CN103951822B - A kind of modified polyamide ester and preparation method thereof - Google Patents
A kind of modified polyamide ester and preparation method thereof Download PDFInfo
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Abstract
A kind of modified polyamide ester that the present invention provides, is made up of following raw material: p-phthalic acid, ethylene glycol, fatty polyamide, additive A, additive B and addition of C.Present invention also offers the preparation method of above-mentioned modified polyamide ester.This modified polyamide ester low cost, preparation technology are simple, by additive A, additive B and the combination of addition of C, substantially increase the thermal stability of modified polyamide ester, thus reduce chain rupture speed and the reduction degree of product attribute viscosity of this modified polyamide ester molecular melt chain in molding process；The most also substantially reduce polymerization reaction time prepared by polyesteramide.
Description
Technical field
The invention belongs to chemical field, particularly to a kind of polyesteramide and preparation method thereof, be specifically related to a kind of employing
Polyamide polymers is modified prepared polyesteramide of copolymerization and preparation method thereof to polyethylene terephthalate.
Background technology
Chemical fibre, as the basic industry of textile industry, is the key industry of China's planning and development all the time.In Jan-Sept, 2013 I
State's chemical fibre yield is 30,460,000 tons, and wherein polyester fiber yield is 23,910,000 tons, accounts for 78.5%.Although China's polyester is fine
Portion of techniques and the product of dimension are reached advanced world standards, are also faced with that the functional kind of such as high added value is few simultaneously, produce
Measuring low, quality is the highest, homogeneity dog-eat-dog, the outstanding problems such as industrial profit rate is low.Super imitative cotton technology represents synthetic fibers and sends out
The top level of exhibition.Super imitative cotton fiber should preserve the feature of natural fiber, overcomes the defect of natural fiber again, is comprehensive
The tencel of natural fiber can be surmounted.Start with from polyester and develop super imitative cotton fiber and be not only due to the production capacity of polyester fiber greatly,
Closing compared with fine kind with other, general technical level is higher, possesses the basis of super emulation；Meanwhile, polyester fiber is also to mix with cotton
The principal item spun.
The developing direction of the imitative cotton technology of polyester mainly has three aspects at present: one is in p-phthalic acid, ethylene glycol synthesis
Adding the dihydroxylic alcohols of other composition, binary acid during polyester, obtain the modified PET that strand is submissiveer, two is to use to spin
The physical methods such as the special-shaped processing during Si, three be PET synthetically prepared during introduce there is the polymerization of amide group
Thing carries out copolymerization and obtains polyesteramide.First method is because copolymerization composition is many, addition big, and manufacturing requirements is high, it is tired to control
Difficult and be difficult to be formed large-scale production, second method effect is limited, uses the third method to be possible not only to large-scale production, and produces
Moral character energy conveniently regulating and controlling；But, polyamide is bad with the polyester compatibility, and the copolymer using common process, composition to obtain is stable
Property is poor.
Patent CN200410067840.6 discloses a kind of use polyamide and is formed with the combination of polyethylene methacrylic acid salt
Add to after dyeability modifier in polyester slice, the method preparing acid dyeable modified polyester fiber.But polyamide and polyester phase
Capacitive is bad, and between both end group and molecule segments, reactivity is more weak, and the composite obtained by blending method is at microcosmic
On still in biphase, spinning is the most relatively difficult, it is difficult to industrial applications.
Patent CN101450990A discloses a kind of employing polyamide 6 and polyester esterification thing diglycol terephthalate
The method of acidic dyeable polyester and fiber thereof is prepared in copolycondensation.Due to polyamide 6 easily oxidative degradation under high temperature, aqueous conditions
Variable color, the method the copolyesters obtained easily degraded in processing and forming such as extruding spinning, injection blow-molding process causes product
Quality reduces.
Summary of the invention
Goal of the invention: in order to overcome above-mentioned the deficiencies in the prior art, it is an object of the invention to provide a kind of good stability
Polyesteramide.This polyesteramide copolyesters with the addition of and is particularly well-suited to the additive of this system for modification, is effectively reduced
Its intrinsic viscosity fall in molding process.
