CN115652466B - Synergistic amidated light stabilizer for polyamide materials - Google Patents
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Abstract
The invention relates to the technical field of polyamide preparation, in particular to a synergistic compound amidation light stabilizer for a polyamide material, wherein the light stabilizer prepared by compounding an ultraviolet absorbent and a free radical trapping agent contains an amidation group which is highly compatible with the polyamide material, so that the ultraviolet absorbent and the free radical trapping agent can form strong polarity combination with polyamide molecules through amidation crosslinking, the polyamide breaking probability is favorably reduced, the thermal stability of the polyamide material can be effectively improved, and the light stabilizer can absorb ultraviolet light or contain a light stabilizing group, so that the anti-aging performance and the light stability of the polyamide material in the application process can be enhanced; in addition, the ultraviolet quenching agent in the stabilizing reinforcer can eliminate the photothermal excitation energy of the polyamide molecules and return the polyamide molecules to a low-energy state that molecular bonds cannot be broken, and the light shielding agent can absorb or reflect ultraviolet light, so that the ageing is effectively inhibited, and the photothermal stability of the polyamide material is improved.
Description
Technical Field
The invention relates to the technical field of polyamide preparation, in particular to a synergistic compound amidation light stabilizer for a polyamide material.
Background
Nylon is a term for polyamide fibers (chinlon), which can be made into long fibers or short fibers, and chinlon is the trade name of polyamide fibers and basically consists of aliphatic polyamides connected by amido bonds (— NHCO).
The polyamide fiber has excellent mechanical properties, tensile strength, compression strength and wear resistance, and the tensile strength of the polyamide fiber subjected to stretching and orientation treatment is higher and is close to the level of steel. The polyamide fiber has high crystallinity, large surface hardness, small friction coefficient and outstanding wear resistance and self-lubricating property, but the polyamide fiber has strong water absorption in the forming and processing process and poor stability in high-heat environment, and can be generally used only at 80-100 ℃, for example, the problems of yellowing of material color, surface pulverization and gradual reduction of mechanical property caused by long-term illumination and summer hot environment influence of the existing polyamide material in the long-term use process of products in the automobile industry.
Because the polyamide fiber has strong water absorption, the polyamide fiber needs to be dried before the polyamide fiber is formed, but the thermal stability of the material is poor, the thermal stability of the polyamide fiber material is greatly reduced at high temperature or in a molten state, and the degradation is easy to occur, so that the performance of the material is reduced; in addition, the polyamide fiber is easy to be oxidized, yellowed and aged under the action of light, heat and oxygen in the using process, so that the use value and the service life of the polyamide material are reduced. In order to improve the photo-thermal stability of the polyamide material during processing and use and simultaneously slow down the yellowing and aging rate of the material, a stabilizer capable of being compositely formulated with the polyamide material needs to be developed. In view of this, we propose synergistic built-up amidated light stabilizers for polyamide materials.
Disclosure of Invention
In order to remedy the above deficiencies, the present invention provides a synergistic built-in amidated light stabilizer for polyamide materials.
The technical scheme of the invention is as follows:
the synergistic amidation light stabilizer for polyamide material includes ultraviolet ray absorber and free radical scavenger, and also includes stabilizing reinforcer in 20 wt% of the light stabilizer, and the stabilizing reinforcer includes at least one of ultraviolet ray quenching agent and light shielding agent.
Preferably, the ultraviolet absorbent adopts oxamides, benzotriazoles and triazines organic compounds containing amidation groups, the oxamides, benzotriazoles and triazines organic compounds containing amidation groups can strongly and selectively absorb ultraviolet light with high energy, and release or consume the absorbed energy in the form of energy conversion by using heat energy or harmless low-energy radiation, and the organic compounds have high light resistance.
Preferably, the free radical trapping agent adopts a hindered amine derivative containing an amidation group, the hindered amine derivative has high thermal stability, and the hindered amine derivative can be connected with different free radicals, so that the photodegradation process is prevented or delayed.
Preferably, the ultraviolet quencher is an organic complex of nickel, and the ultraviolet quencher is capable of eliminating the photo-generated excitation energy on the polyamide molecules and returning the polyamide molecules to a low energy state in which the molecular bonds cannot be broken.
Preferably, the light-shielding agent comprises one or more of carbon black, zinc oxide and titanium dioxide which are uniformly mixed, the light-shielding agent can absorb or reflect ultraviolet light, a barrier can be arranged between light sources, light cannot pass through the light-shielding agent, but is directly absorbed or reflected by the light-shielding agent, and then ultraviolet rays are prevented from penetrating into the interior of the polyamide, so that the aging of the product is effectively inhibited.
Preferably, the light stabilizer accounts for 0.6-1.5% of the mass of the polyamide material and provides a light stabilizing effect.
Preferably, the mass part ratio of the ultraviolet absorbent to the free radical trapping agent is 40-80% to 40-80%.
Preferably, the ultraviolet absorber is any one of N- (2-ethoxyphenyl) -N '- (2-ethylbenzene base) -oxalamide, 2- (2' -hydroxy-3 ',5' -bis (a, a-dimethylbenzyl) phenyl) benzotriazole, poly { (6-morpholinyl-5-triazine-2,4-diyl) (2,2,6,6-tetramethylpiperidinyl) iminohexamethylene [ (2,2,6,6-tetramethylpiperidinyl) -imino ] }.
Preferably, the radical scavenger is any one of N, N' -bis (2,2,6,6-tetramethyl-4-piperidyl) -1,3-benzenedicarboxamide, poly (4-hydroxy-2,2,6,6-tetramethyl-1-piperidineethanol-ALT-1,4-butanedioic acid), poly { [6- [ (1,1,3,3-tetramethylbutyl) amino ] ] -1,3,5-triazine-2,4- [ (2,2,6,6, -tetramethyl-piperidyl) imino ] -1,6-hexanediene [ (2,2,6,6-tetramethyl-4-piperidyl) imino ] }.
Preferably, the particle size of the light shielding agent is 30-120 nm, the particle size influences the specific surface area, the particle size can be controlled to facilitate full dispersion, and the effect is improved.
Compared with the prior art, the invention has the beneficial effects that:
the light stabilizer is prepared by compounding the ultraviolet absorbent and the free radical trapping agent, and contains an amidation group which is highly compatible with the polyamide material, so that the ultraviolet absorbent and the free radical trapping agent can form strong polarity combination with polyamide molecules through amidation crosslinking, the polyamide breaking probability is favorably reduced, the thermal stability of the polyamide material can be effectively improved, and the light stabilizer contains a light stabilizing group which can absorb or block ultraviolet light, so that the anti-aging performance and the light stability of the polyamide material in the application process can be enhanced; in addition, the ultraviolet quenching agent in the stabilizing reinforcer can eliminate the photo-thermal excitation energy of polyamide molecules and return the polyamide molecules to a low-energy state that molecular bonds cannot be broken, and the light shielding agent can absorb or reflect ultraviolet light, so that aging is effectively inhibited, and the photo-thermal stability of the polyamide material is further improved.
Detailed Description
The technical solutions in the embodiments of the present invention will be clearly and completely described below, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
Example 1
The invention details the above technical solution by the following examples:
the synergistic amidation light stabilizer for polyamide material includes ultraviolet ray absorber and free radical trapping agent, and no stabilizer reinforcer is added.
The ultraviolet absorbent adopts oxamide, benzotriazole and triazine organic compounds containing amidation groups, the oxamide, benzotriazole and triazine organic compounds containing the amidation groups can strongly and selectively absorb high-energy ultraviolet light, and release or consume the absorbed energy in the form of energy conversion by using heat energy or harmless low-energy radiation, and the organic compounds have high light resistance.
The free radical trapping agent adopts hindered amine derivatives containing amidation groups, the hindered amine derivatives have high thermal stability, and the hindered amine derivatives can be connected with different free radicals, so that the photodegradation process is prevented or delayed.
The ultraviolet absorbent is any one of N- (2-ethoxyphenyl) -N '- (2-ethyl phenyl) -oxalamide, 2- (2' -hydroxy-3 ',5' -bis (a, a-dimethyl benzyl) phenyl) benzotriazole, poly { (6-morpholinyl-5-triazine-2,4-diyl) (2,2,6,6-tetramethyl piperidyl) imino hexamethylene [ (2,2,6,6-tetramethyl piperidyl) -imino ] }.
It is explained that N- (2-ethoxy phenyl) -N' - (2-ethyl phenyl) -oxalamide is a hindered amine light stabilizer with own polarity, is particularly effective to short-wave ultraviolet light, can strongly absorb ultraviolet light which is harmful to UVB, has good self-thermal stability, can be processed under the condition of high temperature, and cannot be decolorized when being contacted with metal ions; 2- (2 ' -hydroxy-3 ',5' -bis (a, a-dimethylbenzyl) phenyl) benzotriazole is a benzotriazole ultraviolet absorbent, has a photostability, can widely absorb 300-400nm ultraviolet rays, and has a small amount of absorption on visible spectrum; poly { (6-morpholinyl-5-triazine-2,4-diyl) (2,2,6,6-tetramethylpiperidyl) iminohexamethylene [ (2,2,6,6-tetramethylpiperidyl) -imino ] }, which contains a triazine group in addition to a hindered amine group, and is excellent in light stabilization effect.
The free radical trapping agent is any one of N, N' -bis (2,2,6,6-tetramethyl-4-piperidyl) -1,3-benzenedicarboxamide, poly (4-hydroxy-2,2,6,6-tetramethyl-1-piperidyl ethanol-ALT-1,4-butanedioic acid), poly { [6- [ (1,1,3,3-tetramethylbutyl) amino ] ] -1,3,5-triazine-2,4- [ (2,2,6,6, -tetramethyl-piperidyl) imino ] -1,6-hexanediene [ (2,2,6,6-tetramethyl-4-piperidyl) imino ] }.
It is to be explained that N, N' -bis (2,2,6,6-tetramethyl-4-piperidyl) -1,3-benzenedicarboxamide, a multifunctional light stabilizer suitable for polyamide materials, which contains an amide group, is highly compatible with polyamide, can bond with polyamide molecules to provide thermal stability to polyamide, and contains a polyamine-based basic group and an aromatic nitrogen group, can enhance the affinity of polyamide with metal dyes and acid dyes, and improve photo-thermal stability; the poly (4-hydroxy-2,2,6,6-tetramethyl-1-piperidine ethanol-ALT-1,4-succinic acid) has the characteristics of excellent processing thermal stability, low volatility, migration resistance, extraction resistance, gas fading resistance and the like, and has excellent long-acting light aging resistance; the poly { [6- [ (1,1,3,3-tetramethylbutyl) amino ] ] -1,3,5-triazine-2,4- [ (2,2,6,6, -tetramethyl-piperidyl) imino ] -1,6-hexamethylene [ (2,2,6,6-tetramethyl-4-piperidyl) imino ] } can effectively protect the polymer from being degraded by ultraviolet radiation and long-term thermal contact, and has the characteristics of excellent processing thermal stability, low volatility, migration resistance, extraction resistance, gas fading resistance and the like.
In this example, the light stabilizer accounts for 1% of the mass of the polyamide material, and the mass portion ratio between the mass of the ultraviolet absorber and the mass of the radical scavenger is 50% to 50%, specifically, 50g of N- (2-ethoxyphenyl) -N '- (2-ethylphenyl) -oxalamide is used as the ultraviolet absorber, and 50g of N, N' -bis (2,2,6,6-tetramethyl-4-piperidyl) -1,3-benzenedicarboxamide is used as the radical scavenger.
Example 2
This example differs from example 1 only in that: the mass part ratio of the ultraviolet absorbent to the free radical trapping agent is 80 percent to 40 percent; specifically, 80 g of N- (2-ethoxyphenyl) -N '- (2-ethylbenzene based) -oxalamide was used as an ultraviolet absorber, 40 g of N, N' -bis (2,2,6,6-tetramethyl-4-piperidyl) -1,3-benzenedicarboxamide was used as a radical scavenger, and the other conditions were the same.
Example 3
This example differs from example 1 only in that: the mass part ratio of the ultraviolet absorbent to the free radical trapping agent is 40 percent to 80 percent; specifically, 40 g of N- (2-ethoxyphenyl) -N '- (2-ethylphenyl) -ethanediamide was used as an ultraviolet absorber, 80 g of N, N' -bis (2,2,6,6-tetramethyl-4-piperidyl) -1,3-benzenedicarboxamide was used as a radical scavenger, and the other conditions were the same.
Example 4
This example differs from example 1 only in that: the mass part ratio of the ultraviolet absorbent to the free radical trapping agent is 60 percent to 40 percent; specifically, 60 g of N- (2-ethoxyphenyl) -N '- (2-ethylphenyl) -ethanediamide was used as an ultraviolet absorber, 40 g of N, N' -bis (2,2,6,6-tetramethyl-4-piperidyl) -1,3-benzenedicarboxamide was used as a radical scavenger, and the other conditions were the same.
Example 5
This example differs from example 1 only in that: the mass part ratio of the ultraviolet absorbent to the free radical trapping agent is 40 percent to 60 percent; specifically, 40 g of N- (2-ethoxyphenyl) -N '- (2-ethylphenyl) -ethanediamide was used as an ultraviolet absorber, 60 g of N, N' -bis (2,2,6,6-tetramethyl-4-piperidyl) -1,3-benzenedicarboxamide was used as a radical scavenger, and the other conditions were the same.
Example 6
This example differs from example 1 only in that: specifically, 50g of 2- (2 ' -hydroxy-3 ',5' -bis (a, a-dimethylbenzyl) phenyl) benzotriazole was used as an ultraviolet absorber, and the other conditions were the same.
Example 7
This example differs from example 1 only in that: specifically, 50g of poly { [6- [ (1,1,3,3-tetramethylbutyl) amino ] ] -1,3,5-triazine-2,4- [ (2,2,6,6, -tetramethyl-piperidyl) imino ] -1,6-hexamethylene [ (2,2,6,6-tetramethyl-4-piperidyl) imino ] } was used as a radical scavenger, and the other conditions were the same.
Example 8
This example differs from example 1 only in that: specifically, 50g of poly { (6-morpholinyl-5-triazine-2,4-diyl) (2,2,6,6-tetramethylpiperidinyl) iminohexamethylene [ (2,2,6,6-tetramethylpiperidinyl) -imino ] } was used as a radical scavenger, and the same other conditions were used, and it should be noted that poly { (6-morpholinyl-5-triazine-2,4-diyl) (2,2,6,6-tetramethylpiperidinyl) iminohexamethylene [ (2,2,6,6-tetramethylpiperidinyl) -imino ] } contains a hindered amine group and a triazine group in addition to the hindered amine group, so poly { (6-morpholinyl-5-triazine-2,4-diyl) (2,2,6,6-tetramethylpiperidinyl) iminohexamethylene [ (2,2,6,6-tetramethylpiperidinyl) -imino ] } is not only an ultraviolet absorber for triazine organic compounds, but also can be used as a hindered amine radical scavenger 323232323232323232323262.
Example 9
This example differs from example 1 only in that: specifically, 50g of poly (4-hydroxy-2,2,6,6-tetramethyl-1-piperidineethanol-ALT-1,4-butanedioic acid) is used as a free radical trapping agent, and other conditions are the same.
Example 10
This example differs from example 1 only in that: in this example 10, 20 g of a stabilizing reinforcing agent, 10 g of a light shielding agent having a particle size of 80 nm and 10 g of an organic complex of nickel were added, wherein carbon black, zinc oxide and titanium dioxide were uniformly mixed, and the other conditions were the same.
Comparative example 1
This comparative example differs from example 1 only in that: specifically, 50g of poly { [6- [ (1,1,3,3-tetramethylbutyl) amino ] ] -1,3,5-triazine-2,4- [ (2,2,6,6, -tetramethyl-piperidyl) imino ] -1,6-hexadiene [ (2,2,6,6-tetramethyl-4-piperidyl) imino ] } and 50g of 2- (2 ' -hydroxy-3 ',5' -bis (a, a-dimethylbenzyl) phenyl) benzotriazole were used, and the other conditions were the same.
Comparative example 2
This comparative example differs from example 1 only in that: specifically, 50g of poly { (6-morpholino-5-triazine-2,4-diyl) (2,2,6,6-tetramethylpiperidyl) iminohexamethylene [ (2,2,6,6-tetramethylpiperidyl) -imino ] } and 50g of 2- (2 ' -hydroxy-3 ',5' -bis (a, a-dimethylbenzyl) phenyl) benzotriazole were used, and the other conditions were the same.
Comparative example 3
The comparative example differs from example 1 only in that: specifically, 50g of poly (4-hydroxy-2,2,6,6-tetramethyl-1-piperidineethanol-ALT-1,4-butanedioic acid) and 50g of 2- (2 ' -hydroxy-3 ',5' -bis (a, a-dimethylbenzyl) phenyl) benzotriazole were used, and the other conditions were the same.
Comparative example 4
This example differs from example 1 in that no light stabilizer is added.
It is noted that the procedure for preparing the polyamide test specimens of examples 1 to 10 and comparative examples 1 to 4 was: adding a light stabilizer with the corresponding mass in the extrusion granulation process of the polyamide material, adding black master batch accounting for 1% of the mass of the polyamide material, uniformly mixing, carrying out twin-screw extrusion granulation according to the same extrusion process conditions, carrying out injection molding on the extruded particles according to the standard requirements of ISO4892-3 2016 to obtain test pieces, taking two test pieces for each polyamide material, and carrying out xenon lamp aging for 1000h according to ISO4892-3, and detecting the color difference change Delta E and the yellow index change Delta YI of the test pieces. The specific data are as follows:
from the above data it can be derived:
examples 1-5 used different mass ratios of N- (2-ethoxyphenyl) -N '- (2-ethylphenyl) -oxalamide as UV absorber, N' -bis (2,2,6,6-tetramethyl-4-piperidinyl) -1,3-benzenedicarboxamide as free radical scavenger, while examples 6-9 retained at least either N- (2-ethoxyphenyl) -N '- (2-ethylphenyl) -oxalamide or N, N' -bis (2,2,6,6-tetramethyl-4-piperidinyl) -1,3-benzenedicarboxamide, with another ingredient species being changed, comparative examples 1-3 used completely other light stabilizers than N- (2-ethoxyphenyl) -N '- (2-ethylphenyl) -oxalamide or N, N' -bis (2,2,6,6-tetramethyl-4-piperidinyl) -1,3-benzenedicarboxamide, as shown by the data in the above, comparative examples 1-9 and 1-3 used significantly improved resistance to UV light after the color difference of the addition of light stabilizer and the color difference of the light stabilizer to E and the change of comparative example 1-3; in addition, the stabilizing reinforcer is only added in the example 10, compared with the comparative example 4, the ultraviolet light aging resistance is also improved, but the improvement effect is not as good as that of the examples 1-9 and the comparative examples 1-3, so that the stabilizing reinforcer can be used as a supplement agent for further reinforcement;
in addition, the color difference change and the yellow index change of the polyamide materials added with the synergistic amidation light stabilizer are smaller than those of the comparative examples 1-3 after xenon lamp aging test, and therefore, the data can preferably adopt the light stabilizers as follows: n- (2-ethoxyphenyl) -N '- (2-ethylphenyl) -oxalamide as an ultraviolet absorbent and N, N' -bis (2,2,6,6-tetramethyl-4-piperidyl) -1,3-benzenedicarboxamide as a radical scavenger; the synergistic compounding of the two substances has excellent photo-thermal stability, the color difference change and the yellow index change fluctuation of the two substances under different proportions are small, the proportion can be reasonably adjusted according to the actual product price, and the ultraviolet light aging resistance of the polyamide material is remarkably improved by adding the light stabilizer.
The foregoing shows and describes the general principles, principal features, and advantages of the invention. It should be understood by those skilled in the art that the present invention is not limited to the above embodiments, and the above embodiments and descriptions are only preferred examples of the present invention and are not intended to limit the present invention, and that various changes and modifications may be made without departing from the spirit and scope of the present invention, which fall within the scope of the claimed invention. The scope of the invention is defined by the appended claims and equivalents thereof.
Claims (7)
1. A synergistic amidated light stabilizer for polyamide materials, characterized in that: the light stabilizer comprises an ultraviolet absorber and a free radical trapping agent, and further comprises a stability reinforcing agent which accounts for no more than 20 percent of the total mass of the light stabilizer, wherein the stability reinforcing agent at least comprises one of an ultraviolet quencher and a light shielding agent; the free radical trapping agent adopts hindered amine derivatives containing amidated groups, the ultraviolet absorbent is N- (2-ethoxyphenyl) -N '- (2-ethyl phenyl) -oxalamide, the free radical trapping agent is any one of N, N' -bis (2,2,6,6-tetramethyl-4-piperidyl) -1,3-benzenedicarboxamide, poly (4-hydroxy-2,2,6,6-tetramethyl-1-piperidyl ethanol-ALT-1,4-butanedioic acid), poly { [6- [ (1,1,3,3-tetramethylbutyl) amino ] ] -1,3,5-triazine-2,4- [ (2,2,6,6, -tetramethyl-piperidyl) imino ] -1,6-hexamethylene [ (2,2,6,6-tetramethyl-4-piperidyl) imino ] }, or the free radical scavenger is N, N ' -bis (2,2,6,6-tetramethyl-4-piperidyl) -1,3-benzenedicarboxamide, the ultraviolet absorbent is N- (2-ethoxyphenyl) -N ' - (2-ethylbenzene-yl) -oxalamide, 2- (2 ' -hydroxy-3 ',5' -bis (a, a-dimethylbenzyl) phenyl) benzotriazole, poly { (6-morpholinyl-5-triazine-2,4-diyl) (2,2,6,6-tetramethylpiperidyl) iminohexamethylene [ (2,2,6,6-tetramethylpiperidyl) -imino ] }.
2. The synergistically built amidated light stabilizer for polyamide materials according to claim 1, wherein: the ultraviolet absorbent adopts oxamides, benzotriazoles and triazine organic compounds containing amidation groups.
3. The synergistically built amidated light stabilizer for polyamide materials according to claim 2, wherein: the ultraviolet quencher adopts an organic complex of nickel.
4. A synergistically built amidated light stabilizer for polyamide materials according to claim 3, wherein: the light shielding agent comprises one or more of carbon black, zinc oxide and titanium dioxide which are uniformly mixed.
5. The synergistically built amidated light stabilizer for polyamide materials according to claim 4, wherein: the light stabilizer accounts for 0.6-1.5% of the mass of the polyamide material.
6. The synergistically built amidated light stabilizer for polyamide materials according to claim 5, wherein: the mass part ratio of the ultraviolet absorbent to the free radical trapping agent is 40-80% to 40-80%.
7. The synergistically built amidated light stabilizer for polyamide materials according to claim 6, wherein: the particle size of the shielding agent is 30-120 nanometers.
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