CN110894296B - Polyether amine modified polyamide material and preparation method thereof - Google Patents
Polyether amine modified polyamide material and preparation method thereof Download PDFInfo
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Abstract
The polyether amine modified polyamide material comprises a chain segment formed by condensation polymerization of diisocyanate and bifunctional polyether amine, wherein the chain segment is terminated by the monofunctional polyether amine, so that the surface resistivity of the prepared polyether amine modified polyamide is reduced, the moisture absorption rate is improved, and the cantilever beam notch impact strength of the modified polyamide is obviously improved.
Description
Technical Field
The invention belongs to the field of nylon material preparation, and particularly relates to a polyether amine modified polyamide material and a preparation method thereof.
Background
Nylon (PA, a scientific name of polyamide) has been widely used in textile, automobile, electric, and mechanical parts because of its excellent properties such as high mechanical strength, wear resistance, and heat resistance. With the continuous improvement of the requirements on the service performance of the material, the research on the modification of the nylon material becomes the direction of the motivation of scientific researchers. The application of the traditional nylon materials to textile fibers has the defects of poor moisture absorption and air permeability, easy generation of static electricity and the like, which limits the application of the traditional nylon materials in certain fields.
In the common method for improving the moisture absorption, air permeability and antistatic property of the nylon fiber material in the prior art, the fabric is subjected to after-treatment or polyether chain segments are introduced into the nylon material to form a block copolymer, the problem of poor water washing resistance often exists in the after-treatment of the fabric, and the problem that the preparation steps are complicated and more pipelines and reaction kettles need to be cleaned when the production varieties are switched exist when the polyether chain segments are introduced into the nylon material to form the block copolymer, and the method needs to be further improved.
Disclosure of Invention
The invention aims to overcome the defects of the prior art and provide a polyether amine modified polyamide material with moisture absorption and antistatic effects, and also aims to provide a method for preparing the polyether amine modified polyamide material.
The invention adopts the following technical scheme:
the polyamide contains a chain segment formed by condensation polymerization of diisocyanate and bifunctional polyether amine, and the chain segment is terminated by using monofunctional polyether amine.
Further, the structural formula of the monofunctional polyether amine is shown as
Wherein x is 1, 6, 19 or 31Y is 3, 9, 10 or 29, and R is H or CH3。
Further, the monofunctional polyether amine is M-1000 and M-2070.
Further, the diisocyanate is one of toluene diisocyanate, 4-diphenylmethane diisocyanate, hexamethylene diisocyanate, isophorone diisocyanate, 2, 4-trimethylhexane diisocyanate, methylcyclohexyl diisocyanate, dicyclohexylmethane diisocyanate, naphthalene diisocyanate, p-phenylene diisocyanate, 1, 4-cyclohexane diisocyanate, xylylene diisocyanate, cyclohexanedimethylene diisocyanate, tetramethyl m-xylylene diisocyanate, norbornane diisocyanate, and dimethylbiphenyl diisocyanate.
Further, the structural formula of the bifunctional polyether amine is shown as
Where x is 2.5, 6.1, 33 or 68 or
Wherein x + z is 1.2, 3.6 or 6, and y is 2, 9, 12.5 or 39 or
Wherein x is 2 or 3.
Further, the bifunctional polyamide is D-2000, ED-900 or ED-2003.
Further, the polyamide is one of PA6, PA66, PA46, PA610, PA612, PA1010, PA11, PA12, PA6T and PA 9T.
A preparation method of a polyether amine modified polyamide material comprises the following steps:
step one, putting 1mol of bifunctional polyetheramine into a flask, and dehydrating for 1.8-2.2h in vacuum at 105-115 ℃;
step two, adding 1.001-2mol of diisocyanate into the dehydrated bifunctional polyether amine, introducing nitrogen, and reacting at 110-;
step three, taking 0.001-1mol of polyamide, firstly drying the polyamide in vacuum at the temperature of 115-125 ℃ for 3.5-4.5h, then adding the product obtained in the step two, introducing nitrogen, and carrying out melt reaction at the temperature of 250-270 ℃ for 1.5-2.5h to obtain-NCO-terminated polyetheramine modified polyamide;
step four, 0.001-1mol of monofunctional polyetheramine is dehydrated for 1.8-2.2h under vacuum at 105-115 ℃; and then mixing the polyamide with-NCO-terminated polyether amine modified polyamide obtained in the third step, introducing nitrogen for protection, and carrying out melt reaction for 1.5-2.5h at the temperature of 250-260 ℃ to obtain the polyether amine modified polyamide material.
