CA1054607A - Iminoisoindolinone pigments - Google Patents

Iminoisoindolinone pigments

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Publication number
CA1054607A
CA1054607A CA228844A CA228844A CA1054607A CA 1054607 A CA1054607 A CA 1054607A CA 228844 A CA228844 A CA 228844A CA 228844 A CA228844 A CA 228844A CA 1054607 A CA1054607 A CA 1054607A
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Canada
Prior art keywords
atoms
atom
denote
formula
cyano
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.)
Expired
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CA228844A
Other languages
French (fr)
Inventor
Jost Von Der Crone
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Novartis AG
Original Assignee
Ciba Geigy AG
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Filing date
Publication date
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    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09BORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B57/00Other synthetic dyes of known constitution
    • C09B57/04Isoindoline dyes

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Indole Compounds (AREA)
  • Inks, Pencil-Leads, Or Crayons (AREA)

Abstract

ABSTRACT OF THE DISCLOSURE

Iminoisoindolinone pigments of the formula

Description

The present invention relates to new iminoisoindolin~ne pigments of ~he formula -X2 ~ X2 wherein Xl, X2, X3 and X4 each denote H atoms or halogen atoms~ one of the sub-stituents Xl and X4 representing a halogen atom and not more than one of the -substituents X2 and X3 denoti~ng a halogen atom, with the proviso that X3 must not be a chlorine atom if Xl denotes a H atom; or wherein X2 denotes a cyano or carboxylic acid ester group, and Xl, X3 and X4 all denote H atoms, and Yl ;
and Y2 denote H atoms or chlorine atoms or alkyl or alkoxy groups containing `:
1 - 4 C atoms.
Pigments of particular interest are those of the formula ~I) wherein the substituents Xl - X4 denote H atoms or chlorine atoms, and one of the sub-stituents Xl and X4 represents a chlorine atom a~d not more than one of the sub- ~ -i stituents X2 and X3 denotes a chlo~ine atom, and X3 must not be a chlorine atom if Xl represents a H atom.
Particularl~ preferred p~gments are those of the formula (I) wherein Xl - X4 have the meaning indicated above~ and Yl and Y2 denote H atoms.~-~
The new iminoisoindolinone pigments are obtained if an isoindolinone of the formula Xl ;~
X3 ~ ~ NH (111) X~, O .. :, ', wherein V denotes a group of the formula :~ ' :''' ,. . ,- , . :
.;

1 1054~()7 ~< J4 :, ~ .
: wherein Y4 represents an imino or thio group and Y3 denotes a halogen atom, :
an alkoxy group or a tertiary amino group, is eondensed, in a molar ratio of - ~
2:1, with a diamine of the formula .~ ~-., Yl ' ~ ~ ' "' ' H2N --Y~ NH2 (V) ; 2 : ~:
The starting material is pre~erably an isoindolinone of the formula (III~ wherein the substituents Xl X4 denote H atoms or chlorine atoms, and 'A'` ~' ~''' one of the substituents Xl and X4 represents a chlorine atom and not more than `.
one of the substituents X2 and X3 denotes a halogen atom and X3 denotes a H . -:10 atom if Xl represents a H atom. . ;~
The isoindolinones which are used as the starting .
.~ . : . ~ . ...
,.~ ~ '' ,` ~'.

:,
3~

:
.,., . ~ . :

~ .

,:. ~ , , , , , , , ~ . ..

~ S~ 7 ma-ter.ial, co~ n, :n the 2-posi-tion, an imino or th.io group, 2 halogen atoms, 2 tertiary amino groups, for example piperidino or morpholino groups, or, par-ticularly, 2 alkoxy groups contai~ing 1 - 4 C atoms, preferably methoxy groups.
The isoindolinones therefore preferably correspond to . .
the formula :.. , ~ .
RO OR

1 (VI) ~ ;

