JP3010754B2 - Chlorinated polypropylene-modified polyurethane, its production method and printing ink - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a method for producing a chlorinated polypropylene-modified polyurethane suitable for printing inks, and more particularly to a method for coating various plastic films, plastic sheets or synthetic resin molded articles.
Particularly useful printing inks.

[0002]

2. Description of the Related Art In recent years, with the diversification of packaging materials and the advancement of packaging technology, when various plastic films are used for packaging materials, printing is performed for decoration or surface protection of the plastic films. However, printing ink for such printing has been required to have high performance and quality for these various plastic films.

[0003] In particular, with respect to printing inks, a wide range of adhesiveness to various composite films, and further various post-processing suitability, for example, various laminating work suitability, boil suitability, retort suitability, in order to enhance the beauty and luxury of packaging containers. It is also necessary to respond to such issues.

Generally, gravure printing, flexographic printing, and the like are used for printing plastic films and the like.
In the case of film printing as a packaging material, since most of them are of a winding type, printing inks are required to have a quick drying property. When used as food packaging, it is particularly required that the amount of residual solvent be small.

[0005] Further, in order to improve the performance of the packaging material, dry lamination and extrusion lamination may be performed after printing. Taking advantage of the fact that other films are superior in strength and airtightness, in particular, films such as polyester and nylon are laminated with a polyethylene film or a polypropylene film or the like. Examples of the laminating method include a dry laminating process using a urethane-based adhesive or the like and an extrusion laminating process using an anchor coat agent. In lamination, an aluminum foil may be further interposed in the middle, and a packaging material capable of boiling and retorting may be used. Also, although strength is not required until retort processing, in the field of packaging materials based on transparent substrates, stretched polypropylene (OPP) is used as the base film and directly coated with molten polypropylene without using an anchor coating agent. A laminating method (usually called a PP direct laminate) is also performed.

[0006] In order to perform such post-processing, it is required that the printing ink used in the preceding stage has not only the adhesiveness to various base films and the printability but also the suitability for each post-processing. Such various suitability is mainly determined by the binder resin used for the printing ink.

Conventionally, as a binder for printing ink,
When a polyester film is used as a thermoplastic polyester resin, and when a nylon film or a polyester film is used, a two-pack type reactive resin of a polyester resin having a hydroxyl group or the like and an isocyanate compound is used. Recently, printing inks using a polyurethane resin as a binder have been used as those having a wide suitability for nylon, polyester and other base films.

On the other hand, for a polyolefin to be subjected to PP direct lamination, a printing ink using a chlorinated polyolefin having a relatively low chlorination degree such as chlorinated polypropylene as a binder is used.

However, printing inks using a thermoplastic polyester resin not only have a limited base material but also do not have sufficient drying properties and have problems in workability such as occurrence of blocking. Therefore, the pot life is short, there are various restrictions on work, and there is an economic loss such as disposal of unused ink.

A printing ink using a polyurethane resin as a binder has sufficient adhesiveness to a nylon film or a polyester film by itself, but does not adhere to a general-purpose film such as a polyolefin film such as a polyethylene film or a polypropylene film. Does not yet have sufficient adhesiveness and is suitable for lamination, especially PP
There is a problem that the suitability for direct lamination is insufficient.

On the other hand, a printing ink using a chlorinated polyolefin as a binder has good adhesiveness to a polyolefin film, but does not have sufficient adhesiveness to a nylon film or a polyester film. Is limited, and although it has PP direct lamination suitability, there is no boil suitability and retort suitability,
Limited use.

It has also been attempted to mix a chlorinated polyolefin with a polyurethane resin for the purpose of improving the adhesiveness to a polyolefin film, a nylon film or a polyester film and having suitability for various laminating processes, especially for PP direct laminating. However, both have poor compatibility, and printing inks using this as a binder are inadequate in stability, printability, boilability and retort suitability, and are difficult to use.

As described above, in the conventional printing ink, the substrate film is limited, or even if it has general versatility with respect to the substrate film, the adhesiveness is insufficient, and the laminating or boiling process is performed. However, it did not have sufficient suitability for retort processing. Therefore, it is necessary to produce a printing ink containing a binder suitable for each in accordance with applications such as various base films, various laminating processes, or retorting processes, and it is necessary to produce each time an ink manufacturing process, a printing process or This has a major problem in inventory management of materials and inks.

