospect is more
It is big and more extensive using future.
Specific embodiment
With reference to embodiment to a kind of preparation side of fire-retardant sound insulation type ultraviolet curing urethane foam plasticss of the present invention
Method, radiation curing and its fire-retardant sound insulation value etc. are described in detail.But the present invention is not limited to listed example.
Embodiment 1
By the 4 of 50 weight portions, 4 '-methyl diphenylene diisocyanate is put in a beaker, and beaker sealing is put into 55 DEG C of bakings
In case, 30 more than min are stood, with thermometer measure liquefaction diisocyanate actual temperature, the actual temperature of the diisocyanate that liquefies
Degree makes component A use more than 50 DEG C；
12.6 g tripolycyanamide and 24.5 g are added in the three-necked bottle equipped with the protection of mechanical agitator, reflux condensing tube and nitrogen
Formalin（37% mass fraction）, stirring after being passed through nitrogen, oil bath heating 30 minutes obtains a kind of melamine-phenolic tree
Fat prepolymer；
Add 100 mL deionized waters in above-mentioned melamine-phenolic resin prepolymer, 0.4 g PEG400s as point
Powder, adjusts pH value to 4.5 with acetic acid solution in advance, solution system is heated to 60 DEG C.Prepolymer is added into three mouthfuls of burnings now
In bottle, then react 15 minutes, stopped reaction is quickly cooled down with frozen water, will be products therefrom dispersion multiple with centrifugal precipitation mechanism
High speed pellets, add deionized water to disperse again, and recentrifuge precipitation obtains white powder product, obtain final product a kind of containing trimerization
The polyhydric alcohol of cyanamide-phenolic resin；
5.6 g catechols and 0.025 g p-methyl benzenesulfonic acid are added in the above-mentioned polyhydric alcohol containing melamine-phenolic resin,
Temperature is risen to into 95 DEG C, and is reacted 24 hours under magnetic stirring, after reaction terminating, in the product plus 8 g KH-570 silane idols
Connection agent after being to slowly warm up to 110 DEG C, equilibrium temperature opens vacuum extractor, and system is carried out after evacuation is dehydrated 2 h, to produce
Thing is poured out, and sealing preserve is simultaneously cooled to room temperature, obtains final product a kind of polyhydric alcohol containing melamine-phenolic resin with double bond；
By the above-mentioned polyhydric alcohol containing melamine-phenolic resin with double bond, trimethylolpropane diacrylate, dibutyl
Stannum dilaurate, silicone oil, water, tripolycyanamide, ammonium polyphosphate, tetramethylolmethane and dioxane etc., with 100：10：1.5：
0.2：2：15：25：12：The ratio mixing of 100 (weight), and 15 min are stirred with the speed mechanical of 200 r/min, fill system
Divide mix homogeneously, make B component use；
Quickly component A and B component, butyl acrylate and Alpha-hydroxy are rested in peace with the speed of 20O r/min with mechanical stirring device
Fragrant ether is in beaker with 50：100：20：The ratio of 1 (weight) mixes 3 min, pours into,
After foam surface refers to and does, with the ultra-violet lamp of 500W as radiation source, sample is placed in into irradiation solidification 1 under ultra-violet lamp directly
H, finally places products into 0.5 h of ripening in 110 DEG C of baking ovens again, then takes out from baking oven, is cooled to room temperature, obtains final product a kind of resistance
The good polyurethane flexible foam of combustion performance and sound insulation value.Polyurethane foam article after solidification is carried out into various performances
Test, including fire resistance and sound insulation value test.The polyurethane foam plastics is tested by fire resistance, and its oxygen index (OI) is
30, belong to the material from fiery self-extinguishment, meanwhile, obtained polyurethane foam is tested by sound insulation value, in 125 Hz to 4O00
In the range of Hz, its average sound-absorption coefficient is 0.9, by its made microperforated panel in, low-frequency region maximum acoustic absorptivity
Up to more than 0.95.
Embodiment 2
Using preparation condition same as Example 1, but step（5）It is middle with double bond containing many of melamine-phenolic resin
First alcohol, trimethylolpropane diacrylate, dibutyltin dilaurate, silicone oil, water, tripolycyanamide, ammonium polyphosphate, season
The ratio of penta tetrol and dioxane etc. is by 100：10：1.5：0.2：2：15：25：12：100 are changed into 100：5：0.5：0.1：0.5：
10：20：9：90 (weight) mix, and other are constant.
