CN101709111A - Poly-p-phenylene ethene diamine/hexamethylene diamine copolymer and preparation method thereof - Google Patents
Poly-p-phenylene ethene diamine/hexamethylene diamine copolymer and preparation method thereof Download PDFInfo
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- CN101709111A CN101709111A CN200910263550A CN200910263550A CN101709111A CN 101709111 A CN101709111 A CN 101709111A CN 200910263550 A CN200910263550 A CN 200910263550A CN 200910263550 A CN200910263550 A CN 200910263550A CN 101709111 A CN101709111 A CN 101709111A
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Abstract
The invention relates to a poly-p-phenylene ethene diamine/hexamethylene diamine copolymer and a preparation method thereof, which is characterized by comprising the following steps of: dissolving 20.3 parts of paraphthaloyl chloride and 1-30 parts of auxiliary agent in 100-1000 parts of organic solvent to prepare into acyl chloride solution; adding 0.3-5.7 parts of 1,2- ethene diamine, 0.58-11.02 parts of 1,6-ethene diamine, 8-13.8 parts of alkaline compound and 800-1200 parts of deionized water into a reactor with a stirrer, a thermometer and a reflux condenser to be completely dissolved; under the cooling of a cooling bath, adding the prepared acyl chloride solution slowly into the reactor within 0.5-2 hours and then stirring and reacting for 1-3 hours; adding 100-1000 parts of deionized water; distilling and recycling solvent at the 30-90 DEG C; centrifugating and separating reactive mixture; concentrating and crystallizing the liquid to obtain by-product salt; washing ,purifying by using acetone and drying the solid to obtain the poly-p-phenylene ethene diamine/hexamethylene diamine copolymer. The intrinsic viscosity[Eta]of the copolymer is equal to 0.30-0.80dL*g-1, the melting point Tm is 340-380 DEG C, and the initial thermal decomposition temperature Td is 390-440 DEG C.
Description
Technical field
The present invention relates to a kind of poly-paraphenylene terephthalamide's quadrol/hexanediamine multipolymer and preparation method thereof, belong to the Polymer Synthesizing field.
Background technology
Molecular backbone chain contains the semi-aromatic polyamide of aryl and aliphatic chain, has good thermotolerance and processing characteristics concurrently, is the engineering plastics of a class excellent property.In terephthalic acid and derivative thereof and the aliphatie diamine synthetic series semi-aromatic polyamide, along with carbonatoms in two amine molecules reduces, the polymkeric substance thermal characteristics improves, but the processibility variation.Poly-hexamethylene terephthalamide (PA6T) and poly-paraphenylene terephthalamide's nonamethylene diamine (PA9T) can melt-processed, and fusing point is higher than 300 ℃, and gathering paraphenylene terephthalamide's quadrol (PA2T) and poly-paraphenylene terephthalamide's butanediamine (PA4T) then can not melt-processed.In the semi-aromatic polyamide multipolymer, containing the few multipolymer of paraphenylene terephthalamide's quadrol (2T) and paraphenylene terephthalamide's butanediamine (4T) structural unit can melt-processed, and the content height then can not fusion.
U.S. Pat 2002183479A1 has reported with terephthalic acid butanediamine salt, terephthalic acid hexanediamine salt and water and generated prepolymer under high temperature, high pressure, under high temperature, vacuum, carry out the synthetic poly-paraphenylene terephthalamide's butanediamine of solid phase polycondensation/hexanediamine multipolymer (PA4T/6T) again, this melting point polymer is higher than 300 ℃, but desired raw material 1,4-butanediamine cost height, source are few, and pre-polymerization and solid phase polycondensation are to the equipment requirements height.U.S. Pat 4072664A has reported with 1,2-quadrol and paranitrobenzoyl chloride reaction obtain dinitro compound, make the aromatic diamines that contains the quadrol structure through reduction reaction, and press different ratios and mix with Ursol D, again with p-phthaloyl chloride prepared in reaction poly P phenylene diamine terephthalamide multipolymer, the fiber of this polymkeric substance has mechanical property preferably, but synthesis technique complexity, cost height.The Chang Jing of Zhejiang University, Feng Lianfang etc. obtain full-bodied PA6T with the polycondensation in ionic liquid of terephthalic acid hexanediamine salt, but ionic liquid cost height is recycled the back deleterious.
