CN1709171A - Use of phthalocyanin compound as cigarette harm-reducing agent - Google Patents
Use of phthalocyanin compound as cigarette harm-reducing agent Download PDFInfo
- Publication number
- CN1709171A CN1709171A CN200510040907.1A CN200510040907A CN1709171A CN 1709171 A CN1709171 A CN 1709171A CN 200510040907 A CN200510040907 A CN 200510040907A CN 1709171 A CN1709171 A CN 1709171A
- Authority
- CN
- China
- Prior art keywords
- phthalocyanine
- reducing agent
- cigarette
- harm
- compound
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
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- 235000019504 cigarettes Nutrition 0.000 title claims abstract description 101
- 239000003638 chemical reducing agent Substances 0.000 title claims abstract description 98
- -1 phthalocyanin compound Chemical class 0.000 title claims abstract description 17
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- 150000002602 lanthanoids Chemical class 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 239000002932 luster Substances 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 229910052752 metalloid Inorganic materials 0.000 description 1
- 150000002738 metalloids Chemical class 0.000 description 1
- 229920003240 metallophthalocyanine polymer Polymers 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 231100000350 mutagenesis Toxicity 0.000 description 1
- 238000002703 mutagenesis Methods 0.000 description 1
- 231100000299 mutagenicity Toxicity 0.000 description 1
- 230000007886 mutagenicity Effects 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 238000003199 nucleic acid amplification method Methods 0.000 description 1
- 230000000474 nursing effect Effects 0.000 description 1
- 230000005693 optoelectronics Effects 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000005022 packaging material Substances 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 231100000915 pathological change Toxicity 0.000 description 1
- 230000036285 pathological change Effects 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 230000001699 photocatalysis Effects 0.000 description 1
- 238000007146 photocatalysis Methods 0.000 description 1
- 238000002428 photodynamic therapy Methods 0.000 description 1
- VVOPUZNLRVJDJQ-UHFFFAOYSA-N phthalocyanine copper Chemical class [Cu].C12=CC=CC=C2C(N=C2NC(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2N1 VVOPUZNLRVJDJQ-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 125000005575 polycyclic aromatic hydrocarbon group Chemical group 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 108020003175 receptors Proteins 0.000 description 1
- 230000027756 respiratory electron transport chain Effects 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 230000011218 segmentation Effects 0.000 description 1
- 238000001338 self-assembly Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 235000019154 vitamin C Nutrition 0.000 description 1
- 239000011718 vitamin C Substances 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
Landscapes
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
The present invention relates to an application of phthalocyanin compound as harm-reducing agent of cigarette. Said phthalocyanin compound can obviously reduce harmful substances of CO, nitrogen oxide, aldehydes and amines in the smoke, and also can remove noble metal ions and eliminate free radical.
Description
Technical field
The present invention relates to the new purposes of phthalocyanine-like compound, specifically relate to the application of phthalocyanine-like compound as cigarette harm-reducing agent.
Background technology
Harmful components in the cigarette smoke mainly contain carbon monoxide, nitrogen oxide, volatile aldehyde material, amine, volatile nitrosamine, vinyl chloride, gaseous phase free radical etc.The harmful substance of flue gas grain in mutually mainly contains nitrosamine, BaP and other condensed-nuclei aromatics, aldehydes matter, nicotine and derivative thereof, grain phase free radical, polycyclic aromatic hydrocarbon etc.The harmful substance of flue gas grain in mutually mainly is present in the tar, and wherein 0.6% composition is thought harmful components, and wherein 0.2% is carcinogenic and possible carcinogenic composition, and 0.4% is auxiliary carcinogenic composition.Flue gas also has acid beastly, and pungent mouthfeel is that low-grade aldehydes has the advantages that molecular weight is little, boiling point is low, volatility is high (as 19 ℃ of formaldehyde boiling points because the low-grade aldehydes in the flue gas causes; 20.2 ℃ of acetaldehyde boiling points; 52.5 ℃ of methacrylaldehyde boiling points), these aldehydes are limited by cellulose acetate filter absorption, also are difficult to by the absorption of the polypropylene fiber filter tip of low polarity.Even the part physical absorption has taken place, also can desorb take place along with the rising of filter tip temperature in the later stage of smoking.
The harm order benefit of free radical is familiar with by everybody in the flue gas, free radical is defined as containing at least atom or the atomic group by a unpaired electronics in chemistry, studies show that in recent years, free radical is to endanger one of the most serious product in the cigarette, unsettled free radical can the attack cells composition, cause PD, lipid oxidation and make damaged membrane, the DNA depolymerization, thereby cause cancer, angiocardiopathy, thrombosis and artery sclerosis etc., thereby the free radical of removing cost-effectively in the flue gas is very necessary.
What Chinese scholars had utilizes materials such as Tea Polyphenols through active carbon adsorption, make composite filter tip and remove free radical, or medicinal herb components is added on removes free radical in the pipe tobacco, as Chinese patent (application number: 95116865.7) use bluish dogbane to make an addition in the pipe tobacco and can reduce cigarette free radical 11.5%, Tea Polyphenols mixed with the vitamin C equal proportion to make an addition to make composite filter tip in the active carbon and can reduce cigarette free radical 23.5%, but efficient has much room for improvement.
The basic framework of phthalocyanine-like compound is four macrocyclic structures that the iso-indoles unit is become by the N bridging, has diameter to be about 2.7 * 10 in the ring
-10The hole of m can hold many transition metal and metallic elements such as iron, copper, brill, aluminium, nickel, calcium, sodium, magnesium, zinc.Its structure is a plane molecule, and metallic atom is positioned at symmetrical centre.The phthalocyanine ring itself is a big π system with 18 pi-electrons. distribution of electron density is quite even on it.
