CN114539739A - Preparation method of DOPO (dioctyl phthalate) and POSS (polyhedral oligomeric silsesquioxane) coordinated flame-retardant PET (polyethylene terephthalate) composite material - Google Patents
Preparation method of DOPO (dioctyl phthalate) and POSS (polyhedral oligomeric silsesquioxane) coordinated flame-retardant PET (polyethylene terephthalate) composite material Download PDFInfo
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Abstract
The invention relates to the technical field of PET flame retardance, and discloses a preparation method of a DOPO (dioctyl phthalate) synergistic POSS (polyhedral oligomeric silsesquioxane) flame-retardant PET composite material, wherein a chloridized DOPO functional monomer is obtained by carrying out addition reaction on an alkenyl functional group of allyl chloride and a phosphorus-hydrogen bond of DOPO; reacting a chlorine functional group of the chloridized DOPO functional monomer with a hydroxyl group of 4-vinylphenol to obtain an aralkenylated DOPO functional monomer; carrying out hydrosilylation reaction on an alkenyl bond of the aralkenylated DOPO functional monomer and a silicon-hydrogen bond of 8H-POSS to obtain a DOPO synergistic POSS flame retardant; and finally, the DOPO and POSS flame retardant is applied to flame-retardant polyethylene terephthalate (PET) to obtain the DOPO and POSS flame-retardant PET composite material, and the limit oxygen index of the DOPO and POSS flame-retardant PET composite material is as high as 29.4-38.6%, so that the beneficial technical effect of obviously improving the flame-retardant property of PET is achieved.
Description
Technical Field
The invention relates to the technical field of PET flame retardance, in particular to a preparation method of a DOPO (dioctyl phthalate) and POSS (polyhedral oligomeric silsesquioxane) synergistic flame-retardant PET composite material.
Background
Polyethylene terephthalate (PET) engineering plastics have the defects of fire safety, low oxygen index value of 16-20% and a large amount of smoke and molten drops generated during combustion, and are very easy to cause fire and lead to rapid spread of fire.
DOPO (9, 10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide) is prepared by reacting orthophenyl phenol and phosphorus trichloride in multiple steps. The DOPO monomer has an active hydrogen and is very easy to generate addition reaction with an unsaturated compound to generate a derivative, so that the phosphaphenanthrene structure can be very simply and quickly introduced into the compound, and the newly generated compound has excellent flame retardant property and organic solubility.
POSS can be used as a stand-alone flame retardant or as an important synergistic flame retardant for modification, producing a surprising effect on flame retardancy of polymers. In recent years, many researchers have introduced POSS into materials for flame retardant modification studies.
The present invention incorporates the following references: a doctor's academic paper of Zhejiang university, namely preparation and performance research of functionalized cage-type oligomeric silsesquioxane and application of functionalized cage-type oligomeric silsesquioxane in hybrid materials, discloses a structure and a preparation method of cage-type octa (dimethylsiloxy) silsesquioxane (8H-POSS).
The application tries to synthesize the DOPO synergistic POSS flame-retardant PET composite material with excellent flame-retardant performance.
Disclosure of Invention
Technical problem to be solved
The invention aims to provide a preparation method of a DOPO (dioctyl phthalate) synergistic POSS (polyhedral oligomeric silsesquioxane) flame-retardant PET composite material with excellent flame retardant property.
