CA1225393A - Low-temperature resistance improver for rubber - Google Patents
Low-temperature resistance improver for rubberInfo
- Publication number
- CA1225393A CA1225393A CA000444248A CA444248A CA1225393A CA 1225393 A CA1225393 A CA 1225393A CA 000444248 A CA000444248 A CA 000444248A CA 444248 A CA444248 A CA 444248A CA 1225393 A CA1225393 A CA 1225393A
- Authority
- CA
- Canada
- Prior art keywords
- rubber
- acid
- alcohol
- ester
- improver according
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
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- Compositions Of Macromolecular Compounds (AREA)
Abstract
Abstract of the Disclosure A low-temperature resistance improver for rubber essentially consists or an ester derived from an unsaturated fatty acid and at least one hydroxyl compound selected from the group consisting of satu-rated alcohols, unsaturated alcohols and glycols.
Description
3~3~
The present invention relates to a low-temperature resistance imp prover for rubber and more particularly to a low-temperature resistance improver for rubber which improves not only the low temperature resistance of rubber but also its heat resistance and other physical and chemical characteristics.
With an increase in the range of the application and the use of rubber goods in recent years, improved low-temperature resistance, particularly low-temperature flexibility superior to that of conventional rubber goods are required. Therefore, studies to improve the low-temperature resistance by, for example, blending different rubbers with each other or adding a third component have been made with considerable success. However, these methods have both merits and demerits and no decisive method has yet been found.
For example, there is a method wherein natural rubber (hereinafter referred to as NO) or polybutadiene rubber (hereinafter referred to as BY), which are thought to have relatively good low-temperature resistance, is blended with acrylonitrile/butadiene rubber (hereinafter referred to as NOR) or sheller-prone rubber (hereinafter referred to as OR), which both have poor low-tempera-lure resistance, to improve the low-temperature resistance of NOR or CR.
However, since a large quantity of NO or BY must be blended to improve the no-distance sufficiently, and there is a problem in compatibility between rubbers, physical and chemical characteristics peculiar to NOR or OR often deteriorate as a result. In a method for improving low-temperature resistance by blending different rubbers, it is scarcely possible to improve the low-temperature no-distance of NO or styrene/butadiene rubber (hereinafter called as SIR).
A third component may be added. Ductile subacute (hereinafter referred to as DOS), diisobutyl adipate (hereinafter referred to as DIVA) and trioctyl phosphate are known as additives for OR and SIR, and dibutyl subacute and DOS are known as additives for OR and NOR. However, improvement in low-I
temperature resistance is not sufficient. Therefore additives combining superior low-temperature resistance with excellent heat resistance and other physical and chemical characteristics are required in some fields. As an example bottle owlet has considerably good low-temperature resistance but is very poor in heat resistance. No low-temperature resistance improver satisfy-in all the characteristics has been found.
We have made studies to find out an agent for improving the low-temperature resistance of rubber as well as its heat resistance and other various characteristics, and have surprisingly found that when a specified Lo ester compound having a structure very close to that of known additives is added to rubber, there can be obtained a rubber having excellent properties, unattainable by known additives, such as satisfactory low-temperature resist-ante, heat resistance and other physical and chemical characteristics. The present invention is based on this finding.
According to one aspect of the present invention there is provided a low-temperature resistance improver for rubber, comprising an ester derived from an unsaturated Patty acid having 12 to I carbon atoms and at least one hydroxyl compound selected from the group consisting of saturated alcohols having 6 to 12 carbon atoms, unsaturated alcohols having 14 to 18 carbon atoms and glycols having 2 to 6 carbon atoms.
According to another aspect of the present invention there is provide Ed a rubber comprising the above improver.
Examples of the saturated alcohols having 6 to 12 carbon atoms used in the present invention include Huxley alcohol, 2-ethylhexyl alcohol, n-octyl alcohol, n-decyl alcohol, and laurel alcohol. Preferred alcohols are those having 8 to 10 carbon atoms.
Examples of the unsaturated alcohols having 14 to 18 carbon atoms include myristoleyl alcohol and oilily alcohol.
The present invention relates to a low-temperature resistance imp prover for rubber and more particularly to a low-temperature resistance improver for rubber which improves not only the low temperature resistance of rubber but also its heat resistance and other physical and chemical characteristics.
