CN102703053A - Ethylene-substituted reversible force-changing wave material and applications thereof - Google Patents
Ethylene-substituted reversible force-changing wave material and applications thereof Download PDFInfo
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- CN102703053A CN102703053A CN2012101484900A CN201210148490A CN102703053A CN 102703053 A CN102703053 A CN 102703053A CN 2012101484900 A CN2012101484900 A CN 2012101484900A CN 201210148490 A CN201210148490 A CN 201210148490A CN 102703053 A CN102703053 A CN 102703053A
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Abstract
The invention relates to a reversible force-changing wave material and applications thereof, and particularly relates to an ethylene-substituted reversible force-changing wave material and applications thereof. The material shows different electromagnetic adsorptions or/and radiations before/after being suffered from external force; the electromagnetic wave adsorptions and/or radiations caused by the external force can be recovered reversibly. The material can be compounded with papers, polymers, inks and so on, and is applied in fields such as display apparatus, sensing detection, information storage, safe ink, counterfeit prevention, military camouflage and optical telecommunication and the like.
Description
Technical field
The present invention relates to a kind of reversible power and cause and become wave material and application thereof, particularly relating to the substituted ethylene verivate is that the reversible power of activeconstituents causes and becomes wave material and application thereof.
Background technology
It is one type of novel " intelligence " material that grew up in nearly ten years that power causes off-color material, belongs to the research focus that becomes wave material, it can through external force stimulate and change accordingly its to the absorption of light or (with) radiation.The approach that realizable force causes variable color has two kinds usually: a kind of altered chemical structure that is chemical reaction causes causes; This type usually occurs in the reaction process of two kinds of chemical substances; Material before and after the reaction changes, and under most situation, this variation is irreversible; Another kind is that the Material Physics structure power that causes that changes causes variable color; Show that mainly in the change of molecular configuration, conformational change and accumulation mode, the chemical bond of molecule itself is not destroyed, under suitable condition; This variation is a reversible, thereby makes its change in color reversible.
Color changeable makes these materials have potential to use in demonstration, sensing, information storage, safety ink, field such as false proof.With present anti-forgery ink is example, and except magnetic ink, fluorescent ink, temperature sensitive ink etc., wiping variable color printing ink also is used as anti-forgery ink and is used for Valued Securities and trade marks such as check, banknote.Chinese patent CN1201213 discloses a kind of wiping changeable color ink; Its principle is CB developer coating and CF chromogenic reagent reacted and develop the color; Chinese patent CN1176982 also discloses a kind of molecular distinguishing type solid phase anti-counterfeit tech; Its principle also is two kinds of substance reaction variable colors, and their common shortcoming all is poor, the instability of patience.In enclose patent CN1424369 and disclose the wiping changeable color ink of a kind of perylene compound as one-component; Through the friction of certain strength white paper, its color becomes redness from blackish green under visible light, and does not have any absorption in the near-infrared region; Its patience is good, stable performance.But all these technology, the colour-change after its friction all is disposable, irreversible, can make the outward appearance that is labeled thing bring irreversible variation, is restricted greatly for its application on check, banknote." reversible piezochromic systems " that Chinese patent CN1938388 discloses U.S. sun Chemical Corporation is used to prepare printing-ink, and to be applied to banknote false proof; Its principle is based on friction and makes to electron compound and receive to develop the color through chemical reaction between the electron compound; After frictional force removes, automatically with arriving stressed color before again.But its deficiency is that heatproof is lower than 300 degrees centigrade, ageing resistance is poor, work-ing life is short and pressure sensibility is poor, and the pressure back color of decorporating automatically replies in addition, makes it the of short duration and poor controllability of color status.Chinese patent CN102260491 discloses " a kind of piezallochromy powdered material and preparation method thereof "; It is the inorganic solid solution, oxide powder that a kind of two specific components are mixed with; Be applicable to stress monitoring; Can make it recover original color to reuse through grinding, but its as inorganic powder be difficult for Application of composite such as polymkeric substance, printing ink in fields such as safety anti-fakes.
Summary of the invention
A kind of reversible power that the present invention proposes causes the change wave material and has advantages of excellent stability; Under illumination; Show before and after the external force effect different absorption of electromagnetic wave or (with) radiating changes, and under certain condition, the absorption of electromagnetic wave that this type external force causes or (with) radiating changes can reversible recovery.
