CN103951822A - Modified polyesteramide and preparation method thereof - Google Patents
Modified polyesteramide and preparation method thereof Download PDFInfo
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- CN103951822A CN103951822A CN201410141787.3A CN201410141787A CN103951822A CN 103951822 A CN103951822 A CN 103951822A CN 201410141787 A CN201410141787 A CN 201410141787A CN 103951822 A CN103951822 A CN 103951822A
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Abstract
The invention provides modified polyesteramide which is prepared from the following raw materials: terephthalic acid, glycol, fatty polyamide, an additive A, an additive B, and an additive C. The invention also provides a preparation method of the modified polyesteramide. The modified polyesteramide is low in cost, and simple in preparation process; with the combination of the additive A, the additive B and the additive C, the thermal stability of the modified polyesteramide is greatly improved, and thus the chain breaking speed of a melt molecular chain during molding processing and the reduction degree of the product intrinsic viscosity for the modified polyesteramide are decreased. Meanwhile, the polymerization reaction time for polyesteramide preparation is greatly shortened.
Description
Technical field
The invention belongs to chemical field, particularly a kind of polyesteramide and preparation method thereof, is specifically related to a kind of polyamide polymers that adopts and polyethylene terephthalate is carried out to polyesteramide that modified copolymer makes and preparation method thereof.
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, China's man-made fiber output was 3,046 ten thousand tons, and wherein trevira output is 2,391 ten thousand tons, accounts for 78.5%.Although part technology and the product of China's trevira are reached advanced world standards, be also faced with simultaneously few such as the functional kind of high added value, yield poorly, quality is not high, homogeneity dog-eat-dog, the outstanding problem such as industry rate of profit is low.Super imitative cotton technology represents the highest level of synthon development.Super imitative cotton fibre should be preserved the feature of natural fiber, overcomes again the defect of natural fiber, is the tencel that over-all properties surmounts natural fiber.Starting with from polyester, to be not only production capacity because of trevira large for the super imitative cotton fibre of exploitation, and compared with other close fine kind, general technical level is higher, possesses the basis of super emulation; Meanwhile, trevira is also and the principal item of cotton blending.
At present the developing direction of the imitative cotton technology of polyester mainly contains three aspects: the one, in the process of terephthalic acid, ethylene glycol synthesizing polyester, add dibasic alcohol, the diprotic acid of other composition, obtain the submissiveer modified PET of molecular chain, the 2nd, adopt the physical methods such as abnormity processing in spinning process, the 3rd, in the synthetic preparation process of PET, introduce the polymkeric substance with amide group and carry out copolymerization and obtain polyesteramide.First method is because copolymerization composition is many, addition is large, and manufacturing requirements is high, control is difficult and be difficult to form scale production, and second method effect is limited, adopts the third method not only can scale operation, and product performance conveniently regulating and controlling; But polymeric amide and polyester consistency are bad, the multipolymer poor stability that adopts common process, composition to obtain.
Patent CN200410067840.6 discloses after a kind of use polymeric amide and polyethylene-methacrylate are combined to form dyeability modifier and has added in polyester slice, prepares the method for acid dyeable modified polyester fiber.But polymeric amide and polyester consistency are bad, between both end groups and molecule segment reactive behavior a little less than, the matrix material obtaining by blending method is still two-phase on microcosmic, spinning is also more difficult, is difficult to industrial applications.
Patent CN101450990A discloses a kind of method that adopts polyamide 6 and the copolycondensation of polyester carboxylate diglycol terephthalate to prepare acidic dyeable polyester and fiber thereof.Due to polyamide 6 very easily oxidative degradation variable color under high temperature, aqueous conditions, the copolyesters being obtained by the method forming process as extruding spinning, injection moulding blowing process in very easily degraded cause product quality reduce.
