CN101955689B - Pigment composition of triarylmethane and rhodamine, and pigment dispersion using same - Google Patents
Pigment composition of triarylmethane and rhodamine, and pigment dispersion using same Download PDFInfo
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- CN101955689B CN101955689B CN201010233507.3A CN201010233507A CN101955689B CN 101955689 B CN101955689 B CN 101955689B CN 201010233507 A CN201010233507 A CN 201010233507A CN 101955689 B CN101955689 B CN 101955689B
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B35/00—Disazo and polyazo dyes of the type A<-D->B prepared by diazotising and coupling
- C09B35/02—Disazo dyes
- C09B35/039—Disazo dyes characterised by the tetrazo component
- C09B35/205—Disazo dyes characterised by the tetrazo component the tetrazo component being a derivative of a diaryl- or triaryl- alkane or-alkene
- C09B35/21—Disazo dyes characterised by the tetrazo component the tetrazo component being a derivative of a diaryl- or triaryl- alkane or-alkene of diarylmethane or triarylmethane
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B11/00—Diaryl- or thriarylmethane dyes
- C09B11/28—Pyronines ; Xanthon, thioxanthon, selenoxanthan, telluroxanthon dyes
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B63/00—Lakes
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/006—Preparation of organic pigments
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pigments, Carbon Blacks, Or Wood Stains (AREA)
- Optical Filters (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
Abstract
The invention aims at providing a lake pigment which exhibits excellent light resistance and heat resistance and has a triarylmethane structure and/or a rhodamine structure, and a pigment dispersion using the lake pigment. Therefore, the invention provides a pigment composition, which is characterized in that an untreated pigment of the lake pigment with the triarylmethane structure and/or the rhodamine structure is treated by an organic acid selected from substituted or unsubstituted aryl sulfonic acid and substituted or unsubstituted aryl carboxylic acid.
Description
Technical field
The present invention relates to triarylmethane class and rhodamine class color compositions, specifically, the present invention relates to the triarylmethane class of photostabilization and excellent heat resistance and rhodamine class color compositions and employ the pigment dispersion of these color compositions.
Background technology
All the time, triarylmethane class dye well pigment obtains application (patent documentation 1 ~ 4) in fields such as toning agent, spray printing ink, colour filters.
But compared with phthalocyanine pigment etc., there is the defect of thermotolerance, photostabilization difference in triarylmethane class dye well pigment.For this reason, existing about the trial overcoming this defect.Such as, the colour filter (patent documentation 5) developing the polymkeric substance used containing triphenhlmethane dye has been attempted.In addition, have also been attempted use triarylmethane and organic acid salt etc. (patent documentation 6).
Prior art document:
Patent documentation 1: Japanese Laid-Open Patent Publication 61-006659 publication
Patent documentation 2: Japanese Laid-Open Patent Publication 61-036758 publication
Patent documentation 3: No. 2002/100959th, International Publication
Patent documentation 4: Japanese Unexamined Patent Publication 11-223720 publication
Patent documentation 5: Japanese Unexamined Patent Publication 2000-162429 publication
Patent documentation 6: Japanese Unexamined Patent Publication 2006-306933 publication
Summary of the invention
The problem that invention will solve
But practical situation are that the photostabilization of the triarylmethane class pigment of above-mentioned acquisition and thermotolerance are still not enough, and its manufacturing process is also comparatively complicated, and the method that there is no at present realizes practical.
Based on this, the triarylmethane class color compositions that the object of the present invention is to provide photostabilization and excellent heat resistance and the rhodamine class color compositions using the pigment dispersion of this color compositions and photostabilization and excellent heat resistance and use the pigment dispersion of this color compositions.
The method of dealing with problems
The present invention is based on following discovery and complete: there is the sulfonic acid of aryl or carboxylic acid by utilizing the pigment lake with triarylmethane structure and the pigment lake with rhodamine structure are processed, the photostabilization of pigment and thermotolerance can be made to be largely increased.
Namely, the feature of color compositions of the present invention is, utilize and be selected from the organic acid of substituted or unsubstituted aryl sulfonic acid and substituted or unsubstituted aryl carboxylic acid or the following untreated pigment of its salt pair processes, described untreated pigment is selected from the pigment lake with triarylmethane structure that chemical formula 1 represents and/or the rhodamine structure that chemical formula 3 represents.
