CN102504244A - Synthesis and preparation method of melamine modified non-halogen inflaming retarding polyether - Google Patents
Synthesis and preparation method of melamine modified non-halogen inflaming retarding polyether Download PDFInfo
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Abstract
The invention discloses a preparation method of non-halogen inflaming retarding polyether. The preparation method disclosed by the invention is characterized in that a construction method comprises the following steps of: adding melamine, trioxymethylene and an organic solvent into a four-mouth flask with a water knockout drum in a certain proportion; stirring, regulating the pH value to 7.5-10, heating to 60-90 DEG C, reacting for 5-45 minutes and cooling to 30-50 DEG C, so as to obtain polyhydroxy methyl melamine; adding a certain amount of polyether polyol, regulating the pH value to 4.5-7, heating to 70-120 DEG C, and vacuumizing to minus 0.05-minus 0.8 MPa; reacting for 1-3 hours, heating to 90-120 DEG C, and vacuumizing to minus 0.1MPa; carrying out vacuum distillation for 1-2 hours, removing low molecular weight substances such as a solvent, cooling and discharging, so as to obtain the melamine modified inflaming retarding polyether polyol. The construction method disclosed by the invention is simple in process and low in cost; prepared polyether polyol is small in viscosity, good in mobility, low in fuming amount and more environment-friendly, and does not contain halogen and a phosphorous element; and a polyurethane foam material prepared from polyether polyol is strong in loading capability, good in inflaming retarding property and high in oxygen index.
Description
Technical field
The present invention relates to prepare the synthesis preparation method of modified flame-retardant polyethers through many melamine methylols and polyether reactant.
Background technology
Urethane foam (PUF) is one of principal item of polyurethane synthetic material; Have excellent mechanical property, thermal property, acoustical behavior, electric property and high stability, thereby have a wide range of applications aspect shockproof in refrigeration, insulation, sound absorption sound insulation, liner.Therefore common density polyurethane foam is less, and is big to the air contact area, all be combustible polymers, and can produce a large amount of dense smoke and toxic gas, serious threat people's property and life security when burning.Therefore, the resistance combustion polyurethane foam material is the focus of industry research and development always.
Through adding fire retardant, can obtain the flame retarded polyurethane foams material; Also can be through polyvalent alcohol and polyisocyanate compound are carried out modification; Introduce elements such as fire-retardant halogen, phosphorus, nitrogen; Form fire-retardant polyvalent alcohol and POLYMETHYLENE POLYPHENYLISOCYANATE, the polyurethane foam that is prepared by these polyvalent alcohols or POLYMETHYLENE POLYPHENYLISOCYANATE also has certain flame retardant resistance.The polyether glycol of having introduced ignition-proof element is called " flame retarding polyether ", also can be included into reactive flame retardant, but generally speaking is still polyether glycol.Compare with additive flame retardant, because flame retardant polyether polyol is participated in reaction, stable is attached in the polyurethane matrix, can in the life-time service process, not separate out and reduces flame retardant properties.
Different according to the ignition-proof element that adds, flame retarding polyether has following several kinds:
1) phosphorous polyether glycol and phosphorous chloride polyether glycol
Phosphorous chloride polyethers is a raw material with SULPHOSUCCINIC ACID ESTER, Vanadium Pentoxide in FLAKES, POCl3 or tetrahydroxy phosphorus chloride etc. generally; With reactions such as terepthaloyl moietie, glycerine; As initiator; With oxyethane, propylene oxide or epichlorohydrin reaction, generate the polyether glycol of phosphorous (and chloride) element again.This type of flame retarding polyether is owing to contain phosphorus oxygen key, so hydrolytic resistance is poor, the acidic substance that its hydrolysis produces in the being configured to foam combination material part tertiary amine catalyst that can neutralize lowers catalytic activity.
2) halogenated polyether polyvalent alcohol
Generally with 4,4,4-three chloro-1,2-butylene oxide ring or 4,4,4-three bromo-1, halo olefin oxides such as 2-butylene oxide ring are monomer, adopt lewis acid catalyst, behind ring-opening polymerization, promptly make chloride or brominated polyether glycol.
3) polyether glycol of phosphorous, chlorine, antimony
In glycerine, add butter of antimony, wait to dissolve the back and add POCl3, react the back decompression and steam HCl, drip epoxy chloropropane or propylene oxide, reaction makes the flame retarding polyether that hangs down acidity.