This reversible power causes the change wave material and is the substituted ethylene verivate.Its molecular structural formula is:
Ar wherein
1(or H), Ar
2(or R
2), Ar
3(or R
3), Ar
4(or R
4) can be identical or different substituting groups, but contain an aromatic substituent at least.Ar wherein
1, Ar
2, Ar
3, Ar
4Can be phenyl, naphthyl, anthryl and the derived structure that has single or a plurality of secondary substituted radicals thereof, or any aromatic ring or fragrant heterocycle and have the derived structure of single (or a plurality of) secondary substituted radical.
The one-level substituent R
2, R
3, R
4Can be F, Cl, Br, I, R, CX
1 1, CX
1X
2X
3, NO
2, OR, SR, SO
2R, SOR, SO
3R, NHR, NRR
1, CHO, CH
2OR, CO
2R, OCOR, OCOCH
2R, CHYCHO, CY
2CHO, CHYCO
2R, CHYOR, SiX
1X
2X
3In any atom or atomic group, can also be that any aromatic ring such as fluorenes, pyridine, thiophene or fragrant heterocycle structure and two (many) level replaces structure; X wherein
1, X
2, X
3And Y, can be respectively H, F, Cl, Br, I, NO
2, OR, SR, NHR, NRR
1, (CH
2)
nCHO, (CH
2)
nCO
2R, (CH
2)
nX
1, C
2+4nH
2n+4, any atom or atomic group among the R; R wherein and R
1Can be identical or different atom or atomic group, R and R
1Can be respectively H, C
nH
2n 1, C
nH
2n-1, C
nH
2n 3, C
6+nH
5-2n, C
2+4nH
2n+4In arbitrary atom or atomic group.In the compound or atomic group of above-mentioned different structure general formula, the numerical value of n both can be identical, also can be different, and the numerical value of n both can be 0, also can be any integer between 1-20.
Secondary substituted radical on aromatic ring or the fragrant heterocycle can be F, Cl, Br, I, R, CX
1 3, CX
1X
2X
3, NO
2, OR, SR, SO
2R, SOR, SO
3R, NHR, NRR
1, CHO, CH
2OR, CO
2R, OCOR, OCOCH
2R, CHYCHO, CY
2CHO, CHYCO
2R, CHYOR, SiX
1X
2X
3, C
2+4nH
2n+4In any atom or atomic group, can also be that any aromatic ring such as fluorenes, pyridine, thiophene or fragrant heterocycle structure and two (many) level replaces structure; X wherein
1, X
2, X
3And Y, can be respectively H, F, Cl, Br, I, NO
2, OR, SR, NHR, NRR
1, (CH
2)
nCHO, (CH
2)
nCO
2R, (CH
2)
nX
1, C
2+4nH
2n+4, any atom or atomic group among the R; R wherein and R
1Can be identical or different atom or atomic group, R and R
1Can be respectively H, C
nH
2n+1, C
nH
2n-1, C
nH
2n-3, C
6 nH
5+2n, C
2+4nH
2n+4In arbitrary atom or atomic group.In the compound or atomic group of above-mentioned different structure general formula, the numerical value of n both can be identical, also can be different, and the numerical value of n both can be 0, also can be any integer between 1-20.Secondary substituting group on this type aromatic ring or the fragrant heterocycle can also be any ring compound except that above-mentioned atom or atomic group.
Accompanying drawing 1,2 has provided schematically respectively that single when aromatic ring is phenyl replaces and the structural formula (protection domain that is not limited to this patent is in this) during two the replacement.
Material with said structure, have that reversible power sends a telegraph that magnetic wave absorbs or (with) character of radiation variation.
This absorption of electromagnetic wave or (with) radiating is reversible change can carry out repeatedly.
This quasi-molecule can be used as active ingredient and uses separately, also can with compound uses such as paper, polymkeric substance, printing ink, be applied in numerous areas such as display device, sensing detection, information storage, safety ink, safety anti-fake, camouflage, optical communications.
