CN113367995B - Dental glass ion cement composite - Google Patents
Dental glass ion cement composite Download PDFInfo
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- CN113367995B CN113367995B CN202110502546.7A CN202110502546A CN113367995B CN 113367995 B CN113367995 B CN 113367995B CN 202110502546 A CN202110502546 A CN 202110502546A CN 113367995 B CN113367995 B CN 113367995B
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- 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
- A61K6/831—Preparations for artificial teeth, for filling teeth or for capping teeth comprising non-metallic elements or compounds thereof, e.g. carbon
- A61K6/836—Glass
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K6/00—Preparations for dentistry
- A61K6/15—Compositions characterised by their physical properties
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- 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
- A61K6/891—Compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/04—Acids; Metal salts or ammonium salts thereof
- C08F220/06—Acrylic acid; Methacrylic acid; Metal salts or ammonium salts thereof
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- Health & Medical Sciences (AREA)
- Oral & Maxillofacial Surgery (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
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- Plastic & Reconstructive Surgery (AREA)
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Dental Preparations (AREA)
- Curing Cements, Concrete, And Artificial Stone (AREA)
Abstract
The invention discloses a dental glass ionomer cement compound. The matrix components of the invention comprise silicon-aluminum-fluorine glass powder and polycarboxylic acid liquid, wherein the polymeric monomer of the polycarboxylic acid comprises: 55-70 parts of acrylic acid, 25-30 parts of itaconic acid and 5-15 parts of alkyl olefine acid. The invention prepares a ternary carboxylic acid copolymer, which is dissolved in water to prepare a polycarboxylic acid liquid for glass ionomer cement, and the polycarboxylic acid liquid is mixed and solidified with silicon-aluminum fluoride glass powder sold in the market, so that the prepared glass ionomer cement has the characteristic of high mechanical strength. Compared with the prior art, the invention can effectively improve the bending strength and the compressive strength of the glass ionomer cement, and expands the application range of the glass ionomer cement in the field of dental restoration.
Description
Technical Field
The invention belongs to the technical field of dental materials, and particularly relates to a dental glass ionomer cement compound.
Background
The invention relates to glass ionomer cement which is used in the 70 s of the 20 th century, and is widely applied to functional repair of defective teeth due to the characteristics of color similar to that of natural teeth, small irritation to dental pulp, good edge sealing property, long-term fluorine release and the like. However, glass ionomer cement has poor wear resistance and low mechanical strength as compared with other restorative materials, and is mainly used clinically for dental restoration of sites not bearing occlusal force or for temporary dental restoration.
At present, two methods are mainly used for improving the mechanical strength of the glass ionomer cement. Firstly, a reinforcing body, such as silver alloy powder or glass fiber, is added into the silicon-aluminum-fluorine glass powder. Although these reinforcements are effective in improving the mechanical properties of the glass ionomer cement, the addition of silver alloy destroys the color of the glass ionomer cement, and the addition of glass fiber deteriorates the clinical handling properties. Secondly, the structure of the polycarboxylic acid in the liquid is changed, a third monomer containing a large-volume non-reactive functional group is introduced in the synthetic process of the polycarboxylic acid, and the large-volume functional group can damage the regularity of a polycarboxylic acid skeleton and increase the degree of acid-base reaction, so that the mechanical property of the glass ionomer cement is improved. Researchers have synthesized various polycarboxylic acid copolymers using N-vinyl pyrrolidone (NVP), diethanolamine-modified Glycidyl Methacrylate (GMADEA), and a series of N-acryl-type amino acid derivatives as a third monomer. However, these polycarboxylic acid copolymers cannot improve both the bending property and the compression property of the glass ionomer cement. Therefore, the method has important significance in developing the glass ionomer cement with good mechanical property and long-term use performance by selecting a proper monomer as a spacer and modifying a polycarboxylic acid structure.
