US4069064A
Expired / Lapsed
US
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Phthalocyanine formulations having high gloss, which are stabilized against recrystallization and against change of modification
Assignee: BASF SE
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Filing: 1976-03-24
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Granted: 1978-01-17
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Expires: 1996-03-24
Abstract
Abstract A phthalocyanine formulation which is stabilized against recrystallization and change of modification and which contains, as the stabilizer (a) a finely divided phthalocyanine as the pigment and (b) a salt or the corresponding homogeneous mixture of (α) a phthalocyanine derivative, which carries basic groups ##STR1## (R 1 = H, alkyl of 1 to 20 carbon atoms, unsubstituted or substituted phenyl, --C 2 H 4 --NH) z H or --(C 3 H 6 --NH) z H, z = 1, 2 or 3, and R 2 = H, alkyl of 1 to 6 carbon atoms or cycloalkyl of 6 to 8 carbon atoms) and (β) an aliphatic sulfonic acid of 8 to 20 carbon atoms, a monoalkylbenzenesulfonic acid or dialkylbenzenesulfonic acid where alkyl is of 6 to 20 carbon atoms, or a monoalkylnaphthalenesulfonic acid or dialkylnaphthalenesulfonic acid where alkyl is of 6 to 20 carbon atoms, which acids may be substituted by hydroxyl, the molar ratio of α:β being from 1:1 to 1:5, and, if desired, one or more organic fluids or solutions of resins in these fluids. The formulations are stable even in aromatic hydrocarbons and produce pure, deep colorations which have high gloss.
Inventors
- 👤 Robert Nett
- 👤 Wolf Dieter Fechner
- 👤 Werner Jettmar
- 👤 Rudolf Polster
- 👤 Reinhard Sappok
- 👤 Eduard Hartmann
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-27 05:06
CPC Classifications
C; C09; C09B; C09B68/00; C09B68/40; C09B68/44; C09B68/441; C09B47/00; C09B47/04; C09B47/08; C09B67/00; C09B67/0032; C09B67/0033; C09B67/0034; C09B67/0035
Claims Analysis
Total Claims: 15
Claim 1
Independent Claim
331 words
A finely divided solid to pasty phthalocyanine formulation which is stable against recrystallization and change of modification, which gives colorations having good gloss, and which consists essentially of a. a finely divided phthalocyanine dispersed in insoluble form as the pigment and (b) from 10 to 40 percent by weight, based on (a), of a salt or the corresponding homogeneous mixture, also dispersed in insoluble form, of (α) one or more phthalocyanine derivatives of the formula ##STR39## where Pc is an n-valent radical of the metal-free phthalocyanine, of a copper phthalocyanine or of a mixture of these, X is --CH 2 --, ##STR40## --CH 2 --CH 2 --COO--C 2 H 4 -- or --CH 2 --CH 2 --COO--C 3 H 6 --, R 1 is hydrogen, alkyl of 1 to 20 carbon atoms, phenyl, phenyl which is substituted by methyl, methoxy, ethoxy or chlorine, --(C 2 H 4 --NH) z H or --(C 3 H 6 --NH) z H, R 2 is hydrogen, alkyl of 1 to 6 carbon atoms or cycloalkyl of 6 to 8 carbon atoms, alk is linear or branched saturated alkylene of 2 to 6 carbon atoms, R is hydrogen or alkyl of 1 to 4 carbon atoms, and R and R 2 may be linked to one another, n is a number from 2 to 5, z is an integer from 1 to 3 and the group ##STR41## may also be a heterocyclic ring selected from the group consisting of morpholinyl, thiomorpholinyl, piperazinyl, N-methylpiperazinyl, N-ethylpiperazinyl, piperidinyl, pyrrolidinyl and ##STR42## and (β) a saturated or unsaturated aliphatic sulfonic acid of 8 to 20 carbon atoms, a benzenesulfonic or naphthalenesulfonic acid, substituted by one or two alkyl groups each of 6 to 20 carbon atoms, and in which the benzene or naphthalene nucleus can be substituted by a hydroxyl group, or mixtures thereof, the molar ratio of (α) : (β) being from 1:1 to 1:5, and the said salt or corresponding mixture acting as a stabilizer in the formulation.
Claim 2
Dependent Claim
331 words
A finely divided solid to pasty phthalocyanine formulation which is stable against recrystallization and change of modification, which gives colorations having good gloss, and which consists essentially of a. a finely divided phthalocyanine dispersed in insoluble form as the pigment and (b) from 10 to 40 percent by weight, based on (a), of a salt or the corresponding homogeneous mixture, also dispersed in insoluble form, of (α) one or more phthalocyanine derivatives of the formula ##STR39## where Pc is an n-valent radical of the metal-free phthalocyanine, of a copper phthalocyanine or of a mixture of these, X is --CH 2 --, ##STR40## --CH 2 --CH 2 --COO--C 2 H 4 -- or --CH 2 --CH 2 --COO--C 3 H 6 --, R 1 is hydrogen, alkyl of 1 to 20 carbon atoms, phenyl, phenyl which is substituted by methyl, methoxy, ethoxy or chlorine, --(C 2 H 4 --NH) z H or --(C 3 H 6 --NH) z H, R 2 is hydrogen, alkyl of 1 to 6 carbon atoms or cycloalkyl of 6 to 8 carbon atoms, alk is linear or branched saturated alkylene of 2 to 6 carbon atoms, R is hydrogen or alkyl of 1 to 4 carbon atoms, and R and R 2 may be linked to one another, n is a number from 2 to 5, z is an integer from 1 to 3 and the group ##STR41## may also be a heterocyclic ring selected from the group consisting of morpholinyl, thiomorpholinyl, piperazinyl, N-methylpiperazinyl, N-ethylpiperazinyl, piperidinyl, pyrrolidinyl and ##STR42## and (β) a saturated or unsaturated aliphatic sulfonic acid of 8 to 20 carbon atoms, a benzenesulfonic or naphthalenesulfonic acid, substituted by one or two alkyl groups each of 6 to 20 carbon atoms, and in which the benzene or naphthalene nucleus can be substituted by a hydroxyl group, or mixtures thereof, the molar ratio of (α) : (β) being from 1:1 to 1:5, and the said salt or corresponding mixture acting as a stabilizer in the formulation.
