WO2014058514A1 - Composition adaptée pour utilisation en tant qu'adhésif - Google Patents

Composition adaptée pour utilisation en tant qu'adhésif Download PDF

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Publication number
WO2014058514A1
WO2014058514A1 PCT/US2013/052033 US2013052033W WO2014058514A1 WO 2014058514 A1 WO2014058514 A1 WO 2014058514A1 US 2013052033 W US2013052033 W US 2013052033W WO 2014058514 A1 WO2014058514 A1 WO 2014058514A1
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WO
WIPO (PCT)
Prior art keywords
composition
polysiloxane resin
mmole
mole
less
Prior art date
Application number
PCT/US2013/052033
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English (en)
Inventor
Olha V. HOY
Original Assignee
Milliken & Company
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Milliken & Company filed Critical Milliken & Company
Publication of WO2014058514A1 publication Critical patent/WO2014058514A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J183/00—Adhesives based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Adhesives based on derivatives of such polymers
    • C09J183/04—Polysiloxanes
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/04—Polysiloxanes
    • C08G77/045—Polysiloxanes containing less than 25 silicon atoms
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/04—Polysiloxanes
    • C08G77/12—Polysiloxanes containing silicon bound to hydrogen
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/04—Polysiloxanes
    • C08G77/20—Polysiloxanes containing silicon bound to unsaturated aliphatic groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/70—Siloxanes defined by use of the MDTQ nomenclature
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2666/00—Composition of polymers characterized by a further compound in the blend, being organic macromolecular compounds, natural resins, waxes or and bituminous materials, non-macromolecular organic substances, inorganic substances or characterized by their function in the composition
    • C08L2666/66—Substances characterised by their function in the composition
    • C08L2666/68—Plasticizers; Solvents

