EP1745094A4 - Hot-melt adhesive compositions based on olefin co-polymers - Google Patents
Hot-melt adhesive compositions based on olefin co-polymersInfo
- Publication number
- EP1745094A4 EP1745094A4 EP05747477A EP05747477A EP1745094A4 EP 1745094 A4 EP1745094 A4 EP 1745094A4 EP 05747477 A EP05747477 A EP 05747477A EP 05747477 A EP05747477 A EP 05747477A EP 1745094 A4 EP1745094 A4 EP 1745094A4
- Authority
- EP
- European Patent Office
- Prior art keywords
- composition
- polymer
- composition according
- weight
- component
- 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.)
- Withdrawn
Links
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
- C09J123/10—Homopolymers or copolymers of propene
- C09J123/12—Polypropene
-
- 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
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F10/00—Homopolymers and copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
- C08F10/04—Monomers containing three or four carbon atoms
- C08F10/06—Propene
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/13—Phenols; Phenolates
- C08K5/134—Phenols containing ester groups
- C08K5/1345—Carboxylic esters of phenolcarboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/49—Phosphorus-containing compounds
- C08K5/51—Phosphorus bound to oxygen
- C08K5/52—Phosphorus bound to oxygen only
- C08K5/524—Esters of phosphorous acids, e.g. of H3PO3
-
- 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
-
- 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
- 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
- C08F210/08—Butenes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
- C08K5/005—Stabilisers against oxidation, heat, light, ozone
-
- 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
Definitions
- the present invention relates generally to polyolefin polymers and their end uses.
- the adhesives are hot-melt adhesive comprising propylene co-
- components such as polymer (typically SIS, SBS or SEBS block co-polymers), resins,
- Adhesives produced by formulation and blending of such a wide range of materials are
- polyolefin based hot-melt adhesives have been disclosed in a number of patents, including
- polyolefins including polypropylene and polyethylene film, polypropylene non-woven, SPA DEX® elastics and other elastic
- US 2002/0123726 discloses an adhesive composition comprising blend of an isotactic polypropylene and an atactic polypropylene. The composition was claimed to have certain improved performance properties in making elastic composite laminates.
- WO 97/39075 discloses an adhesive composition comprising blend of a polybutene, a polyolefin co-polymer, a tackifier resin, a plasticizer, a wax as viscosity reducer, and a stabilizer. Again, it is apparent to those skilled in the art that the usefulness of the said composition as elastic attachment adhesive would be very limited due to its
- FIG. 1 shows the relationship between the crystallinity of a finished polymer and the
- FIG. 2 shows methods known in the art for applying a polymer according to the present
- the present invention provides a composition of matter useful as an adhesive, which comprises four components.
- the first component is a polypropylene component, which is present in any amount between about 30% to about 90% by weight, based on the total weight of the composition.
- the polypropylene component may comprise a polypropylene homopolymer, a polypropylene co-polymer, or any mixtures of any two or more polypropylene homopolymers or polypropylene co-polymers, or a mixture comprising a polypropylene homopolymer and a polypropylene copolymer.
- the second component is a tackifier resins component, present in any amount between about 10% to about 60% by weight, based on the total weight of the composition.
- the third component is a functionalized polymer component present in any amount between about 0 % to about 40% by weight, based on the total weight of the composition.
- the fourth component is a stabilizer(s) component, present in any amount between about 0.01% to about 1% by weight, based on the total weight of said composition.
- the invention is directed to hot-melt adhesive compositions, which are useful for, inter alia, bonding non-woven elastic composites.
- Compositions of the invention are particularly well-suited for use employing application techniques where the adhesive is applied in such a manner that it forms "point bonding" between elastic strands and substrates.
- an adhesive according to the invention can be applied in a swirl pattern onto the pre-stretched elastic strands, then laminated with substrates to form the elastic composites.
- the present invention provides a novel, economic path to produce polyolefin based hot-melt adhesives.
- the hot-melt adhesive compositions of this disclosure comprise a propylene copolymer, a tackifier resin, a functionalized polyolefin, and one or more polymer stabilizers.
