GB1569837A - Phthalocyanine pigments - Google Patents
Phthalocyanine pigments Download PDFInfo
- Publication number
- GB1569837A GB1569837A GB3698177A GB3698177A GB1569837A GB 1569837 A GB1569837 A GB 1569837A GB 3698177 A GB3698177 A GB 3698177A GB 3698177 A GB3698177 A GB 3698177A GB 1569837 A GB1569837 A GB 1569837A
- Authority
- GB
- United Kingdom
- Prior art keywords
- pigment
- phthalocyanine
- mixture
- adduct
- weight
- 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
Links
Classifications
-
- 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
- C09B68/00—Organic pigments surface-modified by grafting, e.g. by establishing covalent or complex bonds, in order to improve the pigment properties, e.g. dispersibility or rheology
- C09B68/40—Organic pigments surface-modified by grafting, e.g. by establishing covalent or complex bonds, in order to improve the pigment properties, e.g. dispersibility or rheology characterised by the chemical nature of the attached groups
- C09B68/44—Non-ionic groups, e.g. halogen, OH or SH
- C09B68/441—Sulfonic acid derivatives, e.g. sulfonic acid amides or sulfonic acid esters
-
- 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
- C09B67/0032—Treatment of phthalocyanine pigments
-
- 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
- C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
- C09B67/0034—Mixtures of two or more pigments or dyes of the same type
- C09B67/0035—Mixtures of phthalocyanines
-
- 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
- C09B68/00—Organic pigments surface-modified by grafting, e.g. by establishing covalent or complex bonds, in order to improve the pigment properties, e.g. dispersibility or rheology
- C09B68/40—Organic pigments surface-modified by grafting, e.g. by establishing covalent or complex bonds, in order to improve the pigment properties, e.g. dispersibility or rheology characterised by the chemical nature of the attached groups
- C09B68/44—Non-ionic groups, e.g. halogen, OH or SH
- C09B68/446—Amines or polyamines, e.g. aminopropyl, 1,3,4,-triamino-pentyl or polyethylene imine
-
- 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
- C09B69/00—Dyes not provided for by a single group of this subclass
- C09B69/02—Dyestuff salts, e.g. salts of acid dyes with basic dyes
- C09B69/04—Dyestuff salts, e.g. salts of acid dyes with basic dyes of anionic dyes with nitrogen containing compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
Description
(54) IMPROVEMENTS IN AND RELATING TO
PHTHALOCYANINE PIGMENTS
(71) We, AZIENDE COLORI
NAZIONALI AFFINI ACNA S.P.A., of
Largo Donegani 1/2, 20121 Milano, Italy, an
Italian Company, do hereby declare the invention, for which we pray that a patent may be granted to us, and the method by which it is to be performed, to be particularly described in and by the following statement This invention relates to phthalocyanine pigment compositions which exhibit improved characteristics of gloss, transparency and/or fluidity when they are used in solvent inks. The invention also relates to new pigment additives which may be used in preparing the compositions, and to methods of producing the compositions and the additives.
High efficiency organic pigments are often used in fields of application requiring particular properties of gloss and transparency of the pigmented film, these requirements being particularly manifest in the field of the flexographic inks on nitrocellulose and nitrosynthetic bases.
Further, for inter alia economic reasons, the incorporation of the pigment into the vehicle is desirably effected at a high concentration, as far as is consistent with the rheological requirements of the ink obtained. Therefore, pigments which can be used at high concentrations to give fluid inks are particularly useful.
The present invention permits just these important characteristics of the phthalocyanine pigments to be generally improved. The phthalocyanine may be in the alpha or beta form.
It has already been proposed to use amines of certain types in pigment compositions based on sulphonic derivatives of phthalocyanine (U.S. patent
No. 2,187,816; British patents Nos.
1,376,247 and 1,170,895), but we have surprisingly found that it is possible to achieve a considerable improvement of the phthalocyanine pigments' characteristics by employing additives for the pigment compositions based on polyamides or polyamines, which are preferably aliphatic.
The invention consists in an additive for a phthalocyanine pigment which comprises an adduct of a copper phthalocyanine, a copper monochlorphthalocyanine or a mixture of these, in sulphonated form with a polyaminoamido or polyamino compound containing reactive amino groups, i.e. amino groups containing at least one free, and therefore salt-forming hydrogen atom.
