CA2497265A1 - Improved polyolefin-based adhesive resins and method of making adhesive resins - Google Patents

Improved polyolefin-based adhesive resins and method of making adhesive resins Download PDF

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Publication number
CA2497265A1
CA2497265A1 CA002497265A CA2497265A CA2497265A1 CA 2497265 A1 CA2497265 A1 CA 2497265A1 CA 002497265 A CA002497265 A CA 002497265A CA 2497265 A CA2497265 A CA 2497265A CA 2497265 A1 CA2497265 A1 CA 2497265A1
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CA
Canada
Prior art keywords
polyolefin
based adhesive
adhesive resin
produced according
olefin
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Granted
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CA002497265A
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French (fr)
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CA2497265C (en
Inventor
Shida Mitsuzo
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MSI Technology LLC
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Publication of CA2497265A1 publication Critical patent/CA2497265A1/en
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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
    • 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
    • C09J123/02—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 not modified by chemical after-treatment
    • C09J123/04—Homopolymers or copolymers of ethene
    • C09J123/08—Copolymers of ethene
    • C09J123/0807—Copolymers of ethene with unsaturated hydrocarbons only containing more than three carbon atoms
    • C09J123/0815—Copolymers of ethene with aliphatic 1-olefins
    • 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
    • C08L2666/24—Graft or block copolymers according to groups C08L51/00, C08L53/00 or C08L55/02; Derivatives thereof
    • 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

Abstract

A method for producing polyolefin-based adhesive resins having improved physical and optical properties and the improved adhesive. resins thereby produced, eliminates at least one reheating and melting of polyolefin polymer, comprises polymerizing a monomer composition of at least one olefin, mixing the polymerization product without pelletizing the polyolefin polymer with at least one graft polymer or copolymer in a heated mixing device at a temperature above the melting point of the components, and recovering the resulting polyolefin-based adhesive resin.

Claims (43)

1. A method for producing improved polyolefin-based adhesive resin, comprising:
a. polymerizing a monomer composition of at least one olefin;
b. mixing with shear mixing the polymerization product following polymerization without first pelletizing the polyolefin with at least one graft polymer or copolymer in a heated mixing device at a temperature above the melting point of the components; and c. recovering the resulting polyolefin-based adhesive resin.
2. The method of claim 1, wherein the polyolefin-based adhesive resin comprises from about 0.05 percent to about 30 percent by weight of graft copolymer.
3. The method of claim 1, further comprising the step of adding an adhesion promoting resin to the heated mixing device.
4. The method of claim 3, wherein the adhesion promoting resin comprises a thermoplastic elastomer.
5. The method of claim 3, wherein the adhesion promoting resin comprises a metallocene catalyzed ethylene copolymer.
6. The method of claim 1, wherein the at least one olefin is an alkene.
7. The method of claim 6, wherein the at least one olefin is ethylene.
8. The method of claim 1, wherein the monomer composition comprises-a.
mixture of ethylene and at least one additional monomer.
9. The method of claim 8, wherein the monomer composition comprises a mixture of more than 50% by weight ethylene and less than 50% by weight of at least one additional monomer.
10. The method of claim 9, wherein the at least one additional monomer is selected from the group consisting of olefins having at least from 2 to 8 carbon atoms, unsaturated aliphatic hydrocarbons and ethylenically unsaturated esters or acids.
11. The method of claim 9, wherein the at least one additional monomer is an alkene monomer selected from the group consisting of propylene, butene-1, hexene-1, 4-methyl pentene-1, and octene-1.
12. The method of claim 9, wherein the at least one additional monomer is an ethylenically unsaturated ester or acid selected from the group consisting of vinyl acetate, methyl acrylate, ethyl acrylate, methyl methacrylate, ethyl methacrylate, butyl acrylate, acrylic acid, and methacrylic acid.
13. The method of claim 1, wherein the at least one olefin is propylene.
14. A method for producing improved polyolefin-based adhesive resin, comprising:

a. polymerizing a monomer composition selected from the group consisting of an olefin having from 2 to 8 carbon atoms, a mixture of an olefin having from 2 to 8 carbon atoms with a second, different olefin having from 2 to 8 carbon atoms, a mixture of said olefin with at least one other unsaturated aliphatic hydrocarbon, a mixture of said olefin having from 2 to 8 carbon atoms with a second, different olefin having from 2 to 8 carbon atoms and at least one other unsaturated aliphatic hydrocarbon, a mixture of said olefin with at least one ethylenically unsaturated ester or acid, and mixtures thereof;
b. mixing the polymerization product following polymerization without first palletizing with shear mixing with at least one graft polymer or copolymer in a heated mixing device at a temperature above the melting point of the components; and c. recovering the resulting polyolefin-based adhesive resin.
15. The method of claim 14, further comprising tie step of adding an adhesion promoting resin to the heated mixing device.
16. The method of claim 15, wherein the adhesion promoting resin comprises a thermoplastic elastomer.
17. The method of claim 15, wherein the adhesion promoting resin comprises a metallocene catalyzed ethylene copolymer.
18. The method of claim 14, wherein the monomer composition is an olefin having from 2 to 8 carbon atoms.
19 19. The method of claim 18, wherein the monomer composition comprises a mixture ofi more than 50% by weight ethylene and less than 50% by weight of at least one additional monomer.
20. The method of claim 18, wherein the monomer composition is a mixture. of a first olefin having from 2 to 8 carbon atoms and a second different olefin having from 2 to 8 carbon atoms.
21. The method of claim 19, wherein the monomer composition comprises a mixture of ethylene and at least one other unsaturated aliphatic hydrocarbon.
22. The method of claim 19, wherein the monomer composition comprises a mixture of ethylene and an alkene monomer selected from the group consisting of propylene, butane-1, hexane-1, 4-methyl pentane-1, and octane-1.
23. The method of claim 14, wherein the monomer composition comprises a mixture of ethylene and an ethylenically unsaturated ester or acid.
24. The method of claim 23, wherein the monomer composition comprises a mixture of ethylene and an ethylenically unsaturated ester or acid selected from the group consisting of vinyl acetate, methyl acrylate, ethyl acrylate, methyl methacrylate, ethyl methacrylate, butyl acrylate, acrylic acid, and methacrylic acid.
25. The method of claim 14, wherein the monomer composition comprises a mixture ofi more than 50% by weight ethylene gas and less than 50% by weight butane gas, the graft polymer is at least one polymerizable ethylenically unsaturated carboxylic acid or acid derivative, and the mixing is performed at a temperature above the melting point of the components.
26. A polyolefin-based adhesive resin produced according to the method of claim 1.
27. A polyolefin-based adhesive resin produced according to the method of claim 14.
28. A polyolefin-based adhesive resin produced according to the method of claim 25.
29. A polyolefin-based adhesive resin produced according to claim 1 for use in bonding to substrates.
30. A polyolefin-based adhesive resin produced according to claim 1 for use in bonding polyolefins, polyamides, polyvinyl alcohol, ethylene vinyl alcohol copolymer, metals, glass, wood, and/or paper.
31. A polyolefin-based adhesive resin produced according to claim 1 for use in a fabrication process.
32. A polyolefin-based adhesive resin produced according to claim 1 for use in a fabrication process selected from the group consisting of powder coating, rotational molding, film-forming process using standard cast film and blown film extrusion and coextrusion processes, application to multiple substrates using thermal lamination, extrusion lamination, and extrusion and coextrusion processes including blow molding, sheet extrusion, and pipe.
33. A polyolefin-based adhesive resin produced according to claim 14 for use in bonding to substrates.
34. A polyolefin-based adhesive resin produced according to claim 14 for use in bonding polyolefins, polyamides, polyvinyl alcohol, ethylene vinyl alcohol copolymer, metals, glass, wood, and/or paper.
35. A polyolefin-based adhesive resin produced according to claim 14 for use in a fabrication process.
36. A polyolefin-based adhesive resin produced according to claim 14 for use in a fabrication process selected from the group consisting of powder coating, rotational molding, film-forming process using standard cast film and blown film extrusion and coextrusion processes, application to multiple substrates using thermal lamination, extrusion lamination, and extrusion and coextrusion processes including blow molding, sheet extrusion, and pipe.
37. A polyolefin-based adhesive resin produced according to claim 25 for use in bonding to substrates.
38. A polyolefin-based adhesive resin produced according to claim 25 for use in bonding polyolefins, polyamides, polyvinyl alcohol, ethylene vinyl alcohol copolymer, metals, glass, wood, and/or paper.
39. A polyolefin-based adhesive resin produced according to claim 25 for use in a fabrication process.
40. A polyolefin-based adhesive resin produced according to claim 25 for use in a fabrication process selected from the group consisting of powder coating, rotational molding, film-forming process using standard cast film and blown film extrusion and coextrusion processes, application to multiple substrates using thermal lamination, extrusion lamination, and extrusion and coextrusion processes including blow molding, sheet extrusion, and pipe.
41. A method of bonding substrates comprising:

a. applying to at least one substrate a polyolefin-based adhesive resin produced according to claim 1; and b. applying a second substrate to the polyolefin-based adhesive resin applied to the at least one substrate.
42. A method of bonding substrates comprising:

a. applying to at least one substrate a polyolefin-based adhesive resin produced according to claim 14; and b. applying a second substrate to the polyolefin-based adhesive resin applied to the at least one substrate.
43. A method of bonding substrates comprising:

a. applying to at least one substrate a polyolefin-based adhesive resin produced according to claim 25; and b. applying a second substrate to the polyolefin-based adhesive resin applied to the at least one substrate.
CA2497265A 2002-09-04 2003-08-07 Improved polyolefin-based adhesive resins and method of making adhesive resins Expired - Lifetime CA2497265C (en)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
US40802202P 2002-09-04 2002-09-04
US60/408,022 2002-09-04
US10/612,031 2003-07-02
US10/612,031 US7064163B2 (en) 2002-09-04 2003-07-02 Polyolefin-based adhesive resins and method of making adhesive resins
PCT/US2003/024755 WO2004022661A2 (en) 2002-09-04 2003-08-07 Polyolefin adhesive and production process therefor

Publications (2)

Publication Number Publication Date
CA2497265A1 true CA2497265A1 (en) 2004-03-18
CA2497265C CA2497265C (en) 2011-06-14

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CA2497265A Expired - Lifetime CA2497265C (en) 2002-09-04 2003-08-07 Improved polyolefin-based adhesive resins and method of making adhesive resins

Country Status (9)

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US (2) US7064163B2 (en)
EP (1) EP1543085B1 (en)
JP (1) JP4944379B2 (en)
CN (1) CN100558805C (en)
AT (1) ATE455831T1 (en)
AU (1) AU2003259052A1 (en)
CA (1) CA2497265C (en)
DE (1) DE60331084D1 (en)
WO (1) WO2004022661A2 (en)