Definitions

  • compositions suitable for use as adhesives in dental applications relate to compositions suitable for use as adhesives in dental applications.
  • this disclosure relates to compositions that are believed to be well suited for use in temporarily bonding silicone dental impression materials to dental equipment, such as metal and/or plastic trays used to hold the impression material.
  • the invention generally provides a composition suitable for use as an adhesive, such as an adhesive for dental applications.
  • the composition generally comprises a blend of two polysiloxane resins in a solvent.
  • the first polysiloxane resin comprises at least one repeating unit in which a hydrogen is directly bonded to a silicon atom.
  • the second polysiloxane resin comprises at least one repeating unit in which an alkyl group or alkenyl group (e.g., vinyl group) is directly bonded to a silicon atom.
  • the invention provides a composition comprising:
  • Ri and R 2 are independently selected from the group consisting of hydrogen, alkyl groups, and aryl groups;
  • R 3 and R 4 are independently selected from the group consisting of alkyl groups and aryl groups, and R 5 is selected from the group consisting alkyl groups and alkenyl groups;
  • the invention generally provides a composition comprising a first polysiloxane resin, a second polysiloxane resin, and a solvent.
  • the invention provides a composition consisting essentially of the first polysiloxane resin, the second polysiloxane resin, and the solvent.
  • the term "consisting essentially of” means that the composition does not contain appreciable amounts of additional polysiloxane resins (i.e., polysiloxane resins in addition to the first and second polysiloxane resins enumerated above and described below).
  • any such additional polysiloxane resins are present in such a composition (i.e., a composition consisting essentially of the components enumerated above), the additional polysiloxane resin(s) are present in an amount of about 5% or less, about 4% or less, about 3% or less, about 2% or less, or about 1 % or less by weight of the composition.
  • the first and second polysiloxane resins can be generally described as "MQ resins.” This terminology denotes the particular siloxane repeating units contained in the resin.
  • the Q refers to a repeating unit having a structure
  • the "Oi/ 2 " bonded to the silicon atom is intended to denote an oxygen atom that is "shared” by adjacent repeating units in the resin.
  • the O-i /2 from adjacent repeating units “combine” to form a Si— O— Si linkage.
  • the M refers to a repeating unit conforming to the structure of Formula (A) (A)
  • R', R", and R"' each represent groups such as alkyl groups, aryl groups, or hydrogen.
  • the M units contain only one bond to an adjacent siloxane repeating unit (i.e., they contain only one ⁇ 1 / 2 ). Therefore, an M unit terminates the propagation of the siloxane chain.
  • the first polysiloxane resin is an MQ resin comprising at least one repeating unit in which a hydrogen is directly bonded to a silicon atom. More specifically, in such an embodiment, the first polysiloxane resin comprises at least one repeating unit conforming to the structure of Formula (I)
  • Ri and R 2 are independently selected from the group consisting of hydrogen, alkyl groups (e.g., C 1 -C 2 0 alkyl groups), and aryl groups (e.g., C 6 -C 2 o aryl groups).
  • Ri and R 2 are independently selected from the group consisting of C-i-C-io alkyl groups, more preferably C C 4 alkyl groups, with methyl groups being particularly preferred.
  • the first polysiloxane resin can comprise additional repeating units in addition to those specifically noted above.
  • the first polysiloxane resin can also comprise one or more additional M units (i.e., one or more M units having a different structure than the structure of Formula (II)).
  • the first polysiloxane resin can further comprise one or more repeating units conforming to the structure of Formula (A)
  • the first polysiloxane resin can also comprise D units and/or T units.
  • the D units have the structure
  • R' and R" are each independently selected from the groups identified above in connection with the discussion of the structure of Formula (A).
  • the first polysiloxane resin consists essentially of repeating units conforming to the structure of Formula (I) and Formula (II).
  • the term "consists essentially of” means that the resin does not contain appreciable amounts of repeating units conforming to a different structure. More preferably, the first polysiloxane resin consists of repeating units conforming to the structure of Formula (I) and Formula (II).
  • the first polysiloxane resin can have any suitable molecular weight.
  • the molecular weight values reported herein are the weight average molecular weight (M w ) of the resin.
  • the weight average molecular weight of the resin can be measured by known techniques using, for example, gel permeation chromatography (GPC) and standards of known molecular weight (e.g., polystyrene standards of known molecular weight).
  • GPC gel permeation chromatography
  • the molecular weights for all of the resins reported herein preferably are measured using such a GPC technique.
  • the first polysiloxane resin has a molecular weight of about 300 g/mole or more, about 400 g/mole or more, about 500 g/mole or more, about 600 g/mole or more, about 700 g/mole or more, about 800 g/mole or more, or about 900 g/mole or more.
  • the first polysiloxane resin preferably has a molecular weight of about 2,000 g/mole or less, about 1 ,900 g/mole or less, about 1 ,800 g/mole or less, about 1 ,700 g/mole or less, about 1 ,600 g/mole or less, about 1 ,500 g/mole or less, about 1 ,400 g/mole or less, about 1 ,300 g/mole or less, about 1 ,200 g/mole or less, or about 1 ,100 g/mole or less.
  • the first polysiloxane resin has a molecular weight of about 300 to about 1 ,500 g/mole, about 400 to about 1 ,400 g/mole, about 500 to about 1 ,300 g/mole, about 600 to about 1 ,200 g/mole, about 700 to about 1 ,100 g/mole, about 800 to about 1 ,100 g/mole, or about 900 to about 1 ,100 g/mole (e.g., about 1 ,000 g/mole).
  • the first polysiloxane resin can have any suitable functional hydrogen content.
  • the term "functional hydrogen content” refers to the amount of hydrogen atoms directly bonded to silicon atoms in the polysiloxane resin.