Description of drawings
Fig. 1, Fig. 2 showed respectively that single when aromatic ring is phenyl replaces and disubstitutedly had a chemical structure of general formula that reversible power causes the vinyl compound that becomes wave property, wherein:
X
0Can be following atom or atomic group (H, F, Cl, Br, I, R, CX
1 3, CX
1X
2X
3, NO
2, OR, SR, SO
2R, SOR, SO
3R, NHR, NRR
1, CHO, CH
2OR, CO
2R, OCOR, OCOCH
2R, CHYCHO, CY
2CHO, CHYCO
2R, CHYOR, SiX
1X
2X
3) in any one, can also be that any aromatic ring such as benzene, naphthalene, anthracene, fluorenes, pyridine, thiophene or fragrant heterocycle structure and two (many) level replaces structure.
X
1Can be following atom or atomic group (H, F, Cl, Br, I, NO
2, OR, SR, NHR, NRR
1, (CH
2)
nCHO, (CH
2)
nCO
2R, (CH
2)
nX
0, R) in any one.
X
2Can be following atom or atomic group (H, F, Cl, Br, I, NO
2, OR, SR, NHR, NRR
1, (CH
2)
nCHO, (CH
2)
nCO
2R, (CH
2)
nX
0, R) in any one.
X
3Can be following atom or atomic group (H, F, Cl, Br, I, NO
2, OR, SR, NHR, NRR
1, (CH
2)
nCHO, (CH
2)
nCO
2R, (CH
2)
nX
0, R) in any one.
X
4Can be following atom or atomic group (H, F, Cl, Br, I, NO
2, OR, SR, NHR, NRR
1, (CH
2)
nCHO, (CH
2)
nCO
2R, (CH
2)
nX
0, R) in any one.
X
5Can be following atom or atomic group (H, F, Cl, Br, I, NO
2, OR, SR, NHR, NRR
1, (CH
2)
nCHO, (CH
2)
nCO
2R, (CH
2)
nX
0, R) in any one.
X
6Can be following atom or atomic group (H, F, Cl, Br, I, NO
2, OR, SR, NHR, NRR
1, (CH
2)
nCHO, (CH
2)
nCO
2R, (CH
2)
nX
0, R) in any one.
X
7Can be following atom or atomic group (H, F, Cl, Br, I, NO
2, OR, SR, NHR, NRR
1, (CH
2)
nCHO, (CH
2)
nCO
2R, (CH
2)
nX
0, R) in any one.
Y can be following atom or atomic group (H, F, Cl, Br, I, NO
2, OR, SR, NHR, NRR
1, (CH
2)
nCHO, (CH
2)
nCO
2R, (CH
2)
nX
0, R) in any one.
R can be following atom or atomic group (H, C
nH
2n+1, C
nH
2n 1, C
nH
2n 3, C
6+nH
5 2n) in any one.
R
1Can be following atom or atomic group (H, C
nH
2n+1, C
nH
2n 1, C
nH
2n 3, C
6+nH
5+2n) in any one.
In the compound or atomic group of above-mentioned different structure general formula, the numerical value of n both can be identical, also can be different, and the numerical value of n both can be 0, also can be any integer between 1-20.
Secondary substituting group on aromatic ring or the fragrant heterocycle can also be any ring compound except that above-mentioned atom or atomic group.
Embodiment
The present invention has provided one type and has had the compound that reversible power causes the change wave property, can be used as the active ingredient use that display device, sensing detection, information storage, safety ink, safety anti-fake, camouflage, optical communications etc. are used.Following description only is in order to let the reader of common level can understand and put into practice the principles of science of present patent application and the schematic part illustration that characteristics provide; But be not our invention of limitation in this, any the principles of science that provides based on patent specification and the application mode of products characteristics all belong in this patent protection category.
Embodiment one:
Work as X
0, X
1, X
2, X
3Be methoxyl group, and when being substituted in the contraposition of each phenyl ring, it be dissolved in the suitable solvents; Evenly be sprayed on filter paper or the printer paper, treat solvent evaporates after, on paper, do not write or the picture case with any with the hard thing of ink; Under natural light, can't see variation,, above-mentioned paper is sprayed with solvent or stifling the processing at next word or the pattern of being write that demonstrate of UV-light; Or place certain temperature baking oven certain hour, or blow certain hour with the hair dryer hot blast, or shine certain hour with ir lamp; Place under the UV-light, word of then being write or pattern disappear again.
Embodiment two:
The massfraction of active ingredient in solvent described in embodiment one is between 1/10000000th to 9,999,999/10000000ths.