(II) technical scheme
In order to achieve the purpose, the invention provides the following technical scheme:
a preparation method of a DOPO synergistic POSS flame-retardant PET composite material comprises the following steps:
step S1, synthesis of chloridized DOPO functional monomer:
adding 5-15 parts of allyl chloride and 8-25 parts of 9, 10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxa (DOPO) into a three-neck flask with a stirring device, uniformly stirring, adding azobisisobutyronitrile, slowly heating to 50-90 ℃, and reacting for 4-15 hours to obtain a chloro-DOPO functional monomer;
step S2, synthesis of aralkenylated DOPO functional monomer:
adding 10-35 parts of 4-vinylphenol and absolute ethyl alcohol into a four-neck flask provided with a mechanical stirring and reflux condensing tube, keeping the stirring speed constant at 300r/min, heating until the mixture is completely dissolved, and adding 5-20 parts of chloridized DOPO functional monomer from a constant-pressure funnel; adding nano potassium carbonate into the flask, and continuously heating for reaction to obtain an aralkylated DOPO functional monomer;
step S3, synthesizing the DOPO synergistic POSS flame retardant:
pouring 1-10 parts of aralkenylated DOPO functional monomer into a three-neck flask with xylene, then adding 10-30 parts of cage octa (dimethylsiloxy) silsesquioxane (8H-POSS), continuously stirring for 5min, and uniformly mixing; then, dropwise adding a chloroplatinic acid catalyst into the mixed solution, stirring and refluxing for 10-60min at the temperature of 30-60 ℃, and carrying out the whole process under the protection of nitrogen to obtain the DOPO synergistic POSS flame retardant;
step S4, preparing the DOPO cooperated POSS flame-retardant PET composite material:
100 parts of polyethylene terephthalate and 3-15 parts of DOPO synergistic POSS flame retardant are stirred and mixed uniformly, extruded and granulated on a miniature conical double-screw extruder, and the prepared granules are injected and molded into standard sample strips of the DOPO synergistic POSS flame-retardant PET composite material required by measurement on a miniature injection molding machine.
Preferably, the step S1: the dosage of the azodiisobutyronitrile is 0.05 to 0.6 portion.
Preferably, the step S2: adding 10-35 parts of nano potassium carbonate into the flask, continuously heating to 40-80 ℃, and reacting for 2-10h to obtain the aralkylated DOPO functional monomer.
Preferably, the step S3: the dosage of the chloroplatinic acid catalyst is 0.1-0.6 part.
(III) advantageous technical effects
Compared with the prior art, the invention has the following beneficial technical effects:
firstly, carrying out addition reaction on an alkenyl functional group of allyl chloride and a phosphorus-hydrogen bond of 9, 10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide (DOPO) to obtain a chloridized DOPO functional monomer;
reacting a chlorine functional group of the chloridized DOPO functional monomer with a hydroxyl group of 4-vinylphenol to obtain an aryleneated DOPO functional monomer;
the alkenyl bond of the aralkenylated DOPO functional monomer and the silicon-hydrogen bond of cage octa poly (dimethylsiloxy) silsesquioxane (8H-POSS) generate hydrosilylation reaction to obtain the DOPO synergistic POSS flame retardant;
and finally, applying the DOPO and POSS flame retardant to flame-retardant polyethylene terephthalate (PET) to obtain the DOPO and POSS flame-retardant PET composite material, wherein the limit oxygen index of the DOPO and POSS flame-retardant PET composite material is as high as 29.4-38.6%, so that the invention has the beneficial technical effect of obviously improving the flame-retardant property of PET.
Detailed Description
Example 1:
a preparation method of a DOPO synergistic POSS flame-retardant PET composite material comprises the following steps:
step S1, synthesis of chloridized DOPO functional monomer:
adding 10g of allyl chloride and 14g of 9, 10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxa (DOPO) into a 100mL three-neck flask with a stirring device, uniformly stirring, adding 0.5g of Azobisisobutyronitrile (AIBN), slowly heating to 80 ℃, and reacting for 10 hours to obtain a chloridized DOPO functional monomer;
step S2, synthesizing an aralkenylated DOPO functional monomer:
adding 18g of 4-vinylphenol and 80mL of absolute ethyl alcohol into a 250mL four-neck flask provided with a mechanical stirring and reflux condensing tube (provided with a drying tube), heating until the mixture is completely dissolved at a constant stirring speed of 300r/min, and adding 12g of chloro-DOPO functional monomer from a constant pressure funnel; adding 18g of nano potassium carbonate into the flask, continuously heating to 60 ℃, and reacting for 6 hours; cooling to room temperature, filtering, recovering a filter cake, concentrating the filtrate, adding 15mL of ethanol/dichloromethane (volume ratio is 1:1) mixed solvent, stirring until the mixture is completely dissolved, standing at 0 ℃ for 12h, filtering, washing with a small amount of cold absolute ethanol, and drying in vacuum to obtain the arylalkenyl DOPO functional monomer;
step S3, synthesizing the DOPO synergistic POSS flame retardant:
pouring 6g of aralkenyl DOPO functional monomer into a three-neck flask with 150mL of dimethylbenzene, then adding 14g of cage octa (dimethylsiloxy) silsesquioxane (8H-POSS), continuing stirring for 5min, and uniformly mixing; then 0.4g of chloroplatinic acid catalyst is dripped into the mixed solution, and the mixed solution is stirred and refluxed for 20min at the temperature of 40 ℃; the whole process is carried out under the protection of nitrogen, finally the well-refluxed reaction system is vacuumized for 1h, xylene in the system is removed, and the DOPO synergistic POSS flame retardant is obtained;
step S4, preparing the DOPO cooperated POSS flame-retardant PET composite material:
100g of polyethylene terephthalate and 6g of DOPO synergistic POSS flame retardant are uniformly stirred and mixed, extruded and granulated on a miniature conical double-screw extruder, the temperature of a first machine barrel is 220 ℃, the temperature of a second machine barrel is 220 ℃, the prepared granules are injected and molded into a standard sample strip of the DOPO synergistic POSS flame-retardant PET composite material required by measurement on a miniature injection molding machine, the injection pressure is 0.5MPa, the temperature of a melting furnace is 210 ℃, and the temperature of a die is 50 ℃.
Example 2:
a preparation method of a DOPO synergistic POSS flame-retardant PET composite material comprises the following steps:
step S1, synthesis of chloridized DOPO functional monomer:
adding 5g of allyl chloride and 8g of 9, 10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxa (DOPO) into a 100mL three-neck flask with a stirring device, uniformly stirring, adding 0.05g of Azobisisobutyronitrile (AIBN), slowly heating to 50 ℃ and reacting for 4 hours to obtain a chloridized DOPO functional monomer;
step S2, synthesizing an aralkenylated DOPO functional monomer:
adding 10g of 4-vinylphenol and 80mL of absolute ethyl alcohol into a 250mL four-neck flask provided with a mechanical stirring and reflux condensing tube (provided with a drying tube), heating until the mixture is completely dissolved at a constant stirring speed of 300r/min, and adding 5g of chloro-DOPO functional monomer from a constant pressure funnel; adding 10g of nano potassium carbonate into the flask, continuously heating to 40 ℃, and reacting for 10 hours; cooling to room temperature, filtering, recovering a filter cake, concentrating the filtrate, adding 15mL of ethanol/dichloromethane (volume ratio is 1:1) mixed solvent, stirring until the mixture is completely dissolved, standing at 0 ℃ for 12h, filtering, washing with a small amount of cold absolute ethanol, and drying in vacuum to obtain the arylalkenyl DOPO functional monomer;
step S3, synthesizing the DOPO synergistic POSS flame retardant:
pouring 1g of aralkenyl DOPO functional monomer into a three-neck flask with 150mL of dimethylbenzene, then adding 10g of cage octa (dimethylsiloxy) silsesquioxane (8H-POSS), continuing stirring for 5min, and uniformly mixing; then 0.1g of chloroplatinic acid catalyst is dripped into the mixed solution, and the mixed solution is stirred and refluxed for 60min at the temperature of 30 ℃; the whole process is carried out under the protection of nitrogen, finally the well-refluxed reaction system is vacuumized for 1h, xylene in the system is removed, and the DOPO synergistic POSS flame retardant is obtained;
step S4, preparing the DOPO cooperated POSS flame-retardant PET composite material:
100g of polyethylene terephthalate and 3g of DOPO synergistic POSS flame retardant are uniformly stirred and mixed, and are extruded and granulated on a miniature conical double-screw extruder, wherein the temperature of a first machine barrel is 180 ℃, the temperature of a second machine barrel is 180 ℃, the prepared granules are injected and molded into a standard sample strip of the DOPO synergistic POSS flame-retardant PET composite material required by measurement on a miniature injection molding machine, the injection pressure is 0.5MPa, the temperature of a melting furnace is 180 ℃, and the temperature of a die is 40 ℃.