Families Citing this family (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7064163B2 (en) * 2002-09-04 2006-06-20 Msi Technology Llc Polyolefin-based adhesive resins and method of making adhesive resins
US7700707B2 (en) * 2002-10-15 2010-04-20 Exxonmobil Chemical Patents Inc. Polyolefin adhesive compositions and articles made therefrom
JP4972284B2 (en) 2002-10-15 2012-07-11 エクソンモービル・ケミカル・パテンツ・インク Multiple catalyst systems for olefin polymerization and polymers produced therefrom
EP1859926B1 (en) * 2006-05-26 2012-04-25 Borealis Technology Oy Coated pipe comprising polyolefin layer with enhanced adhesion
US8047752B2 (en) * 2007-06-25 2011-11-01 Msi Technology L.L.C. Fastener assembly and multi-layered structure
DE102008052619B4 (en) * 2008-10-21 2012-02-23 Henkel Ag & Co. Kgaa Cohesive bonding of wire-shaped individual elements by means of a two-layer system based on acrylate resins
US20100276057A1 (en) * 2009-04-30 2010-11-04 H.B. Fuller Company Ethylene-butene copolymer, adhesive composition including the same, and method of making and using the same
US8637159B2 (en) 2010-09-29 2014-01-28 Equistar Chemicals, Lp Graft composition for improved tie layers
US8685539B2 (en) 2011-08-26 2014-04-01 Equistar Chemicals, Lp Graft composition having long chain branched olefins for improved layers
US8673451B2 (en) 2011-08-26 2014-03-18 Equistar Chemicals, Lp Multilayer thermoplastic structures with improved tie layers
CN103865142B (en) * 2012-12-11 2018-12-28 国家能源投资集团有限责任公司 A kind of crosslinkable polyethylene blend composition
US10240072B2 (en) 2013-10-17 2019-03-26 Equistar Chemicals, Lp Compositions with a grafted polyolefin copolymer having constituents of an unsaturated monomer, an olefin elastomer, and a long-chain branched polyolefin
CN109153898A (en) * 2016-05-20 2019-01-04 伊奎斯塔化学有限公司 The technique and its adhesive composition and film of adhesive composition of the online production based on polyolefin
WO2017200869A1 (en) * 2016-05-20 2017-11-23 Equistar Chemicals, Lp In-line polyolefin based adhesive compositions having graft polyolefin/elastomer compositions having graft polyolefin/lastomer copolymers
CA3019603C (en) 2016-06-03 2023-07-04 Msi Technology Llc Adhesive compositions, articles including the adhesive compositions, and methods thereof
WO2018098796A1 (en) * 2016-12-02 2018-06-07 Dow Global Technologies Llc Process to form a composition containing functionalized and un-functionalized ethylene-based polymers
CN110295019B (en) * 2019-06-13 2020-11-10 江苏鸿硕工程塑料科技股份有限公司 Polyethylene pipe bonding material and preparation method thereof
CN114539949A (en) * 2021-12-30 2022-05-27 上海邦中高分子材料股份有限公司 Special adhesive resin for fluorocarbon coated metal plate for architectural decoration and preparation method thereof

