CA1087823A - Method of bonding - Google Patents
Method of bondingInfo
- Publication number
- CA1087823A CA1087823A CA276,801A CA276801A CA1087823A CA 1087823 A CA1087823 A CA 1087823A CA 276801 A CA276801 A CA 276801A CA 1087823 A CA1087823 A CA 1087823A
- Authority
- CA
- Canada
- Prior art keywords
- rubber
- filamentary material
- resin
- rubber composition
- aromatic
- 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
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
- C08J5/04—Reinforcing macromolecular compounds with loose or coherent fibrous material
- C08J5/06—Reinforcing macromolecular compounds with loose or coherent fibrous material using pretreated fibrous materials
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
- D06M15/693—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with natural or synthetic rubber, or derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2321/00—Characterised by the use of unspecified rubbers
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Manufacturing & Machinery (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Textile Engineering (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Manufacture Of Macromolecular Shaped Articles (AREA)
- Moulding By Coating Moulds (AREA)
- Lining Or Joining Of Plastics Or The Like (AREA)
Abstract
A B S T R A C T
A method of bonding an aromatic polyamide filamentary material to a rubber composition comprising applying an aqueous solution or dispersion of an epoxy resin to the filamentary material, drying the coated filamentary material and assembling the coated filamentary material with a rubber composition con-taining resin precursors and vulcanising said composition in contact with the coated filamentary material.
A method of bonding an aromatic polyamide filamentary material to a rubber composition comprising applying an aqueous solution or dispersion of an epoxy resin to the filamentary material, drying the coated filamentary material and assembling the coated filamentary material with a rubber composition con-taining resin precursors and vulcanising said composition in contact with the coated filamentary material.
Description
~ his invention relates to a method of bonding an aromatic polyamide filamentary material to a rubber composition and is an improvemen~ in or modification of the method described in U.K. Patent Specification No. 1 465 063. Silica may be included in the rubber composition.
. .
: According to the presen~ invention a method of bonding an aromatic polyamide filamentary material to a rubber composition comprises applying an aqueous solution or disp~rsion of an epoxy : resin to the filamentary material, drying the coated filamentary , ., material and assembling the coated filamentary material with a ` rubber composition containing aldehyde resin precursors, that is .~ at leas~ two components which will react to form a thermosetting aldehyde condensation resin and subjecting the assembly to conditions which will vulcanise the rubber composition and cause the aldehyde . resin precursors to react.
The aromatic polyamide filamentary material may be of the formula ,, l - 11 '1l -Arl-C-~N- n or . - N-C-Arl-L I A 2 ¦ n . wherein Arl and Ar2 are aromatic radicals and n is an integer, for example poly-lj 4-ben7amide ;~, ' O ~
~ _ ':
EI n and poly~l,4-phenylene terephthalamide) ~:
:
8 7~3 ., _ o o ,: i~ ~
~1 n .( WiliCh are available in fibre form from DuPon~: as Fibre B
. ~ .
.
,,;
`:
., ~
~ .
.:
'.~
:...
. ., ?
:` `
,' :
,.
., '~1 ~ ., .
,i .. ,.
i,, ' :' ,~
. . , . :, :
;';:' :
';
, ','~, ~: '', ~:,; :
.i:, : ' ,:' : ::: .::: : `.. ,. ,':::,,,: ,.,. ,.,. ' : ., ': : :: :".'.: : . '::: :: ::: :: .: :-: , .. :: :~: .:. .: ' ' . ' :, - :
.':::, . ' : :.:: ' :: :,:, :: :'': . ,- : :: '~ :' '':: '': . ': : i,:' : ` ': ': ' :'. .: : : , '' . :' . .. :- '' - . : . .:. ~ ` ~: ; ' .' ' , ~ ' : , ' :
(rr~ q~k~
or Kevlar/ and poly(l,3-phenylene isophthalamide) J
C~
H n which is available in fibre form from DuPont as ~omex tregistered Trade Mark~.
Epoxy resins that may be used are those resins that may be formed into an aq~ous solution or dispersion.
. ............ .