Summary of the invention
Goal of the invention: in order to overcome above-mentioned the deficiencies in the prior art, the object of the present invention is to provide a kind of polyesteramide of good stability.This polyesteramide copolyesters has added the additive that is specially adapted to this system for modification, has effectively reduced its limiting viscosity in molding process and has fallen.
The second object of the present invention is to provide the preparation method of the polyesteramide that aforementioned stable is good, after it reacts with ethylene glycol esterification by terephthalic acid, add polymeric amide and be specially adapted to the stablizer of this system, make polyester carboxylate, oligomer and polymeric amide copolymerization, prepare polyesteramide multipolymer.Owing to adding the stablizer that is specially adapted to this system, shorten and reached the required polymerization reaction time of certain limiting viscosity, improve the heat decomposition temperature of copolyamide ester, reduce the limiting viscosity of copolyamide ester in molding process and fallen.
Technical scheme: a kind of modified polyamide ester provided by the invention, made by following raw material: terephthalic acid, ethylene glycol, fatty polyamide, additive A, additive B and addition of C.
As preferably, made by the raw material of following weight part: 100 parts of terephthalic acids, ethylene glycol 40-80 part, fatty polyamide 6-60 part; Additive A accounts for 0～3000ppm of terephthalic acid, ethylene glycol, fatty polyamide total mass, preferably 0～500ppm, more preferably 200-300ppm; Additive B accounts for 0～2000ppm of terephthalic acid, ethylene glycol, fatty polyamide total mass, preferably 0～500ppm, more preferably 200-300ppm; Additive accounts for 0～1000ppm of terephthalic acid, ethylene glycol, fatty polyamide total mass, preferably 0～200ppm, more preferably 50-150ppm; When wherein A, B are different, be 0.
Preferred as another kind, the limiting viscosity of described modified polyamide ester is 0.64～0.75dL/g.
Preferred as another kind, described fatty polyamide is selected from one or more in PA6, PA11, PA12, PA56, PA66, PA610, PA612, PA1010, its relative viscosity 2.0～2.8.
Preferred as another kind, described additive A is selected from
h161,
one or more in H10, ST-1385, DH-446, AQ21, DH201-460.
Preferred as another kind, described additive B is selected from one or more in phosphoric acid, phosphorous acid, sodium hypophosphite, tripoly phosphate sodium STPP, phosphoric acid ester, phosphorous acid ester, polyphosphoric acid.
Preferred as another kind, described addition of C is selected from one or more in tetramethylolmethane, pyromellitic dianhydride, trimellitic anhydride, glycerol, hexanodioic acid.
The present invention also provides the preparation method of above-mentioned modified polyamide ester, comprises the following steps: terephthalic acid reacts with ethylene glycol esterification and generates ethylene glycol terephthalate; Under additive A, additive B and addition of C exist, ethylene glycol terephthalate and polymeric amide polycondensation, obtain modified polyamide ester.
As preferably, described preparation method, comprises the following steps:
(1) terephthalic acid and ethylene glycol esterification 1-3h under 220-270 DEG C, 0.1-0.4MPa, obtains ethylene glycol terephthalate;
(2) under additive A, additive B, addition of C exist, ethylene glycol terephthalate reacts at 250-280 DEG C with polymeric amide, and pressure is down to 10-600Pa in 10-60min, continues reaction 30-180min, to obtain final product.
Preferred as another kind, described preparation method, comprises the following steps:
(1) terephthalic acid and ethylene glycol react 50-120min under 220-270 DEG C, 0.01～0.25MPa; Under 240-275 DEG C, 0.01～0.15MPa, react 20-80min again, obtain ethylene glycol terephthalate;
(2), under additive A, additive B, addition of C exist, ethylene glycol terephthalate and polymeric amide react 50～100min under 240～270 DEG C, 5000～20000Pa; Under 250～280 DEG C, 2000～10000Pa, react 20～60min again; Under 250～280 DEG C, 100～2000Pa, react 60～180min again, to obtain final product.
