Synthetic resins or natural rubbers -- part of the class 520 ser – Synthetic resins – Polymers from only ethylenic monomers or processes of...
Reexamination Certificate
2002-02-19
2003-11-25
Pezzuto, Helen L. (Department: 1713)
Synthetic resins or natural rubbers -- part of the class 520 ser
Synthetic resins
Polymers from only ethylenic monomers or processes of...
C526S317100, C526S322000, C526S324000, C526S325000, C526S329000, C526S329600
Reexamination Certificate
active
06653428
ABSTRACT:
DESCRIPTION OF THE INVENTION
This invention relates to a copolymer obtainable by radical copolymerization of at least two components A and B,
a) at least one ester of an at least dibasic carboxylic acid containing at least one olefinically unsaturated double bond with at least one alkylene oxide adduct being used as component A and
b) at least one other radically polymerizable monomer being used as component B.
The present invention also relates to a process for the production of such copolymers and to their use, more particularly to their use in adhesives.
Properties of polymers are often adapted to meet certain technical requirements by the use of a mixture of monomers in the polymerization process. The polymerization of a mixture of two or more monomers is often referred to as copolymerization and leads, for example, to copolymers containing two different types of monomer or to terpolymers corresponding to the use of three different types of monomer. In polymers such as these, certain technical properties can often be established in dependence upon the comonomer ratio selected and the comonomers selected.
Binders obtainable by radical polymerization of one or more radically polymerizable monomers are frequently used in the production of surface coatings or adhesives. Property variations are generally carried out by the procedure mentioned above, i.e. by copolymerization of suitable monomers.
It is known from the prior art that the flexibility of corresponding films, for example adhesive films, can be improved by the use of comonomers, such as dibutyl maleate, vinyl versatate or acrylates. Unfortunately, a disadvantage of using such comonomers is that the adhesion of such films or bonds to polar surfaces often deteriorates significantly due to the hydrophobia of the comonomers. In addition, there is an upper limit to the chain length in the alcohol residues of the comonomers used to the extent that comonomers with long-chain residues are not accessible to use in emulsion polymerization because their solubility in water is too poor.
Emulsion polymerizations, for example the emulsion polymerization of vinyl acetate, often require the addition of a protective colloid. Such a process step on the one hand increases the duration of the process and, on the other hand, adds to the cost of the production.
Accordingly, the problem addressed by the present invention was to provide a copolymer which could be produced without expensive process steps and which, when used in adhesives, would lead to flexible adhesive films showing excellent adhesion even to hydrophilic substrate surfaces. Another problem addressed by the present invention was to provide a process for the production of that copolymer.
The problems stated above are solved by a copolymer obtainable by the radical copolymerization of at least two components A and B, component A being a carboxylic acid ester of an unsaturated carboxylic acid with an alkylene oxide adduct and component B being another radically polymerizable monomer.
Accordingly, the present invention relates to a copolymer obtainable by radical copolymerization of at least two components A and B,
a) at least one ester of an at least dibasic carboxylic acid containing at least one olefinically unsaturated double bond with an alkylene oxide adduct being used as component A and
b) at least one other radically polymerizable monomer being used as component B.
A “copolymer” in the context of the present specification is understood to be a polymer obtainable by radical polymerization of two or more radically polymerizable monomers. It may be a statistical copolymer, i.e. the sequence of monomers is not subject to any particular order, or even an alternating or block copolymer.
According to the invention, a component A and a component B are copolymerized to produce the copolymers according to the invention. At least one ester of an at least dibasic carboxylic acid containing at least one olefinically unsaturated double bond with an alkylene oxide adduct is used as component A.
The at least dibasic carboxylic acid containing at least one olefinically unsaturated double bond may be selected, for example, from maleic acid, fumaric acid, itaconic acid, aconitic acid, 3,4,5,6-tetrahydrophthalic acid, crotonic acid or a mixture of two or more thereof.
Esters suitable for use as component A in accordance with the invention may be produced, for example, by only partly esterifying the olefinically unsaturated di- or polycarboxylic acids on which the esters are based, i.e. only some of the carboxylic acid groups available for esterification are esterified with a suitable alkylene oxide adduct. In addition, the carboxylic acid groups of the carboxylic acid may also be partly or completely reacted with an alkylene oxide so that the ester function is formed by alkoxylation.
Partial esters suitable for use as component A in one preferred embodiment of the present invention are, for example, partial esters of the above-mentioned carboxylic acids with alkylene oxide adducts of linear or branched saturated alcohols containing at least 8 carbon atoms. Suitable alcohols are, for example, the fatty alcohols containing at least 8 carbon atoms obtainable, for example, by reduction of natural fats or oils or by reduction of fatty acids or fatty acids cuts obtainable from natural fats or oils or derivatives thereof, for example esters with alcohols containing 1 to 4 carbon atoms.
Fatty alcohols particularly suitable for the production of the alkylene oxide adducts are, for example, octyl alcohol, nonyl alcohol, decyl alcohol, undecyl alcohol, dodecyl alcohol, tridecyl alcohol, tetradecyl alcohol, pentadecyl alcohol, hexadecyl alcohol, octadecyl alcohol, nonadecyl alcohol, Guerbet alcohols, unsaturated fatty alcohols, such as 12-hydroxystearyl alcohol, or higher homologs of such alcohols containing up to about 44 carbon atoms. The alkyl residue of the fatty alcohols may be linear or branched, saturated or unsaturated.
Other suitable alcohol components for the production of the partial esters are, for example, alkylene oxide adducts of correspondingly alkoxylatable compounds which have an OH group at the end of the alkoxy unit formed by the alkoxylation. Alkoxylatable compounds suitable for the production of the alkylene oxide adducts are, for example, dialkylamines with linear or branched, saturated or unsaturated alkyl chains containing a total of at least about 8 carbon atoms, linear or branched, saturated or unsaturated carboxylic acids, for example fatty acids, containing at least about 8 carbon atoms, linear or branched, saturated or unsaturated acid amides, for example fatty acid monoethanolamides, containing at least about 8 carbon atoms and linear or branched, saturated or unsaturated alkylamines; for example fatty amines, with at least 8 carbon atoms in the alkyl chain.
“Alkoxylates” or “alkylene oxide adducts” in the context of the present specification are understood to be the reaction products of suitable nucleophiles, for example correspondingly functionalized ethers, amines, carboxylic acids, carboxylic. acid amides or alcohols, with alkylene oxides, containing 2 to about 44 carbon atoms, more particularly about 8 to about 24 carbon atoms.
In one preferred embodiment of the invention, alkylene oxides containing 2 to 4 and more particularly 2 or 3 carbon atoms, for example ethylene oxide or propylene oxide, are used for the production of the alkylene oxide adducts. Only one alkylene oxide need be used for the production of the alkoxylation products, although two or more alkylene oxides may also be used. Where it is carried out with more than two alkylene oxides, the alkoxylation can lead either to a statistical or an alternating copolyalkylene oxide or to a block copolyalkylene oxide.
In one preferred embodiment of the invention, the alkoxylation by which the alkylene oxide adduct is formed is carried out with ethylene oxide.
The alkylene oxide adducts suitable for use as alcohol component in accordance with the present invention contain on average at least one alkylene oxide uni
Boege Kai
Friedrich Klaus
Klein Johann
Moeller Thomas
Harper Stephen D.
Henkel Kommanditgesellschaft auf Aktien (Henkel KGaA)
Murphy Glenn E. J.
Pezzuto Helen L.
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