JPH06192380A - Polyurethaneurea elastomer - Google Patents

Abstract

PURPOSE:To obtain the subject elastomer useful for industrial rolls, belts, parts, etc., and excellent in resilience and bending characteristics by reacting a specific polyisocyanate with an amine.polyol. CONSTITUTION:This elastomer is obtained by reacting (A) a polyisocyanate component obtained by reacting 1,5-naphthalene diisocyante with a polyol of formula I (R<1> is divalent polyalkylene polyether or polyalkylene polyester which may contain an unsaturated bond and has 650-5000, preferably 800-4000 molecular weight) with (B) an aminepolyol consisting of (i) an amine compound of formula II (R is R<1> and has >=200 molecular weight), (ii) an aromatic diamine and (iii) a polyol. Furthermore, amount ratios of these components (B) (i) to (iii) is expressed by the following formulas: (ii)/(i+ii)=0-0.5 and (M)/(i+ii+ iii)=0.05-0.95.

Description

Detailed Description of the Invention

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a polyurethane urea elastomer having excellent impact resilience and bending properties, which is useful for low hardness industrial rolls, belts, blankets or industrial parts.

[0002]

2. Description of the Related Art Up to now, the present inventors have filed Japanese Patent Application No. 4-19.
Japanese Patent No. 7501 proposes a polyurethane urea elastomer obtained by using a polyisocyanate component obtained by reacting amines, 1,5-naphthalene diisocyanate and a polyol.

However, the polyurethaneurea elastomer described in the above specification has a high hardness while maintaining excellent static properties and excellent impact resilience and bending properties. It was difficult to apply to low hardness industrial rolls, belts, blankets or industrial parts.

[0004]

DISCLOSURE OF THE INVENTION The present invention provides a polyurethane urea elastomer having a low hardness while maintaining good static physical properties and having excellent dynamic physical properties such as impact resilience and bending properties. Is provided.

[0005]

[Means for Solving the Problems] The inventors of the present invention have conducted extensive studies to solve the above-mentioned problems, and particularly not only the polyisocyanate component using 1,5-naphthalene diisocyanate and the amine compound Furthermore, when a polyol was also reacted with the amine / polyol component to be used, a polyurethane urea elastomer having a low hardness while having surprisingly good static physical properties and excellent impact resilience and bending properties was obtained. The present invention has been completed based on these findings.

That is, the present invention relates to 1,5-naphthalene diisocyanate and

[0007]

[Chemical 3] (In the formula, R ¹ represents a polyalkylene polyether or a polyalkylene polyester having an average molecular weight of 650 to 5000, which may be divalent and may contain an unsaturated bond.)

A polyisocyanate component obtained by reacting a polyol represented by

(A)

[0010]

[Chemical 4] (In the formula, R represents a divalent, polyalkylene polyether or polyalkylene polyester having an average molecular weight of 200 or more, which may contain an unsaturated bond.)

Amine compound represented by (B) Aromatic diamine (C) Amine-polyol component consisting of polyol represented by (formula 3) (provided that (A),
The weight ratio of (B) and (C) is (B) / [(A) + (B)].
= 0 to 0.5, and (C) / [(A) + (B) +
(C)] = 0.05 to 0.95. }

The present invention provides a polyurethane urea elastomer obtained by reacting with.

The polyurethaneurea elastomer of the present invention can be usually produced by the following method.

That is, a predetermined amount of aromatic diamine (B) is mixed with amine compound (A), heated and completely dissolved, and then a predetermined amount of polyol (C) is mixed, and the mixed solution is mixed with 10 After sufficiently defoaming under a reduced pressure of 20 mmHg, cooling to room temperature and amine / polyol component [(A) + (B) +
(C)] is obtained. Then, the obtained amine / polyol component [(A) + (B) + (C)] is added to a predetermined polyisocyanate component prepared by using 1,5-naphthalene diisocyanate (NDI) and sufficiently added. After mixing, the mixture is degassed, poured into a mold previously heated to 80 to 120 ° C., and cured at that temperature for several tens of minutes. After that, the molded product is removed from the mold and after-cured in an oven set at 100 ° C to 150 ° C. Further, it is aged for 1 week at room temperature to obtain the desired polyurethane urea elastomer.