  • the first polysiloxane resin has a functional hydrogen content of about 0.1 mmole/g or more, about 0.5 mmole/g or more, about 1 mmole/g or more, about 2 mmole/g or more, about 3 mmole/g or more, about 4 mmole/g or more, about 5 mmole/g or more, about 6 mmole/g or more, about 7 mmole/g or more, or about 8 mmole/g or more.
  • the first polysiloxane resin preferably has a functional hydrogen content of about 36 mmole/g or less, about 30 mmole/g or less, about 25 mmole/g or less, about 20 mmole/g or less, about 15 mmole/g or less, or about 10 mmole/g or less.
  • the first polysiloxane resin has functional hydrogen content of about 0.1 to about 36 mmole/g, about 5 to about 25 mmole/g, about 6 to about 20 mmole/g, about 7 to about 15 mmole/g, or about 8 to about 10 mmole/g (e.g., about 9 mmole/g).
  • the second polysiloxane resin is an MQ resin comprising at least one repeating unit in which an alkyl group or alkenyl group is directly bonded to a silicon atom. More specifically, in such an embodiment, the second polysiloxane resin comprises at least one repeating unit conforming to the structure of Formula (I)
  • R 3 and R 4 are independently selected from the group consisting of alkyl groups (e.g., C- 1 -C 2 0 alkyl groups) and aryl groups (e.g., C 6 -C 2 o aryl groups).
  • Ri and R 2 are independently selected from the group consisting of C do alkyl groups, more preferably d-C 4 alkyl groups, with methyl groups being particularly preferred.
  • R 5 is selected from the group consisting of alkyl groups (e.g., C 1 -C 2 0 alkyl groups) and alkenyl groups (e.g., C-i-C-io alkenyl groups).
  • R 5 is selected from the group consisting of alkenyl groups (e.g., C do alkenyl groups), more preferably d-C 4 alkenyl groups, with vinyl groups being particular preferred.
  • the second polysiloxane resin can comprise additional repeating units in addition to those specifically noted above.
  • the second polysiloxane resin can also comprise one or more additional M units (i.e., one or more M units having a different structure than the structure of Formula (III)).
  • the first polysiloxane resin can further comprise one or more repeating units conforming to the structure of Formula (A)
  • the second polysiloxane resin can also comprise D units and/or T units, such as those described above in connection with the first polysiloxane resin.
  • the second polysiloxane resin consists essentially of repeating units conforming to the structure of Formula (I) and Formula (III).
  • the term "consists essentially of” means that the resin does not contain appreciable amounts of repeating units conforming to a different structure.
  • the first polysiloxane resin consists of repeating units conforming to the structure of Formula (I) and Formula (III).
  • the second polysiloxane resin can further comprise one or more M units having at least one hydrogen directly bonded to the silicon atom.
  • the second polysiloxane resin can further comprise at least one repeating unit conforming to the structure of Formula (II) as such structure is described above in connection with the first polysiloxane resin.
  • the repeating unit(s) of Formula (II) can be present in in the second polysiloxane resin in any suitable amount.
  • the repeating unit(s) of Formula (II) are present in the second polysiloxane resin in an amount sufficient to provide a functional hydrogen content falling within one of the ranges recited above for the first polysiloxane resin.
  • the second polysiloxane resin comprises at least one repeating unit conforming to Formula (II)
  • polysiloxane resin can optionally be omitted from the composition.
  • the second polysiloxane resin can have any suitable molecular weight.
  • the second polysiloxane resin has a molecular weight of about 2,000 g/mole or more, about 2,250 g/mole or more, about 2,500 g/mole or more, about 2,750 g/mole or more, about 3,000 g/mole or more, about 3,250 g/mole or more, about 3,500 g/mole or more, about 3,750 g/mole or more, or about 4,000 g/mole or more.
  • the second polysiloxane resin preferably has a molecular weight of about 20,000 g/mole or less, about 17,500 g/mole or less, about 15,000 g/mole or less, about 12,500 g/mole or less, about 10,000 g/mole or less, about 9,000 g/mole or less, about 8,000 g/mole or less, about 7,000 g/mole or less, about 6,000 g/mole or less, or about 5,000 g/mole or less (e.g., about 4,500 g/mole or less).
  • the second polysiloxane resin has a molecular weight of about 2,000 to about 20,000 g/mole, about 2,250 to about 17,500 g/mole, about 2,500 to about 15,000 g/mole, about 2,750 to about 12,500 g/mole, about 3,000 to about 10,000 g/mole, about 3,250 to about 9,000 g/mole, about 3,500 to about 8,000 g/mole, about 3,500 to about 7,000 g/mole, about 3,500 to about 6,000 g/mole, about 3,500 to about 5,000 g/mole, about 3,500 to about 4,500 g/mole, or about 4,000 to about 4,500 g/mole (e.g., about 4,300 g/mole).
  • a molecular weight of about 2,000 to about 20,000 g/mole, about 2,250 to about 17,500 g/mole, about 2,500 to about 15,000 g/mole, about 2,750 to about 12,500 g/mole, about 3,000 to about 10,000
  • the second polysiloxane resin can have any suitable functional alkenyl content.
  • functional alkenyl content refers to the amount of alkenyl groups directly bonded to silicon atoms in the polysiloxane resin.
  • the second polysiloxane resin has a functional alkenyl content of about 0.05 mmole/g or more, about 0.1 mmole/g or more, about 0.15 mmole/g or more, about 0.2 mmole/g or more, about 0.3 mmole/g or more, about 0.4 mmole/g or more, about 0.5 mmole/g or more, about 0.6 mmole/g or more, about 0.7 mmole/g or more, about 0.8 mmole/g or more, or about 0.9 mmole/g or more.
  • the second polysiloxane resin preferably has a functional alkenyl content of about 15 mmole/g or less, about 14 mmole/g or less, about 13 mmole/g or less, about 12 mmole/g or less, about 1 1 mmole/g or less, about 10 mmole/g or less, about 9 mmole/g or less, about 8 mmole/g or less, about 7 mmole/g or less, about 6 mmole/g or less, or about 5 mmole/g or less (e.g., about 2 mmole/g or less).
  • the second polysiloxane resin has a functional alkenyl content of about 0.05 to about 15 mmole/g, about 0.1 to about 14 mmole/g, about 0.15 to about 13 mmole/g, about 0.2 to about 12 mmole/g (e.g., about 0.2 to about 6 mmole/g), about 0.3 to about 1 1 mmole/g, about 0.4 to about 10 mmole/g, about 0.5 to about 9 mmole/g (e.g., about 0.5 to about 2 mmole/g), about 0.6 to about 8 mmole/g, about 0.7 to about 7 mmole/g, about 0.8 to about 6 mmole/g, about 0.9 to about 5 mmole/g (e.g., about 0.9 to about 2 mmole/g or about 1 mmole/g).