[0014]

DISCLOSURE OF THE INVENTION The present invention provides excellent adhesion, lamination processing, boil processing, retort processing to any of various plastic films such as polyester, nylon, polyethylene, and polypropylene as printing materials. An object of the present invention is to provide a resin composition for a printing ink having appropriate properties.

[0015]

The present inventors have made intensive studies to solve the above problems, and as a result, a specific modified polyurethane resin having a chlorinated polypropylene skeleton in the molecule has solved all of the above problems. Find out what can be done,
The present invention has been completed.

That is, the present invention relates to a method of preparing a compound (a1) having an azo group and a primary or secondary amino group and / or a hydroxyl group by using a polymer polyol component (a2), an organic diisocyanate compound (a3), A polyurethane (A) having at least one azo group in a molecule obtained by reacting with a chain extender (a4);
The present invention relates to a method for producing a chlorinated polypropylene-modified polyurethane, characterized in that chlorinated polypropylene (B) is reacted with a peroxide using a peroxide.

The polyurethane (A) having at least one azo group in the molecule is a compound (a1) having an azo group and a primary or secondary amino group and / or a hydroxyl group.
It can be obtained by reacting with a polymer polyol component (a2), an organic diisocyanate compound (a3), a chain extender (a4) and the like.

The compound (a1) having an azo group and a primary or secondary amino group and / or a hydroxyl group includes 2,2
2'-azobis [2- (2-imidazolin-2-yl)
Propane], 2,2'-azobis [2-methyl-N-
(2-hydroxyethyl) propionamide], 2,
2'-azobis [2-methyl-N- [1,1-bis (hydroxymethyl) 2-hydroxyethyl] propionamide], 2,2'-azobis [2- (hydroxymethyl) propionitrile] and the like. Can be

As the polymer polyol component, various known components generally known as a polymer polyol component of polyurethane can be used. For example, polyether polyols such as polymers or copolymers such as ethylene oxide, propylene oxide, and tetrahydrofuran; ethylene glycol, diethylene glycol, triethylene glycol, 1,2-propanediol, 1,3-propanediol, and 1,3 -Butanediol, 1,4-butanediol, neopentyl glycol, pentanediol, 3-methyl-1,5-pentanediol, 1,6
-Hexanediol, octanediol, 1,4-butynediol, various known saturated and unsaturated low molecular weight glycols such as dipropylene glycol or alkyl glycidyl ethers such as n-butyl glycidyl ether and 2-ethylhexyl glycidyl ether; Monocarboxylic acid glycidyl esters such as versatic acid glycidyl ester, adipic acid, maleic acid, fumaric acid,
Dibasic acids such as phthalic anhydride, isophthalic acid, terephthalic acid, succinic acid, oxalic acid, malonic acid, glutaric acid, pimelic acid, azelaic acid, sebacic acid, suberic acid, and the corresponding acid anhydrides and dimer acids And polyester polyols obtained by ring-opening polymerization of a cyclic ester compound; and other polycarbonate polyols, polybutadiene glycols, and bisphenol A to which ethylene oxide or propylene oxide is added. And various known high-molecular polyols generally used in the production of polyurethane, such as glycols.

In the case of a high molecular polyol obtained from a glycol and a dibasic acid among the high molecular polyol components, up to 5 mol% of the glycol can be replaced by the following various polyols. . For example, glycerin, trimethylolpropane, trimethylolethane, 1,2,6-hexanetriol, 1,2,4-
Butanetriol, sorbitol, pentaerythritol and the like.

The molecular weight of the high molecular polyol component is appropriately determined in consideration of the solubility, drying properties, blocking resistance and the like of the obtained polyurethane.
It is good to be about 0, preferably in the range of 1000 to 6000. If the molecular weight is less than 700, the printability tends to decrease due to the decrease in solubility.
If it exceeds 300, drying property and blocking resistance tend to decrease.

As the diisocyanate compound, various known aromatic, aliphatic or alicyclic diisocyanates can be used. For example, 1,5-naphthylene diisocyanate, 4,4'-diphenylmethane diisocyanate, 4,4'-diphenyldimethylmethane diisocyanate, 4,4'-dibenzyl isocyanate, dialkyldiphenylmethane diisocyanate, tetraalkyldiphenylmethane diisocyanate,
3-phenylene diisocyanate, 1,4-phenylene diisocyanate, tolylene diisocyanate, butane-1,4-diisocyanate, hexamethylene diisocyanate, isopropylene diisocyanate, methylene diisocyanate, 2,2,4-trimethylhexamethylene diisocyanate, 2,4 4-trimethylhexamethylene diisocyanate, cyclohexane-1,4-
Diisocyanate, xylylene diisocyanate, isophorone diisocyanate, lysine diisocyanate, dicyclohexylmethane-4,4'-diisocyanate,
Typical examples thereof include 1,3-bis (isocyanatomethyl) cyclohexane, methylcyclohexane diisocyanate, m-tetramethylxylylene diisocyanate, and dimer isocyanate obtained by converting a carboxyl group of dimer acid into an isocyanate group.

