CA2462612A1 - Environmentally friendly adhesives for bonding vulcanized rubber - Google Patents

Environmentally friendly adhesives for bonding vulcanized rubber Download PDF

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Publication number
CA2462612A1
CA2462612A1 CA002462612A CA2462612A CA2462612A1 CA 2462612 A1 CA2462612 A1 CA 2462612A1 CA 002462612 A CA002462612 A CA 002462612A CA 2462612 A CA2462612 A CA 2462612A CA 2462612 A1 CA2462612 A1 CA 2462612A1
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CA
Canada
Prior art keywords
phr
adhesive composition
parts
composition according
nitroso compound
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.)
Granted
Application number
CA002462612A
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French (fr)
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CA2462612C (en
Inventor
Christian C. Green
Douglas H. Mowrey
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Lord Corp
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Individual
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Priority claimed from US10/222,545 external-priority patent/US20040033374A1/en
Application filed by Individual filed Critical Individual
Publication of CA2462612A1 publication Critical patent/CA2462612A1/en
Application granted granted Critical
Publication of CA2462612C publication Critical patent/CA2462612C/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L23/00—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers
    • C08L23/02—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers not modified by chemical after-treatment
    • C08L23/10—Homopolymers or copolymers of propene
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L15/00—Compositions of rubber derivatives
    • C08L15/02—Rubber derivatives containing halogen
    • 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
    • C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
    • C09J11/02—Non-macromolecular additives
    • 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
    • C09J123/00—Adhesives based on homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Adhesives based on derivatives of such polymers
    • C09J123/26—Adhesives based on homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Adhesives based on derivatives of such polymers modified by chemical after-treatment
    • C09J123/28—Adhesives based on homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Adhesives based on derivatives of such polymers modified by chemical after-treatment by reaction with halogens or compounds containing halogen
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L23/00—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers
    • C08L23/02—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers not modified by chemical after-treatment
    • C08L23/04—Homopolymers or copolymers of ethene
    • C08L23/08—Copolymers of ethene
    • C08L23/0846—Copolymers of ethene with unsaturated hydrocarbons containing other atoms than carbon or hydrogen atoms
    • C08L23/0892—Copolymers of ethene with unsaturated hydrocarbons containing other atoms than carbon or hydrogen atoms containing monomers with other atoms than carbon, hydrogen or oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L23/00—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers
    • C08L23/26—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers modified by chemical after-treatment
    • C08L23/28—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers modified by chemical after-treatment by reaction with halogens or compounds containing halogen
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L23/00—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers
    • C08L23/26—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers modified by chemical after-treatment
    • C08L23/32—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers modified by chemical after-treatment by reaction with compounds containing phosphorus or sulfur
    • C08L23/34—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers modified by chemical after-treatment by reaction with compounds containing phosphorus or sulfur by chlorosulfonation
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2312/00—Crosslinking
    • C08L2312/08—Crosslinking by silane
    • 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
    • C08L51/00—Compositions of graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers
    • C08L51/06—Compositions of graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers grafted on to homopolymers or copolymers of aliphatic hydrocarbons containing only one carbon-to-carbon double bond
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L61/00—Compositions of condensation polymers of aldehydes or ketones; Compositions of derivatives of such polymers
    • C08L61/04—Condensation polymers of aldehydes or ketones with phenols only
    • C08L61/06—Condensation polymers of aldehydes or ketones with phenols only of aldehydes with phenols
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L9/00—Compositions of homopolymers or copolymers of conjugated diene hydrocarbons

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • General Chemical & Material Sciences (AREA)
  • Adhesives Or Adhesive Processes (AREA)

Abstract

Adhesive compositions effective for bonding runner to metal and containing no more than about 1000 ppm of lead especially adapted to bond vulcanized elastomers to rigid substrates, like metal are disclosed. The adhesives are useful in combination with primer coats, and as one-coat adhesives and provide durable, rubber tearing primary adhesive bonds after exposure to harsh conditions. The adhesives exhibit excellent bond versatility, sweep resistance, and in-can storage stability. In one embodiment, the adhesive compositions of the present invention consist essentially of less than 1000 ppm of lead, at least one diluent as water or organic solvent, a halogen-containing film former, optionally a nitroso compound, brominated dichlorobutadiene, and/or adhesion promoter, and an acid scavenger comprising zinc phosphate.

Claims (15)