Disclosure of Invention
Aiming at the problem that the traditional glass ionomer cement is insufficient in mechanical strength, the invention selects an olefine acid monomer containing a long alkyl chain as a third monomer, and the long alkyl chain is utilized to destroy the regularity of a polycarboxylic acid skeleton, so that the degree of acid-base reaction is improved; and the carboxyl at the tail end of the long alkyl chain can further react with the silicon-aluminum fluoride glass powder, so that the defects of poor durability and the like caused by non-reactive functional groups are avoided. A dental glass ionomer cement composite having good bending strength and compressive strength and a method for preparing the same are provided.
The technical scheme adopted for solving the technical problem is as follows:
the glass ionomer cement composite is prepared by fully stirring and mixing silicon-aluminum-fluorine glass powder and polycarboxylic acid liquid by a stirring knife, the liquid is prepared by mixing water and polycarboxylic acid, and the source of the silicon-aluminum-fluorine glass powder is not limited and is available on the market.
Further, the mass ratio of the polycarboxylic acid liquid to the alumino-fluoride glass powder is 1.
Further, the polycarboxylic acid liquid is prepared from polycarboxylic acid and deionized water according to a mass ratio of 60-35.
Further, the structural formula of the polycarboxylic acid is shown as follows:
n = 1-9 in the structural formula; wherein the amount of x, y, z is determined by the addition amount of acrylic acid monomer, itaconic acid monomer and alkyl olefine acid monomer.
Further, the three monomers for synthesizing the polycarboxylic acid are respectively as follows in parts by mass: 55-70 parts by mass of acrylic acid monomer, 25-30 parts by mass of itaconic acid monomer and 5-15 parts by mass of alkyl olefine acid monomer.
Further, the preparation method of the polycarboxylic acid comprises the following steps:
dissolving an acrylic acid monomer, an itaconic acid monomer and an alkyl olefine acid monomer in deionized water to prepare a monomer aqueous solution; preparing an initiator aqueous solution, preheating one half of the initiator aqueous solution in a reactor at 60-90 ℃ for half an hour, respectively filling the rest initiator aqueous solution and a monomer aqueous solution in different constant-pressure dropping funnels, and dropping the initiator aqueous solution and the monomer aqueous solution into the reactor at a constant speed for 1-5 hours; after the dropwise addition, the reaction solution reacts for 12 to 24 hours at a constant temperature of 60 to 90 ℃. Then purifying the product.
Further, in the preparation process of the polycarboxylic acid, the alkyl olefine acid monomers include, but are not limited to: butenoic acid, pentenoic acid, hexenoic acid, heptenoic acid, octenoic acid, nonenoic acid, decenoic acid, undecenoic acid, and dodecenoic acid.
Further, in the preparation process of the polycarboxylic acid, the initiator includes but is not limited to: potassium persulfate, ammonium persulfate, azobisisobutylamidine hydrochloride, azobisisopropylimidazoline hydrochloride, azobisisobutylimidazoline hydrochloride, azobisN-hydroxyisobutylamidine hydrate, azobismethyl-N-2-hydroxybutylacrylamide, azobiscyanovaleric acid, and dimethyl azobisisobutyrate.
Furthermore, in the preparation process of the polycarboxylic acid, the dosage of the initiator is 1-8% of the total mass of the monomers, and the mass ratio of water to the monomers is 3.
Compared with the prior art, the invention has the following advantages and effects:
the method has simple process, the prepared glass ionomer cement liquid has proper viscosity, excellent operation performance when being mixed with the silicon-aluminum-fluorine glass powder, moderate curing time, good matching degree of the prepared sample color and luster with teeth, and obviously improved bending performance and compression performance at the same time.
Detailed Description
Comparative example:
preparation of commercially available glass ionomer cement
A commercially available silicon-aluminum-fluorine glass powder and a commercially available polycarboxylic acid liquid are taken according to the powder-liquid mass ratio of 3.6: 1, fully mixed by a stirring knife, quickly filled into a 2mm multiplied by 25mm mould, and the bending strength of the sample strip obtained after solidification is soaked in water for 24 hours.