Typical epoxy compounds include those based on the reaction product of 2,2-bis(p-hydroxyphenyl)~propane (Bisphenol A) with epichlorohydrin, the reaction product of an aliphatic diol or triol with epichlorohydrin; epoxidised polybutadiene and triglycidyl isocyanurate.
A typical example of a water soluble epoxy resin is : /IJ~R olo ~ e~e~ which is commercially available from NOGASI and is based on the diglycidyl ether of glycerol.
The aqueous solution or dispersion of an epoxy resin may also contain swelling agents for the resin e.g.
. .
: According to the presen~ invention a method of bonding an aromatic polyamide filamentary material to a rubber composition comprises applying an aqueous solution or disp~rsion of an epoxy : resin to the filamentary material, drying the coated filamentary , ., material and assembling the coated filamentary material with a ` rubber composition containing aldehyde resin precursors, that is .~ at leas~ two components which will react to form a thermosetting aldehyde condensation resin and subjecting the assembly to conditions which will vulcanise the rubber composition and cause the aldehyde . resin precursors to react.
The aromatic polyamide filamentary material may be of the formula ,, l - 11 '1l -Arl-C-~N- n or . - N-C-Arl-L I A 2 ¦ n . wherein Arl and Ar2 are aromatic radicals and n is an integer, for example poly-lj 4-ben7amide ;~, ' O ~
~ _ ':
EI n and poly~l,4-phenylene terephthalamide) ~:
:
8 7~3 ., _ o o ,: i~ ~
~1 n .( WiliCh are available in fibre form from DuPon~: as Fibre B
. ~ .
.
,,;
`:
., ~
~ .
.:
'.~
:...
. ., ?
:` `
,' :
,.
., '~1 ~ ., .
,i .. ,.
i,, ' :' ,~
. . , . :, :
;';:' :
';
, ','~, ~: '', ~:,; :
.i:, : ' ,:' : ::: .::: : `.. ,. ,':::,,,: ,.,. ,.,. ' : ., ': : :: :".'.: : . '::: :: ::: :: .: :-: , .. :: :~: .:. .: ' ' . ' :, - :
.':::, . ' : :.:: ' :: :,:, :: :'': . ,- : :: '~ :' '':: '': . ': : i,:' : ` ': ': ' :'. .: : : , '' . :' . .. :- '' - . : . .:. ~ ` ~: ; ' .' ' , ~ ' : , ' :
(rr~ q~k~
or Kevlar/ and poly(l,3-phenylene isophthalamide) J
C~
H n which is available in fibre form from DuPont as ~omex tregistered Trade Mark~.
Epoxy resins that may be used are those resins that may be formed into an aq~ous solution or dispersion.
. ............ .
Typical epoxy compounds include those based on the reaction product of 2,2-bis(p-hydroxyphenyl)~propane (Bisphenol A) with epichlorohydrin, the reaction product of an aliphatic diol or triol with epichlorohydrin; epoxidised polybutadiene and triglycidyl isocyanurate.
A typical example of a water soluble epoxy resin is : /IJ~R olo ~ e~e~ which is commercially available from NOGASI and is based on the diglycidyl ether of glycerol.
The aqueous solution or dispersion of an epoxy resin may also contain swelling agents for the resin e.g.
2-pyrrolidone, wetting agents e.g. dioctyl sodium sulpho~uccinate (e.g. the compound whlch i9 cammercially Crrc,d~ ~rh) available as "Aerosol OT"I~rom American Cynamid) or any other compound that will assist in the ~ormation of the solution or dispersion, or the coating o~ the ~ilamentary material with `
the solution or dispersion.
The rubber composition containing resin precursors is pre~erably vulcanised using sulphur as the vulcanising agent. The rubber employed in the composition may be ~ natural rubber~ styrene-butadiene rubber, cis-1,4-poly-.
;"
` 3 .:: .: ~ :.,, , : ,. ~, , .: , . .
.: ~ . . :,. : , , , :: :
:: ~ - . . , , , . : :
~'7~ 3 isoprene rubber, polybutadiene rubber or a blend o~ any of these rubbers.