With an increase in the range of the application and the use of rubber goods in recent years, improved low-temperature resistance, particularly low-temperature flexibility superior to that of conventional rubber goods are required. Therefore, studies to improve the low-temperature resistance by, for example, blending different rubbers with each other or adding a third component have been made with considerable success. However, these methods have both merits and demerits and no decisive method has yet been found.
For example, there is a method wherein natural rubber (hereinafter referred to as NO) or polybutadiene rubber (hereinafter referred to as BY), which are thought to have relatively good low-temperature resistance, is blended with acrylonitrile/butadiene rubber (hereinafter referred to as NOR) or sheller-prone rubber (hereinafter referred to as OR), which both have poor low-tempera-lure resistance, to improve the low-temperature resistance of NOR or CR.
However, since a large quantity of NO or BY must be blended to improve the no-distance sufficiently, and there is a problem in compatibility between rubbers, physical and chemical characteristics peculiar to NOR or OR often deteriorate as a result. In a method for improving low-temperature resistance by blending different rubbers, it is scarcely possible to improve the low-temperature no-distance of NO or styrene/butadiene rubber (hereinafter called as SIR).
A third component may be added. Ductile subacute (hereinafter referred to as DOS), diisobutyl adipate (hereinafter referred to as DIVA) and trioctyl phosphate are known as additives for OR and SIR, and dibutyl subacute and DOS are known as additives for OR and NOR. However, improvement in low-I
temperature resistance is not sufficient. Therefore additives combining superior low-temperature resistance with excellent heat resistance and other physical and chemical characteristics are required in some fields. As an example bottle owlet has considerably good low-temperature resistance but is very poor in heat resistance. No low-temperature resistance improver satisfy-in all the characteristics has been found.
We have made studies to find out an agent for improving the low-temperature resistance of rubber as well as its heat resistance and other various characteristics, and have surprisingly found that when a specified Lo ester compound having a structure very close to that of known additives is added to rubber, there can be obtained a rubber having excellent properties, unattainable by known additives, such as satisfactory low-temperature resist-ante, heat resistance and other physical and chemical characteristics. The present invention is based on this finding.
According to one aspect of the present invention there is provided a low-temperature resistance improver for rubber, comprising an ester derived from an unsaturated Patty acid having 12 to I carbon atoms and at least one hydroxyl compound selected from the group consisting of saturated alcohols having 6 to 12 carbon atoms, unsaturated alcohols having 14 to 18 carbon atoms and glycols having 2 to 6 carbon atoms.
According to another aspect of the present invention there is provide Ed a rubber comprising the above improver.
Examples of the saturated alcohols having 6 to 12 carbon atoms used in the present invention include Huxley alcohol, 2-ethylhexyl alcohol, n-octyl alcohol, n-decyl alcohol, and laurel alcohol. Preferred alcohols are those having 8 to 10 carbon atoms.
Examples of the unsaturated alcohols having 14 to 18 carbon atoms include myristoleyl alcohol and oilily alcohol.
-2-Examples of the glycols having 2 to 6 carbon atoms include ethylene glycol, propylene glycol, diethylene glycol, neopentyl glycol, butanediol, and hexanediol.
Examples of the unsaturated fatty acid having 12 to 24 carbon atoms used in the present invention include lauroleic acid, oleic acid, elaidic acid, erucic acid, linoleic acid, linoelaidic acid, eleostearic acid, myristoleic acid, linolenic acid and tall oil fatty acid which is a mixture of the above-listed acids. Among these acids, oleic acid and tall oil fatty acid are preferred.
LO The esters of the present invention may be prepared from the above described hydroxyl compounds and unsaturated fatty acids by any of conventional methods. For example, they can be prepared by a dehydration-
Examples of the unsaturated fatty acid having 12 to 24 carbon atoms used in the present invention include lauroleic acid, oleic acid, elaidic acid, erucic acid, linoleic acid, linoelaidic acid, eleostearic acid, myristoleic acid, linolenic acid and tall oil fatty acid which is a mixture of the above-listed acids. Among these acids, oleic acid and tall oil fatty acid are preferred.
LO The esters of the present invention may be prepared from the above described hydroxyl compounds and unsaturated fatty acids by any of conventional methods. For example, they can be prepared by a dehydration-
3-~.2~6~
condensation reaction between the hydroxyl compounds and the unsaturated fatty acids or an ester exchange reaction between the hydroxyl compounds and lower alkyd esters of the unsaturated fatty acids.
