CN101575408A - Polytriazinyl compounds as flame retardants and light stabilizers - Google Patents
Polytriazinyl compounds as flame retardants and light stabilizers Download PDFInfo
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Abstract
Halogen-free self-extinguishing oligomeric or polymeric compounds derived from 1, 3, 5-triazine, having the general formula I wherein or a heterocyclic radical containing in the ring at least one nitrogen atom which radical is linked to the triazine ring through one of such nitrogen atoms, R 2 is alkyl or cycloalkyl, R 1 is a divalent radical of piperazine of the formula or a divalent radical of the type or n is an integer from 2 to 30, extremes included, m is an integer from 2 to 6, extremes included, p is an integer from 2 to 12 extremes included, and X 1 =OH, NH 2 or X, wherein X 1 and X may be the same or different, X 2 is a hydrogen or an C 1 -C 4 alkyl group, and a solvent-free process for the production of the compounds of Formula I as well as the use of the self-extinguishing oligomeric or polymeric compounds as flame retardants and light stabilizers in thermoplastic polymers such as polypropylene or regenerated cellulose or polyester.
Description
Technical field
The present invention relates to the halogen compound of general formula I,
Wherein
Or comprising the heterocyclic group of at least one nitrogen-atoms in the ring, this group is connected to triazine ring, R by a described nitrogen-atoms
2Be alkyl or cycloalkyl, R
1It is the divalent radical of the piperazine of following general formula
Or the divalent radical of following type
Or
N is 2 to 30 integer, comprises end value, and m is 2 to 6 integer, comprises end value, and p is 2 to 12 integer, comprises end value, X
2Be hydrogen or C
1-C
4Alkyl and
X
1=0H, NH
2Or X, wherein X
1With X can be identical or different.
The invention still further relates to the method for production compound of Formula I, preferably do not use any organic solvent, preferably in the presence of tensio-active agent.
Summary of the invention
The first step of the inventive method is according to prior art ,-10 ℃ to+10 ℃ temperature ranges, is 5 to 7 times in the pH value, at polar solvent for example in acetone, the water etc., but does not preferably use any organic solvent, makes cyanuric halogen and general formula R
2-NH
2Amine or with ring in comprise nitrogen-atoms heterogeneous ring compound be to react at 1: 1 with mol ratio, to obtain 2, the 4-aminoderivative of 6-two chloro-1,3,5-triazines.
Need not separate, under heat condition, in water or polar solvent, still preferably not use any organic solvent all the time then, suspension and general formula H in the middle of making
2N-(CH
2)
m-NH
2Amine, with piperazine or its alkyl-substituted derivative, with 4-amino-2,2,6,6-tetramethyl piperidine or N, N '-two-(2,2,6,6-tetramethyl--4-piperidyl)-1, the 6-hexanediamine or with the mixture reaction of these compounds, wherein the mol ratio between pyrrolotriazine derivatives and amine and/or the piperazine equals 1: 1.
Pass through at for example excessive HX of alkali then
1And/or under the existence of alkali metal hydroxide, under 90 ℃ to 150 ℃ temperature, more preferably under 100 ℃ to 130 ℃ the temperature, make intermediate compound and general formula HX
1Compound reaction, obtain the compound of general formula I.
Therefore, another object of the present invention is by cyanuric halogen in two or three steps and the suitably condensation of amine and/or heterogeneous ring compound, produces to have the water-fast 1,3,5-triazines derivative oligopolymer of following general formula or the method for polymkeric substance:
Wherein
Or comprising the heterocyclic group of at least one nitrogen-atoms in the ring, this group is connected to triazine ring, R by a described nitrogen-atoms
2Be alkyl or cycloalkyl, R
1It is the divalent radical of the piperazine of following general formula
Or the divalent radical of following type
Or
N is 2 to 30 integer, comprises end value, and m is 2 to 6 integer, comprises end value, and p is 2 to 12 integer, comprises end value, X
2Be hydrogen or C
1-C
4Alkyl and
X
1=OH, NH
2Or X, wherein X
1With X can be identical or different.
In order to keep reaction mixture to be suspension stably, preferably add for example Witco 1298 Soft Acid of tensio-active agent.The compound of Formula I that obtains is to have the very white powder of high-melting-point and minimum content of halogen.It can be ground and be small-particle, prepare then to incorporate thermoplastic polymer into other flame-retardant compound such as ammonium phosphate or phosphamide.
Can be according to known method production self-extinguishing composition of the present invention: for example, at first nearly ammonium phosphate or phosphamide are mixed with the triazine nitrogenous compound (preferably have and be lower than 75 microns particle) of fine grinding, and the mixture that will so obtain adds in the thermoplastic polymer in turbo mixer, to form uniform mixture, then this mixture is extruded and granulation.According to any known molding technique, the particulate product that so obtains can be transformed into various products.Flame-retardant additive of the present invention also is applicable to the anti-flaming dope field.