Phthalocyanine combines with metallic element can generate metal complex, and metallic atom has replaced two hydrogen atoms that are positioned at this planar molecule center.Owing to generate co-ordination complex with metallic element, so in the metallophthalocyanine molecule, have only 16 pi-electrons.Because the conjugation of molecule, the covalent bond and the coordinate bond that link to each other with metallic atom are equal in itself.16 hydrogen atoms on four phenyl ring of phthalocyanine periphery, they can be replaced by many atoms or group.The result who replaces has derived various phthalocyanine derivates.Most of phthalocyanine complex dissolubilities are relatively poor, and the phthalocyanine complex and the sulfonated phthalocyanine complex of the synthetic alkoxyl replacement of people make it in organic solvent and water fine solubility be arranged respectively usually.
In the research in early days, phthalocyanine or metal phthalocyanine mainly are used as pigment or dyestuff, and phthalocyanine color has lovely luster, tinting strength, tinting power height, have high temperature resistant and premium properties sun-proof, and particle is thin, very easily diffusion and processing grinding.Be mainly used in the painted of printing ink, tin printing ink, coating, drawing watercolor, greasepaint pigment and pigment printing and rubber, plastic products.Along with development of modern science and technology, the application of phthalocyanine compound is expanded greatly.
Phthalocyanine has some special natures, as: near infrared absorption, photochromic, opto-electronic conversion, electrochromism, the light () property led and nonlinear optical property or the like.Phthalocyanine has unique heat endurance and chemical stability with it, have peculiar light, electricity, redox, photophysical property and receive countries in the world researcher's concern, at present, the application of phthalocyanine compound has related to the little sensitive device of chemical sensor, electroluminescent device, solar cell material, optical disc information recording materials, electrofax material, liquid crystal display material, nonlinear optical material, fuel electricity electrocatalysis material, synthetic metal and conducting polymer among him or the like.In addition, phthaleins such as aluminium, magnesium, zinc, gallium works complex has stronger photocatalysis, photoactivate, redox ability and fluorescent characteristic, has been subjected to people's great attention as the detection of cancer cell in the organism and the research that suppresses the active material of growth of cancer cells.Aspect the photodynamic therapy of cancer. phthalocyanine is being brought into play very important effect.In chemical industry, also can be used for industry and remove mercaptan and other sulfide.
Advantages such as that phthalocyanine-like compound has is inexpensive, Heat stability is good, low toxicity are one of important function materials.Just be allowed to be used as the food color .1985 U.S. again by legislation as far back as copper phthalocyanine in 1954 in Germany, with copper phthalein green grass or young crops as water medical colouring agent of a specified duration.It can be used for the painted of polypropylene operation suture thread (especially ophthalmologic operation).The pigment phthalocyanine blue is being used as plastic colorant always, and these coloured plastics materials are adopted by all trades and professions, and is used as the packaging material of food.Generally speaking, the kind that brominated amount is high more, its tone is just yellow more.Because natural green all is that green middle band is yellow, so the color of yellowish phthalocyanine green is more approaching green naturally, so also just more liked by the people.All come in many high-grade occasions with it painted, for example: superior cosmetics packing box painted, high-grade drink bottle (jar), painted as: the Packaging Bottle (jar) of beverages such as Sprite, Seven Up, Jilibao, Lay illiteracy.
Acute toxinology experiment shows, the LD50＞1000mg/kg of copper phthalocyanine in the rabbit body is than low 4 times of cupric oxide, than low 70 times of copper chloride.Nursing to mouse studies show that, its LD50＞5000mg/kg, and also to skin, the irritant test of eyes shows the negativity result.Through the subchronic test in 13 weeks, do not show any toxicity or pathological change takes place.For the Salmonella reversion test of mutagenicity, the result also is negativity.Mouse is carried out the injection testing of phthalocyanine blue, in 8 months process, do not find mutagenesis trend.
The phthalocyanine that has solubility in water is very low, and test shows for aquatic organism (as fish) and do not have toxicity, can not can be removed from waste water mechanically by bio-absorbable.In addition, complexing or covalently bound copper in the copper phthalocyanine molecule also can not be utilized by biological, so its toxicity are more much lower than water-soluble copper compound.
At present, phthalocyanine-like compound still of no use is as the report of cigarette harm-reducing agent.
Summary of the invention
The new purposes that the purpose of this invention is to provide a kind of phthalocyanine-like compound, promptly phthalocyanine-like compound is as the application of cigarette harm-reducing agent or flue gas harm-reducing agent.
Technical scheme of the present invention is: phthalocyanine-like compound is as the application of cigarette harm-reducing agent.
Said phthalocyanine-like compound is that structure is phthalocyanine or derivatives thereof or the independent or compound formation of phthalocyanin of formula I,
Formula I
M wherein is the metallic atom of hydrogen or Pd, Co, Ni, Cu, Zn, Mn, Fe, Mn, Cr, Sn, Pt, and the substituting group on the C1-C16 is hydrogen, alkyl, alkoxyl, alcoxyl hydroxyl, halogen, sulfo group, amido or amino etc.
