Process for the preparation of antimicrobial plastics

Details Process for the preparation of antimicrobial plastics Process for the preparation of antimicrobial plastics

1999-09-14

2001-03-20

Dudash, Diana (Department: 1762)

Coating processes

With post-treatment of coating or coating material

Heating or drying

C106S015050, C106S018320, C424S405000, C424S583000, C523S122000

Reexamination Certificate

active

06203856

ABSTRACT:

BACKGROUND OF THE INVENTION
Field of the Invention
The present invention relates to antimicrobial polymers prepared by copolymerization of tert-butylaminoethyl methacrylate with one or more aliphatically unsaturated monomers, a process for their preparation and their use. More particularly, the invention relates to antimicrobial polymers prepared by graft copolymerization of tert-butylaminoethyl methacrylate with one or more aliphatically unsaturated monomers on a substrate, a process for their preparation and their use.
Colonization and spread of bacteria on surfaces of pipelines, containers or packaging are highly undesirable. Layers of slime often form, which allow the microbe populations to rise to extreme levels, lastingly impairing the quality of water, drinks and foodstuffs, and can even lead to decay of the goods and damage to the health of consumers.
Bacteria are to be kept away from all areas of life where hygiene is of importance. Since textiles directly contact the body, and in particular the genital area, and are used for the care of the sick and elderly, textiles should be freed of bacteria. Bacteria should also be kept away from the surfaces of furniture and equipment in nursing wards, in particular in the intensive care and infant care sector, in hospitals, especially in rooms for medical operations, and in isolation wards for critical cases of infection, as well as in toilets.
Equipment and surfaces of furniture and textiles are currently treated to ward against bacteria as required or also preventively with chemicals or solutions and mixtures thereof which act as disinfectants, such having a more or less broad and massive antimicrobial action. Such chemical compositions have a non-specific action, are often themselves toxic or irritating, or form degradation products which are unacceptable to health. Intolerances are often also found in appropriately sensitized persons.
Another procedure which is used to inhibit the spread of bacteria on surfaces is to incorporate antimicrobially active substances into a matrix.
Tert-butylaminoethyl methacrylate is a commercially available monomer of methacrylate chemistry and is employed in particular as a hydrophilic monomer in copolymerizations. Thus, EP 0 290 676 describes the use of various polyacrylates and polymethacrylates as a matrix for immobilization of bactericidal quaternary ammonium compounds.
U.S. Pat. No. 3,592,805 discloses the preparation of systemic fungicides in which perhalogenated acetone derivatives are reacted with methacrylate esters, such as, for example, tert-butylaminoethyl methacrylate.
U.S. Pat. No. 4,515,910 describes the use of polymers of hydrogen fluoride salts of aminomethacrylates in dental medicine. The hydrogen fluoride bonded in the polymers emerges slowly from the polymer matrix and is said to have actions against caries.
In another technical field, U.S. Pat. No. 4,532,269 discloses a terpolymer of butyl methacrylate, tributyltin methacrylate and tert-butylaminoethyl methacrylate. This polymer is used as an antimicrobial paint for ships, the hydrophilic tert-butylaminoethyl methacrylate promoting slow erosion of the polymer and in this way liberating the highly toxic tributyltin methacrylate as an antimicrobially active compound.
In these applications, the copolymer prepared with aminomethacrylates is only a matrix or carrier substance for the added microbicidal active compounds, which (an diffuse or migrate out of the carrier. Polymers of this type lose their action at a greater or lesser speed when the necessary “minimum inhibitory concentration” (MIC) is no Longer achieved on the surface.
EP 0 204 312 describes a process for the preparation of antimicrobially treated acrylonitrile fibers. The antimicrobial action is based on a protonated amine as a comonomer unit, dimethylaminoethyl methacrylate and tertbutylaminoethyl methacrylate, inter alia, being used as protonated species. However, the antimicrobial action of pronated surfaces is severely reduced after loss of the H
⊕
ions. A need, therefore, continues to exist for an improved method of providing surfaces with anti-bacterial properties.
SUMMARY OF THE INVENTION
Accordingly, one object of the present invention is to provide materials which have antimicrobial properties, which contain no active compounds which can be washed out, and in which the antimicrobial action is pH-independent.
Briefly, this object and other objects of the present invention as hereinafter will become more readily apparent can be attained by a method of imparting antimicrobial activity to the surface(s) of an apparatus or article, by
copolymerizing tertbutylaminoethyl methacrylate with at least one other aliphatically unsaturated monomer in the presence of said apparatus or article by which adhesion of the copolymer to said surface(s) is achieved.
An aspect of the invention is a process for the preparation of antimicrobial polymers, which comprises subjecting tert-butylaminoethyl methacrylate to grafting copolymerization with one or more aliphatically unsaturated monomers on a substrate.
DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS
It has now been found, surprisingly, that polymers which have a surface which is permanently microbicidal, is not attacked by solvents and physical stresses and shows no migration are obtained by copolymerization of tertbutylaminoethyl methacrylate with one or more other aliphatically unsaturated monomers or by grafting copolymerization of tert-butylaminoethyl methacrylate with one or more aliphatically unsaturated monomers on a substrate. It is not necessary to provide the polymer with biocidally active compounds.
The copolymerization of tert-butylaminoethyl methacrylate and one or more other aliphatically unsaturated monomers can be carried out by graft copolymerization on a substrate and is possible with the microbicidal action being largely retained. All aliphatically unsaturated monomers are suitable for this, such as, for example, acrylates and methacrylates of the formula:
wherein R
1
is hydrogen or methyl, R
2
is hydrogen, a metal atom or a branched or unbranched aliphatic, cycloaliphatic, heterocyclic or aromatic hydrocarbon group having up to 20 carbon atoms or a branched or unbranched aliphatic, cycloaliphatic, heterocyclic or aromatic hydrocarbon chain having up to 20 carbon atoms, which is derivatized by carboxyl groups, carboxylate groups, sulfonate groups, alkylamino groups, alkoxy groups, halogens, hydroxyl groups, amino groups, dialkyl amino groups, phosphate groups, phosphonate groups, sulfate groups, carboxamido groups, sulfonamido groups, phosphonamido groups or combinations of these groupings. R
3
can be hydrogen or identical to R
2
.
It is furthermore possible to employ vinyl compounds of the formula:
and maleic and fumaric acid derivatives of the formula
R
4
O
2
C—HC═CH—CO
2
R
4
in which R
4
can be hydrogen, an aromatic radical or a methyl group or can be identical to R
2
.
R
5
can be hydrogen, a methyl group or a hydroxyl group, and can be identical to R
2
, or can be an ether Of the composition OR
2
.
Suitable substrate materials include all polymeric plastics, such as, for example, polyurethanes, polyamides, polyesters, polyethers, polyether-block amides, polystyrene, polyvinyl chloride, polycarbonates, polyorganosiloxanes, polyolefins, polysulfones, polyisoprene, polychloroprene, polytetrafluoroethylene (PTFE), corresponding copolymers and blends, as well as natural and synthetic rubbers, with or without radiation-sensitive groups. The process of the invention can also be applied to surfaces of metal, glass or wooden bodies which are painted or are otherwise coated with plastic.
The substrates' surfaces can be activated by a number of methods before the grafting copolymerization. They are expediently freed from oils, greases or other impurities beforehand in a known manner by means of a solvent.
The standard polymers can be activated by UV radiation. A suitable source of radiation is, for example, a UV-Excimer apparatus HERAEUS Noblelight, Hanau, Germany. However, mercury va

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