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Патент USA US3082536

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United States Patent 0 ” "ice
Patented Mar. 26, 1963
case of handling and assurance of flow to ?ll crevices and
establish ?ne detail.
The operable linear diorganosiloxane polymers include
mixtures of polymer types as well as copolymers. Minor
Siegfried Nitzsche and Manfred Wick, Burghausen, Ger
many, assignors to Wacker-Chemie G.m.b.H., Munich,
proportions (i.e. less than .1 mol percent) of monoorgano
siloxane units and/or triorganosilox'ane units as Well as
methylhydrogensiloxane units can be tolerated but avoid
ance of such extraneous units is preferred.
The second ingredient employed herein is an organo
Bavaria, Germany
No Drawing. Filed June 17, 1960, Ser. No. 36,713
iaims priority, application Germany Juiy 10, 1959
5 Qaims. (Ci. 32-45)
This invention relates to a method of employing sili
cone rubber in odontology for ?lling dental caries and
root canals and taking dental impressions, and is a con
triacyloxysilane represented ‘by the formula RSi(OAc)3
where R is as above de?ned and Ac is a saturated aliphatic
monoacyl radical derived from a carboxylic acid such as
propionyl, butyryl, hexoyl, Z-ethylhexoyl, octanoyl, iso
tinuation-in-part of United States application Serial No.
valeryl and stearyl.
816,716, ?led May 29, 1959, which is in turn a continua 15
The linear diorganosiloxane A vand organotriacyloxy
tion-in-part of United States application Serial No.
silane B are mixed by any desired means. It is preferred
602,081, ?led August 3, 1956.
to employ from .1 to 10% by weight of the silane B per
Silicone rubber has been advanced as a satisfactory
100 parts by weight of siloxane A. Longer working time
material for taking dental impressions as well as for ?ll
or shorter cure can be achieved outside this range of
ing root canals (see US. Patent application Serial Nos.
silane to siloxane but the best results are achieved within
602,081, ?led August 3, 1956, and 816,716, ?led May 29,
1959). One di?iculty heretofore encountered in the use
the stated proportions. In addition to the siloxane A and
the silane B minor proportions (i.e., less than 5 parts per
of the silicone rubber masses was that it was necessary
100 parts by weight diorganosiloxane polymer) of dyes,
to combine certain ingredients just prior to use. Thus
?avorings, sedatives, disinfectants, and devitalizing agents
the dentist or technician had to thoroughly mix together 25 can be incorporated in the mixtures employed herein.
carefully measured quantities of materials and thereafter
It may also be desired to employ as cure accelerators .tl
use the mixture within a relatively short period of time
to 2% by weight based on the weight of siloxane A of
before it set up and ‘became too elastomeric for use.
It is an object of this invention to introduce a method
ethanolamine, diethylaminoethanol, o-toluenesulphamide,
oxalic acid, or other organic catalyst.
Furthermore, the mixtures employed in this invention
can contain substantial proportions varying from 5 to
ber system. A further object is to introduce va novel root
200 parts by weight of ?ller per 100 parts by weight of
canal packing which can readily be cleanly removed
siloxane A. These ?llers include reinforcing silicas such
without drilling or other laborious technique. Other ob
as fume silica, silica aerogel, and precipitated silicas. The
jects of the invention and advantages accruing therefrom 35 reinforcing ?llers can be treated and thus display organ
of taking dental impressions as well as of ?lling dental
root canals employing a single component silicone rub
are disclosed in or will be apparent from the disclosure
osilyl groups attached to the ?ller surface. Also operable
and claims following.
are diatomaceous earth, crushed quartz, titania, ferric
This invention comprises utilization for dental mold
oxide, Zinc oxide and the like. However, the ?ller em
ings and root-canal ?lling of a mixture of (A) hydroxyl
ployed should be substantially anhydrous and the ?ller
endblocked linear diorganopolysiloxane and (B) a minor 40 should be preheated to drive off any adsorbed or absorbed
proportion of an organotriacyloxy silane.
water present in the ?ller.
The materials employed include substantially linear
The mixture of siloxane A, silane B, ?ller and other
diorganosiloxane polymers having —OH radicals as ter
additives as employed can be stored in any container sub
minal units at the ends of the chains. Such polymers can
stantially excluding Water or water vapor. The ingredi
be represented by the formula HO(R2SiO)nH where each 45 ents are inert to one another in the absence of moisture
R is a monovalent hydrocarbon radical, a halogenated
monovalent hydrocarbon radical or a cyanoalkyl radical
and n is an integer of at least 5. The substituent radicals
represented by R can be \alkyl radicals such as methyl,
and will not harden or otherwise react While stored in the
absence of moisture. The dentist or technician prepares
the patient for application of ?llings in caries, root-canal
?lling or for taking a dental impression. The mixture of
ethyl, propyl and octadecyl; alkenyl radicals such as 50 siloxane A and silane B is then removed from its container
vinyl, allyl and hexenyl; cycloaliphatic hydrocarbon radi
cals such as cyclohexyl, cyclopentyl, cyclohexenyl and
cyclobutyl; alkaryl radicals such as benzyl and ,B~phenyl—
ethyl; aryl radicals such as phenyl, tolyl, naphthyl and
xenyl; halogenated derivatives of the foregoing radicals
such as chloromethyl, penta?uorobutyl, tri?uorovinyl,
chlorophenyl, bromophenyl, a,a,a-tri?uorotolyl, bromo
xenyl, chlorotri?uorocyclobutyl, chlorocyclohexyl, iodo
phenyl, and 3,3,3-trifluoropropyl, as well as beta-cyano
ethyl, gamma-cyanopropyl, omega-cyanobutyl, beta-cyan
opropyl, gamma-cyanobutyl and omega-cyanooctadecyl.