Examples of the esters suitable for use in -the present invention include octal owlet, decal owlet, tall oil fatty acid octal ester, oilily owlet, ethylene glycol dwelt, 1,4-butanediol dwelt, 1,6-hexanediol dwelt, 2-ethylhexyl owlet, dodecyl owlet, decal myristoleate, and oilily myristoleate, among which octal owlet is preferred.
By adding the low-temperature resistance it prover of the present invention to rubber, the low-temperature resistance can be greatly improved while other physical properties, particularly heat resistance, can be maintained or improved.
Though it is not clear why the low-temperature resistance improver of the present invention is superior to conventional compounds, it is thought to be Sue to wits chemical structure such as alkyd chain length, ester linkage, or unsaturated bond.
In any case, the improver of the present invention must be an ester derived from the hydroxyl compound and the unsaturated fatty acid as specified above.
The effect of the present invention can not be obtained _ _ ? Fly t`'' ~"~,~ 9~9~3 by an ester derived from other hydroxyl compounds or unsaturated fatty acids than those specified above. For example, esters derived from a saturated alcohol having five or less carbon atoms and the above-described unsaturated fatty acid have unsatisfactory heat resistance, and unsaturated fatty acid esters derived from a saturated alcohol having 13 or more carbon atoms or an unsaturated alcohol other than those having 14 to 18 carbon atoms have unswept-sfackory low-temperature resistance. Rosters derived from saturated fatty acids also prove unsatisfactory.
The unsaturated fatty acid ester of the present invention is used Lo in a quantity of 2.0 to 50 parts, preferably 5.0 to 30 parts by weight per 100 parts by weight of rubber. Inn the amount of the ester is less than 2.0 parts by weight per 100 parts by weight of rubber, no sufficient effect on low-tempera-lure resistance can be obtained, while when the amount exceeds 50 parts by weight, physical properties of rubber, such as thermal resistance, are seriouslyaffected and such a large quantity is uneconomical.
The improver of the present invention can be applied to any rubbers such as SIR, BRA NOR, CRY polyisoprene rubber, or ethylene/propylene rubber, and the rubbers containing the improver may be vulcanized with sulfur and cross-linked by a peroxide.
The low-temperature resistance improver of the present invention can be mixed with rubber to obtain a rubber blend composition by any of convent-tonal rubber kneading methods, for example, by means of open roll, Danbury mixeror kneader blender. Additives which are conventionally used in the rubber in-cluster, such as vulcanizing agents, vulcanization accelerators, fillers, softeners, antioxidant, or processing aids may be added.
The following examples are provided to illustrate the present in-vent:Lon in more detail, but are not to be construed as limiting the present Invention in any way.
Examples 1 to 5 and Comparative Examples 1 to 5 Basic formulation styrene/butadiene rubber SUB 1500) 100 parts by weight carbon black (HA) 50 zinc white No. 3 3 starlike acid vulcanization accelerator (DO) vulcanization accelerator (D) 0.5 sulfur 1.75 Lo low-temperature resistance improver variable (given in Table 1) The above ingredients were mixed by means of an open roll. Vowel-concision was carried out at 145C for 35 min. by means of a press. Tensile test was carried out according to JIG K 6301 to obtain general physical properties. Low temperature resistance was evaluated based on a low-temperature flexibility test made according to ASTM D 10~3 by using a Clash-Berg testing machine. Heat resistance was evaluated on the basis of a heating loss test of a vulcanized sheet at 100C for I hr. For the purpose of comparison, a forum-lotion wherein the low-temperature resistance improver was omitted from the basic formulation and formulations wherein process oil (aromatic), DIVA, bottle owlet or oilily Stewart was added in place of said improver were used as Comparative Examples. The results are shown in Table 1.
It is apparent from Table 1 that Comparative Example 1 is inferior in Low temperature resistance so that a low temperature resistance improver is a usual ingredient in fields where such a resistance is required. Comparative Example 2 shows the use of softeners most frequently used in the rubber induct-rye but both the low temperature and heat resistance are very poor. Comparative Example 3 shows the use of a known low-temperature plasticizer I
5~3 DIVA. The low-temperature and heat resistances are relatively good, though considerably inferior to those of Examples 1 to 5. The low-temperature nests-lance of Comparative Example 4 is comparable but the heat resistance is so poor that the formulation of this Example can not be practically used. Come parative Example 5 shows the use of a saturated fatty acid unsaturated alcohol ester, which is considerably inferior to Examples 1 to 5 in low-temperature nests-lance.