For mensuration comprises the polymeric composition self-extinguishing energy of flame-retardant additive, can carry out following operation: in the dull and stereotyped pressing machine of MOORE, by with 40kg/cm
2Pressure, operation is 7 minutes under suitable temperature, and particulate product is molded as 3 millimeters (1/8 inch) thick plates.Test this plate according to the UL-94 method then.
R wherein
1The poly-triaizine compounds of the general formula of=Y (I) is useful and valuable reagent, can be used for improving synthetic polymer to light, the stability of heat and oxidation, described synthetic polymer for example is height and new LDPE (film grade), polypropylene, ethylene-propylene copolymer, ethylene-vinyl acetate copolymer, polyhutadiene, polyisoprene, polystyrene, styrene-butadiene copolymer, acrylonitrile-butadiene-styrene copolymer, vinylchlorid and vinylidene chloride polymer and multipolymer, polyoxymethylene, the Polyethylene Terephthalates, nylon 66, nylon 6, nylon 12, urethane, unsaturated polyester.
R wherein
1The general formula of=Y (I) compound can be used as polyolefine especially and more is particularly useful as the polyolefin articles with minimizing thickness, for example photostabilizer of fiber and film.Surprisingly, when contacting, be difficult to extract described compound from described thin goods with water or water phase surfactant mixture.
R wherein
1The general formula of=Y (I) compound can adopt the mixture according to multiple ratio and synthetic polymer to use, and it depends on other additive of polymer property, end-use and existence.
With respect to polymer weight, the preferred usually wherein R of 0.01 to 5 weight % that uses
1The general formula of=Y (I) compound, more preferably 0.1 to 1%.
Can be with several different methods for example with the powder type dry blending, or with solution or slurry form wet method, R wherein
1The general formula of=Y (I) compound adds in the polymeric material composition.In described operation, synthetic polymer can adopt the form of powder, particle, solution, slurry or emulsion.
With R wherein
1The product stable polymer of the general formula of=Y (I) can be used to produce moulded product, film, band, fiber, monofilament etc.
R wherein
1The mixture of the general formula of=Y (I) compound and synthetic polymer can be chosen wantonly and add other additive, for example antioxidant, UV light absorber, nickel stablizer, pigment, electric charge agent (charges), fluidizer, static inhibitor, fire retardant, lubricant, rust-preventive agent, metal deactivator etc.
In the general formula I, R
2Preferably comprise the alkyl of 1 to 20 carbon atom or comprise the cycloalkyl of 6 to 20 carbon atoms, R
1The divalent radical of the divalent radical of piperazine or diamines preferably, wherein m is 2 to 6 integer, comprises end value, and n is 8 to 20 integer preferably, and p is 4 to 10 integer preferably, comprises end value.
The example of alkyl is methyl, ethyl, propyl group, normal-butyl, isobutyl-, hexyl, octyl group, decyl, dodecyl, cyclohexyl, propyl group-cyclohexyl, butyl-cyclohexyl, decyl cyclohexyl.The example that is defined as the heterocyclic group of X is morpholine, piperidines and piperazine.For R
1The example of diamines be quadrol, tetramethylene-diamine, five methylene diamine, hexamethylene-diamine.
Preferred compound of formula I is R
1Those compounds of=hexamethylene-diamine, piperazine and alkyl substituted-piperazinyl, and X wherein
1Be identical with X and have the compound of Formula I of morpholinyl, piperidyl or piperazinyl.
The following example explanation is according to the preparation of general formula A and some compound of I.Unless otherwise mentioned, whole umbers of pointing out in this preparation all are meant weight part.
Embodiment 1
To reactor pack into 150 parts of water, 150 parts ice and 0.2 part of Witco 1298 Soft Acid.Under agitation condition, in 15 minutes, add 74 parts of cyanuryl chlorides then.Stirred the mixture 15 minutes, and obtained uniform suspension.After forming suspension, add the 34.9 parts of morpholines and the 21.2 parts of yellow soda ash (100% basis (100%basis)) that are dissolved in 150 parts of water simultaneously, keeping the pH value simultaneously is 5 to 7, and the temperature maximum value is 0-5 ℃.Joining day is 30 minutes.After finishing adding, 0-5 ℃ of stirred reaction mixture 30 minutes.