The polyisocyanate component used in the production of the polyurethaneurea elastomer of the present invention is obtained by reacting 1,5-naphthalene diisocyanate (NDI) and a polyol represented by the chemical formula (3) in a predetermined amount. A reaction product having an isocyanate group at both ends and chain-extended by a urethane bond can be mentioned.

Here, as the polyol used in the preparation of the polyisocyanate component used in the production of the polyurethane urea elastomer of the present invention, there can be mentioned the polyol represented by the chemical formula (3).

Examples of such polyols include aliphatic polyester glycols such as polyethylene adipate, polybutylene adipate and polypropylene adipate obtained by condensing aliphatic glycol with dicarboxylic acid to extend the chain length, ethylene oxide, propylene oxide. , Polyalkylene polyether glycols such as polyethylene ether glycol, polypropylene ether glycol, tetramethylene ether glycol and the like obtained by ring-opening polymerization of tetrahydrofuran, ε
-A polyester glycol or polybutadiene obtained by ring-opening polymerization of caprolactone having a hydroxyl group at the terminal group, and a copolymer of two or more alkylene oxides.
Mention may be made of long chain diols such as copolymers of one or more glycols and dicarboxylic acids and mixtures of aromatic glycols.

The average molecular weight of the polyalkylene polyether moiety or polyalkylene polyester moiety [R ^{1 in} the formula (Chemical Formula 3)] at the center of these compounds is 650 to 5
000, preferably 800 to 4000.

In the preparation of the polyisocyanate component used in the production of the polyurethane urea elastomer of the present invention, 1,5-naphthalene diisocyanate and (Chemical Formula 3)
The ratio of the polyol represented by is usually a molar ratio of an isocyanate group (-NCO) and a hydroxyl group (-OH), that is, a value of -NCO / -OH is 1.1 to 5.0, preferably 2.8 to. The range is 4.3.

When this value is 1.1 or less, the viscosity of the obtained polyisocyanate component becomes too high and becomes extremely viscous, which makes it difficult to handle in the subsequent operations, which is not preferable, and when it is 5.0 or more. Is not preferable because the polyisocyanate component obtained has a high freezing point, which also makes it difficult to handle in the subsequent operations.

Specific examples of the amine compound (A) represented by the chemical formula 4 used for constituting the amine / polyol component used in the production of the polyurethaneurea elastomer of the present invention include polyethylene ether glycol bis ( 4-aminobenzoate), polytetramethylene ether glycol bis (4-aminobenzoate), polypropylene ether glycol bis (4-aminobenzoate), poly (oxyethylene-propylene ether) glycol bis (4-aminobenzoate), polybutylene ether Examples include glycol bis (4-aminobenzoate) and the like.

The average molecular weight of the polyalkylene polyether moiety or polyalkylene polyester moiety [R in the formula of (Chemical Formula 4)] in the central portion of these compounds falls within the range of 200 or more.

The amine used for constituting the amine / polyol component in the production of the polyurethaneurea elastomer of the present invention may be not only the amine compound (A) alone but also the aromatic diamine (B). it can.

The aromatic diamine (B) used for this purpose may have any substituent such as a halogen atom, an alkyl group, a trifluoromethyl group or an alkoxycarbonyl group introduced into its aromatic ring.

Examples of such aromatic diamine (B) include the following (Chemical Formula 5)

[0026]

[Chemical 5] (In the formula, X and Y each independently represent a halogen atom, an optionally branched alkyl group, a trifluoromethyl group, an alkoxycarbonyl group, or a hydrogen atom, and n and m each independently represent an integer of 1 to 4. Where n and / or m is 2
In the above case, X and / or Y may independently be the same or different. )

A diaminodiphenylmethane-based aromatic diamine represented by the following (Chemical Formula 6)

[0028]

[Chemical 6] {In the formula, A is

[0029]

[Chemical 7] (In the formula, n ′ represents an integer of 1 to 4.)