  • a functional alkenyl content of about 0.05 to about 15 mmole/g, about 0.1 to
  • the first polysiloxane resin and the second polysiloxane resin can be present in the composition in any suitable relative amounts.
  • the first polysiloxane resin comprises about 50% or less by weight of the combined total weight of the first polysiloxane resin and the second polysiloxane resin present in the composition. More preferably, the first polysiloxane resin comprises about 45% or less, about 40% or less, about 35% or less, about 30% or less, or about 25% or less by weight of the combined total weight of the first polysiloxane resin and the second polysiloxane resin present in the composition.
  • the first polysiloxane resin preferably comprises about 1 % or more, about 5% or more, about 10% or more, about 15% or more, or about 20% or more by weight of the combined total weight of the first polysiloxane resin and the second polysiloxane resin present in the composition.
  • the first polysiloxane resin comprises about 1 to about 50%, about 5 to about 45%, about 10 to about 40%, about 15 to about 35%, or about 15 to about 30% (e.g., about 15 to about 25%, about 20 to about 25%, or about 25%) by weight of the combined total weight of the first polysiloxane resin and the second polysiloxane resin present in the composition.
  • the first polysiloxane resin and the second polysiloxane resin can account for any suitable amount of the composition's total weight.
  • the total amount of the first polysiloxane resin and the second polysiloxane resin present in the composition is about 5% or more, about 10% or more, about 20% or more, about 30% or more, or about 35% or more of the total weight of the composition.
  • the total amount of the first polysiloxane resin and the second polysiloxane resin present in the composition preferably is about 75% or less, about 60% or less, about 50% or less, or about 45% or less of the total weight of the composition.
  • the total amount of the first polysiloxane resin and the second polysiloxane resin present in the composition is about 5 to about 75%, about 10 to about 60%, about 15 to about 50%, about 20 to about 45%, about 30 to about 45%, about 35 to about 45% (e.g., about 40%) of the total weight of the composition.
  • the first and second polysiloxane resins can be produced by processes known to those familiar with the art. For example, a process that is believed to be suitable for producing the resins is disclosed in U.S. Patent No.
  • the composition further comprises a solvent.
  • the solvent can be any suitable solvent.
  • the principal function of the solvent is provide a medium that allows the mixture of the first and second polysiloxane resins to be workable so that the mixture can be applied to the target substrate(s).
  • the solvent does not react with the first and second polysiloxane resins, has a relatively high vapor pressure at room temperature, and exhibits low toxicity or is non-toxic.
  • the solvent preferably is compatible with dental appliances and applications.
  • the solvent is selected from the group consisting of ethyl acetate, methyl acetate, acetone, and mixtures thereof.
  • the solvent can be present in the composition in any suitable amount. Generally, the amount of solvent in the composition is sufficient to render the composition workable and to aid application of the composition to the target substrate(s).
  • composition of the invention is believed to be well-suited for use as an adhesive.
  • Applicant believes that the composition is suitable for use as an adhesive for temporarily securing silicone dental impression materials to the trays used by dental professional in taking impressions using those materials.
  • the composition of the invention will provide a good balance of adhesion and release characteristics.
  • the composition will provide good adhesion between the impression material and the tray (e.g., metal or plastic tray), while also permitting the impression material to be removed from the tray after the impression is made. This is important because the silicone impression material can be damaged during the removal process if the adhesion between the tray and the impression material is too strong.
  • the adhesion is not strong enough, the impression material can separate from the tray while an impression is being made, making it difficult to obtain a useful impression.
  • the invention provides a method for using the composition described above. More specifically, the invention provides a method for using the composition as an adhesive for dental impression materials.
  • the method generally comprises the steps of: (a) providing a composition as described above; (b) providing a tray suitable for taking a dental impression or mold; (c) applying the composition to at least a portion of a surface of the tray; (d) allowing substantially all of the solvent in the composition applied to the substrate to evaporate; and (e) applying a dental impression material to the prepared tray (i.e., the tray to which the composition has been applied and allowed to dry).
  • the method can further comprise the steps of: (f) taking an impression of a patient's mouth and/or teeth using the tray to which the dental impression material has been applied; and/or (g) removing the dental impression material from the tray.
  • the tray and dental impression material used in the above-described method can be any suitable tray and dental impression material.
  • the dental impression material is a two-part room temperature vulcanizing (RTV) silicone impression material. It is believed that the materials disclosed in U.S. Patent No. 4,965,295 (Schwabe et al.) and U.S. Patent No.
  • the composition provides particularly good adhesion due to a combination of its physical and chemical properties. From the physical property standpoint, the mixture of the polysiloxane resins in the composition forms, in the absence of the solvent, a nearly solid mass that is also very tacky. This physical property is believed to be at least partially responsible for the good adhesion to the tray. From the chemical property standpoint, it is believed that the functional hydrogen in the first
  • polysiloxane resin and/or the functional alkenyl groups in the second polysiloxane resin can react with components present in the silicone impression material. This reaction will result in the formation of chemical "hooks" between the silicone impression material and the mass of adhesive, promoting a strong bond between the tray and impression material.