Embodiment 3
Using preparation condition same as Example 1, but step（5）It is middle with double bond containing many of melamine-phenolic resin
First alcohol, trimethylolpropane diacrylate, dibutyltin dilaurate, silicone oil, water, tripolycyanamide, ammonium polyphosphate, season
The ratio of penta tetrol and dioxane etc. is by 100：10：1.5：0.2：2：15：25：12：100 are changed into 100：15：2.5：1：2.5：
20：30：15：120 (weight) mix, and other are constant.
Embodiment 4
Using preparation condition same as Example 1, but step（6）Middle component A, B component, butyl acrylate and Alpha-hydroxy peace
The ratio of the fragrant ether of breath is by 50：100：20：1 is changed into 50：80：15：0.5 (weight) mixes, and other are constant.
Embodiment 5
Using preparation condition same as Example 1, but step（6）Middle component A, B component, butyl acrylate and Alpha-hydroxy peace
The ratio of the fragrant ether of breath is by 50：100：20：1 is changed into 60：120：20：2.5 (weight) mix, and other are constant.
Embodiment 6
Using preparation condition same as Example 1, but diluent butyl acrylate is changed to trimethylolpropane tris acrylic acid
Ester, its consumption are constant.
Embodiment 7
Using preparation condition same as Example 1, but diluent butyl acrylate is changed to diethylene glycol dimethacrylate
Ester, its consumption are constant.
Embodiment 8
It is same as Example 1, but Alpha-hydroxy benzoin ethyl ether is changed into Alpha-hydroxy cumene ketone.
Embodiment 9
It is same as Example 1, but Alpha-hydroxy benzoin ethyl ether is changed into α hydroxy cyclohexyl phenylketones.
Embodiment 10
It is same as Example 1, but Alpha-hydroxy benzoin ethyl ether is changed into isopropyl thioxanthone.
A kind of fire-retardant sound insulation type ultraviolet curing urethane foam plasticss prepared by above-described embodiment 2~10, its structure
It is same or like with the result of performance and embodiment 1, it is respectively provided with good fire resistance, sound insulation value, solidification rate fast etc.
Advantage, is a kind of good fire-retardant sound insulation type ultraviolet curing urethane foam plastic product.
Claims (10)
1. a kind of preparation method of fire-retardant sound insulation type ultraviolet curing urethane foam plasticss, it is characterised in that concrete steps are such as
Under：
(1) the liquefaction diisocyanate of 40~60 weight portions is put into into beaker, and beaker sealing is put into into 50~60 DEG C of baking ovens
In, 20~40 more than min are stood, with thermometer measure liquefaction diisocyanate actual temperature, the reality of the diisocyanate that liquefies
Temperature is more than 50 DEG C, makes component A use；
(2) equipped with mechanical agitator, reflux condensing tube and nitrogen protection three-necked bottle in add 5~25 g tripolycyanamide and
20~40 g formalins（37% mass fraction）, stirring after being passed through nitrogen, oil bath heating 20~40 minutes obtains melamine
Amine-phenolic resin prepolymer；
(3) to step（2）80~120 mL deionized waters of addition in the melamine-phenolic resin prepolymer for obtaining, 0.2~
0.6 g PEG400s adjust pH value to 4~5 with acetic acid solution in advance as dispersant, solution system is heated to into 55~
75℃；Now prepolymer is added in there-necked flask, then is reacted 10~20 minutes, stopped reaction is quickly cooled down with frozen water, by institute
The product dispersion multiple high speed pellets of centrifugal precipitation mechanism are obtained, adds deionized water to disperse again, recentrifuge precipitation is obtained
White powder product, obtains final product the polyhydric alcohol containing melamine-phenolic resin；
(4) to step（3）5~15 g catechols and 0.01 are added in the polyhydric alcohol containing melamine-phenolic resin for obtaining
Temperature is risen to 80~100 DEG C by~0.1 g p-methyl benzenesulfonic acid, and is reacted 12~36 hours under magnetic stirring, reaction terminating
Afterwards, plus 5 in the product~10 g KH-570 silane couplers after being to slowly warm up to 110 DEG C, equilibrium temperature opens vacuum means
Put, after evacuation 1~3 h of dehydration is carried out to system, product is poured out, sealing preserve is simultaneously cooled to room temperature, obtains final product a kind of band double
The polyhydric alcohol containing melamine-phenolic resin of key；
(5) by step（4）The polyhydric alcohol containing melamine-phenolic resin with double bond that obtains, cross-linking agent, catalyst, silicon
Oil, water, tripolycyanamide, ammonium polyphosphate, tetramethylolmethane and organic solvent etc., with 100：（5~15）：（0.5~2.5）：（0.1
~1）：（0.5~2.5）：（10~20）:（20~30）:（8~15）：（80~weight 120) than mixing, and with 5O~250
The speed mechanical of r/min stirs 5~30 min, system is sufficiently mixed uniformly, makes B component use；
(6) with mechanical stirring device with the speed of 100~30O r/min quickly by step（1）The component A that obtains, step（2）
B component, diluent and the ultraviolet initiator for obtaining in beaker with（40~60）：（80~120）：（15~25）：（0.5~
5) weight is poured into than 0.5~5 min of mixing, after foam surface refers to and does, is placed directly within
Irradiate under ultra-violet lamp, carry out 0.5~2 h of photocuring, finally place products into again in 105~115 DEG C of baking ovens ripening 0.5~
1.5 h, then take out from baking oven, are cooled to room temperature, obtain final product a kind of fire-retardant and good polyurethane flexible foam of sound absorption qualities
Plastics.