Example 3:
a preparation method of a DOPO synergistic POSS flame-retardant PET composite material comprises the following steps:
step S1, synthesis of chloridized DOPO functional monomer:
adding 15g of allyl chloride and 25g of 9, 10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxa (DOPO) into a 100mL three-neck flask with a stirring device, uniformly stirring, adding 0.6g of Azobisisobutyronitrile (AIBN), slowly heating to 90 ℃ and reacting for 15h to obtain a chloridized DOPO functional monomer;
step S2, synthesizing an aralkenylated DOPO functional monomer:
adding 35g of 4-vinylphenol and 80mL of absolute ethyl alcohol into a 250mL four-neck flask provided with a mechanical stirring and reflux condensing tube (provided with a drying tube), heating until the mixture is completely dissolved at a constant stirring speed of 300r/min, and adding 20g of chloro-DOPO functional monomer from a constant pressure funnel; adding 35g of nano potassium carbonate into the flask, continuously heating to 80 ℃, and reacting for 2 hours; cooling to room temperature, filtering, recovering a filter cake, concentrating the filtrate, adding 15mL of ethanol/dichloromethane (volume ratio is 1:1) mixed solvent, stirring until the mixture is completely dissolved, standing at 0 ℃ for 12h, filtering, washing with a small amount of cold absolute ethanol, and drying in vacuum to obtain the arylalkenyl DOPO functional monomer;
step S3, synthesizing the DOPO synergistic POSS flame retardant:
pouring 10g of aralkenyl DOPO functional monomer into a three-neck flask with 150mL of dimethylbenzene, then adding 30g of cage octa (dimethylsiloxy) silsesquioxane (8H-POSS), continuing stirring for 5min, and uniformly mixing; then 0.6g of chloroplatinic acid catalyst is dripped into the mixed solution, and the mixed solution is stirred and refluxed for 10min at the temperature of 60 ℃; the whole process is carried out under the protection of nitrogen, finally the well-refluxed reaction system is vacuumized for 1h, xylene in the system is removed, and the DOPO synergistic POSS flame retardant is obtained;
step S4, preparing the DOPO cooperated POSS flame-retardant PET composite material:
100g of polyethylene terephthalate and 15g of DOPO synergistic POSS flame retardant are uniformly stirred and mixed, extruded and granulated on a miniature conical double-screw extruder, the temperature of a first machine barrel is 250 ℃, the temperature of a second machine barrel is 250 ℃, the prepared granules are injected and molded into a standard sample strip of the DOPO synergistic POSS flame-retardant PET composite material required by measurement on a miniature injection molding machine, the injection pressure is 0.5MPa, the temperature of a melting furnace is 250 ℃, and the temperature of a die is 60 ℃.
Comparative example 1:
a preparation method of a flame-retardant PET composite material comprises the following steps:
100g of polyethylene terephthalate, 14g of 9, 10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxa (DOPO) and 14g of cage octa (dimethylsiloxy) silsesquioxane (8H-POSS) are uniformly stirred and mixed, extruded and granulated on a miniature conical double-screw extruder, the temperature of a first machine barrel is 220 ℃, the temperature of a second machine barrel is 220 ℃, the prepared granules are injection-molded into a standard sample strip of the flame-retardant PET composite material required by measurement on a miniature injection molding machine, the injection pressure is 0.5MPa, the temperature of a melting furnace is 210 ℃, and the temperature of the mold is 50 ℃.
Comparative example 2:
a preparation method of a flame-retardant PET composite material comprises the following steps:
100g of polyethylene terephthalate and 14g of cage octa (dimethylsiloxy) silsesquioxane (8H-POSS) are uniformly stirred and mixed, extruded and granulated on a miniature conical double-screw extruder, the temperature of a first cylinder is 220 ℃, the temperature of a second cylinder is 220 ℃, the prepared granules are injection-molded on a miniature injection molding machine to form a standard sample strip of the flame-retardant PET composite material required by measurement, the injection pressure is 0.5MPa, the temperature of a melting furnace is 210 ℃, and the temperature of a mold is 50 ℃.
