JPH0525392A - Curable composition - Google Patents

Abstract

PURPOSE:To obtain a curable composition suitable for sealing material, adhesive, etc., providing cured materials having slight change of color tone during outdoor exposure. CONSTITUTION:100 pts.wt. polysulfide polymer or polysulfide polyether polymer is blended with 1-50 pts.wt. oxidizing agent and 0.1-30 pts.wt. surfactant and/or unsaturated fatty acid and/or unsaturated fatty acid salt and/or aromatic amine to give the objective curable composition.

Description

Detailed Description of the Invention

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a curable composition, and more particularly to a curable composition which gives a cured product with little change in color tone when exposed to the outdoors and is suitable for use as a sealing material, an adhesive or the like.

[0002]

2. Description of the Related Art A polymer containing two or more thiol groups in one molecule easily reacts with an oxidant to form a high molecular weight product and becomes a cured product.
Widely used for adhesives.

Such thiol group-containing polymers are described, for example, in US Pat. No. 2,466,963. This polysulfide polymer has excellent oil resistance, chemical resistance,
It is used as a raw material for sealing materials because of its flexibility.

Further, Japanese Patent Application No. 2-1094 filed by the applicant earlier
The polysulfide polyether polymer obtained by the polyether and the polysulfide polymer described in the specification of No. 61 has good compatibility with a general-purpose and inexpensive plasticizer, and a cured product by reducing the amount used. It is suitable as a sealing material because the coating film does not soften even when a paint is applied to it.

[0005]

When such a polysulfide polymer or polysulfide polyether polymer is cured with an oxidizing agent, a cured product having good durability can be obtained. However, when PbO ₂ or the like is used as the oxidizing agent, it is exposed outdoors. The color of the surface of the cured product may change from gray to grey-brown upon exposure, and although it does not affect the physical properties, it is aesthetically unfavorable depending on the intended use.

[0006] Therefore, an object of the present invention is to provide a curable composition which gives a cured product whose surface color change is small even when exposed to the outdoors.

[0007]

As a result of earnest research in view of the above object, the present inventors obtained it by adding a predetermined amount of a specific compound together with an oxidizing agent to a polysulfide polymer or a polysulfide polyether polymer. The present inventors have found that the composition gives a cured product with significantly less discoloration upon outdoor exposure, and have conceived the present invention.

That is, the first curable composition of the present invention comprises (A) 100 parts by weight of polysulfide polymer, (B) 1 to 50 parts by weight of an oxidizing agent, and (C) (i) a surfactant. ,
(ii) unsaturated fatty acid and / or a salt thereof, and (iii) 0.1 to 30 parts by weight of at least one aromatic amine.

The second curable composition of the present invention is (A)
In the main chain, _{(i) - (R 1 O) n} - ( where, R ₁ is 2 carbon atoms
4 is an alkylene group, and n is an integer of 6 to 200. ) And a polyether moiety represented by (B)-(C ₂ H ₄ OCH ₂ OC ₂ H ₄ -S
_x )-, and a structural unit represented by-(CH ₂ CH (OH) CH ₂ -S _x )-(where x is an integer of 1 to 5), and () C) -C ₂ H ₄ OCH ₂ OC ₂ H ₄ -SH
And / or -CH ₂ CH (OH) CH ₂ -SH with respect to 100 parts by weight of a polysulfide polyether polymer having a thiol group, (B) an oxidizing agent 1 to 50
At least 1 part by weight of (C) (i) surfactant, (ii) unsaturated fatty acid and / or salt thereof, and (iii) aromatic amine
And 0.1 to 30 parts by weight of the seed.

The present invention will be described in detail below. [1] Polysulfide Polymer The polysulfide polymer in the first curable composition of the present invention is represented by the following general formula (1). HS (R ₂ S _x ) _m R ₂ SH (1) (wherein, x is an integer of 1 to 5, m is an integer of 1 to 50, and R ₂ is -CH ₂ CH. _{2 -, -C 2 H 4 OC} 2 H 4 -, -C 2 H 4 OCH 2 OC 2 H 4 -
, -C ₄ H ₈ OC ₄ H _8- and other alkylene groups or alkylene ether groups and other organic residues. )

The above polysulfide polymer has fluidity at room temperature and has a molecular weight of 100 to 200,000, preferably 4
It is from 00 to 50,000.