[chemical formula 1]
In chemical formula 1, R
1, R
2, R
3, R
4represent-H ,-CH independently of one another
3,-C
2h
5,-Ph (phenyl) ,-PhCH
3,-CH
2ph (SO
31/2Ba) or-CH
2ph (SO
31/3Al), R is the substituted or unsubstituted phenyl or naphthyl shown in chemical formula 2,
[chemical formula 2]
In chemical formula 2, R
5representative-H ,-NHCH
3,-N (CH
3)
2,-N (C
2h
5)
2,-NHPh or-NHPh (CH
3) (SO
3h) or its salt, R
6representative-H ,-Cl or-SO
3h or its salt, R
7for-NHC
2h
5,
[chemical formula 3]
In chemical formula 3, R
8, R
9, R
10, R
11represent-H or alkyl independently of one another, R
12for-H, alkyl or substituted or unsubstituted phenyl.
Pigment dispersion of the present invention is the pigment dispersion obtained by using above-mentioned color compositions to carry out dispersion treatment.
In addition, pigment dispersion of the present invention can also by carrying out dispersion treatment to being selected from the untreated pigment of pigment lake with triarylmethane structure that chemical formula 1 represents and/or the rhodamine structure that chemical formula 3 represents and obtaining under existing at the organic acid being selected from substituted or unsubstituted aryl sulfonic acid and substituted or unsubstituted aryl carboxylic acid.
The effect of invention
By utilizing aryl sulfonic acid or aryl carboxylic acid, triarylmethane class of the present invention and rhodamine class color compositions are processed, some change of state is there is to make pigment particles surface, re-use this color compositions and prepare pigment dispersion, when utilizing this dispersion to carry out production example as colour filter, the film of photostabilization and excellent heat resistance can be obtained.
Embodiment
The triarylmethane class pigment used in the present invention is the pigment lake of the ion with the chemical structural formula shown in above-mentioned formula 1, specifically, C.I. pigment blue 1 can be enumerated, C.I. pigment blue 1: 2, C.I. Pigment blue 9, C.I. pigment blue 14, C.I. Pigment blue 24, C.I. pigment violet 3, C.I. pigment violet 3: 1, C.I. pigment violet 3: 3, C.I. pigment violet 27, C.I. pigment violet 39, C.I. Pigment blue 78, C.I. Pigment green 1, C.I. Pigment green 2, C.I. Pigment green 4, C.I. Pigment blue 56, C.I. Pigment blue 56:1, C.I. pigment Blue-61, C.I. pigment Blue-61: 1, C.I. pigment lake such as Pigment blue 62 grade.
In addition, the rhodamine class pigment used in the present invention is the pigment lake of the ion with the chemical mechanical formula shown in above-mentioned chemical formula 3, specifically, pigment violet 1, pigment violet 1 can be enumerated: 1, pigment violet 2, pigment violet 2:2, pigment violet 81, pigment red 81: 1, pigment red 81: 2, pigment red 81: 3, pigment red 81: 4, the pigment lake such as Pigment red 169, Pigment red 173.
As the color lake agent in triarylmethane class pigment and/or rhodamine class pigment, phospho-wolframic acid, phospho-molybdic acid, phosphotungstomolybdic acid, copper ferrocyanide, silicomolybdic acid, aluminium can be enumerated.
In the present invention, being used for the organic acid that triarylmethane class pigment and/or rhodamine class pigment process is substituted or unsubstituted aryl sulfonic acid and/or substituted or unsubstituted aryl carboxylic acid.Wherein, described substituted or unsubstituted aryl sulfonic acid refers to, containing having substituting group or not having the sulfonic acid of substituent aryl; Described substituted or unsubstituted aryl carboxylic acid refers to, containing having substituting group or not having the carboxylic acid of substituent aryl.Alternatively or unsubstituted aryl sulfonic acid, can enumerate the alkyl benzene sulphonate (ABS)s such as Phenylsulfonic acid, naphthene sulfonic acid, toluene sulfonic acide, acid dimethyl, alkyl naphthalene sulfonic acid, dialkyl napthalene sulfonic acids etc., in addition, also can be the aryl sulfonic acid containing heterocycle such as pyridine-sulfonic acid.In addition, above-mentioned aryl sulfonic acid also all can by amino, hydroxyl replaces, and can also be the salt of sodium, calcium, potassium etc.As the concrete example of these acid, the 2-sodium naphthalene sulfonate shown in chemical formula 4,2-naphthene sulfonic acid hydrate, 3-(2H-benzotriazole-2-base)-5-sec-butyl-4-DHBS, sodium p styrene sulfonate, 3-methyl isophthalic acid-(4-sulfophenyl)-5-pyrazolone etc. can be enumerated.Alternatively or unsubstituted aryl carboxylic acid, can be phenylformic acid, phthalic acid, trimellitic acid, naphthoic acid, the naphthalene-2 shown in chemical formula 4, the naphthalic acids such as 3-dioctyl phthalate), in addition, the salt of the carboxylic acid that can also be tolyl acid, mesitylenic acid, Whitfield's ointment (hydroxy-benzoic acid), phthalonic acid (2-(carboxycarbonyl) phenylformic acid), hydroxynaphthoic acid etc. are substituted and the sodium, calcium, potassium etc. of above-mentioned carboxylic acid.