A group represented by, or

[0031]

[Chemical 8] (In the formula, n ′ has the same meaning as described above.)

And X, Y, n and m have the same meanings as described above, and when n and / or m is 2 or more, X and / or Y are independently the same or different. May be. }

Or (Chem. 9)

[0034]

[Chemical 9] (In the formula, R ′ represents a lower alkyl group which may be branched,
n "represents an integer of 1 to 3, and X has the same meaning as above.)

Examples thereof include aminobenzoic acid ester-based aromatic diamines represented by:

Specific examples of the diaminodiphenylmethane-based aromatic diamine represented by the chemical formula 5 are 4,4 '.
-Methylenebisaniline, 4,4'-methylenebis (2
-Chloroaniline), 4,4'-methylenebis (2,3
-Dichloroaniline) (TCDAM), 4,4'-methylenebis (2,5-dichloroaniline), 4,4'-methylenebis (2-methylaniline), 4,4'-methylenebis (2-ethylaniline), 4 , 4'-methylenebis (2-isopropylaniline), 4,4'-methylenebis (2,6-dimethylaniline), 4,4'-methylenebis (2,6-diethylaniline), 4,4'-methylenebis (2 -Ethyl-6-methylaniline), 4,
4'-methylenebis (2-chloro-6-methylaniline), 4,4'-methylenebis (2-chloro-6-ethylaniline), 4,4'-methylenebis (3-chloro-)
2,6-diethylaniline), 4,4′-methylenebis (2-trifluoromethylaniline), 4,4′-methylenebis (2-methoxycarbonylaniline), etc.
Specific examples of the aminobenzoic acid ester-based aromatic diamine represented by the chemical formula 6 are 1,3-propanediol bis (4-aminobenzoate) and 1,4-butanediol bis (4-aminobenzoate). ), Diethylene glycol bis (4-aminobenzoate), triethylene glycol bis (4-aminobenzoate), etc.
Specific examples of the aminobenzoic acid ester-based aromatic diamine represented by Chemical formula 9 include isopropyl 4-chloro-3,5-diaminobenzoate, isobutyl 4-chloro-3,5-diaminobenzoate, and the like. Can be mentioned respectively.

Further, these aromatic diamines alone are
Alternatively, two or more kinds can be used as the aromatic diamine (B).

When the amine compound (A) and the aromatic diamine (B) are used as the amine used for constituting the amine-polyol component used in the production of the polyurethane urea elastomer of the present invention, the ratio is desired physical properties. , The relative relationship between the weights of (A) and (B), but the value of (B) / [(A) + (B)] is usually 0.5 or less, that is, (B) / ( The value of A) is 1.0
The following may be satisfied, and preferably (B) / [(A) +
The value of (B)] is 0.3 or less, that is, the value of (B) / (A) is 0.429 or less.

The value of (B) / [(A) + (B)] is 0.5.
If it exceeds, the mixed solution when the amine compound (A) and the aromatic diamine (B) are mixed becomes difficult to maintain the liquid state, and even if the liquid state is maintained, the viscosity is high and the handling and molding work becomes difficult. , At the time of molding, the pot life becomes short and a molded product may not be obtained.

In order to constitute the amine / polyol component used in the production of the polyurethaneurea elastomer of the present invention, the amine [(A) + having the above weight ratio is used.
Examples of the polyol (C) used together with (B)] include
Described in the description of the preparation of the isocyanate component (Chemical Formula 3)
The same as the polyol represented by can be mentioned.

Examples of such polyol (C) include aliphatic polyester glycols such as polyethylene adipate, polybutylene adipate, polypropylene adipate, etc. obtained by condensing aliphatic glycol with dicarboxylic acid to extend the chain length, and ethylene oxide. Polyethylene polyether glycols such as polyethylene ether glycol, polypropylene ether glycol, tetramethylene ether glycol obtained by ring-opening polymerization of propylene oxide, tetrahydrofuran, etc., and terminals of polyester glycol and polybutadiene obtained by ring-opening polymerization of ε-caprolactone A hydroxyl group, a copolymer of two or more alkylene oxides, a copolymer of two or more glycols and a dicarboxylic acid, and an aromatic group It may be mentioned long-chain diols such as a mixture of the call.

