CN114324320A - Efficient and recyclable pH test paper and preparation method thereof - Google Patents
Efficient and recyclable pH test paper and preparation method thereof Download PDFInfo
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- CN114324320A CN114324320A CN202111659732.8A CN202111659732A CN114324320A CN 114324320 A CN114324320 A CN 114324320A CN 202111659732 A CN202111659732 A CN 202111659732A CN 114324320 A CN114324320 A CN 114324320A
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- 238000012360 testing method Methods 0.000 title claims abstract description 49
- 238000002360 preparation method Methods 0.000 title claims abstract description 8
- -1 alkenyl pyridine Chemical compound 0.000 claims abstract description 19
- 238000000034 method Methods 0.000 claims abstract description 13
- 150000001875 compounds Chemical class 0.000 claims abstract description 12
- 239000011159 matrix material Substances 0.000 claims abstract description 12
- 238000001035 drying Methods 0.000 claims abstract description 11
- 239000000178 monomer Substances 0.000 claims abstract description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000003431 cross linking reagent Substances 0.000 claims abstract description 7
- 239000003999 initiator Substances 0.000 claims abstract description 7
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims abstract description 7
- 150000008053 sultones Chemical class 0.000 claims abstract description 7
- 238000010438 heat treatment Methods 0.000 claims abstract description 6
- 238000002156 mixing Methods 0.000 claims abstract description 6
- 238000002791 soaking Methods 0.000 claims abstract description 5
- 238000006243 chemical reaction Methods 0.000 claims description 19
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical group ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 12
- 239000002904 solvent Substances 0.000 claims description 12
- 238000005406 washing Methods 0.000 claims description 11
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 10
- ZIUHHBKFKCYYJD-UHFFFAOYSA-N n,n'-methylenebisacrylamide Chemical compound C=CC(=O)NCNC(=O)C=C ZIUHHBKFKCYYJD-UHFFFAOYSA-N 0.000 claims description 9
- 238000003756 stirring Methods 0.000 claims description 9
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 8
- 238000010526 radical polymerization reaction Methods 0.000 claims description 8
- 230000007935 neutral effect Effects 0.000 claims description 7
- KFDVPJUYSDEJTH-UHFFFAOYSA-N 4-ethenylpyridine Chemical compound C=CC1=CC=NC=C1 KFDVPJUYSDEJTH-UHFFFAOYSA-N 0.000 claims description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 6
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 claims description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 6
- 239000011837 N,N-methylenebisacrylamide Substances 0.000 claims description 6
- 239000003365 glass fiber Substances 0.000 claims description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 5
- GLVMTPQMPUWELB-UHFFFAOYSA-N n-pentylprop-2-enamide Chemical group CCCCCNC(=O)C=C GLVMTPQMPUWELB-UHFFFAOYSA-N 0.000 claims description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 5
- FSSPGSAQUIYDCN-UHFFFAOYSA-N 1,3-Propane sultone Chemical compound O=S1(=O)CCCO1 FSSPGSAQUIYDCN-UHFFFAOYSA-N 0.000 claims description 4
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 claims description 4
- UHQADSBKMJUJEK-UHFFFAOYSA-N 2-methylidenetetradecanamide Chemical compound CCCCCCCCCCCCC(=C)C(N)=O UHQADSBKMJUJEK-UHFFFAOYSA-N 0.000 claims description 4
- FFOLJFOMOFZLPG-UHFFFAOYSA-N 4-ethenyl-2-methylpyridine Chemical compound CC1=CC(C=C)=CC=N1 FFOLJFOMOFZLPG-UHFFFAOYSA-N 0.000 claims description 4
- OZJPLYNZGCXSJM-UHFFFAOYSA-N 5-valerolactone Chemical group O=C1CCCCO1 OZJPLYNZGCXSJM-UHFFFAOYSA-N 0.000 claims description 4
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 4
- 229920000877 Melamine resin Polymers 0.000 claims description 4
- 244000028419 Styrax benzoin Species 0.000 claims description 4
- 235000000126 Styrax benzoin Nutrition 0.000 claims description 4
- 235000008411 Sumatra benzointree Nutrition 0.000 claims description 4
- 229960002130 benzoin Drugs 0.000 claims description 4
- 235000019382 gum benzoic Nutrition 0.000 claims description 4
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 claims description 4
- 239000004745 nonwoven fabric Substances 0.000 claims description 4
- QRWVOJLTHSRPOA-UHFFFAOYSA-N 1,3-bis(prop-2-enyl)urea Chemical compound C=CCNC(=O)NCC=C QRWVOJLTHSRPOA-UHFFFAOYSA-N 0.000 claims description 3