The second object of the present invention is the preparation method of the polyesteramide that offer aforementioned stable is good, and it is by benzene two
After formic acid and ethylene glycol esterification, add polyamide and be particularly well-suited to the stabilizer of this system, making polyester esterification thing, low
Aggressiveness and copolyamide, prepare polyester amide copolymer.Owing to adding the stabilizer being particularly well-suited to this system, shorten
Reach the polymerization reaction time needed for certain intrinsic viscosity, improve the heat decomposition temperature of copolyamide ester, reduce copolymerization acyl
Amine ester intrinsic viscosity fall in molding process.
Technical scheme: a kind of modified polyamide ester that the present invention provides, is made up of following raw material: p-phthalic acid, second two
Alcohol, fatty polyamide, additive A, additive B and addition of C.
As preferably, it is made up of the raw material of following weight portion: p-phthalic acid 100 parts, ethylene glycol 40-80 part, aliphatic
Polyamide 6-60 parts；Additive A accounts for p-phthalic acid, ethylene glycol, the 0 of fatty polyamide gross mass～3000ppm, and preferably 0
～500ppm, more preferably 200-300ppm；Additive B account for p-phthalic acid, ethylene glycol, the 0 of fatty polyamide gross mass～
2000ppm, preferably 0～500ppm, more preferably 200-300ppm；Additive accounts for p-phthalic acid, ethylene glycol, fatty polyamide
The 0～1000ppm of gross mass, preferably 0～200ppm, more preferably 50-150ppm；It is wherein 0 during A, B difference.
Preferred as another kind, the intrinsic viscosity of described modified polyamide ester is 0.64～0.75dL/g.
Preferred as another kind, described fatty polyamide selected from PA6, PA11, PA12, PA56, PA66, PA610,
One or more in PA612, PA1010, its relative viscosity 2.0～2.8.
Preferred as another kind, described additive A is selected fromH161、One or more in H10, ST-1385, DH-446, AQ21, DH201-460.
Preferred as another kind, described additive B selected from phosphoric acid, phosphorous acid, sodium hypophosphite, sodium tripolyphosphate, phosphate ester,
One or more in phosphite ester, polyphosphoric acids.
Preferred as another kind, described addition of C selected from tetramethylolmethane, pyromellitic dianhydride, trimellitic anhydride, the third three
One or more in alcohol, adipic acid.
Present invention also offers the preparation method of above-mentioned modified polyamide ester, comprise the following steps: p-phthalic acid and second
Glycol esterification generates ethylene glycol terephthalate；In the presence of additive A, additive B and addition of C, terephthaldehyde
Acid glycol ester and polyamide polycondensation, obtain modified polyamide ester.
As preferably, described preparation method, comprise the following steps:
(1) p-phthalic acid and ethylene glycol are 220-270 DEG C, esterification 1-3h under 0.1-0.4MPa, obtain terephthaldehyde
Acid glycol ester；
(2) in the presence of additive A, additive B, addition of C, ethylene glycol terephthalate and polyamide are at 250-
Reacting at 280 DEG C, pressure is down to 10-600Pa in 10-60min, continues reaction 30-180min, to obtain final product.
Preferred as another kind, described preparation method, comprise the following steps:
(1) p-phthalic acid and ethylene glycol react 50-120min under 220-270 DEG C, 0.01～0.25MPa；Exist again
React 20-80min under 240-275 DEG C, 0.01～0.15MPa, obtain ethylene glycol terephthalate；
(2) in the presence of additive A, additive B, addition of C, ethylene glycol terephthalate and polyamide 240～
50～100min are reacted under 270 DEG C, 5000～20000Pa；Again under 250～280 DEG C, 2000～10000Pa react 20～
60min；Under 250～280 DEG C, 100～2000Pa, react 60～180min again, to obtain final product.