All of the organic substituents represented by R can be
which may be a tube, a jar or other container, and is ap
plied employing normal techniques. The mixture begins
to cure at once upon coming in contact with atmospheric
55 moisture and particularly with the saliva in the oral cavity.
The curing process is believed to involve hydrolysis of
the organotriacyloxysilane to produce organosilanetriol
[RSi(OH)3] and the carboxylic acid corresponding to the
acyl substituent. The organosilanetriol acts as a cross
60 linking agent and the carboxylic acid acts as the curing
catalyst ingredient required in the aforesaid parent appli
cations Serial Nos. ‘8l-6,7l6 and 602,081.
The following examples are included to illustrate the
the same as in a dimethylsiloxane or they can be different
invention and not to restrict the scope of the invention.
as in phenylmethylsiloxane and ethylcyanoethylsiloxane.
65 All parts and percentages in the examples are based on
It is preferred that at least 715 percent of the substituents
weight unless otherwise speci?ed and all viscosities were
represented by R be lower alkyl radicals of less than 6
measured at 25° C.
carbon atoms.
:The linear diorganosiloxane polymers vary in physical
Example 1
characteristics from thin ?uids of about 35 cs. viscosity
A mixture was prepared by milling together 100 parts
at 25° C. to non-flowing, organic solvent soluble gums. 70 of hydroxyl endblocked dimethylsiloxane polymer of
In general, the liquid polymers are preferred because of
20,000 cs. viscosity, 3.3 parts methyltriacetoxy silane and
of the mixture was employed to ?ll a cleaned and other
the improvement consisting of ('11) employing as the
odontological material a mixture consisting essentially of
(A) 100' parts by weight of an hydroxyl endblocked dior
ganosiloxane of .the formula-HO(R2SiO)nH Where each R
wise prepared vroot-canal, a hard, thoroughly satisfactory
is an organic substituent selected from the group consist
50 parts diatomaceous earth, The mixture was ?lled into
a tube. The mixture remained substantially unchanged
after several weeks of storage. ‘When a suitable quantity
ing of monovalent hydrocarbon radicals, halogenated
?lling was obtained after the mixture had been exposed to
saliva {for less than 30 minutes. The elastomeric ?lling
could be cleanly and completely removed for further work
mereiy by pulling it out of the root-canal with the aid of
monovalent hydrocarbon radicals and cyanoallcyl radi
cals and n is an integer of at least 5 and (B) 0.1 to 10
parts by weight of a silane of the formula RSi(OAc)3
10 where R is as above de?ned and each Ac is a saturated
aliphatic monoacyl radical derived from a carboxylic acid
‘xample 2
and (2) permitting the mixture to come into contact with
Equivalent materials were achieved when the dimethyl
water to secure curing to an elastomeric product.
‘siloxane polymer in Example :1 was replaced with (a) a
*2. The method of claim 1 wherein the mixture further
5,000 cs. hydroxyl endblocked copolyrner of 50 mol per 15 contains (C) 5 to 200 parts by weight of silica ?ller.
cent dimethylsiloxane units and 501 mol percent ethyl
3. The method of claim 2 wherein each R in the dior
phenylsiloxane units; (b) a mixture of 50% hydroxyl
ganosiloxane A and in the silane B is a methyl radical
endblocked diethylsiloxane, 49% 3,3,3-tri?uoropropyl
and (OAc) is an acetoxy radical.
methyl siloxane and 1% vinylmethylsiloxane having a
4. The method of claim 3 wherein the mixture is em
viscosity of 150,000 cs. or (c) a 250,600 cs. copolymer
ployed as a dental root-canal ?lling and contains a total
of 75 mol percent methylethylsiloxane and 25 mol per
of up to 5 parts by weight of additives selected from disin
cent gamrna-cyanopropylmethylsiloxane.
Example 3
fectants, sedatives‘and devitalizing agents.
5. The method of claim 3 wherein the mixture is em
Equivalent materials were achieved when the diatoma 25
oeous earth in Example 1 was replaced with fume silica
ployed to obtain a dental impression.
References Cited in the ?le of this patent
.and the methyltriacetoxysilane was replaced with methyl
trioctanoyloxysilane; 3,3,3-tri?uoropropyltriacetoxysilane;
.dodecyl'triacetoxysilane; phenyltriacetoxysilane; vinyltri
acetoxysilane; or methyltripropionyloxysilane.
That which is claimed is:
1. In a method employing silicone rubber in odontology
30 2,843,555
Schlesinger ___________ __ Apr. 11, 1939
Bel-ridge _____________ __ July 15, 1958
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