- DZZAHLOABNWIFA-UHFFFAOYSA-N 2-butoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OCCCC)C(=O)C1=CC=CC=C1 DZZAHLOABNWIFA-UHFFFAOYSA-N 0.000 claims description 3
- KMNCBSZOIQAUFX-UHFFFAOYSA-N 2-ethoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OCC)C(=O)C1=CC=CC=C1 KMNCBSZOIQAUFX-UHFFFAOYSA-N 0.000 claims description 3
- ZKYCLDTVJCJYIB-UHFFFAOYSA-N 2-methylidenedecanamide Chemical compound CCCCCCCCC(=C)C(N)=O ZKYCLDTVJCJYIB-UHFFFAOYSA-N 0.000 claims description 3
- YIVJZNGAASQVEM-UHFFFAOYSA-N Lauroyl peroxide Chemical compound CCCCCCCCCCCC(=O)OOC(=O)CCCCCCCCCCC YIVJZNGAASQVEM-UHFFFAOYSA-N 0.000 claims description 3
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 claims description 3
- ZQMHJBXHRFJKOT-UHFFFAOYSA-N methyl 2-[(1-methoxy-2-methyl-1-oxopropan-2-yl)diazenyl]-2-methylpropanoate Chemical compound COC(=O)C(C)(C)N=NC(C)(C)C(=O)OC ZQMHJBXHRFJKOT-UHFFFAOYSA-N 0.000 claims description 3
- CNPHCSFIDKZQAK-UHFFFAOYSA-N n-prop-2-enylprop-2-enamide Chemical compound C=CCNC(=O)C=C CNPHCSFIDKZQAK-UHFFFAOYSA-N 0.000 claims description 3
- LNANXVFWEPDXDR-UHFFFAOYSA-N 2,4,6-tris(ethenyl)pyridine Chemical compound C=CC1=CC(C=C)=NC(C=C)=C1 LNANXVFWEPDXDR-UHFFFAOYSA-N 0.000 claims description 2
- DZPSSIZUIOHRNG-UHFFFAOYSA-N 2,4-bis(ethenyl)pyridine Chemical compound C=CC1=CC=NC(C=C)=C1 DZPSSIZUIOHRNG-UHFFFAOYSA-N 0.000 claims description 2
- IHAZIZDOOXZFAT-UHFFFAOYSA-N 2-methylideneundecanamide Chemical compound CCCCCCCCCC(=C)C(N)=O IHAZIZDOOXZFAT-UHFFFAOYSA-N 0.000 claims description 2
- SMTDFMMXJHYDDE-UHFFFAOYSA-N 2-prop-1-enylpyridine Chemical compound CC=CC1=CC=CC=N1 SMTDFMMXJHYDDE-UHFFFAOYSA-N 0.000 claims description 2
- IVSNOXIEOPUFRP-UHFFFAOYSA-N 3-hexylnon-2-enamide Chemical compound C(CCCCC)C(=CC(=O)N)CCCCCC IVSNOXIEOPUFRP-UHFFFAOYSA-N 0.000 claims description 2
- AKDJZAVMDJYMIT-UHFFFAOYSA-N 4-but-3-enylpyridine Chemical compound C=CCCC1=CC=NC=C1 AKDJZAVMDJYMIT-UHFFFAOYSA-N 0.000 claims description 2
- PWZRAFPNQSAEBD-UHFFFAOYSA-N 4-prop-1-enylpyridine Chemical compound CC=CC1=CC=NC=C1 PWZRAFPNQSAEBD-UHFFFAOYSA-N 0.000 claims description 2
- 238000001914 filtration Methods 0.000 claims description 2
- 239000000463 material Substances 0.000 claims description 2
- AWDYCSUWSUENQK-UHFFFAOYSA-N n-decylprop-2-enamide Chemical compound CCCCCCCCCCNC(=O)C=C AWDYCSUWSUENQK-UHFFFAOYSA-N 0.000 claims description 2
- ABUMECXPQVMMIN-UHFFFAOYSA-N n-heptylprop-2-enamide Chemical compound CCCCCCCNC(=O)C=C ABUMECXPQVMMIN-UHFFFAOYSA-N 0.000 claims description 2
- GCGQYJSQINRKQL-UHFFFAOYSA-N n-hexylprop-2-enamide Chemical compound CCCCCCNC(=O)C=C GCGQYJSQINRKQL-UHFFFAOYSA-N 0.000 claims description 2
- PZJKDAAVTRYGSW-UHFFFAOYSA-N n-undecylprop-2-enamide Chemical compound CCCCCCCCCCCNC(=O)C=C PZJKDAAVTRYGSW-UHFFFAOYSA-N 0.000 claims description 2
- MHYFEEDKONKGEB-UHFFFAOYSA-N oxathiane 2,2-dioxide Chemical compound O=S1(=O)CCCCO1 MHYFEEDKONKGEB-UHFFFAOYSA-N 0.000 claims description 2
- 238000007142 ring opening reaction Methods 0.000 claims description 2
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 claims description 2
- 239000007793 ph indicator Substances 0.000 claims 1
- 239000002243 precursor Substances 0.000 abstract description 6
- 238000001514 detection method Methods 0.000 abstract description 4
- 238000004064 recycling Methods 0.000 abstract description 3
- 125000004122 cyclic group Chemical group 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 46
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 16
- 239000013078 crystal Substances 0.000 description 16
- 238000000967 suction filtration Methods 0.000 description 16
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 8
- 239000000126 substance Substances 0.000 description 7
- 239000003086 colorant Substances 0.000 description 6
- 229910001873 dinitrogen Inorganic materials 0.000 description 6
- WTOPZJSTVMXTBW-UHFFFAOYSA-N CC(CCN1C=CC(C=C)=CC1)S(O)(=O)=O Chemical compound CC(CCN1C=CC(C=C)=CC1)S(O)(=O)=O WTOPZJSTVMXTBW-UHFFFAOYSA-N 0.000 description 5
- 230000008859 change Effects 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 239000003208 petroleum Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- YVBGKXAIYVEGSA-UHFFFAOYSA-N CC(CCN1C=CC(C=C)=CC1C=C)S(O)(=O)=O Chemical compound CC(CCN1C=CC(C=C)=CC1C=C)S(O)(=O)=O YVBGKXAIYVEGSA-UHFFFAOYSA-N 0.000 description 4
