USRE32634E - Adhesive for bonding cured EPDM rubber - Google Patents
Adhesive for bonding cured EPDM rubber Download PDFInfo
- Publication number
- USRE32634E USRE32634E US06/926,428 US92642886A USRE32634E US RE32634 E USRE32634 E US RE32634E US 92642886 A US92642886 A US 92642886A US RE32634 E USRE32634 E US RE32634E
- Authority
- US
- United States
- Prior art keywords
- adhesive
- iaddend
- iadd
- concentration
- pphr
- 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 - Lifetime
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J153/00—Adhesives based on block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Adhesives based on derivatives of such polymers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/67—Unsaturated compounds having active hydrogen
- C08G18/69—Polymers of conjugated dienes
- C08G18/696—Polymers of conjugated dienes containing heteroatoms other than oxygen and other than the heteroatoms of copolymerised vinyl monomers
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2666/00—Composition of polymers characterized by a further compound in the blend, being organic macromolecular compounds, natural resins, waxes or and bituminous materials, non-macromolecular organic substances, inorganic substances or characterized by their function in the composition
- C08L2666/02—Organic macromolecular compounds, natural resins, waxes or and bituminous materials
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2666/00—Composition of polymers characterized by a further compound in the blend, being organic macromolecular compounds, natural resins, waxes or and bituminous materials, non-macromolecular organic substances, inorganic substances or characterized by their function in the composition
- C08L2666/02—Organic macromolecular compounds, natural resins, waxes or and bituminous materials
- C08L2666/04—Macromolecular compounds according to groups C08L7/00 - C08L49/00, or C08L55/00 - C08L57/00; Derivatives thereof
- C08L2666/08—Homopolymers or copolymers according to C08L7/00 - C08L21/00; Derivatives thereof
Definitions
- This invention relates to an improved solvent based contact adhesive which is useful for providing a strong bond between sheets of cured ethylene-propylene-diene terpolymers (EPDM).
- EPDM cured ethylene-propylene-diene terpolymers
- EPDM rubber is widely used in the tire industry.
- the bonding techniques used in tires requires special surface preparation and high pressure and heat conditioning.
- EPDM membranes are used as material other than for tires, such as for a roofing material, it is sometimes necessary to prepare a lap seam bonding to EPDM membranes to itself.
- neoprene-based adhesive may be used for bonding EPDM rubber.
- the commonly used adhesive is one based on neoprene dissolved in a mixture of solvents and incorporating resins, fillers, curatives and stabilizers to a total solids content of about 23%. This compound develops a T-peel adhesion of approximately 2 lbs./inch width.
- Adhesives based on neoprene generally have excellent resistance to creep and cold flow, but have the drawback of providing only low levels of bond strength to cured EPDM.
- EPDM itself is a poor adhesive polymer. When EPDM is used as an adhesive the resulting compounds have little or no tack and when uncured are very thermoplastic.
- an adhesive formulation comprising a blend of three rubbers, namely, (1) a halogenated butyl rubber, (2) a pre-crosslinked butyl rubber and (3) a three block copolymer with polystyrene end blocks and a rubbery poly(ethylene-butylene) mid block, together with a petroleum hydrocarbon based aliphatic thermoplastic resin having a high softening point and an aliphatic isocyanate.
- the invention also provides an improved method for preparing said adhesive which method comprises the separate milling or mixing in a Banbury (TM) mixer of said halogenated and pre-crosslinked butyl rubbers and sequential additions when solubilizing the ingredients with the butyl rubbers first and the isocyanate modifier last into a cool churn which has been purged of moisture.
- TM Banbury
- the halogenated butyl rubber ingredient is preferably Bromobutyl of 27-51 Mooney viscosity (ML 1+8 at 125° C.) and 2.0-2.5% bromine content.
- the halogenated butyl rubber may be added at a concentration of 20.0-45.0 parts per hundred parts of rubber.
