CN106893369A - A kind of synthesis of phosphorous nitrogen sulfur compound and its preparation method of intercalation modifying hydrotalcite - Google Patents
A kind of synthesis of phosphorous nitrogen sulfur compound and its preparation method of intercalation modifying hydrotalcite Download PDFInfo
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- CN106893369A CN106893369A CN201710037467.7A CN201710037467A CN106893369A CN 106893369 A CN106893369 A CN 106893369A CN 201710037467 A CN201710037467 A CN 201710037467A CN 106893369 A CN106893369 A CN 106893369A
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09C—TREATMENT OF INORGANIC MATERIALS, OTHER THAN FIBROUS FILLERS, TO ENHANCE THEIR PIGMENTING OR FILLING PROPERTIES ; PREPARATION OF CARBON BLACK ; PREPARATION OF INORGANIC MATERIALS WHICH ARE NO SINGLE CHEMICAL COMPOUNDS AND WHICH ARE MAINLY USED AS PIGMENTS OR FILLERS
- C09C1/00—Treatment of specific inorganic materials other than fibrous fillers; Preparation of carbon black
- C09C1/40—Compounds of aluminium
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
- C08K3/24—Acids; Salts thereof
- C08K3/26—Carbonates; Bicarbonates
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K9/00—Use of pretreated ingredients
- C08K9/04—Ingredients treated with organic substances
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09C—TREATMENT OF INORGANIC MATERIALS, OTHER THAN FIBROUS FILLERS, TO ENHANCE THEIR PIGMENTING OR FILLING PROPERTIES ; PREPARATION OF CARBON BLACK ; PREPARATION OF INORGANIC MATERIALS WHICH ARE NO SINGLE CHEMICAL COMPOUNDS AND WHICH ARE MAINLY USED AS PIGMENTS OR FILLERS
- C09C3/00—Treatment in general of inorganic materials, other than fibrous fillers, to enhance their pigmenting or filling properties
- C09C3/08—Treatment with low-molecular-weight non-polymer organic compounds
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Abstract
Synthesis and its preparation method of intercalation modifying hydrotalcite the present invention relates to a kind of phosphorous nitrogen sulfur compound, belong to nano clay orgnic-intercalation modification field.The reaction monomers containing phosphorus, nitrogen, sulphur are carried out into intercalation compound BTP of the reaction generation with fire resistance first；At 80~100 DEG C, under mechanical agitation, hydrotalcite is formed uniform emulsion in deionized water, then the saturated aqueous solution of BTP is added in above-mentioned emulsion, BTP molecular replacements go out hydrotalcite interlayer anion and are intercalation into hydrotalcite layers.The purpose of the present invention is will be phosphorous, the ignition-proof elements such as nitrogen, sulphur are intercalation into hydrotalcite layers, while increasing the interlamellar spacing of hydrotalcite, a kind of hydrotalcite of new phosphorus nitrogen sulfur compound intercalation modifying is obtained, so as to improve hydrotalcite fire-retardant, dispersion in the base and the performance such as compatible.
Description
Technical field
The present invention relates to a kind of hydrotalcite-modified field, and in particular to a kind of synthesis of phosphorous nitrogen sulfur compound and its intercalation
The preparation method of modified hydrotalcite.
Background technology
Hydrotalcite (LDHs) is a kind of anionic clay, and its general molecular formula isWherein MⅡ
It is Mg2+,Ni2+,Zn2+Deng divalent metal；MⅢIt is Al3+,Fe3+,Cr3+Deng trivalent metal cation；An-For interlayer is balanced
Anion, such asAnd Cl-Deng.It is usually used in the fire-retardant of polymer because it has the functions such as fire-retardant, suppression cigarette, filling.By
The interchangeability of anion between neatly stone veneer, can by some contain the molecule intercalation of ignition-proof element to hydrotalcite layers from
And improve its fire resistance.
