GB2108132A - Improvements in dental cements based on metal oxides or hydroxides and eugenol - Google Patents
Improvements in dental cements based on metal oxides or hydroxides and eugenol Download PDFInfo
- Publication number
- GB2108132A GB2108132A GB08125619A GB8125619A GB2108132A GB 2108132 A GB2108132 A GB 2108132A GB 08125619 A GB08125619 A GB 08125619A GB 8125619 A GB8125619 A GB 8125619A GB 2108132 A GB2108132 A GB 2108132A
- Authority
- GB
- United Kingdom
- Prior art keywords
- component
- dental cement
- eugenol
- mixing
- hydroxide
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- RRAFCDWBNXTKKO-UHFFFAOYSA-N eugenol Chemical compound COC1=CC(CC=C)=CC=C1O RRAFCDWBNXTKKO-UHFFFAOYSA-N 0.000 title claims abstract description 32
- 239000003479 dental cement Substances 0.000 title claims abstract description 20
- NPBVQXIMTZKSBA-UHFFFAOYSA-N Chavibetol Natural products COC1=CC=C(CC=C)C=C1O NPBVQXIMTZKSBA-UHFFFAOYSA-N 0.000 title claims abstract description 16
- 239000005770 Eugenol Substances 0.000 title claims abstract description 16
- UVMRYBDEERADNV-UHFFFAOYSA-N Pseudoeugenol Natural products COC1=CC(C(C)=C)=CC=C1O UVMRYBDEERADNV-UHFFFAOYSA-N 0.000 title claims abstract description 16
- 229960002217 eugenol Drugs 0.000 title claims abstract description 16
- 229910000000 metal hydroxide Inorganic materials 0.000 title description 4
- 229910044991 metal oxide Inorganic materials 0.000 title description 4
- 150000004706 metal oxides Chemical class 0.000 title description 4
- 150000004679 hydroxides Chemical class 0.000 title description 3
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 claims abstract description 20
- 239000011787 zinc oxide Substances 0.000 claims abstract description 9
- 239000007788 liquid Substances 0.000 claims abstract description 6
- 235000014113 dietary fatty acids Nutrition 0.000 claims abstract description 5
- 239000000194 fatty acid Substances 0.000 claims abstract description 5
- 229930195729 fatty acid Natural products 0.000 claims abstract description 5
- 150000004665 fatty acids Chemical class 0.000 claims abstract description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims abstract description 5
- 239000002245 particle Substances 0.000 claims abstract description 5
- 235000021355 Stearic acid Nutrition 0.000 claims abstract description 4
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 claims abstract description 4
- 239000000920 calcium hydroxide Substances 0.000 claims abstract description 4
- 229910001861 calcium hydroxide Inorganic materials 0.000 claims abstract description 4
- 239000000347 magnesium hydroxide Substances 0.000 claims abstract description 4
- 229910001862 magnesium hydroxide Inorganic materials 0.000 claims abstract description 4
- 239000000395 magnesium oxide Substances 0.000 claims abstract description 4
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 claims abstract description 4
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 claims abstract description 4
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 claims abstract description 4
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 claims abstract description 4
- 239000008117 stearic acid Substances 0.000 claims abstract description 4
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 claims abstract description 3
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 claims abstract description 3
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 claims abstract description 3
- 239000005642 Oleic acid Substances 0.000 claims abstract description 3
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 claims abstract description 3
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 claims abstract description 3
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims abstract description 3
- 239000004568 cement Substances 0.000 claims abstract 3
- 239000010419 fine particle Substances 0.000 claims abstract 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 14
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 6
- XDZMPRGFOOFSBL-UHFFFAOYSA-N 2-ethoxybenzoic acid Chemical compound CCOC1=CC=CC=C1C(O)=O XDZMPRGFOOFSBL-UHFFFAOYSA-N 0.000 claims description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 4
- 239000004793 Polystyrene Substances 0.000 claims description 3
- 229920002223 polystyrene Polymers 0.000 claims description 3
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 2
- ZOIORXHNWRGPMV-UHFFFAOYSA-N acetic acid;zinc Chemical compound [Zn].CC(O)=O.CC(O)=O ZOIORXHNWRGPMV-UHFFFAOYSA-N 0.000 claims description 2
- 239000011248 coating agent Substances 0.000 claims description 2
- 238000000576 coating method Methods 0.000 claims description 2
- 229920000642 polymer Polymers 0.000 claims description 2
- 239000000377 silicon dioxide Substances 0.000 claims description 2
- 239000011701 zinc Substances 0.000 claims description 2
- 229910052725 zinc Inorganic materials 0.000 claims description 2
- 239000004246 zinc acetate Substances 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- 150000002894 organic compounds Chemical class 0.000 claims 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims 1
- 229910052791 calcium Inorganic materials 0.000 claims 1
- 239000011575 calcium Substances 0.000 claims 1
- 239000013522 chelant Substances 0.000 claims 1
- 239000004615 ingredient Substances 0.000 claims 1
- 229910052749 magnesium Inorganic materials 0.000 claims 1
- 239000011777 magnesium Substances 0.000 claims 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims 1