Family Cites Families (42)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4087587A (en) * 1975-09-19 1978-05-02 Chemplex Company Adhesive blends
US4087588A (en) * 1975-09-22 1978-05-02 Chemplex Company Adhesive blends
US4298712A (en) * 1977-08-01 1981-11-03 Chemplex Company Adhesive blends of elastomer, polyolefin, and graft of polyethylene with unsaturated fused ring anhydrides
US4486469A (en) * 1977-08-01 1984-12-04 Chemplex Company Method of making a composite structure
US4423117A (en) * 1977-08-01 1983-12-27 Chemplex Company Composite structure
US4477532A (en) * 1980-08-15 1984-10-16 Chemplex Company Composite structures
US4472555A (en) * 1980-08-15 1984-09-18 Chemplex Company Adhesive blends containing ethylene polymer grafted with carboxylic reactant
US4409364A (en) * 1981-12-04 1983-10-11 Chemplex Company Adhesive blends and composite structures comprising acid or anhydride modified PE + hope + polypropylene
US4430135A (en) * 1981-12-04 1984-02-07 Chemplex Company Adhesive blends and methods of making composite structures
US4419408A (en) * 1981-12-04 1983-12-06 Chemplex Company Composite structures
US4487885A (en) * 1982-01-18 1984-12-11 Chemplex Company Adhesive blends
US4537836A (en) * 1982-01-18 1985-08-27 Chemplex Company Composite structures
US4481262A (en) * 1982-02-19 1984-11-06 Chemplex Company Composite structures
US4452942A (en) * 1982-02-19 1984-06-05 Chemplex Company Adhesive blends containing anacid or anhydride grafted LLDPE
JPS58149935A (en) * 1982-03-01 1983-09-06 Ube Ind Ltd Modified polyolefin composition
US4416944A (en) * 1982-03-31 1983-11-22 Chemplex Company Composite structures
US4460745A (en) * 1982-04-26 1984-07-17 Chemplex Company Adhesive three-component blends containing grafted HDPE
US4460632A (en) * 1982-04-26 1984-07-17 Chemplex Company Adhesive blends and composite structures
JPS59179551A (en) * 1983-03-29 1984-10-12 Ube Ind Ltd Adhesive polyolefin composition and laminatings therefrom
EP0289494B1 (en) * 1986-11-06 1995-03-01 E.I. Du Pont De Nemours And Company Plastic composite barrier structures
GB8827335D0 (en) * 1988-11-23 1988-12-29 Du Pont Canada Method for manufacture of modified polypropylene compositions
US5070143A (en) * 1989-03-09 1991-12-03 Morton International, Inc. Adhesive blend of polyolefins and grafted block copolymer of polystyrene
US5360350A (en) * 1991-08-23 1994-11-01 The Whitaker Corporation Sealant compositions and sealed electrical connectors
CA2090202A1 (en) * 1992-02-25 1993-08-26 Jeffrey A. Jones Method for improving anhydride-functionalized polymers and products
JPH08504226A (en) * 1992-12-03 1996-05-07 レイケム・コーポレイション Heat recoverable compositions and articles
DE4313290A1 (en) * 1993-04-23 1994-10-27 Kempter Werner Method and device for producing a cross-linked extruded polymer product
JP3337777B2 (en) * 1993-10-05 2002-10-21 昭和電工株式会社 Adhesive resin composition
US5741343A (en) * 1995-07-28 1998-04-21 Union Oil Company Of California Adjustable hot glass transfer device
JP3592816B2 (en) * 1995-12-27 2004-11-24 日本ポリオレフィン株式会社 Adhesive resin composition and laminate thereof
US5709953A (en) * 1996-02-21 1998-01-20 Morton International, Inc. Extrudable resin for polystyrene and laminate
US5733085A (en) * 1996-08-06 1998-03-31 Illinois Tool Works, Inc. Fastener assembly and adhesive composition
US5744533A (en) * 1997-06-04 1998-04-28 Johnson Matthey, Inc. Adhesive composition for bonding a semiconductor device
ES2172941T3 (en) * 1997-10-31 2002-10-01 Kraton Polymers Res Bv FOAM COMPOSITION CONTAINING OIL, THERMOPLASTIC ELASTOMERO AND EXPANDABLE PARTICLES.
JP3890738B2 (en) * 1998-04-09 2007-03-07 日本ゼオン株式会社 Resin composition containing soft polymer
US6184298B1 (en) * 1998-06-19 2001-02-06 E. I. Du Pont De Nemours And Company Adhesive compositions based on blends of grafted polyethylenes and non-grafted polyethylenes and styrene container rubber
JP3971574B2 (en) * 1998-06-22 2007-09-05 ゼネラル・エレクトリック・カンパニイ Silane cured thermoplastic elastomer
US6194485B1 (en) * 1999-04-01 2001-02-27 Bridgestone Corporation Compounding process for achieving uniform, fine particle size dispersion of curing agents with minimal use of solvents
US6730292B1 (en) * 1999-09-03 2004-05-04 The Procter & Gamble Company Hair care composition comprising a polypropylene glycol and an ester oil
SG97811A1 (en) * 1999-09-24 2003-08-20 Advanpack Solutions Pte Ltd Fluxing adhesive
US6358622B1 (en) * 1999-12-16 2002-03-19 M.S.I. Technology L.L.C. Heat sealable films
US6805959B2 (en) * 2001-11-27 2004-10-19 Guardian Industries Corporation Composite laminate structures especially useful for automotive trim components, and methods and tie layers employed to make the same
US7064163B2 (en) * 2002-09-04 2006-06-20 Msi Technology Llc Polyolefin-based adhesive resins and method of making adhesive resins

Also Published As

Publication number Publication date
WO2004022661A3 (en) 2004-06-10
EP1543085A2 (en) 2005-06-22
CN1678677A (en) 2005-10-05
JP4944379B2 (en) 2012-05-30
ATE455831T1 (en) 2010-02-15
EP1543085B1 (en) 2010-01-20
CN100558805C (en) 2009-11-11
WO2004022661A2 (en) 2004-03-18
CA2497265C (en) 2011-06-14
US20050228133A1 (en) 2005-10-13
AU2003259052A8 (en) 2004-03-29
JP2005538212A (en) 2005-12-15
AU2003259052A1 (en) 2004-03-29
EP1543085A4 (en) 2006-08-09
DE60331084D1 (en) 2010-03-11
US7064163B2 (en) 2006-06-20
US20040044131A1 (en) 2004-03-04

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