- Chlorobutyl rubber may be used in place of bromobutyl rubber.
- the Mooney viscosity of said chlorobutyl rubber is in the range 27-51 (ML 1+8 at 125° C.) and possesses a 1.1-1.3% chlorine content.
- Adhesives incorporating chlorobutyl rubber impart bond strengths between cured EPDM sheets higher than those given with neoprene adhesives currently used but lower than those given by the preferred bromobutyl rubber adhesives of this invention.
- Halogenation of the above polymer is derived through a proprietary process with up to 90% of the halogenation situated allylic to the double bond with retention of most of the unsaturation. This is schematically represented as follows: ##STR2## Where X is Cl or Br and n is about 50
- halogenated butyl rubbers may be of the bromobutyl or chlorobutyl type made by Polysar Ltd., Sarnia, Ontario, Canada or by Exxon Chemical Company, Houston, Tex.
- the pre-crosslinked butyl rubber is also derived from regular butyl rubber through a proprietary process by incorporating a crosslinking agent during the polymerization of the rubber.
- the finished product may be schematically represented as follows: ##STR3##
- n is about 50 and A is a crosslinking agent such as 1,4 divinyl benzene, methyl divinyl benzene 1,3 butadiene, isoprene, 2-ethyl 1,3-butadiene, 1,6 hexadiene, 1,6-hexanediol-diacrylate, 2 methyl-1,3-butadiene, butyleneglycol dimethylacrylate, 1,4 butanediol diacrylate, thiodiglycol dimethacrylate, diallyl maleate, decamethylene glycol diacrylate, 2-chloro 1,3 butadiene, polyethylene glycol dimethyacrylate, 1 phenyl ethylene-1,2-dimethacrylate.
- A is a crosslinking agent such as 1,4 divinyl benzene, methyl divinyl benzene 1,3 butadiene, isoprene, 2-ethyl 1,3-butadiene, 1,6 hexadiene,
- Such pre-crosslinked butyl rubber may be of the type made by Polysar Ltd., Sarnia, Ontario, Canada and may be of a weight percent solubility in cyclohexane of 15-50 percent and a concentration 40.0-65.0 parts per hundred parts of rubber.
- the styrene(ethylene-butylene)styrene block thermoplastic rubber ingredient may be of the type produced by Shell Chemical Company, Houston, Tex. with a styrene content of 28-29% by weight, a midblock content of 71-72% by weight and tensile strength of 4500-5000 lbs./in 2 and said block copolymer used at a concentration of 15.0-20.0 parts per hundred of rubber.
- a block copolymer also applicable in this invention is one where the butylene in the midblock is replaced by propylene to give a styrene-(ethylene propylene)-styrene block copolymer.
- n is from 20 to 1200 and n' is from 70 to 700.
- the low molecular weight high softening point, thermoplastic, aliphatic type hydrocarbon based resin is made from petroleum monomers.
- the aliphatic resin is introduced to impart improved compatibility between the block copolymer and butyl rubbers, and to improve the high temperature heat strength of the butyl rubbers.
- the aliphatic resin is derived from hydrocarbon feedstock monomers possessing 5-9 carbon atoms polymerized to varying molecular weight ranges so as to give softening points of 162° C. to 181° C.
- the preferred resin is one possessing a higher softening point range from 175°-181° C.
- the higher softening resin when incorporated into the formulations of this invention impart higher strengths to butyl and block copolymers mixtures at the test temperatures of about 70° C.
- An example of high softening point resins applicable in the invention is the Piccovar (TM) series produced by Hercules, Inc. Wilmington, Del. with a softening point of 175°-181° C., an acid number of less than 1 and a bromine number of 16.0-20.0 at a concentration of 120.0-160.0 parts per 100 rubber.
- the organic isocyanate ingredient of the invention functions to provide a cure of the halogenated butyl rubber when exposed to moisture.