Synthesized phosphorous nitrogen sulfur compound BTP in the present invention, contains a sulfonic group and a phosphorus hydroxyl in molecule, its
Acidity is better than CO3 2-, can be by displacing the CO of LDHs interlayers3 2-And it is introduced in LDHs interlayers.Due to the molecular volume of BTP
More than CO3 2-Ion, so can effectively increase the interlamellar spacing of LDHs after BTP is intercalation into LDHs interlayers, so that the molecule of organic matter
Segment is easier to enter into LDHs interlayers, and BTP is organic group in addition, can improve the compatibility with organic matter.In BTP molecules
P, N, S element can also improve its fire resistance.
The content of the invention
The purpose of the present invention contains P simultaneously to prepare one kind, and the hydrotalcite of the compound intercalation of N, S element is expanding
Ignition-proof element is introduced while LDHs interlamellar spacings, so as to improve the anti-flammability and its compatibility with organic matter matrix of LDHs.
To achieve the above object, the present invention is adopted the following technical scheme that：
A kind of synthesis of phosphorous nitrogen sulfur compound and its preparation method of intercalation modifying hydrotalcite, its feature include following step
Suddenly：The reaction monomers containing phosphorus, nitrogen, sulphur are carried out into reaction intercalation compound (BTP) of the generation with fire resistance first, then
By in hydrotalcite addition deionized water, slurries are made under mechanical agitation, then the saturated aqueous solution of BTP is added to above-mentioned slurries
In, by ion-exchange by BTP molecule intercalations to hydrotalcite layers.
The synthesis of the phosphorous nitrogen sulfur compound described in step of the present invention and its preparation method of intercalation modifying hydrotalcite, it is special
It is that BTP is oneself synthesis to levy, will nitrogenous sulphur monomer (taurine, sulfamic acid, p-aminobenzene sulfonic acid etc.) and equimolar matter
The aldehydes (benzaldehyde, salicylide, 3- tolyl aldehydes, parahydroxyben-zaldehyde, formaldehyde, acetaldehyde etc.) of amount, solvent, 25 are done in ethanol
3~8h is reacted at~60 DEG C and obtains nitrogen sulphur schiff bases (BT).Then by BT and phosphorous-containing monomers (hypophosphorous acid, phosphorous of equimolar quality
Diethyl phthalate, dimethylphosphite, methyl hypophosphorous acid ethyl ester, methyl hypophosphorous acid methyl esters etc.), do solvent, 25~60 DEG C in methyl alcohol
10~15h of lower reaction obtains BTP.
The synthesis of the phosphorous nitrogen sulfur compound described in step of the present invention and its preparation method of intercalation modifying hydrotalcite, it is special
Levy is that hydrotalcite used is magnalium carbonate hydrotalcite, magnalium nitrate anion hydrotalcite, zinc-aluminium carbonate hydrotalcite, zinc-aluminium nitric acid
Root hydrotalcite, nickel aluminium carbonate hydrotalcite, nickel aluminium nitrate anion hydrotalcite etc..
The synthesis of the phosphorous nitrogen sulfur compound described in step of the present invention and its preparation method of intercalation modifying hydrotalcite, it is special
It is hydrotalcite to levy and the mass ratio of deionized water is 1:2~1:20, temperature control at 80~100 DEG C, the reaction time is 1~
6h.The quality of BTP is controlled 2~3 with the mass ratio of hydrotalcite in 1~10, PH, and reaction temperature is 80~100 DEG C, reaction time
It is 1~6h, mechanical agitation.
The present invention is prepared for a kind of organically-modified hydrotalcite of new interlayer, and phosphorous nitrogen sulfur compound (BTP) is intercalation into water
Talcum interlayer, raw materials for production are easy to get, high conversion rate, process is simple, process environmental protection, can effectively improve the fire resistance of polymer.