More than several kinds of flame retarding polyethers all contain halogen and phosphoric, its goods are in case burning, the amount of being fuming is big, be prone to produce pungency or toxic gas, causes fire field environment more complicated, is unfavorable for safety more.Secondly, the environmental issue of halogen-containing flame retardant and the harm of human body more and more caused people's attention.Some developed countries in Europe have gradually reduced or have forbidden halogen-containing fire-retardant agent now.On January 17th, 2008, Norway's government announces that externally it will come into force on April 1st, 2008 about the one-sided ban that bans use of decabromodiphynly oxide (Deca-BDE).The use of considering decabromodiphynly oxide is to environment and the healthy influence that brings, and Deca-BDE all Application Areass except that transportation transmission effect have been contained in this ban.At present, China's business circles have also given great concern to the application prospect of halogenated flame retardant, seek the trend of policies and product innovation alternative information one after another.
The nitrogen flame retardant can generate the lower non-combustible materials of toxicity simultaneously in kindling temperature or divide heat of desorption near under the kindling temperature, mainly is rare gas elementes such as nitrogen, thereby plays fire retardation, and the amount of being fuming is low, is one of the most promising environment friendly flame retardant at present.Trimeric cyanamide is exactly a kind of nitrogen flame retardant, has the low advantage of environment-protecting asepsis cost, is widely used in the fire-retardant of urethane foam in areas such as Europe.Generally trimeric cyanamide is ground to form thinner particle, join in the polyether glycol, be made into suspension-s, foam.Except the advantage of Environmental Safety, trimeric cyanamide also has the total shortcoming of all additive flame retardants, promptly in polyethers, has consistency difference problem, also can cause negative impact to the Physical Mechanical of end article, and this has limited the scope of its use.
Through covalent linkage trimeric cyanamide being introduced on the polyether backbone is the effective ways that address these problems.Trimeric cyanamide is mainly contained two kinds now with the method that chemical bond inserts polyether backbone, and a kind of is through reacting with POLYMETHYLENE POLYPHENYLISOCYANATE, form urea groups, inserting in the polyethers; Another kind is to be that initiator prepares polyethers with the trimeric cyanamide, thereby it is combined with polyether backbone with chemical bond.Chinese patent CN1583829 is through obtaining the poly-hydroxy trimeric cyanamide with trimeric cyanamide and formolite reaction; Generate with the hydramine reaction then and contain amino etherify melamine liquid; Pass through polyisocyanate compound again with trimeric cyanamide liquid and polyether grafting, become the modified flame-retardant polyethers that contains the polyureas group.This polyethers oxygen index is high, elements such as not halogen-containing, phosphorus, and material fluidity is good, and can keep goods good homogeneous property and physical strength, but also has complex process, problem more rambunctious.The public announcement of a patent application of application number 201010104605.7 a kind of compound method of flame-retardant rigid-foam polyether polyol; Adopt multicomponent alcoholics compound and trimeric cyanamide to form and mix initiator; At 0-0.5MPa pressure, under the 50-150 ℃ of temperature, be catalyzer with basic metal; Carry out polymerization with propylene oxide and obtain, wherein to account for the ratio of multicomponent alcoholics compound and trimeric cyanamide total mass be 50-80% to trimeric cyanamide.The novel flame-retardant rigid-foam polyether polyol that the present invention makes can separately or mix use with other rigid-foam polyether; The configuration combined polyether; With it is the preparation that the combined polyether of configurations can be used in flame-retardant hard polyurethane foaming plastic; Especially when being used for the fire-retarding spray coating polyurethane preparation, have good stability, oxygen index height, good flame retardation effect, characteristics such as with low cost.But this processing requirement is comparatively strict, and investment is big, and product also exists viscosity big, influences material fluidity, thereby also influences the shortcoming of product properties.
Summary of the invention
To the weak point of above-mentioned existing polyurethane flame-proof technology, this has provided a kind of by many melamine methylols graft modification polyether glycol clearly, produces the technological method of flame retarding polyether; Through the hydroxyl of polyethers and the hydroxyl generation etherification reaction of many melamine methylols, trimeric cyanamide is linked in the polyether backbone with covalent linkage, the polyethers flame retardant properties that obtains is good; Not halogen-containing and phosphoric, system viscosity is little, good fluidity; Technology is simple, and is with low cost.By the polyurethane foamed material of its preparation, supporting capacity is strong, and flame retardant properties is good, and oxygen index is high.