- CSPPXFDWQVTIFQ-UHFFFAOYSA-N CC1N(CCCS(O)(=O)=O)C=CC(C=C)=C1 Chemical compound CC1N(CCCS(O)(=O)=O)C=CC(C=C)=C1 CSPPXFDWQVTIFQ-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 229930188620 butyrolactone Natural products 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 230000002378 acidificating effect Effects 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-vinylpyridine Chemical compound C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-UHFFFAOYSA-N 0.000 description 2
- RSEACKZUWMDVMT-UHFFFAOYSA-N CCCC(CCN1C=CC=CC1C=C)S(O)(=O)=O Chemical compound CCCC(CCN1C=CC=CC1C=C)S(O)(=O)=O RSEACKZUWMDVMT-UHFFFAOYSA-N 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 125000001453 quaternary ammonium group Chemical group 0.000 description 2
- 238000010186 staining Methods 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- BKBJXABYOCBGED-UHFFFAOYSA-N 2-methylidenetridecanamide Chemical compound CCCCCCCCCCCC(=C)C(N)=O BKBJXABYOCBGED-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
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- 150000001924 cycloalkanes Chemical class 0.000 description 1
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- 238000005516 engineering process Methods 0.000 description 1
- AKRQHOWXVSDJEF-UHFFFAOYSA-N heptane-1-sulfonic acid Chemical compound CCCCCCCS(O)(=O)=O AKRQHOWXVSDJEF-UHFFFAOYSA-N 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
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- 150000002739 metals Chemical class 0.000 description 1
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- WLGDAKIJYPIYLR-UHFFFAOYSA-M octane-1-sulfonate Chemical compound CCCCCCCCS([O-])(=O)=O WLGDAKIJYPIYLR-UHFFFAOYSA-M 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- XWOTWKWOPAMHEQ-UHFFFAOYSA-N oxathiocane 2,2-dioxide Chemical compound O=S1(=O)CCCCCCO1 XWOTWKWOPAMHEQ-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000003209 petroleum derivative Substances 0.000 description 1
- 238000005504 petroleum refining Methods 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
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- 229960005486 vaccine Drugs 0.000 description 1
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Abstract
The invention discloses a preparation method of pH test paper with high efficiency and recycling, in particular to test paper capable of changing color in real time according to the pH value of an oil product. The method of the pH test paper comprises the following steps: mixing a zwitterionic compound synthesized by reacting alkenyl pyridine with sultone with an initiator, a cross-linking agent and an amphiphilic monomer to prepare a precursor solution, uniformly soaking the precursor solution and a matrix, and drying in a heating or ultraviolet irradiation mode to prepare the pH test paper. The test paper has the advantages of cyclic utilization and high detection efficiency, and can be applied to the field of detection of white oil and derivatives thereof.
Description
Technical Field
The invention relates to a preparation method of pH test paper with high efficiency and recycling, in particular to test paper capable of changing color in real time according to the pH value of an oil product.
Background
Petroleum is an important basic raw material for modern industry, and human life is also closely related to petroleum. With the rapid development of scientific technology and the rapid increase of the global population, the demand of people for petroleum is continuously increased. Petroleum is a complex mixture of alkanes, cycloalkanes, and aromatics, but petroleum is often contaminated during processing or transportation, thereby introducing organic acids or other impurities. Although the content of such impurities is small, the metals are corroded by the action of water and oxygen. Wherein the white oil is used as petroleum refining product and contains C as main ingredient16～C31The mixture of n-isoparaffin can be applied to the fields of vaccines, pesticides, plasticizers and the like. These fields all have higher requirements on white oil, and if the white oil contains some acidic or basic substances in the transportation, processing or storage processes, the white oil has greater influence on the market application of the white oil. Therefore, the pH change of the petroleum product caused by the introduction of impurities before and after processing and in the transportation process is strictly monitored, the product quality can be effectively improved, and the progress and the efficiency of industrial production are promoted.