Particularly suitable aldehyde resin precursors com-pounds are an aromatic hydroxy compound and a compound which on heating becomes a methylene donor. Alternatively, one of the resin precursors may itself be a resin capable o further reaction eg. ~ novolac phenol-formaldehyde resin deficient in methyle groups in combination wi~h a compound which on heating becomes a methylene donor. The compound which becomes a methylene donor is pre~erably stable up to a temperature of at least 100C. These compounds in-clude those which generate formaldehyde on heating or may be com-`- pounds such as hexamethylenetetramine. Other suitable compounds include hexamethoxymethyl melamine, lauryl-oxymethyl pyridinium chloride, cetyloxy~ethyl pyridinium chloride, ethyloxymethyl pyridin- ;
ium chloride, formaldehyde, polymers of ~ormaldehyde and polymers of formaldehyde having stabilising groups or residues of substances such as pentaerythritol at the ends of the molecules.
The amou~t of compound employed which liberates methylene groups may be from 0~1 to 10 parts by weight, preferably from 0.5 , 20 to 3 parts by weight, per 100 parts by weight of rubber in the com-~, position.
The aromatic hydroxy compound which may be employed may be a monohydroxy compound, but it is pre~erably one containing two hydroxy groups and it is especially preferred that the hydroxy groups be meta to each other. Examples of suitable aromatic hydroxy compounds are resorcinol and .r.
`
.~
lr3-dihydroxy naphthalene. If desired, melamine or urea or a compound which generates either o theqe two compounds on heating may be employed in place of the aromatic hydroxy compound.
The amount of aromatic hydro~y compound or other compound employed to react with the compound which liberateq methylene groups may be from 0.1 to 10 parts by weight, preferably from 1.0 to 4.0 parts by weight, per 100 parts by weight of rubber in the composition.
The aqueous solution or dlspersion of an epoxy resin may be applied to the filamentary material by passing the ., .
material into the aqueous solution or dispersion at room temperature, but i~ desired higher temperatures may be used.
. . .
- After the application of the epoxy resin coating the 5 material is dried. The drying process may comprise drying .~! at room temperature ollowed by drying at a higher temperature. The rubber composltion containing resin precursors is then applied to khe coated filamentary ~material and the assembly is then suitably subjected to heat and~pressure to vulcanise the composition and form the resin precursors into a resin, thereby producing a bond . . , between the coated filamentary material and the rubber composition.
; The method of the present invention may be used to ; ?5 bond aromatic polyamide filamentary materials in the orm of reinforcing cords to rubber~ compositions, in the manufacture o~ e.g. tyres, driving belts, conveyor belts and hose.~
~ c~
,'. ' :
~:: :.
~Q8'7~i~3 The method accordin~ to the present inven~ion is illu~trated by the followin~ Example in ~hich all parts are by welght,:-EXAMP~E
Reinforcing cords based on the fibre~ produced frompoly(l,4-phenylene terephthalamide) as Fibre B availa~le from DuPont were coated on a labora~ory ~cale with an epoxy ~
resin solu~ion of the ~ormulation given below, and were , :
~' subsequently dried. ~:
Part~
' Water 84.0 `~:
;~.', Sodium hydroxide (10% solution) 1.0 Epoxy resinl 3.0 2-pyrrolidone 10.0 ',, 15 Wetting agent~ 2.0 1 - Diglycidyl ether o~ gl~cerol (was commercially available dc. /na~
,,.`. ~ as "Epon 812"/rom Shell) ~ 2 = Dioctyl sodium sulphosuccinate (commercially available ~, ',~ as l'Aerosol OT" from American Cynamide) Untreated cords and cords treated with the epoxy resin solution were embedded in rubber compositions A to C
(Table I). The composition~ were then vulcanised for 25 ~ minute~ at 148C.
2 The adhesion between the reinforcing cords and the rubber composition in each case was then meaaured using a atandard 1 cm pull-through test,(similar ko J O Wood Trans : I R I, Vol. 32, No. 1, February 1956). The avsrage adhesion ~ :
~,~,values determined over 10 measurements are recorded in Table II. : ', .
, ., :.