Implementation method of the present invention is following:
In the four-hole boiling flask that water trap and prolong are housed, add a certain amount of trimeric cyanamide, trioxymethylene and organic solvent in proportion, mix and stir, add alkaline pH value regulator; Regulate pH to 7.5～10, be heated to 60～90 ℃, reacted 5～45 minutes; Be cooled to 30～50 ℃, obtain many melamine methylols, add a certain amount of polyether glycol then; Regulate between pH value to 4.5～7, be heated to 70～120 ℃, keep simultaneously reaction flask internal pressure-0.05～-0.08MPa between; Reacted 1-3 hour, and be warming up to 90-120 ℃, be evacuated to-0.1MPa; Remove small-molecule substances such as solvent in underpressure distillation 1-2 hour, cool off, obtain the flame retarding polyether of trimeric cyanamide graft modification.
The used trimeric cyanamide and the ratio of trioxymethylene are 1:1-2 in said.
The hydroxyl value of the polyether glycol in said is between 40～450mgKOH/g, and functionality is that molecular weight is between 400～5000 between 2～4.
Alkaline pH value regulator in said is a kind of in sodium hydroxide, yellow soda ash, sodium hydrogencarbonate, triethylamine, diethylamine, the magnesium basic carbonate.
Described solvent comprises the mixture of a kind of in normal hexane, sherwood oil, toluene, YLENE, ethylbenzene, acetone, THF, the ETHYLE ACETATE or two kinds, and consumption is 10～35% (quality) of polyether glycol.
Described acidic ph modifier comprises a kind of in hydrochloric acid, sulfuric acid, the tosic acid.
The present invention compared with prior art has following advantage:
1. the present invention is the hydroxyl formation ehter bond through hydroxyl in the poly-hydroxy trimerization hydrogen cyanamide and polyether glycol, trimeric cyanamide is grafted on the pfpe molecule chain, thereby obtains flame retarding polyether, and the simple cost of technology is low.Trimeric cyanamide is connected with covalent linkage with polyethers, has formed the mixing of molecular level, compares with direct interpolation trimeric cyanamide, has increased consistency, can effectively reduce viscosity.
2. with respect to the alkoxyl group segment of polyethers, the trimeric cyanamide unit has stronger rigidity, become the part of urethane foam molecular structure after, foams are had the enhanced effect, can improve the mechanical property of goods, and can improve percentage of open area.
3. the trimeric cyanamide unit has kept the molecular structure of itself, and temperature still can be divided heat of desorption, and become non-combustible materials near point of ignition the time, plays fire retardation, and gained modified polyether oxygen index is high, and flame retardant properties is good.
Not halogen-containing, the phosphoric of flame retardant polyether polyol of the present invention's preparation, the amount of being fuming is low, more Environmental Safety.
Embodiment
Below in conjunction with embodiment the present invention is done further elaboration in detail.
Embodiment 1:
In the four-hole boiling flask that is connected to water trap and prolong, add trioxymethylene 30g, trimeric cyanamide 28g, toluene 60mL stirs; Use concentration is 50% triethylamine aqueous solution adjusting pH value to 9, is heated to 70 ℃, after system is clarified fully, reacts 8 minutes again; Be cooled to 50 ℃ then, add polyether glycol (3050) 500g, drip the salt acid for adjusting pH value to 5.5 of 0.1mol/L, be evacuated to-0.06MPa; Be heated with stirring to 90 ℃ of reactions 1.5 hours, be warming up to 105 ℃, be evacuated to-0.1MPa; Underpressure distillation 1 hour removes small-molecule substances such as solvent, and cooling obtains white flame retardant polyether polyol; Solid content (the poly-hydroxy trimeric cyanamide accounts for the per-cent of flame retarding polyether total mass) is 10%, viscosity 1900mPa.s, and this polyethers foaming gained flex foam oxygen index is 23.