The common pH test paper combines different micromolecule coloring agents on a test paper substrate, and realizes qualitative detection of liquid acidity and alkalinity based on the principle that the micromolecule coloring agents can show different colors under different acid-base environments. However, this kind of small molecule staining agent is only bound on the test paper matrix through simple physical action, and under the dripping of liquid, the staining agent is gradually carried away by the liquid, which results in the test paper having only "one-off" effect. In addition, after the liquid to be detected is dripped on the surface of the ordinary pH test paper, the color of the test paper is diluted due to the diffusion effect of the micromolecule coloring agent after a long time, and the test failure is caused because the color of the test paper cannot be accurately compared with a color comparison card. More importantly, since the white oil is a non-polar substance and the acid or alkali is difficult to ionize in the white oil, the white oil needs to be mixed with water before testing the acidity or alkalinity of the white oil, and the white oil does not necessarily ionize all hydrogen ions or hydroxyl ions after being mixed with the water due to the non-polar characteristic of the white oil. The surface of the ordinary pH test paper is completely provided with a polar micromolecular coloring agent, so that the ordinary pH test paper has a repulsive effect on white oil and cannot be combined with all ionized ions. After the two negative effects are superposed, the common pH test paper is difficult to be effectively applied to the acid-base test of the white oil and the derivatives. At present, a pH tester is often selected as a method for measuring water-soluble acid or alkali of white oil and derivatives thereof, and although the pH tester can quickly test the acidity or alkalinity of an oil product, the pH tester cannot be carried and can only be used in a fixed place, and the pH tester has great limitation in practical use. Therefore, it is very important to develop a portable, recyclable and accurate pH test paper.
Disclosure of Invention
The invention aims to provide a preparation method of pH test paper which is efficient and recyclable.
In order to realize the purpose, the following technical scheme is provided:
the preparation method of the efficient and recyclable pH test paper comprises the following steps:
1) preparation of chromogenic zwitterionic compound. Specifically, alkenyl pyridine and sultone can be added into a reactor and stirred at a high speed at 50-120 ℃ for reaction for 1-30 h. After the reaction is finished, the pure zwitterion compound is obtained by filtering, washing and vacuum drying. The color development mechanism of the compound is as follows: when the chromogenic substance is combined with hydrogen ions or hydroxide ions, the chromogenic substance undergoes the transition of a molecular type and an ionic type conjugated system, which causes the change of the absorption spectrum, thereby realizing different color development. In detail, for example, hydroxide in the solution can attack quaternary ammonium groups on a pyridine ring, and the combination of the hydroxide and the quaternary ammonium groups changes the conjugated structure of the substance, so that the absorbance changes along with the change of the conjugated structure, and the color is developed; similarly, under the acidic condition, the color of the liquid changes after hydrogen ions attack the sulfonate. In addition, in different pH media, the concentration ratio of the molecular type and the ionic type of the chromogenic substance is different, and in this case, the system displays the color of the dominant concentration indicator.
2) And mixing the color-developing zwitterionic compound with an initiator, a cross-linking agent and an amphiphilic monomer, and dissolving the mixture in a solvent to form a prepolymer solution. The amphiphilic monomer is added, so that the hydrophilicity and lipophilicity of the pH test paper can be effectively improved, and the test paper is promoted to rapidly and efficiently absorb hydrogen ions or hydroxyl ions ionized from the oil-water mixed solution.
3) And after the matrix material is soaked in the prepolymer solution, carrying out free radical polymerization reaction by heating or ultraviolet irradiation. Specifically, the method comprises the following steps: 3.1) fully soaking the precursor solution in the matrix material for 1-24 h, and then heating the matrix material by hot air at 50-100 ℃ to ensure that the matrix material is fixed on the matrix material in a cross-linking manner. And then putting the mixture into a vacuum oven for drying, and drying for 1-6 h at 40-70 ℃.
Or 3.2) fully soaking the precursor solution in the matrix material for 1-24 h, and then reacting for 20-60 min under a UV lamp with the wavelength of 365nm to ensure that the precursor solution is fixed on the matrix material in a cross-linking manner. And then putting the mixture into a vacuum oven for drying, and drying for 1-6 h at 40-70 ℃.
In the above scheme, preferably, the alkenyl pyridine is selected from 4-butenyl pyridine, 4-propenyl pyridine, 4-vinyl pyridine, 2-propenyl pyridine, 2, 4-divinyl pyridine, 2,4, 6-trivinyl pyridine, 2-methyl-4-vinyl pyridine, but is not limited thereto.