Preferred examples of such polysulfide polymers are described in US Pat. No. 2,466,963.

[2] Polysulfide Polyether Poly
Polysulfide polyether polymer in the second curable composition of the mer present invention, in the main chain _{(a) - (R 1 O) n} -
(However, R ₁ is an alkylene group having 2 to 4 carbon atoms, and n is 6 to
Indicates an integer of 200. ) Polyether part represented by
_{(B) - (C 2 H 4 OCH} 2 OC 2 H 4 -S x) -, and _{- (CH 2 CH (OH)} CH 2 -S x) - ( here, x is an integer of 1 to 5. It represented contain a structural unit, and to end with), _{(iii) -C 2 H 4 OCH 2 OC} 2 H 4 -SH
And / or has a thiol group represented by —CH ₂ CH (OH) CH ₂ —SH.

The polyether moiety of (a) and the structural unit of (b) may be bonded in any sequence. In addition, the ratio is such that (i) the-(R ₁ O) _n -component is 2 to 95% by weight, (b)
-(C ₂ H ₄ OCH ₂ OC ₂ H ₄ )-component is 3 to 70% by weight,-(CH ₂ CH
It is preferable that the (OH) CH ₂ ) -component is 1 to 50% by weight and the polysulfide bond S _x is 1 to 60% by weight.

The number average molecular weight of this polysulfide polyether polymer is usually 600 to 200,000, preferably 800 to 50,000.

An example of a method for producing such a polysulfide polyether polymer is described in Japanese Patent Application No. 2-109461. Specifically, for example, it can be manufactured by the following two methods.

The first method for producing a polysulfide polyether polymer is (a) HS (C ₂ H ₄ OCH ₂ OC ₂ H ₄ S _x ) _m C ₂ H ₄ OCH ₂ OC ₂ H ₄ SH ... ( 2) (where x is an integer of 1 to 5 (the average is about 2),
m is an integer of 1 to 50. A polysulfide polymer starting material represented by), during (b) a main _{chain, - (R 1 O) n} -
(However, R ₁ is an alkylene group having 2 to 4 carbon atoms, and n
Represents an integer of 6 to 200. ) And a structure represented by-(CH ₂ CH (OH) CH ₂ -S _x )-(where x is an integer of 1 to 5, preferably 2). A thiol group-containing polyether polymer containing a unit and having a thiol group represented by -CH ₂ CH (OH) CH ₂ -SH at the terminal, (a) / (b) = 95/5 It consists of reacting in a weight ratio of 5/95.

The polysulfide polymer starting material is fluid at room temperature and has a molecular weight of 100 to 200,000, preferably 400 to 50,000. A preferred example of such a polysulfide polymer starting material is US Pat.
No. 6,963.

The molecular weight of the polyether moiety in the main chain of the thiol group-containing polyether polymer is 400 to 10,0.
It is preferably 00. If the molecular weight is less than 400, the effect of improving the compatibility with the plasticizer when reacted with the polysulfide polymer is small, while if it exceeds 10,000, the viscosity of the polymer becomes high, which is not preferable.

In polyether polymers containing thiol groups
S _x is preferably disulfide, and the weight ratio of S _x / mercaptan group (—CH ₂ CH (OH) CH ₂ —SH) is 1.06.
The above is preferable. The ratio of S _x / mercaptan group is
When it is less than 1.06, the proportion of polysulfide bonds is small, and the compatibility between the thiol group-containing polyether polymer and the polysulfide polymer starting material becomes insufficient, which is not preferable.

Such a thiol group-containing polyether polymer can be synthesized by utilizing a known method described in JP-B-47-48279. That is, after adding epihalohydrin such as epichlorohydrin or epibromohydrin to polyalkylene glycol such as polypropylene glycol or polyethylene glycol, MSH (where M represents an alkali metal such as Na or K) is added. Represented by sodium hydrosulfide, alkali hydrosulfide such as potassium hydrosulfide, and / or M ₂ S _x (where M is N
It is an alkali metal such as a and K, and x represents an integer of 1 to 5. ) React with alkali polysulphide such as sodium polysulphide, potassium polysulphide, etc. Thereby, for example, the following general formula: HSCH ₂ CH (OH) CH ₂ (O-CH (CH ₃ ) CH ₂ ) _n -O-CH ₂ CH (OH) CH ₂ − − [S _x -CH ₂ CH (OH ) CH _2- (O-CH (CH ₃ ) CH ₂ ) _n -O-CH ₂ CH (OH) CH ₂ ] _m SH ・ ・ ・ (3) (where n is an integer of 6 to 200 and m is 0, 1 or 2
And x is an integer of 1 to 5. A polyether polymer having a functional group represented by) is obtained.