3~3 o I
u I I -r I i Ox I ED O I
_ or o o o Al I Jo Us Jo o I Jo _ X a l o coo, I O
o . _ _ X o I I I
_ . or) I us By I X O co I I
_ TV o Ox`) or o En '.~., _ I
ox a I I o 00 Al I
O J- O I_ Jo a o o Al I,.,, ~~:~ I I or _ - Ox r l rat Jo I
I X I: O l Jo Jo o or so /
pa /~,~/. on aye c at / /6 Jo , Jo I s u Jo I// 3 I _ o c mu a azaleas OOZE so dolt l~ols~-ld Lou / do of aye '~Z~Z~3~
Examples 6 to 9 and Comparative Examples 6 to 9 Basic formulation chloroprene rubber (neoprene type W) 100 parts by weight magnesium oxide 4 antioxidant(N-phenyl-~-naphthylamine) 2 carbon black (SURF) 58 zinc white No. 3 5 vulcanization accelerator 0.5 (2-mercaptoimidazoline) Starkey acid 0.5 low-temperature resistance improver 15 The ingredients described above were mixed by means of an open roll. Vulcanization was carried out at 150C for 30 mix by means of a press. For the purpose of comparison, a formulation wherein the low-temperature resistance improver was omitted from the basic formulation and formulations wherein myristyl Stewart, DOS or bottle owlet was added in place of the improver of the present invention were used as Comparative Examples. Physical properties were evaluated in a similar manner to that of Example 1.
The results are shown in Table 2.
Jo C , I I o X
o I
CO JO En d J JO Cal O O
X o l o Us __ I, .
Jo I, . I a o X O Al O .
I, JO CO Hi"' I 00 O
X ox l Us I . , E I o co o o X o l Us Jo E X us o En .
.1_ Jo o X Jo o CO I
Jo I d E I _ _ __ .
Jo ox I
E r- O O o c~ l __ I _ ox /
Jo / a ooze clue' Jo E / :: o o 6 C so I us .,~ coo C
. / I 0 0 us I: o E / I Jo I a En at / Jo r Jo I C
3 / 3 Al O h r ox o o / E o o o J- a I/ I 4.1 3 KIWI pa I_ awl /aoue~slsal aoueislsal sal~ladold Doyle of ~,ea~lleols~d lilac \~) _ ye,_
condensation reaction between the hydroxyl compounds and the unsaturated fatty acids or an ester exchange reaction between the hydroxyl compounds and lower alkyd esters of the unsaturated fatty acids.
Examples of the esters suitable for use in -the present invention include octal owlet, decal owlet, tall oil fatty acid octal ester, oilily owlet, ethylene glycol dwelt, 1,4-butanediol dwelt, 1,6-hexanediol dwelt, 2-ethylhexyl owlet, dodecyl owlet, decal myristoleate, and oilily myristoleate, among which octal owlet is preferred.
By adding the low-temperature resistance it prover of the present invention to rubber, the low-temperature resistance can be greatly improved while other physical properties, particularly heat resistance, can be maintained or improved.
Though it is not clear why the low-temperature resistance improver of the present invention is superior to conventional compounds, it is thought to be Sue to wits chemical structure such as alkyd chain length, ester linkage, or unsaturated bond.
In any case, the improver of the present invention must be an ester derived from the hydroxyl compound and the unsaturated fatty acid as specified above.
The effect of the present invention can not be obtained _ _ ? Fly t`'' ~"~,~ 9~9~3 by an ester derived from other hydroxyl compounds or unsaturated fatty acids than those specified above. For example, esters derived from a saturated alcohol having five or less carbon atoms and the above-described unsaturated fatty acid have unsatisfactory heat resistance, and unsaturated fatty acid esters derived from a saturated alcohol having 13 or more carbon atoms or an unsaturated alcohol other than those having 14 to 18 carbon atoms have unswept-sfackory low-temperature resistance. Rosters derived from saturated fatty acids also prove unsatisfactory.
The unsaturated fatty acid ester of the present invention is used Lo in a quantity of 2.0 to 50 parts, preferably 5.0 to 30 parts by weight per 100 parts by weight of rubber. Inn the amount of the ester is less than 2.0 parts by weight per 100 parts by weight of rubber, no sufficient effect on low-tempera-lure resistance can be obtained, while when the amount exceeds 50 parts by weight, physical properties of rubber, such as thermal resistance, are seriouslyaffected and such a large quantity is uneconomical.