Preferably, the sultone is selected from the group consisting of valerolactone, butanesultone, propanesultone, hexansultone, heptanesulfonate and octanesulfonate, but is not limited thereto.
Preferably, the initiator is selected from the group consisting of azobisisoheptonitrile, azobisisobutyronitrile, dimethyl azobisisobutyrate, lauroyl peroxide, di-t-butyl peroxide, hydrogen peroxide, benzoin ethyl ether, benzoin butyl ether, benzoin dimethyl ether, but is not limited thereto.
Preferably, the crosslinking agent is selected from the group consisting of N, N-methylenebisacrylamide, N-vinylbisacrylamide, 1, 3-diallylurea, bisacrylamide, and N-allylacrylamide, but is not limited thereto.
Preferably, the amphiphilic monomer is selected from the group consisting of amyl acrylamide, hexyl acrylamide, heptyl acrylamide, octyl acrylamide, nonyl acrylamide, decyl acrylamide, undecyl acrylamide, dodecyl acrylamide, dihexyl acrylamide, but is not limited thereto.
Preferably, the solvent is selected from the group consisting of dichloromethane, chloroform, dimethylsulfoxide, N-dimethylformamide, tetrahydrofuran, but is not limited thereto.
Preferably, the base material is selected from the group consisting of fast neutral glass fiber filter paper having ash property of less than 0.1, cotton nonwoven fabric, and melamine open-cell sponge, but is not limited thereto.
Preferably, the chromogenic zwitterionic compound, the initiator, the cross-linking agent and the amphiphilic monomer are respectively as follows in parts by weight: 100 parts, 0.5-1.5 parts, 0.5-2.5 parts and no more than 30 parts, wherein if the dosage of the amphiphilic monomer is more than 30 parts, the hydrophile lipophile of the prepared pH test paper is greatly reduced.
Compared with the prior art, the invention has the beneficial effects that:
firstly, the pH test paper can be prepared by two easily-obtained modes of heating or ultraviolet irradiation; secondly, the pH test paper can realize rapid color change in different acid-base environments, has a high-efficiency color development effect, does not lose efficacy with the time, can be recycled, and can be reused by only washing with water to be neutral and drying after being used in an acid environment, and cannot be inactivated even if being taken to be an alkaline environment rapidly under an acid condition; thirdly, the pH test paper can be prepared into any size according to requirements, is easy to carry, and has great freedom degree in use scenes.
Drawings
FIG. 1 shows the nuclear magnetic hydrogen spectrum of the zwitterionic compound prepared in example 1.
FIG. 2 is a graph showing the color change of the test paper at different pH values in example 1.
FIG. 3 shows the recycling performance of the test strips of example 1 at different pH values.
FIG. 4 is a schematic diagram showing the synthesis route of 4-vinyl-1- (3-sulfobutyl) pyridine in example 1.
Detailed Description
The principle of the invention is that firstly, alkenyl pyridine and sultone are subjected to ring-opening reaction to prepare the chromogenic zwitterionic compound. Then the compound is fully mixed with an initiator, a cross-linking agent and an amphiphilic monomer to form a prepolymer. And then fully soaking the precursor and a matrix material, and carrying out free radical polymerization reaction by heating or ultraviolet irradiation. Finally, the pH test paper which can display different colors under acidic or alkaline conditions and can be reused is prepared.
The present invention will be further described with reference to the following examples.
Example 1:
4-vinylpyridine (10.51g, 0.1mol) and butyrolactone (17.70g, 0.13mol) and dry toluene were sequentially added to a 250ml three-necked flask, stirred until well mixed, and nitrogen gas was introduced while stirring. The reaction system is reacted for 24 hours at the temperature of 100 ℃. After the reaction is finished, white crystals of 4-vinyl-1- (3-sulfobutyl) pyridine are separated out from the solution. And then, carrying out suction filtration on the solution, continuously washing the solution with butanone for multiple times while carrying out suction filtration, and collecting white crystals.
4-vinyl-1- (3-sulfobutyl) pyridine (1.22g, 0.005mol) was poured into methylene chloride to prepare a 1mol/L solution. Next, amyl acrylamide (0.71g, 0.005mol), benzoin (0.0122g) and N, N-methylenebisacrylamide (0.15g) were added in this order, mixed well, and the solution was dropped uniformly onto a neutral glass fiber filter paper and reacted under a 365nm ultraviolet lamp for 40 min. After drying to remove the solvent, a pH test paper was prepared. The nuclear magnetic detection data of the color-developing substance obtained in the meantime are shown in FIG. 3.