- 230000003014 reinforcing effect Effects 0.000 claims 1
- 239000012530 fluid Substances 0.000 abstract description 2
- 239000000463 material Substances 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- 229960000583 acetic acid Drugs 0.000 description 4
- 229920001971 elastomer Polymers 0.000 description 2
- 238000010348 incorporation Methods 0.000 description 2
- 239000005060 rubber Substances 0.000 description 2
- -1 Zn++ ions Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000010292 electrical insulation Methods 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000012779 reinforcing material Substances 0.000 description 1
- 239000002631 root canal filling material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- YBTQRZBBLJRNOC-UHFFFAOYSA-N zinc;2-methoxy-4-prop-2-enylphenol;oxygen(2-) Chemical compound [O-2].[Zn+2].COC1=CC(CC=C)=CC=C1O YBTQRZBBLJRNOC-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K6/00—Preparations for dentistry
- A61K6/80—Preparations for artificial teeth, for filling teeth or for capping teeth
- A61K6/849—Preparations for artificial teeth, for filling teeth or for capping teeth comprising inorganic cements
- A61K6/876—Calcium oxide
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K6/00—Preparations for dentistry
- A61K6/80—Preparations for artificial teeth, for filling teeth or for capping teeth
- A61K6/884—Preparations for artificial teeth, for filling teeth or for capping teeth comprising natural or synthetic resins
- A61K6/887—Compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- A61K6/889—Polycarboxylate cements; Glass ionomer cements
Landscapes
- Health & Medical Sciences (AREA)
- Oral & Maxillofacial Surgery (AREA)
- Plastic & Reconstructive Surgery (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Chemical & Material Sciences (AREA)
- Inorganic Chemistry (AREA)
- Dental Preparations (AREA)
Abstract
In a dental cement containing as first component fine particles of zinc oxide or calcium hydroxide or magnesium oxide or hydroxide and as second component a hydroxyl- containing organic liquid such as eugenol that on mixing with the first component sets to form a hard mass, the particles of the first component are coated with a fatty acid such as stearic or oleic acid. Mixing of the cement is facilitated and speeded and higher proportions of first component can be incorporated in cements of a given consistency whereby good strength and low solubility in oral fluids is achieved.
Description
SPECIFICATION
Improvements in dental cements based on metal oxides or hydroxides and eugenol
The present invention relates to improved dental cements based on metal oxides or hydroxides and eugenol and in particular on the zinc oxide eugenol and chemically related systems.
Dental cements are a known class of materials and are used for the cementation of dental appliances and restorations, as lining materials under metallic restorations to provide thermal, chemical and electrical insulation for the pulp, as temporary filling materials and as a root filling material.
On mixing zinc oxide and eugenoi, the paste so formed ultimately sets to a hard mass by the formation of a zinc eugenate:
This essentially slow reaction is accelerated by Zn++ ions, either present as a small. quantity of zinc acetate in the zinc oxide powder or released from the latter by a trace of acetic acid in the Eugenol liquid.
It is well known that this basic system can be improved, notably its mechanical properties, by (a) dissolving a small quantity of polymer such as polystyrene in the eugenol, (b) adding alumina or silica to the zinc oxide powder and (c) replacing eugenol by up to 60% of o-ethoxybenzoic acid, see Brauer et al [J. Dent. Res. 37 547 (1958)]. But these materials are very difficult to mix, especially when a resinous reinforcing material is present.
It is also well known to dental surgeons that maximum strength and minimum solubility in oral fluids is achieved by as high a powder/liquid ratio as possible. But the powder/liquid ratio is limited by the consistency with which the dentist can work, and furthermore the time necessary to incorporate a high quantity of powder will be greater than that required for significant setting to occur.
This invention is based on the realisation that in a dental cement comprising as first component particulate zinc oxide or calcium hydroxide or magnesium oxide or hydroxide and as second component eugenol or a mixture of eugenol with a compatible material such as o-ethoxybenzoic acid it is advantageous that the particles of the first component should be surface treated with a fatty acid such as stearic or oleic acid.
It has long been the practice in, for example, the rubber industry, to surface treat fillers to faciliate their incorporation in rubbers in mixing equipment and to reduce the power consumption of the mixer.
And surface treated zinc oxide is commercially available under the name Extrox 5 from Durham Raw
Materials. But the incorporation of such materials into dental cements has never hitherto been reported, notwithstanding that the Brauer eft at composition was described as long ago as 1 958 and its mixing problems are well known. We have found that providing a fatty acid surface coating not only facilicates and speeds up mixing but allows a higher proportion of metal oxide or hydroxide to be incorporated into a dental cement of a given consistency. Other preferred features of the invention are to be found in the claims, to which attention is hereby directed.