As the chain extender component, various known amines can be used. For example, ethylenediamine, propylenediamine, hexamethylenediamine, triethylenetetramine, diethylenetriamine, isophoronediamine, dicyclohexylmethane-4,4'-diamine and the like can be mentioned. In addition, 2-hydroxyethylethylenediamine, 2-hydroxyethylpropylenediamine, di-2-hydroxyethylethylenediamine, di-2-hydroxyethylpropylenediamine,
Representative examples thereof include diamines having a hydroxyl group in the molecule, such as -hydroxypropylethylenediamine and di-2-hydroxypropylethylenediamine, and dimerdiamines obtained by converting a carboxyl group of dimer acid into an amino group.

Further, a reaction terminator may be used.
Examples of such a reaction terminator include dialkylamines such as di-n-butylamine and alcohols such as ethanol and isopropyl alcohol.

In order to obtain a polyurethane having at least one azo group in a molecule used in the present invention, the polyol component and the organic isocyanate compound are used in an equivalent ratio of 1.3 / 1 to 3.0 / isocyanate group / hydroxyl group. 1
Urethanization reaction under the conditions of (1) to prepare a prepolymer having an isocyanate group, preferably a free isocyanate content of 0.5 to 10% by weight, and then prepare these in an appropriate solvent with an azo group, primary to secondary Is reacted with a compound having an amino group and / or a hydroxyl group, a chain extender and, if necessary, a reaction terminator, but the compounds may be reacted at once. The polyurethane having at least one azo group in the molecule has a molecular weight of 5,000.
0-200,000 can be used, 10,000
~ 150,000 are preferred. If it is less than 5,000, drying properties, blocking resistance, film strength, and oil resistance tend to decrease, while if it exceeds 200,000, the viscosity of the resin solution increases, and the pigment dispersibility tends to decrease. Absent.

On the other hand, the chlorinated polypropylene (B) which reacts with the polyurethane (A) having at least one azo group in the molecule has a molecular weight of 5,000 to 100,0.
00, preferably 7,000 to 70,000. If the molecular weight is less than 5,000, blocking tends to occur, and the suitability for lamination tends to be insufficient. On the other hand, if it exceeds 100,000, the transparency of the film becomes poor in addition to the solubility. Further, the chlorine content of the chlorinated polypropylene (B) is preferably from 10 to 60% by weight, particularly preferably from 15 to 45%. When the chlorine content is less than 10% by weight, the solubility in an organic solvent is reduced. On the other hand, when the chlorine content is more than 60% by weight, a printing ink containing a chlorinated polypropylene-modified polyurethane modified with a content exceeding 60% by weight is used. Adhesion to polyolefin films and other synthetic resins is reduced.

The method for obtaining the desired chlorinated polypropylene-modified polyurethane by using the above-mentioned chlorinated polypropylene and the polyurethane having at least one azo group in the molecule is the same as the conventional acrylic-modified or maleic-acid-modified polyurethane. It can be made to react by various methods.

That is, chlorine is extracted from the chlorinated polyolefin by a peroxide (benzoyl peroxide or the like) radical as an initiator, and at least 1
The chlorinated polypropylene-modified polyurethane resin having the desired functionality can be obtained by reacting with a radical residue generated at a concentration higher than the azo group cleavage in the polyurethane having azo groups.

The weight ratio of the chlorinated polypropylene (B) to the polyurethane (A) having at least one azo group in the molecule is preferably in the range of 5/95 to 65/45. Especially 10/90 to 50/5
It is preferably in the range of 0. When the use ratio of the chlorinated polypropylene (B) is less than 5% by weight, the adhesiveness to polyolefin is reduced, and when it exceeds 65% by weight, the adhesiveness to polyester and nylon, the boiling and retort suitability are reduced.

In the above-mentioned production method, the solvent used is usually a well-known aromatic solvent such as benzene, toluene, xylene, etc., a solvent for printing ink, methanol, ethanol, isopropanol, n-
Examples thereof include alcohol solvents such as butanol, ketone solvents such as acetone, methyl ethyl ketone and methyl isobutyl ketone, and ester solvents such as ethyl acetate and butyl acetate. These may be used alone or in a mixture of two or more.