The compression strength of the cylinder obtained by curing is measured after soaking the cylinder in water for 24 hours, wherein the powder is prepared by fully mixing commercially available silicon-aluminum-fluorine glass powder and commercially available polycarboxylic acid liquid according to the powder-liquid mass ratio of 3.6: 1 through a stirring knife, quickly filling the mixture into a mold with the diameter of 4mm multiplied by 6 mm.
Example 1
The synthesis of the ternary carboxylic acid copolymer of acrylic acid, itaconic acid and 4-pentenoic acid and the preparation of the glass ionomer cement.
Dissolving 19.95g of acrylic acid monomer, 8.55g of itaconic acid monomer and 1.5g of 4-pentenoic acid monomer in 140g of deionized water; 1.80g of potassium persulfate is dissolved in 40g of deionized water to prepare an initiator aqueous solution, and half of the initiator aqueous solution is put into a four-neck flask and preheated for half an hour at 80 ℃. The rest initiator aqueous solution and the rest monomer aqueous solution are respectively contained in different constant-pressure dropping funnels and are dropped into the flask at a constant speed for 2 hours; after the dropwise addition, the reaction system was reacted at 80 ℃ for 16 hours, and then the product was purified. The synthesized polycarboxylic acid solid is dissolved in deionized water with equal mass to prepare 50wt% of polycarboxylic acid liquid A.
The bending strength of the sample strip obtained by curing was measured after soaking in water for 24 hours, after sufficiently mixing commercially available silicon-aluminum-fluorine glass powder and the above-mentioned polycarboxylic acid liquid A at a powder-liquid mass ratio of 3.6: 1 by a stir knife, and rapidly filling the mixture into a mold of 2 mm. Times.2 mm. Times.25 mm.
Taking commercially available silicon-aluminum-fluorine glass powder and the polycarboxylic acid liquid A according to the powder-liquid mass ratio of 3.6: 1, fully mixing by using a stirring knife, quickly filling into a mold with the diameter of 4mm multiplied by 6mm, and soaking the cured cylinder in water for 24 hours, and then measuring the compressive strength.
Example 2
Synthesis of acrylic acid, itaconic acid and 4-pentenoic acid tricarboxylic acid copolymer and preparation of glass ionomer cement
Dissolving 18.90g of acrylic acid monomer, 8.10g of itaconic acid monomer and 3.0g of 4-pentenoic acid monomer in 140g of deionized water; 1.80g of potassium persulfate is dissolved in 40g of deionized water to prepare an initiator aqueous solution, and half of the initiator aqueous solution is put into a four-neck flask and preheated for half an hour at 80 ℃. The rest initiator aqueous solution and the rest monomer aqueous solution are respectively contained in different constant-pressure dropping funnels and are dropped into the flask at a constant speed for 2 hours; after the dropwise addition, the reaction system was reacted at 80 ℃ for 16 hours, and then the product was purified. And dissolving the synthesized polycarboxylic acid solid in deionized water with the same mass to prepare 50wt% of polycarboxylic acid liquid B.
The commercially available silicon-aluminum-fluorine glass powder and the polycarboxylic acid liquid B are taken according to the powder-liquid mass ratio of 3.6: 1, fully mixed by a stirring knife, quickly filled into a die with the size of 2mm multiplied by 25mm, and the bending strength of the sample strip obtained after solidification is measured after soaking in water for 24 hours.
Taking commercially available silicon-aluminum-fluorine glass powder and the polycarboxylic acid liquid B according to the powder-liquid mass ratio of 3.6: 1, fully mixing by using a stirring knife, quickly filling into a mold with the diameter of 4mm multiplied by 6mm, and soaking the cured cylinder in water for 24 hours, and then measuring the compressive strength.