Further, the preferred phthalocyanine of the present invention, iron-phthalocyanine, zinc phthalocyanine, cobalt phthalocyanine, copper phthalocyanine, magnesium phthalocyanine, zinc phthalocyanine, phthalocyanin and derivative thereof, poly-phthalocyanine, binuclear phthalocyanine are as harm-reducing agent.Element with phthalocyanine effect formation complex of the present invention is included in " the phthalocyanine periodic table " of table 1, formula 2 to the compound of formula 7 is wherein several examples, as the poly-phthalocyanine siloxanes of four-4-(2,4-ditert-amyl phenoxy base), tetramino zinc phthalocyanine (ZnTNPc) etc.
Table 1. phthalocyanine periodic table
| ??1a | ??2a | ??3b | ??4b | ??5b | ??6b | ??7b | ??8 | ??1b | ??2b | ??3a | ??4a | ??5a | ??6a | ??7a | ?0 | ||
| ??H | |||||||||||||||||
| ??Li | ??Be | ||||||||||||||||
| ??Na | ??Mg | ??Al | ??Si | ??P | |||||||||||||
| ??K | ??Ca | ??Sc | ??Ti | ??V | ??Cr | ??Mn | ??Fe | ??Co | ??Ni | ??Cu | ??Zn | ??Ga | ??Ge | ??As | |||
| ??Y | ??Zr | ??Nb | ??Mo | ??Tc | ??Ru | ??Rh | ??Pb | ??Ag | ??Cd | ??In | ??Sn | ??Sb | |||||
| ??Ba | ??La | ??Hf | ??Ta | ??W | ??Re | ??Os | ??Ir | ??Pt | ??Au | ??Hg | ??Tl | ??Pb | |||||
| ??Ac | |||||||||||||||||
| ??Lanthanides | ??Ce | ??Pr | ??Nd | ??Pm | ??Sm | ??Eu | ??Gd | ??Tb | ??Dy | ??Ho | ??Er | ??Tm | ??Yb | ??Lu |
| ??Actinides | ??Th | ??Pa | ??U | ??Np | ??Pu | ??Am |
Formula 2 formulas 3
Formula 4 formulas 5
Formula 6 formulas 7
The structure of phthalocyanine molecule makes it have highly stable characteristic, for example acidproofly, alkaline-resisting, water-fast soaks, heat-resisting, fast light and anti-various organic solvent.The heat decomposition temperature of general phthalocyanine compound is more than 450 ℃, and the solubility in organic solvent is minimum, and majority is water-soluble hardly.
Introducing functional group or phthalocyanine-like compound is made polymer in phthalocyanine-like compound, is the effective way that strengthens its dissolubility and improve its processing characteristics.
Have substituent phthalocyanine and compare with general unsubstituted phthalocyanine very strong self assembly ability is arranged,, be assembled into the structure of the similar folded coin of column because the plane armaticity of phthalocyanine ring makes it can n-n overlapping.
Because the electronic structure of phthalocyanine has highest occupied molecular orbital higher than virgin metal ion (HOMO) and lower lowest unoccupied molecular orbital (LUMO), promptly because of the influence of the big ring distance between the frontier molecular orbital energy levels of transition metal ions that furthered, thereby make metal ion in the phthalocyanine have the dual-use function of electron donor and receptor acting concurrently.So the phthalocyanines complex has more than the better catalytic performance of " freedom " transition metal ions and stronger selectivity, and be the electron transfer process in essence in the catalytic reaction that has phthalocyanine to participate in.The chemical property of metal phthalocyanine derivative is highly stable, catalytic reaction can take place by the axial coordination of reactant molecule and metal, aromatic rings had both had the characteristic of electron donor, the characteristic that has electron acceptor again, it is tied nucleophobic ability and can regulate by the substituting group that conversion metal and phthalein be educated ring periphery. these characteristics determined good catalytic performance and other performances of metal phthalocyanine derivative.
Metal phthalocyanine and derivative thereof have following feature:
1. aromatic series M electronics is gripped on whole four azaindole rings altogether, and the cavity energy that is positioned at the ring center holds multiple metallic element, and metallic element can form complex compound with phthalocyanine;
2. grip big molecule altogether and present flatness highly, catalytic reaction can take place on the axial location on this plane;
3. aromatic rings had both had the characteristic of electron donor, had the characteristic of electron acceptor again;
4. chemical property is highly stable.
The above-mentioned feature of metal phthalocyanine and derivative thereof makes them very suitable to catalyst.The catalysis behavior of metal phthalocyanine is similar to biology enzyme.Therefore, the catalytic performance of metal phthalocyanine is relevant with the catalytic performance of enzyme, and special catalytic performance with " plan enzyme " is closely related.
Phthalocyanine complex can mainly be because following reason as catalyst:
1) can form the metal complex that catalysis is played an important role with metal ion;
2) formed metal complex is resistant to elevated temperatures;
3) because the conjugated nature of the part of system own, formed complex compound all is a plane, and the part Cheng Jian that can be other stays two rooms;
4) phenyl ring of the big conjugated system of composition can be introduced electron-withdrawing group or donor residues, changes the variation of whole system electron distributions with this;
5) formed complex compound can be dissolved in the organic solvent, thereby is the physical property condition of providing convenience of research metal ion under solution state.
Experimental results show that the principal element that influences catalytic process has following three aspects in the reaction and decomposition reaction that aerobic at phthalocyanine catalytic, hydrogen participates in:
1) influence of metal ion in the identical complexing ring;
2) identical central metal ion, the shadow of the structure of outer complexing ring and substituting group part to;
3) influence of outer complexing ring and central metal chelating point.
Other several frequently seen phthalocyanine compounds are as follows:
Formula 8 formulas 9
The phthalocyanine compound that tetra-tert replaces as shown in Equation 8, M=Fe wherein, Co, Ni, Mg, metals such as Zn.