[chemical formula 4]
Utilize in the present invention " process " that aryl sulfonic acid and/or aryl carboxylic acid carry out, be included in the process of the above-mentioned acid of surface application of above-mentioned untreated pigment, typically " process " refer to, above-mentioned untreated pigment is put in the solution of aryl sulfonic acid and/or aryl carboxylic acid, stir the fixed time under assigned temperature after, filter pigment to implement to be separated.In sulfonic acid at this moment and/or the solution of carboxylic acid, be preferably added with the acid such as acetic acid, citric acid, formic acid, oxalic acid in advance.By adding these acid, the cationic moiety of surface of pigments can be made to activate, thus promote the absorption of sulfonic acid, be improved to make pigment-dispersing.Preferred concentration when adding acetic acid is more than 0.5 quality % and does not make the scope of pigment dissolved.In addition, the temperature range of above-mentioned process is preferably 60 ~ 100 DEG C.
Dispersion of the present invention makes following color compositions disperse the dispersion obtained in a solvent, and described color compositions carries out processing the rear color compositions obtained to triarylmethane class pigment and/or rhodamine class pigment with aryl sulfonic acid and/or aryl carboxylic acid.As dispersing method, the method such as using coating modulator (paint conditioner), sand mill, apex mill, dispersion machine (dispermat) can be enumerated.
In addition, in the present invention, the process utilizing aryl sulfonic acid and/or aryl carboxylic acid can also be carried out while dispersion triarylmethane class pigment and/or rhodamine class pigment.Now, relative to the untreated pigment of 100 mass parts, the addition of aryl sulfonic acid and/or aryl carboxylic acid is 1 ~ 20 mass parts, preferably 5 ~ 20 mass parts.Concrete dispersing method is identical with the dispersing method of above-mentioned color compositions.
When preparing color compositions of the present invention and pigment dispersion, tensio-active agent can also be added wherein.By adding tensio-active agent, SURFACTANT ADSORPTION can be made in surface of pigments thus the dispersiveness of raising pigment.As the tensio-active agent that can use in the present invention, the sulphonic acids such as naphthalene sulfonic acidformaldehyde condensation product, lignin sulfonic acid tensio-active agent can be enumerated.
As the solvent that can use in pigment dispersion of the present invention, as long as the conventional solvent used can be not particularly limited, but because the photostabilization of known pigment is better than dyestuff usually, thus do not make the solvent of pigment dissolved from the viewpoint of thermotolerance, the preferred use of photostabilization.
embodiment
Below, the present invention will be described in conjunction with specific embodiments, but the present invention is not limited to following record.It is pointed out that when not having specified otherwise, described " part " and " % " in this specification sheets represents " mass parts ", " quality % " respectively.
(embodiment 1)
As shown in table 1, in 2.5% acetic acid aqueous solution 250 parts, add 10 parts of untreated C.I. pigment blue 1s and 1 part of 2-sodium naphthalene sulfonate, after utilizing dispersion machine fully to stir, be warming up to 80 DEG C and stir 2 hours.Filter gained slurry, after washing precipitation, in 80 DEG C of dried overnight, thus obtain the color compositions 9.9 parts of target.
By this color compositions 5 parts, propylene glycol methyl ether acetate 36.7 parts and high score subclass dispersion agent (BYK 170, BYK Chemie Japan company manufactures) 8.3 parts of zirconium oxide beads together with φ 0.5mm add in paint (lacquer) bottle, after disperseing 1 hour with coating modulator, add acrylic resin (SPC-2000, Showa polymer (strain)) 0.2 part, obtain blue pigment dispersion.