. . 4 ~ wherein Xl - X4 have the meaning indicated above and R denotes : an alkyl radical having 1 - 4 C a~toms, preferably a methyl . ~ ;
;., group. "; .
:~ , The 3,3-dialkoxyisoindolinones are obtained by a known process by reacting the corresponding o-cyano-benzoic acid ; `
; alkyl es-ter of ~he formula '' i Xl ' ,, .~ X2~,CN .
3 ~ COOAlky~ (VII) f ~
: ~ :
with an alkali metal alcoholate solution in a lo~er alcohol.
As a rule it is not necessary to isolate the isoindolinone .
thus obtained3 in most cases it can be employed directly for -i the reaction ~ith the diamine The 3-iminoisoindolinones are obtained by a known ~ 4 ~
:1 .
:1 . . . ' process by reacting the corresponding o-cyano-benzoic acid alkyl ester wi~h ammonia.
The o-cyanobenzoic acid esters of the for~ula (VII) ~ .;
are obtained, in turn, from ~he anthranilic acid es~ers of the .~ formula , :.
.-:. v ::

2 ~ N 2 ,,`,, '. ~
; X4 ~`~
by ~he Sandmeyer reaetion, by diazotisation and reaction with ~
potassium cyanide. ~.--~ The following may be mentioned as examples of o-cyano- ~ `~
:;, benzoic acid esters: 6-chloro-2-cyano-benzoic acid methyl ~ ~ 10 ester, 4-chloro-2-cyano-benzoic acid methyl ester, 6-fluoro~
,.3 2-cyano_benzoic acid m~thyl ester, 5-iodo-2-cyano-benzoic ;~ acid methyl estar, 3,4-dichloro-2-cyano-benzoic acid methyl .~ ester, 3,5-dichloro-2 cyano-benzoic acid me~hyl ester, 4,6-dichloro-2-cyano-benzoic acid me~hyl ester, 2,4-dicyano-benzoic acid methyl ester and 2-cyano-terephthalic acid dimethyl ester. . ~:
".,, '~'~
`', ~ ~ , .'.'.' ~ ~ .

"
', `"':"

~ ~5- ~ .

~.~S~7 ::

~ p-Phenyl~nediamine is a particularly preferred diamin~
:~ starting material.
`` ~e following diamines may be mentioned as examples:
1,4-diaminobenzene, 1,3-diaminobenzene, 1,3-diamino-4-mqthyl-: henzene~ 1,3-diamino-4-me~hoxybenzene, 1,3-cliamino-2-methyl-benzene~ 1,3-diamino-2JS-dichlorobenzene, 1,4-diamino-2-chlorobenzene, 1,4-diamino-2-bromobenzene, 1,4-diamino-2,5-dichlorobenzene, 1,4-diamino-2-methylbenzene, 1,4-diamino-2,5-dimethylbenzene~ 1j4-diamino-2-methoxybenzene, 1,4- -~
diamino-2,5-dimethoxybenzene, 1,4-diamino-2-chloro-5-methyl- ~ `
benzene, 1,4-diamino-2-chloro-5-methoxybenzene, 1,4-diamino ~ : ;
"'~", 2-chloro-5-~thoxybenzene~ 1~4-diamino-2~5-diethoxybenzene~
,~ 4,4'-cliamino-diphenyl sulphide, 4,4'-diamino-benzoylanlline, ~ -.
~:i 4,4i-diamino-2-ethoxy-benzoylanilîne, 3,3'-diamino-2,2'- .
; dimethoxy-benzoylaniline, 4,4'-diamino-diphenylurea, 4,4'-~ ", . .
diamino-3,3'-dimethoxy-diphenylurea, 4,4'-diaminostilbene, . 4,4'-diamino-azobenzene, 2-methyl-4,4'-diaminoazobenzene, 2~methoxy-4,4'-diaminoazobenzene, 2,5-dimethyl-4,4'-diamino-azobenzene, 2,5,2'-trimethyl-4,4'-diaminoazobenzene, 3- . ;
:
., 20 methyl-2'-methoxy-4,4'-cliaminoazobenzene, 3-chloro-2'-methyl-., ` .~ ~ .
~:j 4,4'-diaminoa%obenzene, 4-chloro-3,4'-diaminoazobenzene, 2- . ~: ~