When a printing ink is produced by using the chlorinated polypropylene-modified polyurethane obtained as described above, various pigments and the above-mentioned solvent are added, and the mixture is kneaded and dispersed. , Additives such as plasticizers, surfactants for improving ink fluidity and dispersibility, or chlorinated polyolefins such as compatible nitrified cotton, chlorinated polyethylene, chlorinated polypropylene, chlorinated ethylene / propylene, Chlorsulfonated polyolefin, ethylene / vinyl acetate copolymer, or chlorinated or chlorsulfonated product thereof, maleic acid resin,
Resins such as a vinyl chloride / vinyl acetate copolymer and polyurethane can be used in combination.

[0032]

EXAMPLES The present invention will be described in detail below with reference to Production Examples, Examples and Comparative Examples, but the present invention is not limited to these Examples. Parts and% in Production Examples, Examples, and Comparative Examples represent parts by weight and% by weight, respectively.

Production Example 1 (Synthesis of polyurethane having at least one azo group in the molecule) In a four-necked flask equipped with a stirrer, a thermometer, a reflux condenser, and a nitrogen gas inlet tube, adipic acid and 3-methyl-1,
Into 1,000 parts of a polyester diol having a molecular weight of 2,000 obtained from 5 pentanediol and 222 parts of isophorone diisodianate were charged at 90 ° C. under a nitrogen stream.
Allowed to react for hours. Then, the mixture was cooled to 15 ° C., and 77.3 parts of isophorone diamine, 1-di-n-butylamine 1
2.9 parts, 6.8 parts of 2,2′-azobis [2- (2-imidazol-2-yl) propane], 1464 parts of methyl ethyl ketone, and 733 parts of isopropyl alcohol are added, and the mixture is stirred at 15 ° C. for 3 hours. The reaction was carried out for a time to obtain a polyurethane resin solution (1) having at least one azo group in the molecule.

Production Example 2 The same reactor as in Production Example 1 was charged with 2,000 parts of polycaprolactone diol having a molecular weight of 2,000 and 200 parts of isophorone diisocyanate, and reacted at 90 ° C. for 6 hours under a nitrogen stream. Then, the mixture was cooled to 15 ° C., and 61.9 parts of isophoronediamine, di-n-butylamine 1
0.3 parts, 2,2′-azobis [2- (2-imidazolin-2-yl) propane], 5.5 parts, 1416 parts of methyl ethyl ketone and 709 parts of isopropyl alcohol were added, and the mixture was stirred at 15 ° C. at 15 ° C. for 3 hours. The reaction was carried out for a time to obtain a polyurethane resin solution (2) having at least one azo group in the molecule.

Production Example 3 In the same reactor as in Production Example 1, a molecular weight of 2,000 obtained from adipic acid and 3-methyl-1,5-pentanediol was used.
Of polyester diol and 222 parts of isophorone diisocyanate, and 90
The reaction was carried out at 6 ° C. for 6 hours. It is then cooled to 50 ° C., 1464 parts of methyl ethyl ketone, and 2,2′-
Azobis [2- (hydroxymethyl) propionitrile]
5.4 parts, and reacted at 50 ° C. for 2 hours with stirring,
This was further cooled, and 77.3 parts of isophoronediamine,
12.9 parts of di-n-butylamine and 731 parts of isopropyl alcohol were added and reacted at 15 ° C. for 3 hours with stirring to obtain a polyurethane resin solution (3) having at least one azo group in the molecule.

Embodiment 1 In a four-necked flask equipped with a stirrer, thermometer, reflux condenser and nitrogen gas inlet tube, chlorinated polypropylene (molecular weight 1)
(100 parts of a toluene solution containing 50% of 0000 and a chlorine content of 30%) and a polyurethane resin solution (1) having at least one azo group in a molecule obtained in Production Example 1 (70).
3 parts were charged, and further 3 parts of benzoyl peroxide were charged and reacted at 90 ° C. for 2 hours. Further, the benzoyl peroxide was added one part at a time every two hours, and reacted for 4 hours. To this was added 243 parts of toluene, and the solid content was 30%.
Viscosity at 25 ° C. 700 cps, molecular weight 72,000
Chlorinated polypropylene modified polypropylene resin (A)
I got

The obtained chlorinated polypropylene-modified polyurethane resin solution (A) was sealed in a metal can and stored at 25 ° C., and after 14 days, there was no change without separation or gelling. .

