Multi-amine compound primers for bonding of polyolefins with cyanoacrylate adhesives
AssigneeLoctite Corporation
InventorsJohn G. Woods, Jean M. J. Fréchet
Life of this patent
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Abstract
Primers for cyanoacrylate adhesives which are based on compounds having multiple amine groups thereon (“multi-amines”) which have at least three secondary or tertiary amine groups, at least one of which is a tertiary amine group. The multi-amine compounds are characterized by having thereon at least three terminal and/or pendant aliphatic hydrocarbon groups of at least 4 carbon atoms in length. Such primers give substantially improved bond strengths to cyanoacrylate adhesive bonded assemblies comprising a polyolefin substrate such as high density polyethylene, LDPE or polypropylene. The multi-amine may have a cascade, dendrimer, hyperbranched or comb-like structure.
Claims36
A primer composition for anionically polymerizable monomer adhesives, the primer composition comprising a multi-amine compound in a volatile organic solvent, the multi-amine compound having at least three amine groups which are secondary or tertiary amine groups, at least one of said amine groups being a tertiary amine group, and the multi-amine compound further having at least three terminal and/or pendant aliphatic hydrocarbon groups thereon which are higher than C4.
A primer composition for anionically polymerizable monomer adhesives, the primer composition comprising a multi-amine compound in a volatile organic solvent, the multi-amine compound having at least three amine groups which are secondary or tertiarn amine groups, at least one of said amine groups being a tertiary amine group, the multi-amine compound further having at least three terminal and/or pendant C4 or higher aliphatic hydrocarbon groups thereon, and wherein said multi-amine compound is a linear or branched poly(alkyleneamine) polymer, a multi-amine cascade compound or an addition polymer or copolymer of an ethylenically unsaturated amine.
An adhesive composition obtained by bringing a multi-amine compound into contact with a formulation comprising an anionically polymerizable monomer of the formula:
- where X and Y are groups which are more strongly electron withdrawing than halo and A is H or CH2═CH—, the multi-amine compound having at least three amine groups which are secondary or tertiary amine groups, at least one of said amine groups being a tertiary amine group, and the multi-amine compound further having at least three terminal and/or pendant aliphatic hydrocarbon groups thereon which are higher than C4.
A cyanoacrylate adhesive composition obtained by bringing a multi-amine compound into contact with a formulation comprising an α-cyanoacrylate ester monomer, the multi-amine compound having at least three amine groups which are secondary or tertiary amine groups, at least one of said amine groups being a tertiary amine group, the multi-amine compound further having at least three terminal and/or pendant C4 or higher aliphatic hydrocarbon groups thereon, and wherein the multi-amine compound is a linear or branched poly(alkyleneamine) polymer, a multi-amine cascade compound or an addition polymer or copolymer of an ethylenically unsaturated amine.
A cured cyanoacrylate polymer obtained by bringing a multi-amine compound into contact with a composition comprising an α-cyanoacrylate ester monomer, the multi-amine compound being selected from the group consisting of linear or branched poly(alkyleneamine) polymers, multi-amine cascade compounds and addition polymers or copolymers of ethylenically unsaturated amines, and having at least three terminal and/or pendant C4 or higher alkyl groups.
A primer composition for anionically polymerizable monomer adhesives, the primer composition comprising a multi-amine compound of the formula:
- where R1 is —CH2CH2—or —CH2CH2CH2—;
- R2 is H or R3;
- the R3 groups are the same or different C4-C22 alkyl, C4-C22 alkenyl, carboxy-C4-C22-alkyl, carboxy-C4-C22-alkenyl or —CH2CH2C(═O)OR4 groups;
- and R4 is C4-C22 alkyl, and,
- linear or branched poly(alkylenimine) having at least three terminal and/or pendent groups defined as for R3.
A method of bonding a pair of substrates comprising applying a primer composition to at least one of said substrates, allowing the volatile organic solvent to evaporate, subsequently applying an α-cyanoacrylate monomer formulation to at least one of said substrates, and then joining the substrates until the adhesive fixtures, wherein
- the primer composition comprises a multi-amine compound in a volatile organic solvent, the multi-amine compound having at least three amine groups which are tertiary or secondary amine groups, at least one of said amine groups being a tertiary amine group, and the multi-amine compound further having at least three terminal and/or pendant C4 or higher aliphatic hydrocarbon groups thereon, and
- at least one of said substrates is a polyolefin.
Dependencies are inferred from the claim text.