As the above-mentioned alkali hydrosulfide (MSH),
Industrially produced flake sodium hydrosulfide is preferred. This sodium hydrosulfide has a purity of about 70% and contains a trace amount of sodium polysulfide component.

The amount of MSH and / or M ₂ S _x added is usually 1 to 50 parts by weight per 100 parts by weight of (a) + (b),
It is preferably 2 to 35 parts by weight. MSH and / or M ₂
When the amount of S _x added is less than 1 part by weight, the thiolation of the halogen-terminated prepolymer is not sufficient, and when it exceeds 50 parts by weight, the polyether polymer remarkably thickens during synthesis, which is not preferable.

In the main chain of the polyether polymer thus obtained, some polysulfide bonds (provided that S _x
Has a degree of polymerization of 1 to 5. )It is included.

Mixing ratio of polysulfide polymer starting material and thiol group-containing polyether polymer (weight ratio)
Is 95/5 to 5/95, preferably 90/10 to 10/90. If the polysulfide polymer starting material is less than 5% by weight based on the total weight, the weather resistance of the cured product will be poor. When the thiol group-containing polyether polymer is less than 5% by weight, the effect of improving the compatibility with the plasticizer is small.

The reaction conditions of (a) the polysulfide polymer according to the present invention and (b) the thiol group-containing polyether polymer are 10 to 100 ° C., preferably 20 to 80 ° C., and the mixture may be stirred for 1 to 60 minutes.

At this time, 0.
It is preferable to add 01 to 10 parts by weight of acids, if necessary, after dissolving them in a solvent such as water or ethanol.

The reaction between (a) the polysulfide polymer and (b) the thiol group-containing polyether polymer in the present invention is considered to occur as follows, for example.

[Chemical 1] By such exchange reaction of the polysulfide bond, the polyether chain is introduced into the main chain of the polysulfide polymer. that time,

[Chemical 2] A low molecular weight component represented by (q is an integer of 0 to 2 and x is an integer of 1 to 5) is produced. Therefore, in the present invention, by shifting the pH of the reaction system to the acidic side by adding an acid, the formula (5)
In the low molecular weight cyclic compound shown in (3), the cleavage of the S _x portion is promoted, the molecular weight distribution is averaged by the subsequent addition reaction, and the low molecular weight component represented by the formula (5) can be reduced to 10% or less.

Therefore, the reaction system is set to the above temperature condition (30 to 1).
When heated to 50 ° C., preferably 50 to 120 ° C., the above-mentioned by-products participate in the reaction and the amount of the by-products is reduced to 10% by weight or less. Therefore, it is possible to prevent the molecular weight distribution of the polysulfide polymer starting material from being distorted.

The second method for producing the polysulfide polyether polymer is to add the polysulfide polyether polymer to a single stage by adding the polysulfide polymer starting material in advance when the above-mentioned thiol group-containing polyether polymer is synthesized. It is produced by reaction.

In the second method, the main chain is-(R
₁ O) _n- (wherein R ₁ is an alkylene group having 2 to 4 carbon atoms,
n represents an integer of 6 to 200. ) Is added to a polyalkylene glycol such as polypropylene glycol or polyethylene glycol having two or more hydroxyl groups at the terminal and epihalohydrin such as epichlorohydrin or epibromohydrin to produce a halogen-terminated prepolymer. , The terminal is thiolated with an alkali hydrosulfide or an alkali polysulfide, in which case the general formula: HS (C ₂ H ₄ OCH ₂ O
_{C 2 H 4 S x) m} C 2 H 4 OCH 2 OC 2 H 4 SH ··· (2) ( where, x is in integer from 1 to 5, the average is about 2, m is from 1 to 50 The polysulfide polymer represented by the formula (1) is added and reacted at the same time.

