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US 8,734,939 B2Granted
Thermally reversible hot melt adhesive composition containing multifunctional diene and dienophile compounds
AssigneeHenkel US IP LLC
InventorsDonald Herr, Laxmisha M. Sridhar, Andrew Slark
Life of this patent
Estimating the term…
Abstract
The invention relates to a thermally reversible hot melt adhesive that is isocyanate-free, moisture independent, crosslinkable and thermally reversible. The thermally reversible hot melt adhesive may be repeatedly heated and cooled without negatively affecting the performance of the adhesive. The thermally reversible composition may also be used as a primer layer. The thermally reversible hot melt adhesive and primer are particularly well suited for end use applications such as packaging, graphic arts, construction, footwear, textiles, general assembly, automotive and consumer goods.
Claims20
A thermally reversible hot melt adhesive comprising:
- a) at least one multifunctional diene monomer/prepolymer L-(X)P, wherein
- i) L is independently selected from the group consisting of a (poly)urethane, (poly)urea, (poly)ester having a plurality of repeating ester groups within the backbone, (poly)carbonate, (poly)amide, (poly)imide, (poly)styrene, (poly)ether having a plurality of repeating O atoms within the backbone, (poly)(meth)acrylate, (poly)olefin, (poly)siloxane, copolymers of above, including copolymers of maleic anhydride, and mixtures thereof;
- ii) X is a diene containing one or more of acyclic 1,3-diene, cyclopentadiene, cyclohexadiene, furan, fulvene, pyrrole, naphthalene and anthracene;
- and
- iii) P is greater than zero;
- b) at least one multifunctional dienophile prepolymer L-(Y)Q having a molecular weight greater than 1,000 g/mol, wherein
- i) L is independently selected from the group consisting of a (poly)urethane, (poly)urea, (poly)ester, (poly)carbonate, (poly)amide, (poly)styrene, aliphatic (poly)ether, (poly)(meth)acrylate, (poly)olefin, (poly)siloxane, copolymers of above, including copolymers of maleic anhydride, or mixtures thereof;
- and
- ii) Y is a dienophile containing one or more of a maleimide, isomaleimide, citraconimide, itaconimide, maleate, fumarate, acrylate, methacrylate, cyanoacrylate, benzoquinone, benzoquinone oxime, benzoquinone imine, naphthaquinone, alkylidene malonate, alkyne containing electron withdrawing groups and mixtures thereof;
- and
- iii) Q is greater than zero;
- and
- wherein at least one of P or Q has a value greater than 2.0.
10 more elements
A thermally reversible hot melt adhesive comprising:
- a) at least one multifunctional diene monomer/prepolymer L-(X)P, wherein
- i) L is independently selected from the group consisting of a (poly)urethane, (poly)urea, (poly)ester, (poly)carbonate, (poly)amide, (poly)imide, (poly)styrene, (poly)ether, (poly)(meth)acrylate, (poly)olefin, (poly)siloxane, copolymers of above, including copolymers of maleic anhydride, and mixtures thereof;
- ii) X is a diene containing one or more of acyclic 1,3-diene, cyclopentadiene, cyclohexadiene, furan, fulvene, pyrrole, naphthalene and anthracene;
- and
- iii) P is greater than zero;
- b) at least one multifunctional dienophile prepolymer L-(Y)Q having a molecular weight greater than 1,000 g/mol, wherein
- i) L is independently selected from the group consisting of a (poly)urethane, (poly)urea, (poly)ester, (poly)carbonate, (poly)amide, (poly)imide, (poly)styrene, (poly)ether, (poly)(meth)acrylate, (poly)olefin, (poly)siloxane, copolymers of above, including copolymers of maleic anhydride, or mixtures thereof;
- and
- ii) Y is a dienophile containing one or more of a maleimide, isomaleimide, citraconimide, itaconimide, maleate, fumarate, acrylate, methacrylate, cyanoacrylate, benzoquinone, benzoquinone oxime, benzoquinone imine, naphthaquinone, alkylidene malonate, alkyne containing electron withdrawing groups and mixtures thereof;
- and
- iii) Q is greater than zero;
- wherein at least one of P or Q has a value greater than 2.0 and at least one multifunctional diene monomer/prepolymer is
- or a combination thereof.