"-,: ,;~ , , ~ :

~,:
... ,; ~- ., ,- ., ::: - 6 -37 ~ ~
- . ., ~;~ chloro-4,3'-diaminoazobanzene, 2-methyl-4,3'-diaminoazoben-zene, 2-methoxy-4,3'-diaminoazobenzene, 2,4-diaminoazobenzene, 5-methoxy-2,4-diaminoazobenzene, 2,4-diamino-3',5'-dimethyl-.... . .
~` 4'~acetylaminoazobenzene, 2,4-diamino-5-methoxy-3',5'-di- ~
,~ .
~ chloro-4'-acetyla~inoazobenzene, 4,4'-diamino-phenyl-1-azo- ~
". ~ I
~...... i naphthalene-l', 4,4'-diaminobenzophenone, 4,4'-diaminodi-phenyl ether, 4,4'-diaminodiphenylmethane, 2,Z'-diaminodi- ;
benzyl, 1,4-diaminonaphthalene and 1,5-dia~inonaphthalene. -~
s The condensation takes place in part even in the cold, but if appropriate by warming the intimately mixed reac-~ tants, and particularly advantageously in ~he presence of -~i inert organic solvsnts, that is to say organic solvents which -~`~lj do not take part in the reaction.
~'~'b~ If 3-imino-isoindolin-1-ones, 3-thio-isoindolin-1-onesr or 3,3-bis-~er~.-amino-isoindolin-1-ones or alkali metal sal~s of 3,3-dialkoxyisoindol m l-ones are used as starting ~i ~aterials, it is adva~tageous to use water-miscible org2nic `~ ~ solvents, for example lower aliphatic alcohols, such as lower ~i alkanols, for exampla methanol, isopropanol or butanol, lower " 1 :: . ~ .
~: 20 cyclic ethers, such as dioxane or e~hylene glycol monomethyl ether, or lower aliphatic ketones, such as acetone. The ;l condensation takes placs in this case even at relativelylow temperatures. It is advantageous to carry ouS the reac~ion in ~he presence of base-binding agents; examples of these which should be ~entioned are lower fatty acids, which then simultaneously act as the solvent, particularly acetic acid.

. - 7 - ~ -.

~S~7 If 313-dihalogeno-isoindolin-l-ones are used, organic -~
solvents whioh are free from hydroxyl ~roupsJ such as hydro-carbons, for example aromatic hydrocarbons, such as benzene, toluene, xylene, tetrahydronaphthalene or diphenyl, or cyclo aliphatic hydrocarbons, for example cyclohexane, and also ~-halogena~ed hydrocarbons, such as aliphatic halogenated hydro-carbons, for example carbon ~etrachloride or tetrachloro ~ i ethylene, or aromatic halogenated hydrocarbons, such as ~-chlorobenzene or dichlorobenzenes and trichlorobenzenes, and 0 al50 aromatic nitro-hydrocarbons~ such as nitroben~sne, ethers, in particular aliphatic e~hers, such as dibutyl ether, aroma-~-1 tic ethers, such as diphenyl ether, or cyclic ethers, such as dioxane, and also ketones, such as acetone, or esters, particularly esters of lower fatty acids with lower alkanols, -~
such as ethyl aceta~e, in the presencle of acid-binding agents, ~; ;
are preferred. ~ ~
~ ~ , The new pigment is precipitlated from the reaction medium directly after its formation. It can be used direct, as a raw pigmentJ for csrtain purposes; it is advantageous, 1 20 however, be~ore its application, to condi*ion it by methods ,:i which are in themselves known, for example by extraction with organîc solvents or by grinding with grinding auxiliaries which can aterwards be removed, for example salts or, in ;~ particular, hexachloroethane, or by alkaline reprecipitation. o~
The purity, tinctorial strength and ~ransparency can be ~urther improved in this manner.
The new colorants are valuable pigments whieh can be . ,~ . . .

':'', `~': '~
~: `. , ;~
~:
:. :

'' , .'.. . . . . . . . .... . . .
.. . ..