The structure of phthalocyanine green is to be generated by the copper phthalocyanine chlorination as shown in Equation 9.
Formula 10 formulas 11 formulas 12
Four alkoxyl phthalocyanines have four kinds of isomers, and formula 10 is its a kind of isomers.Formula 11 is the structural formula of phthalocyanine leuco compound salt.Formula 12 is quaternary amine alkalization phthalocyanine cobalts.Also having phthalocyanine-like compounds such as O-phthalic phthalimide methyl copper phthalocyanine, neighbours' BIDA Base Metal phthalocyanine, sulfonic group phthalimidomethyl Phthalocyanine Zinc, quaternary amine alkalization phthalocyanine, four phenoxy group magnesium phthalocyanine, manganese, aluminium, zinc in addition all is the compound that adopts among the present invention.
In addition, the binuclear phthalocyanine of two shared phenyl ring of phthalocyanine ring, plane binuclear phthalocyanine zinc that the alkoxyl that is connected with anthracene by phenyl ring and naphthalene replaces and phthalein work cobalt, and double-core sulfonated phthalocyanine copper has good catalytic performance.
The phthalocyanine molecule can by different polymerization methods respectively with organic and inorganic reagent self-polymerization, can obtain having the polymer of various different performances.
The polymerized phthalocyanine that the connected mode and the type of used polymerized phthalocyanine has (1) to be made of part, the part of such polymerized phthalocyanine is the part of polymeric chain, has very high heat endurance, and good catalysis characteristics is arranged.As 1,2,4,5-pyromellitonitrile or derivatives thereof.(2) coplane is piled up polymer.Such polymerized phthalocyanine is that the metal ion by coordination conspires to create, and (3) link polymerized phthalocyanine on the polymeric chain by covalent bond, and the part of such polymerized phthalocyanine is linked on the polymeric chain by covalent bond.(4) by the polymerized phthalocyanine on the polymeric chain to body formation coordinate bond or electrostatic interaction formation.(5) doping type, with phthalocyanine with physical mechanical mix in the polymer chain of organic or inorganic.The concrete polymerization phthalein mountain valley with clumps of trees and bamboo has poly-tetramino phthalocyanine cobalt, the compound of poly-tetramino CuPc and formula 13 structures (TVPc forms by containing two key phthalocyanines and VCz mixed polymerization) etc.
Formula 13
Many ring metal phthalocyanine compounds (as the metal phthalocyanine polymer of the big conjugation of 2 to 9 rings), hydrolyzed product water soluble, dimethylacetylamide isopolarity solvent, more convenient when the phthalocyanine compound that solubility property is good is used, and the phthalocyanine of slightly solubility can be used in the composite filter tip.
Have the phthalocyanin structure compound (the gorgeous blue IF3G of phthalocyanin is the intermediate of a metalloid phthalocyanine. can be on the acetate fiber or third fibre generate the corresponding metal phthalocyanine through reaction).Since can directly generate phthalocyanine with the acetate fiber or third fibre, therefore better with the binding ability of fibril.
The chemical constitution of the gorgeous blue IF3G of phthalocyanin is 1,3-diimino isoindoline (nitro salt also can).Chemical structural formula is:
In the presence of reducing agent, the gorgeous blue IF3G reaction of cupric salt and phthalocyanin can directly generate copper phthalocyanine on acetate fiber.
Said phthalocyanine-like compound also can be crown ether phthalocyanine or phthalocyanine crown ether among the present invention.Phthalocyanine can combine well with crown ether, crown ether also has special nature, coordination characteristic according to crown ether, crown ether pore size and cationic diameter are complementary, when interacting, both produce maximum electrostatic force, the bond energy that generates key is the highest, and complex is the most stable and crown ether is also the highest to the selectivity of this ion.The size of ring was regulated when the crown ether pore size can synthesize by crown ether, and the flexibility of regulating when synthetic has determined the alternative to different ions or substance classes complexing.Crown ether can form particular compound with phthalocyanines.
The structural formula of typical crown ether phthalocyanine combination is suc as formula 14 (1), shown in two kinds of structures of (2):
1:m=1 wherein, n=0, M=H2 15CRH2Pc
2：m＝1，n＝0，M＝Zn???????15CRZnPc
3：m＝1，n＝1，M＝Cu???????17CRCuPc
4：m＝1，n＝1，M＝Zn???????17CRZnPc
5：m＝2，N＝0，M＝H2???????18CRH2Pc
6：m＝2，n＝0，M＝Fe(III)??18CRFe(III)PcC1
7：m＝2，n＝0，M＝Fe(II)???18CRFe(II)Pc
Crown ether phthalocyanine structure (1) crown ether phthalocyanine structure (2)
Formula 14
M in the formula 14 and the value of n are not limited to 0-2, can adjust amplification according to the ion of crown ether institute complexing or the size of material; What engage in the phthalocyanine hole also is not limited only to H or the above-mentioned configuration metal ions Zn of enumerating, Fe etc., also comprises other metal ions that are fit to this acupuncture point.
In the structure of crown ether phthalocyanine, because crown ether cycle has the ability that combines with alkali metal or alkaline-earth metal ions, for the metal ion of ionic radius less than crown ether hole radius, the cavity that can pass parallel crown ether is realized the conducting of ion.In this system, the intermolecular binding of phthalocyanine is finished by molecular separating force, and the solubility property of this compounds does not resemble poly-silica phthalein to be reduced along with the increase of the degree of polymerization blue or green, thereby has made things convenient for its use as the flue gas harm-reducing agent.