In the second method, the weight ratio of halogen-terminated prepolymer to polysulfide polymer is 95.
/ 5 to 5/95, preferably 90/10 to 10/90. If the polysulfide polymer content is less than 5% by weight, the weather resistance of the resulting cured product is insufficient. When the halogen-terminated prepolymer is less than 5% by weight, the effect of improving the compatibility with the plasticizer is small.

In the second method, the halogen-terminated prepolymer is thiolated in the presence of a polysulfide polymer under the same temperature conditions as in the first method, whereby the same procedure as in the first method (4-1) And the reaction of the formula (4-2) is carried out, and further the accumulation of low molecular weight by-products as represented by the formula (5) can be prevented.

[3] Oxidizing agent As the oxidizing agent, a substance which has been conventionally used as a curing agent for a thiol group-containing polymer can be used. Specific examples of these oxidizing agents include ZnO ₂ , FeO ₂ ,
PbO ₂ , MgO ₂ , CaO ₂ , BaO ₂ , MnO ₂ , TeO ₂ , SeO ₂ , P
b ₃ O ₄ , SrO ₂ , LiO _{2 and} other inorganic peroxides, ZnO, FeO, P
Inorganic oxides such as bO, Fe ₂ O ₃ , Sb ₂ O ₃ , MgO, CoO, CaO, CuO, BaO, Na ₂ CrO ₄ , K ₂ CrO ₄ , Na ₂ Cr ₂ O ₇ , K ₂ Cr
₂ O ₇ , NaClO ₄ , NaBO ₂ · H ₂ O ₂ , K ₂ C ₂ O ₆ , KMnO ₄ , inorganic peroxidation agents such as sodium percarbonate (2Na ₂ CO ₃ + 3H ₂ O ₂ ), benzoyl peroxide, dicumyl Organic peroxides such as peroxide, cumene hydroperoxide, t-butyl hydroperoxide, t-butyl perbenzoate, sodium peracetate, urea peroxide, etc., organic oxidants such as nitrobenzene, dinitrobenzene, paraquinone dioxime, etc. , But PbO ₂ is the most widely used.

The compounding amount of these oxidizing agents varies depending on the kind of the oxidizing agent, but generally, the polysulfide polymer or the polysulfide polyether polymer 1
It is 1 to 50 parts by weight with respect to 00 parts by weight.

[4] Discoloration preventing agent (i) surfactant, (ii) unsaturated fatty acid and / or salt thereof,
And (iii) a component comprising at least one kind of aromatic amine
(C) is a substance that can be called an "anti-tarnish agent" and has the function of suppressing changes in the color tone of the cured product during outdoor exposure.

(I) Surfactant Surfactants include cationic, anionic, nonionic,
Any of the amphoteric surfactants may be used, such as an aliphatic amine salt, an aliphatic quaternary ammonium salt, an aromatic quaternary ammonium salt,
Acyl amino acid salt, acyl sulfonate, polyoxyethylene alkylamine, polyoxyethylene aliphatic amide, carboxybetaine and the like are preferable. Specific examples of such a surfactant include octadecylamine acetate,
Alkyl (C ₈ ~C ₁₈₎ trimethyl ammonium chloride, tetradecyl dimethyl benzyl ammonium chloride, lauroyl sarcosinate, acyl (C ₁₂ -C
₁₈ ) Sodium methyl taurate, polyoxyethylene dodecyl amine, dimethyl lauryl betaine and the like can be mentioned.

(Ii) Unsaturated fatty acids Examples of unsaturated fatty acids include oleic acid, linoleic acid, linolenic acid, and rosin acid. Examples of unsaturated fatty acid salts include sodium oleate, sodium linoleate, sodium linolenate, and sodium rosinate.

(Iii) Aromatic amines As aromatic amines, N, N'-diphenyl-p-phenylenediamine, N, N'-dinaphthyl-p-phenylenediamine, N-phenyl-N'-isopropyl-p- Phenylenediamine, N-phenyl-N'-1,3-dimethylbutyl-p-
Phenylenediamine, 2,2,4-trimethyl-1,2, -dihydroquinoline polymer, 6-ethoxy-2,2,4-trimethyl
-1,2, -dihydroquinoline polymer, 4-amino-5-hydroxy-2,7-naphthalene sulfonic acid and the like can be mentioned.