Further, in the first step, the vacuum degree of vacuum dehydration is (-0.1 MPa).
As can be seen from the above description of the present invention, compared with the prior art, the beneficial effects of the present invention are: the polyether amine modified polyamide prepared by the invention contains a chain segment formed by condensation polymerization of diisocyanate and bifunctional polyether amine, and the chain segment is terminated by using monofunctional polyether amine, so that the surface resistivity of the prepared polyether amine modified polyamide is reduced, the moisture absorption rate is further improved, and the cantilever beam notch impact strength of the modified polyamide is obviously improved; the polyamide is modified on the conventional polyamide model, a main reaction kettle for polyamide polymerization does not need to be cleaned when the product variety is switched, and compared with a copolymerization production mode, the operation is convenient; the polyether amine modified polyamide prepared by the invention has the advantages of high mechanical strength, good toughness, good hydrophilic hygroscopicity, good antistatic performance and the like.
Detailed Description
The invention is further described below by means of specific embodiments.
The polyamide material modified with polyether amine has chain segment comprising diisocyanate and bifunctional polyether amine and terminated with monofunctional polyether amine.
The structural formula of the monofunctional polyether amine is shown in the specification
Wherein x is 1, 6, 19 or 31, y is 3, 9, 10 or 29, and R is H or CH3In particular, the monofunctional polyetheramine is
Series M-1000, M-2070.
The structural formula of the bifunctional polyether amine is shown in the specification
Where x is 2.5, 6.1, 33 or 68 or
Wherein x + z is 1.2, 3.6 or 6, and y is 2, 9, 12.5 or 39 or
Where x is 2 or 3, in particular difunctional polyamides are
Series D-2000, ED-900, ED-2003.
The diisocyanate is Toluene Diisocyanate (TDI), 4-diphenylmethane diisocyanate (MDI), Hexamethylene Diisocyanate (HDI), isophorone diisocyanate (IPDI), 2, 4-trimethylhexane diisocyanate (TMHDI), methylcyclohexyl diisocyanate (HTDI), dicyclohexylmethane diisocyanate (H)12MDI), Naphthalene Diisocyanate (NDI), p-phenylene diisocyanate (PPDI), 1, 4-cyclohexane diisocyanate (CHDI), Xylylene Diisocyanate (XDI), cyclohexanedimethylene diisocyanate (HXDI), tetramethylm-xylylene diisocyanate (TMXDI), norbornane diisocyanate (NBDI), and dimethylbiphenyl diisocyanate (TODI), and specifically, the diisocyanate is MDI, TDI, or HDI.
The polyamide is one of PA6, PA66, PA46, PA610, PA612, PA1010, PA11, PA12, PA6T and PA9T, specifically,
a preparation method of a polyether amine modified polyamide material comprises the following steps:
step one, 1mol of bifunctional polyether amine is put into a flask and dehydrated for 1.8 to 2.2 hours in the environment of 105-115 ℃ and vacuum degree (-0.1 MPa);
step two, adding 1.001-2mol of diisocyanate into the dehydrated bifunctional polyether amine, introducing nitrogen, and reacting at 110-;
step three, taking 0.001-1mol of polyamide, firstly drying the polyamide in vacuum at the temperature of 115-125 ℃ for 3.5-4.5h, then adding the product obtained in the step two, introducing nitrogen, and carrying out melt reaction at the temperature of 250-270 ℃ for 1.5-2.5h to obtain-NCO-terminated polyetheramine modified polyamide;
step four, 0.001-1mol of monofunctional polyetheramine is dehydrated for 1.8-2.2h under the environment of 105-115 ℃ and vacuum degree (-0.1 MPa); and then mixing the polyamide with-NCO-terminated polyether amine modified polyamide obtained in the third step, introducing nitrogen for protection, and carrying out melt reaction for 1.5-2.5h at the temperature of 250-260 ℃ to obtain the polyether amine modified polyamide material.