In the white suspension of the II that obtains, add 34.9 parts of piperazines, stirred 30 minutes with mixture heating up to 40 ℃ and at 40 ℃.15 minute in slowly add the 16 part sodium hydroxide (100% basis) that are dissolved in 100 part water, thereby maintain the temperature at 40 ℃ thereafter.40 ℃ stir 15 minutes after, heated mixt to 95 ℃.After temperature reached 95 ℃, adding was dissolved in 16 parts of sodium hydroxide of 100 parts of second sections in the water (100% basis) in two hours.Under pressure, heat the suspension 24 hours and the final pH that obtain down and should be alkalescence at 130 ℃.At 90 ℃ of filtering suspension liquids, and be neutral up to pH with this product of hot water thorough washing.This product of 100 ℃ of dryings 24 hours, up to constant weight.Obtain the compound of 109 parts of following formulas:
N=10 wherein has following feature:
Outward appearance: white powder
Fusing point: be higher than 290 ℃
Content of organic chloride (ultimate analysis and method for hydrolysis): 1.42%.
Embodiment 2
In reactor, place 400 parts of morpholines under the room temperature with condenser, agitator and thermometer.Add the compound (comprising 1.5% chlorine) of 200 parts of formula IIIs, and heat described mixture to 120 ℃.Stirred described mixture 12 hours.After being cooled to room temperature, it is waterborne that mixture is poured over 1000 parts of 1000 parts of icing and comprising 3.5 part of 100% sodium hydroxide.The suspension that filtration obtains; At room temperature the water thorough washing is neutral up to pH.100 ℃ of dryings 24 hours, up to constant weight.Obtain the compound of 230 parts of Formula Il Ia:
N=10 wherein has following feature:
Cl content (AOX):＜0.01%
Color: white
Fusing point: be higher than 290 ℃.
Embodiment 3
In reactor, place 400 parts of piperazines under the room temperature with condenser, agitator and thermometer.Add 200 parts of compounds (comprising 1.72% chlorine) according to the formula III of United States Patent (USP) 4504610 embodiment 3 preparation, and heated mixt to 100 ℃.Stirred described mixture 12 hours.After being cooled to room temperature, it is waterborne that mixture is poured over 1000 parts of 1000 parts of icing and comprising 3.2 part of 100% sodium hydroxide.The suspension that filtration obtains; At room temperature the water thorough washing is neutral up to pH.100 ℃ of dryings 24 hours, up to constant weight.Obtain the compound of 203 parts of Formula Il Ib:
N=10 wherein has following feature:
Cl content (aox):＜0.01%
Color :=canescence
Fusing point: be higher than 290 ℃.
Embodiment 4
In reactor, under room temperature, place 4 parts of sodium hydroxide (100% basis), 0.5 part of Witco 1298 Soft Acid and 1000 parts of water with condenser, agitator and thermometer.Add the compound (comprising 1.5% chlorine) of 200 parts of formula IIIs, and heat described mixture to 98 ℃.The suspension that obtains 130 ℃ of heating 12 hours, final pH should be alkalescence.Filtering described suspension at 95 ℃, and use the hot water thorough washing, is neutral up to pH.100 ℃ of desciccates 24 hours, up to constant weight.Obtain the compound of 237 parts of Formula Il Ic
N=10 wherein has following feature:
Cl content:＜0.01%
Color: white
Fusing point: be higher than 290 ℃.
Embodiment 5
Use the 4 parts of sodium hydroxide (100% basis) among 12 parts of ammonium hydroxide (about 30%) replacement embodiment 4, and in closed reactor, react, obtain the compound of general formula III d
N=10 wherein has following feature:
Cl content:＜0.01%
Color: canescence
Fusing point: be higher than 290 ℃.
Embodiment 6
400 parts 2 ℃ water, 400 parts of trash ices and 0.5 part of Witco 1298 Soft Acid packed into have agitator, the 2-of thermometer, dropping funnel and cooling bath rises flask, adds 110.6 parts of cyanuryl chlorides subsequently in 30 minutes.Stirred the mixture 15 minutes, until obtaining uniform suspension.Exterior cooling simultaneously, and to keep pH value be between 5 to 7, temperature is-2 ℃ to+2 ℃, the 31.8 parts of yellow soda ash (100% basis) in 51.6 parts of piperidines in 200 parts of water of while charging and the 200 parts of water.Stirred described mixture 15 minutes at 2 ℃.Filter the white product that so obtains, wash with water then.Obtain 525 parts of filter cakes, its solids content is 25.5%, is equivalent to 134 parts of drying materials, corresponding to theoretical yield 96%.
After dry 10 duplicate samples under 50 ℃ of vacuum, obtain 2.55 parts of 2.6-, two chloro-4-piperidines-1,3,5-triazines (IV) (fusing point 88-88.5 ℃).
Confirm the structure of this compound by ultimate analysis and NMR.
