US2403458A - Solvent extraction of drying oils - Google Patents
Solvent extraction of drying oils Download PDFInfo
- Publication number
- US2403458A US2403458A US2403458DA US2403458A US 2403458 A US2403458 A US 2403458A US 2403458D A US2403458D A US 2403458DA US 2403458 A US2403458 A US 2403458A
- Authority
- US
- United States
- Prior art keywords
- oil
- drying
- oils
- solvent
- ethanol
- 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
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- 239000003921 oil Substances 0.000 title description 108
- 238000001035 drying Methods 0.000 title description 70
- 238000000638 solvent extraction Methods 0.000 title description 14
- 235000019198 oils Nutrition 0.000 description 106
- XEKOWRVHYACXOJ-UHFFFAOYSA-N acetic acid ethyl ester Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 54
- 239000002904 solvent Substances 0.000 description 40
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 38
- 239000000203 mixture Substances 0.000 description 26
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 24
- 239000000470 constituent Substances 0.000 description 16
- 238000000605 extraction Methods 0.000 description 10
- 239000003960 organic solvent Substances 0.000 description 10
- 241001125046 Sardina pilchardus Species 0.000 description 8
- 125000005456 glyceride group Chemical group 0.000 description 8
- LJQKCYFTNDAAPC-UHFFFAOYSA-N ethanol;ethyl acetate Chemical compound CCO.CCOC(C)=O LJQKCYFTNDAAPC-UHFFFAOYSA-N 0.000 description 6
- 239000010685 fatty oil Substances 0.000 description 6
- 235000019512 sardine Nutrition 0.000 description 6
- 238000000926 separation method Methods 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-M acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 4
- 150000001298 alcohols Chemical class 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 239000011877 solvent mixture Substances 0.000 description 4
- 235000015112 vegetable and seed oil Nutrition 0.000 description 4
- 239000008158 vegetable oil Substances 0.000 description 4
- 235000013311 vegetables Nutrition 0.000 description 4
- 241000273930 Brevoortia tyrannus Species 0.000 description 2
- 229940013317 Fish Oils Drugs 0.000 description 2
- 240000007842 Glycine max Species 0.000 description 2
- 235000010469 Glycine max Nutrition 0.000 description 2
- 240000007049 Juglans regia Species 0.000 description 2
- 235000009496 Juglans regia Nutrition 0.000 description 2
- 240000006240 Linum usitatissimum Species 0.000 description 2
- 235000004431 Linum usitatissimum Nutrition 0.000 description 2
- 240000007817 Olea europaea Species 0.000 description 2
- 235000010678 Paulownia tomentosa Nutrition 0.000 description 2
- 240000002834 Paulownia tomentosa Species 0.000 description 2
- 235000004347 Perilla Nutrition 0.000 description 2
- 240000003877 Perilla frutescens Species 0.000 description 2
- 235000004348 Perilla frutescens Nutrition 0.000 description 2
- 229940057007 Petroleum distillate Drugs 0.000 description 2
- 229940029983 VITAMINS Drugs 0.000 description 2
- 229940021016 Vitamin IV solution additives Drugs 0.000 description 2
- CDXSJGDDABYYJV-UHFFFAOYSA-N acetic acid;ethanol Chemical compound CCO.CC(O)=O CDXSJGDDABYYJV-UHFFFAOYSA-N 0.000 description 2
- 239000003398 denaturant Substances 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 235000021323 fish oil Nutrition 0.000 description 2
- 235000004426 flaxseed Nutrition 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 235000021388 linseed oil Nutrition 0.000 description 2
- 239000000944 linseed oil Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000006011 modification reaction Methods 0.000 description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N n-pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 239000003209 petroleum derivative Substances 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 230000000379 polymerizing Effects 0.000 description 2
- 239000011253 protective coating Substances 0.000 description 2
- 150000003432 sterols Chemical class 0.000 description 2
- 235000003702 sterols Nutrition 0.000 description 2
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 2
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 2
- 239000002966 varnish Substances 0.000 description 2
- 235000013343 vitamin Nutrition 0.000 description 2
- 239000011782 vitamin Substances 0.000 description 2
- 229930003231 vitamins Natural products 0.000 description 2
- 235000020234 walnut Nutrition 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 239000001993 wax Substances 0.000 description 2
Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B3/00—Refining fats or fatty oils
- C11B3/006—Refining fats or fatty oils by extraction
Definitions
- This invention relates to the treatment of fatty oils of the drying and semi-drying types, and it is especially concerned with the separation of the drying portions of such oils from the non-drying portions by means of solvent extraction.