The average molecular weight of the polyalkylene polyether moiety or polyalkylene polyester moiety [R ^{1 in} the formula of (Chemical Formula 3)] at the center of these compounds used as the polyol (C) is 650 to 5000, preferably 800. The range is up to 4000.

In order to constitute the amine / polyol component used in the production of the polyurethaneurea elastomer of the present invention, the amine [(A) + having the above weight ratio is used.
The ratio of the polyol (C) used together with (B)] is
Depending on the desired physical properties, workability, etc., (A),
Relative relationship between weights of (B) and (C) (C) / [(A) +
The value of (B) + (C)] is usually 0.05 to 0.95, that is, the value of (C) / [(A) + (B)] is 0.053 to
19, preferably (C) / [(A) + (B) +
The value of (C)] is 0.1 to 0.9, that is, (C) /
The value of [(A) + (B)] is 0.11 to 9, and more preferably the value of (C) / [(A) + (B) + (C)] is 0.3 to 0.9. , That is, (C) / [(A) + (B)]
Has a value of 0.429-9.

When the value of (C) / [(A) + (B) + (C)] is within the above range, the viscosity of the amine-polyol component obtained is low, so that the workability is good and the final The hardness and physical properties of the elastomer obtained in this way meet this purpose, but if it is less than 0.05, not only the hardness of the polyurethaneurea elastomer finally obtained cannot be lowered, but also when the amine / polyol component obtained is at a low temperature. The viscosity becomes too high and the workability becomes poor, and when it exceeds 0.95, the physical properties of the finally obtained polyurethane urea elastomer deteriorate.

In the production of the polyurethaneurea elastomer of the present invention, the ratio of the isocyanate component and the amine / polyol component is usually an isocyanate group (--NC).
And O), amino group (-NH ₂₎ and the molar ratio of a hydroxyl group (-OH), a namely -NCO / (- 0.9 to 1.5 as the value of the NH ₂ + -OH), preferably 1.0 The range is from to 1.3.

Further, in the polyurethane urea elastomer of the present invention, an antioxidant, an ultraviolet absorber, an anti-coloring agent, an anti-hydrolysis agent, an anti-bacterial agent, a flame retardant, which are usually used for polyurethane elastomers, etc. depending on the application. Colorants,
A filler and the like can be added as appropriate.

The amine compound represented by the formula (4) used in the production of the polyurethane urea elastomer of the present invention is synthesized by the method described in JP-B-60-32641 and JP-A-56-135514. You can

That is, the amine compound represented by the chemical formula 4 is

[0049]

[Chemical 10] (In the formula, R has the same meaning as described above.)

The polyol compound represented by
-Nitrobenzoyl chloride is reacted in the presence of a dehydrochlorinating agent, and the resulting nitro compound is reduced by a conventional method.

The amine compound represented by (Chemical formula 4) is equivalent to the polyol compound represented by the above (Chemical formula 10) by 2 equivalents of p.
It can also be produced by a transesterification reaction of an aminobenzoic acid alkyl ester, and in this reaction, an aminobenzoic acid and an aliphatic polyol compound can be used instead of the aminobenzoic acid alkyl ester.

In these reactions, a hydroxyl group may remain at a part of the terminal by changing the reaction conditions, the molar ratio of the raw materials, etc., but it may be used as it is.

The polyol compound represented by the chemical formula 10 is, for example, an aliphatic polyester such as polyethylene adipate, polybutylene adipate or polypropylene adipate obtained by condensing an aliphatic glycol with a dicarboxylic acid to extend the chain length. Polyethylene polyether glycols such as glycols, ethylene oxide, propylene oxide and tetrahydrofuran obtained by ring-opening polymerization, polypropylene ether glycol, tetramethylene ether glycol and other polyalkylene polyether glycols, polyester glycol obtained by ring-opening polymerization of ε-caprolactone Or a polybutadiene in which the terminal group is hydroxylated, a copolymer of two or more alkylene oxides, and a copolymer of two or more glycols and a dicarboxylic acid And long-chain diols such as a mixture of aromatic glycols and the like.