Example 1
A preparation method of a polyether amine modified polyamide material comprises the following steps:
putting 2000g ED-2003 into a four-neck flask with a vacuumizing device, and dehydrating for 2 hours at the temperature of 110 ℃ and under the vacuum degree (-0.1 MPa);
step two, 201.83g of HDI is added into 2000g of ED-2003 after vacuum dehydration, nitrogen is introduced for protection, and the temperature is maintained at 120 ℃ for reaction for 2 hours;
step three, taking 4.35kg of PA6 with the terminal amino group content of 46mmol/kg, drying for 4 hours at 120 ℃ in vacuum, then adding the product obtained in the step two, introducing nitrogen for protection, and carrying out melt reaction for 2 hours at 260 ℃ to obtain-NCO-terminated polyetheramine modified polyamide;
and step four, dehydrating 200g M-1000 for 2h at 110 ℃ and under the vacuum degree (-0.1MPa), adding the-NCO-terminated polyether amine modified polyamide obtained in the step three, introducing nitrogen for protection, and carrying out melt reaction for 2h at 260 ℃ to obtain the polyether amine modified polyamide material.
Example 2
A preparation method of a polyether amine modified polyamide material comprises the following steps:
putting 2000g ED-2003 into a four-neck flask with a vacuumizing device, and dehydrating for 2 hours at the temperature of 110 ℃ and under the vacuum degree (-0.1 MPa);
step two, 185.01g of HDI is added into 2000g of ED-2003 after vacuum dehydration, nitrogen is introduced for protection, and the temperature is maintained at 120 ℃ for reaction for 2 hours;
step three, taking 2.17kg of PA6 with the terminal amino group content of 46mmol/kg, vacuum-drying for 4 hours at 120 ℃, then adding the product obtained in the step two, introducing nitrogen for protection, and carrying out melt reaction for 2 hours at 260 ℃ to obtain-NCO-terminated polyetheramine modified polyamide;
and step four, dehydrating 100g M-1000 for 2h at 110 ℃ and under the vacuum degree (-0.1MPa), adding the-NCO-terminated polyether amine modified polyamide obtained in the step three, introducing nitrogen for protection, and carrying out melt reaction for 2h at 260 ℃ to obtain the polyether amine modified polyamide material.
Example 3
A preparation method of a polyether amine modified polyamide material comprises the following steps:
putting 2000g ED-2003 into a four-neck flask with a vacuumizing device, and dehydrating for 2 hours at the temperature of 110 ℃ and under the vacuum degree (-0.1 MPa);
step two, 252.29g of HDI is added into 2000g of ED-2003 after vacuum dehydration, nitrogen is introduced for protection, and the temperature is maintained at 120 ℃ for reaction for 2 hours;
step three, taking 10.87kg of PA6 with the terminal amino group content of 46mmol/kg, drying for 4 hours at 120 ℃ in vacuum, then adding the product obtained in the step two, introducing nitrogen for protection, and carrying out melt reaction for 2 hours at 260 ℃ to obtain-NCO-terminated polyetheramine modified polyamide;
and step four, dehydrating 500g M-1000 for 2h at 110 ℃ and under the vacuum degree (-0.1MPa), adding the-NCO-terminated polyether amine modified polyamide obtained in the step three, introducing nitrogen for protection, and carrying out melt reaction for 2h at 260 ℃ to obtain the polyether amine modified polyamide material.
Example 4
A preparation method of a polyether amine modified polyamide material comprises the following steps:
putting 2000g ED-2003 into a four-neck flask with a vacuumizing device, and dehydrating for 2 hours at the temperature of 110 ℃ and under the vacuum degree (-0.1 MPa);
and step two, 261.24g of TDI is added into 2000g of ED-2003 subjected to vacuum dehydration, nitrogen protection is introduced, and the temperature is maintained at 120 ℃ for reaction for 2 hours.
