JPS6410027B2 - - Google Patents

Description

[Detailed description of the invention]

Purpose of the Invention (Field of Industrial Application) The present invention is a method for applying paints or adhesives to the surface of various synthetic rubbers including polyolefin vulcanized rubber, or various synthetic resins including polyolefin synthetic resins and vinyl chloride. The present invention relates to a primer composition used as an undercoat to enhance the adhesion of these products. (Prior technology) There are many types of industrial rubber products, but polyolefin vulcanized rubbers such as ethylene-propylene-diene ternary copolymer rubber (EPDM) and ethylene-propylene copolymer rubber (EPM) are particularly popular. It exhibits outstanding performance in terms of weather resistance, aging resistance, ozone resistance, etc., and the operating temperature range is -50℃ to 150℃.
Rubber has excellent features such as being able to cover a wide range of areas, so it is now used in a wide variety of fields. In addition, depending on the application, natural rubber (NR), styrene-butadiene copolymer rubber (SBR), butadiene rubber (BR), isobutylene-isoprene copolymer rubber (IIR), chloroprene rubber (CR), acrylonitrile can be added to the above EPDM or EPM. -Rubbers blended with synthetic rubbers such as butadiene copolymer rubber (NBR), or rubbers blended with resins such as ABS resin, styrene resin (PS), polyethylene (PE), and polypropylene (PP) are also used in many fields. There is. In addition, polyolefin-based synthetic resins such as PP and PE mentioned above, like polyolefin-based vulcanized rubber, exhibit outstanding performance in terms of weather resistance, aging resistance, ozone resistance, etc., and are inexpensive, making them suitable for various vehicle parts. It is used in a wide range of applications, including electronic products and appliances. (Problem to be solved by the invention) However, polyolefin-based vulcanized rubbers such as EPDM and EPM, and polyolefin-based synthetic resins such as PP and PE do not contain polar groups in the main chain of their molecules, so they are reactive. There is a problem in that even if a paint or adhesive is applied to the surface of a molded product made from these rubbers or resins, the resulting coating film is likely to peel off. However, although many countermeasures have been attempted to address the above-mentioned problems, no satisfactory solution has yet been found. In addition, when molded products are made from resins that contain a large amount of plasticizer, such as vinyl chloride resin, the plasticizer migrates to the surface of the molded product over long periods of use, so paint applied to the surface may There is a problem that the adhesive strength of the adhesive gradually decreases. As a result of repeated research in view of the above problems, the present inventor has discovered a primer composition that has strong adhesion to polyolefin vulcanized rubber, polyolefin synthetic resin, vinyl chloride resin, etc., and has achieved the present invention. It has been reached. Structure of the Invention (Means for Solving Problems) That is, the present invention comprises (a) chloroprene rubber, (b) phenolic resin, (c) polyisocyanate and/or polyurethane, and (d) at least one hydroxyl group at the end of the molecule. The above-mentioned problems are solved by employing a primer composition comprising a mixture of a hydrocarbon polymer with a saturated or partially saturated main chain, and (e) an organic solvent. (Function) Since the primer composition having the above structure has strong adhesion to polyolefin-based vulcanized rubber, polyolefin-based synthetic resin, or vinyl chloride resin, by using this as an undercoat, polyolefin-based The adhesion of paints and adhesives applied to the surface of molded products made of vulcanized rubber, polyolefin synthetic resin, vinyl chloride resin, etc. is significantly improved. (Example) Hereinafter, the constituent components of the primer composition of the present invention will be explained by giving specific examples. (a) Chloroprene rubber is a non-vulcanized polymer obtained by emulsion polymerization of chloroprene.
It is an adhesive polymer that has excellent properties such as weather resistance, ozone resistance, heat aging resistance, and chemical resistance, and also exhibits high adhesion to various rubbers and synthetic resins. (b) Phenol resin is an adhesive polymer obtained by heating and condensing phenol and aldehyde (mainly formaldehyde) using an alkali such as NaOH as a catalyst. Modified phenolic resins containing resin components are also used. (c) Polyisocyanates include 2,4-tolylene diisocyanate, hydrogenated 2,4-tolylene diisocyanate, 4,4'-diphenylmethane diisocyanate, hydrogenated 4,4'-diphenylmethane diisocyanate, 1, Diisocyanates such as 5-naphthalene diisocyanate, xylene diisocyanate, hydrogenated xylene diisocyanate, 1,6-hexamethylene diisocyanate, isophorone diisocyanate, or 4,4′,4″-triphenylmethane triisocyanate, tris-(p-isocyanate phenyl ) - It is an adhesive polymer obtained by polymerizing multifunctional isocyanates such as thiophosphate. Polyurethane is an adhesive polymer obtained by polymerizing the above-mentioned isocyanate and polyol in a molar ratio such that the isocyanate is in excess. It is an adhesive polymer containing an NCO group or an OH group at the molecular end, which is obtained by adding a chain extender and further carrying out a polymerization reaction.The above polyol can be either a polyester polyol or a polyether polyol. The polyol components of polyester polyols include ethylene glycol,
