Synthetic resins or natural rubbers -- part of the class 520 ser – Synthetic resins – Mixing of two or more solid polymers; mixing of solid...
Reexamination Certificate
2002-08-19
2004-04-20
Sellers, Robert (Department: 1712)
Synthetic resins or natural rubbers -- part of the class 520 ser
Synthetic resins
Mixing of two or more solid polymers; mixing of solid...
C523S446000, C523S466000, C523S468000
Reexamination Certificate
active
06723802
ABSTRACT:
BACKGROUND OF THE INVENTION
(1) Field of the Invention
The present invention relates to cured epoxy resin and polyglycoside-based cured polymers and to a process and compositions for the preparation of these polymers. In particular, the present invention relates to the curing of epoxy resin precursors with a polyglycoside based polymer. The polymers can contain fillers of various known types, preferably those which are natural. The polyglycoside moiety provides a degree of biogradability to the resulting polymer not usually available in epoxy resin based polymers. The polymers are stable to elevated temperatures up to 300° C., and thus are useful in vehicle engine compartments for sound deadening and the like.
(2) Description of Related Art
Recently, there has been increasing interest in the use of biocomposites of natural fibers, particularly cellulosic fibers, especially in the automobile industry. These composites are reported to offer advantages of ~20% reduction in processing temperature and ~25% reduction in cycle time in addition to a weight reduction of about ~30% over conventional glass fiber composites (Saheb, D. N., et al., Advances in Polymer Technology 18 4 351 (1999)). For automotive applications biocomposites have to meet several demanding requirements such as temperature resistance and wet environmental resistance (Reussmann, T., et al., Advanced Engineering Materials 1, 2, 140 (1999)). The incorporation of biobased polymer with natural fibers would be the best combination for development of environmentally friendly composites if the developed biocomposites meet the demanding requirements.
Glucose maleic acid ester vinyl copolymer (GMAEVC) has been developed to use as a biodegradable adhesive for the paper and packaging industry. GMAEVC contains reactive carboxylic and hydroxyl functional groups in its structure. This leads to cost effective and better performing of biocomposites.
U.S. Pat. Nos. 5,869,173 and 6,171,688 to Zheng to al show composites which can be formed.
OBJECTS
It is therefore an object of the present invention to provide novel epoxy resin and polyglycoside based polymers. Further, it is an object of the present invention to provide such polymers which have a degree of biodegradability and high temperature resistance. These and other objects will become increasingly apparent by reference to the following description and the Figures.
SUMMARY OF THE INVENTION
The present invention relates to a curable polymer composition which comprises:
(a) an epoxy resin precursor; and
(b) a co-polymer of a polyglycoside acid or acid ester reacted with an organic anhydride or acid, and optionally with a vinyl monomer, wherein the ratio of (a) to (b) produces a cured polymer composition.
In particular the present invention relates to a curable polymer composition which comprises:
(a) an epoxy resin precursor; and
(b) a copolymer of a polyglycoside acid or acid ester of the formula II or III as follows:
and mixtures thereof and optionally a vinyl monomer, wherein R and R″ are alkyl containing 1 to 30 carbon atoms and wherein the ratio of (a) to (b) produces a cured polymer composition. X and y are integers between 0 and 4 but x and y are not O at the same time.
The present invention particularly relates to a curable polymer composition which comprises:
(a) liquid epoxy resin; and
(b) a copolymer of the formula as follows:
wherein Glu is a saccharide moiety which is derived from a sugar selected from the group consisting of &agr;-D-glucose, fructose, mannose, galactose, talose, gulose, allose, altrose, idose, arabinose, xylose, lyxosc, ribose, and mixtures thereof, or by hydrolysis of a material selected from the group consisting of starch, corn syrups, maltodextrins, maltose, sucrose, lactose, maltotriose, xylobiose, mellibiose, cellobiose, raffinose, stachiose, levoglucosan, 1,6-anhydroglucofuranose, and mixtures thereof, and wherein the ratio of (a) to (b) produces a cured polymer composition, wherein R
1
and R
2
are substituent groups of a vinyl monomer or mixture of vinyl monomers, wherein said vinyl monomer or mixture of vinyl monomers is selected from the group consisting of vinyl acetate, ethyl hexyl acrylate, butyl acrylate, ethyl acrylate, hydroxyethyl acrylate, hydroxyethyl methacrylate, lauryl acrylate, methyl methacrylate, methacryclic acid, acrylic acid, other acrylates, mixtures of different acrylate monomers, ethylene, 1,3-butadiene, styrene, vinyl chloride, vinylpyrrolidinone, other vinyl monomers, and mixtures thereof, R is selected from the group consisting of a C1 to C30 alkyl and mixtures thereof, R″ is selected from the group consisting of a C1 to C30 alkyl and mixtures thereof, or a hydrogen, n is an integer ranging from 0 to 10; x and y are integers ranging from 0 to 4, but not x and y are 0 at the same time, p and q are integers ranging from 0 to 1000, but not both p and q are zero, and wherein ~~~ indicates continuing polymer chains.