Example 2:
2, 4-vinylpyridine (13.11g, 0.1mol) and butyrolactone (34.04g, 0.13mol) and dry toluene were added in this order to a 250ml three-necked flask, stirred until well mixed, and nitrogen was introduced with stirring. The reaction system is reacted for 30 hours at the temperature of 115 ℃. After the reaction is finished, white 2, 4-divinyl-1- (3-sulfobutyl) pyridine crystals are separated out from the solution. And then, carrying out suction filtration on the solution, continuously washing the solution with butanone for multiple times while carrying out suction filtration, and collecting white crystals.
2, 4-divinyl-1- (3-sulfobutyl) pyridine (1.34g, 0.005mol) was poured into dichloromethane to prepare a 1mol/L solution. Next, amyl acrylamide (0.71g, 0.005mol), benzoin butyl ether (0.0134g), and N, N-methylene bisacrylamide (0.15g) were added in this order, mixed well, and the solution was dropped uniformly onto a neutral glass fiber filter paper and reacted for 30min under a 365nm ultraviolet lamp. After drying to remove the solvent, a pH test paper was prepared.
Example 3:
2-vinylpyridine (10.51g, 0.1mol) and caprolactone (21.35g, 0.13mol) and dry toluene were sequentially added to a 250ml three-necked flask, and stirred until sufficiently mixed, and nitrogen gas was introduced while stirring. The reaction system is reacted for 20 hours at the temperature of 75 ℃. After the reaction is finished, white 2-vinyl-1- (3-sulfohexyl) pyridine crystals are precipitated in the solution. And then, carrying out suction filtration on the solution, continuously washing the solution with butanone for multiple times while carrying out suction filtration, and collecting white crystals.
2-vinyl-1- (3-sulfohexyl) pyridine (1.35g, 0.005mol) was poured into chloroform to prepare a 5mol/L solution. Then, dodecyl acrylamide (0.71g, 0.005mol), benzoin dimethyl ether (0.0135g) and N, N-methylene bisacrylamide (0.15g) were added in this order, and after thorough mixing, the solution was dropped uniformly onto a cotton nonwoven fabric, and reacted for 40min under a 365nm ultraviolet lamp. After drying to remove the solvent, a pH test paper was prepared.
Example 4:
2-methyl-4-vinylpyridine (11.92g, 0.1mol) and propane sultone (15.87g, 0.13mol) and dry toluene were sequentially added to a 250ml three-necked flask, stirred until well mixed, and nitrogen gas was introduced while stirring. The reaction system is reacted for 24 hours at the temperature of 90 ℃. After the reaction is finished, white 2-methyl-4-vinyl-1- (3-sulfopropyl) pyridine crystals are separated out from the solution. And then, carrying out suction filtration on the solution, continuously washing the solution with butanone for multiple times while carrying out suction filtration, and collecting white crystals.
2-methyl-4-vinyl-1- (3-sulfopropyl) pyridine (1.22g, 0.005mol) was poured into tetrahydrofuran to prepare a 3mol/L solution. Next, octyl acrylamide (0.71g, 0.005mol), benzoin ethyl ether (0.0122g), and N, N-vinyl bisacrylamide (0.15g) were added in this order, mixed well, and the solution was dropped uniformly onto a neutral glass fiber filter paper and reacted under a 365nm ultraviolet lamp for 25 min. After drying to remove the solvent, a pH test paper was prepared.
Example 5:
2-vinylpyridine (10.51g, 0.1mol) and octanesulfonic acid lactone (24.96g, 0.13mol) and dry toluene were sequentially added to a 250ml three-necked flask, and stirred until sufficiently mixed, and nitrogen gas was introduced while stirring. The reaction system is reacted for 24 hours at the temperature of 100 ℃. After the reaction is finished, white 2-vinyl-1- (3-sulfooctyl) pyridine crystals are separated out from the solution. And then, carrying out suction filtration on the solution, continuously washing the solution with butanone for multiple times while carrying out suction filtration, and collecting white crystals.
2-vinyl-1- (3-sulfooctyl) pyridine (1.36g, 0.005mol) was poured into dimethyl sulfoxide to prepare a 1mol/L solution. Then, amyl acrylamide (0.71g, 0.005mol), azobisisoheptonitrile (0.0136g) and N-allyl acrylamide (0.15g) were added in this order, and after thorough mixing, the solution was dropped uniformly onto cotton-spun nonwoven fabric, and then placed in an oven at 100 ℃ to heat and accelerate radical polymerization, while removing the solvent, and finally the pH test paper was prepared.
Example 6:
2, 4-vinylpyridine (13.11g, 0.1mol) and butyrolactone (34.04g, 0.13mol) and dry toluene were added in this order to a 250ml three-necked flask, stirred until well mixed, and nitrogen was introduced with stirring. The reaction system is reacted for 30 hours at the temperature of 115 ℃. After the reaction is finished, white 2, 4-divinyl-1- (3-sulfobutyl) pyridine crystals are separated out from the solution. And then, carrying out suction filtration on the solution, continuously washing the solution with butanone for multiple times while carrying out suction filtration, and collecting white crystals.