- Useful organic isocyanates include 1,6 hexamethylene diisocyanate; 2,4 and 2,6-toluene diisocyanate; 4,4-diphenylmethane diisocyanate; polymethylene polyphenylisocyanate; 4,4-dicyclohexylmethane diisocyanate; xylylene diisocynate; but, most of these tend to give either short gel times or reduced high temperature heat strength.
- a preferred type is Desmodur (TM) N-75 isocyanate available in a 75% solution from Mobay Chemical Corporation, Pittsburgh, Penn.
- This material has an NCO content of 15.0-17.0% and is an aliphatic compound which is an adduct based on 1,6 hexamethylene diisocyanate: ##STR5## Said isocynate is used at concentrations in the range of 20.0-35.0 parts per 100 rubber.
- an adsorbent of the alkali-metal alumino-silicate zeolite family of compounds is added.
- Typical Molecular Sieves are 5A or 13X supplied by the Linde division of Union Carbide, New York, N.Y. Said Molecular Sieves are used at a concentration of 5.0-15.0 parts per 100 parts of rubber.
- zinc oxide may be added at a concentration of 0.5-2.0 parts per 100 parts of rubber.
- a typical zinc oxide is Protox 166 produced by New Jersey Zinc Co.
- the zinc oxide is added to allow some modulus increase of the halogenated butyl rubber, but little enough so that the solution stability is not adversely affected.
- the aforementioned ingredients are dispersed in an organic liquid having a solubility parameter of 8.5-8.9 and a hydrogen bonding index 3.0-3.5.
- Said solvent is used at a concentration of 500.0-640.0 parts per 100 parts rubber giving a total solids level of 31.0-37.0 percent.
- the dispersing medium may be a blend of 2 or more solvents.
- Carbon black may also be added for pigmenting purposes and/or to improve mill or Banbury (TM) processing of the butyl polymers.
- the carbon black may be of medium reinforcement character, having an ASTM number from N-285 thru N-330. Said carbon black is used at a concentration of 2.0-20.0 parts per 100 parts rubber.
- the ingredients are processed and mixed in a controlled sequence.
- the halogenated butyl and pre-crosslinked butyl are separately milled or mixed in Banbury (TM) mixer to homogenize them and work some of the nerve out. It has been found that carbon black improves the processing of the mill or the Banbury (TM) mixed batches.
- Solubilization of the adhesive is initiated by dispersing the mill/Banbury batches in 75% of the solvent. It is important that the heat build up be kept at a minimum throughout the solubilizing procedure. This is followed, after a period of 2-3 hours, by the addition of the thermoplastic resin, thermoplastic rubber and molecular sieves to begin scavenging moisture. At this point the mixing vessel should be sealed and purged with nitrogen.
- the zinc oxide should be added with the remaining solvent.
- the mixing vessel is then resealed and purged followed by mixing for 1 hour minimum or until smooth. This is followed by cooling of the churn to no more than 80° F. Any evaporated solvent is then replaced, along with blending in of the isocyanate.
- This example illustrates the adhesion level generated by the industry standard neoprene-based adhesive such as N-100 distributed by Carlisle Corp.
- Test samples were prepared by vigorously washing the surface of a particular 0.065" thick cured EPDM membrane with a cloth soaked with heptane. 1" ⁇ 6" strips were then cut. A thin coat of the N-100 adhesive was then brushed onto the strips and allowed to dry 15 min.
- T-peel adhesion samples were prepared by bringing the whole adhesive coated side of one strip together with the adhesive coated side of another strip, followed by lamination with a hand roller.
- Lap shear adhesion samples were prepared by bringing strips together so a 1" ⁇ 1" contact area was formed, followed by lamination with a hand roller.
- Adhesion samples were then allowed to stand undisturbed for 7 days at 25° C. This was followed by adhesion testing on an Instron (TM) tensile tester with the jaw speed set for 2 in./min. and testing being performed at 25° C. and 70° C. The following results were obtained:
- This example illustrates the adhesion level generated by the adhesive and manufacturing procedure of the instant invention.