The improver of the present invention can be applied to any rubbers such as SIR, BRA NOR, CRY polyisoprene rubber, or ethylene/propylene rubber, and the rubbers containing the improver may be vulcanized with sulfur and cross-linked by a peroxide.
The low-temperature resistance improver of the present invention can be mixed with rubber to obtain a rubber blend composition by any of convent-tonal rubber kneading methods, for example, by means of open roll, Danbury mixeror kneader blender. Additives which are conventionally used in the rubber in-cluster, such as vulcanizing agents, vulcanization accelerators, fillers, softeners, antioxidant, or processing aids may be added.
The following examples are provided to illustrate the present in-vent:Lon in more detail, but are not to be construed as limiting the present Invention in any way.
Examples 1 to 5 and Comparative Examples 1 to 5 Basic formulation styrene/butadiene rubber SUB 1500) 100 parts by weight carbon black (HA) 50 zinc white No. 3 3 starlike acid vulcanization accelerator (DO) vulcanization accelerator (D) 0.5 sulfur 1.75 Lo low-temperature resistance improver variable (given in Table 1) The above ingredients were mixed by means of an open roll. Vowel-concision was carried out at 145C for 35 min. by means of a press. Tensile test was carried out according to JIG K 6301 to obtain general physical properties. Low temperature resistance was evaluated based on a low-temperature flexibility test made according to ASTM D 10~3 by using a Clash-Berg testing machine. Heat resistance was evaluated on the basis of a heating loss test of a vulcanized sheet at 100C for I hr. For the purpose of comparison, a forum-lotion wherein the low-temperature resistance improver was omitted from the basic formulation and formulations wherein process oil (aromatic), DIVA, bottle owlet or oilily Stewart was added in place of said improver were used as Comparative Examples. The results are shown in Table 1.
It is apparent from Table 1 that Comparative Example 1 is inferior in Low temperature resistance so that a low temperature resistance improver is a usual ingredient in fields where such a resistance is required. Comparative Example 2 shows the use of softeners most frequently used in the rubber induct-rye but both the low temperature and heat resistance are very poor. Comparative Example 3 shows the use of a known low-temperature plasticizer I
5~3 DIVA. The low-temperature and heat resistances are relatively good, though considerably inferior to those of Examples 1 to 5. The low-temperature nests-lance of Comparative Example 4 is comparable but the heat resistance is so poor that the formulation of this Example can not be practically used. Come parative Example 5 shows the use of a saturated fatty acid unsaturated alcohol ester, which is considerably inferior to Examples 1 to 5 in low-temperature nests-lance.
3~3 o I
u I I -r I i Ox I ED O I
_ or o o o Al I Jo Us Jo o I Jo _ X a l o coo, I O
o . _ _ X o I I I
_ . or) I us By I X O co I I
_ TV o Ox`) or o En '.~., _ I
ox a I I o 00 Al I
O J- O I_ Jo a o o Al I,.,, ~~:~ I I or _ - Ox r l rat Jo I
I X I: O l Jo Jo o or so /
pa /~,~/. on aye c at / /6 Jo , Jo I s u Jo I// 3 I _ o c mu a azaleas OOZE so dolt l~ols~-ld Lou / do of aye '~Z~Z~3~
Examples 6 to 9 and Comparative Examples 6 to 9 Basic formulation chloroprene rubber (neoprene type W) 100 parts by weight magnesium oxide 4 antioxidant(N-phenyl-~-naphthylamine) 2 carbon black (SURF) 58 zinc white No. 3 5 vulcanization accelerator 0.5 (2-mercaptoimidazoline) Starkey acid 0.5 low-temperature resistance improver 15 The ingredients described above were mixed by means of an open roll. Vulcanization was carried out at 150C for 30 mix by means of a press. For the purpose of comparison, a formulation wherein the low-temperature resistance improver was omitted from the basic formulation and formulations wherein myristyl Stewart, DOS or bottle owlet was added in place of the improver of the present invention were used as Comparative Examples. Physical properties were evaluated in a similar manner to that of Example 1.
The results are shown in Table 2.
Jo C , I I o X
o I
CO JO En d J JO Cal O O
X o l o Us __ I, .
Jo I, . I a o X O Al O .
I, JO CO Hi"' I 00 O
X ox l Us I . , E I o co o o X o l Us Jo E X us o En .
.1_ Jo o X Jo o CO I
Jo I d E I _ _ __ .