The catalyzer that all needs to add above catalytic amount in any reaction system, described catalyzer is the one in Antimony Triacetate, antimonous oxide, antimony glycol.
Beneficial effect: modified polyamide ester cost provided by the invention is low, preparation technology is simple, by the combination of additive A, additive B and addition of C, greatly improve the thermal stability of modified polyamide ester, thereby reduced this modified polyamide ester the chain rupture speed of molecular melt chain and reduction degree of product performance viscosity in molding process; Also greatly shortened polymerization reaction time prepared by polyesteramide simultaneously.
Particularly, the present invention adopts continuation method to produce and obtains modified polyamide ester, has solved the compatibility problem of polyester and polymeric amide, makes both generate the multipolymer of homogeneous by transesterification reaction, makes it to have concurrently the advantage of polyester and polymeric amide.On the one hand, in the intersegmental introducing polyamide segment of polyethylene terephthalate chain, thereby strengthen whole polarity of chain, Hyarogen-bonding between molecular chain and the cohesive energy density(CED) of copolyamide ester are improved, not only be conducive to the dyeing processing of rear dao, can in reducing dyeing temperature, improve dye uptake, but also improve the gas barrier property of copolyamide ester; Add on the other hand the additive that is particularly suitable for improving polyester, polymeric amide thermal stability, overcome polyesteramide fibre resistance toheat prepared by existing method poor, easily molecular chain chain rupture in melt-spinning process, the problem that product performance viscosity drop is large, significantly reduced prepare polyesteramide with and molding process in the chain rupture speed of polyesteramide molecular chain and the reduction degree of product performance viscosity.
The present invention adopts the combination of additive A, additive B and addition of C, and these three kinds of additives act synergistically in product, and compared with adopting single additive or two kinds of additives, the polyesteramide performance making significantly improves, and particularly stability is very excellent.
Embodiment
Embodiment 1
In stainless steel cauldron, drop into 0.05 part of 100 parts of terephthalic acid, 60 parts of ethylene glycol, Antimony Triacetate, 235 DEG C of temperature of reaction controls, reaction pressure 0.25MPa, carry out esterification 2h; Reaction PA630 part that input relative viscosity is 2.0 afterwards,
0.38 part of L110.57 part, trimethyl phosphite, stir 10min, and Temperature Setting is 260 DEG C afterwards, and pressure is progressively down to 50Pa in 45min, continues reaction 105min, obtains modified polyamide ester.
Embodiment 2
In stainless steel cauldron, drop into 0.05 part of 100 parts of terephthalic acid, 50 parts of ethylene glycol, Antimony Triacetate, 265 DEG C of temperature of reaction controls, reaction pressure 0.2MPa, carry out esterification 2h; After reaction, drop into PA1110 part, DH201-4600.5 part that relative viscosity is 2.1 and stir 60min, Temperature Setting is 265 DEG C afterwards, and pressure is progressively down to 300Pa in 50min, continues reaction 95min, obtains modified polyamide ester.
Embodiment 3
In stainless steel cauldron, drop into 0.05 part of 100 parts of terephthalic acid, 60 parts of ethylene glycol, Antimony Triacetate, 235 DEG C of temperature of reaction controls, reaction pressure 0.25MPa, carry out esterification 1h; Reaction PA620 part that input relative viscosity is 2.2 afterwards,
0.09 part, H1610.18 part, phosphorous acid, stir 10min, and then Temperature Setting is 260 DEG C, and pressure is progressively down to 50Pa in 45min, continues reaction 106min, obtains modified polyamide ester.
Embodiment 4
In stainless steel cauldron, drop into 0.05 part of 100 parts of terephthalic acid, 70 parts of ethylene glycol, Antimony Triacetate, 235 DEG C of temperature of reaction controls, reaction pressure 0.25MPa, carries out esterification 2h; 0.04 part of PA1230 part, ST-13850.10 part, sodium hypophosphite that after reaction, input relative viscosity is 2.3, stir 15min, and Temperature Setting is 258 DEG C afterwards, and pressure is progressively down to 200Pa in 45min, continues reaction 100min, obtains modified polyamide ester.