[0054]

EFFECT OF THE INVENTION The polyurethane urea elastomer of the present invention has good static physical properties and also has excellent dynamic physical properties such as impact resilience and bending properties.
It has low hardness, especially polyisocyanate component using 1,5-naphthalene diisocyanate, and amine using not only amine compound but also polyol.
By reacting with a polyol component, it can be easily produced with good workability.

Therefore, the polyurethane urea elastomer of the present invention is most suitable for low hardness industrial rolls, belts, blankets or industrial parts.

[0056]

EXAMPLES The present invention will be described in detail below with reference to examples and examples.

First, the synthesis of the amine compound represented by the chemical formula 4 will be described.

Reference Example 1 Polytetramethylene ether glycol 9 having an average molecular weight of 970 was placed in a 5 l four-necked flask equipped with a thermometer, a cooling tube, a dropping funnel and a stirrer.
70 g (1.0 mol), triethylamine 242.5 g
(2.4 mol) and 1 l of toluene were charged. On the other hand, p-nitrobenzoyl chloride 390 g (2.1
(Mol) was dissolved in 1 l of toluene to prepare a dropping solution. The above reaction liquid was heated to 40 to 50 ° C. under stirring, and the dropping solution prepared above was added dropwise over 1 hour. After completion of the dropping, the reaction solution was heated and heated, and an aging reaction was carried out under reflux for 1.5 hours. After allowing to cool, the reaction solution was filtered to remove the precipitated triethylamine hydrochloride. The filtrate was washed with 5% aqueous potassium carbonate solution and water, and concentrated under reduced pressure to obtain a dinitro intermediate as a yellow transparent viscous liquid. Yield 121
The amount was 7.5 g, and the yield was 96.0%.

Then, in a 10 l four-necked flask equipped with a thermometer, a cooling tube, a dropping funnel and a stirrer, iron powder 61
4 g (11.0 mol), 30 g of acetic acid as a catalyst, and 2.5 l and 1 l of toluene and water, respectively, were charged. On the other hand, the intermediate nitro compound obtained by the above reaction was dissolved in 1 l of toluene to prepare a dropping solution. The reaction solution is heated in an oil bath and refluxed with stirring, and the dropping solution is added to 1.5
Dropped over time. After the dropping was completed, the reaction was completed by aging for 5 hours at the same temperature. Next, sodium hydrogencarbonate was added to the obtained reaction mixture to neutralize acetic acid, and the mixture was filtered while hot to remove iron sludge, and water was separated by liquid separation. The filtrate was washed with water and concentrated under reduced pressure to obtain the target polytetramethylene ether glycol bis (4-aminobenzoate).

The object product was a pale yellowish brown transparent viscous liquid, and the yield was 1078.7 g, and the yield was 93.0%. The amine value is 89.0KOHmg / g and the OH value is 2.3KOHmg.
It was / g.

Reference Example 2 Polytetramethylene ether glycol having an average molecular weight of 970 was placed in a 1 liter four-necked flask equipped with a thermometer, a water separator equipped with a cooling tube and a stirrer.
194 g (0.2 mol), ethyl p-aminobenzoate
65.9 g (0.4 mol), tetrabutyl titanate
0.018 g was charged. The reaction solution was heated to 200 ° C. with stirring under a nitrogen stream to distill off ethyl alcohol. Ethyl alcohol distilled out was 82% of the theoretical amount. After further raising the temperature to 215 ° C. and aging for 2 hours,
The pressure was reduced and the unreacted ethyl p-aminobenzoate was distilled off to obtain the desired polytetramethylene ether glycol bis (4-aminobenzoate).

The target product is a brown viscous liquid, and the yield is 224.
7 g, the yield was 93.0%. The amine value is 8
The KOH value was 1.4 KOHmg / g and the OH value was 14.5 KOHmg / g.

Next, the production of the polyurethaneurea elastomer of the present invention will be described.