1. ~An adhesive composition containing less than 1000 ppm of lead, and comprising (a) ~at least one diluent comprising water or organic solvent, (b) ~a halogen-containing polyolefin, (c) ~optional nitroso compound, (d) ~an acid scavenger comprising zinc phosphate, and optionally (e) ~an adhesion promoter.
2. ~The adhesive of claim 1 wherein said halogen-containing polyolefin is chlorosulfonated polyethylene, said nitroso compound (c) is present and is a poly-C-nitroso compound, and said adhesive further comprises carbon black, and silica.
3. ~The adhesive of claim 1 containing the following:
(a) from 20 to 4000 PHR of said diluent, (b) 100 weight parts of said halogen-containing polyolefin;
(c) from 1 to 200 wt. parts 100 wt. parts of said halogenated polyolefin (PHR), of said nitroso compound;
(d) from 5 to 120 PHR of said acid scavenger comprising zinc phosphate;
(e) from 0 to 25 PHR, of said adhesion promoter.
4. ~The adhesive composition according to claim 1, wherein the halogen-containing polyolefin is selected from the group consisting of chlorinated natural rubber, chlorosulfonated polyethylene, chlorinated ethylene/propylene/non-conjugated diene terpolymers and mixtures thereof.
5. ~The adhesive composition according to claim 1 wherein (b) is chlorinated natural rubber (c) is an aromatic nitroso compound and further comprising a second halogen-containing polyolefin which is brominated polydichlorobutadiene, and (e) a maleimide compound.
6. ~The adhesive composition according to claim 1 wherein (b) is a combination of chlorinated natural rubber and chlorosulfonated polyethylene, (c) is an aromatic nitroso compound and (e) is a polyisocyanate compound.
7. ~The adhesive composition according to claim 1 wherein the nitroso compound is an aromatic nitroso compound present in an amount from 1 to 200 PHR, the said adhesion promoter is a maleimide compound present in an amount from 5 to 100 PHR, and said acid scavenger comprising zinc phosphate is present in an amount from 10 to 120 PHR.
8. ~An adhesive composition according to claim 7 wherein the aromatic nitroso compound is present in an amount from 50 to 150 PHR, the maleimide compound is present in an amount from 12 to 80 PHR and zinc phosphate is present in an amount from 12 to 80 PHR.
9. ~ An adhesive composition according to claim 1 further comprising a vulcanizing agent selected from the group consisting of sulfur and selenium.
10. An adhesive composition according to claim 9 wherein the vulcanizing agent is present in an amount from 5 to 30 parts by weight per 100 parts by weight of halogen-containing polyolefin.
11. An adhesive composition according to claim 1 wherein (e) is selected from a phenolic resin solution, a phenolic resin dispersion, and a phenolic epoxy resin,
12. An adhesive composition according to claim 11 wherein (e) is a novolak epoxy resin.
13. An adhesive composition according to claim 11 wherein the phenolic epoxy resin is present in an amount from about 2 to 50 parts by weight per 100 parts by weight of halogen-containing polyolefin.
14. An adhesive composition comprising (a) from 20 to 4000 parts per 100 parts of (b) (PHR) of a diluent, (b) 100 weight parts of at least one chlorinated natural rubber;
(c) from 1 to about PHR of a nitroso compound and 1 to 200 PHR of a brominated polydichlorobutadiene;
(d) from about 5 to about 120 PHR of an acid scavenger comprising zinc phosphate;
(e) from 1 to about 200 PHR, of an adhesion promoter selected from the group consisting of a maleimide compound, phenolic resin, epoxy resin, and a polyisocyanate, including mixtures thereof.
15. An adhesive composition comprising (a) from 20 to 4000 parts per 100 parts of (b) (PHR) of a diluent, (b) 100 weight parts of at least one chlorosulfonated polyethylene;
(c) from about 1 to 200 PHR of a nitroso compound and 1 to 200 PHR of a brominated polydichlorobutadiene;
(d) from 5 to about 120 PHR of an acid scavenger comprising zinc phosphate;
(e) from 1 to 200 PHR, of an adhesion promoter selected from the group consisting of a maleimide compound, a phenolic resin, and epoxy resin, a polyisocyanate, and mixtures thereof.
CA2462612A 2001-10-17 2002-10-17 Environmentally friendly adhesives for bonding vulcanized rubber Expired - Fee Related CA2462612C (en)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
US33003301P 2001-10-17 2001-10-17
US60/330,033 2001-10-17
US10/222,545 US20040033374A1 (en) 2002-08-16 2002-08-16 Phenolic adhesives for bonding peroxide-cured elastomers
US10/222,545 2002-08-16
PCT/US2002/033362 WO2003033613A1 (en) 2001-10-17 2002-10-17 Environmentally friendly adhesives for bonding vulcanized rubber

Publications (2)

Publication Number Publication Date
CA2462612A1 true CA2462612A1 (en) 2003-04-24
CA2462612C CA2462612C (en) 2011-08-02

Family

ID=26916919

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2462612A Expired - Fee Related CA2462612C (en) 2001-10-17 2002-10-17 Environmentally friendly adhesives for bonding vulcanized rubber

Country Status (3)

Country Link
CA (1) CA2462612C (en)
MX (1) MXPA04003502A (en)
WO (1) WO2003033613A1 (en)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CZ2003155A3 (en) 2002-01-30 2003-09-17 Rohm And Haas Company Aqueous adhesive preparations for adhesive bonding elastomers
WO2006007438A1 (en) * 2004-06-16 2006-01-19 Lord Corporation Adhesive composition, method for bonding to a metal surface and rubber to metal adhesive
CA2609170C (en) * 2006-11-15 2011-08-23 Rohm And Haas Company Waterborne adhesive for elastomers
EP3440144B1 (en) * 2016-04-04 2020-02-12 Dow Global Technologies, LLC Improved adhesive composition for bonding rubber to metal
CN110511300B (en) * 2019-09-18 2021-09-14 青岛科技大学 Halogenated trans-butadiene-isoprene copolymer rubber and preparation method and application thereof
CN110437769B (en) * 2019-09-18 2021-03-02 青岛科技大学 Vulcanizable crosslinked halogenated rubber adhesive and preparation method thereof
EP3950800A1 (en) * 2020-08-03 2022-02-09 Henkel AG & Co. KGaA Improved corrosion resistance in rubber-based adhesives and sealants

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3830784A (en) * 1972-03-22 1974-08-20 Lord Corp Shelf-stable adhesive compositions for laminating elastomers to metal and textile substrates and such laminates
US4119587A (en) * 1977-02-25 1978-10-10 Lord Corporation Adhesive compositions comprising (a) halogenated polyolefin (b) aromatic nitroso compound and (c) lead salts
IN162673B (en) * 1984-03-07 1988-06-25 Lord Corp
US5268404A (en) * 1989-12-04 1993-12-07 Lord Corporation One-coat rubber-to-metal bonding adhesive

Also Published As

Publication number Publication date
CA2462612C (en) 2011-08-02
MXPA04003502A (en) 2004-09-10
WO2003033613A1 (en) 2003-04-24

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Effective date: 20201019