~;',` ~
- :: : ,.......... - - ~ :. , . , : . : :~: : :: :
P7~ 3 TABLE I ~ B C
~atural rubber 100.00 100.00 100.00 Stearic acid 2.75 1.90 1.05 Retarder.(50/0 active0.60 0.60 0.60 cyclohexylthiophthalimide) Antioxidant ~diphenylamine/ l.oo l.oo l.oo ~: acetone reaction product) Process oil (aromatic7.00 7.00 7.00 -~ process oil available as Dutrex RT~from Shell) ( T~ac/c. rrlark~
'~J~ Zinc oxide 7.50 7.50 7.50 : Carbon black (A furnace 43.00 43.00 43.00 black available as Regal 30~)~ r~ h~
Sulphur 2.60 2.60 2.60 .~ Accelerator (2,4 morph- 1.20 1.20 1.20 iolinyl mercapto-: benzthiazole .: ~e~amethylene tetramine - 0.80 1.60 Resorcinol/stear.ic acid - 2.10 4.20 (60/40 melt) - ~
165.65 167.70169.75 :. TABLE II
.
Adhesion (Mewtons/cm) .
Rubber Composition Treated Cords U~treated Cords ;`: C 138 96 ., ~:., , ., :
, .
::
:',"
.
: :
:
7.
- :,: : :: , . . . ~ . . ;. .
the solution or dispersion.
The rubber composition containing resin precursors is pre~erably vulcanised using sulphur as the vulcanising agent. The rubber employed in the composition may be ~ natural rubber~ styrene-butadiene rubber, cis-1,4-poly-.
;"
` 3 .:: .: ~ :.,, , : ,. ~, , .: , . .
.: ~ . . :,. : , , , :: :
:: ~ - . . , , , . : :
~'7~ 3 isoprene rubber, polybutadiene rubber or a blend o~ any of these rubbers.
Particularly suitable aldehyde resin precursors com-pounds are an aromatic hydroxy compound and a compound which on heating becomes a methylene donor. Alternatively, one of the resin precursors may itself be a resin capable o further reaction eg. ~ novolac phenol-formaldehyde resin deficient in methyle groups in combination wi~h a compound which on heating becomes a methylene donor. The compound which becomes a methylene donor is pre~erably stable up to a temperature of at least 100C. These compounds in-clude those which generate formaldehyde on heating or may be com-`- pounds such as hexamethylenetetramine. Other suitable compounds include hexamethoxymethyl melamine, lauryl-oxymethyl pyridinium chloride, cetyloxy~ethyl pyridinium chloride, ethyloxymethyl pyridin- ;
ium chloride, formaldehyde, polymers of ~ormaldehyde and polymers of formaldehyde having stabilising groups or residues of substances such as pentaerythritol at the ends of the molecules.
The amou~t of compound employed which liberates methylene groups may be from 0~1 to 10 parts by weight, preferably from 0.5 , 20 to 3 parts by weight, per 100 parts by weight of rubber in the com-~, position.
The aromatic hydroxy compound which may be employed may be a monohydroxy compound, but it is pre~erably one containing two hydroxy groups and it is especially preferred that the hydroxy groups be meta to each other. Examples of suitable aromatic hydroxy compounds are resorcinol and .r.
`
.~
lr3-dihydroxy naphthalene. If desired, melamine or urea or a compound which generates either o theqe two compounds on heating may be employed in place of the aromatic hydroxy compound.
The amount of aromatic hydro~y compound or other compound employed to react with the compound which liberateq methylene groups may be from 0.1 to 10 parts by weight, preferably from 1.0 to 4.0 parts by weight, per 100 parts by weight of rubber in the composition.
The aqueous solution or dlspersion of an epoxy resin may be applied to the filamentary material by passing the ., .
material into the aqueous solution or dispersion at room temperature, but i~ desired higher temperatures may be used.
. . .
- After the application of the epoxy resin coating the 5 material is dried. The drying process may comprise drying .~! at room temperature ollowed by drying at a higher temperature. The rubber composltion containing resin precursors is then applied to khe coated filamentary ~material and the assembly is then suitably subjected to heat and~pressure to vulcanise the composition and form the resin precursors into a resin, thereby producing a bond . . , between the coated filamentary material and the rubber composition.