Said phthalocyanine-like compound can also be the combination of phthalocyanine and porphyrin among the present invention, and the combination of phthalocyanine and porphyrin also has and well falls harmful effect, and the structural formula shown in the formula 15 is a kind of mode in conjunction with (but being not limited only to).
Formula 15
Phthalocyanine-like compound is as the application of cigarette harm-reducing agent, specifically can by but be not limited to following method and realize:
(1) use in filter tip: A, whole use in vinegar fibre, third fibre.B, segmentation use (employing composite methods) in vinegar fibre, third fibre.
(2) add the application in man-hour at fibril: when production vinegar fibre was fine with third, soon harm-reducing agent made an addition in the prescription of the vinegar fibre or third fiber, makes it to become the some of fibril in production.Soon phthalocyanine or phthalocyanine derivates dissolve fully or are dispersed in the acetate fiber or third fibre, make the filter tip that harmful function falls in the tool that reaches international smoking standard specification requirement with this acetic acid or third fibre.
(3) directly in pipe tobacco or in cigarette paper, use.Can be with harm-reducing agent through dissolving or directly adding in the pipe tobacco or in the cigarette paper.
The invention has the beneficial effects as follows that phthalocyanine-like compound has tangible reduction effect to materials such as the harmful substance in the flue gas: CO, nitrogen oxide, aldehydes, amines, can also remove heavy metal ion, cancellation free radical.For the application and development of phthalocyanine-like compound provides a kind of new wide prospect.
The specific embodiment
Embodiment 1
Direct bright blue GL (CuPc sulfonic acid) 1g is dissolved in the water of 100ml, is mixed with the flue gas harm-reducing agent, and the harm-reducing agent that makes evenly is sprayed on the vinegar fibre, and drying, equilibrium water conten are made the filter tip that reaches international smoking standard specification requirement.By the parallel detection of international smoking standard, collect the tar of contrast and sample respectively on the glass fibre filter disc of Cambridge.Analyze with electronics spin resonance spectroscopy (ESR), measure the variation of free radical in the tar.TPM is measured and is adopted automatic smoking machine one glass fibre filter disc method, nicotine to measure the employing photometry, and CO measures a non-ir scattering method in the CO employing cigarette smoke.After testing, the harm-reducing agent that adds in the cigarette smoking process has tangible reduction effect to the pernicious gas CO in the smog, nitrogen oxide, free radical, carcinogen BaP etc.
Embodiment 2
Direct bright blue GL (CuPc sulfonic acid) 1g is dissolved in the water of 100ml, is mixed with the flue gas harm-reducing agent, and mixture evenly is sprayed on the 3Kg pipe tobacco, and drying, equilibrium water conten are made the cigarette that reaches international smoking standard specification requirement.By the parallel detection of international smoking standard, collect the tar of contrast and sample respectively on the glass fibre filter disc of Cambridge.Analyze with electronics spin resonance spectroscopy (ESR), measure the variation of free radical in the tar.TPM is measured and is adopted automatic smoking machine one glass fibre filter disc method, nicotine to measure the employing photometry, and CO measures a non-ir scattering method in the CO employing cigarette smoke.After testing, the harm-reducing agent that adds in the cigarette smoking process has tangible reduction effect to the pernicious gas CO in the smog, nitrogen oxide, free radical, carcinogen BaP etc.
Embodiment 3
Substantially the same manner as Example 1, difference is with sulfonated phthalocyanine cobalt as cigarette harm-reducing agent.
Embodiment 4
Substantially the same manner as Example 2, difference is that with sulfonated phthalocyanine cobalt be as cigarette harm-reducing agent.
Embodiment 5
Phthalocyanine Green G (C.I face material green 7) 1g is mixed with the flue gas harm-reducing agent with the ethanol of 100ml, and mixture evenly is sprayed on the vinegar fibre, and drying, equilibrium water conten are made and reached the filter tip that international smoking standard specification requires.After testing, the harm-reducing agent that adds in the cigarette smoking process has tangible reduction effect to the pernicious gas CO in the smog, nitrogen oxide, free radical, carcinogen BaP etc.
Embodiment 6
Phthalocyanine Green G 1g is mixed with the flue gas harm-reducing agent with the ethanol of 100ml, and mixture evenly is sprayed on the 3Kg pipe tobacco, and drying, equilibrium water conten are made and reached the cigarette that international smoking standard specification requires.After testing, in the cigarette smoking process, the pernicious gas CO in the smog, nitrogen oxide, free radical, carcinogen BaP etc. there is tangible reduction effect.
Embodiment 7
Substantially the same manner as Example 2, difference is with tetracarboxylic metal phthalocyanine (suc as formula 3, M is an iron) as cigarette harm-reducing agent.
Embodiment 8
Substantially the same manner as Example 1, difference is with tetracarboxylic metal phthalocyanine (suc as formula 3, M is an iron) as cigarette harm-reducing agent.
Embodiment 9
Substantially the same manner as Example 2, difference is that 2,3,6,7,10,11,14,15 is-COOH that M is an iron, as cigarette harm-reducing agent with eight carboxyl metal phthalocyanines.
Embodiment 10
Substantially the same manner as Example 1, difference is that 2,3,6,7,10,11,14,15 is-COOH that M is an iron, as cigarette harm-reducing agent with eight carboxyl metal phthalocyanines.