2, 4-divinyl-1- (3-sulfobutyl) pyridine (1.34g, 0.005mol) was poured into N, N-dimethylformamide to prepare a 1mol/L solution. Then, dodecylacrylamide (0.60g, 0.0025mol), dimethyl azobisisobutyrate (0.0134g), and bisacrylamide (0.18g) were added in this order, mixed thoroughly, and the solution was dropped uniformly onto a melamine open-cell sponge, and placed in an oven at 100 ℃ to heat and accelerate radical polymerization, while removing the solvent, to finally prepare a pH test paper.
Example 7:
2-methyl-4-vinylpyridine (11.92g, 0.1mol) and propane sultone (15.87g, 0.13mol) and dry toluene were sequentially added to a 250ml three-necked flask, stirred until well mixed, and nitrogen gas was introduced while stirring. The reaction system is reacted for 24 hours at the temperature of 90 ℃. After the reaction is finished, white 2-methyl-4-vinyl-1- (3-sulfopropyl) pyridine crystals are separated out from the solution. And then, carrying out suction filtration on the solution, continuously washing the solution with butanone for multiple times while carrying out suction filtration, and collecting white crystals.
2-methyl-4-vinyl-1- (3-sulfopropyl) pyridine (1.22g, 0.005mol) was poured into tetrahydrofuran to prepare a 3mol/L solution. Then, 1, 3-diallyl urea (0.35g, 0.0025mol), di-tert-butyl peroxide (0.0122g) and N, N-vinyl bisacrylamide (0.21g) are added in sequence, the mixture is fully mixed, then the solution is uniformly dripped on a melamine open-pore sponge, the mixture is placed in an oven and heated at 60 ℃ to promote the free radical polymerization reaction, meanwhile, the solvent is removed, and finally the pH test paper is prepared.
Example 8:
4-vinylpyridine (10.51g, 0.1mol) and butyrolactone (17.70g, 0.13mol) and dry toluene were sequentially added to a 250ml three-necked flask, stirred until well mixed, and nitrogen gas was introduced while stirring. The reaction system is reacted for 24 hours at the temperature of 100 ℃. After the reaction is finished, white crystals of 4-vinyl-1- (3-sulfobutyl) pyridine are separated out from the solution. And then, carrying out suction filtration on the solution, continuously washing the solution with butanone for multiple times while carrying out suction filtration, and collecting white crystals.
4-vinyl-1- (3-sulfobutyl) pyridine (1.22g, 0.005mol) was poured into tetrahydrofuran to prepare a 2mol/L solution. Then, undecylacrylamide (0.79g, 0.0035mol), lauroyl peroxide (0.0122g) and N, N-methylenebisacrylamide (0.15g) were added in this order, and after thorough mixing, the solution was uniformly dropped on a neutral glass fiber filter paper, and the filter paper was put into an oven at 100 ℃ to heat and accelerate radical polymerization, and the solvent was removed at the same time, thereby finally obtaining a pH test paper.
Claims (10)
1. A preparation method of high-efficiency and recyclable pH test paper is characterized in that,
firstly, carrying out ring-opening reaction on alkenyl pyridine and sultone to prepare a chromogenic zwitterionic compound;
fully mixing the color-developing zwitterionic compound, the initiator, the cross-linking agent and the amphiphilic monomer in a solvent to form a prepolymer solution;
and then fully soaking the matrix material in the prepolymer solution, and carrying out free radical polymerization reaction to obtain the pH test paper.
2. The method for preparing the highly efficient and recyclable pH test paper according to claim 1, characterized in that alkenyl pyridine and sultone are added into a reactor, the mixture is reacted for 1-30 hours at 50-120 ℃ under stirring, and after the reaction is finished, the color-developing zwitterionic compound is obtained by filtering, washing and drying.
3. The method for preparing a highly efficient and recyclable pH indicator paper as claimed in claim 1, wherein the alkenyl pyridine is selected from the group consisting of 4-butenyl pyridine, 4-propenyl pyridine, 4-vinyl pyridine, 2-propenyl pyridine, 2, 4-divinyl pyridine, 2,4, 6-trivinyl pyridine and 2-methyl-4-vinyl pyridine; the sultone is selected from valerolactone, butanesultone, propanesultone, caprolactone, heptasultone or octanessultone.
4. The method for preparing the efficient and recyclable pH test paper according to claim 1, wherein the initiator is selected from the group consisting of azobisisoheptonitrile, azobisisobutyronitrile, dimethyl azobisisobutyrate, lauroyl peroxide, di-t-butyl peroxide, hydrogen peroxide, benzoin ethyl ether, benzoin butyl ether, and benzoin dimethyl ether.
5. The method according to claim 1, wherein the cross-linking agent is selected from the group consisting of N, N-methylenebisacrylamide, N-vinylbisacrylamide, 1, 3-diallylurea, bisacrylamide, and N-allylacrylamide.
