CA2414498A1 - Adhesive alpha-olefin inter-polymers - Google Patents

Adhesive alpha-olefin inter-polymers Download PDF

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Publication number
CA2414498A1
CA2414498A1 CA002414498A CA2414498A CA2414498A1 CA 2414498 A1 CA2414498 A1 CA 2414498A1 CA 002414498 A CA002414498 A CA 002414498A CA 2414498 A CA2414498 A CA 2414498A CA 2414498 A1 CA2414498 A1 CA 2414498A1
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Canada
Prior art keywords
mol
determined
inter
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polymer
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Granted
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CA002414498A
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French (fr)
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CA2414498C (en
Inventor
Anthony George Karandinos
David J. Lohse
Olivier J. F. Georjon
Kenneth Lewtas
Jean M. Tancrede
Bruce A. Harrington
Keith A. Nelson
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ExxonMobil Chemical Patents Inc
Original Assignee
Exxon Chemical Patents Inc.
Anthony George Karandinos
David J. Lohse
Olivier J. F. Georjon
Kenneth Lewtas
Jean M. Tancrede
Bruce A. Harrington
Keith A. Nelson
Exxonmobil Chemical Patents Inc.
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Application filed by Exxon Chemical Patents Inc., Anthony George Karandinos, David J. Lohse, Olivier J. F. Georjon, Kenneth Lewtas, Jean M. Tancrede, Bruce A. Harrington, Keith A. Nelson, Exxonmobil Chemical Patents Inc. filed Critical Exxon Chemical Patents Inc.
Publication of CA2414498A1 publication Critical patent/CA2414498A1/en
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Publication of CA2414498C publication Critical patent/CA2414498C/en
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    • 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
    • C09J123/10—Homopolymers or copolymers of propene
    • 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
    • C09J123/10—Homopolymers or copolymers of propene
    • C09J123/14—Copolymers of propene
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F210/00—Copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
    • C08F210/04—Monomers containing three or four carbon atoms
    • C08F210/06—Propene
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2205/00—Polymer mixtures characterised by other features
    • C08L2205/02—Polymer mixtures characterised by other features containing two or more polymers of the same C08L -group
    • 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
    • C08L2314/00—Polymer mixtures characterised by way of preparation
    • C08L2314/06—Metallocene or single site catalysts
    • 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

Abstract

The invention relates to novel adhesive alpha-olefin inter-polymers which are largely amorphous and have a rheological behavior that makes them suitable for adhesive use, both without and with minimized amounts of tackifying resins. Specifically, the invention poly-alpha olefin inter-polymer may be composed of A) from 60 to 94 % of units derived from one alpha mono-olefin having from 3 to 6 carbon atoms and B) from 6 to 40 mol % of units derived from one or more other mono-olefins having from 4 to 10 carbon atoms and at least one carbon atom more than A); and C) optionally from 0 to 10 mol % of units derived from another copolymerizable unsaturated hydrocarbon, different from A) and B); the diad distribution of component A in the polymer as determined by 13C NMR as described herein showing a ratio of experimentally determined diad distribution over the calculated Bernoullian diad distribution of less than 1.07; and the storage modulus G' of said polymer, determined upon cooling as described herein, intersecting a value of 3.10 5 Pa at a temperature of less than 85 °C. The invention also describes polymerization processes suitable for the manufacture of these adhesive alpha-olefin inter-polymers.

Claims (33)

1. A poly-alpha olefin inter-polymer comprising A) from 60 to 94 % of units derived from one alpha mono-olefin having from 3 to 6 carbon atoms and B) from 6 to 40 mol % of units derived from one or more other mono-olefins having from 4 to 10 carbon atoms and at least one carbon atom more than A);
and C) optionally from 0 to 10 mol % of units derived from another copolymerizable unsaturated hydrocarbon, different from A) and B);
the diad distribution of component A in the polymer as determined by 13C NMR
as described herein showing a ratio of experimentally determined diad distribution over the calculated Bernoullian diad distribution of less than 1.07; and the storage modulus G' of said polymer, determined upon cooling as described herein, intersecting a value of 3.10 5 Pa at a temperature of less than 85 °C.
2. An inter-polymer according to claim 1 in which the content of B) combined with C) is at least 8 mol % and/or less than 40 mol % and the storage modulus G' of said polymer determined upon cooling as described herein, intersecting a storage modulus G' of 3.10 5 Pa at a temperature of less than 70 °C.
3. An inter-polymer according to claim 1 or claim 2 in which the reactivity ratio as determined by NMR as described herein, has a value of R A x R B, wherein R A
is the reactivity ratio of component A over component B and R B is the ratio of component B over component A, of less than 1.4.
4. An inter-polymer according to any of the preceding claims where the weight average molecular weight of the polymer as determined by GPC as described herein, is less than 120 000, preferably less than 90 000, and most preferably less than 70 000 and/or at least 20 000, preferably at least 30 000 and especially at least 40 000, the storage modulus G' of said polymer, determined upon cooling as described herein, intersecting a storage modulus G' of 3.10 5 Pascal at a temperature of less than 70 °C.
5. An inter-polymer according to any of the preceding claims in which A) is derived from units having from 3 to 6 carbon atoms and preferably propylene; B) is derived from units having from 4 to 8 carbon atoms, preferably at least two more carbon atoms than A), and is preferably butene-1, hexene-1 or octene-1, and C) is derived from ethylene.
6. An inter-polymer according to any of the preceding claims in which said polymer having a melting behavior as determined by DSC, as described herein, wherein the major peak melting point varies with content of component B) plus C) so that T m (interpolymer) is less than 153 - 2.78 x [C B+C] for any given concentration of B) and/or C) components. Where T m is the major melting peak of the interpolymer at a given content of components B) and C) in mol %; [C B-C] is the mol % of component B) plus C).
7. An inter-polymer according to any of the preceding claims in which there are at least 65 mol %, preferably at least 75 mol % of units derived from A) and/or no more than 94 mol %, preferably no more than 90 mol % of A); at least 6 mol %, preferably at least 10 mol % of B) and/or no more than 30 mol %, preferably no more than 25 mol % of B); and/or no more than 5 mol %, most preferably no more than 2 mol % of C).
8. An inter-polymer according to any of the preceding claims which has a heat of fusion of at least 5 J/g, preferably at least 10 J/g and/or no more than 40 J/g, preferably no more than 30 J/g, and most preferably no more than 20 J/g as determined by DSC as described herein.
9. An inter-polymer according to any of the preceding claims which has a major melting peak as determined by DSC, as described herein, of at least 40 °C, preferably of at least 50 °C and/or has a melting point as determined by DSC of no more than 130 °C, preferably no more than 90 °C .
10. An inter-polymer according to any of the preceding claims which has a Tg determined by DSC, as described herein, of no more than minus 5 °C, preferably no more than minus -15 °C, and/or at least minus 40 °C, preferably at least minus 30 °C.
11. An inter-polymer according to any of the preceding claims which G' at 120 °C is not greater than 1000 Pascal, preferably not greater than 500 Pascal and most preferably no greater than 100 Pascal.
12. An inter-polymer according to any of the preceding claims having an Mw/Mn as determined by GPC, as described herein, of from 1.5 to 4, more preferably less than 3, most preferably less than 2.2 and/or at least 1.6.
13. A poly-alpha olefin inter-polymer having (I) A) from 60 to 94 % of units derived from one alpha mono-olefin having from 3 to 6 carbon atoms and B) from 6 to 40 mol % of units derived from one or more other mono-olefins having from 4 to 10 carbon atoms and at least one carbon atom more than A);
and C) optionally from 0 to 10 mol % of units derived from another copolymerizable unsaturated hydrocarbon, different from A) and B);
the diad distribution of component A in the polymer as determined by 13C NMR
as described herein showing a ratio of experimentally determined diad distribution over the calculated Bernoullian diad distribution of less than 1.07;
and said polymer having a melting behavior as determined by DSC, as described herein, so that T m (interpolymer) is less than 153 - 2.78 x [C B+C] for any given concentration of B) and/or C) components where T m is the major melting peak of the interpolymer at a given content of components B) and C) in mol %; [C B+C]
is the mol % of component B) plus C).
14. An interpolymer according to claim 13 in which the storage modulus G' of said polymer, determined upon cooling as described herein, intersecting a value of 3.10 5 Pascal at a temperature of less than 85 °C.
15. An inter-polymer according to any of the preceding claims 13 or 14 which the content of B) combined with C) is at least 8 mol % and/or less than 40 mol %
and the storage modulus G' of said polymer, determined upon cooling as described herein, intersecting a storage modulus G' of 3.10 5 Pascal at a temperature of less than 70 °C.
16. An inter-polymer according to any of the preceding claims 13 to 15 in which the reactivity ratio as determined by NMR as described herein, has a value of R A
x R B, wherein R A is the reactivity ratio of component A over component B and R B is the ratio of component B over component A, of less than 1.4.
17. An inter-polymer according to any of the preceding claims 13 to 16 in which the weight average molecular weight of the polymer as determined by GPC as described herein, is less than 120 000, preferably less than 90 000, and most preferably less than 70 000 and/or at least 20 000, preferably at least 30 000 and especially at least 40 000, the storage modulus G' of said polymer, determined upon cooling as described herein, intersecting a storage modulus G' of 3.10 5 Pascal at a temperature of less than 70 °C.
18. An inter-polymer according to any of the preceding claims 13 to 17 in which A) is derived from units having from 3 to 6 carbon atoms and preferably propylene;
B) is derived from units having from 4 to 8 carbon atoms, preferably at least two more carbon atoms than A), and is preferably butene-1, hexene-1 or octene-1 and C) is derived from ethylene.
19. An inter-polymer according to any of the preceding claims 13 to 18 in which there are at least 65 mol %, preferably at least 75 mol of units derived from A) and/or no more than 94 mol %, preferably no more than 90 mol % of A); at least 6 mol %, preferably at least 10 mol % of B) and/or no more than 30 mol %, preferably no more than 25 mol % of B); and/or no more than 5 mol %, most preferably no more than 2 mol % of C).
20. An inter-polymer according to any of the preceding claims 13 to 19 which has a heat of fusion of at least 5 J/g, preferably at least 10 J/g and/or no more than 40 J/g, preferably no more than 30 J/g, and most preferably no more than 20 J/g as determined by DSC as described herein.
21. An inter-polymer according to any of the preceding claims 13 to 20 which has a melting peak as determined by DSC of at least 40 °C, preferably of at least 50 °C
and/or has a melting point as determined by DSC of no more than 130 °C, preferably no more than 95 °C.
22. An inter-polymer according to any of the preceding claims 13 to 21 which has a Tg determined by DSC of no more than minus 5 °C, preferably no more than minus 20 °C, and/or at least minus 40 °C, preferably at least minus 30 °C.
23. An inter-polymer according to any of the preceding claims 13 to 22 which the G' at 120 °C is not greater than 1000 Pascal, preferably not greater than 500 Pascal;
and most preferably no greater than 100 Pascal.
24. An inter-polymer according to any of the preceding claims 13 to 23 having an Mw/Mn as determined by GPC as described herein of from 1.5 to 4, more preferably less than 3, most preferably less than 2.2 and/or at least 1.6.
25. An adhesive composition or formulation containing an inter-polymer according to any of the preceding claims 1 to 24 which is substantially free of volatile components, containing less than 20 wt %, preferably less than 10 wt % of tackifier and optionally less than 3 wt % each of anti-oxidant, flow improver, wax, or crystallization aid.
26. An adhesive composition or formulation according to claim 25 further comprising from 1 to 20 wt % of a tackifier and/or from 1 to 20 wt % of a flow improver.
27. An adhesive composition or formulation according to claim 25 or 26 for use as a hot melt adhesive in which the Melt Index is from 1 to 2000 as determined under ASTM D1238 methods.
28. An adhesive composition or formulation according to any of claims 25 to 27 having a flowability of at least and being suitable for applying the adhesive composition by spraying.
29. An adhesive composition or formulation according to claim 28 or 31 for use as a pressure sensitive adhesive in which the Melt Index is from 0.1 to 200 as determined under ASTM D1238 method.
30. An adhesive composition or formulation containing an inter-polymer according to any of the preceding claims 1 to 24 which contains at least 10 wt %, preferably at least 20 wt % of the total weight of the formulation and no more than 90 wt %
of a hydrocarbon based volatile solvent, preferably no more than 60 wt % of the total weight of the formulation.
31. A packaging material or article containing a structure, elements of which are adhered by an adhesive composition or formulation according to any of claims to 30.
32. A hygienic garment containing a structure, elements of which are adhered by an adhesive composition or formulation according to any of claims 25 to 30.
33. An process for adhering two substrates together which process comprises (I) applying a poly-alpha olefin inter-polymer having A) from 55 to 94 % of units derived from one alpha mono-olefin having from 3 to 6 carbon atoms and B) from 6 to 45 mol % of % of units derived from one or more other mono-olefins having from 4 to 10 carbon atoms and at least one carbon atom more than A); and C) optionally from 0 to 10 mol % of units derived from another copolymerizable unsaturated hydrocarbon, different from A) and B) the diad distribution of component A in the polymer as determined by 13C
NMR as described herein showing a ratio of experimentally determined diad distribution over the calculated Bernoullian diad distribution of less than 1.07 (II) to the interface between the substrate at elevated temperature of from 10 to 100 °C and/or pressure until adhesion is established.
CA002414498A 1999-12-21 2000-12-21 Adhesive alpha-olefin inter-polymers Expired - Fee Related CA2414498C (en)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
US17171599P 1999-12-22 1999-12-22
US60/171,715 1999-12-22
US19909300P 2000-04-21 2000-04-21
US60/199,093 2000-04-21
PCT/US2000/035016 WO2001046278A2 (en) 1999-12-21 2000-12-21 Adhesive alpha-olefin inter-polymers

Publications (2)

Publication Number Publication Date
CA2414498A1 true CA2414498A1 (en) 2001-06-08
CA2414498C CA2414498C (en) 2009-12-08

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CA002395532A Abandoned CA2395532A1 (en) 1999-12-22 2000-12-21 Polypropylene-based adhesive compositions
CA002414498A Expired - Fee Related CA2414498C (en) 1999-12-21 2000-12-21 Adhesive alpha-olefin inter-polymers

Family Applications Before (1)

Application Number Title Priority Date Filing Date
CA002395532A Abandoned CA2395532A1 (en) 1999-12-22 2000-12-21 Polypropylene-based adhesive compositions

Country Status (13)

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US (4) US6747114B2 (en)
EP (3) EP1263815B1 (en)
JP (1) JP4966463B2 (en)
KR (1) KR100718424B1 (en)
CN (1) CN1333032C (en)
AT (1) ATE358144T1 (en)
AU (2) AU777944B2 (en)
BR (1) BR0016618B1 (en)
CA (2) CA2395532A1 (en)
DE (1) DE60034151T2 (en)
ES (1) ES2282158T3 (en)
MX (1) MXPA02006199A (en)
WO (2) WO2001046278A2 (en)

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