400 parts of water and 0.1 part of Witco 1298 Soft Acid are added 1 liter of reactor that agitator, thermometer and heating bath are housed.Then 20 ℃ to wherein adding 46.6 parts of product IV and 17.2 parts of piperazines, and since thermopositive reaction elevate the temperature to 30 ℃.Heat described mixture, and stirred 1 hour at 40 ℃., under pressure be heated to 130 ℃, and kept 10 hours in this temperature thereafter.In 10 hours, add 16 parts of solid 100% sodium hydroxide continuously, and stir described mixture at 130 ℃.The product that heat filtering obtains is with boiling water thorough washing and dry.Obtain 49.2 parts of product V, yield 98%.
This product is insoluble in ordinary organic solvents and the water, and its solubility values at room temperature is lower than 0.1%.It shows and is higher than 290 ℃ fusing point, and has following general formula:
Wherein n is 10.
Embodiment 7
By using the morpholine among the piperidines replacement embodiment 2, use the compound III among the compound V replacement embodiment 2, production compound Va.It is a white powder, cl content (AOX)＜0.01%.
Embodiment 8
Use 158 parts of N, N '-two-(2,2,6,6-tetramethyl--4-piperidyl)-1,6-hexanediamine (CAS Nr:61260-56-7) replaces 34.9 parts of piperazines among the embodiment 1, obtains the general formula VI compound of white powder.
Embodiment 9
Use 4-amino-2,2,6, the 6-tetramethyl piperidine replaces the piperazine among the embodiment 3, and uses general formula VI compound to replace the compound of formula III of embodiment 3, obtains general formula VIa compound.
Embodiment 10
Use the compound of formula III among the general formula VI compound replacement embodiment 2, obtain general formula VIb compound.
Embodiment 11
Use 168.8 parts of N, N '-two-(1,2,2,6,6-pentamethyl--4-piperidyl)-1, the 6-hexanediamine replaces 34.9 parts of piperazines among the embodiment 1, obtains the general formula VII compound into white powder.
Embodiment 12
Use the compound of formula III among the general formula VII compound replacement embodiment 2, obtain general formula VIIa compound.
Embodiment 13
Use 4-amino-2,2,6, the 6-tetramethyl piperidine replaces piperazine among the embodiment 3, and uses general formula VII compound to replace the compound of formula III of embodiment 3, obtains general formula VIIb compound.
Embodiment 14
Use the morpholine among the tert-Octylamine replacement embodiment 1, obtain the product of general formula VIII with 97% yield.In the water insoluble and common organic solvent of product, and has following general formula
Wherein n is 15.
Embodiment 15
The product of use general formula VIII replaces the general formula III product among the embodiment 2, and uses the morpholine among the piperidines replacement embodiment 2, obtains general formula VIIIa product with 97% yield.In the water insoluble and common organic solvent of product, and has following general formula.
Embodiment 16
Use the piperazine among the hexamethylene-diamine replacement embodiment 6, obtain water insoluble and general formula I X product ordinary organic solvents, wherein n is 15.
Embodiment 17
By using the compound of formula III among the general formula I X compound replacement embodiment 2, obtain the product of general formula I Xa.
Can be by in Stanton Redcroft device, measuring oxygen index (according to ASTMD-2863), or by using UL-94 standard (open by " UnderwritersLaboratories " USA) mensuration self-extinguishing energy level, wherein the UL-94 standard provides the assessment to plastic material self-extinguishing energy level.
Claims (4)
1. the nitrogenous water-fast compound of halogen, its oligopolymer or polymkeric substance by the 1,3,5-triazines derivative constitutes, and has following general formula:
Wherein
Or comprising the heterocyclic group of at least one nitrogen-atoms in the ring, this group is connected to triazine ring, R by a described nitrogen-atoms
2Be alkyl or cycloalkyl, R
1It is the divalent radical of the piperazine of following general formula
Or the divalent radical of following type
N is 2 to 30 integer, comprises end value, and m is 2 to 6 integer, comprises end value, and p is 2 to 12 integer, comprise end value and
X
1=OH, NH
2Or X, wherein X and X
1Can be identical or different,
X
2=hydrogen or C
1-C
4Alkyl.
2. method of producing the described compound of Formula I of claim 1, this method is undertaken by the cyanuric halogen in two or three steps and the suitable condensation of amine and/or heterogeneous ring compound.
3. according to the purposes of the described compound of Formula I of claim 1, it is used as based on the fire retardant in the self-extinguishing polymeric composition of thermoplastic polymer.
4. self-extinguishing polymeric composition based on thermoplastic polymer, it comprises the compound of claim 1 or 4.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP08008717.4 | 2008-05-09 | ||
| EP08008717 | 2008-05-09 | ||
| EP08015381.0 | 2008-09-01 | ||
| EP08015381 | 2008-09-01 |
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| CN105440282A (en) * | 2015-12-01 | 2016-03-30 | 苏州至善化学有限公司 | 1,3,5-triazine derivative compounds with high or low polymerization degree and preparation methods |
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