Example 3
Dissolving 17.85g of acrylic acid monomer, 7.65g of itaconic acid monomer and 4.5g of 4-pentenoic acid monomer in 140g of deionized water; 1.80g of potassium persulfate is dissolved in 40g of deionized water to prepare an initiator aqueous solution, and half of the initiator aqueous solution is put into a four-neck flask and preheated for half an hour at 80 ℃. The rest initiator aqueous solution and the rest monomer aqueous solution are respectively contained in different constant-pressure dropping funnels and are dropped into the flask at a constant speed for 2 hours; after the dropwise addition, the reaction system was reacted at 80 ℃ for 16 hours, and then the product was purified. And dissolving the synthesized polycarboxylic acid solid in deionized water with the same mass to prepare 50wt% of polycarboxylic acid liquid C.
Commercially available silicon-aluminum-fluorine glass powder and the polycarboxylic acid liquid C are taken according to the powder-liquid mass ratio of 3.6: 1, fully mixed by a stirring knife, quickly filled into a die with the size of 2mm multiplied by 25mm, and the bending strength of the sample strip obtained after solidification is measured after soaking in water for 24 hours.
Taking commercially available silicon-aluminum-fluorine glass powder and the polycarboxylic acid liquid C according to the powder-liquid mass ratio of 3.6: 1, fully mixing by using a stirring knife, quickly filling into a mold with the diameter of 4mm multiplied by 6mm, and soaking the cured cylinder in water for 24 hours, and then measuring the compressive strength.
The mechanical properties of examples 1 to 3 and the comparative example were as follows:
| glass ion water heater | Flexural Strength/MPa | Compressive strength/MPa |
| Comparative example | 29.8 | 120 |
| Example 1 | 36.7 | 143 |
| Example 2 | 31.4 | 136 |
| Example 3 | 32.0 | 127 |
As can be seen from the table, the glass ion cement prepared in examples 1 to 3 has better bending strength than the commercially available glass ion cement.
Example 4
The synthesis of the ternary carboxylic acid copolymer of acrylic acid, itaconic acid and 4-pentenoic acid and the preparation of the glass ionomer cement.
Dissolving 19.95g of acrylic acid monomer, 8.55g of itaconic acid monomer and 1.5g of 4-pentenoic acid monomer in 50g of deionized water; 0.6g of potassium persulfate is dissolved in 40g of deionized water to prepare an initiator aqueous solution, and half of the initiator aqueous solution is put into a four-neck flask and preheated for half an hour at 60 ℃. The rest initiator aqueous solution and the rest monomer aqueous solution are respectively contained in different constant-pressure dropping funnels and are dropped into the flask at a constant speed for 2 hours; after the dropwise addition, the reaction system reacts at 60 ℃ for 16 hours, and then the product is purified. The synthesized polycarboxylic acid solid is dissolved in deionized water with equal mass to prepare 50wt% of polycarboxylic acid liquid D.
The commercially available silicon-aluminum-fluorine glass powder and the polycarboxylic acid liquid agent D are taken according to the powder-liquid mass ratio of 3.6: 1, fully mixed by a stirring knife, quickly filled into a die with the size of 2mm multiplied by 25mm, and the bending strength of a sample strip obtained by curing is measured after soaking in water for 24 hours.
Example 5
Dissolving 19.95g of acrylic acid monomer, 8.55g of itaconic acid monomer and 1.5g of 4-pentenoic acid monomer in 80g of deionized water; 1.20g of potassium persulfate is dissolved in 40g of deionized water to prepare an initiator aqueous solution, and half of the initiator aqueous solution is put into a four-neck flask and preheated for half an hour at 70 ℃. The rest initiator aqueous solution and the rest monomer aqueous solution are respectively contained in different constant-pressure dropping funnels and are dripped into the flask at a constant speed for 2 hours; after the dropwise addition, the reaction system was reacted at 70 ℃ for 16 hours, and then the product was purified. The synthesized polycarboxylic acid solid is dissolved in deionized water with equal mass to prepare 50wt% of polycarboxylic acid liquid E.