The invention is illustrated by the following examples:
Example 1
A powder comprising 70% stearic acid coated zinc oxide, and 30% aluminium oxide, was mixed with eugenol containing 1% w/v glacial acetic acid. At a powder liquid ratio of 5 g/l ml, a homogeneous paste was easily obtained after mixing for 30 seconds on a glass pad. This paste was initially of a butter-like consistency but set to a hard mass in 10 minutes at 250C.
Example 2
Powders as described in Example 1 but with differing amounts of acetic acid exhibited setting times ranging between 45 minutes and 10 minutes, depending on the acetic acid content of the eugenol.
Example 3
Dental cements as described in Examples 1 and 2 were prepared but without any alumina present. Dental cements of an initial butter-like consistency but which subsequently set to a hard mass were obtained but the set hard mass was weaker than that of Examples 1 and 2.
Example 4
Products even stronger than those described in Examples 1 and 2 but with similar facile mixing properties were obtained by dissolving 5% w/v polystyrene in the eugenol before it was mixed with the zinc oxide.
Example 5
Analogous products to those in Examples 1 4 were obtained when all or part of the eugenol was replaced by o-ethoxybenzoic acid.
Claims (10)
1. In a dental cement comprising as first component fine particles of zinc oxide or calcium hydroxide or magnesium oxide or hydroxide and as second component an organic liquid containing hydroxyl groups that on mixing with the first component reacts therewith to form a hard mass the improvement which comprises coating the particles of the first component prior to mixing with the second component with a fatty acid whereby mixing of said cement is facilitated.
2. A dental cement according to claim 1, wherein the first component comprises particles of zinc oxide surface coated with stearic or oleic acid.
3. A dental cement according to claim 1 or 2, wherein the first component further comprises particles of silica or alumina.
4. A dental cement according to any preceding claim, wherein the organic compound of said second component contains phenolic hydroxyl groups and sets by forming a chelate with the zinc, calcium or magnesium of said first component.
5. A dental cement according to claim 4, wherein the organic compound is eugenol or a mixture thereof with o-ethoxybenzoic acid.
6. A dental cement as claimed in any preceding claim, wherein the second component contains polystyrene or other organic reinforcing polymer dissolved in the eugenol or eugenol-containing mixture.
7. A dental cement as claimed in any preceding claim, wherein the first component further comprises as setting accelerator zinc acetate.
8. A dental cement as claimed in any of claims 1-6 wherein the second component further comprises as setting accelerator acetic acid.
9. A dental cement substantially as hereinbefore described in any one of the Examples.
10. The use of zinc oxide or calcium hydroxide or magnesium oxide or hydroxide coated with a fatty acid as an ingredient of dental cement.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB08125619A GB2108132B (en) | 1981-08-21 | 1981-08-21 | Improvements in dental cements based on metal oxides or hydroxides and eugenol |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB08125619A GB2108132B (en) | 1981-08-21 | 1981-08-21 | Improvements in dental cements based on metal oxides or hydroxides and eugenol |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| GB2108132A true GB2108132A (en) | 1983-05-11 |
| GB2108132B GB2108132B (en) | 1985-05-30 |
Family
ID=10524104
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB08125619A Expired GB2108132B (en) | 1981-08-21 | 1981-08-21 | Improvements in dental cements based on metal oxides or hydroxides and eugenol |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB2108132B (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10101301A1 (en) * | 2001-01-14 | 2002-07-25 | Voco Gmbh | Water based cement |
| US6613812B2 (en) | 2001-01-03 | 2003-09-02 | 3M Innovative Properties Company | Dental material including fatty acid, dimer thereof, or trimer thereof |
| US7091259B2 (en) | 2002-07-03 | 2006-08-15 | 3M Innovative Properties Company | Dental fillers, pastes, and compositions prepared therefrom |
| JP2010105953A (en) * | 2008-10-30 | 2010-05-13 | Bee Brand Medico Dental Co Ltd | Dental composition |
-
1981
- 1981-08-21 GB GB08125619A patent/GB2108132B/en not_active Expired
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6613812B2 (en) | 2001-01-03 | 2003-09-02 | 3M Innovative Properties Company | Dental material including fatty acid, dimer thereof, or trimer thereof |
| DE10101301A1 (en) * | 2001-01-14 | 2002-07-25 | Voco Gmbh | Water based cement |
| EP1222909A3 (en) * | 2001-01-14 | 2004-03-31 | VOCO GmbH | Hydraulic cement |
| DE10101301B4 (en) * | 2001-01-14 | 2007-06-14 | Voco Gmbh | Water based cement |
| US7091259B2 (en) | 2002-07-03 | 2006-08-15 | 3M Innovative Properties Company | Dental fillers, pastes, and compositions prepared therefrom |
| JP2010105953A (en) * | 2008-10-30 | 2010-05-13 | Bee Brand Medico Dental Co Ltd | Dental composition |
Also Published As
| Publication number | Publication date |
|---|---|
| GB2108132B (en) | 1985-05-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 732 | Registration of transactions, instruments or events in the register (sect. 32/1977) | ||
| PCNP | Patent ceased through non-payment of renewal fee |