Being both needed to add the catalyst of catalytic amount in any of the above reaction system, described catalyst is antimony triacetate, three oxidations
One in two antimony, antimony glycol.
Beneficial effect: modified polyamide ester low cost, preparation technology that the present invention provides are simple, by additive A, interpolation
Agent B and the combination of addition of C, substantially increase the thermal stability of modified polyamide ester, thus reduce this modified polyamide
The chain rupture speed of ester molecular melt chain in molding process and the reduction degree of product attribute viscosity；The most also it is greatly shortened
Polymerization reaction time prepared by polyesteramide.
Specifically, the present invention uses continuation method to produce to obtain modified polyamide ester, solve polyester and polyamide
Consistency problem, makes both generate homogeneous copolymer by ester exchange reaction, is allowed to the advantage having polyester and polyamide concurrently.One
Aspect, in polyethylene terephthalate chain intersegmental introducing polyamide segment, thus enhances whole polarity of chain, carries
The Hyarogen-bonding of high molecule interchain and the cohesion energy density of copolyamide ester, the dyeing not only contributing to rear dao adds
Work, can improve dye-uptake while reducing dyeing temperature, but also improve the gas barrier property of copolyamide ester；Another
Aspect with the addition of and is particularly suitable for improving polyester, the additive of polyamide thermal stability, overcomes polyamides prepared by existing method
Amine ester fiber heat resistance is poor, easy strand chain rupture during melt spinning, the problem that product attribute viscosity drop is big, significantly drops
The low chain rupture speed preparing polyesteramide strand in polyesteramide and its molding process and product attribute viscosity
Reduction degree.
The present invention uses the combination of additive A, additive B and addition of C, and these three kinds of additives are collaborative in the product to be made
With, compared with using single additive or two kinds of additives, the polyesteramide performance prepared significantly improves, particularly stability
Can be the most excellent.
Detailed description of the invention
Embodiment 1
Stainless steel cauldron puts into 100 parts of p-phthalic acids, 60 parts of ethylene glycol, antimony triacetates 0.05 part, reaction temperature
Control 235 DEG C, reaction pressure 0.25MPa, carry out esterification 2h；After reaction put into relative viscosity be 2.0 PA630 part,L110.57 part, NSC 6513 0.38 part, stirs 10min, and temperature is set as 260 DEG C afterwards, and pressure exists
Progressively it is down to 50Pa in 45min, continues reaction 105min, obtain modified polyamide ester.
Embodiment 2
Stainless steel cauldron puts into 100 parts of p-phthalic acids, 50 parts of ethylene glycol, antimony triacetates 0.05 part, reaction temperature
Control 265 DEG C, reaction pressure 0.2MPa, carry out esterification 2h；After reaction put into relative viscosity be 2.1 PA1110 part,
DH201-4600.5 part also stirs 60min, and temperature is set as 265 DEG C afterwards, and pressure is progressively down to 300Pa in 50min, continues
Reaction 95min, obtains modified polyamide ester.
Embodiment 3
Stainless steel cauldron puts into 100 parts of p-phthalic acids, 60 parts of ethylene glycol, antimony triacetates 0.05 part, reaction temperature
Control 235 DEG C, reaction pressure 0.25MPa, carry out esterification 1h；After reaction put into relative viscosity be 2.2 PA620 part,0.09 part of H1610.18 part, phosphorous acid, stirs 10min, and then temperature is set as 260 DEG C, and pressure is in 45min
Progressively it is down to 50Pa, continues reaction 106min, obtain modified polyamide ester.
Embodiment 4
Stainless steel cauldron puts into 100 parts of p-phthalic acids, 70 parts of ethylene glycol, antimony triacetates 0.05 part, reaction temperature
Control 235 DEG C, reaction pressure 0.25MPa, carry out esterification 2h；After reaction put into relative viscosity be 2.3 PA1230 part,
ST-13850.10 part, sodium hypophosphite 0.04 part, stir 15min, temperature is set as 258 DEG C afterwards, pressure in 45min progressively
It is down to 200Pa, continues reaction 100min, obtain modified polyamide ester.
