CN110820364A - Photochromic dye emitting blue light - Google Patents

Photochromic dye emitting blue light Download PDF

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Publication number
CN110820364A
CN110820364A CN201911131979.5A CN201911131979A CN110820364A CN 110820364 A CN110820364 A CN 110820364A CN 201911131979 A CN201911131979 A CN 201911131979A CN 110820364 A CN110820364 A CN 110820364A
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substituted
compound
groups
unsubstituted
photochromic
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李健
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Ningbo Keri An Polytron Technologies Inc
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Ningbo Keri An Polytron Technologies Inc
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Priority to CN201911131979.5A priority Critical patent/CN110820364A/en
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    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
    • D06P1/004—Dyeing with phototropic dyes; Obtaining camouflage effects
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K9/00—Tenebrescent materials, i.e. materials for which the range of wavelengths for energy absorption is changed as a result of excitation by some form of energy
    • C09K9/02—Organic tenebrescent materials
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1007—Non-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1011—Condensed systems
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1014—Carbocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only heteroatom

Abstract

The invention discloses a photochromic dye emitting blue light, which comprises a photochromic material, wherein the photochromic material is a blue light emitting material, the blue light emitting material comprises any one or the combination of two or more of erbium, a compound A, a compound B, a compound C, a compound D and a compound E, the photochromic dye can have color or change the color according to absorbed light, and the cloth dyed and dyed by the photochromic dye forms photochromic cloth which has color or changes the color according to the absorbed light.