- All naturally occurring fatty oils are mixtures of the glycerides of various higher fatty acids, both saturated and unsaturated, and they are classifi-ed approximately as drying, semi-drying or non-drying according to their ability to become hard and resinous upon exposure to heat or air, due to polymerization or oxidation of the highly unsaturated fatty acid constituents. That is, the more "drying" an oil is, the higher is its percentage of the very unsaturated, or polymerizing,
- oils contain small amounts of sterols, hydrocarbons, waxes, other esters, oil-soluble vitamins and phosphatides.
- the selectionof the particular solvent or extractant for accomplishing such a separation is of paramount importance, as the various organic liquids and combinations thereof which are partly miscible with these oils differ widely in ability to separate the drying from the non-drying components of the oils, and there is, of course, no way of predicting or determining in advance of actual trial the usefulness of any particular organic solvent or combination.
- the selective solvent may be a mixture of a higher alcohol which is a solvent for the unsaturated components, such as amyl alcohol, and a non-solvent for the unsaturated oil component.
- Oils which have had their non-drying components extracted by means of the various solvents disclosed in the above patents generally form more or less brittle films on drying. This is particularly true of acetone extracted oils. Although the brittleness can be reduced by retaining part of the non-drying components in the treated oil, the fast drying properties of the oil are also reduced, and in some cases the oil will not dry to a tack free film in a reasonable length of time.
- the invention provides a new selective solvent which is capable of producing fastdrying oils of a given viscosity in greater yield than has been obtained heretofore, and the selective characteristics of the solvent may be adjusted at will, within certain limits.
- the new selective solvent on which the process of this invention depends is a mixture of ethanol and ethyl acetate. Neither of these two liquids can be used alone because the ethanol will not appreciably dissolve any of the oil and the ethyl acetate is too powerful a solvent. In practice it has been found desirable to limit the proportions ofethanol and ethyl acetate in order to maintain an elficient extraction process, and ordinarily the proportion should be Within the limits of about 3 to 5 volumes of ethanol to 1 volume of of ethyl acetate.
- the solvent mixture be anhydrous or substantially so, as the presence of Water in even the small amount encountered in the ethanol-water azeotropic mixture (where the solvent contains substantial quantities of ethanol) is sufficient to preventthe separation desired.
- Example 1 A sardine oil was heat bodied according to standard pactice until its viscosity had increased to 14.7 poises at 25 C. Samples of the bodied oil were extracted with difierent proportions of The ethanol used was denatured with 5% ethyl acetate, 5% methanol and 1% petroleum-distil late, by volume. The denaturants caused a slight modification in the properties of the solvent mix ture over those obtained when using pure ethar nol. The yields and viscosities of the treated oils are given in the following table in which the figure in the solvent column refers to the volume of solvent used for each volume of unextracted oil:
- Example 2 A similar test was made using linseed oil heat bodied in accordance with standard practice to a viscosity of 19.1 poises at 25 C. The results are as follows:
- the degree to which the raw oil should be bodied, or the highly unsaturated components polymerized depends on the particular characteristics desired in the treated oil, it is necessary that the raw oil be polymerized to some extent, in order for the selective extraction to take place.
- a continuous extraction process may be employed, using countercurrent flow and continuous removal of solvent from the drying and non-drying oil fractions by distillation and return of the solvent in contact with fresh oil.
- any of the vegetable oils, such as linseed, tung, soya, perilla, walnut and the like, and marine oils, such as sardine, menhaden, pilchard and similar fish oils, which contain polymerizable constituents may be treated in the manner described to yield oil fractions of superior drying properties.
- Method for treating heat bodied polymerized vegetable and marine drying oils to obtain oil fractions therefrom of increased drying properties which comprises, mixing such oil with a substantially anhydrous organic solvent consisting essentially of about 3 to 5 volumes of ethan01 to 1 volume of ethyl acetate, permitting the mixture of solvent and oil to separate into two layers, each layer containing an oily constituent, separating the two layers and removing the contained solvent from the layer containing a predominance of the polymerized constituents having increased drying properties- 2.