Modified hydrotalcite prepared by the present invention has the following advantages that, in production application, hydrotalcite prepared by the present invention can
With macromolecule matrix blending, so as to obtain organic/inorganic composite material, hydrotalcite after modified can improve it in the base
Dispersiveness and compatibility, while can also improve the fire-retardant and mechanical property of matrix.
Brief description of the drawings
Fig. 1 is a kind of chemical equation of synthesis BTP provided in an embodiment of the present invention.
Fig. 2 is a kind of infrared analysis figure of synthesis BTP provided in an embodiment of the present invention.
Fig. 3 is a kind of infrared analysis figure of intercalated houghite provided in an embodiment of the present invention.
Fig. 4 is a kind of XRD analysis figure of intercalated houghite provided in an embodiment of the present invention.
Specific embodiment
Below in conjunction with the accompanying drawings and embodiment the invention will be further described：
Embodiment 1：
(1) 12.5g taurines are taken and 4g NaOH is dissolved in 250mL ethanol, after 50 DEG C of magnetic agitation reaction 30min,
10.6g benzaldehyde solutions are slowly added to, continue to react 5h, taurine-benzaldehyde schiff bases is dried to obtain in filtering, ethanol washing
(BT)。
(2) take 0.66g hypophosphorous acid and a small amount of trim,ethylchlorosilane is dissolved in 50mL methyl alcohol, 50 DEG C of magnetic agitations react 2h, then
2.35gBT is added, continues to react 13h.Filtering, ethanol washing, the compound (BTP) of dry product phosphorus-nitrogen containing sulphur.
(3) take 10g hydrotalcites to be added in the there-necked flask of the 250mL for filling 100mL distilled water, at 90 DEG C, machinery is stirred
2h is mixed, after uniform emulsion to be formed, adds the saturated aqueous solution of BTP until system is there is no bubble, continue that BTP saturations are added dropwise
The aqueous solution, control PH continues to react 2h in 2-3.Filtering, distills water washing, dries to obtain BTP intercalation modifying hydrotalcites (BTP-
LDH)。
(4) infrared analysis is carried out to the intercalator BTP for synthesizing, in 1645cm in BT-1Place occurs in that C=N peaks, illustrates ox sulphur
Acid successfully reacts to form BT schiff bases with benzaldehyde.C=N peaks disappear in BTP, 1183 and 984cm-1Place, occurs in that P=O, P-O
Peak, illustrates that BT successfully reacts generation BTP with hypophosphorous acid.
(5) infrared analysis is carried out to intercalation modifying hydrotalcite and unmodified hydrotalcite, 1387cm in BTP-LDH-1Place CO3 2-
Characteristic peak disappear, 1635,1161,1046cm-1Place occurs in that the characteristic peak of BTP, illustrates that BTP successfully replaces out hydrotalcite layer
Between CO3 2And it is intercalation into hydrotalcite layers.
(6) in order to further verify, XRD analysis are carried out to intercalation modifying hydrotalcite and unmodified hydrotalcite.Can from figure
To find out, compared with unmodified LDH, the position of crystallographic plane diffraction peak is moved to low angle in BTP-LDH molecules, is illustrated with BTP
Substitution CO3 2-, cause interplanar distance to expand.(003), (006), the angle of diffraction of (009) crystal face respectively from 11.44 ° in LDH,
23.3 °, 34.62 ° of 4.41 ° moved left in BTP-LDH, 13.27 °, according to Bragg diffraction formulas, illustrate interlamellar spacing d by 8.79 °
(003) 2.01nm is increased to by 0.77nm.(110) peak of other hydrotalcite does not find significant change, in illustrating BTP modifying process
Veneer structure without destruction hydrotalcite.So BTP is successfully intercalation into hydrotalcite layers, and expand the interlamellar spacing of hydrotalcite.