The sulphonic derivatives of the phthalocyanine or monochlorphthalocyanine contain one or two -SO3H groups for each mole of phthalocyanine; a mixture of mono- and di-sulphonated derivatives may be used.
The polyaminoamido or polyamino compound used contains reactive polyamino groups in such amount as to exhibit an amine index of from 100 to 800 mg of KOH per gram of the compound.
Amongst suitable polyaminoamido and polyamino compounds all having an amine index within the above-indicated range there may be mentioned the following commercially available materials: (a) Genamid- (GMI) 250 (Genamid is the
trade-mark of General Mills Inc. USA),
being a polyamino imidazoline having
an amine index of 425450; (b) Genamid (GMI) 370, a polyamino
imidazoline having an amine index of 350400; (c) Genamid (GMI) 2000, a
polyaminoamide having an amine index
of 580--620; (d) Duomeen T (a product distributed by
AKZO Chemie) ("Duomeen" is a
Registered Trade Mark) a polyamine of
formula H2N(CH2)3NHC,8H3,; and (e) Wolfamids Nos. 3 and 4 ("Wolfamid" is
a Registered Trade Mark").
The invention also consists in a pigment composition comprising a copper phthalocyanine or chlorphthalocyanine pigment or pigment mixture and 515% by weight preferably 612% by weight, of an -adduct as described above.
The adduct may correspond in composition, as regards its phthalocyanine and/or chlorphthalocyanine content, with that of the pigment or pigment mixture, but this is not a necessary feature of the invention.
According to the invention, the pigment composition may be made by mixing the required pigment and adduct components in due proportion. Alternatively it can be made directly by partial sulphonation of the pigment or pigment mixture followed by reaction with the polyaminoamido or polyamino compound of the partially sulphonated material. In yet another alternative these two methods may be combined, in that the polyaminoamido or polyamino compound may be reacted with a mixture of the phthalocyanine pigment material and separately prepared sulphonated phthalocyanine pigment material.
In the direct method, partial sulphonation of phthalocyanine or chlorphthalocyanine pigment may be carried out to an extent giving an intermediate product containing 0.03 to 0.24 equivalents of-SO3H per mole of phthalocyanine. This intermediate, or an equivalent obtained by mixing an aqueous
paste of phthalocyanine (SO3H),~2 with an
aqueous paste of phthalocyanine in the
desired ratio, may then be reacted in the form of an aqueous slurry with an aqueous
acid solution of the polyamine derivative in the desired ratio. The aqueous slurry may suitably have a pH of 8-9. To promote the reaction the pH may then be adjusted to 3.5-5.5, and the mixture stirred for say 30 minutes to 2 hours at a temperature of from room temperature to 1000C. Finally, the mixture may be filtered and the product washed and dried.
An alternative, as indicated above, consists in preparing the adduct separately, i.e. in reacting the polyamime derivative with the aqueous dispersion of phthalocyanine (SO3H)12, and adding the resulting slurry to the aqueous slurry of the not-sulphonated phthalocyanine pigment material.
The following examples illustrate how the invention may be carried into effect.
Example 1.
In a 3-liter beaker, 450 g of an aqueous paste containing 43% by weight of Cu phthalocyanine in the beta form were intensely dispersed in 1500 ml. of hot water, whereupon 120 g of an aqueous paste containing 20% by weight of Cu phthalocyanine monosulphonic acid were added. After becoming a homogeneous slurry, dilute aqueous NaOH was added until the pH was about 9, and then a separately prepared solution of GMI 2000 (10 g) in 60 g of 20% by weight acetic acid was added as well.
Stirring was continued for 1 hour at 7800C, after which the slurry was filtered, washed with about 1 liter of water and finally dried.
In comparison with Cu phthalocyanine in the beta form without any additive, the greenish turquoise pigment so obtained exhibited considerably improved fluidity, gloss and transparency in its application in flexographic inks based on nitrocellulose.
Example 2.
In a 3-liter beaker, 250 g of an aqueous paste containing 40% by weight of Cu phthalocyanine in the alpha form and 250 g of an aqueous paste containing 40% by weight of Cu monochloro-phthalocyanine were intensely dispersed in 1500 ml. of hot water, and 80 g of an aqueous paste containing 20% by weight of Cu phthalocyanine monosulphonic acid were then added.
After the slurry mixture was stirred to homogeneity, dilute aqueous NaOH was added to adjust the pH to about 9, and a separately prepared solution of 10 g of GMI 2000 in 50 g of 20% acetic acid was then poured in.