- the Bromobutyl with carbon black and precrosslinked butyl were mixed separately on a two roll mill for 20 minutes minimum. Above mill batches could also be processed in a Banbury (TM) for a minimum of 6 minutes. These mill batches were then cut-up and added to an adhesive churn loaded with 75% or 375 PPHR of the above solvents, hexane and toluene. This was allowed to mix 2 hours minimum. This was followed by the addition of the Piccovar AB180, the Kraton G1652, the Molecular Sieves #5A. At this point, the churn was sealed and purged with dry nitrogen. This was allowed to mix an additional 2 hours minimum, followed by the addition of the zinc oxide and the remaining 25% or 125 PPHR of solvent.
- TM Banbury
Abstract
Description
TABLE 1 ______________________________________ Test @ 2 in./min. 25° C. Results 70° C. Results ______________________________________ T-Peel Adhesion 2.2 1.5 (lbs./in. width) Lap Shear Adhesion 14.8 12.0 (lbs./in..sup.2) ______________________________________
______________________________________ Ingredient Parts by Weight ______________________________________ Mill Batch A Polysar Bromobutyl X-2 45.0 Cabot Regal 300 Carbon Black 2.0 47.0 Mill Batch B Polysar Butyl XL-20 40.0 40.0 Churn Batch Mill Batch A 47.0 Mill Batch B 40.0 Shell Kraton G1652 15.0 Hercules Piccovar AB180 150.0 Protox 166 ZnO 2.0 Molecular Sieves #5A 10.0 Toluene 400.0 Hexane 100.0 Desmodur N-75 (75% solids solution) 25.0 789.0 Total Solids: 35.8% ______________________________________
TABLE 2 ______________________________________ Test @ 2 in./min. 25° C. Results 70° C. Results ______________________________________ T-Peel Adhesion 6.4 2.4 (lbs./in. width) Lap Shear Adhesion 35.7 18.8 (lbs./in..sup.2) ______________________________________
TABLE 3 ______________________________________ T-Peel Adhesion @ 2 in./min. Test Temperature (lbs./in. width) ______________________________________ 25° C. 4.5 70° C. 0.7 ______________________________________
TABLE 4 ______________________________________ T-Peel Adhesion @ 2 in./min. Test Temperature (lbs./in. width) ______________________________________ 25° C. 4.0 70° C. 0.9 ______________________________________
TABLE 5 ______________________________________ T-Peel Adhesion @ 2 in./min. Test Temperature (lbs./in. width) ______________________________________ 25° C. 6.3 70° C. 1.2 ______________________________________
Claims (11)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US06/926,428 USRE32634E (en) | 1983-12-27 | 1986-11-03 | Adhesive for bonding cured EPDM rubber |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US06/565,266 US4501842A (en) | 1983-12-27 | 1983-12-27 | Adhesive for bonding cured EPDM rubber |
US06/926,428 USRE32634E (en) | 1983-12-27 | 1986-11-03 | Adhesive for bonding cured EPDM rubber |
Related Parent Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US06/565,266 Reissue US4501842A (en) | 1983-12-27 | 1983-12-27 | Adhesive for bonding cured EPDM rubber |
Publications (1)
Publication Number | Publication Date |
---|---|
USRE32634E true USRE32634E (en) | 1988-03-29 |
Family
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Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US06/926,428 Expired - Lifetime USRE32634E (en) | 1983-12-27 | 1986-11-03 | Adhesive for bonding cured EPDM rubber |
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Country | Link |