Example 1 A 500 ml separable flask equipped with a thermometer and a stirrer was charged with 100 parts by weight of polytetramethylene ether glycol having an average molecular weight of 1942. The mixture was heated to 120 ° C. with stirring and the pressure was reduced to 1 mm under a reduced pressure of 5 mmHg. Dehydrated for hours. The above reaction liquid was cooled to 100 ° C, 30 parts by weight of 1,5-naphthalene diisocyanate was charged while blowing nitrogen, and the reaction was carried out at 125 ° C for about 20 minutes, followed by defoaming while cooling to 90 ° C. An isocyanate component was obtained. NC of the obtained polyisocyanate component
The O content was 5.9% by weight.

Then, the polytetramethylene ether glycol bis (4-aminobenzoate) obtained in Reference Example 1 was used.
65.4 parts by weight of polytetramethylene ether glycol having an average molecular weight of 1942 was mixed with 65.4 parts by weight by heating, degassed, and cooled to room temperature. This amine / polyol component was mixed with the polyisocyanate component obtained previously [-
_{NCO / (- NH 2 + -OH} ) = 1.05 ]. Then
The obtained mixed liquid was degassed, poured into a mold preheated to 100 ° C., cured in 15 minutes, and demolded. Then, after after-curing for 8 hours in a forced draft oven set at 120 ° C., the mixture was aged at room temperature for 1 week to obtain a polyutan urea elastomer.

The physical properties and composition of the polyutan urea elastomer thus obtained are shown in (Table 1).

The physical properties were measured according to JIS K 6301. Further, the de-matcher measurement was performed by inserting a notch, and indicated by the number of times of bending at which the crack reached 100% due to bending.

Example 2 A polyurethaneurea elastomer was obtained in the same manner as in Example 1, except that the polytetramethylene ether glycol bis (4-aminobenzoate) obtained in Reference Example 2 was used instead of the amine compound in Example 1. .

The mixing conditions such as the mixing temperature of the amine / polyol component and the isocyanate component, and -NCO
/ - the value of (NH ₂ + -OH), curing temperature, curing time, after-curing temperature, curing conditions such as after-curing time was performed under the same conditions as in Example 1.

The physical properties and composition of the polyurethane urea elastomer thus obtained are shown in (Table 1).

(Example 3) A polyurethane urea elastomer was obtained in the same manner as in Example 1, except that the ratio of the polyol in the amine / polyol component of Example 1 was changed.

The mixing conditions such as the mixing temperature of the amine / polyol component and the isocyanate component, and -NCO /
The value of (-NH ₂ + -OH), curing temperature, curing time, after-curing temperature, curing conditions such as after-curing time was performed under the same conditions as in Example 1.

The physical properties and composition of the polyurethane urea elastomer thus obtained are shown in (Table 1).

(Example 4) 4,4'-methylenebis (2-chloro) was added to 100 parts by weight of the polytetramethylene ether glycol bis (4-aminobenzoate) obtained in Reference Example 1 instead of the amine compound of Example 1. Aniline)
Using an amine liquid mixed at a ratio of 11.1 parts by weight,
A polyurethaneurea elastomer was obtained in the same manner as in Example 1.

The mixing conditions such as the mixing temperature of the amine / polyol component and the isocyanate component, and -NCO
/ - the value of (NH ₂ + -OH), curing temperature, curing time, after-curing temperature, curing conditions such as after-curing time was performed under the same conditions as in Example 1.

The physical properties and composition of the polyurethane urea elastomer thus obtained are shown in (Table 1).

Comparative Example 1 Polyurethane was prepared in the same manner as in Example 1 except that the polytetramethylene ether glycol bis (4-aminobenzoate) obtained in Reference Example 1 was used instead of the amine / polyol component of Example 1. A urea elastomer was obtained.

The mixing conditions such as the mixing temperature of the amine / polyol component and the isocyanate component, and -NCO
/ - the value of (NH ₂ + -OH), curing temperature, after-curing temperature, curing conditions such as after-curing time Example 1
The same conditions were used, but the curing time was 15 minutes.

