Curable compositions containing benzoxazine

Details Curable compositions containing benzoxazine Curable compositions containing benzoxazine

2002-02-23

2003-09-16

Truong, Duc (Department: 1711)

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

Synthetic resins

Nitrogen-containing reactant

C528S422000, C525S203000, C525S205000, C525S206000, C525S330900

Reexamination Certificate

active

06620905

ABSTRACT:

FIELD OF THE INVENTION
This invention relates to curable compositions containing compounds or resins having a benzoxazine moiety.
BACKGROUND OF THE INVENTION
Curable compositions are used in the fabrication and assembly of semiconductor packages and microelectronic devices, such as in the bonding of integrated circuit chips to lead frames or other substrates, in the bonding of circuit packages or assemblies to printed wire boards, or in encapsulants, underfills, or coating materials. There are a number of curable compositions that are used in the industry, but not all these give as full a performance as is needed for all uses.
Monobenzoxazine and polybenzoxazine compounds and resins (hereinafter benzoxazines) add to the spectrum of performance materials for use within the semiconductor fabrication industry. These compounds are formed by the reaction of a mono-phenol, a mono- or poly-amine (primary) and formaldehyde or of a mono-amine (primary), a polyphenol, and formaldehyde. They exhibit good heat resistance, electronic properties, low water absorption, no out-gassing, low dielectric constant, and almost no shrinkage on cure. However, on their own, they have limited processability because of their high viscosity, and they tend to be brittle and require more flexibility for use in electronic devises.
SUMMARY OF THE INVENTION
This invention is a curable composition containing at least one monobenzoxazine or polybenzoxazine moiety (benzoxazine) and at least one other curable resin or compound. For purposes of this specification, a benzoxazine compound is one that contains at least one of the structure:
in which R
1
and R
2
are any organic moiety, including another benzoxazine structure. The composition optionally may comprise a curing agent and/or a filler. The composition can be in the form of a paste, prepared by blending or milling, or a film, prepared by standard film making techniques known to those skilled in the art. These compositions have utility as adhesives, coatings and encapsulants, especially for use within the semiconductor fabrication industry. They have particular utility as die attach adhesives and films, and underfill materials, such as no-flow underfills, capillary flow underfills, wafer level underfills, and as lead free solders.
DETAILED DESCRIPTION OF THE INVENTION
The benzoxazine compound will contain at least one of the structure disclosed above, and, in general, any benzoxazine or polybenzoxazine containing compound can be used in the curable composition. Benzoxazine compounds are described, for example, in U.S. Pat. No. 5,543,516 and WO 99/18092. Suitable benzoxazine compounds include those of the formula
in which R
1
is a divalent radical that may be aliphatic, aromatic, or a combination of aliphatic and aromatic, and that may contain heteroatoms, such as oxygen, nitrogen, sulfur, phosphorous, or halogen, or that may be a single bond, or that may be S, S
2
, SO, SO
2
, O, or CO; and R
2
is hydrogen, an alkyl or substituted alkyl, an aromatic or substituted aromatic. Suitable and preferred benzoxazine compounds are:
In addition to compounds such as the above, the benzoxazine may also be present in a polymeric species, such as the following:
in which R
1
is as described above, n is an integer that will vary depending on the polymeric composition from which the benzoxazine depends, and each Q is a polymeric entity, for example, polyurethane, polyether, polyester, poly(butadiene) or polystyrenic.
The benzoxazine compound will be present in the curable composition in an amount within the range of 1% or more to 99% or less by weight of the combination of one or more benzoxazines and one or more other curable compounds or resins.
Preferred curable resins for blending with the benzoxazines include vinyl ethers, vinyl silanes, compounds or resins containing vinyl or allyl functionality, thiol-enes (a thiol-ene within this specification and claims is a compound or resin that is the reaction product of a thiol and a compound having carbon to carbon unsaturation), compounds or resins containing cinnamyl or styrenic functionality, fumarates, maleates, acrylates, maleimides, and cyanate esters.
Other curable resins for blending with the benzoxazines include hybrid resins that contain both epoxy and cinnamyl or styrenic functionality, hybrid resins that contain both vinyl silane and cinnamyl, styrenic, acrylate or maleimide functionality, hybrid resins that contain both vinyl silane and epoxy or vinyl ether functionality, and hybrid resins that contain both epoxy and acrylate or maleimide functionality.
Within the structures in this specification and claims, C
36
represents a mixture of isomers derived from linoleic and oleic acids having linear and branched alkyl chains with 36 carbon atoms.
Suitable curable compounds or resins having vinyl ether or allyl functionality for blending with benzoxazines include:
These compounds can be prepared by synthetic routes and from starting materials known to those skilled in the art. Other compounds containing vinyl ether or allyl functionality are commercially available from BASF, ISP, and Aldrich.
Suitable curable compounds or resins for blending with benzoxazines and containing both styrenic or cinnamyl and vinyl ether functionality are disclosed in U.S. Pat. No. 6,307,001 and include:
These compounds can be prepared by synthetic routes and from starting materials known to those skilled in the art, or by the routes disclosed in the identified patent.
Suitable curable compounds for blending with benzoxazine and containing styrenic or cinnamyl functionality include:
These compounds can be prepared by synthetic routes and from starting materials known to those skilled in the art.
Suitable curable compounds for blending with benzoxazine and containing alkoxy silane and styrenic, cinnamyl, vinyl ether or maleimide functionality include:
Suitable curable compounds or resins for blending with benzoxazine and containing styrenic or cinnamyl functionality with acrylate, maleate, fumarate or maleimide functionality, are disclosed in U.S. Pat. No. 6,300,456, and include:
These compounds can be prepared by synthetic routes and from starting materials known to those skilled in the art, or by the routes disclosed in U.S. Pat. No. 6,300,456.
Additional curable maleimides for blending with benzoxazine are those disclosed in U.S. Pat. Nos. 6,057,381, 6,063,828, 6,180,187, 6,187,886, 6,281,314, and 6,265,530, and include:
which resin is derived from a poly(butadiene) and in which m and n will vary depending on the particular poly(butadiene) starting material, (in one embodiment m and n will be integers to provide a number average molecular weight of 3600),
These compounds can be prepared by synthetic routes and from starting materials known to those skilled in the art, or by the routes disclosed in U.S. Pat. Nos. 6,057,381, 6,063,828, 6,180,187, 6,187,886, 6,281,314, and 6,265,530.
Additional curable maleates and fumarates for blending with benzoxazine are dioctyl maleate, dibutyl maleate, dioctyl fumarate, dibutyl fumarate. Additional maleate and fumarates are available from Aldrich.
Additional curable resins containing both epoxy and electron acceptor or electron donor functionality may be blended with benzoxazine. Electron donor functionality includes groups in which a carbon to carbon double bond is attached to an aromatic ring and conjugated with the unsaturation in the ring, such as styrenic or cinnamyl groups. Other electron donor groups include vinyl silanes and vinyl ethers. Electron acceptor functionality includes maleates, fumarates, acrylates and maleimides. Examples of compounds of this type include the following:
These compounds can be prepared by synthetic routes and from starting materials known to those skilled in the art.
Suitable curable compounds or resins containing both vinyl silane and electron donor or electron acceptor functionality for blending with benzoxazines include:
These compounds can be prepared by synthetic routes and from starting materials known to those skilled in the art.
Suitable cura

Affiliated with

Also associated with

Rating

Curable compositions containing benzoxazine does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Curable compositions containing benzoxazine, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Curable compositions containing benzoxazine will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-3062535