Embodiment 2:
In the four-hole boiling flask that is connected to water trap and prolong, add trioxymethylene 30g, trimeric cyanamide 42g, THF 30mL, toluene 30mL; Stir, use concentration is 10% aqueous sodium hydroxide solution adjusting pH value to 8.5, is heated to 75 ℃, after system is clarified fully; Reacted again 10 minutes, and be cooled to 30 ℃ then, add polyether glycol (3050) 288g, drip the sulphur acid for adjusting pH value to 5.5 of 0.1mol/L; Be evacuated to-0.05MPa, be heated with stirring to 80 ℃ of reactions 2 hours, be warming up to 100 ℃, be evacuated to-0.1MPa; Underpressure distillation 1 hour removes small-molecule substances such as solvent, and cooling obtains white flame retardant polyether polyol; Solid content (the poly-hydroxy trimeric cyanamide accounts for the per-cent of flame retarding polyether total mass) is 20%, viscosity 3400mPa.s, and this polyethers foaming gained flex foam oxygen index is 25.
Embodiment 3:
In the four-hole boiling flask that is connected to water trap and prolong, add trioxymethylene 30g, trimeric cyanamide 35g, YLENE 30mL, THF 30ml; Stir, use concentration is 10% aqueous sodium carbonate adjusting pH value to 8.5, is heated to 75 ℃, after system is clarified fully; Reacted 15 minutes again, and be cooled to 40 ℃ then, add polyether glycol (3050) 195g, the tosic acid that drips 0.1mol/L is regulated pH value to 5.5; Be evacuated to-0.06MPa, be heated with stirring to 90 ℃ of reactions 2.5 hours, be warming up to 105 ℃, be evacuated to-0.1MPa; Underpressure distillation 1 hour removes small-molecule substances such as solvent, and cooling obtains white flame retardant polyether polyol; Solid content (the poly-hydroxy trimeric cyanamide accounts for the per-cent of flame retarding polyether total mass) is 25%, viscosity 4900mPa.s, and this polyethers foaming gained flex foam oxygen index is 29.
Embodiment 4:
In the four-hole boiling flask that is connected to water trap and prolong, add trioxymethylene 30g, trimeric cyanamide 28g, toluene 60mL stirs; Use concentration is 50% triethylamine aqueous solution adjusting pH value to 8.5, is heated to 75 ℃, after system is clarified fully, reacts 8 minutes; Be cooled to 50 ℃ then, add polyether glycol (4110) 232g, drip the salt acid for adjusting pH value to 5.5 of 0.1mol/L, be evacuated to-0.06MPa; Be heated with stirring to 90 ℃ of reactions 1.5 hours, be warming up to 105 ℃, be evacuated to-0.1MPa; Underpressure distillation 1 hour removes small-molecule substances such as solvent, and cooling obtains white flame retardant polyether polyol; Solid content (the poly-hydroxy trimeric cyanamide accounts for the per-cent of flame retarding polyether total mass) is 20%, viscosity 2900mPa.s, and the hard foamed gained porous plastics of this polyethers oxygen index is 27.
Embodiment 5:
In the four-hole boiling flask that is connected to water trap and prolong, add trioxymethylene 30g, trimeric cyanamide 26g, toluene 60mL stirs; Use concentration is 50% triethylamine aqueous solution adjusting pH value to 8.5, is heated to 75 ℃, after system is clarified fully, reacts 8 minutes; Be cooled to 50 ℃ then, add polyether glycol (4110) 168g, the tosic acid that drips 0.1mol/L is regulated pH value to 5.0, is evacuated to-0.07MPa; Be heated with stirring to 85 ℃ of reactions 1.5 hours, be warming up to 105 ℃, be evacuated to-0.1MPa; Underpressure distillation 1 hour removes small-molecule substances such as solvent, and cooling obtains white flame retardant polyether polyol; Solid content (the poly-hydroxy trimeric cyanamide accounts for the per-cent of flame retarding polyether total mass) is 25%, viscosity 5200mPa.s, and this polyethers foaming gained rigid foam oxygen index is 31.
Embodiment 6:
In the four-hole boiling flask that is connected to water trap and prolong, add trioxymethylene 30g, trimeric cyanamide 21g, toluene 25mL, THF 25mL; Stir, use concentration is 10% aqueous sodium hydroxide solution adjusting pH value to 8.5, is heated to 75 ℃, after system is clarified fully; Reacted 10 minutes, and be cooled to 30 ℃ then, add polyether glycol (4110) 153g, drip the sulphur acid for adjusting pH value to 5.5 of 0.1mol/L; Be evacuated to-0.06MPa, be heated with stirring to 90 ℃ of reactions 2 hours, be warming up to 105 ℃, be evacuated to-0.1MPa; Underpressure distillation 1 hour removes small-molecule substances such as solvent, and cooling obtains white flame retardant polyether polyol; Solid content (the poly-hydroxy trimeric cyanamide accounts for the per-cent of flame retarding polyether total mass) is 25%, viscosity 4300mPa.s, and this polyethers foaming gained rigid foam oxygen index is 29.