- the compositions possess performance properties that make them particularly useful in elastic attachment applications for disposable, non-woven articles, such as diapers.
- the compositions of the invention also provide improvement in certain physical properties, such as heat stability, as compared to the conventional styrenic block co-polymer-based adhesives currently used in these applications.
- formulations which include expensive non-polyolefin components, typically including styrenic block co-polymers such as SIS, SBS or SEBS, resins or tackifiers, oil or waxes, and other additives, to achieve the balanced properties.
- styrenic block co-polymers such as SIS, SBS or SEBS
- resins or tackifiers oil or waxes, and other additives
- a composition provided hereby comprises: a) 30% to 90% by weight of a propylene co-polymer; b) 10% to 60% by weight of tackifier resins); c) 0% to 40%) by weight of a functionalized polymer; and d) 0.01% to 1% by weight of stabilizer(s).
- the Propylene Co-polymer Component The propylene co-polymer is a co-polymer of propylene with another alpha-olefin comonomer selected from C 2 or C 4 - C 20 alkenes.
- the preferred comonomers are 1- butene, 1-hexene and 1-octene.
- the most preferred comonomer is 1-butene.
- the content of co-monomer in the propylene co-polymer is about 0% to 60% by weight, preferably 15% to 50%o by weight, most preferably 25% to 45% by weight.
- the propylene co-polymer should have a low degree of crystallinity as measured by
- the heat of fusion as measured by DSC according ASTM method D-3417 should be about 0 to 50 J/g, preferably 5 to 20 J/g.
- the propylene co-polymer has a weight-average molecular weight, as measured by Gel Permeation Chromatography (GPC), of 10,000 to 1,000,000, preferably 30,000 to 100,000, most preferably 40,000 to 80,000.
- GPC Gel Permeation Chromatography
- the propylene co-polymer can be synthesized by Ziegler-Natta catalysts or metallocene catalysts.
- Ziegler-Natta catalysts are well-known to those skilled in the art and generally refer to a type of catalysts that comprise a mixture of a base metal alkyl of the groups I to III metals, and a transition metal salt of groups IV to VIII metals of the periodic table of the elements.
- a Ziegler-Natta catalyst is basically a complex derived from a halide of a transition metal, for example, titanium, chromium or vanadium with a metal alkyl that is typically an organoaluminum compound.
- Typical advanced Ziegler- Natta catalysts are usually comprised of a titanium halide supported on a magnesium compound.
- Metallocene catalysts are well-known to those skilled in the art to include in its structure at least one cyclopentadienyl ligand coordinated to a transition metal.
- the preferred catalyst used to produce the propylene co-polymer of the present invention is a Ziegler-Natta catalyst.
- the propylene co-polymer can be produced in conventional polyolefin manufacturing processes including gas phase, slurry, bulk and solution processes in either batch or continuous mode. These processes are widely used in polyolefin industry and well-known to those skilled in the art.
- the preferred process is a "liquid pool" bulk polymerization process in which the polymerization reaction is carried out in the medium
- the invention provides a composition that includes one or more tackifier resins.
- the tackifier resin must be compatible with the
- propylene co-polymer and can effectively promote the specific adhesion of the composition. While most commercial tackifier resins such as those derived from hydrocarbons, rosin, rosin esters, synthetic poly-terpenes and natural terpenes can be used,
- the preferred tackifiers are aliphatic hydrocarbon resins that are found to have the best
- blend is about 5 to about 60% by weight, preferably about 15 to about 30% by weight.
- the invention provides a composition that
- the functionalized polymer is used to promote the
- the functionalized polymer must be
- functionalized polymers are those having polyolefin backbone co-polymerized or grafted
- polymers are low molecular weight polypropylenes grafted with maleic anhydride.
- composition according to the invention also preferably includes one or more
- suitable stabilizer(s) present in the range of 0.01%> to 1% by weight, based on the total
- hindered phenols or combinations of hindered phenols and phosphates are hindered phenols or combinations of hindered phenols and phosphates. These stabilizers are commonly used in polyolefins, and are well-known to those skilled in
- the adhesive composition including all the components, is preferably mixed at an
- elevated temperature in the range of between about 300°F to 400° F by any suitable means
- a final adhesive compositions has a melt
- melt viscosity measured at 375° C of about 1,000 to 20,000 cps.
- melt viscosity measured at 375° C of about 1,000 to 20,000 cps.
- melt viscosity is between about 2,000 to 8,000 cps. More preferably the melt viscosity is between about
- the adhesive composition should be any suitable material. According to a preferred form of the invention, the adhesive composition should be any suitable material. According to a preferred form of the invention, the adhesive composition should be any suitable material.
- tensile strength 50 to 400 psi, preferably 100 to 300 psi, and tensile elongation of
- VTDV-I VTDV-I in accordance with the ASTM D-3236. Needle Penetration (NP), a measurement of hardness, was measured at room
- the melting point and the heat of fusion were measured by Differential Scanning
- Creep Resistance is a test to measure the ability of an adhesive to withstand the
- Test specimen was prepared by applying an
- a Ziegler-Natta catalyst may be prepared as follows: 30 g (0.315 mole) of MgCl 2 was
- Mg:Al:Ti molar ratio was about 8:1:0.5.
- catalyst poisons such as moisture and oxygen, prescribed amount of catalyst (table 1) was
- TEAL triethylaluminum
- Figure 1 illustrates an effective way to control the crystallinity of polymer at given comonomer
- VECTOR® 4211 resin is a linear SIS block co-polymer supplied by ExxonMobil
- ESCOREZ® 5400 and 5415 resins are hydrogenated dicyclopentadiene
- tackifying resins produced by ExxonMobil.
- ENDEX® 160 resin is a alpha-methyl styrene tacldfying resin produced by Hercules Chemical Company.
- EPOLENE® E-43 wax is a maleated polypropylene wax supplied by Eastman Chemical Company.
- EPOLENE® N-15 wax is a polypropylene wax supplied by Eastman Chemical Company.
- IRGANOX® 1010 anti-oxidant is a phenol antioxidant
- IRGAFOS® 168 anti-oxidant is a phosphite antioxidant.
- Comparative example A is a conventional adhesive composition disclosed in US Patent 6,531,544.
- Table 4 shows the results of creep test on the laminates prepared using several
- Example 6 represents the preferred embodiment of the present invention
- Examples 7-9 are not presently viewed as performing particularly well, and are included herein to illustrate the effect of base polymer
Abstract
Description
Claims
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US57004804P | 2004-05-11 | 2004-05-11 | |
US57430604P | 2004-05-25 | 2004-05-25 | |
PCT/US2005/016250 WO2005111132A1 (en) | 2004-05-11 | 2005-05-09 | Hot-melt adhesive compositions based on olefin co-polymers |
Publications (2)
Publication Number | Publication Date |
---|---|
EP1745094A1 EP1745094A1 (en) | 2007-01-24 |
EP1745094A4 true EP1745094A4 (en) | 2009-02-25 |
Family
ID=38050921
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP05747477A Withdrawn EP1745094A4 (en) | 2004-05-11 | 2005-05-09 | Hot-melt adhesive compositions based on olefin co-polymers |
Country Status (4)
Country | Link |
---|---|
EP (1) | EP1745094A4 (en) |
KR (1) | KR20070057085A (en) |
MX (1) | MXPA06012993A (en) |
WO (1) | WO2005111132A1 (en) |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US8076407B2 (en) | 2008-02-08 | 2011-12-13 | Henkel Ag & Co. Kgaa | Hot melt adhesive |
US8623480B2 (en) | 2011-06-27 | 2014-01-07 | H. B. Fuller Company | Hot melt adhesive compositions including olefinic polymer blends and articles including the same |
US9593235B2 (en) | 2013-02-15 | 2017-03-14 | H.B. Fuller Company | Reaction product of propylene polymer and wax, graft copolymers derived from polypropylene polymer and wax, hot melt adhesive compositions including the same, and methods of using and making the same |
US9267060B2 (en) | 2013-02-15 | 2016-02-23 | H.B. Fuller Company | Reaction product of propylene polymer and wax, graft copolymers derived from polypropylene polymer and wax, hot melt adhesive compositions including the same, and methods of using and making the same |
BR112017020862A2 (en) * | 2015-04-17 | 2018-07-10 | Henkel IP & Holding GmbH | hot melt adhesives and their uses |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1989005334A1 (en) * | 1987-11-30 | 1989-06-15 | Eastman Kodak Company | Hot-melt adhesive composition |
US5441999A (en) * | 1993-10-15 | 1995-08-15 | Reichhold Chemicals, Inc. | Hot melt adhesive |
WO2002036704A1 (en) * | 2000-10-30 | 2002-05-10 | Gluco Limited | Amorphous polypropylene based adhesive |
WO2004039907A1 (en) * | 2002-10-28 | 2004-05-13 | Bostik Findley, Inc. | Hot melt adhesive composition based on a random copolymer of isotactic polypropylene and a secondary polymer |
WO2005047389A1 (en) * | 2003-11-04 | 2005-05-26 | Kimberly-Clark Worldwide Inc. | Tackified amorphous-poly-alpha-olefin-bonded structures |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE19504425A1 (en) * | 1995-02-10 | 1996-08-14 | Hella Kg Hueck & Co | Hot melt adhesives for vehicle lights and vehicle headlights |
US5685758A (en) * | 1996-04-12 | 1997-11-11 | National Starch And Chemical Investment Holding Corporation | Hot melt adhesive compositions with improved wicking properties |
ES2282158T3 (en) * | 1999-12-21 | 2007-10-16 | Exxonmobil Chemical Patents Inc. | ADHESIVE ALPHA-OLEFINE INTERPOLIMEROS. |
US6329468B1 (en) * | 2000-01-21 | 2001-12-11 | Bostik Findley, Inc. | Hot melt adhesive based on semicrystalline flexible polyolefins |
-
2005
- 2005-05-09 EP EP05747477A patent/EP1745094A4/en not_active Withdrawn
- 2005-05-09 MX MXPA06012993A patent/MXPA06012993A/en unknown
- 2005-05-09 WO PCT/US2005/016250 patent/WO2005111132A1/en active Application Filing
- 2005-05-09 KR KR1020067025959A patent/KR20070057085A/en not_active Application Discontinuation
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1989005334A1 (en) * | 1987-11-30 | 1989-06-15 | Eastman Kodak Company | Hot-melt adhesive composition |
US5441999A (en) * | 1993-10-15 | 1995-08-15 | Reichhold Chemicals, Inc. | Hot melt adhesive |
WO2002036704A1 (en) * | 2000-10-30 | 2002-05-10 | Gluco Limited | Amorphous polypropylene based adhesive |
WO2004039907A1 (en) * | 2002-10-28 | 2004-05-13 | Bostik Findley, Inc. | Hot melt adhesive composition based on a random copolymer of isotactic polypropylene and a secondary polymer |
WO2005047389A1 (en) * | 2003-11-04 | 2005-05-26 | Kimberly-Clark Worldwide Inc. | Tackified amorphous-poly-alpha-olefin-bonded structures |
Non-Patent Citations (1)
Title |
---|
See also references of WO2005111132A1 * |
Also Published As
Publication number | Publication date |
---|---|
EP1745094A1 (en) | 2007-01-24 |
WO2005111132A8 (en) | 2007-05-24 |
KR20070057085A (en) | 2007-06-04 |
WO2005111132A1 (en) | 2005-11-24 |
MXPA06012993A (en) | 2008-03-11 |
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Legal Events
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Inventor name: SUN, LIXIN Inventor name: HASELMAN, JIM Inventor name: BUENACOSA, ENRICO, L. |
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RIN1 | Information on inventor provided before grant (corrected) |
Inventor name: HASELMAN, JIM Inventor name: SUN, LIXIN Inventor name: BUENACOSA, ENRICO, L. |
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DAX | Request for extension of the european patent (deleted) | ||
A4 | Supplementary search report drawn up and despatched |
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17Q | First examination report despatched |
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STAA | Information on the status of an ep patent application or granted ep patent |
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18D | Application deemed to be withdrawn |
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