Embodiment three:
The stifling or existing used solvent of sprinkling place to paper described in embodiment one can be that in methyl alcohol, ethanol, Virahol, hexanaphthene, sherwood oil, toluene, THF, chloroform, the methylene dichloride etc. one or more use simultaneously.
Embodiment four:
Exerting all one's strength described in embodiment one causes pattern or literal after the variable color, and to take off used Heating temperature be 50～300 ℃, and be 0.1～30 minute action time.
Embodiment five:
Power described in embodiment one causes the process that literal and pattern disappear after fluorescence variable color and solvent and the heat treated, can repeat n time, wherein n >=1.
Embodiment six:
Active ingredient described in embodiment one is dissolved in it in polymers soln with the certain mass mark, behind curing of coating, processes film material, has reversible power equally and causes fluorescence variable color character.
Embodiment seven:
The massfraction of active ingredient in solvent described in embodiment six is between 1/10000000th to 9,999,999/10000000ths.
Embodiment eight:
Polymkeric substance described in embodiment six can be one or more a blend in polymethylmethacrylate, PS, SE, polycarbonate, resol or the like the polymkeric substance.
Claims (7)
1. one type has the substituted vinyl compound that reversible power causes the change wave property; Show before and after the external force effect different absorption of electromagnetic wave or (with) radiation variation; And under certain condition, the absorption of electromagnetic wave that causes of this external force or (with) radiation variation can reversible recovery.
The substituted ethene derivatives of this type, molecular structural formula is:
It is characterized in that: four one-level substituent A r of ethene
1(or H), Ar
2(or R
2), Ar
3(or R
3), Ar
4(or R
4) can be identical or different substituting groups, but contain an aromatic ring substituting group at least.
2. the bad substituent A r of one-level virtue according to claim 1
1, Ar
2, Ar
3, Ar
4Can be phenyl, naphthyl, anthryl and the derived structure that has single (or a plurality of) secondary substituted radical thereof, or any aromatic ring or fragrant heterocycle and have the derived structure of single (or a plurality of) secondary substituted radical.
3. one-level alkyl substituent R according to claim 1
2, R
3, R
4Can be F, Cl, Br, I, R, CX
1 3, CX
1X
2X
3, NO
2, OR, SR, SO
2R, SOR, SO
3R, NHR, NRR
1, CHO, CH
2OR, CO
2R, OCOR, OCOCH
2R, CHYCHO, CY
2CHO, CHYCO
2R, CHYOR, SiX
1X
2X
3In any atom or atomic group, wherein X
1, X
2, X
3And Y, can be respectively H, F, Cl, Br, I, NO
2, OR, SR, NHR, NRR
1, (CH
2)
nCHO, (CH
2)
nCO
2R, (CH
2)
nX
1, C
2 4nH
2n+4, any atom or atomic group among the R; R wherein and R
1Can be identical or different atom or atomic group, R and R
1Can be respectively H, C
nH
2n 1, C
nH
2n 1, C
nH
2n 3, C
6 nH
5 n, C
2+4nH
2+4In arbitrary atom or atomic group.In the compound or atomic group of above-mentioned different structure general formula, the numerical value of n both can be identical, also can be different, and the numerical value of n both can be 0, also can be any integer between 1-20.
4. this type according to claim 2 has the aromatic ring or the fragrant heterocycle structure of single or a plurality of secondary substituted radicals, and its secondary substituted radical can be H, F, Cl, Br, I, R, CX
1 3, CX
1X
2X
3, NO
2, OR, SR, SO
2R, SOR, SO
3R, NHR, NRR
1, CHO, CH
2OR, CO
2R, OCOR, OCOCH
2R, CHYCHO, CY
2CHO, CHYCO
2R, CHYOR, SiX
1X
2X
3, C
2 1nH
2n+4In any atom or atomic group, can also be any aromatic ring or fragrant heterocycle structures such as fluorenes, pyridine, thiophene; X wherein
1, X
2, X
3And Y, can be respectively H, F, Cl, Br, I, NO
2, OR, SR, NHR, NRR
1, (CH
2)
nCHO, (CH
2)
nCO
2R, (CH
2)
nX
1, C
2+4nH
2n+4, any atom or atomic group among the R; R wherein and R
1Can be identical or different atom or atomic group, R and R
1Can be respectively H, C
nH
2n 1, C
nH
2n 1, C
nH
2n 3, C
6 nH
5+2n, C
2+4nH
2n+4In arbitrary atom or atomic group.In the compound or atomic group of above-mentioned different structure general formula, the numerical value of n both can be identical, also can be different, and the numerical value of n both can be 0, also can be any integer between 1-20.Secondary substituting group on this type aromatic ring or the fragrant heterocycle can also be any ring compound except that above-mentioned atom or atomic group.