The blending amount of the discoloration inhibitor comprising at least one of (i), (ii) and (iii) is such that the polysulfide polymer or polysulfide polyether polymer 100 is used.
0.1 to 30 parts by weight, preferably 0.2 to 10 parts by weight
Parts by weight. If the amount of the above discoloration inhibitor is less than 0.1 part by weight, the effect of preventing discoloration during outdoor exposure is insufficient.
If it exceeds 30 parts by weight, the adhesiveness of the cured product decreases.

To the curable composition of the present invention, a filler such as calcium carbonate, talc, clay, titanium oxide or silica is added for the purpose of further improving the economical efficiency, workability and physical properties after curing. You can Further, a phthalic acid ester such as butylbenzyl phthalate (BBP) can be added to the curable composition of the present invention. Plasticizers such as chlorinated paraffin and hydrogenated terphenyl can also be added.

[0042]

The present invention will be described in more detail by the following examples.

Synthesis Example 1 Bifunctional polypropylene glycol obtained by adding propylene oxide to propylene glycol (OH value
162) 1000 g, epichlorohydrin 278.3 g, and stannic chloride pentahydrate 2.0 g were charged into a 2 liter reaction vessel,
The mixture was stirred at 100 ° C for 3 hours. Furthermore, sodium hydrosulfide (purity 70
%) 240.7 g was added, the temperature was raised to 100 ° C., and the mixture was stirred for 1.5 hours. Then, the salt was removed to obtain a pale yellow transparent liquid polymer.

300 g of the obtained polymer and 300 g of polysulfide polymer (trade name “Thiocol LP55” manufactured by Toray Thiokol Co., Ltd.) were placed in a 1 liter reaction vessel and heated and stirred at 90 ° C. for 4 hours to find that the mercaptan content was A brown transparent polymer with 3.2% by weight and a viscosity of 60 poise (25 ° C.) was obtained.

Examples 1 to 12 and Comparative Example 1 The polymer obtained in Synthesis Example 1 was mixed with a plasticizer, a filler, a colorant, a vulcanization aid, and a compound of the type and amount shown in Table 3.
(C) (discoloration preventing agent) is blended in the proportion shown in Table 1 to prepare the main agent A.
Got On the other hand, PbO ₂ (oxidizing agent), a plasticizer and a filler were blended in the proportions shown in Table 2 to obtain a curing agent A.

50 mm by mixing the main agent A and the curing agent A
It was applied on an aluminum plate having a size of 25 mm x 2 mm and exposed outdoors for 2 months to examine the presence or absence of discoloration. Further, as Comparative Example 1, the same test was carried out even when the compound (C) was not added. The results are shown in Table 4.

Table 1 Ingredients for main ingredient A 100 parts by weight of the polymer of Synthesis Example 1 Plasticizer (dioctyl phthalate) 30 parts by weight Filler (calcium carbonate) 170 parts by weight Filler (titanium oxide) 15 parts by weight Colorant (carbon) 0.5 parts by weight Vulcanization aid 0.7 parts by weight Compound (C) 0.5 to 10 parts by weight

Table 2 Compounding oxidizer (PbO ₂ ) of curing agent A 13.0 parts by weight Plasticizer (chlorinated paraffin) 7.4 parts by weight Filler (calcium carbonate) 6.6 parts by weight

[0049] Table 3 Compound kind and amount Example No. of compound of (C) kind added parts Example 1 Okuda decyl amine acetate 2 Example 2 alkyl _{(C) (C 8 ~C 18} ) Dimethylbenzyl ammonium chlorite 2 Example 3 Tetradecyl dimethyl benzyl ammonium chloride 2 Example 4 Lauroyl sarcosinate 2 Example 5 Acyl (C ₁₂ -C ₁₈ ) methyl taurate sodium 2 Example 6 Polyoxyethylene dodecylamine 2 Example 7 Dimethylalkyl (C ₁₂ -C ₁₈ ) laurylbetaine 2 Example 8 Oleic acid 10 Example 9 Linolenic acid 10 Example 10 Gumrosin 10 Example 11 Hearthol RX ^* 10 Example 12 Tetradecyldimethylbenzylbenzylammonium chloride 1 Heartol RX ^* 5 example 13 S-30 ^** 10 example 14 N, N '- Shi Naphthyl-p-phenylene diamine 0.5 Example 15 2,2,4-Trimethyl-1,2, -diethyl quinoline polymer 0.5 Example 16 4-Amino-5-human ethoxy-2,7-naphthalene sulfonic acid 0.5 Comparative Example 1 No additive- (Note) *: Harima Kasei Co., Ltd. rosin acid **: Harima Kasei Co., Ltd. sodium rosinate 30% aqueous solution