6. The method according to claim 1, wherein the amphiphilic monomer is selected from the group consisting of amyl acrylamide, hexyl acrylamide, heptyl acrylamide, octyl acrylamide, nonyl acrylamide, decyl acrylamide, undecyl acrylamide, dodecyl acrylamide, and dihexyl acrylamide.
7. The method according to claim 1, wherein the solvent is selected from dichloromethane, chloroform, dimethylsulfoxide, N-dimethylformamide, and tetrahydrofuran.
8. The method for preparing the efficient and recyclable pH test paper according to claim 1, wherein the base material is selected from the group consisting of fast neutral glass fiber filter paper with ash property less than 0.1, cotton-spun non-woven fabric, and melamine open-cell sponge.
9. The method for preparing the highly efficient and recyclable pH test paper according to claim 1, wherein the matrix material is soaked in the prepolymer solution and then subjected to radical polymerization by means of heating or ultraviolet irradiation.
10. The pH strip according to any one of claims 1 to 9, wherein the pH strip is directly used for detecting the pH value of the white oil and the derivatives thereof.
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Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3754055A (en) * | 1970-12-28 | 1973-08-21 | California Inst Of Techn | Cationic vinyl-pyridine copolymers and products thereof |
| US4376162A (en) * | 1980-10-17 | 1983-03-08 | Fuji Photo Film Co., Ltd. | Heat-developable photosensitive material with antihalation layer |
| US5523367A (en) * | 1992-05-20 | 1996-06-04 | Phillips Petroleum Company | Superabsorbent polymers from ampholytic monomers |
| US20050282925A1 (en) * | 2004-02-23 | 2005-12-22 | Florida State University Research Foundation Inc. | Thin films for controlled protein interaction |
| CN1890563A (en) * | 2003-11-22 | 2007-01-03 | Agt科学有限公司 | Polymeric materials for assessing pH |
| US20070196492A1 (en) * | 2004-03-19 | 2007-08-23 | Sony Corporation | Stimuli-Responesive Hydrogel,Production Method Of Stimuli-Responsive Hydrogel,And Polymer Actuator Using Stimuli-Responsive Hydrogel |
| US20200277450A1 (en) * | 2017-11-02 | 2020-09-03 | Technion Research & Development Foundation Limited | Hipe-templated zwitterionic hydrogels, process of preparation and uses thereof |
| CN112679666A (en) * | 2020-11-11 | 2021-04-20 | 北京化工大学 | Method capable of quickly and efficiently separating stimulus-responsive star-shaped and linear polymers |
-
2021
- 2021-12-30 CN CN202111659732.8A patent/CN114324320A/en active Pending
Patent Citations (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3754055A (en) * | 1970-12-28 | 1973-08-21 | California Inst Of Techn | Cationic vinyl-pyridine copolymers and products thereof |
| US4069365A (en) * | 1970-12-28 | 1978-01-17 | California Institute Of Technology | Cationic vinyl pyridine copolymers and products thereof |
| US4376162A (en) * | 1980-10-17 | 1983-03-08 | Fuji Photo Film Co., Ltd. | Heat-developable photosensitive material with antihalation layer |
| US5523367A (en) * | 1992-05-20 | 1996-06-04 | Phillips Petroleum Company | Superabsorbent polymers from ampholytic monomers |
| CN1890563A (en) * | 2003-11-22 | 2007-01-03 | Agt科学有限公司 | Polymeric materials for assessing pH |
| US20050282925A1 (en) * | 2004-02-23 | 2005-12-22 | Florida State University Research Foundation Inc. | Thin films for controlled protein interaction |
| US20070196492A1 (en) * | 2004-03-19 | 2007-08-23 | Sony Corporation | Stimuli-Responesive Hydrogel,Production Method Of Stimuli-Responsive Hydrogel,And Polymer Actuator Using Stimuli-Responsive Hydrogel |
| US20200277450A1 (en) * | 2017-11-02 | 2020-09-03 | Technion Research & Development Foundation Limited | Hipe-templated zwitterionic hydrogels, process of preparation and uses thereof |
| CN112679666A (en) * | 2020-11-11 | 2021-04-20 | 北京化工大学 | Method capable of quickly and efficiently separating stimulus-responsive star-shaped and linear polymers |
Non-Patent Citations (2)
| Title |
|---|
| BIJAY P. TRIPATHI ET AL.: "Antifouling and antibiofouling pH responsive block copolymer based membranes by selective surface modification", 《JOURNAL OF MATERIALS CHEMISTRY B》, no. 01, 31 December 2013 (2013-12-31), pages 3397 * |
| 北京化工厂: "正在变革中的pH试纸", 《化学通报》, no. 6, 31 December 1977 (1977-12-31), pages 45 - 46 * |
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