~q~5~7 .
.. . .
used in a finely divided for~ for pigmenting high-molecular organic material, for exa~ple cellulose ethers and cellulose .: . .
esters, such as ethylcellulose, acetylcellulose or nitro-- cellulose, polyamides, polyurethanes or polyesters, natural resins or synthetic resins, for example aminoplasts, particularly ther~oplastic and ~hermosetting acrylic resins, ~ urea-formaldehyde and melamine-for~aldehyde resins, and also ; alkyd resins, phenoplasts, polycarbonates, polyolefines, such as polystyrene, polyvinyl chloride, polyethylene, poly-,,, :
~ 10 propylene, polyacrylonitrile and polyacrylic acid ssters, ,. ~
rubber, cas~in, silicone and silicone resins, individually or as mixtures. It is immaterial here whether ~he high-mole-~ ...... , cular compo~nds ~entioned are present as plastic compositions or as melts or in the form of spinning solutions, lacquers, paints or printing inks. Depending Olt the end use, it `
proves advantageous to use the new pil~ents as toners or in ., the fornt of preparations. The new pi~tents are distinguished ~ ir `i by their high level of fastness, and particularly by out-,-~ standing ~astness to light, migration and wea~hering. The ;^~
iminoisoindolinones derived fro~ p-phenyl~nediamin~ are distinguished by valuable medium yellow shades which have ~1~ hitherto only been obtained with iminoisoindolinones formed from complicated diamines.
,.~ .::
Example 1 5.1 g of 6-chloro-2-cyanobenzoic acid methyl ester are ~ introduced into a solution of 1.35 g of sodiu~ methylate in ; 40 ml of methanol. The mixture is stirred for 30 minutes at , :, :

. - ' ', '' ' ' ', .. ' ~ ,: , '. : ' ~
. .

:; `
~05~
room temperatuJ~e~ a clear solution ~eing formed. 1.35 g of p-phenylenediamine are now added and the mixture is stirred ^ for a further 15 hours a-t room temperature. The yellow sodium salt of the colorant separa-tes ou-t. The mixture is diluted with 100 m] ol o-dichlorobenzene and acidified ~ri-th 5 ml of glacial ace-tic acid. The reaction mixture is now - warmed to 150C, whilst stirring well and distilling o~f the ` methanol. The temperature i5 kept at 150Gfor 2 hours; the ;~ mixture is -then allowed to cool to 100Cand is filtered.
, The moist pigment is washed well with methanol, acetone and water and is dried at 100C in a vacuum oven. This gives ,'` 1, .
4.8 g of a yellow pigment which corresponds to the formula The pigment can be employed for colouring lacquers ~ ;
and plastics, direct or in a comminuted form, for example `~
after grinding with a grinding auxiliary which can afterwards . .
-s~ be removed, such as, for example, sodium ch]oride. Fairly `~
deep colourings in pure, yellow colour shades which are `
distinguished by good fastness to light and migra-tion 7 are ,~ achieved in this way. ;
;~ 6-Chloro-2-cyanobenzoic acid me-thyl ester can be pre-pared, for example, from 6-chloroanthranilic acid methyl ester by the Sandmeyer reactio-n by diazotisation and reaction with ~; - 10 ~
. ~ . , , :

:. :..... .. , . ,,: ~. - . :: . . ,, ; , . ., . ~ : . .

`
~l:)S~6 po-tassi~lm cya1~i.,^J.e. A.~-ter recrys-talllsation ~rom isopropano]., the pure compoulld has a melting poin-t oI 76-77C.
~ les 2 - 9 ., The Table which follows lis-ts fur-ther pigmen-ts of the '` formula : .
, X~X2 ~ ~i ,, x~, o 1~ X4, wherein the substituents Xl - X4 have the meaning indicated in the columns~ which are obtained if 2 mols of the o-cyano-:1 benzoic acid ester listed in column II are condensed, in ,,~ accordance with the instructions of Example 1, wi-th 1 mol o~
; p-phenylenediamine. Column III glves the melting point o~
the o--cyanobenzolc acid ester used and column VIII gi~2S t'ne shade of P~ contalning 0.2% of the resulting pigment.
.,,.'1 '~,` ~
~3 3 ~
~: ". ~ .