Embodiment 2：
(1) 12.5g taurines are taken and 4g NaOH is dissolved in 250mL ethanol, magnetic agitation reaction 30min at 25 DEG C
Afterwards, 10.6g benzaldehyde solutions are slowly added to, continue to react 3h, taurine-benzaldehyde schiff bases is dried to obtain in filtering, ethanol washing
(BT)。
(2) take 0.66g hypophosphorous acid and a small amount of trim,ethylchlorosilane is dissolved in 50mL methyl alcohol, 25 DEG C of magnetic agitations react 2h, then
2.35gBT is added, continues to react 10h.Filtering, ethanol washing, the compound (BTP) of dry product phosphorus-nitrogen containing sulphur.
(3) take 10g hydrotalcites to be added in the there-necked flask of the 250mL for filling 100mL distilled water, at 80 DEG C, machinery is stirred
1h is mixed, after uniform emulsion to be formed, adds the saturated aqueous solution of BTP until system is there is no bubble, continue that BTP saturations are added dropwise
The aqueous solution, control PH continues to react 1h in 2-3.Filtering, distills water washing, dries to obtain BTP intercalation modifying hydrotalcites (BTP-
LDH)。
Embodiment 3：
(1) 12.5g taurines are taken and 4g NaOH is dissolved in 250mL ethanol, after 60 DEG C of magnetic agitation reaction 30min,
10.6g benzaldehyde solutions are slowly added to, continue to react 8h, taurine-benzaldehyde schiff bases is dried to obtain in filtering, ethanol washing
(BT)。
(2) take 0.66g hypophosphorous acid and a small amount of trim,ethylchlorosilane is dissolved in 50mL methyl alcohol, 60 DEG C of magnetic agitations react 2h, then
2.35gBT is added, continues to react 15h.Filtering, ethanol washing, the compound (BTP) of dry product phosphorus-nitrogen containing sulphur.
(3) take 10g hydrotalcites to be added in the there-necked flask of the 250mL for filling 100mL distilled water, at 100 DEG C, machinery is stirred
6h is mixed, after uniform emulsion to be formed, adds the saturated aqueous solution of BTP until system is there is no bubble, continue that BTP saturations are added dropwise
The aqueous solution, control PH continues to react 6h in 2-3.Filtering, distills water washing, dries to obtain BTP intercalation modifying hydrotalcites (BTP-
LDH)。
Embodiment 4：
(1) 12.5g taurines are taken and 4g NaOH is dissolved in 250mL ethanol, after 25 DEG C of magnetic agitation reaction 30min,
10.6g benzaldehyde solutions are slowly added to, continue to react 8h, taurine-benzaldehyde schiff bases is dried to obtain in filtering, ethanol washing
(BT)。
(2) take 0.66g hypophosphorous acid and a small amount of trim,ethylchlorosilane is dissolved in 50mL methyl alcohol, 60 DEG C of magnetic agitations react 2h, then
2.35gBT is added, continues to react 15h.Filtering, ethanol washing, the compound (BTP) of dry product phosphorus-nitrogen containing sulphur.
(3) take 10g hydrotalcites to be added in the there-necked flask of the 250mL for filling 100mL distilled water, at 80 DEG C, machinery is stirred
2h is mixed, after uniform emulsion to be formed, adds the saturated aqueous solution of BTP until system is there is no bubble, continue that BTP saturations are added dropwise
The aqueous solution, control PH continues to react 1h in 2-3.Filtering, distills water washing, dries to obtain BTP intercalation modifying hydrotalcites (BTP-
LDH)。
Embodiment 5：
(1) 12.5g taurines are taken and 4g NaOH is dissolved in 250mL ethanol, after 60 DEG C of magnetic agitation reaction 30min,
10.6g benzaldehyde solutions are slowly added to, continue to react 10h, taurine-benzaldehyde schiff bases is dried to obtain in filtering, ethanol washing
(BT)。
(2) take 0.66g hypophosphorous acid and a small amount of trim,ethylchlorosilane is dissolved in 50mL methyl alcohol, 25 DEG C of magnetic agitations react 2h, then
2.35gBT is added, continues to react 15h.Filtering, ethanol washing, the compound (BTP) of dry product phosphorus-nitrogen containing sulphur.
