Dental materials based on polysiloxanes

Details Dental materials based on polysiloxanes Dental materials based on polysiloxanes

2000-01-20

2003-05-27

Toomer, Cephia D. (Department: 1714)

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

Synthetic resins

Processes of preparing a desired or intentional composition...

C523S116000, C523S118000, C528S026000, C524S588000

Reexamination Certificate

active

06569917

ABSTRACT:

The invention relates to dental materials based on methacrylate-modified polysiloxanes capable of polymerization.
Dental materials based on silanes capable of polymerization are known. DE 36 10 804 A1 discloses dental resin compositions which contain siloxane polymers, monomers which are co-polymerizable with the siloxane polymer, and a polymerization catalyst. The dental resin compositions are said to have an improved compressive strength, abrasion resistance and flexural strength after polymerization.
DE 34 07 087 A1 and WO 92/16183 relate to the use of compounds based on organically modified silicic acid polycondensates for coating teeth and tooth-replacement parts. The cured coats are said to be resistant to the build-up of plaque.
Dental resin compositions based on polymerizable polysiloxanes are known from DE 41 33 494, which are manufactured by hydrolytic condensation of one or several silanes of which at least one is substituted by a 1,4,6-trioxaspiro-[4,4]-nonane radical or a (meth)acrylate group, the latter preferably containing a thioether function. The dental resin compositions are said to show only a small change in volume during curing, however silanes with orthoester groups are difficult of access and less storage-stable whereas thioether groups are sensitive to oxidation.
DE 196 19 046 discloses low-shrinkage polymerizable compounds based on mercapto- or norboronnene silanes and a reaction partner for the en-thiolpolymerization. The curing of these compositions is accompanied by low polymerization shrinkage and results in products with high mechanical strength which however also contain thioether groups sensitive to oxidation.
The object of the invention is the provision of dental materials based on polysiloxanes which can be covalently incorporated in organic-inorganic composite materials and do not contain spiro- or thioether groups.
The object is achieved by dental materials which contain at least one polysiloxane based on one or several silanes according to the formula (I)
[(W
q
—R
6
—Z)
p
—R
3
]
m
Y—R
2
—SiX
n
R
1
3−n
  Formula (I)
in which
X
stands for a halogen atom, a hydroxyl, alkoxy and/or
acyloxy group;
n
is equal to 1 to 3;
R
1
stands for an alkyl, alkenyl, aryl, alkylaryl,
arylalkyl group;
R
2
stands for an alkylene group;
R
3
stands for a p-times substituted, straight, branched or
cyclic, saturated or unsaturated, aromatic or aliphatic
organic radical with 2 to 40 carbon atoms and optionally
1 to 6 heteroatoms;
R
6
stands for a q-times substituted, straight, branched or
cyclic organic radical with 1 to 20 carbon atoms or is
absent;
p
is equal to 1 to 6;
q
is equal to 1 to 6;
y
stands for —NR
4
—, N or —(C═O)—NH—;
m
is equal to 2 for Y = N and equal to 1 for Y = —NR
4
— or
—(C═O)—NH—;
R
4
stands for an alkyl or aryl group;
Z
stands for O, S, —(C═O)—O—, —(C═O)—NH—,
—O—(C═O)—NH— or is absent;
W
stands for CH
2
═CR
5
—(C═O)—O—; and
R
5
stands for a hydrogen atom or an alkyl group.
Suitable heteroatoms are phosphorus and preferably oxygen.
In the whole description as well as the claims, alkyl, acyloxy, alkoxy, alkenyl groups and alkylene groups are understood to mean radicals which preferably contain 1 to 25 carbon atoms, particularly preferably 1 to 10 carbon atoms and quite particularly preferably 1 to 4 carbon atoms, and optionally carry one or several subsituents such as for example halogen atoms, nitro groups or alkyloxy radicals. Aryl means radicals, groups or substituents which preferably have 6 to 10 carbon atoms and can be substituted as stated above. The above definitions are also valid for compound groups such as for example alkyl aryl and aryl alkyl groups. An alkyl aryl group thus describes for example an aryl group defined as above which is substituted by an alkyl group as defined above.