- Method of treating heat bodied polymerized vegetable and marine drying oils to obtain an oil fraction therefrom of increased drying properties which comprises, mixing such oil with a substantially anhydrous organic solvent consisting essentially of a mixture of about four volumes of ethanol and about one volume of ethyl acetate, permitting the mixture of oil and solvent to separate into two layers and recovering the oil fraction from the layer containing a predominance of the polymerized constituents having increased drying properties.
- Method for treating heat bodied polymerized drying oils containing drying and non-drying constituents which comprises removing from said oils at least a portion of said non-drying constituents by bringing said oil into intimate contact with a substantially anhydrous organic solvent consisting essentially of about 3 to 5 volumes of ethanol to 1 volume of ethyl acetate.
Description
Patented July 9, 1946 SOLVENT EXTRACTION OF DRYDIG OILS Olive Sue Ransom, New York, and Milton Zucker, New Rochelle, N. Y., assignors to Interchemical Corporation, New York, N. Y., a corporationof Ohio No Drawing. Application May 15, 1942, Serial No. 443,080
3 Claims. (Cl. 260-4285) This invention relates to the treatment of fatty oils of the drying and semi-drying types, and it is especially concerned with the separation of the drying portions of such oils from the non-drying portions by means of solvent extraction.
All naturally occurring fatty oils are mixtures of the glycerides of various higher fatty acids, both saturated and unsaturated, and they are classifi-ed approximately as drying, semi-drying or non-drying according to their ability to become hard and resinous upon exposure to heat or air, due to polymerization or oxidation of the highly unsaturated fatty acid constituents. That is, the more "drying" an oil is, the higher is its percentage of the very unsaturated, or polymerizing,
constituents, and the more valuable the oil may be for use in making varnishes and other protective coating materials. In addition these oils contain small amounts of sterols, hydrocarbons, waxes, other esters, oil-soluble vitamins and phosphatides.
It'has been proposed to separate these oils into two or more components, one rich in the highly unsaturated glycerides and the other rich in the saturated glycerides, by means of selective solvent extraction, inasmuch as the highly unsaturated glycerides, if at least partly polymerized, are essentially insoluble in certain organic solvents. The highly unsaturated components of the oil may be partly polymerized by heating the oil until its viscosity increases (known as bodying the oil). As is well known, the selectionof the particular solvent or extractant for accomplishing such a separation is of paramount importance, as the various organic liquids and combinations thereof which are partly miscible with these oils differ widely in ability to separate the drying from the non-drying components of the oils, and there is, of course, no way of predicting or determining in advance of actual trial the usefulness of any particular organic solvent or combination. In the Behr U. S. Patents Nos. 2,166,103, issued July 18, 1939, and 2,239,692, issued April 29, 1941, there is disclosed a method for the selective solvent extraction of these oils employing, as the solvent, various ketones and higher alcohols, especially acetone, and according to the Eibner U. S. Patent No. 1,934,297 the selective solvent may be a mixture of a higher alcohol which is a solvent for the unsaturated components, such as amyl alcohol, and a non-solvent for the unsaturated oil component.
Oils which have had their non-drying components extracted by means of the various solvents disclosed in the above patents generally form more or less brittle films on drying. This is particularly true of acetone extracted oils. Although the brittleness can be reduced by retaining part of the non-drying components in the treated oil, the fast drying properties of the oil are also reduced, and in some cases the oil will not dry to a tack free film in a reasonable length of time.
This invention provides a=method for the selective solvent extraction of naturally occurring fatty oils wherein the drying components are concentrated and separated from the non-drying components to produce fast drying oils which dry to tack free films which are not as brittle as those made from drying oils treated with conventional solvents. Similarly, the invention provides a new selective solvent which is capable of producing fastdrying oils of a given viscosity in greater yield than has been obtained heretofore, and the selective characteristics of the solvent may be adjusted at will, within certain limits.
The new selective solvent on which the process of this invention depends is a mixture of ethanol and ethyl acetate. Neither of these two liquids can be used alone because the ethanol will not appreciably dissolve any of the oil and the ethyl acetate is too powerful a solvent. In practice it has been found desirable to limit the proportions ofethanol and ethyl acetate in order to maintain an elficient extraction process, and ordinarily the proportion should be Within the limits of about 3 to 5 volumes of ethanol to 1 volume of of ethyl acetate.