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Adhesives Or Adhesive Processes (AREA)

Abstract

La présente invention concerne une composition qui comprend une première résine de polysiloxane, une deuxième résine de polysiloxane, et un solvant. La première résine de polysiloxane comprend au moins un motif répétitif dans lequel un atome d'hydrogène est directement lié à un atome de silicium. La deuxième résine de polysiloxane comprend au moins un motif répétitif dans lequel un groupe alkyle ou un groupe alcényle (par exemple, un groupe vinyle) est directement lié à un atome de silicium.
PCT/US2013/052033 2012-10-08 2013-07-25 Composition adaptée pour utilisation en tant qu'adhésif WO2014058514A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US201261710968P 2012-10-08 2012-10-08
US61/710,968 2012-10-08

Publications (1)

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WO2014058514A1 true WO2014058514A1 (fr) 2014-04-17

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Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2676182A (en) 1950-09-13 1954-04-20 Dow Corning Copolymeric siloxanes and methods of preparing them
US4707531A (en) 1985-02-22 1987-11-17 Toray Silicone Co., Ltd. Method for producing organosilicon polymers and the polymers prepared thereby
US4965295A (en) 1984-03-23 1990-10-23 Bayer Aktiengesellschaft Dimensionally stable impression compositions
US6255407B1 (en) * 1998-10-13 2001-07-03 Ernst Muhlbauer Kg One-component adhesive
US6433057B1 (en) * 2000-03-28 2002-08-13 Dow Corning Corporation Silicone composition and electrically conductive silicone adhesive formed therefrom
US6998427B2 (en) 2001-06-14 2006-02-14 Rhodia Chimie Hydrophilic silicone elastomer material used in particular for taking dental imprints
US20090189180A1 (en) * 2008-01-24 2009-07-30 Shinji Murai Silicone resin composition

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2676182A (en) 1950-09-13 1954-04-20 Dow Corning Copolymeric siloxanes and methods of preparing them
US4965295A (en) 1984-03-23 1990-10-23 Bayer Aktiengesellschaft Dimensionally stable impression compositions
US4707531A (en) 1985-02-22 1987-11-17 Toray Silicone Co., Ltd. Method for producing organosilicon polymers and the polymers prepared thereby
US6255407B1 (en) * 1998-10-13 2001-07-03 Ernst Muhlbauer Kg One-component adhesive
US6433057B1 (en) * 2000-03-28 2002-08-13 Dow Corning Corporation Silicone composition and electrically conductive silicone adhesive formed therefrom
US6998427B2 (en) 2001-06-14 2006-02-14 Rhodia Chimie Hydrophilic silicone elastomer material used in particular for taking dental imprints
US20090189180A1 (en) * 2008-01-24 2009-07-30 Shinji Murai Silicone resin composition

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
"Silicones", 15 April 2003, ENCYCLOPEDIA OF POLYMER SCIENCE AND TECHNOLOGY, WILEY, US, PAGE(S) 765 - 841, XP007918236 *
GELEST INC: "REACTIVE SILICONES: FORGING NEW POLYMER LINKS", INTERNET CITATION, 2004, XP002470135, Retrieved from the Internet <URL:http://www.gelest.com/company/pdfs/reactivesilicones.pdf> [retrieved on 20080220] *

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