The physical properties and composition of the polyurethane urea elastomer thus obtained are shown in (Table 1).

Comparative Example 2 A polyurethane urea elastomer was obtained in the same manner as in Comparative Example 1 except that the amount of 1,5-naphthalene diisocyanate in the polyisocyanate component of Comparative Example 1 was changed.

The mixing conditions such as the mixing temperature of the amine / polyol component and the isocyanate component, and -NCO /
The value of (-NH ₂ + -OH), curing temperature, curing time, after-curing temperature, curing conditions such as after-curing time was performed under the same conditions as in Example 1.

The physical properties and composition of the polyurethane urea elastomer thus obtained are shown in (Table 1).

[0083]

[Table 1]

Example 5 A polyurethaneurea elastomer was prepared in the same manner as in Example 1 except that polytetramethylene ether glycol having an average molecular weight of 970 was used instead of the polytetramethylene ether glycol in the amine / polyol component of Example 1. Got

The mixing conditions such as the mixing temperature of the amine / polyol component and the isocyanate component, and -NCO
/ - the value of (NH ₂ + -OH), curing temperature, curing time, after-curing temperature, curing conditions such as after-curing time was performed under the same conditions as in Example 1.

The physical properties and composition of the polyurethane urea elastomer thus obtained are shown in (Table 2).

Example 6 As in Example 1, poly (3-methylpentamethylene) glycol adipate having an average molecular weight of 1941 was used instead of polytetramethylene ether glycol in the amine / polyol component of Example 1. To obtain a polyurethane urea elastomer.

The mixing conditions such as the mixing temperature of the amine / polyol component and the isocyanate component, and -NCO
/ - the value of (NH ₂ + -OH), curing temperature, curing time, after-curing temperature, curing conditions such as after-curing time was performed under the same conditions as in Example 1.

The physical properties and composition of the polyurethane urea elastomer thus obtained are shown in (Table 2).

Example 7 As in Example 1, poly (3-methylpentamethylene) glycol adipate having an average molecular weight of 1941 was used in place of polytetramethylene ether glycol in the polyisocyanate component of Example 1. To obtain a polyurethane urea elastomer.

The mixing conditions such as the mixing temperature of the amine / polyol component and the isocyanate component, and -NCO
The curing conditions such as the value of / (-NH ₂ + -OH), curing temperature, curing time, after-cure temperature, after-cure time, etc. were the same as in Example 1.

The physical properties and composition of the polyurethane urea elastomer thus obtained are shown in (Table 2).

(Example 8) Instead of polytetramethylene ether glycol in the polyisocyanate component of Example 1, poly (3-methylpentamethylene) glycol adipate having an average molecular weight of 1941 was used, and A polyurethaneurea elastomer was obtained in the same manner as in Example 1 except that the amount of 1,5-naphthalene diisocyanate in the isocyanate component was changed.

The mixing conditions such as the mixing temperature of the amine / polyol component and the isocyanate component, and -NCO
The curing conditions such as the value of / (-NH ₂ + -OH), curing temperature, curing time, after-cure temperature, after-cure time, etc. were the same as in Example 1.

The physical properties and composition of the polyurethane urea elastomer thus obtained are shown in (Table 2).

[0096]

[Table 2]

Claims (1)

[Claims] 1. A 1,5-naphthalene diisocyanate and (In the formula, R ¹ represents a polyalkylene polyether or polyalkylene polyester having an average molecular weight of 650 to 5000, which may be divalent and may contain an unsaturated bond.) Polyisocyanate obtained by reacting with a polyol represented by Ingredients and (A) (In the formula, R represents a polyalkylene polyether or polyalkylene polyester having an average molecular weight of 200 or more, which may have a divalent unsaturated bond.) Amine compound (B) Aromatic diamine (C) Amine / polyol component consisting of polyol represented by 1) (however, (A),
The weight ratio of (B) and (C) is (B) / [(A) + (B)].
= 0 to 0.5, and (C) / [(A) + (B) +
(C)] = 0.05 to 0.95. } The polyurethane urea elastomer obtained by making it react with.