Description

Photochromic dye emitting blue light
Technical Field
The invention relates to a dye, in particular to a photochromic dye, which can be used for preparing photochromic cloth and photochromic clothes and belongs to the field of textile industry.
Background
With the development of society, the living standard of people is continuously improved, and more rigorous requirements are provided for the functionality, the comfort, the aesthetic feeling and the like of clothes. At present, clothes sewn by most fabrics lack dynamic sense, are single in color, are too monotonous and stiff, cannot bring more aesthetic feeling and fun to people, particularly young people who like pursuing fashion elements, and the fabrics with single color cannot meet the market demand and also restrict the selection of clothing designers for individual clothing fabrics. Recently, on the basis of the unchanged basic functions of clothes, people pay more and more attention to the additional efficacy of clothes, new materials of the clothes are continuously researched and developed, various efficacies of different materials are added into the clothes by using a proper process, and the functionality of the clothes is improved. Photochromic fabric refers to fabric whose color can be changed under the irradiation of light sources such as sunlight or ultraviolet light, and the color can be reversibly changed back to the original color after the light disappears.
Disclosure of Invention
The main object of the present invention is to provide a photochromic dye, a photochromic fabric and photochromic clothing, wherein the fabric and clothing dyed and finished by using the photochromic dye can have the ability of changing into different colors according to the absorbed light.
In order to solve the technical problems, the invention solves the technical scheme that the photochromic dye capable of emitting blue light comprises a photochromic material, wherein the photochromic material is a material capable of emitting blue light, the material capable of emitting blue light comprises any one or a combination of two or more of erbium, a compound A, a compound B, a compound C, a compound D and a compound E, and the compound A is a compound A
Figure 11548DEST_PATH_IMAGE001
，
Ar 1-Ar 8 in the compound A are independently selected from any one of substituted or unsubstituted aromatic hydrocarbon groups of H, C6-C30, substituted or unsubstituted condensed ring aromatic hydrocarbon groups of C6-C30, substituted or unsubstituted condensed heterocyclic groups of C6-C30, five-membered heterocyclic rings or substituted heterocyclic rings, six-membered heterocyclic rings or substituted heterocyclic rings, triarylamine groups, aryl ether groups and substituted or unsubstituted aliphatic alkyl groups of C1-C12, and Ar 1-Ar 8 are not H at the same time;
the compound B is
，
Ar 1-Ar 8 in the compound B are independently selected from any one of substituted or unsubstituted aromatic hydrocarbon groups of H, C6-C30, substituted or unsubstituted condensed ring aromatic hydrocarbon groups of C6-C30, substituted or unsubstituted condensed heterocyclic groups of C6-C30, five-membered heterocyclic rings or substituted heterocyclic rings, six-membered heterocyclic rings or substituted heterocyclic rings, triarylamine groups, aryl ether groups and substituted or unsubstituted aliphatic alkyl groups of C1-C12, and Ar 1-Ar 8 are not H at the same time;
or compound C
，
Ar 1-Ar 12 in the compound C are independently selected from one of substituted or unsubstituted aromatic hydrocarbon groups of H, C6-C30, substituted or unsubstituted condensed ring aromatic hydrocarbon groups of C6-C30, substituted or unsubstituted condensed heterocyclic groups of C6-C30, five-membered heterocyclic rings or substituted heterocyclic rings, six-membered heterocyclic rings or substituted heterocyclic rings, triarylamine groups, aryl ether groups, and substituted or unsubstituted aliphatic alkyl groups of C1-C12, Ar 1-Ar 8 are not H at the same time, Ar13 is selected from one of substituted or unsubstituted aromatic hydrocarbon groups of C6-C30, substituted or unsubstituted condensed ring aromatic hydrocarbon groups of C6-C30, and substituted or unsubstituted aliphatic alkyl groups of C1-C12;
the compound D is
Figure 598759DEST_PATH_IMAGE004
，
Wherein R1 and R2 in the compound D are independently selected from C1-C20 alkyl and substituted or unsubstituted C6-C50 aromatic hydrocarbon groups, or R1 and R2 are cyclic structures formed by connecting divalent alkylene or arylene of C2-C20, and the A1 structure is
Or
Figure 1
Any one of the above-mentioned (a) and (b),
Figure 679978DEST_PATH_IMAGE006
A2is H,
Figure 100002_4
、
Figure 5
Wherein in A1And A2R in (1)3And R6Independently selected from substituted or unsubstituted aromatic hydrocarbon radicals, A1And A2Wherein represents a substitution position with the parent nucleus, and L1 is selected from substituted or unsubstituted arylene groups of C6 to C50;
the compound E is
Figure 287337DEST_PATH_IMAGE009
。
In the above technical solution, preferably, the ink further comprises one or a combination of two or more of a basic dye, an auxiliary agent, and a resin or a paste.
The photochromic fabric is formed by dyeing and finishing photochromic dye, and further comprises a UV cut-off layer, wherein the UV cut-off layer covers the surface of the fabric, the UV cut-off layer is a coating formed by coating a UV absorbent, the UV absorbent is any one or a combination of two or more of salicylic acid esters, benzophenones, benzotriazoles, substituted acrylonitrile and triazines, and the transmittance of the UV cut-off layer to ultraviolet ray with the wavelength of 200 nm and 395nm is less than 20%.
Photochromic clothing is made of photochromic cloth.
Photochromic materials are materials that change color when excited by a light source. The molecular structure of the photochromic material can be changed under the action of light with certain wavelength and intensity, so that the absorption peak value of the photochromic material to the light is changed, namely the corresponding change of the color is changed, and the change is generally reversible. The photochromic dye provided by the invention can be formed by mixing the photochromic material provided by the invention with common dye, or can be formed by only adopting the photochromic material, namely, the content of the photochromic material is 15-100 wt%. The resin, the paste and the auxiliary agent are selected according to the use amounts of the dye and the photochromic material, and the material which has better compatibility with the dye and the photochromic material and does not influence the dyeing effect is adopted. All of them are commercially available, and for example, the assistant can be ZG-327 dye assistant manufactured by Shandong Kaya chemical Co., Ltd; the resin can adopt modified polyurethane resin XH-PU408 produced by Dongguan Asahi Yi Hua chemical industry Co.Ltd; the paste can be animal fiber printing paste of acidic and metal complex dyes produced by Shanghai Shencheng chemical industry Co.