Summary of the invention
The objective of the invention is provides a kind of poly-paraphenylene terephthalamide's quadrol/hexanediamine multipolymer and preparation method thereof at the deficiencies in the prior art, be characterized in p-phthaloyl chloride, 1,2-quadrol and 1, the 6-hexanediamine is a raw material, and the method by interfacial polycondensation prepares poly-paraphenylene terephthalamide's quadrol/hexanediamine multipolymer under room temperature, normal pressure.By regulating 1 and 1, the proportioning of 6-hexanediamine obtains the different poly-paraphenylene terephthalamide's quadrol/hexanediamine multipolymer of paraphenylene terephthalamide's quadrol structural unit content.
Purpose of the present invention is realized that by following technical measures wherein said raw material umber is parts by weight except that specified otherwise.
Solvent 100-1000 part
20.3 parts of p-phthaloyl chlorides
Auxiliary agent 1-30 part
1 0.3-5.7 part
1,6-hexanediamine 0.58-11.02 part
Basic cpd 8-13.8 part
Deionized water 80-1200 part is used in reaction
Deionized water 100-1000 part is used in distillation
And by the preparation of following processing step and processing parameter:
P-phthaloyl chloride in the said components and auxiliary agent are dissolved in solvent are made into solution of acid chloride; With 1,1,6-hexanediamine, basic cpd and reaction add with deionized water and have in the reactor of agitator, thermometer and reflux exchanger, and solid is dissolved fully; Under the cooling bath cooling, the above-mentioned solution of acid chloride for preparing was slowly added in 0.5-2 hour in the reactor, restir reaction 1-3 hour obtains poly-paraphenylene terephthalamide's quadrol/hexanediamine multipolymer, and its chemical structural formula is:
X=0.05-0.95 wherein, n=2-200.
Solvent is at least a in pentane, hexane, hexanaphthene, I class sherwood oil, II class sherwood oil and the methylene dichloride.
Auxiliary agent is N, in dinethylformamide, N,N-dimethylacetamide, dimethyl sulfoxide (DMSO) or the N-Methyl pyrrolidone any.
Basic cpd be in yellow soda ash, salt of wormwood, sodium hydroxide or the potassium hydroxide any.
The preparation method of poly-paraphenylene terephthalamide's quadrol/hexanediamine multipolymer may further comprise the steps:
(1) preparation of solution of acid chloride
P-phthaloyl chloride is dissolved in solvent 100-1000 part with auxiliary agent 1-30 part for 20.3 parts is made into solution of acid chloride;
(2) preparation of poly-paraphenylene terephthalamide's quadrol/hexanediamine multipolymer
With 1 0.3-5.7 part, 1, have in the reactor of agitator, thermometer and reflux exchanger the addings of 6-hexanediamine 0.58-11.02 part, basic cpd 8-13.8 part and deionized water 80-1200 part, and solid is dissolved fully; Under the cooling bath cooling, the above-mentioned solution of acid chloride for preparing was slowly added in 0.5-2 hour in the reactor, restir reaction 1-3 hour obtains poly-paraphenylene terephthalamide's quadrol/hexanediamine multipolymer;
(3) solvent recuperation, the by product purification of collecting and gathering paraphenylene terephthalamide's quadrol/hexanediamine multipolymer
Deionized water 100-1000 part is added reactor, distillation between temperature 30-90 ℃, recovery solvent; The centrifugation reaction mixture, liquid obtains by-product salt through concentrated, crystallization, and solid obtains pure poly-paraphenylene terephthalamide's quadrol/hexanediamine multipolymer through washing, acetone purification, drying.
Performance test:
The structure of poly-paraphenylene terephthalamide's quadrol/hexanediamine multipolymer is confirmed through examination of infrared spectrum, and as shown in Figure 1, the result shows: 3323cm
-1, 1634cm
-1And 1546cm
-1Be amido linkage absorption peak, 1495cm
-1And 864cm
-1Be the phenyl ring absorption peak.