Embodiment 5
In stainless steel cauldron, drop into 0.05 part of 100 parts of terephthalic acid, 80 parts of ethylene glycol, Antimony Triacetate, 255 DEG C of temperature of reaction controls, reaction pressure 0.2MPa, carry out esterification 2h; Reaction PA5640 part that input relative viscosity is 2.5 afterwards,
h100.066 part, 0.066 part of tripoly phosphate sodium STPP, 0.2 part of hexanodioic acid also stir 10min, and Temperature Setting is 260 DEG C afterwards, and pressure is progressively down to 100Pa in 35min, continue reaction 30min, obtain modified polyamide ester.
Embodiment 6
In stainless steel cauldron, drop into 0.08 part of 100 parts of terephthalic acid, 60 parts of ethylene glycol, Antimony Triacetate, 220 DEG C of temperature of reaction controls, reaction pressure 0.01MPa, carry out esterification 3h; After reaction, drop into 0.044 part of 0.21 part of PA61050 part, DH-4460.042 part, trimethyl phosphite 99, the glycerol that relative viscosity is 2.5 and stir 10min, Temperature Setting is 250 DEG C afterwards, pressure is progressively down to 600Pa in 10min, continues reaction 180min, obtains modified polyamide ester.Embodiment 7
In stainless steel cauldron, drop into 0.07 part of 100 parts of terephthalic acid, 80 parts of ethylene glycol, Antimony Triacetate, 270 DEG C of temperature of reaction controls, reaction pressure 0.40MPa, carry out esterification 1h; After reaction, drop into 0.0105 part of 0.093 part of PA6126 part, AQ210.27 part, polyphosphoric acid, the trimellitic anhydride that relative viscosity is 2.6 and stir 10min, Temperature Setting is 280 DEG C afterwards, pressure is progressively down to 10Pa in 60min, continues reaction 60min, obtains modified polyamide ester.Embodiment 8
In stainless steel cauldron, drop into 0.04 part of 100 parts of terephthalic acid, 40 parts of ethylene glycol, Antimony Triacetate, 240 DEG C of temperature of reaction controls, reaction pressure 0.1MPa, carry out esterification 2h; After reaction, drop into 0.0279 part of 0.30 part of PA101060 part, phosphoric acid, the pyromellitic dianhydride that relative viscosity is 2.8 and stir 10min, Temperature Setting is 270 DEG C afterwards, pressure is progressively down to 50Pa in 35min, continues reaction 100min, obtains modified polyamide ester.
Embodiment 9
On 1000t/a polyester production device, in 100 parts of terephthalic acids, 60 parts of ethylene glycol, 0.06 part of input esterifying kettle of Antimony Triacetate, 240 DEG C of temperature of reaction controls, esterification 60min under 0.25MPa; Under 250 DEG C, 0.15MPa, react 50min again, obtain ethylene glycol terephthalate; Then reaction mass enters batch condensation polymerization reactor, to drop into relative viscosity be 2.4 PA6640 part,
h100.1 part, 0.1 part of trimethyl phosphite 99,0.1 part of tetramethylolmethane are set up vacuum in still gradually and reach 20000Pa in 50min, and 265 DEG C are reacted 80min; Under 260 DEG C, 10000Pa, react 20min again; Under 260 DEG C, 2000Pa, react 100min again, obtain modified polyamide ester.