1,2-propylene glycol, 1,4-butanediol, 1,3-butanediol, 2,3
-butanediol, 1,5-pentanediol, 1,6-pentanediol, 1,6-hexanediol, neopentyl glycol, diethylene glycol, dipropylene glycol,
Examples include triethylene glycol and trimethylolpropane. Examples of organic acid components include dicarboxylic acids such as succinic acid, phthalic acid, phthalic anhydride, isophthalic acid, maleic acid, adipic acid, azelaic acid, and sebacic acid. On the other hand, examples of polyether polyols include polyoxypropylene diol, polytetramethylene glycol ether, and polyoxyethylene diol. In addition to the above-mentioned examples, polyols include chloroprene rubber, acrylic resin, etc.
Although various types of polyols can be used, it is preferable to use the polyester polyols described above when applying to polymers containing a large amount of plasticizers such as vinyl chloride resins. The above-exemplified polyisocyanates and polyurethanes may be used alone, or may be mixed in any proportion. (d) Hydrocarbon polymers with a saturated or partially saturated main chain containing hydroxyl groups in the molecule include polyhydroxypolyolefin with an average molecular weight of 1000 to 5000 (manufactured by Mitsubishi Chemical Industries, product name "Polytail-H", "Polytail-HA"), or 1 or more per monomer molecule, preferably 1.8
Contains ~5.0 hydroxyl groups and has a saturated or partially saturated main chain with an average molecular weight of ~500
50,000, preferably 1,000 to 20,000 polyhydroxypolybutadiene polymer (Japanese Patent Application Laid-Open No. 142695-1983)
can be exemplified. Since all of the above-mentioned hydrocarbon polymers contain hydroxyl groups in their molecules, they are characterized in that compositions with various properties can be obtained by utilizing the reactivity of these hydroxyl groups. Therefore, by mixing the chloroprene rubber, phenolic resin, polyisocyanate and/or polyurethane, and the above-exemplified hydrocarbon polymer in an organic solvent, a primer composition that has strong adhesion to various polymers can be obtained. is obtained. In addition, chloroprene rubber, phenolic resin,
When mixing polyisocyanate and/or polyurethane, 1 to 200 parts by weight of phenol resin to 100 parts by weight of chloroprene rubber,
An appropriate amount of polyisocyanate is 0.5 to 50 parts by weight, phenol resin is 1 part by weight or less and 200 parts by weight or more, and polyisocyanate and/or polyurethane is 0.5 part by weight or less and 50 parts by weight or more, which will reduce the adhesion. observed. Furthermore, when mixing with a hydrocarbon polymer, the mixture of chloroprene rubber, phenolic resin, polyisocyanate and/or polyurethane may be used in a ratio of 1 to 99 parts by weight per 10 parts by weight of the hydrocarbon polymer. (e) Next, the organic solvents used during mixing include saturated hydrocarbons such as n-hexane, cyclohexane, and ethylcyclohexane; aromatic hydrocarbons such as benzene, toluene, and xylene; dioxane, tetrahydrofuran, etc. ethers; acetate esters such as ethyl acetate and propyl acetate; ketones such as acetone, cyclohexanone, ethylcyclohexanone, and methyl ethyl ketone; solvents or solvents appropriately selected from chlorinated hydrocarbons such as trichlorethylene, tetrachloroethylene, and methyl chloroform; A mixed solvent consisting of two or more types can be exemplified. Next, the above primer composition can be applied to various synthetic resins such as PP, PE, and vinyl chloride, as well as polyolefin vulcanized rubber such as EPDM and EPM. Rubber components such as NR, SBR, IIR, CR, NBR, ABS resin, PS, PE, PP, ethylene, etc. in amounts that will not be lost.
It also includes those containing resin components such as vinyl acetate copolymer resin (EVA). In addition, the above-mentioned polyolefin-based vulcanized rubber and those to which the above-mentioned various rubber components and resin components are added usually contain compounds such as sulfur, morpholine disulfide, and dicumyl peroxide as vulcanizing agents. Oxide, 2-mercaptobenzothiazole as a vulcanization accelerator, zinc dimethyldithiocarbamate, tetramethylthiuram disulfide, anti-aging agent, phenyl-α-naphthylamine, 2,6-di- t-butyl-p-
Cresol, carbon black, magnesium carbonate, clay as fillers, dioctyl sebacate, mineral oil, etc. as plasticizers are added. No special equipment is required to apply the primer composition, and the primer composition can be applied simply by a conventional coating method such as dipping, spraying, or brushing. Further, since the above primer composition is a one-component type and has a very long pot life, if the viscosity increases due to evaporation of the solvent, the viscosity can be adjusted by adding the solvent again.Example 1 Chloroprene rubber Phenol resin and polyisocyanate are mixed in an organic solvent to form the following table-1.
The compositions shown in ~4 (hereinafter abbreviated as CR polymer) were prepared. The phenolic resins used were Tamanol 520S, Tamanol 521 (both manufactured by Arakawa Chemical Co., Ltd., phenolic resin), Tamanol 803 (manufactured by Arakawa Chemical Co., Ltd., terpene phenol resin), and Tamanol 340 (manufactured by Arakawa Chemical Co., Ltd., rosin-modified phenolic resin).