Jo ox I
E r- O O o c~ l __ I _ ox /
Jo / a ooze clue' Jo E / :: o o 6 C so I us .,~ coo C
. / I 0 0 us I: o E / I Jo I a En at / Jo r Jo I C
3 / 3 Al O h r ox o o / E o o o J- a I/ I 4.1 3 KIWI pa I_ awl /aoue~slsal aoueislsal sal~ladold Doyle of ~,ea~lleols~d lilac \~) _ ye,_
Claims (10)
PROPERTY OR PRIVILEGE IS CLAIMED ARE DEFINED AS FOLLOWS:
1. A low-temperature resistance improver for rubber, comprising an ester derived from an unsaturated fatty acid having 12 to 24 carbon atoms and at least one hydroxyl compound selected from the group consisting of saturated alcohols having 6 to 12 carbon atoms, unsaturated alcohols having 14 to 18 carbon atoms and glycols having 2 to 6 carbon atoms.
2. An improver according to claim 1, wherein the unsaturated fatty acid is oleic acid or tall oil fatty acid.
3. An improver according to claim 1 wherein the saturated alcohol is selected from the group consisting of hexyl alcohol, 2-ethylhexyl alcohol, n-octyl alcohol, n-decyl alcohol, and lauryl alcohol, the unsaturated alcohol is selected from the group consisting of myristoleyl alcohol and oleyl alcohol, the glycol is selected from the group consisting of ethylene glycol, propylene glycol, diethylene glycol, neopentyl glycol, butanediol, and hexanediol and the unsaturated fatty acid is selected from the group consisting of lauroleic acid, oleic acid, elaidic acid, erucic acid, linoleic acid, linoelaidic acid, eleostearic acid, myristoleic acid and linolenic acid.
4. An improver according to claim 1 wherein the ester is an ester selected from the group consisting of octyl oleate, decyl oleate, tall oil fatty acid octyl ester, oleyl oleate, ethylene glycol dioleate, 1,4-butanediol dioleate, 1,6-hexanediol dioleate, 2-ethylhexyl oleate, dodecyl oleate, decyl myristoleate, and oleyl myristoleate.
5. An improver according to claim 1 wherein the ester is octyl oleate.
6. A rubber comprising an improver according to claim 1, 2 or 3.
7. A rubber comprising an improver according to claim 4 or 5.
8. A rubber comprising an improver according to claim 1, 2 or 3 wherein the ester is used in a quantity of 2.0 to 50 parts by weight per 100 parts by weight of rubber.
9. A rubber comprising an improver according to claim 1, 2 or 3 wherein the ester is used in a quantity of 5.0 to 30 parts by weight per 100 parts by weight of rubber.
10. A rubber comprising an improver according to claim 1, 2 or 3 wherein the ester is used in a quantity of 2.0 to 50 parts by weight per 100 parts by weight of rubber and the rubber is SBR, BR, NBR, CR, polyisoprene rubber, or ethylene/propylene rubber.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP232165/82 | 1982-12-28 | ||
| JP23216582A JPH0238104B2 (en) | 1982-12-28 | 1982-12-28 | GOMUNOTAIKANSEIKOJOZAI |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1225393A true CA1225393A (en) | 1987-08-11 |
Family
ID=16935009
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000444248A Expired CA1225393A (en) | 1982-12-28 | 1983-12-23 | Low-temperature resistance improver for rubber |
Country Status (2)
| Country | Link |
|---|---|
| JP (1) | JPH0238104B2 (en) |
| CA (1) | CA1225393A (en) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0684402A (en) * | 1991-08-21 | 1994-03-25 | Takao Goto | Decorative lantern for bon testival |
| US5252650A (en) * | 1992-08-24 | 1993-10-12 | The Goodyear Tire & Rubber Company | Rubber compounds containing alkyl (C12 -C22) esters of a mixture of fatty acids |
| JP2000212335A (en) | 1999-01-21 | 2000-08-02 | Bridgestone Corp | Rubber composition |
| CN106905576A (en) * | 2017-03-16 | 2017-06-30 | 无锡市中惠橡胶科技有限公司 | A kind of cold-resistant drive belt primer and preparation method thereof |
-
1982
- 1982-12-28 JP JP23216582A patent/JPH0238104B2/en not_active Expired - Lifetime
-
1983
- 1983-12-23 CA CA000444248A patent/CA1225393A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| JPS59122532A (en) | 1984-07-16 |
| JPH0238104B2 (en) | 1990-08-29 |
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