By regulating 1 and 1, the proportioning of 6-hexanediamine obtains the different poly-paraphenylene terephthalamide's quadrol/hexanediamine multipolymer of paraphenylene terephthalamide's quadrol structural unit content.With the vitriol oil is solvent, preparation 0.5gdL
-1Sample liquid, use down Ubbelohde viscometers at 30.0 ± 0.1 ℃, adopt the intrinsic viscosity of dilution method mensuration polymkeric substance, its intrinsic viscosity [η]=0.30-0.80dLg
-1
Differential scanning calorimetry adopts the NETZSCH DSC 200PC of company, 10 ℃ of min of temperature rise rate
-1, nitrogen atmosphere, Range of measuring temp: 200-400 ℃, test result as shown in Figure 2, its fusing point is 340-380 ℃; TA company's T GA Q500,10 ℃ of min of temperature rise rate are adopted in thermogravimetric analysis
-1, nitrogen atmosphere, Range of measuring temp: 100-600 ℃, test result as shown in Figure 3, its initial heat decomposition temperature is 390-440 ℃.
The present invention has following advantage:
1. the present invention adopts the method for interfacial polycondensation, has advantage simple to operate.
2. interfacial polycondensation is reflected under room temperature, the normal pressure and carries out, and has energy-saving advantages.
3. the requirement of interfacial polycondensation reaction pair monomer ratio is low, and it is fast to have speed of reaction, the advantage that side reaction is few.
4. the preparation method of poly-paraphenylene terephthalamide's quadrol/hexanediamine multipolymer, the solvent price is low, murder by poisoning is low, the rate of recovery is high, has the advantage of economy, environmental protection.
5. the preparation method of poly-paraphenylene terephthalamide's quadrol/hexanediamine multipolymer, experimental repeatability is good, process stabilizing, product yield height.
6. poly-paraphenylene terephthalamide's quadrol/hexanediamine multipolymer fusing point height belongs to resistant to elevated temperatures novel high polymer material.
Description of drawings
Fig. 1 is the infrared spectrogram of poly-paraphenylene terephthalamide's quadrol/hexanediamine multipolymer
*
Fig. 2 is the differential scanning calorimetry figure of poly-paraphenylene terephthalamide's quadrol/hexanediamine multipolymer
*
Fig. 3 is the thermogravimetric analysis figure of poly-paraphenylene terephthalamide's quadrol/hexanediamine multipolymer
*
*Wherein poly-paraphenylene terephthalamide's quadrol/hexanediamine multipolymer chemical structural formula be:
Embodiment
Below by embodiment the present invention is carried out concrete description, be necessary to be pointed out that at this present embodiment only is used for the present invention is further specified, can not be interpreted as the restriction to the scope of the present invention includes, the person skilled in the art in this field can make some nonessential improvement and adjustment according to the content of the invention described above.