Use soft bubble polyethers of method correctability of the present invention and rigid-foam polyether, and the urethane foam that makes of corresponding modified polyether, to compare with unmodified Texin 5590 foam, oxygen index is high, and good flame retardation effect can satisfy the security against fire requirement.
Data among above-mentioned each embodiment of the present invention are recorded by following method:
Viscosity is recorded under 20 degrees centigrade by NDJ-79 type rotary viscometer.
The soft bubble foaming formulation of polyethers is following: modified polyether polylol 100, and TDI80/20 40, triethylenediamine 0.3, dibutyl tin laurate 0.25, suds-stabilizing agent is an amount of, and foam stabilizer is an amount of, water 3.0,, HCFC-141b 3.
The polyethers foaming formulation that hard bubbles is following: modified polyether polylol 100, and PAPI 140, and triethylenediamine is an amount of, and dibutyl tin laurate is an amount of, and suds-stabilizing agent is an amount of, and foam stabilizer is an amount of,, HCFC-141b 20.
Limiting oxygen index determination obtains in the test of JF-3 type oxygen index instrument according to the method for GB/T 2406-88, and the thick size of the length and width of batten is respectively 120mm, 10mm, 10mm.
Claims (4)
1. the preparation method of a cyanurotriamide modified flame retarding polyether is characterized in that, implementation method is following: trimeric cyanamide, trioxymethylene and organic solvent in certain ratio are joined in the four-hole boiling flask that has water trap, stir; Regulate pH value to 7.5～10, be heated to 60～90 ℃, reacted 5～45 minutes; Be cooled to 30-50 ℃, obtain many melamine methylols, add a certain amount of polyether glycol then; Regulate pH value to 4.5～7, be heated to 70～120 ℃, be evacuated to-0.05～-0.8MpaMPa; Reacted 1～3 hour, and be warming up to 90-120 ℃, be evacuated to-0.1MPa; Removed small-molecule substances such as solvent in underpressure distillation 1-2 hour, cooling discharging obtains cyanurotriamide modified flame retardant polyether polyol.
2. according to the described flame retarding polyether preparation method of claim 1, it is characterized in that used trimeric cyanamide and trioxymethylene mol ratio are 1:1～2, both total masses and polyether glycol ratio are 10-35:100.
3. according to the described flame retarding polyether preparation method of claim 1, it is characterized in that used organic solvent comprises a kind of in toluene, YLENE, acetone, THF, the sherwood oil or more than one mixture.
4. according to the described flame retarding polyether preparation method of claim 1, the hydroxyl value that it is characterized in that used polyether glycol is between 40～450mgKOH/g, and functionality is that molecular weight is between 400～5000 between 2～4.
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| CN103289076A (en) * | 2013-05-07 | 2013-09-11 | 江苏长华聚氨酯科技有限公司 | Method for preparing flame retarding polyether from melamine |
| CN103539930A (en) * | 2013-10-14 | 2014-01-29 | 江苏钟山化工有限公司 | Dicyandiamide-modified flame-retardant polyether polyol preparation method, and prepared flame-retardant polyether polyol and application thereof |
| CN103554473A (en) * | 2013-10-31 | 2014-02-05 | 淄博德信联邦化学工业有限公司 | Preparation method of phosphorus-containing flame retardant polyether polyol |
| CN103755950A (en) * | 2014-01-16 | 2014-04-30 | 南京红宝丽股份有限公司 | Continuous preparation method of flame retardant polyether polyol |
| CN104844793A (en) * | 2015-05-27 | 2015-08-19 | 浙江万盛股份有限公司 | Preparation method and application of novel flame-retardant polyether glycol |
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| CN106046285A (en) * | 2016-05-27 | 2016-10-26 | 江苏长顺高分子材料研究院有限公司 | Method for producing melamine type series polyols |
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| CN103289076A (en) * | 2013-05-07 | 2013-09-11 | 江苏长华聚氨酯科技有限公司 | Method for preparing flame retarding polyether from melamine |
| CN103539930B (en) * | 2013-10-14 | 2016-09-07 | 江苏钟山化工有限公司 | The preparation method of the flame retardant polyether polyol of dicyandiamide modified and prepared flame retardant polyether polyol thereof and purposes |
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