5. reversible power according to claim 1 causes and becomes the ripple compound, and this compounds can be used as active ingredient and uses separately, also can with compound uses such as paper, polymkeric substance, printing ink.
6. in the matrix material according to claim 5, the content of active ingredient accounts between ten million of gross weight/one to 9,999,999.
7. this type active ingredient according to claim 5 and matrix material can be applied in it fields such as display device, sensing detection, information storage, safety ink, safety anti-fake, camouflage, optical communications.
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|---|---|---|---|
| CN2012101484900A CN102703053A (en) | 2012-05-15 | 2012-05-15 | Ethylene-substituted reversible force-changing wave material and applications thereof |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2012101484900A CN102703053A (en) | 2012-05-15 | 2012-05-15 | Ethylene-substituted reversible force-changing wave material and applications thereof |
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| Publication Number | Publication Date |
|---|---|
| CN102703053A true CN102703053A (en) | 2012-10-03 |
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ID=46896113
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|---|---|---|---|
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111072439A (en) * | 2019-11-25 | 2020-04-28 | 深圳大学 | Luminescent material and synthesis method and application thereof |
| CN115019626A (en) * | 2022-07-07 | 2022-09-06 | 吉林大学 | Application of thermosensitive fluorescent material in anti-counterfeiting trademark |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4912002A (en) * | 1987-11-30 | 1990-03-27 | Alps Electric Co., Ltd. | Electrophotosensitive layered article provided styryl compounds and bisazo pigment |
| CN1201213A (en) * | 1997-06-02 | 1998-12-09 | 周蓉 | Multifunction anti-fake mark and mfg. method therefor |
| JP2003040828A (en) * | 2001-07-25 | 2003-02-13 | Osaka Organic Chem Ind Ltd | Hinokitiol clathrate compound |
| CN1938388A (en) * | 2004-03-12 | 2007-03-28 | 太阳化学公司 | Reversible piezochromic systems |
-
2012
- 2012-05-15 CN CN2012101484900A patent/CN102703053A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4912002A (en) * | 1987-11-30 | 1990-03-27 | Alps Electric Co., Ltd. | Electrophotosensitive layered article provided styryl compounds and bisazo pigment |
| CN1201213A (en) * | 1997-06-02 | 1998-12-09 | 周蓉 | Multifunction anti-fake mark and mfg. method therefor |
| JP2003040828A (en) * | 2001-07-25 | 2003-02-13 | Osaka Organic Chem Ind Ltd | Hinokitiol clathrate compound |
| CN1938388A (en) * | 2004-03-12 | 2007-03-28 | 太阳化学公司 | Reversible piezochromic systems |
Non-Patent Citations (3)
| Title |
|---|
| A. PUCCI ET AL.，: ""Dichroic Properties of Bis(benzoxazolyl)stilbene and Bis(benzoxazolyl)thiophene Dispersed into Oriented Polyethylene Films: A Combined Experimental and Density Functional Theory Approach"", 《J. PHYS. CHEM. B》 * |
| B. XU ET AL.，: ""Piezofluorochromic and Aggregation-Induced-Emission Compounds Containing Triphenylethylene and Tetraphenylethylene Moieties"", 《CHEM. ASIAN J.》 * |
| X. ZHOU ET AL.，: ""Piezofluorochromism and morphology of a new aggregation-induced emission compound derived from tetraphenylethylene and carbazole"", 《NEWJ. CHEM.》 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111072439A (en) * | 2019-11-25 | 2020-04-28 | 深圳大学 | Luminescent material and synthesis method and application thereof |
| CN115019626A (en) * | 2022-07-07 | 2022-09-06 | 吉林大学 | Application of thermosensitive fluorescent material in anti-counterfeiting trademark |
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