Wherein the selected basic dye (i.e. common dye without photochromic function) may include natural dye, reactive dye, acid dye, disperse dye, etc.; the natural dye is generally plant dye, such as indigo, turmeric, etc.; the disperse dye is feinuo golden yellow P-XGTT or scarlet PD-GR or Annuo its Shenlan HGL or leap native primary color AM-SRL, and the like, and is a conventional and commonly used disperse dye sold in the market; acid dyes can be selected; one or more of red GRS, yellow GN, pinlan 6B, black AMR, bright red F-3GL, Chinese cabbage 4BL, brilliant blue G, fruit green 3GM, and orange GSN; the reactive dye can be one or more of black C-NN, red C-2B, yellow C-4G, blue C-M and navy blue C-MR. The basic dye can be obtained by commercial purchase or self-production according to the existing formula.
The photochromic material in the photochromic dye provided by the present invention may have a color or change a color according to absorbed light. The cloth dyed by the photochromic dye provided by the invention forms photochromic cloth which has color or changes color according to absorbed light.
The fabric before dyeing and finishing can be woven fabric or knitted fabric, and the woven fabric is formed by vertically interweaving warp yarns and weft yarns. The knitted fabric is formed by forming yarns or filaments into loops by using a knitting needle and then mutually stringing and sleeving the loops. The fabric before dyeing and finishing can be pure color or the original color of the fabric, and color paste prepared by the dye formula is printed on the fabric according to a preset pattern through a printing dyeing and finishing process. The dyeing and finishing process can be the same as or different from the dyeing and finishing process in the prior art.
Detailed Description
The technical solution, the implementation process and the principle thereof will be further explained with reference to the specific embodiments as follows.
Example 1
The preparation process of the photochromic cloth comprises the following steps: mixing 2% of basic dye, 5% of resin or paste, 1% of auxiliary agent and 1% of photochromic material by mass percent to form white photochromic dye, and the rest is solvent; wherein the assistant is ZG-327 dye assistant produced by Shandong Kaya chemical industry Co., Ltd; the resin is modified polyurethane resin XH-PU408 produced by Dongguan Asahi chemical Co., Ltd; the paste is an animal fiber printing paste made of acidic and metal complex dyes produced by Shanghai Shencheng chemical engineering Limited company; the base dye (i.e., a common dye having no photochromic function) may include natural dyes, reactive dyes, acid dyes, disperse dyes, and the like (which may be commercially available or self-formulated).
Wherein the optically variable material adopts
Figure 100002_6
，
Ar1~Ar7Independently selected from H, C6～C30Substituted or unsubstituted aromatic hydrocarbon radical, C6～C30Substituted or unsubstituted fused ring aromatic hydrocarbon group of (A), C6～C30Substituted or unsubstituted fused heterocyclic group, five-membered heterocyclic ring or substituted heterocyclic ring, six-membered heterocyclic ring or substituted heterocyclic ring, triarylamino group, aryl ether group, C1～C12And Ar is any one of a substituted or unsubstituted aliphatic alkyl group of (a), and1~Ar7not H at the same time. And dyeing and finishing the woven fabric or the knitted fabric by the photochromic dye to form a white fabric. The white cloth formed by dyeing and finishing is blue under the irradiation of white light.
Example 2
Example 2 provides a photochromic dye substantially identical to the photochromic dye of example 1, except that the photochromic material used is the same as the photochromic material
Figure 7
，
Ar14And Ar15Independently selected from H, C6～C20Aromatic group of (2), C4～C20And C4～C20Any one of the condensed ring aromatic groups of (A), Ar14And Ar15Not simultaneously being a hydrogen atom or a 4- (2, 2-diphenylvinyl) -substituted phenyl group, R7~R10Independently selected from H, C1～C30Alkyl and C6～C20The white cloth formed by dyeing and finishing the photochromic dye in the embodiment 2 is red under the irradiation of white light.
Example 3
Example 3 provides a photochromic dye substantially identical to the photochromic dye of example 1, except that the photochromic material used is the same as the photochromic material
Figure 8
，
Wherein R is11、R12And R13Is independently selected from any one of substituted phenyl, substituted biphenyl, substituted naphthyl, substituted anthryl, substituted phenanthryl and substituted fluorenyl, and the substituent is independently selected from C1～C18An alkyl group; the white cloth formed by dyeing and finishing the photochromic dye in example 3 is green under white light irradiation.
Example 4
Example 4 provides a photochromic dye substantially identical to the photochromic dye of example 1, except that the photochromic material used is a multicoloured element N, N-bis (2 oxygen adjacent to pyrrole-methyl); the yellow cloth formed by dyeing and finishing the photochromic dye in example 5 is red under white light irradiation.
Example 5
Example 5 provides a photochromic dye substantially identical to the photochromic dye of example 1, except that the photochromic material used is iodide; the blue cloth formed through the photochromic dye dyeing and finishing in example 6 was gradually lightened in color under white light irradiation.
Example 6
Example 6 provides a photochromic dye substantially identical to the photochromic dye of example 1, except that the photochromic material used employs a phthalocyanine-based compound and aluminum particles in a ratio of 2: 5, mixing the materials according to the proportion of the first component and the second component to form a material adopting a complementary color principle; the blue cloth formed by dyeing and finishing the photochromic dye in example 6 shows a color change of magenta under white light irradiation.
Other embodiments of the present invention are not intended to be limited to the above embodiments, and it should be understood that the above embodiments are only illustrative of the technical idea and features of the present invention, and the purpose of the present invention is to enable those skilled in the art to understand the contents of the present invention and implement the present invention, and not to limit the protection scope of the present invention. All equivalent changes and modifications made according to the spirit of the present invention should be covered within the protection scope of the present invention.