Step three, taking 10.87kg of PA6 with the terminal amino group content of 46mmol/kg, drying for 4 hours at 120 ℃ in vacuum, then adding the product obtained in the step two, introducing nitrogen for protection, and carrying out melt reaction for 2 hours at 260 ℃ to obtain-NCO-terminated polyetheramine modified polyamide;
and step four, dehydrating 500g M-1000 for 2h at 110 ℃ and under the vacuum degree (-0.1MPa), adding the-NCO-terminated polyether amine modified polyamide obtained in the step three, introducing nitrogen for protection, and carrying out melt reaction for 2h at 260 ℃ to obtain the polyether amine modified polyamide material.
Example 5
A preparation method of a polyether amine modified polyamide material comprises the following steps:
putting 2000g D-2000 into a four-neck flask with a vacuum extractor, and dehydrating for 2h at 110 ℃ under the vacuum degree (-0.1 MPa);
and step two, 252.29g of HDI is added into 2000g of ED-2003 after vacuum dehydration, nitrogen protection is introduced, and the temperature is maintained at 120 ℃ for reaction for 2 hours.
Step three, taking 10.87kg of PA6 with the terminal amino group content of 46mmol/kg, drying for 4 hours at 120 ℃ in vacuum, then adding the product obtained in the step two, introducing nitrogen for protection, and carrying out melt reaction for 2 hours at 260 ℃ to obtain-NCO-terminated polyetheramine modified polyamide;
and step four, dehydrating 500g M-1000 for 2h at 110 ℃ and under the vacuum degree (-0.1MPa), adding the-NCO-terminated polyether amine modified polyamide obtained in the step three, introducing nitrogen for protection, and carrying out melt reaction for 2h at 260 ℃ to obtain the polyether amine modified polyamide material.
Example 6
A preparation method of a polyether amine modified polyamide material comprises the following steps:
putting 2000g ED-2003 into a four-neck flask with a vacuumizing device, and dehydrating for 2 hours at the temperature of 110 ℃ and under the vacuum degree (-0.1 MPa);
and step two, 252.29g of HDI is added into 2000g of ED-2003 after vacuum dehydration, nitrogen protection is introduced, and the temperature is maintained at 120 ℃ for reaction for 2 hours.
Step three, taking 10kg of PA66 with the terminal amino group content of 50mmol/kg, vacuum-drying for 4 hours at 120 ℃, then adding the product obtained in the step two, introducing nitrogen for protection, and carrying out melt reaction for 2 hours at 260 ℃ to obtain-NCO-terminated polyetheramine modified polyamide;
and step four, dehydrating 500g M-1000 for 2h at 110 ℃ and under the vacuum degree (-0.1MPa), adding the-NCO-terminated polyether amine modified polyamide obtained in the step three, introducing nitrogen for protection, and carrying out melt reaction for 2h at 260 ℃ to obtain the polyether amine modified polyamide material.
Example 7
A preparation method of a polyether amine modified polyamide material comprises the following steps:
putting 900g ED-900 into a four-neck flask with a vacuumizing device, and dehydrating for 2 hours at the temperature of 110 ℃ and under the vacuum degree (-0.1 MPa);
and step two, 252.29g of HDI is added into 2000g of ED-2003 after vacuum dehydration, nitrogen protection is introduced, and the temperature is maintained at 120 ℃ for reaction for 2 hours.
Step three, taking 10.87kg of PA6 with the terminal amino group content of 46mmol/kg, drying for 4 hours at 120 ℃ in vacuum, then adding the product obtained in the step two, introducing nitrogen for protection, and carrying out melt reaction for 2 hours at 260 ℃ to obtain-NCO-terminated polyetheramine modified polyamide;
and step four, dehydrating 500g M-1000 for 2h at 110 ℃ and under the vacuum degree (-0.1MPa), adding the-NCO-terminated polyether amine modified polyamide obtained in the step three, introducing nitrogen for protection, and carrying out melt reaction for 2h at 260 ℃ to obtain the polyether amine modified polyamide material.
Example 8
A preparation method of a polyether amine modified polyamide material comprises the following steps:
putting 2000g ED-2003 into a four-neck flask with a vacuumizing device, and dehydrating for 2 hours at the temperature of 110 ℃ and under the vacuum degree (-0.1 MPa);
and step two, 252.29g of HDI is added into 2000g of ED-2003 after vacuum dehydration, nitrogen protection is introduced, and the temperature is maintained at 120 ℃ for reaction for 2 hours.