Embodiment 5
Stainless steel cauldron puts into 100 parts of p-phthalic acids, 80 parts of ethylene glycol, antimony triacetates 0.05 part, reaction temperature
Control 255 DEG C, reaction pressure 0.2MPa, carry out esterification 2h；After reaction put into relative viscosity be 2.5 PA5640 part,H100.066 part, sodium tripolyphosphate 0.066 part, adipic acid 0.2 part also stir 10min, and temperature is set as afterwards
260 DEG C, pressure is progressively down to 100Pa in 35min, continues reaction 30min, obtains modified polyamide ester.
Embodiment 6
Stainless steel cauldron puts into 100 parts of p-phthalic acids, 60 parts of ethylene glycol, antimony triacetates 0.08 part, reaction temperature
Control 220 DEG C, reaction pressure 0.01MPa, carry out esterification 3h；After reaction put into relative viscosity be 2.5 PA61050 part,
DH-4460.042 part, trimethyl phosphate 0.21 part, glycerol 0.044 part also stir 10min, and temperature is set as 250 DEG C afterwards,
Pressure is progressively down to 600Pa in 10min, continues reaction 180min, obtains modified polyamide ester.Embodiment 7
Stainless steel cauldron puts into 100 parts of p-phthalic acids, 80 parts of ethylene glycol, antimony triacetates 0.07 part, reaction temperature
Control 270 DEG C, reaction pressure 0.40MPa, carry out esterification 1h；After reaction put into relative viscosity be 2.6 PA6126 part,
AQ210.27 part, polyphosphoric acids 0.093 part, trimellitic anhydride 0.0105 part also stir 10min, and temperature is set as 280 afterwards
DEG C, pressure is progressively down to 10Pa in 60min, continues reaction 60min, obtains modified polyamide ester.Embodiment 8
Stainless steel cauldron puts into 100 parts of p-phthalic acids, 40 parts of ethylene glycol, antimony triacetates 0.04 part, reaction temperature
Control 240 DEG C, reaction pressure 0.1MPa, carry out esterification 2h；After reaction put into relative viscosity be 2.8 PA101060 part,
Phosphoric acid 0.30 part, pyromellitic dianhydride 0.0279 part also stir 10min, and temperature is set as 270 DEG C afterwards, and pressure is in 35min
Progressively it is down to 50Pa, continues reaction 100min, obtain modified polyamide ester.
Embodiment 9
On 1000t/a polyester production device, p-phthalic acid 100 parts, ethylene glycol 60 parts, antimony triacetate 0.06 part input
In esterifying kettle, reaction temperature controls 240 DEG C, esterification 60min under 0.25MPa；Again 250 DEG C, react under 0.15MPa
50min, obtains ethylene glycol terephthalate；Then reaction mass enters batch condensation polymerization reactor, and putting into relative viscosity is 2.4
PA6640 part,H100.1 part, trimethyl phosphate 0.1 part, tetramethylolmethane 0.1 part, by vacuum in still in 50min
Gradually build up and reach 20000Pa, 265 DEG C of reaction 80min；Again 260 DEG C, react 20min under 10000Pa；Again 260 DEG C,
React 100min under 2000Pa, obtain modified polyamide ester.
Embodiment 10
On 1000t/a polyester production device, p-phthalic acid 100 parts, ethylene glycol 60 parts, antimony triacetate 0.05 part input
In esterifying kettle, reaction temperature controls 220 DEG C, 0.01MPa esterification 120min；Again 240 DEG C, react under 0.01MPa
80min, obtains ethylene glycol terephthalate；Then reaction mass enters batch condensation polymerization reactor, and putting into relative viscosity is 2.4
PA6640 part,H100.1 part, trimethyl phosphate 0.1 part, tetramethylolmethane 0.1 part, by vacuum in still in 50min
Gradually build up and reach 5000Pa, 240 DEG C of reaction 100min；Again 250 DEG C, react 60min under 2000Pa；Again 250 DEG C,
React 180min under 100Pa, obtain modified polyamide ester.