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US (1) | USRE32634E (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4851462A (en) | 1988-01-21 | 1989-07-25 | Uniroyal Plastics Company, Inc. | Adhesive for bonding cured EPDM rubber containing a crosslinked halogenated butyl rubber |
US5260126A (en) * | 1990-01-10 | 1993-11-09 | Kimberly-Clark Corporation | Low stress relaxation elastomeric nonwoven webs and fibers |
Citations (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3354107A (en) * | 1965-09-28 | 1967-11-21 | Goodrich Co B F | Tackifying cements for epm and epdm rubbers |
US3582508A (en) * | 1969-11-28 | 1971-06-01 | Goodyear Tire & Rubber | Rubber modified with organic polyisocyanates in presence of promoters |
US3635861A (en) * | 1968-06-28 | 1972-01-18 | Flintkote Co | Pressure-sensitive hot-melt adhesives |
GB1272763A (en) * | 1968-05-10 | 1972-05-03 | Dunlop Holdings Ltd | Adhesive compositions |
FR2154651A1 (en) * | 1971-09-28 | 1973-05-11 | Sumitomo Chemical Co | Bonding rubber/metal - with mixture of organic isocyanate and sulpho (halogenated) ethylene/propylene/diene rubber |
US3917607A (en) * | 1971-09-22 | 1975-11-04 | Shell Oil Co | Block copolymer adhesive compositions |
US4022745A (en) * | 1974-01-25 | 1977-05-10 | Stamicarbon B.V. | Process for the preparation of a glue based on a thermoplastic elastomeric block-copolymer |
US4096204A (en) * | 1976-06-07 | 1978-06-20 | Shell Oil Company | Halogenated thermoplastic/block copolymer blend |
US4112020A (en) * | 1976-05-24 | 1978-09-05 | Cities Service Company | Hot melt butyl sealant intermediate |
-
1986
- 1986-11-03 US US06/926,428 patent/USRE32634E/en not_active Expired - Lifetime
Patent Citations (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3354107A (en) * | 1965-09-28 | 1967-11-21 | Goodrich Co B F | Tackifying cements for epm and epdm rubbers |
GB1139486A (en) * | 1965-09-28 | 1969-01-08 | Goodrich Co B F | Tackifying cements for epm and epdm rubbers |
GB1272763A (en) * | 1968-05-10 | 1972-05-03 | Dunlop Holdings Ltd | Adhesive compositions |
US3635861A (en) * | 1968-06-28 | 1972-01-18 | Flintkote Co | Pressure-sensitive hot-melt adhesives |
US3582508A (en) * | 1969-11-28 | 1971-06-01 | Goodyear Tire & Rubber | Rubber modified with organic polyisocyanates in presence of promoters |
US3917607A (en) * | 1971-09-22 | 1975-11-04 | Shell Oil Co | Block copolymer adhesive compositions |
FR2154651A1 (en) * | 1971-09-28 | 1973-05-11 | Sumitomo Chemical Co | Bonding rubber/metal - with mixture of organic isocyanate and sulpho (halogenated) ethylene/propylene/diene rubber |
US4022745A (en) * | 1974-01-25 | 1977-05-10 | Stamicarbon B.V. | Process for the preparation of a glue based on a thermoplastic elastomeric block-copolymer |
US4112020A (en) * | 1976-05-24 | 1978-09-05 | Cities Service Company | Hot melt butyl sealant intermediate |
US4096204A (en) * | 1976-06-07 | 1978-06-20 | Shell Oil Company | Halogenated thermoplastic/block copolymer blend |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4851462A (en) | 1988-01-21 | 1989-07-25 | Uniroyal Plastics Company, Inc. | Adhesive for bonding cured EPDM rubber containing a crosslinked halogenated butyl rubber |
WO1989006669A1 (en) * | 1988-01-21 | 1989-07-27 | Uniroyal Plastics Company, Inc. | Adhesive for bonding cured epdm rubber |
US5260126A (en) * | 1990-01-10 | 1993-11-09 | Kimberly-Clark Corporation | Low stress relaxation elastomeric nonwoven webs and fibers |
US5288791A (en) * | 1990-01-10 | 1994-02-22 | Kimberly-Clark Corporation | Low stress relaxation elastomeric fibers |
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