CA1338542C - Specimen mounting adhesive composition - Google Patents
Specimen mounting adhesive compositionInfo
- Publication number
- CA1338542C CA1338542C CA000435453A CA435453A CA1338542C CA 1338542 C CA1338542 C CA 1338542C CA 000435453 A CA000435453 A CA 000435453A CA 435453 A CA435453 A CA 435453A CA 1338542 C CA1338542 C CA 1338542C
- Authority
- CA
- Canada
- Prior art keywords
- composition
- tissue section
- cure
- refractive index
- oligomer
- 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.)
- Expired - Lifetime
Links
Classifications
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N1/00—Sampling; Preparing specimens for investigation
- G01N1/28—Preparing specimens for investigation including physical details of (bio-)chemical methods covered elsewhere, e.g. G01N33/50, C12Q
- G01N1/36—Embedding or analogous mounting of samples
-
- 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
- C09J163/00—Adhesives based on epoxy resins; Adhesives based on derivatives of epoxy resins
- C09J163/10—Epoxy resins modified by unsaturated compounds
Abstract
A composition is disclosed for transferring and adhering tape-mounted histological sections, to specimen mounting surfaces, usually glass microscope slides to expedite and simplify the safe removal of the mounting tape and the subsequent processing of the slide-mounted section. The composition is a curable polymeric mixture which has high tack prior to curing, is sub-stantially non-diffusable and non-flowable into tissue sections and, after curing, has a refractive index substantially similar to that of the specimen section and is non-labile to conven-tional histological solvents and stains. A preferred composition comprises diacrylate-terminated polyurethane, a diacrylate ester of an epoxy resin and a diethoxyacetophenone initiator. It is usually formed onto the mounting surface as a solution in a conventional organic solvent, such as isopropanol or toluene.
Description
BACKGROUND OF THE INVENTION
Field of the Invention This invention relates to the field of biological specimen mounting, and more particularly to adhesives for such use.
Description of the Prior Art Very thin slices of animal and plant tissue are prepared for many different kinds of microscopic studies by sectioning with a variety of kinds of microtomes. The tissue may be cut fresh.
The soft and compliant nature of most fresh tissue makes it very difficult to cut undistorted thin sections. If the tissue is frozen and is cut on a freezing microtome or in a cryostat at temperatures below 0C (32F), the hardness of the frozen water within the tissue permits sections to be cut relatively easily as thin as a few micrometers. However, these sections are brittle and friable and therefore difficult to handle and process further. To make sectioning of tissue still easier, a number of procedures produce a block of supported tissue which has superior sectioning properties and produce high quality, relatively easy-to-handle tissue sections. Such procedures typically involve: (1) Fixation of the tissue in a solution which insolubilizes the natural polymers of which tissue cells are composed, and which hardens them; (2) dehydration through a series of water-miscible (e.g., an alcohol) and then paraffin or plastic-monomer-miscible (e.g., toluene or xylene) solvents; (3) infiltration in melted paraffin or monomer solution; and (4) embedding by freezing the paraffin or polymerizing the monomer to form a rn/sg solid polymer. [St~i n; ng Methods, J.F.S. McManus and R.W. Mowry (P.B. Hoeber, Inc., N.Y. 1960); Techniques for Electron Micro-scopy, D. Kay, Ed. (Blackwell Sci. Publ., Oxford, England, 1965) pp. 166-212.]
However, there are occasional specimens which remain diffi-cult to section. As the section is cut, the parts of the cut often tend to section/fragment and fall from the cut section, or fall from the section as it is removed from the microtome.
. .
A. Palmgren, Nature, Vol. 174, p. 46 (1954), introduced the use of a conventional adhesive tape as a sectioning aid for the cutting of very large, hard or brittle specimens. A piece of adhesive tape is applied to the surface of a cut frozen or paraffin block, just before the specimen is advanced the incre-mental thickness of a (next) section. The microtome advances and the next section is cut and is thus supported by the applied tape. The quality of the uncompressed section of hard brittle and friable tissue produced by this means can be far superior to that of a conventional section of the same block of tissue.
However, following Palmgren, processing such a section while it remains on the tape, or transferring it to a glass slide (to permit it to be processed thereafter in a conventional way) involved elaborate, time-consuming and inconvenient methods, which are also potentially damaging to the section. Palmgren's method, therefore, did not become popular.
W. E. Beckel, Nature, Vol. 184, p. 1584 (1959) introduced the use of Scotch* brand No. 810 cellulose-acetate-backed adhesive tape in Palmgren's process. The tape-mounted sections were applied, section-side down on conventionally wet albuminized glass slides. After thorough drying for a few hours, the adhesive backing, the adhesive layer and the paraffin were all dissolved *trade mark .
'~A~ B
in tetrahydrofuran in 30 minutes, leaving the section adhering to the glass slide, and available for further processing by conventional techniques. Alternatively, chloroform for 2 minut-:S, followed by xylene for 30 minutes, worked equally well. Beckel also described a "more rapid method" which used a film of albumin and a solution of 2 per cent celloidin in methyl benzoate or ethyl alcohol to "cement" the section to the glass slide followed by 1 minute in chloroform and 10 minutes in xylene to complete the treatment. Some other equally time-consuming variations were described.
D. S. Gowers and R. E. Miller, Nature, Vol. 190, p. 425 (1961), attempted to repeat Beckel's method but found that, with available Scotch brand No. 810 tape, the adhesive could not be dissolved, and with the best alternate available tape, ~uck brand No. 200, safe removal of the tape without damaging the section in solvent took from 1 to 10 hours.
R. P. Wedeen and H. I. Jernow, Am. J. Physiol., Vol. 214, p. 776 (1968) used cyanoacrylate (Eastman 910 "super-glue") to attach adhesive-tape-supported frozen sections to radioautographic (photographic) plates. The cyanoacrylate is initially liquid, but polymerizes to a solid when it is squeezed out into a thin film. The cyanoacrylate polymer is soluble in xylene and other processing solvents, which would cause the section to float free, and so is not useful for ordinary use.
In another area of study relating to the field of specirnen section handling, various resinous mounting media have been developed. After the tissue section has been stained, the slide is transferred from water through alcoholic and then resin-compatible solvents, such as ~ylene, and the section is mounted *trade mark 2401-A ~4~
in a resinous medium chosen to have a refractive index which closely approximates the average refractive index of the unstained tissue specimens, e.g., a refractive index from about 1.530 to about 1.570. Such are described, for example, in V. S. Patent No. 4,120,991, and McManus & Mowry, above.
__ SUMMARY OF THE INVENTION
To achieve heretofore unavailable advantages which expedite and simplify the processing of tape-mounted specimen sections, the invention in one aspect provides an adhesive composition for transferring and mounting a tape-supported thin histological tissue section onto a specimen support for further processing, comprising one polymerizable difunctional oligomer having acryl or methacryl functional groups and a polymerization curing initiator therefor and which composition has the following characteristics: a) is a high tack pressure-sensitive adhesive before cure and at the temperature of use; b) has a sufficiently low diffusion coefficient before cure and at the temperature of use to be substantially non-diffusible into a thin tissue section;
c) has a viscosity which is sufficiently high before cure and at the temperature of use to be substantially non-flowable into the tissue section during application of the tissue section to the surface of the specimen support; d) may be rapidly cured; e) is substantially non-swelling, tack-free, insoluble, unreactive and non-ionic, after cure; f) has a cured refractive index between about 1.53 and about 1.56; and g) after cure, bonds strongly to both the surface of the thin tissue section and the support surface.
In a further aspect the invention provides an adhesive composition for transferring and mounting a tape-supported thin histological tissue section onto a specimen support for further processing, comprising at least one rn/sg ~r ~ 9,.
`- 1 338542 difunctional oligomer and one or more other polymerizable components each having acryl or methacryl functional groups wherein the polymerizable components are chosen such that their cured refractive indices permit mixing in such proportions as to provide a refractive index of the cured composition in the range from about 1.53 to about 1.56, the composition further comprising a polymerization curing initiator therefor and which composition has the following characteristics: a) is a high tack pressure-sensitive adhesive before cure and at the temperature of use; b) has a sufficiently low diffusion coefficient before cure and at the temperature of use to be substantially non-diffusable into a thin tissue section;
c) has a viscosity which is sufficiently high before cure and at the temperature of use to be substantially non-flowable into the tissue section during application of the tissue section to rn~/ b~
~~~ the surface of the specimen support; d) ~rapidly cured;
e) is substantially non-swelling, tack-free, insoluble, unreactive and non-ionic, after cure; f) after cure, bonds strongly to both the surface of the thin tissue section and the support surface.
Such curable adhesive composition is typically coated onto a glass microscope slide. A cut paraffin embedded section, supported on adhesive tape, is pressed, section-side down, onto the - 6a -rm/ B
adhesive-coated glass microscope slide. The contact is assured by smoothing with moderate finger pressure. The laminate, bottom-of-the-glass-side up, is placed within a few inches of a 4-watt black-light fluorescent lamp with a phosphor peak-light output near 350 nm, for 3 minutes. The laminate is then immersed in a solvent, such as xylene, and the adhesive tape is gently peeled away over a period of about 5 seconds. The very strong bond between the bottom of the section and the glass slide make this otherwise critical step very easy. The solvent greatly weakens the tape-adhesive-to-tissue and the tape-adhesive-to-tape-backing bonds. Any L~ -ining adhesive layer from the tape and the paraffin are dissolved away in about one minute with gentle agitation, and the slide is ready for processing in the conventional manner. However- for a detailed description of the method, reference is made to commonly assigned, copending Canadian application serial no. 435,452, filed on even date herewith.
.r~i ?
DESCRIPTION OF T~E PREFERRED EMBODIMENTS
In a preferred embodiment, the Composition of the present invention is a curable polymeric mixture which has the high tack of a pressure-sensitive adhesive prior to curing, is substantially non-diffusable into tissue sections and, after curing, has a refractive index substantially similar to that of the tissue section and is non-labile to conventional histological solvents and stains. A preferred co~position comprises a diacrylate-terminated polyurethane, a diacrylate ester of an epoxy resin and a diethoxyacetophenone initiator. It is usually formed onto the mounting surface of the specimen support as a solution in a con-ventional organic solvent, such as toluene or isopropanol.
The preferred composition suitable to achieve the above objectives comprises a mixture of high molecular weight inter-reactive oligomers. The high molecular weight assures both high viscosity and low diffusion coefficient. The upper limitation of the molecular weight is such that there remains high tack in the precured mixture when coated on a mounting surface. In one preferred : -~i t, the mixture includes a first oligomer having a cured refractive index above 1.560 and another that has a cured refractive index less than 1.530, for example, an oligo-meric diacrylate ester of an epoxy resin and a polyurethane diacrylate oligomer, respectively. Both cured resins must be resistant to histological stains and solvents. Preferably, both resins are provided with terminal acryl or methacryl groups to permit radical initiated cross-linked polymerization. These oligomer resins are mixed in proportions, more fully described below, which provide a cured refractive index between about 1.530 and about 1.560, using the Dale-Gladstone equation described in standard physical chemistry texts and procedures.
~_ Components particularly preferred in forming the composition of the invention include those of low refractive index such as diacrylate-terminated polyurethanes, including Purelast~
190, 186 and 169, available from Polymer Systems Corporation, Little Falls, New Jersey, in combination with those of high refractive index such as diacrylate esters of epoxy resins, such as Epicryl~ 370 resin and Shell Developmental Polyester Resin DRH 301.1~, both available from Shell Corporation, a division of Shell Oil Company, Houston, Texas.
A further essential component of the composition is an initiator, such as a thermal initiator or preferably a photo-initiator. A thermal initiator, such as benzoyl peroxide, acetylperoxide or azoisobutyronitrile may be included, if curing is to be effected thermally. When cured in this manner, it is preferable to add the initiator just prior to curing. The thermal treatment is effectively achieved by heating at a temperature from about 40C to about 200C. Alternatively, a broad spectrum of photoinitiators can be used including benzoin and acetophenones such as 2,2-dimethoxy-2-phenylacetophenone and 2,2-diethoxy-acetophenone. The preferred photoinitiator for use with the above polymer mixture is 2,2-diethoxyacetophenone, available from the Upjohn Company, Fine Chemical Division, New Haven, Connecticut.
Toluene and isopropanol are standard commercially available reagent grade solvents.
Typical proportions of the epoxy ester to the urethane resin is from about 2:1 to about 3:1 by weight. The ratio of the combined resins to the initiator component is approximately 20:1 by weight. About 0.5 grams per milliliter of the mixture of the above two resins in an appropriate solvent is preferred.
rn/sg ~L
~ 338542 Other combinations of reactive oligomer and/or polymer systems such as yield epoxy resins, polyurethanes, polyesters, etc., with other initiators and solvents can be formulated by those skilled in the art to fill the requirements in the listed specifications.
The composition of thé invention is suitable for layering on specimen supports such as glass microscope slides. It can be layered by printing, spraying or spreading in film-forming solvents which thereafter evaporate. In one preferred embodiment, the composition is coated by hand, using a blade coating device, or by r~~^hine, using techniques such as dip or bead coating.
If r-^hin^ coating is used, hopper coating techniques, such as are known in the photographic industry, are preferred.
The thickness of any layer and its degree of permeability are widely variable and dependent on actual use. Dry thickness of the adhesive prior to curing is from about 10 to about 25 micrometers.
Field of the Invention This invention relates to the field of biological specimen mounting, and more particularly to adhesives for such use.
Description of the Prior Art Very thin slices of animal and plant tissue are prepared for many different kinds of microscopic studies by sectioning with a variety of kinds of microtomes. The tissue may be cut fresh.
The soft and compliant nature of most fresh tissue makes it very difficult to cut undistorted thin sections. If the tissue is frozen and is cut on a freezing microtome or in a cryostat at temperatures below 0C (32F), the hardness of the frozen water within the tissue permits sections to be cut relatively easily as thin as a few micrometers. However, these sections are brittle and friable and therefore difficult to handle and process further. To make sectioning of tissue still easier, a number of procedures produce a block of supported tissue which has superior sectioning properties and produce high quality, relatively easy-to-handle tissue sections. Such procedures typically involve: (1) Fixation of the tissue in a solution which insolubilizes the natural polymers of which tissue cells are composed, and which hardens them; (2) dehydration through a series of water-miscible (e.g., an alcohol) and then paraffin or plastic-monomer-miscible (e.g., toluene or xylene) solvents; (3) infiltration in melted paraffin or monomer solution; and (4) embedding by freezing the paraffin or polymerizing the monomer to form a rn/sg solid polymer. [St~i n; ng Methods, J.F.S. McManus and R.W. Mowry (P.B. Hoeber, Inc., N.Y. 1960); Techniques for Electron Micro-scopy, D. Kay, Ed. (Blackwell Sci. Publ., Oxford, England, 1965) pp. 166-212.]
However, there are occasional specimens which remain diffi-cult to section. As the section is cut, the parts of the cut often tend to section/fragment and fall from the cut section, or fall from the section as it is removed from the microtome.
. .
A. Palmgren, Nature, Vol. 174, p. 46 (1954), introduced the use of a conventional adhesive tape as a sectioning aid for the cutting of very large, hard or brittle specimens. A piece of adhesive tape is applied to the surface of a cut frozen or paraffin block, just before the specimen is advanced the incre-mental thickness of a (next) section. The microtome advances and the next section is cut and is thus supported by the applied tape. The quality of the uncompressed section of hard brittle and friable tissue produced by this means can be far superior to that of a conventional section of the same block of tissue.
However, following Palmgren, processing such a section while it remains on the tape, or transferring it to a glass slide (to permit it to be processed thereafter in a conventional way) involved elaborate, time-consuming and inconvenient methods, which are also potentially damaging to the section. Palmgren's method, therefore, did not become popular.
W. E. Beckel, Nature, Vol. 184, p. 1584 (1959) introduced the use of Scotch* brand No. 810 cellulose-acetate-backed adhesive tape in Palmgren's process. The tape-mounted sections were applied, section-side down on conventionally wet albuminized glass slides. After thorough drying for a few hours, the adhesive backing, the adhesive layer and the paraffin were all dissolved *trade mark .
'~A~ B
in tetrahydrofuran in 30 minutes, leaving the section adhering to the glass slide, and available for further processing by conventional techniques. Alternatively, chloroform for 2 minut-:S, followed by xylene for 30 minutes, worked equally well. Beckel also described a "more rapid method" which used a film of albumin and a solution of 2 per cent celloidin in methyl benzoate or ethyl alcohol to "cement" the section to the glass slide followed by 1 minute in chloroform and 10 minutes in xylene to complete the treatment. Some other equally time-consuming variations were described.
D. S. Gowers and R. E. Miller, Nature, Vol. 190, p. 425 (1961), attempted to repeat Beckel's method but found that, with available Scotch brand No. 810 tape, the adhesive could not be dissolved, and with the best alternate available tape, ~uck brand No. 200, safe removal of the tape without damaging the section in solvent took from 1 to 10 hours.
R. P. Wedeen and H. I. Jernow, Am. J. Physiol., Vol. 214, p. 776 (1968) used cyanoacrylate (Eastman 910 "super-glue") to attach adhesive-tape-supported frozen sections to radioautographic (photographic) plates. The cyanoacrylate is initially liquid, but polymerizes to a solid when it is squeezed out into a thin film. The cyanoacrylate polymer is soluble in xylene and other processing solvents, which would cause the section to float free, and so is not useful for ordinary use.
In another area of study relating to the field of specirnen section handling, various resinous mounting media have been developed. After the tissue section has been stained, the slide is transferred from water through alcoholic and then resin-compatible solvents, such as ~ylene, and the section is mounted *trade mark 2401-A ~4~
in a resinous medium chosen to have a refractive index which closely approximates the average refractive index of the unstained tissue specimens, e.g., a refractive index from about 1.530 to about 1.570. Such are described, for example, in V. S. Patent No. 4,120,991, and McManus & Mowry, above.
__ SUMMARY OF THE INVENTION
To achieve heretofore unavailable advantages which expedite and simplify the processing of tape-mounted specimen sections, the invention in one aspect provides an adhesive composition for transferring and mounting a tape-supported thin histological tissue section onto a specimen support for further processing, comprising one polymerizable difunctional oligomer having acryl or methacryl functional groups and a polymerization curing initiator therefor and which composition has the following characteristics: a) is a high tack pressure-sensitive adhesive before cure and at the temperature of use; b) has a sufficiently low diffusion coefficient before cure and at the temperature of use to be substantially non-diffusible into a thin tissue section;
c) has a viscosity which is sufficiently high before cure and at the temperature of use to be substantially non-flowable into the tissue section during application of the tissue section to the surface of the specimen support; d) may be rapidly cured; e) is substantially non-swelling, tack-free, insoluble, unreactive and non-ionic, after cure; f) has a cured refractive index between about 1.53 and about 1.56; and g) after cure, bonds strongly to both the surface of the thin tissue section and the support surface.
In a further aspect the invention provides an adhesive composition for transferring and mounting a tape-supported thin histological tissue section onto a specimen support for further processing, comprising at least one rn/sg ~r ~ 9,.
`- 1 338542 difunctional oligomer and one or more other polymerizable components each having acryl or methacryl functional groups wherein the polymerizable components are chosen such that their cured refractive indices permit mixing in such proportions as to provide a refractive index of the cured composition in the range from about 1.53 to about 1.56, the composition further comprising a polymerization curing initiator therefor and which composition has the following characteristics: a) is a high tack pressure-sensitive adhesive before cure and at the temperature of use; b) has a sufficiently low diffusion coefficient before cure and at the temperature of use to be substantially non-diffusable into a thin tissue section;
c) has a viscosity which is sufficiently high before cure and at the temperature of use to be substantially non-flowable into the tissue section during application of the tissue section to rn~/ b~
~~~ the surface of the specimen support; d) ~rapidly cured;
e) is substantially non-swelling, tack-free, insoluble, unreactive and non-ionic, after cure; f) after cure, bonds strongly to both the surface of the thin tissue section and the support surface.
Such curable adhesive composition is typically coated onto a glass microscope slide. A cut paraffin embedded section, supported on adhesive tape, is pressed, section-side down, onto the - 6a -rm/ B
adhesive-coated glass microscope slide. The contact is assured by smoothing with moderate finger pressure. The laminate, bottom-of-the-glass-side up, is placed within a few inches of a 4-watt black-light fluorescent lamp with a phosphor peak-light output near 350 nm, for 3 minutes. The laminate is then immersed in a solvent, such as xylene, and the adhesive tape is gently peeled away over a period of about 5 seconds. The very strong bond between the bottom of the section and the glass slide make this otherwise critical step very easy. The solvent greatly weakens the tape-adhesive-to-tissue and the tape-adhesive-to-tape-backing bonds. Any L~ -ining adhesive layer from the tape and the paraffin are dissolved away in about one minute with gentle agitation, and the slide is ready for processing in the conventional manner. However- for a detailed description of the method, reference is made to commonly assigned, copending Canadian application serial no. 435,452, filed on even date herewith.
.r~i ?
DESCRIPTION OF T~E PREFERRED EMBODIMENTS
In a preferred embodiment, the Composition of the present invention is a curable polymeric mixture which has the high tack of a pressure-sensitive adhesive prior to curing, is substantially non-diffusable into tissue sections and, after curing, has a refractive index substantially similar to that of the tissue section and is non-labile to conventional histological solvents and stains. A preferred co~position comprises a diacrylate-terminated polyurethane, a diacrylate ester of an epoxy resin and a diethoxyacetophenone initiator. It is usually formed onto the mounting surface of the specimen support as a solution in a con-ventional organic solvent, such as toluene or isopropanol.
The preferred composition suitable to achieve the above objectives comprises a mixture of high molecular weight inter-reactive oligomers. The high molecular weight assures both high viscosity and low diffusion coefficient. The upper limitation of the molecular weight is such that there remains high tack in the precured mixture when coated on a mounting surface. In one preferred : -~i t, the mixture includes a first oligomer having a cured refractive index above 1.560 and another that has a cured refractive index less than 1.530, for example, an oligo-meric diacrylate ester of an epoxy resin and a polyurethane diacrylate oligomer, respectively. Both cured resins must be resistant to histological stains and solvents. Preferably, both resins are provided with terminal acryl or methacryl groups to permit radical initiated cross-linked polymerization. These oligomer resins are mixed in proportions, more fully described below, which provide a cured refractive index between about 1.530 and about 1.560, using the Dale-Gladstone equation described in standard physical chemistry texts and procedures.
~_ Components particularly preferred in forming the composition of the invention include those of low refractive index such as diacrylate-terminated polyurethanes, including Purelast~
190, 186 and 169, available from Polymer Systems Corporation, Little Falls, New Jersey, in combination with those of high refractive index such as diacrylate esters of epoxy resins, such as Epicryl~ 370 resin and Shell Developmental Polyester Resin DRH 301.1~, both available from Shell Corporation, a division of Shell Oil Company, Houston, Texas.
A further essential component of the composition is an initiator, such as a thermal initiator or preferably a photo-initiator. A thermal initiator, such as benzoyl peroxide, acetylperoxide or azoisobutyronitrile may be included, if curing is to be effected thermally. When cured in this manner, it is preferable to add the initiator just prior to curing. The thermal treatment is effectively achieved by heating at a temperature from about 40C to about 200C. Alternatively, a broad spectrum of photoinitiators can be used including benzoin and acetophenones such as 2,2-dimethoxy-2-phenylacetophenone and 2,2-diethoxy-acetophenone. The preferred photoinitiator for use with the above polymer mixture is 2,2-diethoxyacetophenone, available from the Upjohn Company, Fine Chemical Division, New Haven, Connecticut.
Toluene and isopropanol are standard commercially available reagent grade solvents.
Typical proportions of the epoxy ester to the urethane resin is from about 2:1 to about 3:1 by weight. The ratio of the combined resins to the initiator component is approximately 20:1 by weight. About 0.5 grams per milliliter of the mixture of the above two resins in an appropriate solvent is preferred.
rn/sg ~L
~ 338542 Other combinations of reactive oligomer and/or polymer systems such as yield epoxy resins, polyurethanes, polyesters, etc., with other initiators and solvents can be formulated by those skilled in the art to fill the requirements in the listed specifications.
The composition of thé invention is suitable for layering on specimen supports such as glass microscope slides. It can be layered by printing, spraying or spreading in film-forming solvents which thereafter evaporate. In one preferred embodiment, the composition is coated by hand, using a blade coating device, or by r~~^hine, using techniques such as dip or bead coating.
If r-^hin^ coating is used, hopper coating techniques, such as are known in the photographic industry, are preferred.
The thickness of any layer and its degree of permeability are widely variable and dependent on actual use. Dry thickness of the adhesive prior to curing is from about 10 to about 25 micrometers.
Claims (17)
1. An adhesive composition for transferring and mounting a tape-supported thin histological tissue section onto a specimen support for further processing, comprising one polymerizable difunctional oligomer having acryl or methacryl functional groups and a polymerization curing initiator therefor and which composition has the following characteristics:
a. is a high tack pressure-sensitive adhesive before cure and at the temperature of use;
b. has a sufficiently low diffusion coefficient before cure and at the temperature of use to be substantially non-diffusible into said thin tissue section;
c. has a viscosity which is sufficiently high before cure and at the temperature of use to be substantially non-flowable into said tissue section during application of said tissue section to the surface of said specimen support;
d. may be rapidly cured;
e. is substantially non-swelling, tack-free, insoluble, unreactive and non-ionic, after cure;
f. has a cured refractive index between about 1.53 and about 1.56; and g. after cure, bonds strongly to both the surface of said thin tissue section and said support surface.
a. is a high tack pressure-sensitive adhesive before cure and at the temperature of use;
b. has a sufficiently low diffusion coefficient before cure and at the temperature of use to be substantially non-diffusible into said thin tissue section;
c. has a viscosity which is sufficiently high before cure and at the temperature of use to be substantially non-flowable into said tissue section during application of said tissue section to the surface of said specimen support;
d. may be rapidly cured;
e. is substantially non-swelling, tack-free, insoluble, unreactive and non-ionic, after cure;
f. has a cured refractive index between about 1.53 and about 1.56; and g. after cure, bonds strongly to both the surface of said thin tissue section and said support surface.
2. An adhesive composition for transferring and mounting a tape-supported thin histological tissue section onto a specimen support for further processing, comprising at least one difunctional oligomer and one or more other polymerizable components each having acryl or methacryl functional groups wherein said polymerizable components are chosen such that their cured refractive indices permit mixing in such proportions as to provide a refractive index of the cured composition in the range from about 1.53 to about 1.56, said composition further comprising a polymerization curing initiator therefor and which composition has the following characteristics:
a. is a high tack pressure-sensitive adhesive before cure and at the temperature of use;
b. has a sufficiently low diffusion coefficient before cure and at the temperature of use to be substantially non-diffusible into said thin tissue section;
c. has a viscosity which is sufficiently high before cure and at the temperature of use to be substantially non-flowable into said tissue section during application of said tissue section to the surface of said specimen support;
d. may be rapidly cured;
e. is substantially non-swelling, tack-free, insoluble, unreactive and non-ionic, after cure;
f. after cure, bonds strongly to both the surface of said thin tissue section and said support surface.
a. is a high tack pressure-sensitive adhesive before cure and at the temperature of use;
b. has a sufficiently low diffusion coefficient before cure and at the temperature of use to be substantially non-diffusible into said thin tissue section;
c. has a viscosity which is sufficiently high before cure and at the temperature of use to be substantially non-flowable into said tissue section during application of said tissue section to the surface of said specimen support;
d. may be rapidly cured;
e. is substantially non-swelling, tack-free, insoluble, unreactive and non-ionic, after cure;
f. after cure, bonds strongly to both the surface of said thin tissue section and said support surface.
3. The composition of claim 2 wherein said polymerizable components comprises a mixture of oligomers.
4. The composition of claim 3 wherein said mixture of oligomers comprises at least one oligomer having a low refractive index and at least one oligomer having a high refractive index.
5. The composition of claim 4 wherein at least one oligomer has a cured refractive index above about 1.560 and another oligomer has a cured refractive index less than about 1.530.
6. The composition of claim 5 which comprises at least one oligomeric acrylate ester of an epoxy resin and at least one polyurethane acrylate oligomer.
7. The composition of claim 6 wherein said oligomeric acrylate ester of an epoxy resin is a diacrylate ester.
8. The composition of claim 7 wherein both oligomers are provided with terminal acryl or methacryl groups.
9. The composition of claim 8 wherein the epoxy ester and the urethane resin are present in a ratio of from about 2:1 to about 3:1 by weight.
10. The composition of claim 2 wherein said polymerization curing initiator is a photoinitiator.
11. The composition of claim 10 wherein said photoinitiator is selected from the group consisting of benzoin and acetophenones.
12. The composition of claim 11 wherein said acetophenone is 2,2-dimethoxy-2-phenylacetophenone.
13. The composition of claim 11 wherein said acetophenone is 2,2-diethoxyacetophenone.
14. The composition of claim 2 wherein said polymerization curing initiator is a thermal initiator.
15. The composition of claim 14 wherein said thermal initiator is benzoyl peroxide.
16. The composition of claim 14 wherein said thermal initiator is acetylperoxide.
17. The composition of claim 14 wherein said thermal initiator is azoisobutyronitrile.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US41725482A | 1982-09-13 | 1982-09-13 | |
| US06/417,254 | 1982-09-13 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1338542C true CA1338542C (en) | 1996-08-20 |
Family
ID=23653200
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000435453A Expired - Lifetime CA1338542C (en) | 1982-09-13 | 1983-08-26 | Specimen mounting adhesive composition |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US5444105A (en) |
| EP (1) | EP0104825B1 (en) |
| JP (1) | JPS59117571A (en) |
| AU (1) | AU577261B2 (en) |
| CA (1) | CA1338542C (en) |
| DE (1) | DE3379238D1 (en) |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3426043A1 (en) * | 1984-07-14 | 1986-01-16 | Kulzer & Co GmbH, 6393 Wehrheim | PHOTOPOLYMERIZABLE MATERIAL FOR EMBEDDING GRINDING SAMPLES |
| JPH02142813A (en) * | 1988-09-30 | 1990-05-31 | Westinghouse Electric Corp <We> | Ultraviolet-curing resin composition |
| AU6164496A (en) * | 1995-06-07 | 1996-12-30 | Jacques Michael Casparian | Method of optimizing tissue for histopathologic examination |
| US6087134A (en) * | 1997-01-14 | 2000-07-11 | Applied Imaging Corporation | Method for analyzing DNA from a rare cell in a cell population |
| US6110761A (en) * | 1997-08-05 | 2000-08-29 | Micron Technology, Inc. | Methods for simultaneously electrically and mechanically attaching lead frames to semiconductor dice and the resulting elements |
| US6097092A (en) * | 1998-04-22 | 2000-08-01 | International Business Machines Corporation | Freestanding multilayer IC wiring structure |
| US7335965B2 (en) | 1999-08-25 | 2008-02-26 | Micron Technology, Inc. | Packaging of electronic chips with air-bridge structures |
| US6709968B1 (en) | 2000-08-16 | 2004-03-23 | Micron Technology, Inc. | Microelectronic device with package with conductive elements and associated method of manufacture |
| US6670719B2 (en) | 1999-08-25 | 2003-12-30 | Micron Technology, Inc. | Microelectronic device package filled with liquid or pressurized gas and associated method of manufacture |
| US6433413B1 (en) | 2001-08-17 | 2002-08-13 | Micron Technology, Inc. | Three-dimensional multichip module |
| US6747347B2 (en) * | 2001-08-30 | 2004-06-08 | Micron Technology, Inc. | Multi-chip electronic package and cooling system |
| US6686654B2 (en) * | 2001-08-31 | 2004-02-03 | Micron Technology, Inc. | Multiple chip stack structure and cooling system |
| US6620638B1 (en) | 2002-06-05 | 2003-09-16 | Micron Technology, Inc. | Testing of multi-chip electronic modules |
| DE10359705A1 (en) * | 2003-12-18 | 2005-07-14 | Wacker-Chemie Gmbh | Addition-crosslinking silicone resin compositions |
| US7300821B2 (en) * | 2004-08-31 | 2007-11-27 | Micron Technology, Inc. | Integrated circuit cooling and insulating device and method |
| US10473557B2 (en) | 2015-06-30 | 2019-11-12 | Clarapath, Inc. | Method, system, and device for automating transfer of tape to microtome sections |
| US10571368B2 (en) | 2015-06-30 | 2020-02-25 | Clarapath, Inc. | Automated system and method for advancing tape to transport cut tissue sections |
| US10446260B2 (en) | 2015-12-07 | 2019-10-15 | Clarapath, Inc. | Spatially indexed tissue biobank with microscopic phenotype-based retrieval system |
| US10724929B2 (en) | 2016-05-13 | 2020-07-28 | Clarapath, Inc. | Automated tissue sectioning and storage system |
| DE102016009908A1 (en) * | 2016-08-18 | 2018-02-22 | Orsatec Gmbh | UV-curable mounting agent |
| WO2019110078A1 (en) | 2017-12-06 | 2019-06-13 | Orsatec Gmbh | Uv curable mounting medium |
| CN109705786A (en) * | 2018-12-26 | 2019-05-03 | 上海熙邦新材料有限公司 | Binder used for optical communication device |
| CN111662654A (en) * | 2020-07-23 | 2020-09-15 | 北京高盟新材料股份有限公司 | Long-operation-time two-component acrylate structural adhesive and preparation method thereof |
| CN113484109A (en) * | 2021-06-30 | 2021-10-08 | 艾佧科技(北京)有限公司 | Novel method for preparing abrasive disc for implanting active metal bone tissue |
Family Cites Families (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3450613A (en) * | 1964-03-09 | 1969-06-17 | Bausch & Lomb | Epoxy adhesive containing acrylic acid-epoxy reaction products and photosensitizers |
| US3466209A (en) * | 1964-07-15 | 1969-09-09 | Newton G Leveskis | Method of preparing microscope slides using terpolymers of vinyl benzene;methyl methacrylate,and acrylate ester |
| US3709866A (en) * | 1970-06-01 | 1973-01-09 | Dentsply Int Inc | Photopolymerizable dental products |
| JPS4826844B1 (en) * | 1970-11-17 | 1973-08-16 | ||
| US4165265A (en) * | 1973-07-17 | 1979-08-21 | Nippon Paint Co., Ltd. | Multi-stage irradiation method of curing a photocurable coating composition |
| JPS5069143A (en) * | 1973-10-09 | 1975-06-09 | ||
| US3891327A (en) * | 1973-11-01 | 1975-06-24 | Grace W R & Co | Mounted slides and method of securing a cover glass to a glass slide having a specimen thereon |
| US3939019A (en) * | 1974-08-02 | 1976-02-17 | Pickett John E P | Covering apparatus and method for film mounted serial tissue sections |
| JPS51125138A (en) * | 1974-08-05 | 1976-11-01 | Chem Kagaku Kogyosho:Kk | Thermosetting adhesive composition showing tackiness at normal tempera tvre and conpition |
| US4052282A (en) * | 1975-10-08 | 1977-10-04 | Mitsubishi Petrochemical Co., Ltd. | Photocurable flexible orthopedic bandage |
| US4120991A (en) * | 1976-12-10 | 1978-10-17 | Technicon Instruments Corporation | Process for mounting tissue sections with an U.V. light curable mounting medium |
| US4257346A (en) * | 1976-12-10 | 1981-03-24 | Technicon Instruments Corp. | Apparatus for mounting tissue sections with an U.V. light curable mounting medium |
| JPS605627B2 (en) * | 1977-03-25 | 1985-02-13 | 積水化学工業株式会社 | Heat-curable pressure-sensitive adhesive |
| EP0012776B1 (en) * | 1978-12-21 | 1982-12-15 | Firma Carl Freudenberg | Process for bonding non-woven fabrics |
| FR2456134A1 (en) * | 1979-05-10 | 1980-12-05 | Commissariat Energie Atomique | ADHESIVE COMPOSITION FOR USE IN PARTICULAR FOR JOINING ELEMENTS OF THE SAME OR DIFFERENT MATERIALS |
| US4287255A (en) * | 1979-09-06 | 1981-09-01 | Avery International Corporation | Reinforced adhesive tapes |
| JPS56108935A (en) * | 1980-01-31 | 1981-08-28 | Canon Inc | Method for making sample for microscopic observation |
| US4317858A (en) * | 1980-06-27 | 1982-03-02 | Westinghouse Electric Corp. | Ultraviolet curable solvent-free wire enamel blends |
| MX173523B (en) * | 1981-11-02 | 1994-03-11 | Gencorp Inc | IMPROVEMENTS IN THERMOSURING COATING COMPOSITION AND METHOD |
| JPS58167695A (en) * | 1982-03-29 | 1983-10-03 | Arai Pump Mfg Co Ltd | Material for sliding parts |
-
1983
- 1983-08-26 CA CA000435453A patent/CA1338542C/en not_active Expired - Lifetime
- 1983-09-05 AU AU18696/83A patent/AU577261B2/en not_active Ceased
- 1983-09-12 DE DE8383305305T patent/DE3379238D1/en not_active Expired
- 1983-09-12 EP EP83305305A patent/EP0104825B1/en not_active Expired
- 1983-09-13 JP JP58167694A patent/JPS59117571A/en active Granted
-
1993
- 1993-07-30 US US08/100,333 patent/US5444105A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JPS59117571A (en) | 1984-07-06 |
| JPH0555557B2 (en) | 1993-08-17 |
| AU1869683A (en) | 1984-03-22 |
| DE3379238D1 (en) | 1989-03-30 |
| US5444105A (en) | 1995-08-22 |
| AU577261B2 (en) | 1988-09-22 |
| EP0104825B1 (en) | 1989-02-22 |
| EP0104825A1 (en) | 1984-04-04 |
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