Step three, taking 10.87kg of PA6 with the terminal amino group content of 46mmol/kg, drying for 4 hours at 120 ℃ in vacuum, then adding the product obtained in the step two, introducing nitrogen for protection, and carrying out melt reaction for 2 hours at 260 ℃ to obtain-NCO-terminated polyetheramine modified polyamide;
and step four, dehydrating 1000g M-2070 for 2 hours at 110 ℃ under the vacuum degree (-0.1MPa), adding the-NCO-terminated polyether amine modified polyamide obtained in the step three, introducing nitrogen for protection, and carrying out melt reaction for 2 hours at 260 ℃ to obtain the polyether amine modified polyamide material.
Example 9
A preparation method of a polyether amine modified polyamide material comprises the following steps:
putting 900g ED-900 into a four-neck flask with a vacuumizing device, and dehydrating for 2.2 hours at 105 ℃ under the vacuum degree (-0.1 MPa);
and step two, 252.29g of HDI is added into 2000g of ED-2003 after vacuum dehydration, nitrogen protection is introduced, and the temperature is maintained at 110 ℃ for reaction for 2.2 hours.
Step three, taking 10.87kg of PA6 with the terminal amino group content of 46mmol/kg, drying for 3.5 hours at 125 ℃ in vacuum, then adding the product obtained in the step two, introducing nitrogen for protection, and carrying out melt reaction for 2.5 hours at 250 ℃ to obtain-NCO-terminated polyetheramine modified polyamide;
and step four, dehydrating 500g M-1000 for 2.2h at 105 ℃ under the vacuum degree (-0.1MPa), adding the-NCO-terminated polyether amine modified polyamide obtained in the step three, introducing nitrogen for protection, and carrying out melt reaction for 1.5h at 270 ℃ to obtain the polyether amine modified polyamide material.
Example 10
A preparation method of a polyether amine modified polyamide material comprises the following steps:
putting 900g ED-900 into a four-neck flask with a vacuumizing device, and dehydrating for 1.8h at 115 ℃ under the vacuum degree (-0.1 MPa);
step two, 252.29g of HDI was added into 2000g of ED-2003 after the vacuum dehydration, nitrogen gas was introduced for protection, and the temperature was maintained at 130 ℃ for reaction for 1.8 hours.
Step three, taking 10.87kg of PA6 with the terminal amino group content of 46mmol/kg, drying for 4.5 hours at 115 ℃ in vacuum, then adding the product obtained in the step two, introducing nitrogen for protection, and carrying out melt reaction for 1.5 hours at 270 ℃ to obtain-NCO-terminated polyetheramine modified polyamide;
and step four, dehydrating 500g M-1000 for 1.8h at 115 ℃ under the vacuum degree (-0.1MPa), adding the-NCO-terminated polyether amine modified polyamide obtained in the step three, introducing nitrogen for protection, and carrying out melt reaction for 2.5h at 250 ℃ to obtain the polyether amine modified polyamide material.
Comparing the performance of the polyetheramine modified polyamide materials prepared in examples 1-8 with conventional nylon 6 and nylon 66, the following data were obtained:
TABLE 1 comparison of the properties of the products obtained in examples 1-8 with conventional nylon 6 and nylon 66
As can be seen from table 1, the segment formed by condensation polymerization of diisocyanate and bifunctional polyetheramine improves the molecular weight of the polyetheramine modified polyamide, has good flexibility and strong hydrophilicity, reduces the surface resistivity of the prepared polyetheramine modified polyamide, further improves the moisture absorption rate, and significantly improves the notched izod impact strength of the modified polyamide.
Compared with polyamide in the prior art, the polyether amine modified polyamide prepared by the invention has the advantages of high mechanical strength, good toughness, good hydrophilic hygroscopicity and antistatic performance and the like.
The above description is only a preferred embodiment of the present invention, and therefore should not be taken as limiting the scope of the invention, which is defined by the appended claims and their equivalents and modifications within the scope of the description.