(3) take 10g hydrotalcites to be added in the there-necked flask of the 250mL for filling 100mL distilled water, at 100 DEG C, machinery is stirred
2h is mixed, after uniform emulsion to be formed, adds the saturated aqueous solution of BTP until system is there is no bubble, continue that BTP saturations are added dropwise
The aqueous solution, control PH continues to react 1h in 2-3.Filtering, distills water washing, dries to obtain BTP intercalation modifying hydrotalcites (BTP-
LDH)。
Embodiment 6：
(1) 12.5g taurines are taken and 4g NaOH is dissolved in 250mL ethanol, after 25 DEG C of magnetic agitation reaction 30min,
10.6g benzaldehyde solutions are slowly added to, continue to react 10h, taurine-benzaldehyde schiff bases is dried to obtain in filtering, ethanol washing
(BT)。
(2) take 0.66g hypophosphorous acid and a small amount of trim,ethylchlorosilane is dissolved in 50mL methyl alcohol, 60 DEG C of magnetic agitations react 2h, then
2.35gBT is added, continues to react 15h.Filtering, ethanol washing, the compound (BTP) of dry product phosphorus-nitrogen containing sulphur.
(3) take 10g hydrotalcites to be added in the there-necked flask of the 250mL for filling 100mL distilled water, at 100 DEG C, machinery is stirred
2h is mixed, after uniform emulsion to be formed, adds the saturated aqueous solution of BTP until system is there is no bubble, continue that BTP saturations are added dropwise
The aqueous solution, control PH continues to react 2h in 2-3.Filtering, distills water washing, dries to obtain BTP intercalation modifying hydrotalcites (BTP-
LDH)。
Claims (11)
1. the preparation method of a kind of synthesis of phosphorous nitrogen sulfur compound and its intercalation modifying hydrotalcite, it is characterised in that：Synthesize
A kind of new structure compound (BTP) of phosphorus-nitrogen containing sulphur, and hydrotalcite layers are intercalation into by ion-exchange.
2. a kind of phosphorous nitrogen sulfur compound (BTP) synthetic method, it is characterised in that：Reaction monomers containing phosphorus, nitrogen, sulphur are carried out
Reaction intercalation compound of the generation with fire resistance, including following characteristics step：Setting reaction temperature under and reactant
In ratio range, in the presence of a catalyst, first nitrogenous sulphur monomer and aldehydes are reacted, then its product continues and phosphorous
Monomer reaction generates target compound.
3. the preparation method of BTP according to claim 2, it is characterised in that nitrogenous sulphur monomer (taurine, sulfamic acid,
P-aminobenzene sulfonic acid etc.) and aldehydes (benzaldehyde, salicylide, 3- tolyl aldehydes, parahydroxyben-zaldehyde, formaldehyde, acetaldehyde etc.)
The ratio of molal weight is 1:1, solvent is ethanol, and reaction temperature is 25~60 DEG C, and the reaction time is 3~8h, reaction generation nitrogen sulphur
Schiff bases (BT).
4. the preparation method of BTP according to claim 2, it is characterised in that BT and phosphorous-containing monomers (hypophosphorous acid, phosphorous acid two
Ethyl ester, dimethylphosphite, methyl hypophosphorous acid ethyl ester, methyl hypophosphorous acid methyl esters etc.) material molal weight ratio be 1:1, it is molten
Agent is methyl alcohol, and reaction temperature is 25~60 DEG C, and the reaction time is 10~15h.
5. the preparation method of BTP according to claim 2, it is characterised in that catalyst is trim,ethylchlorosilane, sodium hydride,
Alchlor, zinc chloride etc..