Preferably Glu is an &agr;-D-glucose moiety. Preferably the molar ratio of (a) to (b) is about 1:1. Preferably an alkyl polyglycoside is reacted with malic anhydride to form the polymer which is reacted with the vinyl monomer to form the copolymer. Preferably R
1
and R
2
and R″ are selected from the group consisting of hydrogen and n-butyl.
The composition includes a filler. A fiber, particularly a cellulosic fiber, is preferred. Clay can be used as a filler. The compositions are cured to solid resins with or without the fillers.
The present invention also relates to a process for forming a cured polymer composition which comprises:
(a) providing a mixture of (1) a liquid mixture of an epoxy resin precursor and (2) a polyglucoside-organic anhydride reaction product which has optionally been polymerized with a vinyl monomer, wherein the ratio of (1) to (2) provides the cured polymer composition; and
(b) heating the mixture to produce the cured polymer.
In particular the present invention relates to a process for forming a cured polymer composition which comprises:
(a) providing (1) a liquid epoxy resin precursor and (2) a liquid copolymer of a polyglycoside acid or acid ester of the formula II or II as follows:
and mixtures thereof which has optionally been reacted with a vinyl monomer wherein R and R
11
are alkyl contain 1 to 30 carbon atoms, x and y are integers between 0 and 4 but not x and y are o at the same time and wherein the ratio of (1) to (2) produces the cured polymer composition; and
(b) heating the mixture to produce the cured polymer composition.
Further, the present invention relates to a process for the preparation of a cured polymer composition which comprises:
(a) providing a mixture of
(1) a liquid epoxy resin; and
(2) a liquid copolymer of the formula I as follows:
wherein Glu is a saccharide moiety which is derived from a sugar from the group consisting of &agr;-D-glucose, fructose, mannose, galactose, talose, gulose, allose, altrose, idose, arabinose, xylose, lyxosc, ribose, and mixtures thereof, or by hydrolysis of a material selected from the group consisting of starch, corn syrups, maltodextrins, maltose, sucrose, lactose, maltotriose, xylobiose, mellibiose, cellobiose, raffinose, stachiose, levoglucosan, 1,6-anhydroglucofuranose, and mixtures thereof, wherein R
1
and R
2
are substituent groups of a vinyl monomer or mixture of vinyl monomers, wherein said vinyl monomer or mixture of vinyl monomers is selected from the group consisting of vinyl acetate, ethyl hexyl acrylate, butyl acrylate, ethyl acrylate, hydroxyethyl acrylate, hydroxyethyl methacrylate, lauryl acrylate, methyl methacrylate, methacryclic acid, acrylic acid, other acrylates, mixtures of different acrylate monomers, ethylene, 1,3-butadiene, styrene, vinyl chloride, vinylpyrrolidinone other vinyl monomers, and mixtures thereof, R is selected from the group consisting of a C1 to C30 alkyl and mixtures thereof, R″ is selected from the group consisting of a C1 to C30 alkyl and mixtures thereof, or a hydrogen, n is an integer ranging from 0 to 10; x and y are integers ranging from 0 to 4,
Drzal Lawrence T.
Han Seong Ok
Board of Trustees of Michigan State University
McLeod Ian C.
Sellers Robert
LandOfFree
Epoxy resin and polyglycoside based polymers and process for... does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Epoxy resin and polyglycoside based polymers and process for..., we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Epoxy resin and polyglycoside based polymers and process for... will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-3270269