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[Table] Next, the above CR-based polymer and the polyhydroxypolyolefin (“Polytail-H” or “Polytail-HA”) having an average molecular weight of 1,000 to 5,000 and having a hydroxyl group at the end of the molecule were mixed in toluene. Primer compositions-1 to 1 shown in Tables 5 to 9 of
5 was adjusted.

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[Table] Next, in order to examine the adhesion of the above primer compositions-1 to 5, tests were conducted using the following method. A rubber compound having the composition shown in Table 10 was heated at 160℃ for 30 minutes.
A 2 mm thick base material made of EPDM was produced by vulcanization for minutes, and this was cut into 100 mm x 100 mm squares to prepare two test pieces. Next, as shown in the figure, the primer composition 1 shown in Table 1 was applied to the edge of each side of the two test pieces 3, and the primer composition 1 was air-dried at room temperature for 30 minutes.
was formed. Next, a chloroprene rubber adhesive 2 having the composition shown in Table 11 was applied to the surface of the primer layer 1 and air-dried for 30 minutes at room temperature.
were bonded and left at room temperature for 24 hours. Thereafter, this test piece 1 was pulled in the direction of the arrow in the figure to measure its tensile shear strength, and the results shown in Table 13 were obtained. Table 13 also shows the results of a similar tensile shear test using Primer Compositions 2 to 5 and a primer composition (Comparative Example 1) having the composition shown in Table 12 below.