Embodiment 11
On 1000t/a polyester production device, p-phthalic acid 100 parts, ethylene glycol 60 parts, antimony triacetate 0.05 part input
In esterifying kettle, reaction temperature controls 270 DEG C, 0.15MPa esterification 50min；Again 275 DEG C, react 20min under 0.10MPa,
Obtain ethylene glycol terephthalate；Then reaction mass enter batch condensation polymerization reactor, put into relative viscosity be 2.4 PA6640 part,H101.2 part, trimethyl phosphate 50g, tetramethylolmethane 80g, gradually build up vacuum in still in 50min and reach
To 10000Pa, 270 DEG C of reaction 50min；Again 280 DEG C, react 40min under 5000Pa；Again 280 DEG C, react under 500Pa
60min, obtains modified polyamide ester.
Comparative example 1
500 parts of p-phthalic acids, 280 parts of ethylene glycol, antimony triacetates 0.05 part are put into, instead in 2.5L stainless steel cauldron
Temperature is answered to control 235 DEG C, reaction pressure 0.25MPa, carry out esterification, putting into relative viscosity after reaction 120min is 2.0
PA665 part, stirs 10min, and temperature is set as 260 DEG C afterwards, and pressure is progressively down to 50Pa in 45min, continues reaction
120min, obtains modified polyamide ester.
Comparative example 2
500 parts of p-phthalic acids, 280 parts of ethylene glycol, antimony triacetates 0.05 part are put into, instead in 2.5L stainless steel cauldron
Temperature is answered to control 235 DEG C, reaction pressure 0.25MPa, carry out esterification, putting into relative viscosity after reaction 120min is 2.8
PA665 part, trimethyl phosphate 0.3 part, stirs 10min, and temperature is set as 260 DEG C afterwards, and pressure is progressively down in 45min
50Pa, continues reaction 125min, obtains modified polyamide ester.
Detection embodiment 1 to 11 and the performance of comparative example 1 and 2, the results are shown in Table 1.
Table 1 embodiment 1 to 11 and the performance comparison of comparative example 1 and 2
Wherein, η be intrinsic viscosity, Tm be fusing point, DEG% be the content of diethylene glycol, Td be heat decomposition temperature；Utilize rheology
The heat stability of instrument Rosand RH7 test modified polyamide ester, test result is shown in Table 2.
The heat stability of table 2 modified polyamide ester
From Tables 1 and 2, add the prepared modified polyamide ester of three kinds of additives and be added without additive and addition
The polyesteramide that one or both additives prepare is compared, and excellent performance, thermal stability is good.
Claims (6)
1. a modified polyamide ester, it is characterised in that: it is made up of the raw material of following weight portion:
P-phthalic acid 100 parts, ethylene glycol 40-80 part, fatty polyamide 6-60 part；Additive A accounts for p-phthalic acid, second two
Alcohol, the 0 of fatty polyamide gross mass～3000ppm, additive B accounts for p-phthalic acid, ethylene glycol, the total matter of fatty polyamide
The 0～2000ppm of amount, addition of C accounts for p-phthalic acid, ethylene glycol, the 0 of fatty polyamide gross mass～1000ppm, wherein
A, B, C are not 0 simultaneously；Described additive A is selected from
One or more in ST-1385, described additive B selected from phosphoric acid, phosphorous acid, sodium hypophosphite, sodium tripolyphosphate, phosphate ester,
One or more in phosphite ester, polyphosphoric acids, described addition of C is selected from tetramethylolmethane, pyromellitic dianhydride, inclined benzene front three
One or more in anhydride, glycerol, adipic acid.
A kind of modified polyamide ester the most according to claim 1, it is characterised in that: the characteristic of described modified polyamide ester is glued
Degree is 0.64～0.75dL/g.
A kind of modified polyamide ester the most according to claim 1, it is characterised in that: described fatty polyamide selected from PA6,
One or more in PA11, PA12, PA56, PA66, PA610, PA612, PA1010, its relative viscosity 2.0～2.8.