The mixture was then worked up as in
Example 1, to give a washed and dried product exhibiting a reddish turquoise shade. In comparison with a similar mixture of phthalocyanines, but not containing the additive of the present invention, the product of Example 2 exhibited an improved fluidity, gloss and transparency in application to flexographic inks on a nitrocellulose basis.
Example 3.
In a 3-liter beaker, 450 g of an aqueous paste containing 43% by weight of Cu phthalocyanine in the beta form were intensely dispersed in 1500 ml. of hot water, and 120 g of an aqueous paste containing 20% by weight of Cu phthalocyanine monosulphonic acid were then added.
After the resulting slurry mixture became homogeneous, a separately prepared solution of Duomeen T acetate (10 g) in 50 g of 70% w/w acetic acid was added. Stirring was continued for 1 hour at 7O800C, after which the slurry was filtered, washed with about I liter of water and finally dried.
As compared with beta Cu phthalocyanine without any additive, the pigment so obtained exhibited considerable improvements as regards fluidity, gloss and transparency in its application in flexographic inks based on nitrocellulose.
Example 4.
In a 3-liter beaker, 450 g of an aqueous paste containing 43% by weight of beta Cu phthalocyanine were intensely dispersed in 1500 ml. of hot water.
In a second 500 ml. beaker, 50 g of a paste containing 20% by weight of Cu phthalocyanine monosulphonic acid were dispersed in 200 ml. of hot water, then the pH was brought to 9 with dilute NaOH, whereupon a separately prepared solution of 2.5 g of GMI 2000 in 15 g of 20% w/w acetic acid was added. Stirring was continued for 1 hour keeping the temperature at 800 C, whereupon the dispersion was poured into the first beaker.
The mixture was stirred intensely for about 30 minutes, then it was filtered, washed with about 1 liter of water and finally dried. The resulting product exhibited practically the same characteristics as that described in
Example 1.
WHAT WE CLAIM IS:
1. An additive for phthalocyanine pigments comprising an adduct of a copper phthalocyanine mono or disulphonic acid and/or of the corresponding monochloro- derivative with a polyaminoamido or polyamino compound having an amine index of from 100 to 800 mg of KOH per gram.
2. An additive according to claim 1 in which said compound is aliphatic.
3; A pigment composition comprising a copper phthalocyanine or chlorphthalocyanine pigment or pigment mixture and 515% by weight of an adduct according to claim 1 or 2.
4. A composition according to claim 3 in which 6-1 2% by weight of the adduct is present.
5. A process for preparing a pigment composition according to claim 3 or 4 in which the pigment or pigment mixture is compounded with the separately-prepared adduct.
6. A process according to claim 5 in which the pigment or pigment mixture and the adduct are each in the form of an aqueous dispersion and they are compounded by being stirred together at an acid pH.
7. A process for preparing a pigment composition according to claim 3 or 4 in which a mixture of the corresponding sulphonated and unsulphonated phthalocyanines and/or chlorphthalocyanines is reacted in the form of an aqueous dispersion with the polyaminoamido or polyamino compound.
8. A process according to claim 7 in which said mixture is obtained by partial sulphonation of the corresponding phthalocyanine and/or chlorphthalocyanine.
9. A process of preparing a pigment composition according to claim 3 or 4, substantially as exemplified.
10. Solvent inks comprising a pigment composition according to claim 3 or 4, or produced according to any of claims 5-9.
**WARNING** end of DESC field may overlap start of CLMS **.
Claims (10)
1. An additive for phthalocyanine pigments comprising an adduct of a copper phthalocyanine mono or disulphonic acid and/or of the corresponding monochloro- derivative with a polyaminoamido or polyamino compound having an amine index of from 100 to 800 mg of KOH per gram.
2. An additive according to claim 1 in which said compound is aliphatic.
3; A pigment composition comprising a copper phthalocyanine or chlorphthalocyanine pigment or pigment mixture and 515% by weight of an adduct according to claim 1 or 2.
4. A composition according to claim 3 in which 6-1 2% by weight of the adduct is present.
5. A process for preparing a pigment composition according to claim 3 or 4 in which the pigment or pigment mixture is compounded with the separately-prepared adduct.
6. A process according to claim 5 in which the pigment or pigment mixture and the adduct are each in the form of an aqueous dispersion and they are compounded by being stirred together at an acid pH.