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[Table] As a result, the tensile shear strength of the test pieces using primer compositions-1 to 5 was extremely high. In addition, since the primer composition of Comparative Example 1 lacks phenolic resin and polyisocyanate,
Tensile shear strength decreased. The compositions of Comparative Examples 2 to 10 below have been conventionally used as undercoating agents for polyolefin vulcanized rubbers and polyolefin synthetic resins. Comparative Example 2 A primer composition was prepared by diluting "Ester Resin-20" (manufactured by Toyobo Co., Ltd., saturated polyester resin) with a mixed solvent consisting of methyl ethyl ketone/toluene = 1/9. Comparative Example 3 A primer composition was prepared by diluting "Vinyrite-VMCH" (manufactured by Union Carbide, a vinyl chloride-vinyl acetate copolymer resin) with a mixed solvent consisting of methyl ethyl ketone/toluene = 1/1. Comparative Example 4 A primer composition was prepared by diluting "Eslec BM-2" (manufactured by Sekisui Chemical Co., Ltd., butyral resin) with a mixed solvent consisting of butanol/xylene = 1/1. Comparative Example 5 A primer composition was prepared by diluting "Orestar M55-80A" (manufactured by Mitsui Toatsu, moisture-curing polyurethane resin) with toluene. Comparative Example 6 A mixture consisting of "Desmofene-100" (manufactured by Bayer, polyhydroxy compound)/"Desmodyur-R" (manufactured by Bayer, polyisocyanate) = 1/1.5 was mixed with methylene glycol/butyl acetate/toluene = 1/1/1. A primer composition was prepared by diluting with a mixed solvent consisting of: Comparative Example 7 A primer composition was prepared by diluting "Betucosol J-534" (manufactured by Dainippon Ink & Chemicals, a linseed oil-modified long oil alkyd resin) and cobalt naphthenate (desiccant) with a mineral base. Comparative Example 8 "Betsukosol J-524" (manufactured by Dainippon Ink & Chemicals, linseed oil modified long oil alkyd resin) / "Super Betsukamine J-100" (manufactured by Dainippon Ink & Chemicals, butylated melamine resin) = A primer composition was prepared by diluting a 4/1 mixture with xylene. Comparative Example 9 A primer composition was prepared by diluting a mixture of "Acryloid C-110V" (manufactured by Rohm & Haas, thermoplastic acrylic resin)/nitrocellulose = 99/1 with toluene. Comparative example 10 "Acrydik 47-712" (manufactured by Dainippon Ink & Chemicals, thermosetting acrylic resin) / "Supervetsucomin 47-508" (manufactured by Dainippon Ink & Chemicals, butylated melamine resin) = 4/ A primer composition was prepared by diluting a mixture of 1 with a mixed solvent of toluene/butyl acetate=1/1. Therefore, these compositions were used as primers as described above.
EPDM was applied to a test piece, and a chloroprene rubber adhesive having the composition shown in Table 11 was applied thereon to bond the test pieces together, and then the tensile shear strength was measured using the method described above. As a result, the tensile shear strengths of test pieces using these primers were all extremely low. (1.0Kg/ ^cm2 or less) Example 2 Polyester polyol and isocyanate were dissolved in a mixed solvent of 1,1,1-trichloroethane/dimethylformamide = 100/60, and reacted in dry nitrogen gas at 80℃ for 3 hours. After this, a chain extender was added and the mixture was further reacted at 80°C for 3 hours to prepare polyurethanes-1 to 4. The polyester polyol, isocyanate, and chain extender used are shown in the table below.
Shown in 14-17.

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[Table] Next, the above polyurethane, chloroprene rubber and phenol resin were mixed in an organic solvent to prepare CR polymers 5 to 8 shown in Tables 18 to 21 below.

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[Table] Next, the above CR-based polymer and the polyhydroxypolyolefin ("Polytail-HA") having an average molecular weight of 1000 to 5000 and having a hydroxyl group at the molecular end were mixed in toluene, and the results are shown in Tables 22 to 25 below. Primer compositions-6 to 9 shown below were prepared.

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[Table] Next, in order to examine the adhesion of the above primer compositions-6 to 9, a tensile shear test was conducted using the following method. PVC resin with the composition shown in Table 26 was heated to 170°C.
A 2mm thick base material is manufactured by extrusion molding, and this is
Two test pieces were created by cutting into a 100 mm x 100 mm square.

[Table] Next, as in Example 1, Primer Composition-6 was applied to each side of the two test pieces, and then air-dried at room temperature for 30 minutes to form a primer layer. After applying the chloroprene rubber adhesive shown in Table 11 to the surface of the primer layer,
After air drying for 30 minutes, the test pieces were bonded together and left at room temperature for 24 hours. Then, the tensile shear strength was measured in the same manner as in Example 1, and the results shown in Table 28 were obtained. In addition, primer composition-7~
Table 28 also shows the results of a similar tensile shear test using a primer composition (Comparative Example 11) having the composition shown in Table 27 below.