; The method of the present invention may be used to ; ?5 bond aromatic polyamide filamentary materials in the orm of reinforcing cords to rubber~ compositions, in the manufacture o~ e.g. tyres, driving belts, conveyor belts and hose.~
~ c~
,'. ' :
~:: :.
~Q8'7~i~3 The method accordin~ to the present inven~ion is illu~trated by the followin~ Example in ~hich all parts are by welght,:-EXAMP~E
Reinforcing cords based on the fibre~ produced frompoly(l,4-phenylene terephthalamide) as Fibre B availa~le from DuPont were coated on a labora~ory ~cale with an epoxy ~
resin solu~ion of the ~ormulation given below, and were , :
~' subsequently dried. ~:
Part~
' Water 84.0 `~:
;~.', Sodium hydroxide (10% solution) 1.0 Epoxy resinl 3.0 2-pyrrolidone 10.0 ',, 15 Wetting agent~ 2.0 1 - Diglycidyl ether o~ gl~cerol (was commercially available dc. /na~
,,.`. ~ as "Epon 812"/rom Shell) ~ 2 = Dioctyl sodium sulphosuccinate (commercially available ~, ',~ as l'Aerosol OT" from American Cynamide) Untreated cords and cords treated with the epoxy resin solution were embedded in rubber compositions A to C
(Table I). The composition~ were then vulcanised for 25 ~ minute~ at 148C.
2 The adhesion between the reinforcing cords and the rubber composition in each case was then meaaured using a atandard 1 cm pull-through test,(similar ko J O Wood Trans : I R I, Vol. 32, No. 1, February 1956). The avsrage adhesion ~ :
~,~,values determined over 10 measurements are recorded in Table II. : ', .
, ., :.
~;',` ~
- :: : ,.......... - - ~ :. , . , : . : :~: : :: :
P7~ 3 TABLE I ~ B C
~atural rubber 100.00 100.00 100.00 Stearic acid 2.75 1.90 1.05 Retarder.(50/0 active0.60 0.60 0.60 cyclohexylthiophthalimide) Antioxidant ~diphenylamine/ l.oo l.oo l.oo ~: acetone reaction product) Process oil (aromatic7.00 7.00 7.00 -~ process oil available as Dutrex RT~from Shell) ( T~ac/c. rrlark~
'~J~ Zinc oxide 7.50 7.50 7.50 : Carbon black (A furnace 43.00 43.00 43.00 black available as Regal 30~)~ r~ h~
Sulphur 2.60 2.60 2.60 .~ Accelerator (2,4 morph- 1.20 1.20 1.20 iolinyl mercapto-: benzthiazole .: ~e~amethylene tetramine - 0.80 1.60 Resorcinol/stear.ic acid - 2.10 4.20 (60/40 melt) - ~
165.65 167.70169.75 :. TABLE II
.
Adhesion (Mewtons/cm) .
Rubber Composition Treated Cords U~treated Cords ;`: C 138 96 ., ~:., , ., :
, .
::
:',"
.
: :
:
7.
- :,: : :: , . . . ~ . . ;. .
Claims (17)
1. A method of bonding an aromatic polyamide filament-ary material to a rubber composition comprises applying an aqueous solution or dispersion of an epoxy resin to the filamentary material, drying the coated filamentary material and assembling the coated filamentary material with a rubber composition containing aldehyde resin precursors, that is at least two components which will re-act to form a thermosetting aldehyde condensation resin, and sub-jecting the assembly to conditions which will vulcanise the rubber composition and cause that aldehyde resin precursors to react,
2. A method according to claim 1 wherein the aromatic polyamide filamentary material comprises a polymer of the formula or where A1 and Ar2 are aromatic radicals and n is an integer.
3. A method according to claim 2 wherein the aromatic polyamide filamentary material composes poly(1,4-benzamide).
4. A method according to claim 2 wherein the aromatic polyamide filamentary material comprises poly(1,3-phenylene iso-phthalamide).