Embodiment 11
Substantially the same manner as Example 5, difference is with disulfo two phthalimide methyl Phthalocyanine Zinc (ZnPcS2P2) as cigarette harm-reducing agent.
Embodiment 12
Substantially the same manner as Example 6, difference is with disulfo two phthalimide methyl Phthalocyanine Zinc (ZnPcS2P2) as cigarette harm-reducing agent.
Embodiment 13
Substantially the same manner as Example 5, difference is with tetranitro phthalocyanine cobalt as cigarette harm-reducing agent.
Embodiment 14
Substantially the same manner as Example 6, difference is with tetranitro phthalocyanine cobalt as cigarette harm-reducing agent.
Embodiment 15
Substantially the same manner as Example 5, difference is with the tetracarboxylic manganese phthalocyanine as cigarette harm-reducing agent.
Embodiment 16
Substantially the same manner as Example 6, difference is with the tetracarboxylic manganese phthalocyanine as cigarette harm-reducing agent.
Embodiment 17
After TiOPc (TiOPc) is mixed into 2g with porphyrin vanadyl (VOTPP) in 1: 1 ratio, join in the 200ml butanone solvent, be mixed with the flue gas harm-reducing agent, mixture evenly is sprayed on the 3Kg pipe tobacco, drying, equilibrium water conten are made the cigarette that reaches international smoking standard specification requirement.After testing, the harm-reducing agent that adds in the cigarette smoking process has tangible reduction effect to the pernicious gas CO in the smog, nitrogen oxide, free radical, carcinogen BaP etc.
Embodiment 18
After TiOPc (TiOPc) is mixed into 2g by a certain percentage with porphyrin vanadyl (VOTPP), join in the 200ml butanone solvent, be mixed with the flue gas harm-reducing agent, mixture evenly is sprayed on the vinegar fibre, drying, equilibrium water conten are made the filter tip that reaches international smoking standard specification requirement.After testing, the harm-reducing agent that adds in the cigarette smoking process has tangible reduction effect to the pernicious gas CO in the smog, nitrogen oxide, free radical, carcinogen BaP etc.
Embodiment 19
Substantially the same manner as Example 5, difference is with having the phthalocyanine derivates (M is an iron) of formula 2 structures as cigarette harm-reducing agent.
Embodiment 20
Substantially the same manner as Example 6, difference is with having the phthalocyanine derivates (M is an iron) of formula 2 structures as cigarette harm-reducing agent.
Embodiment 21
Substantially the same manner as Example 5, difference is with poly-tetramino CuPc as cigarette harm-reducing agent.
Embodiment 22
Substantially the same manner as Example 6, difference is with poly-tetramino CuPc as cigarette harm-reducing agent.
Embodiment 23
Substantially the same manner as Example 5, difference is with having the phthalocyanine derivates (M is a cobalt) of formula 4 structures as cigarette harm-reducing agent.
Embodiment 24
Substantially the same manner as Example 6, difference is with having the phthalocyanine derivates (M is a cobalt) of formula 4 structures as cigarette harm-reducing agent.
Embodiment 25
Substantially the same manner as Example 5, difference is with having the phthalocyanine derivates (M is a zinc) of formula 5 structures as cigarette harm-reducing agent.
Embodiment 26
Substantially the same manner as Example 6, difference is with having the phthalocyanine derivates (M is a zinc) of formula 5 structures as cigarette harm-reducing agent.
Embodiment 27
Substantially the same manner as Example 5, difference is with having the phthalocyanine derivates (M is a cobalt) of formula 6 structures as cigarette harm-reducing agent.
Embodiment 28
Substantially the same manner as Example 6, difference is with having the phthalocyanine derivates (M is a cobalt) of formula 6 structures as cigarette harm-reducing agent.
Embodiment 29
Substantially the same manner as Example 5, difference is with direct light turquoise blue GB (for having the compound of copper phthalocyanine sulfonamide and ichthyodin (sodium) component structure) as cigarette harm-reducing agent.
Embodiment 30
Substantially the same manner as Example 6, difference is with direct light turquoise blue GB (for having the compound of copper phthalocyanine sulfonamide and ichthyodin (sodium) component structure) as cigarette harm-reducing agent.
Embodiment 31
Substantially the same manner as Example 5, difference is with reactive turquoise blue K-GL (having copper phthalocyanine one chloro-s-triazine type structure) as cigarette harm-reducing agent.
Embodiment 32
Substantially the same manner as Example 6, difference is with reactive turquoise blue K-GL (having copper phthalocyanine one chloro-s-triazine type structure) as cigarette harm-reducing agent.
Embodiment 33
The gorgeous blue IF3G of phthalocyanin (chemical constitution: 1,3-diimino isoindoline) 10g in the presence of reducing agent, with cupric salt and the gorgeous blue IF3G reaction of phthalocyanin, direct generation copper phthalocyanine on acetate fiber.Drying, equilibrium water conten are made the filter tip that reaches international smoking standard specification requirement.After testing, the harm-reducing agent that adds in the cigarette smoking process is to the pernicious gas CO in the smog, and nitrogen oxide, free radical, carcinogen BaP etc. have tangible reduction effect.
Embodiment 34
The gorgeous blue IF3G of phthalocyanin (chemical constitution: 1,3-diimino isoindoline) 10g in the presence of reducing agent, with cupric salt and the gorgeous blue IF3G reaction of phthalocyanin, direct generation copper phthalocyanine on third fibre.Drying, equilibrium water conten are made the filter tip that reaches international smoking standard specification requirement.After testing, the harm-reducing agent that adds in the cigarette smoking process has tangible reduction effect to the pernicious gas CO in the smog, nitrogen oxide, free radical, carcinogen BaP etc.
Embodiment 35
The gorgeous blue IF3G of phthalocyanin (chemical constitution: 1,3-diimino isoindoline) 10g in the presence of reducing agent, with cupric salt and the gorgeous blue IF3G reaction of phthalocyanin, direct generation copper phthalocyanine on pipe tobacco.Drying, equilibrium water conten are made behind the cigarette after testing, and the harm-reducing agent that adds in the cigarette smoking process has tangible reduction effect to the pernicious gas CO in the smog, nitrogen oxide, free radical, carcinogen BaP etc.
Embodiment 36
Substantially the same manner as Example 5, difference is with having the phthalocyanine derivates (M is a zinc) of formula 8 structures as cigarette harm-reducing agent.
Embodiment 37
Substantially the same manner as Example 6, difference is with having the phthalocyanine derivates (M is a zinc) of formula 8 structures as cigarette harm-reducing agent.
Embodiment 38
Substantially the same manner as Example 5, difference is with having the phthalocyanine derivates (M is a cobalt) of formula 10 structures as cigarette harm-reducing agent.
Embodiment 39
Substantially the same manner as Example 6, difference is with having the phthalocyanine derivates (M is a cobalt) of formula 10 structures as cigarette harm-reducing agent.
Embodiment 40
Substantially the same manner as Example 5, difference is with having the phthalocyanine derivates of formula 11 structures as cigarette harm-reducing agent.
Embodiment 41
Substantially the same manner as Example 6, difference is with having the phthalocyanine derivates of formula 11 structures as cigarette harm-reducing agent.
Embodiment 42
Substantially the same manner as Example 5, difference is with O-phthalic phthalimide methyl copper phthalocyanine as cigarette harm-reducing agent.
Embodiment 43
Substantially the same manner as Example 6, difference is with O-phthalic phthalimide methyl copper phthalocyanine as cigarette harm-reducing agent.
Embodiment 44
Substantially the same manner as Example 5, difference is with neighbours' BIDA Base Metal zinc phthalocyanine as cigarette harm-reducing agent.
Embodiment 45
Substantially the same manner as Example 6, difference is with neighbours' BIDA Base Metal zinc phthalocyanine as cigarette harm-reducing agent.
Embodiment 46
Substantially the same manner as Example 5, difference is with sulfonic group phthalimidomethyl Phthalocyanine Zinc as cigarette harm-reducing agent.
Embodiment 47
Substantially the same manner as Example 6, difference is with sulfonic group phthalimidomethyl Phthalocyanine Zinc as cigarette harm-reducing agent.
Embodiment 48
Substantially the same manner as Example 5, difference is with poly-tetramino phthalocyanine cobalt as cigarette harm-reducing agent.
Embodiment 49
Substantially the same manner as Example 6, difference is with poly-tetramino phthalocyanine cobalt as cigarette harm-reducing agent.
Embodiment 50
Substantially the same manner as Example 5, difference is with having the phthalocyanine derivates (M is a zinc) of formula 14 crown ether phthalocyanine structure (1) structures as cigarette harm-reducing agent.
Embodiment 51
Substantially the same manner as Example 6, difference is with having the phthalocyanine derivates (M is a zinc) of formula 14 crown ether phthalocyanine structure (1) structures as cigarette harm-reducing agent.
Embodiment 52
Substantially the same manner as Example 5, difference is with the combination with the phthalocyanine of formula 15 structures and porphyrin as cigarette harm-reducing agent.
Embodiment 53
Substantially the same manner as Example 6, difference is with the combination with the phthalocyanine of formula 14 structures and porphyrin as cigarette harm-reducing agent.
Embodiment 54
Direct bright blue GL (CuPc sulfonic acid) 50g is dissolved in the triacetyl glycerine solvent of 5000ml, is mixed with the flue gas harm-reducing agent, through common high-speed filter-stick forming device, makes the filter tip that reaches international smoking standard specification requirement.By the parallel detection of international smoking standard, collect the tar of contrast and sample respectively on the glass fibre filter disc of Cambridge.Analyze with electronics spin resonance spectroscopy (ESR), measure the variation of free radical in the tar.TPM is measured and is adopted automatic smoking machine one glass fibre filter disc method, nicotine to measure the employing photometry, and CO measures a non-ir scattering method in the CO employing cigarette smoke.After testing, the harm-reducing agent that adds in the cigarette smoking process has tangible reduction effect to the pernicious gas CO in the smog, nitrogen oxide, free radical, carcinogen BaP etc.
Embodiment 55
Basic identical with embodiment 54, difference is with the combination with the phthalocyanine of formula 15 structures and porphyrin as cigarette harm-reducing agent.
Embodiment 56
Direct bright blue GL (CuPc sulfonic acid) 1kg interpolation is used for the fine factory formula of vinegar, makes the fine raw material of vinegar through the spray silk, makes the filter tip that reaches international smoking standard specification requirement through common high-speed filter-stick forming device.By the parallel detection of international smoking standard, collect the tar of contrast and sample respectively on the glass fibre filter disc of Cambridge.Analyze with electronics spin resonance spectroscopy (ESR), measure the variation of free radical in the tar.TPM is measured and is adopted automatic smoking machine one glass fibre filter disc method, nicotine to measure the employing photometry, and CO measures a non-ir scattering method in the CO employing cigarette smoke.After testing, the harm-reducing agent that adds in the cigarette smoking process has tangible reduction effect to the pernicious gas CO in the smog, nitrogen oxide, free radical, carcinogen BaP etc.