The commercially available silicon-aluminum-fluorine glass powder and the polycarboxylic acid liquid E are taken according to the powder-liquid mass ratio of 3.6: 1, fully mixed by a stirring knife, quickly filled into a die with the size of 2mm multiplied by 25mm, and the bending strength of the sample strip obtained after solidification is measured after soaking in water for 24 hours.
Example 6
Dissolving 19.95g of acrylic acid monomer, 8.55g of itaconic acid monomer and 1.5g of 4-pentenoic acid monomer in 110g of deionized water; 1.80g of potassium persulfate is dissolved in 40g of deionized water to prepare an initiator aqueous solution, and half of the initiator aqueous solution is put into a four-neck flask and preheated for half an hour at 80 ℃. The rest initiator aqueous solution and the rest monomer aqueous solution are respectively contained in different constant-pressure dropping funnels and are dropped into the flask at a constant speed for 2 hours; after the dropwise addition, the reaction system was reacted at 80 ℃ for 16 hours, and then the product was purified. The synthesized polycarboxylic acid solid is dissolved in deionized water with equal mass to prepare 50wt% of polycarboxylic acid liquid agent F.
The commercially available silicon-aluminum-fluorine glass powder and the polycarboxylic acid liquid agent F are taken according to the powder-liquid mass ratio of 3.6: 1, fully mixed by a stirring knife, quickly filled into a die with the size of 2mm multiplied by 25mm, and the bending strength of a sample strip obtained by curing is measured after soaking in water for 24 hours.
Example 7
Dissolving 19.95g of acrylic acid monomer, 8.55g of itaconic acid monomer and 1.5g of 4-pentenoic acid monomer in 120g of deionized water; 2.40g of potassium persulfate is dissolved in 40g of deionized water to prepare an initiator aqueous solution, and half of the initiator aqueous solution is put into a four-neck flask and preheated for half an hour at 90 ℃. The rest initiator aqueous solution and the rest monomer aqueous solution are respectively contained in different constant-pressure dropping funnels and are dropped into the flask at a constant speed for 2 hours; after the dropwise addition, the reaction system reacts at 90 ℃ for 16 hours, and then the product is purified. The synthesized polycarboxylic acid solid is dissolved in deionized water with equal mass to prepare 50wt% of polycarboxylic acid liquid G.
Commercially available silicon-aluminum-fluorine glass powder and the polycarboxylic acid liquid G are taken according to the powder-liquid mass ratio of 3.6: 1, fully mixed by a stirring knife, quickly filled into a die with the size of 2mm multiplied by 25mm, and the bending strength of the sample strip obtained after solidification is measured after soaking in water for 24 hours.
The bending properties of examples 4 to 7 and the comparative example were as follows:
| glass ion water heater | Flexural Strength/MPa | Flexural modulus/GPa |
| Comparative example | 29.8 | 121.3 |
| Example 4 | 38.3 | 110.3 |
| Example 5 | 35.9 | 110.4 |
| Example 6 | 34.1 | 100.7 |
| Example 7 | 30.5 | 115.5 |
As is clear from the table, examples 4 to 7 showed an improvement in flexural strength and a decrease in flexural modulus as compared with the comparative examples, and it was found that the synthesized polycarboxylic acid can improve the flexibility of the glass ionomer cement. The conditions of synthesis of the polycarboxylic acid affect the final bending properties of the glass ionomer cement at the same monomer ratio.
It should be understood that the above detailed description of the embodiments of the present invention with reference to the preferred embodiments is illustrative and not restrictive, and it should not be considered that the detailed description of the embodiments of the present invention is limited thereto, and it should be understood that those skilled in the art to which the present invention pertains that modifications may be made to the embodiments described in the embodiments or that equivalents may be substituted for some of the features thereof without departing from the spirit of the present invention and the scope of the patent protection is defined by the claims to be filed with the present invention.