. 3~ ~ :

:s~ '~

'", ~' .:
~i . .j,, 1~5~
q~blc~

Ex. o cyanobenzoic meltine Xl X2 X X4 Shads . aci.d es-ter point 3 _ ~____.~ _.__ _ ~ ~
2 4-chloro-2-cyanobenzoic -117~18C HCl HH medi.um :.~ acid methyl es-ter yellol,r ~ ~ 2-cyano-tereph-thalic 115-16C H o~3 H H .
.~ acid dimethyl ester :~: 4 294-dicyanobenzoic acid 168-6~C H CN H H n :' . methyl ester I 5 5-iodo-2-cyanobenzoic 107-08C H H I H . "
acid methyI es-ter .
~ 6 6-fluoro-2-cyanobenzoic 74-75C H H H F n :~
:. acid methyl ester .
:.~ 7 4,6~dichloro-2-cyano- 70-71C H Cl H Cl ~j benzoic acid methyl .
ester ^.-:
8 3,5-dichloro-2-cyano- 102-03C Cl H Cl H ll . .
~enzoic acid methyl ., es-ter .~., 9 3,4-dichloro 2-cyano- 120C Cl Cl H H n .

.' /, ' __ ,, ..... . _ _ _ _ _ . _ .~ As indicatèd in Example 1, the cyanobenzoi.c acid ~.~ methyl esters used can be obtained from the corresponding '~ . anthranilic acid methyl esters.
' Fxamples l _ 8 `;, Pigments having similarly good propertieis are obtained ;
.
-t~ if the cyanobenzoic acid esters listed in column II of the -table below are condensed with the diamine indicated in .
.~ column III, in accordance wi-th the instructions of Example 1, ;', in a molar ratio of 2:1. Column IV gi~es the colour shade of :.-i - 1.2 _ :
,, :`?
", ~ :

~ ~ ~0~ 7 a PVC sheet ~rhich c~ntainc3 0.2~ o~ the colorant.
Table II
, :~
: ~ ~x.
11 3,5-dichloro-2-cyano- 1,5~naphthylene- orange benzoic acid methyl diamine eister . - :., . ~
.~ 12 " 2,5~dime~thyl-1,4- yellowish~
phenylenediamine tinged :~
orange 13 ~1 2-methyl-5-chloro-.~ . 1,4-phenylenediamine yell.ow ~ 14 3,4-dichloro-2-cyano- " yellow :- benzoic acid methyl : ester .`~ 15 " 1,5-naphthylene- orange `.-:; diamine . ~ .
. 16 2~cyano-tereph-thalic " orange `ij acid dime-thyl ester 17 2,5-dimethyl~1,4- yellow .. phenylenediamine ~:
~:' 18 " 2-chloro-5-methyl yellow : 1,4--phenylenediamine .~
~ 19 6-chloro~2~cyano- 2_ehloro-5 methoxy- yellow :::
.. :.¦ ben~.oic acid methyl 1,4--phenylenediamine .::~
:3 ester .:
. .,:1 ~, ;.~':: 20 6-chloro-2-cyano- 2,5-diethoxy~1,4- reddish- ~
I-i benzoie aeid methyl phenylenediamine tinged : :
.~ ester yellow --~ 21 ~,4-dichloro-2-cyano- 2,5-dichloro-174 yellow benzoie acid methyl phenylenediamine :` ester . . -~
. :~. .. ..

65 parts of stabilised polyvinyl chloride, 35 parts ,:, of dioctyl phthalate and 0.2 part of the colorant obtained . in aeeordanee with Example 1 are stirred together and the ::

~,.".,, , ~ ::

,.......................................................................... .