4. the preparation method of the modified polyamide ester described in any one of claim 1-3, it is characterised in that: comprise the following steps:
P-phthalic acid generates ethylene glycol terephthalate with ethylene glycol esterification；In additive A, additive B and interpolation
In the presence of agent C, ethylene glycol terephthalate and polyamide polycondensation, obtain modified polyamide ester.
The preparation method of modified polyamide ester the most according to claim 4, it is characterised in that: comprise the following steps:
(1) p-phthalic acid and ethylene glycol are 220-270 DEG C, esterification 1-3h under 0.01-0.4MPa, obtain p-phthalic acid second
Diol ester；
(2) in the presence of additive A, additive B, addition of C, ethylene glycol terephthalate and polyamide are at 250-280 DEG C
Lower reaction, pressure is down to 10-600Pa in 10-60min, is continued reaction 30-180min, to obtain final product.
The preparation method of modified polyamide ester the most according to claim 4, it is characterised in that: comprise the following steps:
(1) p-phthalic acid and ethylene glycol react 50-120min under 220-270 DEG C, 0.01～0.25MPa；Again at 240-275
DEG C, 0.01～0.15MPa under react 20-80min, obtain ethylene glycol terephthalate；
(2) in the presence of additive A, additive B, addition of C, ethylene glycol terephthalate and polyamide are 240～270
DEG C, 5000～20000Pa under react 50～100min；20～60min are reacted again under 250～280 DEG C, 2000～10000Pa；
Under 250～280 DEG C, 100～2000Pa, react 60～180min again, to obtain final product.
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| CN107630262A (en) * | 2017-10-24 | 2018-01-26 | 佛山杰致信息科技有限公司 | A kind of antibacterial wear-resisting chemical fibre and preparation method thereof |
| CN110845711B (en) * | 2019-07-19 | 2021-10-29 | 江建明 | Control method and application of PET average sequence length in PET-PA6 |
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| CN101450990A (en) * | 2007-12-06 | 2009-06-10 | 中国纺织科学研究院 | Acidic dyeable polyester and method for preparing acidic dyeable polyester and fiber thereof |
| CN101508842A (en) * | 2008-12-23 | 2009-08-19 | 深圳市科聚新材料有限公司 | Polyamide/polyester alloy and method for producing the same |
| CN101906211A (en) * | 2010-08-19 | 2010-12-08 | 中国纺织科学研究院 | Polyester-polyamide copolymer and synthetic preparation method thereof |
| CN101942708A (en) * | 2010-08-19 | 2011-01-12 | 中国纺织科学研究院 | Polyester-polyamide copolymer fiber and manufacturing method thereof |
| CN102558549A (en) * | 2010-12-15 | 2012-07-11 | 中国纺织科学研究院 | Method for continuous polymerization of modified polyester copolymer and modified polyester copolymer prepared thereby |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4254254A (en) * | 1980-01-21 | 1981-03-03 | Eastman Kodak Company | Polyester amide fabric adhesives |
| CN101450990A (en) * | 2007-12-06 | 2009-06-10 | 中国纺织科学研究院 | Acidic dyeable polyester and method for preparing acidic dyeable polyester and fiber thereof |
| CN101508842A (en) * | 2008-12-23 | 2009-08-19 | 深圳市科聚新材料有限公司 | Polyamide/polyester alloy and method for producing the same |
| CN101906211A (en) * | 2010-08-19 | 2010-12-08 | 中国纺织科学研究院 | Polyester-polyamide copolymer and synthetic preparation method thereof |
| CN101942708A (en) * | 2010-08-19 | 2011-01-12 | 中国纺织科学研究院 | Polyester-polyamide copolymer fiber and manufacturing method thereof |
| CN102558549A (en) * | 2010-12-15 | 2012-07-11 | 中国纺织科学研究院 | Method for continuous polymerization of modified polyester copolymer and modified polyester copolymer prepared thereby |
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