JPS61136555A - Surface modifier for organic pigment - Google Patents

Abstract

PURPOSE:To provide a surface modifier for an organic pigment containing a specified N-(long chain acyl) basic amino acid, which shows good dispersion in order solvent, resin and rubber and produces an organic pigment having bright color tone and excellent water repellency and printing properties. CONSTITUTION:The modifier contains at least one N-(long chain acyl) basic amino acid having at least one 8-22C aliphatic acyl group in the molecule (e.g. N-lauroyllysine). Organic pigment treated with the modifier shows good dispersibility in an organic solvent such as methyl ethyl ketone or toluene, resins such as polyurethane or epoxy resins and rubber such as natural or styrene/butadiene rubbers, develops bright color, has excellent water repellency and printing properties and is suitable for coating, plastics, printing ink, rubber, stationery, paper-making, etc.

Description

DETAILED DESCRIPTION OF THE INVENTION Field of Industrial Application The present invention relates to an organic compound containing at least one N-long chain acyl basic amino acid having at least one aliphatic acyl group having 8 to 22 carbon atoms in the molecule. Pigment surface modifier. The organic pigment imparted with dispersibility according to the present invention is used in the fields of paints, resins, inks, ink, plastics, stationery, and the like.

BACKGROUND OF THE INVENTION Conventionally, organic pigments used in the above-mentioned fields include phthalocyanine pigments, dioxane pigments, quinacridone M materials, anthraquinone pigments, indigo, thioindigo pigments, gynophthalone pigments, azo pigments,
Examples include perinone, perylene pigments, isoindolinone pigments, and carbon black.

Generally, the color tone and coloring power of these III pigments largely depend on their particle size and particle size distribution, so they are used after being crushed into a fine powder. However, the results obtained in this way
l! It is known that pigments have poor dispersibility and have drawbacks such as agglomeration of pigment particles in non-aqueous vehicles, resulting in uneven color and loss of gloss.

Therefore, various methods have been disclosed as methods for solving such problems. For example, a method in which a powdered pigment is dispersed in an 0Tffi agent and made into a paste by a flashing method or a grinding method has been used for a long time. In addition, there is a method in which a water-containing cake containing MU is suspended in a W-containing solvent using a surfactant, heated, filtered, washed with water, and dried (Japanese Patent Publication No. 40-1844
), a method using a pigment composition obtained by mixing a pigment, a large amount of a water-soluble anionic activator, and a water-soluble polymer with water, and spray-drying the mixture (JP-A-49-7887); Method of treatment with an activator (Unexamined Japanese Patent Publication No. 51
-88523), method using thermoplastic resin and solvent (
JP-A-51-54620), a method of flashing using a water-soluble thermoplastic resin and a pigment water-containing cake (JP-A-51-54620);
4-95838) and the like are disclosed.

F who is trying to decide whether this invention or AV! ff Problems As mentioned above, many inventions have been made to improve the dispersibility of organic pigments, but many problems still remain. For example, when an activator is contained as a dispersant, yellowing or discoloration may occur during the production of laminated paper, and when applied to printing inks, paints, etc., the activator may cause problems such as deterioration of water repellency and printing properties. . Furthermore, pigment compositions using thermoplastic resins require a large amount of resin to achieve uniform dispersion, resulting in a decrease in pigment content, resulting in a decrease in tinting power or in the case of pigment compositions that can only be applied to vehicles that are compatible with the resin used. There are drawbacks such as not being able to do it.

Means for Solving the Problems The present inventors have conducted intensive research to solve these drawbacks, and as a result, we have developed N-acyl lysine (Japanese Patent Application No. 175,709/1986), which we previously developed as a surface modifier for inorganic M family. ) is contained in an organic pigment to impart dispersibility to the organic a1F4.
has dramatically improved dispersibility in various media, and by adding dispersible organic pigments to printing inks and paints, its water repellency, printing characteristics, and color clarity can be improved. was completed. Furthermore, it was discovered that another basic amino acid, acyl lysine, has similar effects, leading to the completion of the present invention.

That is, the present invention uses at least one type of N-long chain acyl basic amino acids having at least one aliphatic acyl group having 8 to 22 carbon atoms in the molecule as a surface reforming agent for organic pigments. It is an organic pigment surface modifier containing .05 to 40 vt%.

Basic amino acids that are constituents of the N-long chain acyl basic amino acids used in the present invention include lysine and ornithine, which may be in either optically active forms or racemic forms. In addition, as the fatty acid that is the other component, fatty acids having 8 to 22 carbon atoms are used, and examples thereof include caproic acid, capric acid, lauric acid, myristic acid, valmitic acid, stearic acid, and oleic acid. acid, behenic acid, isostearic acid, coconut oil fatty acid,
Examples include hydrogenated beef tallow fatty acids.

The N-long chain acyl basic amino group used in the present invention is
So-called 5CHOTTEN, in which fatty acid chloride is dropped into the alkaline aqueous solution of the basic amino acid mentioned above.
It can be obtained by BAUMANN reaction. It can also be obtained by heating and dehydrating a fatty acid salt of a basic amino acid at a temperature of 100°C to 250°C.