6. a kind of phosphorous nitrogen sulfur compound intercalation modifying hydrotalcite preparation method, its feature is comprised the following steps：First by neatly
Stone is added in deionized water, and dispersed slurries are made under mechanical agitation, is then added to the saturated aqueous solution of BTP above-mentioned
In slurries, by ion-exchange by BTP molecule intercalations to hydrotalcite layers.
7. phosphorous nitrogen sulfur compound intercalation modifying hydrotalcite preparation method according to claim 6, it is characterised in that used
Hydrotalcite be magnalium carbonate hydrotalcite, magnalium nitrate anion hydrotalcite, zinc-aluminium carbonate hydrotalcite, zinc-aluminium nitrate anion hydrotalcite,
Nickel aluminium carbonate hydrotalcite, nickel aluminium nitrate anion hydrotalcite etc..
8. phosphorous nitrogen sulfur compound intercalation modifying hydrotalcite preparation method according to claim 6, it is characterised in that neatly
Stone is 1 with the mass ratio of deionized water:2~1:20, at 80~100 DEG C, the reaction time is 1~6h to temperature control.
9. phosphorous nitrogen sulfur compound intercalation modifying hydrotalcite preparation method according to claim 6, it is characterised in that BTP is
Synthesize first.
10. phosphorous nitrogen sulfur compound intercalation modifying hydrotalcite preparation method according to claim 6, it is characterised in that BTP
The mass ratio of quality and hydrotalcite controlled 2~3 in 1~10, PH.
11. phosphorous nitrogen sulfur compound intercalation modifying hydrotalcite preparation methods according to claim 6, it is characterised in that BTP
It it is 80~100 DEG C with hydrotalcite reaction temperature, the reaction time is 1~6h, mechanical agitation.
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| CN108039503A (en) * | 2017-12-29 | 2018-05-15 | 成都新柯力化工科技有限公司 | Proton exchange membrane with hydrotalcite framework for fuel cell and preparation method thereof |
| CN110105298A (en) * | 2019-04-29 | 2019-08-09 | 湘潭大学 | A kind of synthesis of nitrogenous sulphur synergistic flame-retardant compound and its preparation method of intercalation modifying hydrotalcite |
| CN113461576A (en) * | 2021-06-23 | 2021-10-01 | 四川大学 | Dynamic covalent bond-based responsive surfactant and preparation method thereof |
| CN114854166A (en) * | 2022-05-20 | 2022-08-05 | 浙江昊杨新能源科技有限公司 | ABS modification method for power battery shell |
| CN114921050A (en) * | 2022-06-17 | 2022-08-19 | 山东亿科化学有限责任公司 | Modified ABS resin, preparation method thereof, modified ABS composite material and application thereof |
| CN115353669A (en) * | 2022-08-03 | 2022-11-18 | 湘潭大学 | Hydrotalcite-based flame retardant containing sulfur/nitrogen/phosphorus/transition metal and preparation method thereof |
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Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN108039503A (en) * | 2017-12-29 | 2018-05-15 | 成都新柯力化工科技有限公司 | Proton exchange membrane with hydrotalcite framework for fuel cell and preparation method thereof |
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| CN113461576A (en) * | 2021-06-23 | 2021-10-01 | 四川大学 | Dynamic covalent bond-based responsive surfactant and preparation method thereof |
| CN114854166A (en) * | 2022-05-20 | 2022-08-05 | 浙江昊杨新能源科技有限公司 | ABS modification method for power battery shell |
| CN114921050A (en) * | 2022-06-17 | 2022-08-19 | 山东亿科化学有限责任公司 | Modified ABS resin, preparation method thereof, modified ABS composite material and application thereof |
| CN114921050B (en) * | 2022-06-17 | 2023-06-16 | 山东亿科化学有限责任公司 | Modified ABS resin, preparation method thereof, modified ABS composite material and application thereof |
| CN115353669A (en) * | 2022-08-03 | 2022-11-18 | 湘潭大学 | Hydrotalcite-based flame retardant containing sulfur/nitrogen/phosphorus/transition metal and preparation method thereof |
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