5. A method according to claim 2 wherein the aromatic polyamide filamentary material comprises poly(1,4-phenylene tere-phthalamide).
6. A method according to claim 1, 2 or 3 wherein the epoxy resin is based on the reaction product of 2,2-bis (p-hydroxy-phenyl)- propane with epichlorohydrin.
7. A method according to claim 1, 2 or 3 wherein the rubber composition comprises sulphur as the vulcanising agent.
8. A method according to claim 1, 2 or 3 wherein the rubber employed in the composition comprises natural rubber, cis-1, 4-polyisoprene rubber, styrene-butadiene rubber, polybutadiene rubber and a mixture of two or more of these rubber.
9. A method according to claim 1, 2 or 5 wherein the resin precursors comprise an aldehyde condensation resin and a com-pound which on heating becomes a methylene donor.
10. A method according to claim 9 wherein the resin pre-cursors comprise an aromatic hydroxy compound and a compound which becomes a methylene donor on heating.
11. A method according to claim 10 wherein the methylene donating compound comprises hexamethylenetetramine, hexamethoxyme-thylmelamine, lauryloxymethyl pyridinium chloride, cetyloxymethyl pyridinium chloride, formaldehyde, a formaldehyde polymer and a formaldehyde polymer having stabilising groups or residues of sub-stances such as pentaerthritol at the ends of the molecules.
12. A method according to claim 10 or 11 wherein the methylene donating compound is used in an amount of 0.1 to 10 parts by weight per 100 parts by weight of rubber in the composition.
13. A method according to claim 10 wherein the aromatic hydroxy compound has two hydroxy groups arranged meta to each other.
14. A method according to claim 13 wherein the aromatic hydroxy compound comprises resorcinol or 1,3-dihydroxy naphthalene.
15. A method according to claim 10 or 11 wherein the aromatic hydroxy compound is used in an amount of 0,1 to 10 parts by weight per 100 parts by weight of rubber in the composition.
16. A method according to claim 1, 2 or 3 wherein the rubber composition contains silica.
17. An aromatic polyamide filamentary material bonded to a vulcanised rubber composition with an interlayer of an epoxy resin, the rubber composition containing a condensed aldehyde resin.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB21221/76 | 1976-05-21 | ||
| GB21221/76A GB1577942A (en) | 1976-05-21 | 1976-05-21 | Method of bonding |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1087823A true CA1087823A (en) | 1980-10-21 |
Family
ID=10159240
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA276,801A Expired CA1087823A (en) | 1976-05-21 | 1977-04-22 | Method of bonding |
Country Status (7)
| Country | Link |
|---|---|
| JP (1) | JPS52142786A (en) |
| AU (1) | AU507402B2 (en) |
| CA (1) | CA1087823A (en) |
| DE (1) | DE2722679A1 (en) |
| FR (1) | FR2352099A2 (en) |
| GB (1) | GB1577942A (en) |
| ZA (1) | ZA772305B (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS61167089A (en) * | 1985-01-17 | 1986-07-28 | 株式会社ブリヂストン | Treatment of aromatic polyamide fiber |
-
1976
- 1976-05-21 GB GB21221/76A patent/GB1577942A/en not_active Expired
-
1977
- 1977-04-14 AU AU24276/77A patent/AU507402B2/en not_active Expired
- 1977-04-15 ZA ZA00772305A patent/ZA772305B/en unknown
- 1977-04-22 CA CA276,801A patent/CA1087823A/en not_active Expired
- 1977-05-18 DE DE19772722679 patent/DE2722679A1/en not_active Withdrawn
- 1977-05-19 JP JP5819877A patent/JPS52142786A/en active Pending
- 1977-05-23 FR FR7715676A patent/FR2352099A2/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS52142786A (en) | 1977-11-28 |
| FR2352099A2 (en) | 1977-12-16 |
| FR2352099B2 (en) | 1978-10-20 |
| GB1577942A (en) | 1980-10-29 |
| ZA772305B (en) | 1978-03-29 |
| AU2427677A (en) | 1978-10-19 |
| DE2722679A1 (en) | 1977-12-01 |
| AU507402B2 (en) | 1980-02-14 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |