NATIONAL BUREAU OF STANDARDS REPORT

10 064

Progress Report

on PLASTIC REINFORCED EBA CEMENTS

AS TEMPORARY RESTORATIVE MATERIALS

U.S. DEPARTMENT OF COMMERCE

NATIONAL BUREAU OF STANDARDS
NATIONAL BUREAU OF STANDARDS

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NATIONAL BUREAU OF STANDARDS REPORT

NBS PROJECT

3 1 1.05-1 1-31 10560 June 30, 1969

NBS REPORT

10 064

Progress Report

on PLASTIC REINFORCED EBA CEMENTS

AS TEMPORARY RESTORATIVE MATERIALS

by G. M. Brauer,* E. F. Huget,

+ and D. J. Termini*

* Chemists, Dental Research Section, National Bureau

of Standards, Washington, D. C. 20 234

+ Research Dental Officer, Division of Dental Materials,

U. S. Army Institute of Dental Research.

This investigation is part of the dental research

program conducted by the National Bureau of Standards

and is supported by the Dental Research Division of

the U. S. Army Medical Research and Development

Comm an d.

IMPORTANT NOTICE NATIONAL BUREAU OF S

for use within the Government, and review. For this reason, t whole or in part, is not authi Bureau of Standards, Washing

the Report has been speciticall

Approved for public release by the

Director of the National Institute of

Standards and Technology (NIST)

on October 9, 2015.

ess accounting documents intended

s subjected to additional evaluation

e listing of this Report, either in

ie Office of the Director, National

by the Government agency for which

copies for its own use. <NBS>

U.S. DEPARTMENT OF COMMERCE

NATIONAL BUREAU OF STANDARDS
*

£>

t
Plastic Reinforced EBA Cements as

Temporary Restorative Materials

Previous investigations have resulted in the development of

1-5

improved zinc oxide-eugenol~o-ethcxybenzoic acid (EBA) cements.

These materials have been well accepted for use as luting media for

fixed restorations and as insulating bases. The brittleness

of these cements, however, has limited their use for the temporary

restoration of multiple surface carious lesions in areas subject to

heavy masticatory forces. The purpose of this study was to investigate the possibility of improving the stress-bearing characteristics

of ZOE-EBA cements through the incorporation of powdered polymers of

relatively low elastic moduli.

Materials* and Methods

* Certain commercial materials and equipment are identified in this

report to adequately specify the experimental procedure. In no

instance does such identification imply recommendation or endorsement

by the National Bureau of Standards; neither does it imply that the

materials or equipment identified are necessarily the best available

for the purpose.

- 1-
Zinc oxide, reagent grade (unless otherwise indicated) was passed

through a number 70 sieve. Zinc oxides of varying particle size,

carbon dioxide and water content were prepared from a base oxide that

T $ fulfilled U.S.P. requirements . Tabular alumina had a particle size

ranging from < 1 pm to > 20 ym with few particles > 20 ym. This

aluminum oxide was silanized for use in one experimental formulation.

The material (64 gm) was slurried with acetone. To this slurry

§ 3-methacryloxypropyl tri(methoxy) silane (12 ml) was added.

The solvent was evaporated on a steam bath and the product dried in an oven at

110° C for 8 hours. The aluminum oxide was also surface coated with

varying amounts of polymer by evaporation of acetone solutions

U containing 3.0, 0.5, and 0.05 percent methyl methacrylate copolymer .

A highly dispersed gamma aluminum oxide^ with particle size diameter

+ Baker and Adamson, Allied Chemical Co., New York, N. Y.

T The New Jersey Zinc Co., Palmerton, Pa.

<i> T-61 Tabular Alumina, Aluminum Company of America, Bauxite, Ark.

§ A-174 Silane, Union Carbide Corp., New York, N. Y.

U Acryloid K-120N, Rohm and Haas, Philadelphia, Pa.

II Aluminum Oxide C, Degussa Inc. JCearny, N. J.

- 2-
of 5 to 30 ym and a surface area of 5 to 30 m /g which had been

manufactured by flame hydrolysis of aluminum chloride was employed

in one formulation. Spherical aluminum oxide^ was 1-20 ym particle

^ ^ _j |_ size. Crushed hydrogenated rosin and a terpene resin were

TT

passed through a number 100 sieve* Bentonite coated wood rosin

was technical grade. The sources of the various polymers are given

in Table 1. The aluminum sulfate, EBA and eugenol were reagent

The physical properties of available

grade, ^two commercially/temporary restorative materials (cement A'

and cement b

5§

) were also evaluated.

A

//

**

++

TT

$$

§§

Federal Mogul Division, Ann Arbor, Mich.

Staybelite, Hercules, Inc., Wilmington, Del.

Piccolite Alpha - 115, Pennsylvania Industrial Chemical Corp.,

Clairton, Pa.

Penresina, S. B. Penick and Co., New York, N. Y.

B and T Cement, The L. D. Caulk Co., Milford, Del.

Fynal, The L. D. Caulk Co., Milford, Del.

- 3-
Unless otherwise stated, the powder components were prepared by

thorough mixing of the various components. The composition of the liquid

was 62.5 percent ERA and 37.5 percent eugenol. In preparing the cements,

a powder- liquid ratio was selected which, after thorough mixing for 1-2

minutes, gave a consistency suitable for clinical use. Setting times,

compressive strengths and solubility and disintegration were determined by

the procedures prescribed by American Dental Association Specification

No. 8.® Headspeed of the Universal Testing Machine^ for the compressive

strength measurements was 0.035 in/min. Besides one day storage tests,

some additional data were obtained on storage for one week. Tensile

strengths of specimens, after conditioning similar to that employed for

compressive strength measurements, were measured by the diametral method

using specimens 12 mm in length and 6 mm in diameter. 7 Headspeed of the

Universal Testing Machine

^

was 0.2 in/min. The coefficients of variation

(c.v.) were calculated from the range of values obtained using the formula:

c.v. = range • 100/

d

n

• x)

where dn is approximately equal to /h" for 3 =sntf 10 and x is the average

value. The values for were taken from Natrella. 8

In a limited clinical study, approximately 50 restorations,

including complex restorations subject to heavy occlusal stresses, were

placed using one formulation. Its powder component contained 58.2 percent

ZnO, 27.3 percent Al2 03 , 5.4 percent rosin and 9.1 percent methyl methacrylata

copolymer.^ A powder-liquid ratio of 1.2 gm powder per 0.2 ml of liquid was

used. The material was usually mixed on a glass slab, but could also be

mixed by employing a mechanical mixer. The unreacted eugenol was removed by

blotting or by squeezing the mixed mass in an amalgam squeeze cloth. Patient:

were recalled and observed periodically during the nine-month observation

period.

qq Instron Engineering Corp.

,

Canton, Mass.

- 4

-
Results

The properties of the cements evaluated are given in Tables 2-9.

The estimated coefficient of variation for the tensile strength values

varied widely, but was generally less than 20 percent (maximum value

22.7 percent); compressive strength values gave a maximum coefficient of

variation of 14 percent, but were usually less than 10 percent.

The physical properties of commercial ZOE and zinc phosphate

cements, the Al2 03 reinforced cement reported in our previous study5

and two methyl methacrylate polymer-containing ZOE type cements that

have recently become commercially available are given in Table 2. The

EBA and ZOE reinforced crown and bridge cements exhibited improved

compressive and tensile strengths when compared to conventional ZOE

cements. A marked increase was noted in tensile strength and solubility

on mixing the polymer reinforced powder of commercial cement A with a liquid containing 62.5 percent EBA - 37.5 percent eugenol instead of the

liquid supplied in the commercial formulation.

Variations in rosins, and to some extent also in zinc oxides, affected

the characteristics of the cements (Table 3). An increase in the powder-'

liquid ratio of the mix resulted in a decrease in setting time. Tensile

strength was decreased when a spherical aluminum oxide was used or when the

hydrogenated rosin content was changed from 6 to 8 percent. Using the

powder-liquid ratios indicated, the cements containing

- 5

-
rosin were more soluble and set more slowly than those

to which hydrogenated rosin had been added.

2

A maximum tensile strength of 11.5 MN/m~ (117 kg/sq cm, 1670 psi)

at one week

/was obtained on incorporation of a methyl methacrylate copolymer and

rosin (Table 4). Increasing the polymer content of the powder from 9.1 to

13 percent or decreasing it to 4.8 percent lowered the tensile strength

2

to 9.9 or 8.3 MN/m (101 or 85 kg/sq cm) respectively. Products con- usually

taining hydrogenated rosin/ presented lower tensile strengths and

markedly lower water solubility and disintegration values, but had higher

compressive strengths than those containing rosin.

Improvements in the physical properties of the formulation containing 58.2 percent ZnO, 27.3 percent A1 0 , 5.4 percent hydrogenated

and 9.1 percent methyl methacryrate copolymer,

rosin/were not obtained on increasing! (1) hydrogenated rosin content

the

(2) percentage of eugenol or (3) zinc oxide content (and decreasing

the percentage of A^O^ reinforcing agent). Use of a silanized aluminum

oxide or a dispersed gamma aluminum oxide in the experimental formulamixing characteristics

tions yielded products with inf erio^tsnasreojtoixx. The latter additive

reduced the amount of powder that could be added to the liquid.

Substitution of terpene resin for the rosin ingredient gave a

product with a high 24-hour tensile strength that decreased on longer

exposure to water because of the high water solubility and disintegration

of the product (4.1 percent) in one week. Incorporation of 30 percent

- 6-
Al^O^ powders surface coated with varying amounts of polymer in mixes

with 64 percent ZnO and 6 percent rosin yielded products having

2

tensile strengths ranging from 6.5 to 7.3 MN/m (66 to 74 kg/sq cm)

indicating that the coating had little beneficial effect.

The effects of varying (1) particle size: , (2) the CO^, and (3)

water content of the ZnO on the physical properties of the resulting

cements were slight (Table 5). Zinc oxide containing only trace

amounts of water and CO^ and having the smallest particle size yielded

products of slightly higher tensile strength. Relatively high percentages

of CO^ and water in the ZnO decreased the amount of powder that could

be incorporated into 0.2 ml of liquid.

Table 6 shows the effects of adding 0.5 percent aluminum sulfate

to two of the most promising formulations. A decrease in 1 week water

solubility from 0.94 percent to 0 » 65 percent for rosin-containing

cements was obtained when aluminum sulfate was added. There was,

however, a decrease in tensile strength and an increase in compressive

a luminum

strength on incorporating the aluminum salt. The addition of/sulfate

also decreased slightly the solubility and disintegration of cements

containing hydrogenated rosin.

Table 7 presents the effects of increasing the ethyl methacrylate

content of the methyl methacrylate-ethyl methacrylate copolymers used

in various formulations. Increasing the ethyl methacrylate content

slightly increased the tensile strength. A correlation between resin

- 7 -
composition and compressive strength was not apparent.

Table 8 gives further results of compounding polymers with the

powders. Neither the addition of a low molecular weight experimental

poly(methyl methacrylate) copolymer (55 D-42) nor a commercial acrylic

polymer (KM 228) produced materials with outstanding physical properties.

Addition of 9.0 percent or 5.0 percent calcium acrylate to the formulations

gave mixes with fast setting times (2.5 and 3.5 minutes). Even faster

setting times were obtained with 9.0 percent and 5.0 percent zinc acrylate-

(0.5 to 1.5 minutes) and zinc methacrylate- ( 1 to 2 minutes) containing

formulations. Mixes containing resins other than acrylic polymers also

hardened readily (Table 9) . A vinyl chloride-vinyl acetate copolymercontaining cement had one week tensile and compressive strengths of

9.80 MN/m2 and 91.5 MN/m2 (100 kg/sq cm and 933 kg/sq cm) respectively.

Incorporation of an acrylonitrile-butadiene-styrene terpolymer, a polyacetal

resin or various grades of commercial polycarbonate molding powders produced

materials with physical properties somewhat lower than those containing

acrylic copolymer. A much lower tensile strength was obtained with

polyvinyl stearate. Addition of a dialdehyde starch gave a cement with a relatively high tensile strength and high solubility.