2. the preparation method of a kind of fire-retardant sound insulation type ultraviolet curing urethane foam plasticss according to claim 1, its
In being characterised by step (1), described liquefaction diisocyanate is aromatic diisocyanate or aliphatic diisocyanate.
3. the preparation method of a kind of fire-retardant sound insulation type ultraviolet curing urethane foam plasticss according to claim 2, its
The aromatic diisocyanate is characterised by for Toluene-2,4-diisocyanate, 4- diisocyanate, Toluene-2,4-diisocyanate, 6- diisocyanate, 4,4 '-two
Methylenebis phenyl isocyanate, 1,5- naphthalene diisocyanates, ethylbenzene diisocyanate, 4,6- XDIs, 3,3 '-
Dimethyl diphenyl -4,4 '-diisocyanate or 3,3 '-dimethyl -4, in 4 '-methyl diphenylene diisocyanate any one, institute
State aliphatic diisocyanate for hexamethylene diisocyanate, hexamethylene diisocyanate, cyclohexyl diisocyanate, 4,4 '-two
In diphenylmethane diisocyanate or different Buddhist ketone diisocyanate any one.
4. the preparation method of a kind of fire-retardant sound insulation type ultraviolet curing urethane foam plasticss according to claim 1, its
In being characterised by step (5), described catalyst is dibutyltin dilaurate, stannous octoate, N-methylmorpholine or Sanya
In ethyldiamine any one；Organic solvent described in step (5) is acetone, butanone, dioxane, toluene, dimethylbenzene, acetic acid second
One or more mixing in ester, N-Methyl pyrrolidone, N,N-dimethylformamide or DMAC N,N' dimethyl acetamide
Thing.
5. the preparation method of a kind of fire-retardant sound insulation type ultraviolet curing urethane foam plasticss according to claim 1, its
It is characterised by that the cross-linking agent described in step (5) is hydroxy functional acrylate.
6. the preparation method of a kind of fire-retardant sound insulation type ultraviolet curing urethane foam plasticss according to claim 5, its
It is characterised by that the hydroxy functional acrylate is（Methyl）Acrylic acid -2- hydroxyl ethyl esters,（Methyl）2-hydroxypropyl acrylate,
In trimethylolpropane diacrylate, pentaerythritol triacrylate, or their arbitrary composition any one.
7. the preparation method of a kind of fire-retardant sound insulation type ultraviolet curing urethane foam plasticss according to claim 1, its
Fire retardant described in step (5) is characterised by for one or more in tripolycyanamide, tetramethylolmethane or ammonium polyphosphate
Mixture, foaming agent is water.
8. the preparation method of a kind of fire-retardant sound insulation type ultraviolet curing urethane foam plasticss according to claim 1, its
It is characterised by that light trigger described in step (6) is that benzophenone, benzoin methyl ether, Alpha-hydroxy benzoin ethyl ether, Alpha-hydroxy are different
Propyl group benzophenone, 4'- (2- hydroxy ethoxies) -2- hydroxy-2-methyl propiophenones, Alpha-hydroxy phenylcyclohexyl ketone, isopropyl thioxanthone
Anthrone, 2- (4- methylthio phenyl formoxyls) -2- morpholinopropanes, oligomeric-hydroxy-ketone or any mixture between them.
9. the preparation method of a kind of fire-retardant sound insulation type ultraviolet curing urethane foam plasticss according to claim 1, its
It is characterised by that reactive diluent is acrylate or methacrylate described in step (6).
10. the preparation method of a kind of fire-retardant sound insulation type ultraviolet curing urethane foam plasticss according to claim 9, its
It is characterised by that acrylate is butyl acrylate, methacrylate is trimethylolpropane trimethacrylate, diethylene glycol two
In methacrylate or 2- methyl-1,3-propanediol diacrylates any one.
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