Claims (4)

1. The photochromic dye capable of emitting blue light is characterized by comprising a photochromic material, wherein the photochromic material is a blue light emitting material, the blue light emitting material comprises any one or a combination of two or more of erbium, a compound A, a compound B, a compound C, a compound D and a compound E, and the compound A is a compound A
Figure 24644DEST_PATH_IMAGE001
，
Ar 1-Ar 8 in the compound A are independently selected from any one of substituted or unsubstituted aromatic hydrocarbon groups of H, C6-C30, substituted or unsubstituted condensed ring aromatic hydrocarbon groups of C6-C30, substituted or unsubstituted condensed heterocyclic groups of C6-C30, five-membered heterocyclic rings or substituted heterocyclic rings, six-membered heterocyclic rings or substituted heterocyclic rings, triarylamine groups, aryl ether groups and substituted or unsubstituted aliphatic alkyl groups of C1-C12, and Ar 1-Ar 8 are not H at the same time;
the compound B is
Figure 156548DEST_PATH_IMAGE002
，
Ar 1-Ar 8 in the compound B are independently selected from any one of substituted or unsubstituted aromatic hydrocarbon groups of H, C6-C30, substituted or unsubstituted condensed ring aromatic hydrocarbon groups of C6-C30, substituted or unsubstituted condensed heterocyclic groups of C6-C30, five-membered heterocyclic rings or substituted heterocyclic rings, six-membered heterocyclic rings or substituted heterocyclic rings, triarylamine groups, aryl ether groups and substituted or unsubstituted aliphatic alkyl groups of C1-C12, and Ar 1-Ar 8 are not H at the same time;
the compound C
Figure 416628DEST_PATH_IMAGE003
，
Ar 1-Ar 12 in the compound C are independently selected from one of substituted or unsubstituted aromatic hydrocarbon groups of H, C6-C30, substituted or unsubstituted condensed ring aromatic hydrocarbon groups of C6-C30, substituted or unsubstituted condensed heterocyclic groups of C6-C30, five-membered heterocyclic rings or substituted heterocyclic rings, six-membered heterocyclic rings or substituted heterocyclic rings, triarylamine groups, aryl ether groups, and substituted or unsubstituted aliphatic alkyl groups of C1-C12, Ar 1-Ar 8 are not H at the same time, Ar13 is selected from one of substituted or unsubstituted aromatic hydrocarbon groups of C6-C30, substituted or unsubstituted condensed ring aromatic hydrocarbon groups of C6-C30, and substituted or unsubstituted aliphatic alkyl groups of C1-C12;
the compound D is
Figure 777333DEST_PATH_IMAGE004
，
Wherein R1 and R2 in the compound D are independently selected from C1-C20 alkyl and substituted or unsubstituted C6-C50 aromatic hydrocarbon groups, or R1 and R2 are cyclic structures formed by connecting divalent alkylene or arylene of C2-C20, and the A1 structure is
Or
Figure 4
Any one of the above-mentioned (a) and (b),
Figure 374854DEST_PATH_IMAGE006
A2is H,
Figure 3
、
Figure 6
Wherein in A1And A2R in (1)3And R6Independently selected from substituted or unsubstituted aromatic hydrocarbon radicals, A1And A2Wherein represents a substitution position with the parent nucleus, and L1 is selected from substituted or unsubstituted arylene groups of C6 to C50;
the compound E is
Figure 406154DEST_PATH_IMAGE009
。
2. The photochromic dye according to claim 1, further comprising one or a combination of two or more of a basic dye, an auxiliary agent, a resin or a paste.
3. Photochromic fabric, characterized in that, the fabric is formed by dyeing and finishing with photochromic dye which emits blue light as described in any one of claims 1 or 2, the fabric further comprises a UV cut-off layer, the UV cut-off layer covers the surface of the fabric, the UV cut-off layer is a coating formed by coating UV absorbent, the UV absorbent is one or a combination of two or more of salicylic acid esters, benzophenones, benzotriazoles, substituted acrylonitrile and triazines, and the transmittance of the UV cut-off layer to ultraviolet ray with wavelength of 200-.
4. Photochromic clothing, characterized by being made of the photochromic fabric of claim 3.
CN201911131979.5A 2018-07-20 2018-07-20 Photochromic dye emitting blue light Pending CN110820364A (en)

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CN201810801870.7A Withdrawn CN108948786A (en) 2018-07-20 2018-07-20 Photochromic dyes, photochromic cloth and photochromic clothes
CN201911132144.1A Pending CN110846021A (en) 2018-07-20 2018-07-20 Photochromic dye capable of emitting green light
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