【table】

[Table] As a result, the tensile shear strengths of the test pieces using primer compositions-6 to 9 were all extremely high. In addition, since the primer composition of Comparative Example 11 had an excessive proportion of phenolic resin, the tensile shear strength decreased. In addition, after applying the chloroprene rubber adhesive to the surface of each of the compositions of Comparative Examples 2 to 10 as an undercoat and bonding the test pieces, the tensile shear strength was measured using the method described above. The tensile shear strength of the test pieces using the primer was extremely low (1.0 Kg/cm ² or less). From the above test results, it was found that the primer composition -
It was found that all of Nos. 1 to 9 exhibited excellent adhesion as an undercoat when applying an adhesive to EPDM or vinyl chloride resin. Example 3 Next, the primer compositions-1 to 5 were used as an undercoat when coating a base material made of EPDM.
The adhesion of the coating film was measured using the following method. The primer compositions 1 to 5 were applied to the EPDM test piece used in Example 1 by a dipping method, and after air-drying at room temperature for 30 minutes, a urethane composition having the composition shown in Table 29 was applied with dry nitrogen gas. A urethane paint obtained by reacting for 3 hours at 80°C was applied and cured at room temperature for 24 hours.

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[Table] After that, the adhesion of the urethane coating applied to each test piece was measured by a cross-cut test, and as a result, all test pieces showed sufficient adhesion (100/100). On the other hand, each of the compositions of Comparative Examples 2 to 10 was applied to each of the above test pieces by the dipping method and air-dried at room temperature for 30 minutes.
Allowed to cure for hours. The adhesion of these coatings was measured by a cross-cut test, and the adhesion of all coatings was extremely weak (0/100). Example 4 Next, the primer composition was used as an undercoat when coating a base material made of vinyl chloride resin.
The adhesion of the coating film using Samples Nos. 6 to 9 was measured by the following method. Each of the primer compositions -6 to 9 was applied by a dipping method to the test piece made of the vinyl chloride resin used in Example 2, and after air-drying at room temperature for 30 minutes, a urethane paint having the composition shown in Table 29 was applied. and cured at room temperature for 24 hours. Thereafter, the adhesion of the urethane coating applied to each test piece was measured by a cross-cut test, and as a result, all test pieces showed sufficient adhesion (100/100). On the other hand, when each of the compositions of Comparative Examples 2 to 10 was used as an undercoat, as in Example 3, the adhesion of each coating was extremely weak (0/100). From the above test results, it was found that the primer composition -
It was found that all of Nos. 1 to 9 exhibited excellent adhesion as an undercoat when coating paint on EPDM or vinyl chloride resin. Next, an example of using the primer compositions-1 to 9 as an undercoat when applying paints or adhesives to various rubber products for automobiles will be described. Application example 1 Door weather strip EPDM is often used in door weather strips that seal the gap between the car body and the door. Therefore, each of primer compositions 1 to 9 was applied to the surface of a weather strip base material made of EPDM, and then a urethane paint having the composition shown in Table 29 was applied thereon, and after air-drying at room temperature for 1 hour, Furthermore, a 5% by weight solution of dimethyl silicone oil (100,000 cSt) in toluene was applied. Usage Example 2 Glass Run EPDM is also widely used in glass runs, which are used in the parts of door sashes that slide against the window glass. Therefore, primer compositions 1 to 9 were each applied to the surface of a glass run base material made of EPDM, and a urethane paint having the composition shown in Table 29 above was applied thereon and air-dried at room temperature for 24 hours. Next, the abrasion resistance test of the coating film formed on the surface of the weather strip and glass run treated as described above was conducted in the following manner. Testing machine: KI type abrasion tester Test conditions: Friction element Glass (thickness 5mm) Load: 3Kg Friction element cycle: 60 times/min Friction element stroke: 145mm Test method: Part of the above weather strip and glass run was tested. It was attached to a machine and the coating surface was rubbed according to the test conditions. As a result, no exposure of the base material was observed in any case even after repeated friction 50,000 times. Furthermore, a 180° bending test was conducted to check the followability of each of the above coating films, and all showed extremely good followability, and the flexibility and flexibility, which are the characteristics of EPDM, were not impaired in any way. Next, the above-mentioned wear resistance test was conducted using each of the compositions of Comparative Examples 2 to 10, but the base materials of both the weather strip and the glass run were exposed due to repeated friction 100 to 150 times. Ivy. Usage example 3 Electrostatic flocking products: Some glass run products have electrostatic flocking processing using fibers on the sliding surface with the window glass. Primer composition-1 to the glass run base material