The clinical study, employing the composition given under Materials

and Methods, demonstrated that the cement could be readily adapted to

cavity walls and margins. The material did not dissolve or disintegrate in

the oral fluids. All restorations remained serviceable and showed only

minimal signs of wear over the nine-month observation period. All teeth

restored with this cement remained asymptomatic for the entire period of

observation.

- 8

-
Discussion

The most suitable reinforcing resin for ZOE-EBA cements appear

to be methacryl 3^ or possibly vinyl copolymers. Certain other resilient

resins may also be potentially useful. These materials, however, because

of their resilient nature, cannot be readily obtained in the powdered

form and, therefore, were not included in this study.

Since clinical fracture failures of restorations generally occur

in tension or shear, high tensile strength values are considered more

important than high compressive strengths. The addition of suitable

poly rras greatly increases the tensile strengths of some cements. These

formulations should last longer under clinical conditions than conventional

ZOE products. Clinical studies bear out this point. The formulation

selected had a relatively high tensile strength, but the in vitro

solubility and disintegration values were considerably higher than

those of other promising mixes. Since all restorations remained

serviceable over the nine month observation period, in vivo solubility

did not appear to be of any significance. Unreacted liquid in the

clinical mixes was removed by blotting . It is conceivable that lower in vitro

solubility and disintegration values would have been obtained if this

procedure had been followed in the preparation of laboratory test specimens.

- 9-
It would be desirable to evaluate clinically other promising

formulations found in this study. Limited clinical evaluation indicates that certain polymer-reinforced materials, on the basis of

demonstrated mechanical and palliative properties, appear to be highly

useful as long duration temporary restoratives.

Conclusions

The effects of the addition of polymeric materials to the powder

components of EBA cements were investigated. Acrylic and vinyl copolymers

appeared to be the most suitable additives for achieving reinforcement.

The resultant products exhibited significant increases in tensile strength.

These materials present good manipulative qualities. Limited

clinical studies have suggested that these materials may be highly

desirable for use as long-duration temporary restoratives.

- 10-
References

1. Brauer, G. M. , Simon, L. , and Sangermano, L. : Improved Zinc OxideEugenol Type Cements, J Dent Res 41:1096-1102, 1962.

2. Civjan, S., and Brauer, G. M. : Physical Properties of Cements, Based

on Zinc Oxide, Hydrogenated Rosin, o-Ethoxybenzoic Acid and Eugenol,

J Dent Res 43:281-299, 1965.

3. Civjan, S., and Brauer, G. M. : Clinical Behavior of o-Ethoxybenzoic

Acid-Eugenol-Zinc Oxide Cements, J Dent Res 44 :80-83, 1966.

4. Brauer, G. M. : New Developments in Zinc Oxide-Eugenol Cement,

Ann Dent 26 (No. 2):44-50, 1967.

5. Brauer, G. M. , McLaughlin, R. , and Huget , E. F. : Aluminum Oxide as a

Reinforcing Agent for Zinc Oxide-Eugenol-o-Ethoxybenzoic Acid Cements,

J Dent Res 47 :622-628, 1968.

6. Guide to Dental Materials , ed 4, Chicago : American Dental Association,

1968 pp 140-145.

7. Sweeney, W. T. , and Burns, C. L. : Application of the Diametral

Compression Test to Dental Materials. Abstracts 43rd General Meeting,

International Association for Dental Research, Toronto 1965 p. 122.

8. Natrella, M. G. Experimental Statistics , National Bureau of Standards

Handbook 91, U.S. Government Printing Office, Washington, D.C. p. 2-6.

- 11-
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