Curable hybrid electron donor compounds containing vinyl ether

Details Curable hybrid electron donor compounds containing vinyl ether Curable hybrid electron donor compounds containing vinyl ether

2000-05-18

2001-10-23

Dawson, Robert (Department: 1712)

Synthetic resins or natural rubbers -- part of the class 520 ser

Synthetic resins

From reactant having at least one -n=c=x group as well as...

C528S032000, C528S045000, C528S059000, C528S272000, C526S335000, C568S606000, C568S027000, C568S028000, C568S038000, C568S308000, C568S579000, C558S254000, C560S330000, C564S017000, C564S032000, C564S047000

Reexamination Certificate

active

06307001

ABSTRACT:

FIELD OF THE INVENTION
This invention relates to electron donor compounds containing a vinyl ether group and to curable adhesive compositions containing those electron donor compounds.
BACKGROUND OF THE INVENTION
Adhesive compositions, particularly conductive adhesives, are used for a variety of purposes in the fabrication and assembly of semiconductor packages and microelectronic devices. The more prominent uses are the bonding of integrated circuit chips to lead frames or other substrates, and the bonding of circuit packages or assemblies to printed wire boards.
There exist electron acceptor/donor adhesives for use in low modulus adhesives, particularly in fast-cure adhesives for die attach applications in which vinyl ethers are the electron donors. However, the number of suitable vinyl ethers as donors is limited due to their low boiling points, high volatility, and difficult preparations. Thus, there is a need for the development of new electron donors for use in adhesives applications.
SUMMARY OF THE INVENTION
This invention relates to hybrid electron donor compounds comprising a vinyl ether and a carbon to carbon double bond external to an aromatic ring and conjugated with the unsaturation in the aromatic ring attached to a molecular (small molecule) or polymeric group. The presence of the vinyl ether group provides lower viscosity to these compounds compared to electron donor compounds that do not have the vinyl ether group; using a difunctional hybrid electron donor compound as an example, the hybrid will have a lower viscosity than the corresponding difunctional electron donor compound having the same electron donor group as each functionality.
The activity of the electron donor functionality other than the vinyl ether group can be increased by adding electron donating substituents on the aromatic ring, or decreased by adding electron withdrawing substituents. The activity can also be varied by steric interaction. An increase in the number or size of alkyl substituents on the carbon to carbon double bond will decrease the reactivity. Preferably, any substituents on the carbon to carbon double bond will be hydrogen, or will be hydrogen with a methyl group as the only other substituent.
Each electron donor group of the hybrid is linked to the molecular or polymeric entity through a linking group that is the product of the reaction between a functionality on the electron donor group and a co-reactive functionality on the molecular or polymeric group. Alternatively, the electron donor group may be attached to the molecular or polymeric group through a coupling reaction in which the carbon to carbon double bond external to the aromatic ring (of the electron donor) is formed during the reaction.
The molecular or polymeric group may be a cyclic, branched or linear alkyl, a siloxane or polysiloxane, a C
1
to C
4
alkoxy-terminated siloxane or polysiloxane, a polyether, a polyester, a polyurethane, a (poly)butadiene, or an aromatic, polyaromatic, or heteroaromatic group.
This invention is also a curable composition comprising one or more of the inventive electron donor compounds, and optionally a curing agent and one or more fillers.
This invention is also a curable composition comprising one or more of the inventive electron donor compounds and one or more co-polymerizable electron acceptor compounds, and may contain a curing agent and one or more fillers. Suitable electron acceptor compounds for co-polymerization are fumarates and maleates, for example, dioctyl maleate, dibutyl maleate, dioctyl fumarate, dibutyl fumarate. Resins or compounds containing acrylate and maleimide functionality are other suitable electron acceptor materials.
DETAILED DESCRIPTION OF THE INVENTION
The electron donor compounds of this invention will have one of the structures depicted here:
Structure I:
Structure II:
in which
m and n are 1 to 6, preferably 1 to 3, and more preferably 1;
Ar is an aromatic or heteroaromatic ring having 3 to 10 carbon atoms within the ring, in which the heteroatoms may be N, O, or S;
R
1
, R
2
, and R
3
are independently hydrogen, Ar as described above, or an alkyl group having 1 to 12 carbon atoms; preferably R
1
, R
2
, and R
3
are hydrogen or an alkyl group having 1 to 4 carbon atoms, and more preferably are all hydrogen;
R
4
, R
5
, and R
6
are independently hydrogen, a methyl group or an ethyl group, and preferably two of R
4
, R
5
, and R
6
are hydrogen and one is methyl, and more preferably all are hydrogen;
G is—OR
7
, —SR
7
, —N(R
1
)(R
2
), Ar as described above, or an alkyl group having 1 to 12 carbon atoms, in which R
7
is Ar as described above, or an alkyl group having 1 to 12 carbon atoms, preferably 1 to 4 carbon atoms, and R
1
and R
2
are as described above;
Q is an alkyl group having 1 to 12 carbon atoms;
X is
Z is an alkyl group, a siloxane, a polysiloxane, a C
1
to C
4
alkoxy-terminated siloxane or polysiloxane, a polyether, a polyester, a polyurethane, a (poly)butadiene, or an aromatic, polyaromatic, or heteroaromatic group. Materials for preparation as the Z group in these compounds are commercially available from a number of sources; for example, aromatic and polyaromatic materials may be obtained from BASF or Bayer; siloxanes and polysiloxanes from Gelest; polyethers from BASF; polyesters from Uniqema or Bayer; poly(butadiene)s from Elf-Atochem; polyurethanes from Bayer or BASF; and alkanes from Uniqema. Some of these sources will have available Z materials already functionalized for reaction with a co-reactive functionality on the vinyl ether or other electron donor starting material; in other cases, the practitioner will need to functionalize the materials in preparation for reaction with the electron donor containing starting material.
The Z groups may contain cyclic moieties or heteroatoms, and may contain pendant hydroxyl or thiol groups depending on the synthetic route for making the electron donor compound; for example, if one of the starting compounds contains a hydroxyl or thiol functionality that is reacted with an epoxy functionality, the Z group will contain a pendant hydroxyl or thiol group.
The exact composition or molecular weight of Z is not critical to the invention and can range widely depending on the requirements of the end use for the hybrid electron donor compound. The composition of Z can be chosen to give specific material properties in a final formulation, such as, rheological properties, hydrophilic or hydrophobic properties, toughness, strength, or flexibility. For example, a low level of crosslinking and free rotation about polymeric bonds will impart flexibility to a compound, and the presence of siloxane moieties will impart hydrophobicity and flexibility. The molecular weight and chain length will affect viscosity, the higher the molecular weight and the longer the chain length, the higher the viscosity.
As used in this specification, aromatic means a compound that meets the classical definition of an aromatic compound, that is, it contains cyclic clouds of delocalized &pgr; electrons above and below the plane of the molecule and the &pgr; clouds have a total of (4n+2) electrons.
The aromatic group may contain an electron withdrawing group such as a nitro group, should less reactivity be desired, but in general, the compounds will have more practical utility in end use applications with greater reactivity.
These hybrid electron donor compounds can be prepared through standard addition or condensation reactions between a functionality on the starting material containing the electron donor group and a co-reactive functionality on the starting material containing the molecular or polymeric group and the vinyl ether functionality, or through coupling reactions using standard Wittig, Heck, or Stille methodologies. For example, useful starting compounds for the electron donor group (other than the vinyl ether) are cinnamyl alcohol or chloride and 3-isopropenyl-&agr;,&agr;-dimethylbenzylisocyanate. Although one skilled in the art can devise suitable variations in reactions by choice and location of functi

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