However, the proportion of ethanol to ethyl acetate which gives the most efficient extraction depends partly on the type of oil being processed and partly on the degree to which the oil has been bodied or polymerized (as may be indicated by viscosity).
It is essentialthat the solvent mixture be anhydrous or substantially so, as the presence of Water in even the small amount encountered in the ethanol-water azeotropic mixture (where the solvent contains substantial quantities of ethanol) is sufficient to preventthe separation desired.
In order that the invention may be more clearly understood, the following examples of fish oil and vegetable oil extractions are given by way of illustration Example 1 A sardine oil was heat bodied according to standard pactice until its viscosity had increased to 14.7 poises at 25 C. Samples of the bodied oil were extracted with difierent proportions of The ethanol used was denatured with 5% ethyl acetate, 5% methanol and 1% petroleum-distil late, by volume. The denaturants caused a slight modification in the properties of the solvent mix ture over those obtained when using pure ethar nol. The yields and viscosities of the treated oils are given in the following table in which the figure in the solvent column refers to the volume of solvent used for each volume of unextracted oil:
Yield 4 ethanol: (volume Viscosity Acetone 1 ethyl per cent of (in poises.
acetate original at 25 0.) oil) Although the acetone produced an extracted.
oil of greater viscosity than did an equal volume of the ethanol-ethyl acetate mixture, the yield was less and the products formed more brittle,
films on drying.
' Example 2 A similar test was made using linseed oil heat bodied in accordance with standard practice to a viscosity of 19.1 poises at 25 C. The results are as follows:
Yield 4 ethanol (volume Yiscosity Acetone 1 ethyl per cent of (in poises acetate original at 25 0.) oil) Like the test on the sardine oil, the oil extracted. with acetone was of greater viscosity than that extracted with a similar volume of the ethanol-ethyl acetate mixture, the yield was less and it formed more brittle films on drying.
Although the degree to which the raw oil should be bodied, or the highly unsaturated components polymerized, depends on the particular characteristics desired in the treated oil, it is necessary that the raw oil be polymerized to some extent, in order for the selective extraction to take place. I
Mixtures of. other alcohols and esters have been tested for use as selective solvents, but none has been discovered which has the universal ability to produce good yields of fast drying oils which form comparatively non-brittle films, as
compared to the ethanol-ethyl acetate mixture.
Instead of batch solvent extraction, as indicated in the examples, a continuous extraction process may be employed, using countercurrent flow and continuous removal of solvent from the drying and non-drying oil fractions by distillation and return of the solvent in contact with fresh oil. Also, any of the vegetable oils, such as linseed, tung, soya, perilla, walnut and the like, and marine oils, such as sardine, menhaden, pilchard and similar fish oils, which contain polymerizable constituents may be treated in the manner described to yield oil fractions of superior drying properties.
We claim:
1. Method for treating heat bodied polymerized vegetable and marine drying oils to obtain oil fractions therefrom of increased drying properties which comprises, mixing such oil with a substantially anhydrous organic solvent consisting essentially of about 3 to 5 volumes of ethan01 to 1 volume of ethyl acetate, permitting the mixture of solvent and oil to separate into two layers, each layer containing an oily constituent, separating the two layers and removing the contained solvent from the layer containing a predominance of the polymerized constituents having increased drying properties- 2. Method of treating heat bodied polymerized vegetable and marine drying oils to obtain an oil fraction therefrom of increased drying properties which comprises, mixing such oil with a substantially anhydrous organic solvent consisting essentially of a mixture of about four volumes of ethanol and about one volume of ethyl acetate, permitting the mixture of oil and solvent to separate into two layers and recovering the oil fraction from the layer containing a predominance of the polymerized constituents having increased drying properties.
3. Method for treating heat bodied polymerized drying oils containing drying and non-drying constituents which comprises removing from said oils at least a portion of said non-drying constituents by bringing said oil into intimate contact with a substantially anhydrous organic solvent consisting essentially of about 3 to 5 volumes of ethanol to 1 volume of ethyl acetate.
OLIVE son RANSOM. MILTON ZUCKER.