The above examples of the present invention are merely examples for clearly illustrating the present invention and are not intended to limit the embodiments of the present invention. Other variations and modifications will be apparent to persons skilled in the art in light of the above description. And are neither required nor exhaustive of all embodiments. Any modification, equivalent replacement, and improvement made within the spirit and principle of the present invention should be included in the protection scope of the claims of the present invention.
Claims (1)
1. The dental glass ionomer cement composite is characterized by comprising silicon-aluminum-fluorine glass powder and a polycarboxylic acid liquid;
the mass ratio of the polycarboxylic acid liquid to the alumino-fluoride glass powder is 1 to 3 to 1;
in the polycarboxylic acid liquid agent, the mass ratio of polycarboxylic acid to water is 60 to 35;
the structural formula of the polycarboxylic acid in the polycarboxylic acid liquid agent is shown as follows:
n =2 in the structural formula;
the polycarboxylic acid comprises the following three monomers in parts by mass: 55 to 70 parts by mass of an acrylic monomer, 25 to 30 parts by mass of an itaconic acid monomer and 5 to 15 parts by mass of an alkyl olefine acid monomer;
the preparation method of the polycarboxylic acid is characterized by comprising the following steps:
dissolving an acrylic acid monomer, an itaconic acid monomer and an alkyl olefine acid monomer in deionized water to prepare a monomer aqueous solution; preparing an initiator aqueous solution, preheating half of the initiator aqueous solution in a reactor at 60 to 90 ℃ for half an hour, respectively filling the rest of the initiator aqueous solution and a monomer aqueous solution in different constant-pressure dropping funnels, and dropping the initiator aqueous solution and the monomer aqueous solution into the reactor at a constant speed for 1 to 5 hours; after the dropwise addition is finished, reacting the reaction solution at the constant temperature of 60-90 ℃, and then purifying the product;
the alkyl olefine acid monomer comprises: pentenoic acid;
the initiator comprises: more than one of potassium persulfate, ammonium persulfate, azobisisobutylamidine hydrochloride, azobisisopropylimidazoline hydrochloride, azobisisobutylimidazoline hydrochloride, azobisN-hydroxyisobutylamidine hydrate, azobismethyl-N-2-hydroxybutylacrylamide, azobiscyanovaleric acid and dimethyl azobisisobutyrate;
the using amount of the initiator is 1-8% of the total mass of the monomers, and the mass ratio of water to the monomers is (3) - (1);
the reaction time is 12-24 hours.
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1997036943A1 (en) * | 1996-03-28 | 1997-10-09 | Nulite Systems International Pty. Ltd. | Elastomeric state glass ionomer cement |
| CN1451368A (en) * | 2003-05-19 | 2003-10-29 | 武汉大学 | Atraumatic vitreous ion cement liquid formulation and preparing process thereof |
| CN102174141A (en) * | 2011-03-21 | 2011-09-07 | 北京化工大学 | Method for preparing glass ionomer cement liquid with low dissolubility and acidity |
| JP2013028568A (en) * | 2011-07-29 | 2013-02-07 | Gc Corp | Glass ionomer cement for dentistry |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2329807A1 (en) * | 2009-12-07 | 2011-06-08 | Dentsply DeTrey GmbH | Dental composition |
| KR101647954B1 (en) * | 2014-11-27 | 2016-08-12 | (주)스피덴트 | Dental composite for glass ionomer cement and method for thereof |
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Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1997036943A1 (en) * | 1996-03-28 | 1997-10-09 | Nulite Systems International Pty. Ltd. | Elastomeric state glass ionomer cement |
| CN1451368A (en) * | 2003-05-19 | 2003-10-29 | 武汉大学 | Atraumatic vitreous ion cement liquid formulation and preparing process thereof |
| CN102174141A (en) * | 2011-03-21 | 2011-09-07 | 北京化工大学 | Method for preparing glass ionomer cement liquid with low dissolubility and acidity |
| JP2013028568A (en) * | 2011-07-29 | 2013-02-07 | Gc Corp | Glass ionomer cement for dentistry |
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