Embodiment 57
Basic identical with embodiment 56, difference is with the combination with the phthalocyanine of formula 15 structures and porphyrin as cigarette harm-reducing agent.
Embodiment 58
Direct bright blue GL (CuPc sulfonic acid) 1kg interpolation is used for the third fine factory formula, makes the third fine raw material through the spray silk, makes through high-speed filter-stick forming device to reach the filter tip that international smoking standard specification requires.By the parallel detection of international smoking standard, collect the tar of contrast and sample respectively on the glass fibre filter disc of Cambridge.Analyze with electronics spin resonance spectroscopy (ESR), measure the variation of free radical in the tar.TPM is measured and is adopted automatic smoking machine one glass fibre filter disc method, nicotine to measure the employing photometry, and CO measures a non-ir scattering method in the CO employing cigarette smoke.After testing, the harm-reducing agent that adds in the cigarette smoking process has tangible reduction effect to the pernicious gas CO in the smog, nitrogen oxide, free radical, carcinogen BaP etc.
Embodiment 59
Basic identical with embodiment 58, difference is with the combination with the phthalocyanine of formula 15 structures and porphyrin as cigarette harm-reducing agent.
Embodiment 60
Direct bright blue GL (CuPc sulfonic acid) 1kg interpolation is used for the cigarette paper factory formula, makes with this cigarette paper production to reach the cigarette that international smoking standard specification requires.By the parallel detection of international smoking standard, collect the tar of contrast and sample respectively on the glass fibre filter disc of Cambridge.Analyze with electronics spin resonance spectroscopy (ESR), measure the variation of free radical in the tar.TPM is measured and is adopted automatic smoking machine one glass fibre filter disc method, nicotine to measure the employing photometry, and CO measures a non-ir scattering method in the CO employing cigarette smoke.After testing, the harm-reducing agent that adds in the cigarette smoking process has tangible reduction effect to the pernicious gas CO in the smog, nitrogen oxide, free radical, carcinogen BaP etc.
Embodiment 61
Substantially the same manner as Example 5, difference is with Phthalocyanine Green G (C.I face material green 36, a kind of yellowish phthalocyanine green series) as cigarette harm-reducing agent.
Embodiment 62
Substantially the same manner as Example 6, difference is with Phthalocyanine Green G (C.I face material green 36, a kind of yellowish phthalocyanine green series) as cigarette harm-reducing agent.
Embodiment 63
Substantially the same manner as Example 5, difference is with four phenoxy group magnesium phthalocyanine as cigarette harm-reducing agent.
Embodiment 64
Substantially the same manner as Example 6, difference is with four phenoxy group magnesium phthalocyanine as cigarette harm-reducing agent.
Embodiment 65
Direct bright blue GL (CuPc sulfonic acid) 50g uses active carbon adsorption, makes to reach the two-period form composite filter-tip that international smoking standard specification requires.By the parallel detection of international smoking standard, collect the tar of contrast and sample respectively on the glass fibre filter disc of Cambridge.Analyze with electronics spin resonance spectroscopy (ESR), measure the variation of free radical in the tar.TPM is measured and is adopted automatic smoking machine one glass fibre filter disc method, nicotine to measure the employing photometry, and CO adopts non-ir scattering method.After testing, the harm-reducing agent that adds in the cigarette smoking process has tangible reduction effect to the pernicious gas CO in the smog, nitrogen oxide, free radical, carcinogen BaP etc.
Embodiment 66
Basic identical with embodiment 65, difference is with four phenoxy group aluminum phthalocyanine as cigarette harm-reducing agent.
Embodiment 67
Substantially the same manner as Example 2, difference is with quaternary amine alkalization phthalocyanine cobalt as cigarette harm-reducing agent.
Embodiment 68
Substantially the same manner as Example 2, difference is with TVPc (seeing formula 13) as cigarette harm-reducing agent.
Claims (6)
1, phthalocyanine-like compound is as the application of cigarette harm-reducing agent.
According to of the application of the said phthalocyanine-like compound of claim 1, it is characterized in that 2, said phthalocyanine-like compound is to be that the phthalocyanine or derivatives thereof of formula I or phthalocyanin are independent or compoundly constitute by structure as cigarette harm-reducing agent,
M wherein is the metallic atom of hydrogen or Pd, Co, Ni, Cu, Zn, Mn, Fe, Mn, Cr, Sn, Pt, and the substituting group on the C1-C16 is hydrogen, alkyl, alkoxyl, alcoxyl hydroxyl, halogen, sulfo group, amido or amino.
According to of the application of the said phthalocyanine-like compound of claim 1, it is characterized in that 3, said phthalocyanine-like compound is binuclear phthalocyanine or poly-phthalocyanine as cigarette harm-reducing agent.
According to of the application of the said phthalocyanine-like compound of claim 1, it is characterized in that 4, said phthalocyanine-like compound is crown ether phthalocyanine or phthalocyanine crown ether as cigarette harm-reducing agent.
According to of the application of the said phthalocyanine-like compound of claim 1, it is characterized in that 5, said phthalocyanine-like compound is the combination of phthalocyanine and porphyrin as cigarette harm-reducing agent.
6, according to of the application of the said phthalocyanine-like compound of claim 1, it is characterized in that said compound is a phthalocyanin as cigarette harm-reducing agent.
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| CN200510040907.1A CN1709171A (en) | 2005-07-06 | 2005-07-06 | Use of phthalocyanin compound as cigarette harm-reducing agent |
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