Embodiment 10
On 1000t/a polyester production device, in 100 parts of terephthalic acids, 60 parts of ethylene glycol, 0.05 part of input esterifying kettle of Antimony Triacetate, 220 DEG C of temperature of reaction controls, 0.01MPa esterification 120min; Under 240 DEG C, 0.01MPa, react 80min again, obtain ethylene glycol terephthalate; Then reaction mass enters batch condensation polymerization reactor, to drop into relative viscosity be 2.4 PA6640 part,
h100.1 part, 0.1 part of trimethyl phosphite 99,0.1 part of tetramethylolmethane are set up vacuum in still gradually and reach 5000Pa in 50min, and 240 DEG C are reacted 100min; Under 250 DEG C, 2000Pa, react 60min again; Under 250 DEG C, 100Pa, react 180min again, obtain modified polyamide ester.
Embodiment 11
On 1000t/a polyester production device, in 100 parts of terephthalic acids, 60 parts of ethylene glycol, 0.05 part of input esterifying kettle of Antimony Triacetate, 270 DEG C of temperature of reaction controls, 0.15MPa esterification 50min; Under 275 DEG C, 0.10MPa, react 20min again, obtain ethylene glycol terephthalate; Then reaction mass enters batch condensation polymerization reactor, to drop into relative viscosity be 2.4 PA6640 part,
h101.2 part, trimethyl phosphite 99 50g, tetramethylolmethane 80g set up vacuum in still gradually and reach 10000Pa in 50min, and 270 DEG C are reacted 50min; Under 280 DEG C, 5000Pa, react 40min again; Under 280 DEG C, 500Pa, react 60min again, obtain modified polyamide ester.
Comparative example 1
In 2.5L stainless steel cauldron, drop into 0.05 part of 500 parts of terephthalic acid, 280 parts of ethylene glycol, Antimony Triacetate, 235 DEG C of temperature of reaction controls, reaction pressure 0.25MPa, carry out esterification, it is PA665 part of 2.0 that reaction drops into relative viscosity after 120min, stirs 10min, Temperature Setting is 260 DEG C afterwards, pressure is progressively down to 50Pa in 45min, continues reaction 120min, obtains modified polyamide ester.
Comparative example 2
In 2.5L stainless steel cauldron, drop into 0.05 part of 500 parts of terephthalic acid, 280 parts of ethylene glycol, Antimony Triacetate, 235 DEG C of temperature of reaction controls, reaction pressure 0.25MPa, carry out esterification, it is 0.3 part of 2.8 PA665 part, trimethyl phosphite 99 that reaction drops into relative viscosity after 120min, stirs 10min, Temperature Setting is 260 DEG C afterwards, pressure is progressively down to 50Pa in 45min, continues reaction 125min, obtains modified polyamide ester.
The performance that detects embodiment 1 to 11 and comparative example 1 and 2, the results are shown in Table 1.
The performance comparison of table 1 embodiment 1 to 11 and comparative example 1 and 2
Wherein, η is that limiting viscosity, Tm are that content, the Td that fusing point, DEG% are glycol ether is heat decomposition temperature; The thermostability of utilizing rheometer Rosand RH7 test modified polyamide ester, test result is in table 2.
The thermostability of table 2 modified polyamide ester
From table 1 and table 2, add modified polyamide ester that three kinds of additives make and do not add additive and add compared with the polyesteramide that one or both additives make, excellent performance, thermal stability is good.
Claims (10)
1. a modified polyamide ester, is characterized in that: be made up of following raw material: terephthalic acid, ethylene glycol, fatty polyamide, additive A, additive B and addition of C.
2. a kind of modified polyamide ester according to claim 1, is characterized in that: the raw material by following weight part is made: 100 parts of terephthalic acids, ethylene glycol 40-80 part, fatty polyamide 6-60 part; Additive A accounts for 0～3000ppm of terephthalic acid, ethylene glycol, fatty polyamide total mass, preferably 0～500ppm, more preferably 200-300ppm; Additive B accounts for 0～2000ppm of terephthalic acid, ethylene glycol, fatty polyamide total mass, preferably 0～500ppm, more preferably 200-300ppm; Addition of C accounts for 0～1000ppm of terephthalic acid, ethylene glycol, fatty polyamide total mass, preferably 0～200ppm, more preferably 50-150ppm; When wherein A, B are different, be 0.