Claims (7)
1. A polyether amine modified polyamide material is characterized in that: the polyamide contains a chain segment formed by condensation polymerization of diisocyanate and bifunctional polyether amine, and the chain segment is terminated by using monofunctional polyether amine;
the structural formula of the monofunctional polyether amine is shown in the specification
Wherein x =1, 6, 19 or 31, y =3, 9, 10 or 29, and R is H or CH3；
The structural formula of the bifunctional polyether amine is shown in the specification
Wherein x =2.5, 6.1, 33 or 68 or
Wherein x + z =1.2, 3.6 or 6, y =2, 9, 12.5 or 39 or
Wherein x =2 or 3;
the preparation method comprises the following steps:
step one, putting 1mol of bifunctional polyetheramine into a flask, and dehydrating for 1.8-2.2h in vacuum at 105-115 ℃;
step two, adding 1.001-2mol of diisocyanate into the dehydrated bifunctional polyether amine, introducing nitrogen, and reacting at 110-;
step three, taking 0.001-1mol of polyamide, firstly drying the polyamide in vacuum at the temperature of 115-125 ℃ for 3.5-4.5h, then adding the product obtained in the step two, introducing nitrogen, and carrying out melt reaction at the temperature of 250-270 ℃ for 1.5-2.5h to obtain-NCO-terminated polyetheramine modified polyamide;
step four, 0.001-1mol of monofunctional polyetheramine is dehydrated for 1.8-2.2h under vacuum at 105-115 ℃; and then mixing the polyamide with-NCO-terminated polyether amine modified polyamide obtained in the third step, introducing nitrogen for protection, and carrying out melt reaction for 1.5-2.5h at the temperature of 250-260 ℃ to obtain the polyether amine modified polyamide material.
2. The polyether amine modified polyamide material as claimed in claim 1, wherein: the monofunctional polyether amine is M-1000 and M-2070.
3. The polyether amine modified polyamide material as claimed in claim 1, wherein: the diisocyanate is one of toluene diisocyanate, 4-diphenylmethane diisocyanate, hexamethylene diisocyanate, isophorone diisocyanate, 2, 4-trimethylhexane diisocyanate, methylcyclohexyl diisocyanate, dicyclohexylmethane diisocyanate, naphthalene diisocyanate, p-phenylene diisocyanate, 1, 4-cyclohexane diisocyanate, xylylene diisocyanate, cyclohexanedimethylene diisocyanate, tetramethyl m-xylylene diisocyanate, norbornane diisocyanate and dimethyl biphenyl diisocyanate.
4. The polyether amine modified polyamide material as claimed in claim 1, wherein: the bifunctional polyamide is D-2000, ED-900 or ED-2003.
5. The polyether amine modified polyamide material as claimed in claim 1, wherein: the polyamide is one of PA6, PA66, PA46, PA610, PA612, PA1010, PA11, PA12, PA6T and PA 9T.
6. A process for the preparation of the polyetheramine-modified polyamide material according to any one of claims 1 to 5, characterized in that: the method comprises the following steps:
step one, putting 1mol of bifunctional polyetheramine into a flask, and dehydrating for 1.8-2.2h in vacuum at 105-115 ℃;
step two, adding 1.001-2mol of diisocyanate into the dehydrated bifunctional polyether amine, introducing nitrogen, and reacting at 110-;
step three, taking 0.001-1mol of polyamide, firstly drying the polyamide in vacuum at the temperature of 115-125 ℃ for 3.5-4.5h, then adding the product obtained in the step two, introducing nitrogen, and carrying out melt reaction at the temperature of 250-270 ℃ for 1.5-2.5h to obtain-NCO-terminated polyetheramine modified polyamide;
step four, 0.001-1mol of monofunctional polyetheramine is dehydrated for 1.8-2.2h under vacuum at 105-115 ℃; and then mixing the polyamide with-NCO-terminated polyether amine modified polyamide obtained in the third step, introducing nitrogen for protection, and carrying out melt reaction for 1.5-2.5h at the temperature of 250-260 ℃ to obtain the polyether amine modified polyamide material.
7. The method for preparing a polyether amine modified polyamide material as claimed in claim 6, wherein: in the first step, the vacuum degree of vacuum dehydration is-0.1 MPa.
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