(embodiment 2 ~ 11)
Use each composition shown in table 1, obtain the blue pigment dispersion of embodiment 2 ~ 11 according to the method identical with embodiment 1.It is pointed out that in embodiment 9 and 10, tensio-active agent is added in acetic acid aqueous solution together with C.I. pigment blue 1 and 2-sodium naphthalene sulfonate 1 part.
(comparative example 1 ~ 2)
Untreated pigment shown in direct use table 1, and by propylene glycol methyl ether acetate 36.7 parts and high score subclass dispersion agent (BYK 170, BYK Chemie Japan company manufactures) 8.3 parts of zirconium oxide beads together with φ 0.5mm add in paint bottle, after disperseing 1 hour with coating modulator, add acrylic resin (SPC-2000, Showa polymer (strain)) 0.2 part, obtain blue pigment dispersion.
(evaluation)
[the test making of glass coated plate]
Utilize spinner to be coated on by pigment dispersion on the square square glass plate of 10cm, make test glass coated plate thus.
[evaluation of thermotolerance]
Glass coated plate is statically placed in be warming up to 200 DEG C air bath (air bath) in, keep 1 hour.Colorimeter (CM3700D, KONIKA MINOLTA manufactures) is utilized to measure the aberration (Δ Eab) dropping into glass coated plate before and after air bath.They put in air bath using the coated plate of the dispersion of comparative example 1 and 2 as standard test specimen, during with its aberration (1.00) for standard, the aberration of each glass coated plate is as shown in table 1 relative to the ratio of this standard aberration simultaneously.
[sunproof evaluation]
Use light fastness test machine (XL75 type low temperature xenon arc lamp Ageing machine, Suga Test), under the xenon lamp of 180W, expose 24 hours.Colorimeter (CM3700D, KONIKA MINOLTA manufactures) is utilized to measure the aberration (Δ Eab) exposing front and back glass coated plate.They put in air bath as standard test specimen by the coated plate of the dispersion enumerated in comparative example 1 and 2 simultaneously, and during with its aberration (1.00) for standard, the aberration of each glass coated plate is as shown in table 1 relative to the ratio of this standard aberration.
[evaluation result]
In thermotolerance and sunproof test subject, the ratio of the aberration (Δ Eab) of the test glass coated plate using the dispersion of embodiment 1 ~ 11 to make all is less than 1, visible, carry out compared with each comparative example of processing with not utilizing organic acid, the coated plate of embodiment 1 ~ 11 has excellent thermotolerance and photostabilization.
(embodiment 12 ~ 13)
As shown in table 2, by 4.65 parts of untreated C.I. pigment blue 1s, 0.35 part of 2-sodium naphthalene sulfonate, 36.7 parts of propylene glycol methyl ether acetates, 8.3 parts of high score subclass dispersion agent (BYK 170, BYK Chemie Japan company manufactures) and the zirconium oxide bead of φ 0.5mm add in paint bottle, after disperseing 1 hour with coating modulator, add acrylic resin (SPC-2000, Showa polymer (strain)) 0.2 part, obtain blue pigment dispersion.
(comparative example 3 ~ 4)
As shown in table 2, except employing untreated pigment, not using except organic acid, obtain blue pigment dispersion according to the method identical with embodiment 12 ~ 13.
(comparative example 5)
Stirring and dissolving 5.0g Blue 7 in 250g water, has prepared the aqueous solution of Blue 7.In addition, in 200 DEG C of stirring and dissolving 2.5g sodium naphthalene sulfonates in 200g water, the naphthene sulfonic acid aqueous solution has been prepared.Under stirring in 50 DEG C, the above-mentioned naphthene sulfonic acid aqueous solution is slowly added in the aqueous solution of above-mentioned Blue 7, continues stirring 2 hours, precipitate is filtered, dry, pulverize, thus obtain color compositions.
[table 2]
* 1), * 2) ... identical with table 1
(evaluation)
Make test glass coated plate according to method same as described above, and utilize method same as described above to carry out thermotolerance and light fastness test.Its result is as shown in table 2.
[evaluation result]
In thermotolerance and sunproof test subject, the ratio of the aberration (Δ Eab) of the test glass coated plate using the dispersion of embodiment 12 ~ 13 to make all is less than 1, visible, carry out compared with each comparative example of processing with not utilizing organic acid, the coated plate of embodiment 12 ~ 13 has excellent thermotolerance and photostabilization.
industrial applicibility
When using triarylmethane class of the present invention and rhodamine class pigment and employ the dispersion of these pigment, can obtain and there is excellent heat resistance and sunproof film, therefore, not only can use it for the fields such as colour filter such as liquid crystal indicator, colour filter, OLED display, can also apply at toning agent, spray printing ink area.