9 was applied by the dipping method and left at room temperature for 30 minutes, and then a urethane adhesive having the composition shown in Table 29 above was applied to the surface, and piles made of nylon-66 staple fibers were electrostatically flocked. An electrostatic flocking product was obtained by curing this urethane adhesive with hot air. Next, an abrasion resistance test of the coating film on the electrostatic flocked product treated as described above was conducted in the following manner. Testing machine: Reciprocating abrasion tester Test conditions: Friction element glass (thickness 5 mm) Friction element cycle 60 times/min Friction element stroke 145 mm Test method: A part of the electrostatic flocking product above was attached to the testing machine, The coating surface was rubbed according to the test conditions. As a result, no exposure of the base material was observed even after 20,000 repetitions of friction. Furthermore, the primer compositions-1 to 9 can also be used for the following purposes. Usage Example 4 Diaphragm After applying Primer Compositions 1 to 9 and leaving it at room temperature for 30 minutes, acrylonitrile was coated with Urthane paint having the composition shown in Table 29 above.
In order to investigate the gasoline resistance of the butadiene copolymer rubber (NBR) diaphragm base material, the untreated diaphragm was immersed in gasoline at 24°C for 48 hours, and the mass change rate before and after immersion was measured using the following equation. ΔW = [(W ₂ − W ₁ )/W ₁ ] × 100 (%) (W ₁ is the mass before immersion and W ₂ is the mass after immersion.) As a result, ΔW of the untreated diaphragm is
30%, whereas △W of the product subjected to the above treatment decreased to 20.1%.
The primer composition was found to be extremely effective in improving the gasoline resistance of diaphragm substrates. Usage example 5 Brake cylinder cup Brake made of styrene-butadiene copolymer rubber (SBR) coated with primer compositions 1 to 9, left at room temperature for 30 minutes, and then coated with urethane paint having the composition shown in Table 29 above. In order to investigate the glycol resistance of the cylinder cup base material, the untreated brake cylinder cup body was immersed in commercially available low molecular weight ethylene glycol at 24°C for 200 hours, and the mass change rate before and after immersion was measured using the same method as for the diaphragm. ΔW was measured. As a result, the △W of the untreated brake cylinder cup body was 3.5%, whereas the △W of the treated brake cylinder cup body decreased to 1.5%. It was found that it is highly effective in improving glycol resistance. Usage example 5 Wiper blade Primer compositions 1 to 9 were applied to the surface of a wiper blade made of EPDM and left at room temperature for 30 minutes, and then a urethane paint having the composition shown in Table 29 was applied, resulting in an untreated surface. A wiper blade with superior followability and low frictional resistance during sliding was obtained compared to the conventional wiper blade. From the above test results, primer composition-1
It was found that Examples 1 to 9 are extremely useful as primers for coating polyolefin vulcanized rubber with paints and adhesives. Moreover, primer compositions-1 to 9 can be used not only as primers but also as adhesives alone, and can also be used as paints by adding pigments, dyes, etc. Effects of the Invention As detailed above, the primer composition of the present invention is said to exhibit extremely strong adhesion to various rubbers and synthetic resins such as polyoffine-based vulcanized rubber, polyoffine-based synthetic resin, and vinyl chloride resin. This invention is highly effective and is extremely excellent as an undercoat when applying adhesives or paints to the surfaces of base materials made of the various rubbers and synthetic resins mentioned above.

[Brief explanation of the drawing]

The figure is a cross-sectional view schematically showing a state in which a primer layer was formed on each end of two test pieces, and then the ends of both test pieces were joined via a chloroprene rubber adhesive. 1... Primer layer, 2... Adhesive, 3... Test piece.

Claims (1)

[Scope of Claims] 1 (a) chloroprene rubber, (b) phenolic resin, (c) polyisocyanate and/or polyurethane, (d) main chain with at least one hydroxyl group at the end of the molecule is saturated or partially A primer composition comprising a mixture of: a saturated hydrocarbon polymer; (e) an organic solvent; 2 Based on 100 parts by weight of the chloroprene rubber,
Claim 1, wherein the phenol resin is mixed in a proportion of 1 to 200 parts by weight and the polyisocyanate and/or polyurethane is mixed in a proportion of 0.5 to 50 parts by weight.
The primer composition described in . 3 The hydrocarbon polymer has at least one hydroxyl group at the end, and has an average molecular weight of 1000
5,000 polyhydroxypolyolefin.