10 more elements
A thermally reversible hot melt adhesive comprising:
- a) at least one multifunctional diene monomer/prepolymer L-(X)P, wherein
- i) L is independently selected from the group consisting of a (poly)urethane, (poly)urea, (poly)ester, (poly)carbonate, (poly)amide, (poly)imide, (poly)styrene, (poly)ether, (poly)(meth)acrylate, (poly)olefin, (poly)siloxane, copolymers of above, including copolymers of maleic anhydride, and mixtures thereof;
- ii) X is a diene containing one or more of acyclic 1,3-diene, cyclopentadiene, cyclohexadiene, furan, fulvene, pyrrole, naphthalene and anthracene;
- and
- iii) P is greater than zero;
- b) at least one multifunctional dienophile prepolymer L-(Y)Q having a molecular weight greater than 1,000 g/mol, wherein
- i) L is independently selected from the group consisting of a (poly)urethane, (poly)urea, (poly)ester, (poly)carbonate, (poly)amide, (poly)imide, (poly)styrene, (poly)ether, (poly)(meth)acrylate, (poly)olefin, (poly)siloxane, copolymers of above, including copolymers of maleic anhydride, or mixtures thereof;
- and
- ii) Y is a dienophile containing one or more of a maleimide, isomaleimide, citraconimide, itaconimide, maleate, fumarate, acrylate, methacrylate, cyanoacrylate, benzoquinone, benzoquinone oxime, benzoquinone imine, naphthaquinone, alkylidene malonate, alkyne containing electron withdrawing groups and mixtures thereof;
- and
- iii) Q is greater than zero;
- wherein at least one of P or Q has a value greater than 2.0 and at least one multifunctional dienophile monomer/prepolymer is
- wherein the molecular weight of the polyester polyol segment is from about 2000 to about 7000,
- wherein the molecular weight of the polyether polyol segment is from about 1000 to 18,000, or a combination thereof.
11 more elements
A thermally reversible hot melt adhesive comprising:
- a) at least one multifunctional diene monomer/prepolymer L-(X)P, wherein
- i) L is independently selected from the group consisting of a (poly)urethane, (poly)urea, (poly)ester, (poly)carbonate, (poly)amide, (poly)imide, (poly)styrene, aliphatic (poly)ether, (poly)(meth)acrylate, (poly)olefin, (poly)siloxane, copolymers of above, including copolymers of maleic anhydride, and mixtures thereof;
- ii) X is a diene containing one or more of acyclic 1,3-diene, cyclopentadiene, cyclohexadiene, furan, fulvene, pyrrole, naphthalene and anthracene;
- and
- iii) P is greater than zero;
- b) at least one multifunctional dienophile prepolymer L-(Y)Q, wherein
- i) L is independently selected from the group consisting of a (poly)urethane, (poly)urea, (poly)ester, (poly)carbonate, (poly)amide, (poly)imide, (poly)styrene, (poly)ether, (poly)(meth)acrylate, (poly)olefin, (poly)siloxane, copolymers of above, including copolymers of maleic anhydride, or mixtures thereof;
- and
- ii) Y is a dienophile containing one or more of a maleimide, isomaleimide, citraconimide, itaconimide, maleate, fumarate, acrylate, methacrylate, cyanoacrylate, benzoquinone, benzoquinone oxime, benzoquinone imine, naphthaquinone, alkylidene malonate, alkyne containing electron withdrawing groups and mixtures thereof;
- and
- iii) Q is greater than zero;
- and
- wherein at least one of P or Q has a value greater than 2.0;
- and
- c) a poly(meth)acrylate polymer.
12 more elements
An article, comprising:
- a substrate;
- a layer of thermally reversible primer bonded to the substrate;
- and
- a layer of adhesive different from the primer bonded to the primer, wherein the primer comprises:
- a) at least one multifunctional diene monomer/prepolymer L-(X)P, wherein
- i) L is selected from the group consisting of (poly)urethane, (poly)urea, (poly)ester, (poly)carbonate, (poly)amide, (poly)imide, (poly)styrene, (poly)ether, (poly)(meth)acrylate, (poly)olefin, (poly)siloxane, copolymers of above, including copolymers of maleic anhydride, and mixtures thereof;
- and
- ii) X is a diene containing one or more of acyclic 1,3-diene, cyclopentadiene, cyclohexadiene, furan, fulvene, pyrrole, naphthalene and anthracene;
- and
- iii) P is greater than zero;
- b) at least one multifunctional dienophile monomer/prepolymer L-(Y)Q having a molecular weight greater than 1,000 g/mol, wherein
- i) L is selected from the group consisting of a (poly)urethane, (poly)urea, (poly)ester, (poly)carbonate, (poly)amide, (poly)imide, (poly)styrene, (poly)ether, (poly)(meth)acrylate, (poly)olefin, (poly)siloxane, copolymers of above, including copolymers of maleic anhydride, and mixtures thereof;
- and
- ii) Y is a dienophile containing one or more of a maleimide, isomaleimide, citraconimide, itaconimide, maleate, fumarate, acrylate, methacrylate, cyanoacrylate, benzoquinone, benzoquinone oxime, benzoquinone imine, naphthaquinone, alkylidene malonate, alkyne containing electron withdrawing groups and mixtures thereof;
- and
- iii) Q is greater than zero;
- and
- c) optionally, a solvent
- wherein the average P value for a) is greater than 2.1, or the average Q value for b) is greater than 2.1, or the average P value for a) is greater than 2.1 and the average Q value for b) is greater than 2.1.
16 more elements
A compound selected from:
- wherein the molecular weight of the polyester polyol segment is from about 2000 to about 7000, and
- wherein the molecular weight of the polyether polyol segment is from about 1000 to 18,000.
Dependencies are inferred from the claim text.