Claims (5)
1. a color compositions, it is characterized in that, utilize the organic acid being selected from compound shown in chemical formula 4 to process following untreated pigment, described untreated pigment is selected from the pigment lake of the rhodamine structure of triarylmethane structure and/or chemical formula 3 expression with chemical formula 1 expression
[chemical formula 1]
In chemical formula 1, R
1, R
2, R
3, R
4represent-H ,-CH independently of one another
3,-C
2h
5,-Ph ,-PhCH
3,-CH
2ph (SO
31/2Ba) or-CH
2ph (SO
31/3Al), R is the substituted or unsubstituted phenyl or naphthyl shown in chemical formula 2,
[chemical formula 2]
In chemical formula 2, R
5representative-H ,-NHCH
3,-N (CH
3)
2,-N (C
2h
5)
2,-NHPh or-NHPh (CH
3) (SO
3h) or its salt, R
6representative-H ,-Cl or-SO
3h or its salt, R
7for-NHC
2h
5,
[chemical formula 3]
In chemical formula 3, R
8, R
9, R
10, R
11represent-H or alkyl independently of one another, R
12for-H, alkyl or substituted or unsubstituted phenyl,
[chemical formula 4]
2. color compositions according to claim 1, wherein also containing tensio-active agent.
3. a pigment dispersion, which uses the color compositions described in claim 1 or 2.
4. a pigment dispersion, it is the pigment dispersion carrying out dispersion treatment to following untreated pigment and obtain under the organic acid being selected from compound shown in chemical formula 4 exists, described untreated pigment is selected from the pigment lake of the rhodamine structure of triarylmethane structure and/or chemical formula 3 expression with chemical formula 1 expression
[chemical formula 1]
In chemical formula 1, R
1, R
2, R
3, R
4represent-H ,-CH independently of one another
3,-C
2h
5,-Ph ,-PhCH
3,-CH
2ph (SO
31/2Ba) or-CH
2ph (SO
31/3Al), R is the substituted or unsubstituted phenyl or naphthyl shown in chemical formula 2,
[chemical formula 2]
In chemical formula 2, R
5representative-H ,-NHCH
3,-N (CH
3)
2,-N (C
2h
5)
2,-NHPh or-NHPh (CH
3) (SO
3h) or its salt, R
6representative-H ,-Cl or-SO
3h or its salt, R
7for-NHC
2h
5,
[chemical formula 3]
In chemical formula 3, R
8, R
9, R
10, R
11represent-H or alkyl independently of one another, R
12for-H, alkyl or substituted or unsubstituted phenyl,
[chemical formula 4]
5. pigment dispersion according to claim 4, wherein, described dispersion treatment is carried out under described organic acid and tensio-active agent exist.
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JP5493576B2 (en) * | 2009-08-11 | 2014-05-14 | 東洋インキScホールディングス株式会社 | Coloring composition for color filter, color filter and color display device |
JP5776192B2 (en) | 2010-02-16 | 2015-09-09 | 株式会社リコー | Field effect transistor, display element, image display apparatus and system |
KR101467995B1 (en) * | 2012-12-03 | 2014-12-02 | (주)경인양행 | Triarylmethane dye polymer compound, colored resin composition comprising the same for color filter and color filter using the same |
KR102231572B1 (en) * | 2013-06-17 | 2021-03-24 | 토요잉크Sc홀딩스주식회사 | Coloring composition for color filter and color filter |
TWI644174B (en) * | 2013-07-16 | 2018-12-11 | 南韓商東友精細化工有限公司 | Colored curable resin composition |
TWI624499B (en) * | 2013-07-16 | 2018-05-21 | 東友精細化工有限公司 | Coloring curable resin composition |
JP6534523B2 (en) * | 2014-08-12 | 2019-06-26 | 株式会社Dnpファインケミカル | Colored resin composition for color filter, color filter, and display device |
JP7064411B2 (en) * | 2018-09-19 | 2022-05-10 | 東友ファインケム株式会社 | Colored resin compositions, color filters, and display devices |
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TWI472581B (en) | 2015-02-11 |
KR101730511B1 (en) | 2017-04-26 |
JP5481647B2 (en) | 2014-04-23 |
CN101955689A (en) | 2011-01-26 |
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