[0050] Note) ◎: No discoloration ○: Almost no discoloration △: Slight discoloration ×: Discoloration

Examples 13 to 16 and Comparative Example 2 Polysulfide polymer (manufactured by Toray Thiokol Ltd.,
Product name "Thiocol LP55"), plasticizer, filler, colorant, adhesion promoter, and compounds of the types and amounts shown in Table 7.
(C) and (C) were blended in the proportions shown in Table 5 to obtain a main agent B. On the other hand, PbO ₂ (oxidizing agent), a plasticizer, and a curing retarder were mixed in the proportions shown in Table 6 to obtain a curing agent B. The same test as in Example 1 was conducted on the composition in which the main agent B and the curing agent A were mixed. In addition, as Comparative Example 2, the same test was performed in the case where the compound (C) was not added. The results are shown in Table 8.

Table 5 Ingredient B 100 parts by weight of polysulfide polymer Plasticizer (butylbenzyl phthalate) 30 parts by weight Filler (calcium carbonate) 60 parts by weight Filler (titanium oxide) 20 parts by weight Colorant (carbon) 0.3 parts by weight Adhesion imparting agent 0.2 parts by weight Compound (C) 0.3 to 10 parts by weight

Table 6 Composition of curing agent B Oxidizing agent (PbO ₂ ) 7.5 parts by weight Plasticizer (chlorinated paraffin) 4.0 parts by weight Oxidation retarder (stearic acid) 0.5 parts by weight

[0054] Table 7 Compound kind and amount Example No. of compound (C) kind added parts by weight Example 13 Tetorate Bu mark Bu Mechiruhe Bu Nji Le ammonium chlorite Bu 2 Example 14 linolenic acid 10 Example 15 gum rosin of (C) 10 Example 16 Hartall RX ^* 10 Example 17 2,2,4-Trimethyl-1,2, -diethyl quinoline polymer 0.3 Example 18 6-Ethoxy-2,2,4-trimethyl-1,2, -Dihitroquinoline Polymer 0.5 Comparative Example 1 No Addition-

[0055] (Note) ◎: No discoloration ○: Almost no discoloration △: Slight discoloration ×: Discoloration

[0056]

EFFECTS OF THE INVENTION The curable composition of the present invention comprises a polysulfide polymer or a polysulfide polyether polymer and at least one of a predetermined amount of a surfactant, an unsaturated fatty acid and / or a salt thereof, and an aromatic amine together with an oxidizing agent. Seeds are added. Therefore, the cured product obtained therefrom has the advantage that the discoloration is extremely small even when exposed outdoors for a long period of time.

─────────────────────────────────────────────────── ─── Continuation of the front page (51) Int.Cl. ⁵ Identification code Office reference number FI technical display area C08K 5/17

Claims (2)

[Claims] 1. An amount of 1 to 50 parts by weight of (B) an oxidizing agent, (C) (i) a surfactant, (ii) an unsaturated fatty acid and / or a salt thereof, based on 100 parts by weight of (A) polysulfide polymer. , And (ii
i) A curable composition comprising 0.1 to 30 parts by weight of at least one aromatic amine. Wherein (A) in the main chain, _{(i) - (R 1 O) n} - ( where, R ₁ is an alkylene group having 2 to 4 carbon atoms, n represents 6-200
Indicates an integer. ) Polyether part represented by
_{(B) - (C 2 H 4 OCH} 2 OC 2 H 4 -S x) -, and _{- (CH 2 CH (OH)} CH 2 -S x) - ( here, x is an integer of 1 to 5. ) And a terminal at the end, (C) -C ₂ H ₄ OCH ₂ OC ₂ H ₄ -SH
And / or -CH ₂ CH (OH) CH ₂ -SH with respect to 100 parts by weight of a polysulfide polyether polymer having a thiol group, (B) an oxidizing agent 1 to 50
At least 1 part by weight of (C) (i) surfactant, (ii) unsaturated fatty acid and / or salt thereof, and (iii) aromatic amine
A curable composition comprising 0.1 to 30 parts by weight of a seed.