7. A process for preparing a pigment composition according to claim 3 or 4 in which a mixture of the corresponding sulphonated and unsulphonated phthalocyanines and/or chlorphthalocyanines is reacted in the form of an aqueous dispersion with the polyaminoamido or polyamino compound.
8. A process according to claim 7 in which said mixture is obtained by partial sulphonation of the corresponding phthalocyanine and/or chlorphthalocyanine.
9. A process of preparing a pigment composition according to claim 3 or 4, substantially as exemplified.
10. Solvent inks comprising a pigment composition according to claim 3 or 4, or produced according to any of claims 5-9.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
IT2696976A IT1065261B (en) | 1976-09-08 | 1976-09-08 | PHTHALOCYANIN PIGMENTS OF IMPROVED CHARACTERISTICS IN SOLVENT INKS |
Publications (1)
Publication Number | Publication Date |
---|---|
GB1569837A true GB1569837A (en) | 1980-06-18 |
Family
ID=11220652
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB3698177A Expired GB1569837A (en) | 1976-09-08 | 1977-09-05 | Phthalocyanine pigments |
Country Status (6)
Country | Link |
---|---|
BE (1) | BE858523A (en) |
DE (1) | DE2739775A1 (en) |
ES (1) | ES462180A1 (en) |
FR (1) | FR2364250A1 (en) |
GB (1) | GB1569837A (en) |
IT (1) | IT1065261B (en) |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5212221A (en) * | 1991-05-11 | 1993-05-18 | Ciba-Geigy Corporation | Stabilized phthalocyanine pigment compositions |
US7255734B2 (en) | 2002-12-10 | 2007-08-14 | Clariant Produkte (Deutschland) Gmbh | Phthalocyanine pigment preparations |
US7377974B2 (en) | 2003-12-12 | 2008-05-27 | Clariant Produkte (Deutschland) Gmbh | Use of a pigment preparation based on C.I. pigment yellow 74 |
US7419541B2 (en) | 2003-12-12 | 2008-09-02 | Lariant Produkte (Deutschland) Gmbh | Monoazo pigment preparations based on C.I. Pigment Yellow 74 |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB1263684A (en) * | 1970-01-23 | 1972-02-16 | Ciba Geigy Uk Ltd | Treatment of pigments |
DE2506832C3 (en) * | 1975-02-18 | 1978-10-05 | Basf Ag, 6700 Ludwigshafen | Process for converting raw copper phthalocyanines into a pigment form |
-
1976
- 1976-09-08 IT IT2696976A patent/IT1065261B/en active
-
1977
- 1977-09-03 DE DE19772739775 patent/DE2739775A1/en active Granted
- 1977-09-05 GB GB3698177A patent/GB1569837A/en not_active Expired
- 1977-09-06 FR FR7726921A patent/FR2364250A1/en active Granted
- 1977-09-07 ES ES462180A patent/ES462180A1/en not_active Expired
- 1977-09-08 BE BE180772A patent/BE858523A/en not_active IP Right Cessation
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5212221A (en) * | 1991-05-11 | 1993-05-18 | Ciba-Geigy Corporation | Stabilized phthalocyanine pigment compositions |
US7255734B2 (en) | 2002-12-10 | 2007-08-14 | Clariant Produkte (Deutschland) Gmbh | Phthalocyanine pigment preparations |
US7459016B2 (en) | 2002-12-10 | 2008-12-02 | Clariant Produkte (Deutschland) Gmbh | Method for the production of phthalocyanine pigment preparations |
US7377974B2 (en) | 2003-12-12 | 2008-05-27 | Clariant Produkte (Deutschland) Gmbh | Use of a pigment preparation based on C.I. pigment yellow 74 |
US7419541B2 (en) | 2003-12-12 | 2008-09-02 | Lariant Produkte (Deutschland) Gmbh | Monoazo pigment preparations based on C.I. Pigment Yellow 74 |
Also Published As
Publication number | Publication date |
---|---|
DE2739775A1 (en) | 1978-03-09 |
FR2364250A1 (en) | 1978-04-07 |
ES462180A1 (en) | 1978-06-16 |
BE858523A (en) | 1978-03-08 |
DE2739775C2 (en) | 1987-12-03 |
IT1065261B (en) | 1985-02-25 |
FR2364250B1 (en) | 1980-08-01 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
PS | Patent sealed | ||
732 | Registration of transactions, instruments or events in the register (sect. 32/1977) | ||
PCNP | Patent ceased through non-payment of renewal fee |