3. a kind of modified polyamide ester according to claim 1, is characterized in that: the limiting viscosity of described modified polyamide ester is 0.64～0.75dL/g.
4. a kind of modified polyamide ester according to claim 1, is characterized in that: described fatty polyamide is selected from one or more in PA6, PA11, PA12, PA56, PA66, PA610, PA612, PA1010, its relative viscosity 2.0～2.8.
5. a kind of modified polyamide ester according to claim 1, is characterized in that: described additive A is selected from
one or more in H10, ST-1385, DH-446, AQ21, DH201-460.
6. a kind of modified polyamide ester according to claim 1, is characterized in that: described additive B is selected from one or more in phosphoric acid, phosphorous acid, sodium hypophosphite, tripoly phosphate sodium STPP, phosphoric acid ester, phosphorous acid ester, polyphosphoric acid.
7. a kind of modified polyamide ester according to claim 1, is characterized in that: described addition of C is selected from one or more in tetramethylolmethane, pyromellitic dianhydride, trimellitic anhydride, glycerol, hexanodioic acid.
8. the preparation method of the modified polyamide ester described in claim 1-7 any one, is characterized in that: comprise the following steps: terephthalic acid reacts with ethylene glycol esterification and generates ethylene glycol terephthalate; Under additive A, additive B and addition of C exist, ethylene glycol terephthalate and polymeric amide polycondensation, obtain modified polyamide ester.
9. the preparation method of modified polyamide ester according to claim 8, is characterized in that: comprise the following steps:
(1) terephthalic acid and ethylene glycol esterification 1-3h under 220-270 DEG C, 0.01-0.4MPa, obtains ethylene glycol terephthalate;
(2) under additive A, additive B, addition of C exist, ethylene glycol terephthalate reacts at 250-280 DEG C with polymeric amide, and pressure is down to 10-600Pa in 10-60min, continues reaction 30-180min, to obtain final product.
10. the preparation method of modified polyamide ester according to claim 8, is characterized in that: comprise the following steps:
(1) terephthalic acid and ethylene glycol react 50-120min under 220-270 DEG C, 0.01～0.25MPa; Under 240-275 DEG C, 0.01～0.15MPa, react 20-80min again, obtain ethylene glycol terephthalate;
(2), under additive A, additive B, addition of C exist, ethylene glycol terephthalate and polymeric amide react 50～100min under 240～270 DEG C, 5000～20000Pa; Under 250～280 DEG C, 2000～10000Pa, react 20～60min again; Under 250～280 DEG C, 100～2000Pa, react 60～180min again, to obtain final product.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN107237038A (en) * | 2017-07-31 | 2017-10-10 | 嘉兴珠朗服饰有限公司 | A kind of its production technology of anti-electron radiation wool product |
| 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 |
| CN110845711A (en) * | 2019-07-19 | 2020-02-28 | 江建明 | Control method and application of PET average sequence length in PET-PA6 |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN107237038A (en) * | 2017-07-31 | 2017-10-10 | 嘉兴珠朗服饰有限公司 | A kind of its production technology of anti-electron radiation wool product |
| 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 |
| CN110845711A (en) * | 2019-07-19 | 2020-02-28 | 江建明 | Control method and application of PET average sequence length in PET-PA6 |
| 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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Effective date of registration: 20160705 Address after: 211900 Yizheng Changjiang Road, Jiangsu, China, No. 1, No. Applicant after: CHINA SINOPEC YIZHENG CHEMICAL FIBER CO., LTD. Applicant after: Sinopec Corp. Address before: 100728 Beijing, Chaoyangmen, North Street, No. 22, No. Applicant before: Sinopec Corp. Applicant before: Yizheng Chemical Fiber Co., Ltd., China Petrochemical Group Corp. |
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| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant |