CN110016139A - A kind of Containing Schiff-bases hyperbranched polyorganosiloxane fire retardant and the preparation method and application thereof - Google Patents
A kind of Containing Schiff-bases hyperbranched polyorganosiloxane fire retardant and the preparation method and application thereof Download PDFInfo
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- CN110016139A CN110016139A CN201910256718.XA CN201910256718A CN110016139A CN 110016139 A CN110016139 A CN 110016139A CN 201910256718 A CN201910256718 A CN 201910256718A CN 110016139 A CN110016139 A CN 110016139A
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/06—Preparatory processes
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/22—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen
- C08G77/26—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen nitrogen-containing groups
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L77/00—Compositions of polyamides obtained by reactions forming a carboxylic amide link in the main chain; Compositions of derivatives of such polymers
- C08L77/02—Polyamides derived from omega-amino carboxylic acids or from lactams thereof
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2201/00—Properties
- C08L2201/02—Flame or fire retardant/resistant
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Abstract
The present invention relates to Containing Schiff-bases hyperbranched polyorganosiloxane fire retardant and the preparation method and application thereof, the structural formula of the Containing Schiff-bases hyperbranched polyorganosiloxane fire retardant is as follows:The preparation method of the Containing Schiff-bases hyperbranched polyorganosiloxane fire retardant includes: based on mole parts by weight, 10~20 parts of benzaldehyde, 10~20 parts of Amino End Group siloxanes, 60~80 parts of organic solvent are added in reaction vessel, it is passed through nitrogen displacement tainer air, desiccant is added, after reacting 5~8h at 50~80 DEG C, 5~10 parts of phenyl siloxane is added, reaction temperature is risen to 100~120 DEG C, after 3~5h of nitrogen reflux to obtain the final product.Then it by the Containing Schiff-bases hyperbranched polyorganosiloxane fire retardant of design synthesis, is added in the co-mixing system of nylon 6, in the case where a small amount of additive amount, can be prepared by Halogen, without molten drop, the good fire-retardant Nylon 6 composite material of flame retardant effect.
Description
Technical field
The invention belongs to fire retardant preparation and its application fields, in particular to the present invention relates to a kind of Containing Schiff-bases are hyperbranched
Polysiloxanes fire retardant and its preparing the application in fire-retardant no molten drop nylon 6 composite material.
Background technique
Nylon 6 is a kind of " general purpose grade " material, is widely used in textile garment and engineering plastics field, but it easily burns
Characteristic seriously limit nylon 6 in the application of some special dimensions.6 burning velocity of nylon is fast, and thermal discharge is high, and it is big to release smoke,
And in combustion with serious molten drop phenomenon, different degrees of injury is caused to human body and ecological environment.Especially
Molten drop phenomenon, easily ignite arround material, cause spot fire, and then expand fire range.Therefore, how molten drop is reduced at present
Have become the research hotspot and main direction of studying of numerous experts and scholars.
Patent CN 201610933669.5 relates to a kind of organic phosphorus fire-resistant copolyesters nylon composite and its preparation side
Method.It is characterized in that organic phosphorus, which is prepared, with caprolactam in organic phosphorus flame-retardant monomer or derivatives thereof is copolymerized fire-retardant gather
Amide, then gained is mixed with silicon systems inorganic nano material.Resulting organic phosphorus fire-resistant nylon composition is prepared, is prepared
Process viscosity is controllable, anti-molten drop excellent effect, and flame retardant property is outstanding.
Patent CN 201811060547.5 discloses a kind of halogen-free flame-retardant polyamide material, specifically adopts in polyamide
With polyimides/alkyl hypophosphites compound flame retardant of specific structure, and antioxidant and inorfil is added in certain condition
Lower melt blending, obtains novel flame-retardant polyamide material.The invention is under the conditions of adding less fire retardant, hence it is evident that improves polyamides
The flame retardant property of amine improves molten drop problem when burning.
Patent CN 201710496735.1 discloses a kind of preparation method of flame-retardant and anti-dripping polyamide film, the present invention
Magnesium hydroxide crystal whisker, aluminium borate whisker, calcium carbonate crystal whisker are handled with silane coupling agent in advance, after by caprolactam, nothing
Machine acid catalyst, binary acid, magnesium hydroxide crystal whisker, aluminium borate whisker, calcium carbonate crystal whisker, load have the aspartic acid-of chain extender
Proline-glutamicacid copolymer nano particle and water prepare gained after being uniformly mixed polymerization.
It can be seen that phosphorus flame retardant is still main research pair at present in the research field of flame-retardant and anti-dripping nylon 6
As, however phosphorus flame retardant is also easy to produce the toxic intermediate product such as phosphoric acid, metaphosphoric acid in combustion, and phosphorus flame retardant is logical
Normal heat resistance is poor, facile hydrolysis, therefore it is gradually unable to satisfy the growing processing and requirement in market.And when silicon systems,
When the fire retardants such as nitrogen system, metal are as fire proofing, in order to reach preferable flame retardant effect, commonly required biggish additive amount,
This will necessarily have an adverse effect to the bulk properties of nylon 6 material.Therefore few additive, efficient novel flame-retardant are developed
The key of agent necessarily 6 research field Future Development of flame-retardant and anti-dripping nylon.
Summary of the invention
Technical problem to be solved by the present invention lies in provide a kind of Containing Schiff-bases hyperbranched polyorganosiloxane fire retardant
(PCNSi) with fire-retardant no molten drop nylon 6 composite material and preparation method thereof.
In order to solve the above-mentioned technical problems, the present invention provides a kind of Containing Schiff-bases hyperbranched polyorganosiloxane fire retardant,
It is characterized in that, structural formula are as follows:
The R2 is aminoethyl propyl or propyl；R4For methyl or phenyl；The value range of the X is 1~10.
The present invention also provides a kind of preparation methods of Containing Schiff-bases hyperbranched polyorganosiloxane fire retardant (PCNSi), special
Sign is, comprising the following steps: based on mole parts by weight, by 10~20 parts of benzaldehyde, 10~20 parts of Amino End Group silicon oxygen
Alkane and 60~80 parts of organic solvents mixed dissolution under a nitrogen atmosphere, are added desiccant, in 50~80 DEG C of item after being sufficiently stirred
5~8h is reacted under part；Based on mole parts by weight, under a nitrogen atmosphere, 5~10 parts of phenyl siloxanes are added, it is warming up to 100~
120 DEG C, 3~5h is stirred to react to get Containing Schiff-bases hyperbranched polyorganosiloxane fire retardant (PCNSi) is arrived；Specific synthetic route is such as
Shown in Fig. 1.
Preferably, the Amino End Group siloxane structure formula are as follows:Wherein R1For methoxy or ethoxy,
R2Aminoethyl propyl or propyl.
Preferably, the phenyl siloxane structural formula are as follows:Wherein R3For methoxyl group, ethyoxyl what hydroxyl
Any one in base, R4It is independently selected from methyl or phenyl.
Preferably, the organic solvent is any one in ethyl alcohol, toluene, chloroform and acetone.
Preferably, the desiccant is any one in anhydrous magnesium sulfate, calcium oxide and barium hydroxide.
The present invention also provides above-mentioned Containing Schiff-bases hyperbranched polyorganosiloxane fire retardants to prepare fire-retardant no molten drop nylon 6 multiple
Application in condensation material.
Preferably, the Containing Schiff-bases hyperbranched polyorganosiloxane fire retardant is preparing fire-retardant no molten drop nylon 6 composite material
In application, which is characterized in that preparation method includes: in parts by weight, by 100 parts of nylon 6 slices, 2~6 parts of Containing Schiff-bases
Hyperbranched polyorganosiloxane fire retardant adds twin-screw extrude；The extruder temperature setting are as follows: one Qu Wendu: 200-220
℃；Two 200-220 DEG C of area's temperature；Three 220-240 DEG C of area's temperature；Four 220-240 DEG C of area's temperature；Five 220-240 DEG C of area's temperature, i.e.,
Obtain Containing Schiff-bases hyperbranched polyorganosiloxane fire-retardant Nylon 6 composite material.
Compared with prior art, the beneficial effects of the present invention are:
The hot property of Containing Schiff-bases hyperbranched polyorganosiloxane fire-retardant Nylon 6 composite material obtained and pure nylon in the present invention
6 is identical, and has the characteristics that flame retarding efficiency height, Halogen, low without molten drop, heat release amount.
Detailed description of the invention:
Fig. 1 is the synthetic route chart of the hyperbranched silicon-series five-retardant of Containing Schiff-bases (PCNSi) of the invention.
Fig. 2 is the synthetic route chart of the hyperbranched silicon-series five-retardant I (PCNSi) of Containing Schiff-bases in embodiment 1.
Fig. 3 is the synthetic route chart of the hyperbranched silicon-series five-retardant II (PCNSi) of Containing Schiff-bases in embodiment 1.
Fig. 4 is the synthetic route chart of the hyperbranched silicon-series five-retardant III (PCNSi) of Containing Schiff-bases in embodiment 1.
Fig. 5 is the synthetic route chart of the hyperbranched silicon-series five-retardant IV (PCNSi) of Containing Schiff-bases in embodiment 1.
Specific embodiment
Present invention will be further explained below with reference to specific examples.It should be understood that these embodiments are merely to illustrate the present invention
Rather than it limits the scope of the invention.In addition, it should also be understood that, after reading the content taught by the present invention, those skilled in the art
Member can make various changes or modifications the present invention, and such equivalent forms equally fall within the application the appended claims and limited
Range.
Embodiment 1
It present embodiments provides a kind of Containing Schiff-bases hyperbranched polyorganosiloxane fire retardant I (PCNSi) and Containing Schiff-bases is overspend
Change polysiloxanes fire-retardant Nylon 6 composite material I, specific preparation process is as follows:
Step 1: the preparation of Containing Schiff-bases hyperbranched polyorganosiloxane fire retardant (PCNSi):
As shown in Fig. 2, based on mole parts by weight, by 15 parts of benzaldehyde, the 1 of 15 parts, 3 aminopropyl triethoxysilanes
And 80 parts of ethyl alcohol mixed dissolution under a nitrogen atmosphere, 2 parts of anhydrous magnesium sulfates are added, are reacted under conditions of 80 DEG C after being sufficiently stirred
8h；Then based on mole parts by weight, under a nitrogen atmosphere, 10 parts of diphenyl silanols is added, is warming up to 120 DEG C, is stirred to react
5h to get arrive Containing Schiff-bases hyperbranched polyorganosiloxane fire retardant I；
Step 2: the preparation of Containing Schiff-bases hyperbranched polyorganosiloxane fire-retardant Nylon 6 composite material:
According to parts by weight, the Containing Schiff-bases hyperbranched polyorganosiloxane prepared by 100 parts of nylon 6 slices, 4 parts of steps 1 hinders
Combustion agent I adds twin-screw extrude, temperature setting are as follows: one Qu Wendu: 220 DEG C；Two 220 DEG C of area's temperature；Three area's temperature 240
℃；Four 240 DEG C of area's temperature；Five 240 DEG C of area's temperature hinder to get Halogen, without molten drop, fire-retardant Containing Schiff-bases hyperbranched polyorganosiloxane
Fire nylon 6 composite material I.
Containing Schiff-bases hyperbranched polyorganosiloxane fire-retardant Nylon 6 composite material I obtained heat release rate and is always released without molten drop
Heat reduces 81.3% and 82.5% compared to pure nylon 6 respectively.
Embodiment 2
It present embodiments provides a kind of Containing Schiff-bases hyperbranched polyorganosiloxane fire retardant II (PCNSi) and Containing Schiff-bases is overspend
Change polysiloxanes fire-retardant Nylon 6 composite material II, specific preparation process is as follows:
Step 1: the preparation of Containing Schiff-bases hyperbranched polyorganosiloxane fire retardant (PCNSi):
As shown in figure 3, based on mole parts by weight, by 10 parts of benzaldehyde, the 1 of 10 parts, 3 aminopropyl trimethoxysilanes
And 80 parts of toluene mixed dissolution under a nitrogen atmosphere, 2 parts of barium hydroxides are added, are reacted under conditions of 80 DEG C after being sufficiently stirred
8h；Then based on mole parts by weight, under a nitrogen atmosphere, 10 parts of aminomethyl phenyl silicon diols are added, are warming up to 120 DEG C, stirring
5h is reacted to get Containing Schiff-bases hyperbranched polyorganosiloxane fire retardant II is arrived；
Step 2: the preparation of Containing Schiff-bases hyperbranched polyorganosiloxane fire-retardant Nylon 6 composite material:
According to parts by weight, the Containing Schiff-bases hyperbranched polyorganosiloxane prepared by 100 parts of nylon 6 slices, 4 parts of steps 1 hinders
Combustion agent II adds twin-screw extrude, temperature setting are as follows: one Qu Wendu: 230 DEG C；Two 230 DEG C of area's temperature；Three area's temperature 240
℃；Four 240 DEG C of area's temperature；Five 240 DEG C of area's temperature hinder to get Halogen, without molten drop, fire-retardant Containing Schiff-bases hyperbranched polyorganosiloxane
Fire nylon 6 composite material II.
Containing Schiff-bases hyperbranched polyorganosiloxane fire-retardant Nylon 6 composite material II obtained is without molten drop, heat release rate and total
Heat release amount reduces 75.3% and 72.5% compared to pure nylon 6 respectively.
Embodiment 3
It present embodiments provides a kind of Containing Schiff-bases hyperbranched polyorganosiloxane fire retardant III (PCNSi) and Containing Schiff-bases is overspend
Change polysiloxanes fire-retardant Nylon 6 composite material III, specific preparation process is as follows:
Step 1: the preparation of Containing Schiff-bases hyperbranched polyorganosiloxane fire retardant (PCNSi):
As shown in figure 4, based on mole parts by weight, by 10 parts of benzaldehyde, 10 parts of γ-aminoethylaminopropyl trimethoxy
Base silane and 80 parts of chloroforms mixed dissolution under a nitrogen atmosphere, are added 2 parts of calcium oxide, anti-under conditions of 60 DEG C after being sufficiently stirred
Answer 8h；Then based on mole parts by weight, under a nitrogen atmosphere, 10 parts of dimethoxydiphenylsilanes is added, are warming up to 100
DEG C, 5h is stirred to react to get Containing Schiff-bases hyperbranched polyorganosiloxane fire retardant III is arrived；
Step 2: the preparation of Containing Schiff-bases hyperbranched polyorganosiloxane fire-retardant Nylon 6 composite material:
According to parts by weight, the Containing Schiff-bases hyperbranched polyorganosiloxane prepared by 100 parts of nylon 6 slices, 3 parts of steps 1 hinders
Combustion agent III adds twin-screw extrude, temperature setting are as follows: one Qu Wendu: 230 DEG C；Two 230 DEG C of area's temperature；Three area's temperature 230
℃；Four 230 DEG C of area's temperature；Five 240 DEG C of area's temperature hinder to get Halogen, without molten drop, fire-retardant Containing Schiff-bases hyperbranched polyorganosiloxane
Fire nylon 6 composite material III.
Containing Schiff-bases hyperbranched polyorganosiloxane fire-retardant Nylon 6 composite material III obtained is without molten drop, heat release rate and total
Heat release amount reduces 79.1% and 75.3% compared to pure nylon 6 respectively.
Embodiment 4
It present embodiments provides a kind of Containing Schiff-bases hyperbranched polyorganosiloxane fire retardant IV (PCNSi) and Containing Schiff-bases is overspend
Change polysiloxanes fire-retardant Nylon 6 composite material IV, specific preparation process is as follows:
Step 1: the preparation of Containing Schiff-bases hyperbranched polyorganosiloxane fire retardant (PCNSi):
As shown in figure 5, based on mole parts by weight, by 10 parts of benzaldehyde, 10 parts of gamma-aminopropyl-triethoxy-silane
And 80 parts of acetone mixed dissolution under a nitrogen atmosphere, 2 parts of anhydrous magnesium sulfates are added, are reacted under conditions of 80 DEG C after being sufficiently stirred
6h；Then based on mole parts by weight, under a nitrogen atmosphere, 10 parts of diphenyl diethoxy silanes is added, are warming up to 110 DEG C,
5h is stirred to react to get Containing Schiff-bases hyperbranched polyorganosiloxane fire retardant IV is arrived；
Step 2: preparation of the Halogen without molten drop fire-retardant Nylon 6 composite material:
According to the mass fraction, the Containing Schiff-bases hyperbranched polyorganosiloxane prepared by 100 parts of nylon 6 slices, 6 parts of steps 1 hinders
Combustion agent IV adds twin-screw extrude, temperature setting are as follows: one Qu Wendu: 230 DEG C；Two 230 DEG C of area's temperature；Three area's temperature 230
℃；Four 230 DEG C of area's temperature；Five 240 DEG C of area's temperature hinder to get Halogen, without molten drop, fire-retardant Containing Schiff-bases hyperbranched polyorganosiloxane
Fire nylon 6 composite material IV.
Containing Schiff-bases hyperbranched polyorganosiloxane fire-retardant Nylon 6 composite material IV obtained is without molten drop, heat release rate and total
Heat release amount reduces 85.1% and 85.3% compared to pure nylon 6 respectively.
Claims (8)
1. a kind of Containing Schiff-bases hyperbranched polyorganosiloxane fire retardant, which is characterized in that its structural formula are as follows:
The R2 is aminoethyl propyl or propyl；R4For methyl or phenyl；The value range of the X is 1~10.
2. the preparation method of Containing Schiff-bases hyperbranched polyorganosiloxane fire retardant described in claim 1, which is characterized in that including following
Step: based on mole parts by weight, 10~20 parts of benzaldehyde, 10~20 parts of Amino End Group siloxanes and 60~80 parts are organic
Mixed dissolution, addition desiccant react 5~8h to solvent under conditions of 50~80 DEG C under a nitrogen atmosphere after being sufficiently stirred；It presses
Molal weight number meter is added 5~10 parts of phenyl siloxanes, is warming up to 100~120 DEG C, is stirred to react 3 under a nitrogen atmosphere
~5h to get arrive Containing Schiff-bases hyperbranched polyorganosiloxane fire retardant.
3. the preparation method of Containing Schiff-bases hyperbranched polyorganosiloxane fire retardant as claimed in claim 2, which is characterized in that the end
Amino silicone structural formula are as follows:Wherein R1For methoxy or ethoxy, R2For aminoethyl propyl or propyl.
4. the preparation method of Containing Schiff-bases hyperbranched polyorganosiloxane fire retardant as claimed in claim 2, which is characterized in that the benzene
Radical siloxane structural formula are as follows:Wherein R3For any one in methoxyl group, ethyoxyl and hydroxyl, R4For first
Base or phenyl.
5. the preparation method of Containing Schiff-bases hyperbranched polyorganosiloxane fire retardant as claimed in claim 2, which is characterized in that described to have
Solvent is any one in ethyl alcohol, toluene, chloroform and acetone.
6. the preparation method of Containing Schiff-bases hyperbranched polyorganosiloxane fire retardant as claimed in claim 2, which is characterized in that described dry
Drying prescription is any one in anhydrous magnesium sulfate, calcium oxide and barium hydroxide.
7. a kind of Containing Schiff-bases hyperbranched polyorganosiloxane fire retardant described in claim 1 is to prepare fire-retardant no molten drop nylon 6 multiple
Application in condensation material.
8. Containing Schiff-bases hyperbranched polyorganosiloxane fire retardant as claimed in claim 7 is to prepare fire-retardant no molten drop nylon 6 compound
Application in material, which is characterized in that according to parts by weight, by 100 parts of nylon 6 slices, 2~6 parts of Containing Schiff-bases hyperbranched polies
Siloxane flame retardant adds twin-screw extrude；The extruder temperature setting are as follows: one Qu Wendu: 200-220 DEG C；Two area's temperature
200-220 DEG C of degree；Three 220-240 DEG C of area's temperature；Four 220-240 DEG C of area's temperature；Five 220-240 DEG C of area's temperature are to get schiff bases
Base hyperbranched polyorganosiloxane fire-retardant Nylon 6 composite material.
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Cited By (7)
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| CN110606990A (en) * | 2019-09-11 | 2019-12-24 | 东华大学 | Hyperbranched polysiloxane-coated ammonium polyphosphate flame retardant and preparation method thereof |
| CN110656394A (en) * | 2019-10-23 | 2020-01-07 | 东华大学 | Schiff base P-N-Si flame-retardant PA6, fiber and preparation method thereof |
| CN110746651A (en) * | 2019-10-23 | 2020-02-04 | 东华大学 | Aromatic Schiff base hyperbranched polysiloxane coated modified ammonium polyphosphate |
| CN112921647A (en) * | 2021-02-25 | 2021-06-08 | 嘉兴学院 | Anti-dripping finishing method for terylene |
| CN113201139A (en) * | 2021-03-24 | 2021-08-03 | 浙江理工大学 | Novel P-N-Si flame-retardant anti-dripping agent, anti-dripping PA6 material and preparation methods thereof |
| CN113880734A (en) * | 2021-11-08 | 2022-01-04 | 苏州大学 | Functional caramel and application thereof as flame-retardant finishing agent |
| CN116987262A (en) * | 2022-04-26 | 2023-11-03 | 中国科学院化学研究所 | Nylon, anti-dripping flame-retardant material containing nylon and preparation method |
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| CN110746651A (en) * | 2019-10-23 | 2020-02-04 | 东华大学 | Aromatic Schiff base hyperbranched polysiloxane coated modified ammonium polyphosphate |
| CN110746651B (en) * | 2019-10-23 | 2021-07-20 | 东华大学 | Aromatic Schiff base hyperbranched polysiloxane coated modified ammonium polyphosphate |
| CN110656394B (en) * | 2019-10-23 | 2021-08-10 | 东华大学 | Schiff base P-N-Si flame-retardant PA6, fiber and preparation method thereof |
| CN112921647A (en) * | 2021-02-25 | 2021-06-08 | 嘉兴学院 | Anti-dripping finishing method for terylene |
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| CN113880734A (en) * | 2021-11-08 | 2022-01-04 | 苏州大学 | Functional caramel and application thereof as flame-retardant finishing agent |
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