, :
;, ' ' :' ' ' , .' :' :'..... ' ~ ' . ' . . . : : .: .: ' . ': -, ~S46~7 mixture i..5 th~ orl;ed on a twin-roll calender ~or 7 minutes at 140C. This gives a yellow~coloured sheet with very good fastness to ligh-t and migra-tion.
Exa~lple 23 10 g of ti-taniu~ dio~ide and 2 g of the pigment prepared in accordance wi-th ~xample 1 are ground in a ball mill for 48 hours together wi-th 88 g of a mixture of 26.4 g of coconut alkyd resin, 24.0 g of melamine--formaldehyde resin ~
(50% solids con-tent), 8.8 g of ethylene glycol monomethyl ~ ~;
ether and 28.8 g o:~ xylene.
, ~ , I~ this lacquer is sprayed onto an aluminium foi], pre-dried ~or ~0 minutes at room ternperature and then stoved ;1 for 30 minutes at 120C, a yellow lacquering is ob-tained which - ~
~ is distinguished by a good depth of colour and very good fast~ ``
;, ness to overlacquering, ligh-t and weathering. ~ ~

~ , :`. 1 ` , ;. ~., ~ -: ................................ . . . .
.`,' j ~; ,:~
. ~.~ , ..
l,fj , , ,. l ~

i ~ : ` ~ ; :: : :: : ~ . . ` . ::: , . .. , . . .

Claims (8)

THE EMBODIMENTS OF THE INVENTION IN WHICH AN EXCLUSIVE
PROPERTY OR PRIVILEGE IS CLAIMED ARE DEFINED AS FOLLOWS:
1. Iminoisoindolinone pigments of the formula (I) wherein X1, X2, X3 and X4 each denote H atoms or halogen atoms, one of the sub-stituents X1 and X4 representing a halogen atom and not more than one of the substituents X2 and X3 denoting a halogen atom, with the proviso that X3 must not be a chlorine atom if X1 denotes a H atom; or wherein X2 denotes a cyano or carboxylic acid ester group, and X1, X3 and X4 all denote H atoms, and Y1 and Y2 denote H atoms or chlorine atoms or alkyl or alkoxy groups containing 1 - 4 C atoms.
2. Iminoisoindolinone pigments according to claim 1, wherein the sub-stituents X1 - X4 denote H atoms or chlorine atoms, and one of the substituents X1 and X4 represents a chlorine atom and not more than one of the substituents X2 and X3 denotes a chlorine atom and X3 denotes a H atom, if X1 represents a H atom.
3. Iminoisoindolinone pigment according to claim 1 or 2, wherein Y1 and Y2 denote H atoms.
4. A pigment of the formula .
5. A pigment of the formula
6. A pigment of the formula
7. A pigment of the formula
8. A pigment of the formula
CA228844A 1974-06-11 1975-06-09 Iminoisoindolinone pigments Expired CA1054607A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH795574A CH589128A5 (en) 1974-06-11 1974-06-11

Publications (1)

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CA1054607A true CA1054607A (en) 1979-05-15

Family

ID=4332929

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Country Status (7)

Country Link
JP (1) JPS598304B2 (en)
CA (1) CA1054607A (en)
CH (1) CH589128A5 (en)
DE (1) DE2525587A1 (en)
FR (1) FR2274662A1 (en)
GB (1) GB1503961A (en)
IT (1) IT1038863B (en)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS55152749A (en) * 1979-05-16 1980-11-28 Asahi Chem Ind Co Ltd Novel organic compound and preparation thereof
US4327024A (en) * 1979-11-20 1982-04-27 Ciba-Geigy Corporation Iminoisoindolinone pigments, process for their production and use thereof
CN114196227B (en) * 2021-12-29 2022-09-30 百合花集团股份有限公司 Process for the preparation of isoindolinone pigments
CN114573998B (en) * 2022-01-28 2024-03-05 山东世纪连泓新材料有限公司 Pigment yellow 139 synthesis process

Also Published As

Publication number Publication date
DE2525587A1 (en) 1975-12-18
CH589128A5 (en) 1977-06-30
JPS518319A (en) 1976-01-23
JPS598304B2 (en) 1984-02-23
FR2274662B1 (en) 1977-07-08
IT1038863B (en) 1979-11-30
GB1503961A (en) 1978-03-15
FR2274662A1 (en) 1976-01-09

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