Embodiment 2,20.3g p-phthaloyl chloride and 20g N,N-dimethylacetamide are dissolved in the 600g pentane are made into solution of acid chloride; With 0.3g 1,11.02g 1,6-hexanediamine, 13.8g salt of wormwood and 500g deionized water add and have in the reactor of agitator, thermometer and reflux exchanger, and solid is dissolved fully; Under the cooling bath cooling, the above-mentioned solution of acid chloride for preparing was slowly added in the reactor restir reaction 2 hours in 1 hour; Add the 600g deionized water, distillation between temperature 30-60 ℃, recovery solvent; The centrifugation reaction mixture, liquid obtains by-product salt through concentrated, crystallization, and solid obtains to gather paraphenylene terephthalamide's quadrol/hexanediamine multipolymer, productive rate 91%, intrinsic viscosity [η]=0.38dLg through washing, acetone purification, drying
-1
Embodiment 3,20.3g p-phthaloyl chloride and 1g dimethyl sulfoxide (DMSO) are dissolved in the 100g methylene dichloride are made into solution of acid chloride; With 1.2g 1,9.28g 1,6-hexanediamine, 8g sodium hydroxide and 100g deionized water add and have in the reactor of agitator, thermometer and reflux exchanger, and solid is dissolved fully; Under the cooling bath cooling, the above-mentioned solution of acid chloride for preparing was slowly added in the reactor restir reaction 1 hour in 0.5 hour; Add the 100g deionized water, distillation between temperature 30-60 ℃, recovery solvent; The centrifugation reaction mixture, liquid obtains by-product salt through concentrated, crystallization, and solid obtains to gather paraphenylene terephthalamide's quadrol/hexanediamine multipolymer, productive rate 83%, intrinsic viscosity [η]=0.58dLg through washing, acetone purification, drying
-1
Embodiment 4,20.3g p-phthaloyl chloride and 10g N-Methyl pyrrolidone are dissolved in the 150g hexanaphthene are made into solution of acid chloride; With 5.4g 1,1.16g 1,6-hexanediamine, 8g sodium hydroxide and 150g deionized water add and have in the reactor of agitator, thermometer and reflux exchanger, and solid is dissolved fully; Under the cooling bath cooling, the above-mentioned solution of acid chloride for preparing was slowly added in the reactor restir reaction 2 hours in 1 hour; Add the 150g deionized water, distillation between temperature 60-90 ℃, recovery solvent; The centrifugation reaction mixture, liquid obtains by-product salt through concentrated, crystallization, and solid obtains to gather paraphenylene terephthalamide's quadrol/hexanediamine multipolymer, productive rate 87%, intrinsic viscosity [η]=0.72dLg through washing, acetone purification, drying
-1
Embodiment 5,20.3g p-phthaloyl chloride and 10g N-Methyl pyrrolidone are dissolved in 100g I class sherwood oil are made into solution of acid chloride; With 2.4g 1,6.96g 1,6-hexanediamine, 11.2g potassium hydroxide and 80g deionized water add and have in the reactor of agitator, thermometer and reflux exchanger, and solid is dissolved fully; Under the cooling bath cooling, the above-mentioned solution of acid chloride for preparing was slowly added in the reactor restir reaction 3 hours in 0.5 hour; Add the 100g deionized water, distillation between temperature 30-60 ℃, recovery solvent; The centrifugation reaction mixture, liquid obtains by-product salt through concentrated, crystallization, and solid obtains to gather paraphenylene terephthalamide's quadrol/hexanediamine multipolymer, productive rate 81%, intrinsic viscosity [η]=0.65dLg through washing, acetone purification, drying
-1
Embodiment 6,20.3g p-phthaloyl chloride and 30g N,N-dimethylacetamide are dissolved in 1000g II class sherwood oil are made into solution of acid chloride; With 5.7g 1,0.58g 1,6-hexanediamine, 11.2g potassium hydroxide and 1200g deionized water add and have in the reactor of agitator, thermometer and reflux exchanger, and solid is dissolved fully; Under the cooling bath cooling, the above-mentioned solution of acid chloride for preparing was slowly added in the reactor restir reaction 3 hours in 2 hours; Add the 1000g deionized water, distillation between temperature 60-90 ℃, recovery solvent; The centrifugation reaction mixture, liquid obtains by-product salt through concentrated, crystallization, and solid obtains to gather paraphenylene terephthalamide's quadrol/hexanediamine multipolymer, productive rate 89%, intrinsic viscosity [η]=0.46dLg through washing, acetone purification, drying