The alkyl, acyloxy, alkoxy, alkenyl groups and alkylene groups can be straight-chained, branched or cyclic.
Preferred definitions, which can be chosen independently from each other, for the individual variables, are:
X
=
a methoxy and/or ethoxy group;
n
=
2 or 3;
R
1
=
a C
1
to C
3
alkyl group, in particular a methyl
group;
R
2
=
a C
1
to C
4
alkylene group;
R
3
=
a p-times substituted, straight, branched or
cyclic, saturated or unsaturated, aromatic or
aliphatic organic radical with 2 to 10 carbon atoms
and optionally a heteroatom, preferably an oxygen
atom, particularly preferably a C
1
to C
4
alkenylene
radical or a monocyclic radical with 4 to 10, in
particular 5 to 8 carbon atoms;
R
6
=
a q-times substituted, straight, branched or
cyclic organic radical with 1 to 4 carbon atoms,
particularly preferably a C
1
to C
3
alkylene radical;
p
=
1 or 2, in particular 1;
q
=
1 or 2;
Y
=
N or —(C═O)—NH—;
Z
=
—(C═O)—O—; and/or
R
5
=
a hydrogen atom or a methyl group.
Concrete examples of particularly preferred silanes according to formula (I) are:
The silanes of formula (I) are accessible via addition and condensation reactions known per se, the number of hydrolyzable groups, groups capable of polymerization, and further functional groups being able to be varied by the appropriate selection of educts.
Silanes in which Y has the meaning —NR
4
— or N are for example accessible by addition of an aminosilane compound to an m-times unsaturated group R
3
:
Thus e.g., bis[2-(2-methacryloyloxyethoxycarbonyl)-ethyl]-(3-triethoxysilylpropyl)amine is obtained by reacting 3-amino-propyltriethoxysilane with 2-acryloyloxyethylmethacrylate:
Silanes in which Y is equal to —(C═O)—NH— are accessible for example by reacting an isocyanatosilane with a carboxylic acid which contains p radicals W capable of polymerization:
The reaction of 3-isocyanatopropyltriethoxysilane with 2-methacryloyloxyethyl-hydrogen-succinate results in e.g. 2-methacryloxyethyl-3-[(3-triethoxysilyl)propylaminocarbonyl]propionate:
Suitable carboxylic acid methacrylates can be obtained by reacting di- or tetracarboxylic acid mono or dianhydrides with suitable OH-functionalized compounds capable of polymerization such as for example 2-hydroxyethylmethacrylate or glycerine dimethacrylate.
To synthesize silanes in which Y is equal to —(C═O)—NH—, the synthesis methods known in peptide chemistry, such as e.g. the DCC method or the mixed anhydrides method, can moreover also be used to react carboxylic acids with amino-group containing compounds, for example the reaction of an aminosilane with a carboxylic acid which contains p radicals W capable of polymerization:
Thus, the reaction of 3-aminopropyltriethoxysilane with 2-methacryloyloxyethyl-hydrogen-succinate also results in 2-methacryloxyethyl-3-[(3-triethoxysilyl)propylaminocarbonyl]propionate:
The silanes (I) are stable compounds and can be processed to give the polysiloxanes, either alone or together with other hydrolytically condensable compounds of silicon, aluminium, zirconium, titanium, boron, tin, vanadium and/or phosphorus. These additional compounds can be used either as such or already in pre-condensed form.
Preferred further hydrolytically condensable compounds of silicon are silanes of the general formula (II)
R
7
k
(Z′R
8
)
m
SiX′
4-(k+m)
  Formula (II)
in which
R
7
stands for a C
1
to C
8
alkyl, C
2
to C
12
alkenyl- or
C
6
to C
14
aryl group;
R
8
stands for a C
1
to C
8
alkylene, C
2
to
C
12
alkenylene or C
6
to C
14
arylene group;
X′
stands for a hydrogen or halogen atom or a C
1
to
C
8
alkoxy group;
Z′
stands for a glycidyl, acryl, methacryl, vinyl,
allyl or vinyl ether group;
k
is equal to 0, 1, 2 or 3;
m
is equal to 0, 1, 2 or 3; and
k + m
is equal to 0, 1, 2 or 3.
Preferred definitions, which can be chosen independently from each other, for the individual variables, are:
R
7
=
a C
1
to C
3
alkyl, C
2
to C
5
alkenyl or a phenyl
group;
R
8
=
a C
1
to C
5
alkylene, C
2
to C
5
alkenylene or a
phenylene group;
X′
=
a halogen atom, a m

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