A mixture of 40 parts of the chlorinated polypropylene-modified polyurethane resin solution (A), 30 parts of titanium oxide, 15 parts of toluene and 15 parts of methyl ethyl ketone was kneaded to prepare a white printing ink.

The viscosity of the obtained printing ink was adjusted with a mixed solvent of toluene, methyl ethyl ketone and isopropyl alcohol (weight ratio: 60:30:10), and corona-treated polypropylene was used with a gravure calibrator equipped with a 35 μm deep gravure plate. Printing on film (OPP), corona-treated polyethylene terephthalate film (PET) and corona-treated nylon film (NY)
It dried at 0 degreeC-50 degreeC, and obtained the printing film.

With respect to the obtained printed film,
Extrusion lamination strength, dry lamination strength, boilability and retort suitability, and PP direct lamination suitability were evaluated by the following test methods, and the results are shown in Table 1. 1) Adhesion After leaving the printed matter for one day, a cellophane tape was stuck on the printed surface, and the appearance of the printed film when the cellophane tape was rapidly peeled off was visually judged. The criteria were as follows. ◎: The printed film did not come off at all.…: 80% or more of the printed film remained on the film.…: 50% to 80% remained on the film. X: 50% or less remained on the film.

2) Extrusion Lamination Strength An imine-based anchor coating agent was used for OPP and an isocyanate-based anchor coating agent was used for PET and NY, and molten polyethylene was laminated by an extrusion laminator. After cutting, the T-peel strength was measured.

3) Dry laminating strength CPP (unstretched polypropylene) film is laminated by a dry laminating machine using a urethane adhesive on the printed matter, and after 3 days, the peeling strength is measured by the same method as in the measurement of extrusion lamination. did.

4) Boilability and retort suitability After dry laminating, a laminate is formed into a bag, a mixture of water / salad oil is put as the contents, and after sealing, the boilability is 100 ° C for 30 minutes and the retort suitability is After heating at 120 ° C. for 30 minutes, the presence or absence of lamination was visually determined from the appearance. The sample was evaluated as 浮 when no lamination was lifted, and as × when delamination occurred on the entire surface.

5) Suitability for PP direct lamination The above-mentioned OPP printed matter was directly laminated with a melted polypropylene by an extrusion laminator, and two days later, the peel strength was measured by the same method as the extrusion lamination strength.

Embodiment 2 FIG. In the same reactor as in Example 1, 96 parts of a toluene solution containing 50% of chlorinated polypropylene (molecular weight 30,000, chlorine content 35%) and a polyurethane resin having at least one azo group in the molecule (2) 681 parts,
Further, 3 parts of benzoyl peroxide was charged and reacted at 90 ° C. for 2 hours. Further, the above-mentioned benzoin peroxide was added one part at a time every 2 hours and reacted for 4 hours. To the mixture was added 236 parts of toluene, and a chlorinated polypropylene-modified polyurethane resin solution having a solid content of 30%, a viscosity of 900 cps at 25 ° C. and a molecular weight of 80,000 ( B) was obtained.

The ink was prepared, printed and evaluated in the same manner as in Example 1 except that the chlorinated polypropylene-modified polyurethane resin solution (A) was replaced with the chlorinated polypropylene-modified polyurethane resin solution (B). Table 1 shows the results.

The chlorinated polypropylene-modified polyurethane resin solution (A) was replaced with the chlorinated polypropylene-modified polyurethane resin solution (B), and the stability was tested in the same manner as in Example 1. As a result, separation, gelation, etc. Without any change.

Embodiment 3 FIG. In the same reactor as in Example 1, 100 parts of a toluene solution containing 50% of chlorinated polypropylene (molecular weight 10,000, chlorine content 30%) and a polyurethane resin having at least one azo group in the molecule (3 ) 703 parts and benzoyl peroxide 3 parts were further charged and reacted at 90 ° C. for 2 hours. Further, the above-mentioned benzoyl peroxide was added one part at a time every 2 hours and reacted for 4 hours. 243 parts of toluene was added, and a chlorinated polypropylene-modified polyurethane resin solution having a solid content of 30%, a viscosity of 520 cps at 25 ° C. and a molecular weight of 67,000 ( C) was obtained.

An ink was prepared, printed and evaluated in the same manner as in Example 1 except that the chlorinated polypropylene-modified polyurethane resin solution (A) was replaced with the chlorinated polypropylene-modified polyurethane resin solution (C). Table 1 shows the results.