-1
Embodiment 7,20.3g p-phthaloyl chloride and 25g N,N-dimethylacetamide are dissolved in the mixed solvent of being made up of 200g pentane and 300g hexane are made into solution of acid chloride; With 3.6g 1,4.64g 1,6-hexanediamine, 8g sodium hydroxide and 500g deionized water add and have in the reactor of agitator, thermometer and reflux exchanger, and solid is dissolved fully; Under the cooling bath cooling, the above-mentioned solution of acid chloride for preparing was slowly added in the reactor restir reaction 2 hours in 1 hour; Add the 500g deionized water, distillation between temperature 30-90 ℃, recovery solvent; The centrifugation reaction mixture, liquid obtains by-product salt through concentrated, crystallization, and solid obtains to gather paraphenylene terephthalamide's quadrol/hexanediamine multipolymer, productive rate 92%, intrinsic viscosity [η]=0.51dLg through washing, acetone purification, drying
-1
Embodiment 8,20.3g p-phthaloyl chloride and 10g N-Methyl pyrrolidone are dissolved in the mixed solvent of being made up of 700g hexane and 200g hexanaphthene are made into solution of acid chloride; With 2.4g 1,6.96g 1,6-hexanediamine, 13.8g salt of wormwood and 800g deionized water add and have in the reactor of agitator, thermometer and reflux exchanger, and solid is dissolved fully; Under the cooling bath cooling, the above-mentioned solution of acid chloride for preparing was slowly added in the reactor restir reaction 3 hours in 2 hours; Add the 900g deionized water, distillation between temperature 60-90 ℃, recovery solvent; The centrifugation reaction mixture, liquid obtains by-product salt through concentrated, crystallization, and solid obtains to gather paraphenylene terephthalamide's quadrol/hexanediamine multipolymer, productive rate 93%, intrinsic viscosity [η]=0.75dLg through washing, acetone purification, drying
-1
Embodiment 9,20.3g p-phthaloyl chloride and 20g dimethyl sulfoxide (DMSO) are dissolved in the mixed solvent of being made up of 350g I class sherwood oil and 50g II class sherwood oil are made into solution of acid chloride; With 1.5g 1,8.7g 1,6-hexanediamine, 8g sodium hydroxide and 400g deionized water add and have in the reactor of agitator, thermometer and reflux exchanger, and solid is dissolved fully; Under the cooling bath cooling, the above-mentioned solution of acid chloride for preparing was slowly added in the reactor restir reaction 2 hours in 1 hour; Add the 400g deionized water, distillation between temperature 30-90 ℃, recovery solvent; The centrifugation reaction mixture, liquid obtains by-product salt through concentrated, crystallization, and solid obtains to gather paraphenylene terephthalamide's quadrol/hexanediamine multipolymer, productive rate 94%, intrinsic viscosity [η]=0.58dLg through washing, acetone purification, drying
-1
Embodiment 10, with 20.3g p-phthaloyl chloride and 5g N, dinethylformamide is dissolved in the mixed solvent of being made up of 550g methylene dichloride and 50g hexanaphthene and is made into solution of acid chloride; With 1.8g 1,8.12g 1,6-hexanediamine, 11.2g potassium hydroxide and 500g deionized water add and have in the reactor of agitator, thermometer and reflux exchanger, and solid is dissolved fully; Under the cooling bath cooling, the above-mentioned solution of acid chloride for preparing was slowly added in the reactor restir reaction 2 hours in 1 hour; Add the 600g deionized water, distillation between temperature 30-90 ℃, recovery solvent; The centrifugation reaction mixture, liquid obtains by-product salt through concentrated, crystallization, and solid obtains to gather paraphenylene terephthalamide's quadrol/hexanediamine multipolymer, productive rate 93%, intrinsic viscosity [η]=0.66dLg through washing, acetone purification, drying
-1
Embodiment 11,203g p-phthaloyl chloride and 200g N,N-dimethylacetamide are dissolved in 3000g I class sherwood oil are made into solution of acid chloride; With 30g 1,58g 1,6-hexanediamine, 112g potassium hydroxide and 3500g deionized water add and have in the reactor of agitator, thermometer and reflux exchanger, and solid is dissolved fully; Under the cooling bath cooling, the above-mentioned solution of acid chloride for preparing was slowly added in the reactor restir reaction 2 hours in 2 hours; Add the 3000g deionized water, distillation between temperature 30-60 ℃, recovery solvent; The centrifugation reaction mixture, liquid obtains by-product salt through concentrated, crystallization, and solid obtains to gather paraphenylene terephthalamide's quadrol/hexanediamine multipolymer, productive rate 89%, intrinsic viscosity [η]=0.63dLg through washing, acetone purification, drying