(Special Publication Showa 5l-28610). To illustrate the N-long chain acyl basic amino acid obtained in this way, N-
Caproyl lysine, N-lauroyl lysine, N-valmitoylly sine, N, N-dilauroyl lysine, N, N-
Distearoyl lysine, N-oleoyl lysine, N-isostearoyl lysine, N-cocoyl lysine, N-hydrogenated beef tallow fatty acid acyl lysine, N-caproyl ornithine,
N-lauroyl ornithine, N, N-dilauroyl ornithine, N, N-dipalmitoyl ornithine, N-stearoyl ornithine, N-oleoylornithine, N-
Examples include isostearoylornithine, N-cocoylornithine, and N-hardened beef tallow fatty acid acylornithine.

A method for obtaining an organic pigment with dispersibility by incorporating an N-long chain acyl basic amino acid into an organic pigment with dispersibility is to add the N-long chain acyl basic amino acid to an organic U material as it is and to use a ball mill or an atomizer. - A tri-blend method in which the components are mixed and co-pulverized using a pulverizer such as a Henschel mixer, or a wet processing method in which the 11M ingredients are added to a suitable solvent, mixed with agitation, and then the solvent is removed.

Furthermore, when adding organic pigments to paints, resins, etc., it is also possible to use a method in which N-long chain acyl basic amino acids are directly added and mixed using a ball mill, heated roll, or the like. There are no particular restrictions on the form and particle size of the N-long chain acyl basic amino acid used in the present invention, and it may be used after being appropriately pulverized as required.

Organic pigments used in the production of dispersible organic pigments using the N-long chain acyl basic amino acid of the present invention as a dispersant include phthalocyanine pigments, dioxane pigments, quinacridone pigments, anthraquinone pigments, indigo, Examples include thioindigo pigments, quinophthalone pigments, azo pigments, perinone/perylene pigments, isoindritsuno pigments, and carbon black. In addition, the amount of N-long chain acyl basic amino acids added to these organic pigments varies depending on the method of addition, but in the triblend method it is 0.5% to 20% of the organic pigment, and in the wet method it is 0.5% to 20%. 0.05% to 20% is usually used. Also,
Ike surfactants conventionally used within the range that does not impair the effect of N-long chain acyl basic amino acids,
For example, there is no problem in using rosin soap, metal soap, sodium alkylbenzene sulfonate, a condensate of formaldehyde and sodium naphthalene sulfonate, polyoxyethylene nonylphenyl ether, and the like.

Effects of the present invention The organic pigments imparted with dispersibility of the present invention can be used in organic solvents such as ketones such as methyl ethyl ketone, methyl isobutyl ketone, and cyclohexanone, esters such as ethyl acetate, hydrocarbons such as toluene, and polyurethane vA resins. , vinyl chloride-vinyl acetate copolymers, epoxy resins, phenolic resins, acrylic resins, cellulose resins, polyamide resins, urea resins, and other resins, natural rubber, styrene-butadiene rubber, urethane rubber, and other rubbers with excellent dispersion and brightness. It has a unique color tone. Moreover, it has properties such as excellent water repellency and printing properties that cannot be defeated by conventional dispersants, so it is used in various fields such as paints, resins, plastics, printing inks, rubber, stationery, and paper manufacturing. It is suitable for

Next, the content of the present invention will be explained in more detail by giving examples.

Example 1 Phthalocyanine blue water-containing cake (solid content 30%) 1
00g containing 1.5g of N-lauroyl lysine
Add to 100 ml of NNaOH solution and neutralize by adding an equivalent volume of 1N HCl while vigorously stirring with a homogenizer. After continuing to stir for 1 hour, the mixture is filtered, washed with water, dried, and pulverized.

The phthalocyanine blue thus treated has excellent dispersibility in linseed oil varnish, mineral oil, etc., compared to untreated phthalocyanine blue, and forms a printing ink with brightness and density.

Example 2 Water-containing cake of Shinkasha red (solid content 25%) 100
lNNa containing 1 g of N-stearoyl lysine
0) In addition to 100 ml of I solution, add an equivalent amount of I N HC1 solution and neutralize while stirring vigorously with a homogenizer. After stirring for 1 hour, the mixture is filtered, washed with water, dried, and crushed.

The Sinka Charette thus obtained has excellent dispersibility in toluene and spindle oil, and exhibits high water repellency, so it is suitable as a pigment for paints.

Example 3 Phthalocyanine green water-containing cake (solid content 25%)
100g containing 1g of N-stearoyl lysine
NNaOH solution? In addition to 2100 ml, neutralize by adding an equivalent amount of 1N HCl 3j while stirring vigorously with a homogenizer. After continuing to stir for 1 hour,
Filter, wash with water, dry and crush.

The phthalocyanine green thus refined has excellent dispersibility in toluene and spindle oil.

Example 4 5 g of N-cocoyl ornithine was added to 100 g of carbon black and mixed for 30 minutes in a ball mill. Such carbon black has excellent dispersibility in mineral oil and is suitable as a pigment for printing ink.

Example 5 10 g of the organic pigment obtained in Examples 1 to 3 was mixed with 90 g of various dispersion mediums in a paint shaker for 10 minutes, and 2
The dispersion stability was visually judged after being left for 4 hours, and the results are shown in Table 1.
It was shown to. In addition, for comparison 19+1:, the surface modifier N-
The alkaline solution of long-chain acyl lysine and the water-containing cake of Material J were dried as they were without adding a neutralizing agent and pulverized in the same manner as in Examples 1 to 3.

Claims (1)

[Claims] An organic pigment surface modifier containing at least one N-long chain acyl basic amino acid having at least one aliphatic acyl group having 8 to 22 carbon atoms in the molecule.