The chlorinated polypropylene-modified polyurethane resin solution (A) was replaced with the chlorinated polypropylene-modified polyurethane resin solution (C), and the stability was tested in the same manner as in Example 1. As a result, no separation or gelation occurred. ,
There was no change.

Comparative Example 1 In the same reactor as in Example 1, 100 parts of a toluene solution containing 50% of chlorinated polypropylene (molecular weight: 150,000, chlorine content: 35%) and a polyurethane resin having at least one azo group in the molecule (1) 703 parts, and 3 parts of benzoyl peroxide, 9
The reaction was performed at 0 ° C. for 2 hours. When 1 part of the benzoyl peroxide was further added and allowed to react, the viscosity rapidly increased after about 2 hours. Therefore, 243 parts of toluene was added to stop the reaction. The obtained resin solution was a viscous non-uniform solution having a solid content of 30% and a viscosity of 65,000 cps at 25 ° C., and was not suitable as a binder for printing ink.

Comparative Example 2 The same reactor as in Production Example 1 was charged with 1,000 parts of polycaprolactone diol having a molecular weight of 2,000 and 222 parts of isophorone diisocyanate, and reacted at 90 ° C. for 6 hours under a nitrogen stream. Next, 82.0 parts of isophorone diamine, 12.9 parts of di-n-butylamine, 1300 parts of toluene,
1300 parts of methyl ethyl ketone and 615 parts of isopropyl alcohol were added, and the mixture was reacted at 50 ° C. for 3 hours with stirring.
s, polyurethane resin solution with molecular weight of 65,000 (D)
I got

An ink was prepared, printed and evaluated in the same manner as in Example 1 except that the chlorinated polypropylene-modified polyurethane resin solution (A) was replaced with the polyurethane resin solution (D). Table 1 shows the results.

Further, 1000 parts of the obtained polyurethane resin solution (D) and a chlorinated polypropylene solution (chlorine content 30%, molecular weight 10,000, solid content 50%) 111
The parts were mixed and tested for stability in the same manner as in Example 1. As a result, separation, gelation, and the like occurred.

Further, 1000 parts of the obtained polyurethane resin solution (D) and a hydroxyl group-containing chlorinated polypropylene solution (chlorine content: 28%, hydroxyl content: 10%, molecular weight: 1)
(50000, solid content 50%) were mixed and tested for stability in the same manner as in Example 1. As a result, separation, gelation, and the like occurred.

Comparative Example 3 Chlorinated polypropylene modified polyurethane resin solution (A)
Chlorinated polypropylene solution (chlorine content 30
%, Molecular weight 100000, solid content 30% toluene solution)
To prepare ink, print,
An evaluation was performed. Table 1 shows the results.

[0057]

[Table 1]

[0058]

According to the present invention, excellent adhesiveness, storage stability and suitability for laminating (especially PP) can be applied to any of various plastic films such as polyester, nylon, polyethylene, polypropylene and the like as a substrate.
Suitable for direct lamination) It is possible to provide a resin composition for a printing ink having excellent properties such as suitability for boil processing and suitability for retort processing.

──────────────────────────────────────────────────続 き Continued on the front page (58) Fields investigated (Int. Cl. ⁷ , DB name) C08G 18/00-18/87 C09D 11/00-11/20 CA (STN) REGISTRY (STN)

Claims (5)

(57) [Claims] 1. A compound (a1) having an azo group and a primary or secondary amino group and / or a hydroxyl group, comprising a polymer polyol component (a2), an organic diisocyanate compound (a3), and a chain extender ( a4) reacting polyurethane (A) having at least one azo group in the molecule thereof with chlorinated polypropylene (B) having a molecular weight of 5,000 to 100,000 using peroxide A method for producing a chlorinated polypropylene-modified polyurethane, comprising: 2. The method for producing a chlorinated polypropylene-modified polyurethane according to claim 1, wherein the chlorine content of the chlorinated polypropylene (B) is 10 to 60% by weight. 3. A polyurethane (A) having at least one azo group in a molecule, and a chlorinated polypropylene (B)
The method for producing a chlorinated polypropylene-modified polyurethane according to claim 1, wherein a weight ratio of the chlorinated polypropylene-modified polyurethane is 95/5 to 45/65. 4. The method according to claim 1, wherein
Chlorinated polypropylene modified polyurethane obtained by the method. (5) The chlorinated polypropylene modifier according to claim 4.
Printing-in, characterized by containing conductive polyurethane
Ki.