Claim 3
Dependent Claim
22 words
A formulation as claimed in claim 1, wherein the content of (b) is from 20 to 30% by weight, based on (a).
Claim 4
Dependent Claim
20 words
A formulation as claimed in claim 1, wherein the molar ratio of (α) to (β) is from 1:2 to 1:4.
Claim 5
Dependent Claim
20 words
A formulation as claimed in claim 2, wherein the molar ratio of (α) to (β) is from 1:2 to 1:4.
Claim 6
Dependent Claim
59 words
A formulation as claimed in claim 1, which contains, as (a), metal-free phthalocyanine, copper phthalocyanine, copper phthalocyanine which contains up to 2 chlorine atoms or bromine atoms in the molecule, polychloro-copper phthalocyanine with from 3 to 16 chlorine atoms or polychlorobromo-copper phthalocyanine with from 1 to 14 chlorine atoms and from 15 to 2 bromine atoms in the molecule.
Claim 7
Dependent Claim
44 words
A formulation as claimed in claim 1, which contains, as (α), one or more phthalocyanine derivatives of the formula ##STR43## where Pc' is an n-valent copper phthalocyanine radical, X' is ##STR44## and R 1 and R 2 have the meanings given in claim 1.
Claim 8
Dependent Claim
54 words
A formulation as claimed in claimed in claim 6, wherein R 1 is alkyl of 1 to 10 carbon atoms, --(C 2 H 4 --NH) z H or --(C 3 H 6 --NH) z H, R 2 is alkyl of 1 to 4 carbon atoms or cyclohexyl, and z is 1, 2 or 3.
Claim 9
Dependent Claim
69 words
A formulation as claimed in claim 1, which contains, as (β), saturated or unsaturated aliphatic sulfonic acids of 10 to 20 carbon atoms, or monoalkylbenzenesulfonic or dialkylbenzenesulfonic acids where alkyl is of 8 to 18 carbon atoms, or monoalkylnaphthalenesulfonic or dialkylnaphthalenesulfonic acids where alkyl is of 8 to 18 carbon atoms, in which the benzene or naphthalene nucleus may carry a hydroxyl group or a mixture of these acids.
Claim 10
Dependent Claim
46 words
A formulation as claimed in claim 1, which contains, as sulfonic acids (β): dodecylbenzenesulfonic acid, dodecylphenolsulfonic acid, didodecylphenolsulfonic acid, dodecylnaphtholsulfonic acid, nonylphenolsulfonic acid, nonylbenzenesulfonic acid, octadecylphenolsulfonic acid, octadecylsulfonic acid, hexadexylsulfonic acid, 1-tetradecen-1-sulfonic acid, 1-octadecene-1-sulfonic acid, hydroxyoctadecylsulfonic acid, dodecylnaphthol-(1)-sulfonic acid, didodecyl-naphthol-(1)-sulfonic acid, octyl-naphthol-(1)-sulfonic acid and dioctylnaphthol-(1)-sulfonic acid.
Claim 11
Dependent Claim
77 words
A formulation as claimed in claim 8, wherein phthalocyanine derivatives (α) which are used are those of the formula ##STR45## in which X' is --CH 2 -- or --SO 2 --NH-alk', R 3 is hydrogen or alkyl of 1 to 4 carbon atoms, R 4 is alkyl of 1 to 4 carbon atoms or cyclohexyl, alk' is linear or branched saturated alkylene of 2 to 6 carbon atoms and n' is a number from 2 to 5.
Claim 12
Dependent Claim
16 words
A solids formulation as claimed in claim 1 in the form of a pulverulent homogeneous mixture.
Claim 13
Dependent Claim
74 words
A pasty formulation as claimed in claim 1 in which components (a) and (b) are suspended as insoluble particles in an organic fluid medium selected from the group consisting of aromatic hydrocarbons, halohydrocarbons, alcohols, glycols, glycol monoalkyl ethers, polyglycols, diacetone alcohol, benzyl alcohol, phenol, substituted phenols, naphthols, substituted naphthols, ketones, C 1 to C 5 alkyl esters of acetic acid, propionic acid, glycollic acid, lactic acid, carboxylic acid amides and N-methylpyrrolidone and mixtures thereof.
Claim 14
Dependent Claim
20 words
A pasty formulation as claimed in claim 12 including a natural, synthetic or semi-synthetic resin dissolved in said organic fluid.
Claim 15
Dependent Claim
23 words
A pasty formulation as claimed in claim 12 wherein the amount of (b) is from 20 to 30% by weight, based on (a).
References Cited (Backward Citations)
US3492253A
Cited
GB1241143A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1981-01-16 | 1981-07-18 | 1982-01-17 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1985-01-16 | 1985-07-18 | 1986-01-17 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1989-01-16 | 1989-07-18 | 1990-01-17 | $7700.00 | Window Closed / Lapsed |