Comparative example 3:
a preparation method of a flame-retardant PET composite material comprises the following steps:
100g of polyethylene terephthalate and 14g of 9, 10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxa (DOPO) are stirred and mixed uniformly, extruded and granulated on a miniature conical double-screw extruder, the temperature of a first machine barrel is 220 ℃, the temperature of a second machine barrel is 220 ℃, the prepared granules are injection-molded into a standard sample strip of the flame-retardant PET composite material required by measurement on a miniature injection molding machine, the injection pressure is 0.5MPa, the temperature of a melting furnace is 210 ℃, and the temperature of a mold is 50 ℃.
And (3) performance measurement:
firstly, the limiting oxygen index is tested according to GB/T2406-1993, the sample size is 130mm multiplied by 6.0mm multiplied by 3.0mm, and the test result is shown in Table 1;
TABLE 1
Sample numbering | Limiting oxygen index/%) |
Example 1 | 38.6 |
Example 2 | 29.4 |
Example 3 | 35.1 |
Comparative example 1 | 25.4 |
Comparative example 2 | 21.7 |
Comparative example 3 | 24.0 |
As can be seen from Table 1, the limiting oxygen index of the flame-retardant PET composite material added with DOPO in cooperation with the MOSS-12 flame retardant is significantly higher than that of the flame-retardant PET composite material of the comparative example.
Claims (4)
1. A preparation method of a DOPO (dioctyl phthalate) cooperated POSS (polyhedral oligomeric silsesquioxane) flame-retardant PET composite material is characterized by comprising the following steps:
step S1, synthesis of chloridized DOPO functional monomer:
adding 5-15 parts of allyl chloride and 8-25 parts of 9, 10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxa (DOPO) into a three-neck flask with a stirring device, uniformly stirring, adding azobisisobutyronitrile, slowly heating to 50-90 ℃, and reacting for 4-15 hours to obtain a chloro-DOPO functional monomer;
step S2, synthesizing an aralkenylated DOPO functional monomer:
adding 10-35 parts of 4-vinylphenol and absolute ethyl alcohol into a four-neck flask provided with a mechanical stirring and reflux condensing tube, keeping the stirring speed constant at 300r/min, heating until the mixture is completely dissolved, and adding 5-20 parts of chloro-DOPO functional monomer from a constant-pressure funnel; adding nano potassium carbonate into the flask, and continuously heating for reaction to obtain an aralkylated DOPO functional monomer;
step S3, synthesizing the DOPO synergistic POSS flame retardant:
pouring 1-10 parts of aralkenylated DOPO functional monomer into a three-neck flask with xylene, then adding 10-30 parts of cage octa (dimethylsiloxy) silsesquioxane (8H-POSS), continuously stirring for 5min, and uniformly mixing; then, dropwise adding a chloroplatinic acid catalyst into the mixed solution, stirring and refluxing for 10-60min at the temperature of 30-60 ℃, and carrying out the whole process under the protection of nitrogen to obtain the DOPO synergistic POSS flame retardant;
step S4, preparing the DOPO cooperated POSS flame-retardant PET composite material:
100 parts of polyethylene terephthalate and 3-15 parts of DOPO synergistic POSS flame retardant are stirred and mixed uniformly, extruded and granulated on a miniature conical double-screw extruder, and the prepared granules are injected and molded into standard sample strips of the DOPO synergistic POSS flame-retardant PET composite material required by measurement on a miniature injection molding machine.
2. The preparation method of the DOPO cooperated POSS flame retardant PET composite material as claimed in claim 1, wherein the step S1: the dosage of the azodiisobutyronitrile is 0.05 to 0.6 portion.
3. The preparation method of the DOPO cooperated POSS flame retardant PET composite material as claimed in claim 1, wherein the step S2: adding 10-35 parts of nano potassium carbonate into the flask, continuously heating to 40-80 ℃, and reacting for 2-10h to obtain the aralkylated DOPO functional monomer.
4. The preparation method of the DOPO cooperated POSS flame retardant PET composite material as claimed in claim 1, wherein the step S3: the dosage of the chloroplatinic acid catalyst is 0.1-0.6 part.
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