-1
Claims (5)
1. poly-paraphenylene terephthalamide's quadrol/hexanediamine multipolymer is characterized in that the raw material of this multipolymer is composed of the following components, is by weight:
Solvent 100-1000 part
20.3 parts of p-phthaloyl chlorides
Auxiliary agent 1-30 part
1 0.3-5.7 part
1,6-hexanediamine 0.58-11.02 part
Basic cpd 8-13.8 part
Deionized water 80-1200 part is used in reaction
Deionized water 100-1000 part is used in distillation
And by the preparation of following processing step and processing parameter:
P-phthaloyl chloride in the said components and auxiliary agent are dissolved in solvent are made into solution of acid chloride; With 1,1,6-hexanediamine, basic cpd and reaction add with deionized water and have in the reactor of agitator, thermometer and reflux exchanger, and solid is dissolved fully; Under the cooling bath cooling, the above-mentioned solution of acid chloride for preparing was slowly added in 0.5-2 hour in the reactor, restir reaction 1-3 hour obtains poly-paraphenylene terephthalamide's quadrol/hexanediamine multipolymer, and its chemical structural formula is:
X=0.05-0.95 wherein, n=2-200.
2. according to the described poly-paraphenylene terephthalamide's quadrol of claim 1/hexanediamine multipolymer, it is characterized in that solvent is at least a in pentane, hexane, hexanaphthene, I class sherwood oil, II class sherwood oil and the methylene dichloride.
3. according to the described poly-paraphenylene terephthalamide's quadrol of claim 1/hexanediamine multipolymer, it is characterized in that auxiliary agent is N, in dinethylformamide, N,N-dimethylacetamide, dimethyl sulfoxide (DMSO) or the N-Methyl pyrrolidone any.
4. according to the described poly-paraphenylene terephthalamide's quadrol of claim 1/hexanediamine multipolymer, it is characterized in that basic cpd be in yellow soda ash, salt of wormwood, sodium hydroxide or the potassium hydroxide any.
5. according to the preparation method of the described poly-paraphenylene terephthalamide's quadrol of one of claim 1-4/hexanediamine multipolymer, it is characterized in that this method may further comprise the steps:
(1) preparation of solution of acid chloride
P-phthaloyl chloride is dissolved in solvent 100-1000 part with auxiliary agent 1-30 part for 20.3 parts is made into solution of acid chloride;
(2) preparation of poly-paraphenylene terephthalamide's quadrol/hexanediamine multipolymer
With 1 0.3-5.7 part, 1, have in the reactor of agitator, thermometer and reflux exchanger the addings of 6-hexanediamine 0.58-11.02 part, basic cpd 8-13.8 part and deionized water 80-1200 part, and solid is dissolved fully; Under the cooling bath cooling, the above-mentioned solution of acid chloride for preparing was slowly added in 0.5-2 hour in the reactor, restir reaction 1-3 hour obtains poly-paraphenylene terephthalamide's quadrol/hexanediamine multipolymer;
(3) solvent recuperation, the by product purification of collecting and gathering paraphenylene terephthalamide's quadrol/hexanediamine multipolymer
Deionized water 100-1000 part is added reactor, distillation between temperature 30-90 ℃, recovery solvent; The centrifugation reaction mixture, liquid obtains by-product salt through concentrated, crystallization, and solid obtains pure poly-paraphenylene terephthalamide's quadrol/hexanediamine multipolymer through washing, acetone purification, drying.
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN110437445A (en) * | 2019-08-21 | 2019-11-12 | 中仑塑业（福建）有限公司 | A kind of polyamide and its preparation method and application |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN110437445A (en) * | 2019-08-21 | 2019-11-12 | 中仑塑业（福建）有限公司 | A kind of polyamide and its preparation method and application |
| CN110437445B (en) * | 2019-08-21 | 2021-11-16 | 中仑塑业（福建）有限公司 | Polyamide resin and preparation method and application thereof |
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Open date: 20100519 |