Publications (1)
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US2403458A true US2403458A (en) | 1946-07-09 |
Family
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US2403458D Expired - Lifetime US2403458A (en) | Solvent extraction of drying oils |
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Cited By (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2459342A (en) * | 1949-01-18 | Comminuted drying oil residues | ||
US2631270A (en) * | 1947-05-19 | 1953-03-10 | Eastman Oil Well Survey Co | Method of and apparatus for the measurement of distance or time interval by the use of compressional waves in the so-called supersonic range |
US20060078586A1 (en) * | 2004-09-28 | 2006-04-13 | Atrium Medical Corporation | Barrier layer |
US20080113001A1 (en) * | 2006-11-06 | 2008-05-15 | Atrium Medical Corporation | Tissue separating device with reinforced support for anchoring mechanisms |
US20080206305A1 (en) * | 2004-09-28 | 2008-08-28 | Atrium Medical Corporation | Implantable barrier device |
US9278161B2 (en) | 2005-09-28 | 2016-03-08 | Atrium Medical Corporation | Tissue-separating fatty acid adhesion barrier |
US9427423B2 (en) | 2009-03-10 | 2016-08-30 | Atrium Medical Corporation | Fatty-acid based particles |
US9492596B2 (en) | 2006-11-06 | 2016-11-15 | Atrium Medical Corporation | Barrier layer with underlying medical device and one or more reinforcing support structures |
US9682175B2 (en) | 2004-09-28 | 2017-06-20 | Atrium Medical Corporation | Coating material and medical device system including same |
US9867880B2 (en) | 2012-06-13 | 2018-01-16 | Atrium Medical Corporation | Cured oil-hydrogel biomaterial compositions for controlled drug delivery |
US10322213B2 (en) | 2010-07-16 | 2019-06-18 | Atrium Medical Corporation | Compositions and methods for altering the rate of hydrolysis of cured oil-based materials |
US10772995B2 (en) | 2004-09-28 | 2020-09-15 | Atrium Medical Corporation | Cross-linked fatty acid-based biomaterials |
US10814043B2 (en) | 2004-09-28 | 2020-10-27 | Atrium Medical Corporation | Cross-linked fatty acid-based biomaterials |
US10864304B2 (en) | 2009-08-11 | 2020-12-15 | Atrium Medical Corporation | Anti-infective antimicrobial-containing biomaterials |
-
0
- US US2403458D patent/US2403458A/en not_active Expired - Lifetime
Cited By (26)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2459342A (en) * | 1949-01-18 | Comminuted drying oil residues | ||
US2631270A (en) * | 1947-05-19 | 1953-03-10 | Eastman Oil Well Survey Co | Method of and apparatus for the measurement of distance or time interval by the use of compressional waves in the so-called supersonic range |
US11793912B2 (en) | 2004-09-28 | 2023-10-24 | Atrium Medical Corporation | Cross-linked fatty acid-based biomaterials |
US9682175B2 (en) | 2004-09-28 | 2017-06-20 | Atrium Medical Corporation | Coating material and medical device system including same |
US20080206305A1 (en) * | 2004-09-28 | 2008-08-28 | Atrium Medical Corporation | Implantable barrier device |
US10792312B2 (en) * | 2004-09-28 | 2020-10-06 | Atrium Medical Corporation | Barrier layer |
US20060078586A1 (en) * | 2004-09-28 | 2006-04-13 | Atrium Medical Corporation | Barrier layer |
US10772995B2 (en) | 2004-09-28 | 2020-09-15 | Atrium Medical Corporation | Cross-linked fatty acid-based biomaterials |
US10869902B2 (en) | 2004-09-28 | 2020-12-22 | Atrium Medical Corporation | Cured gel and method of making |
US10016465B2 (en) | 2004-09-28 | 2018-07-10 | Atrium Medical Corporation | Cured gel and method of making |
US9801913B2 (en) * | 2004-09-28 | 2017-10-31 | Atrium Medical Corporation | Barrier layer |
US9801982B2 (en) * | 2004-09-28 | 2017-10-31 | Atrium Medical Corporation | Implantable barrier device |
US10814043B2 (en) | 2004-09-28 | 2020-10-27 | Atrium Medical Corporation | Cross-linked fatty acid-based biomaterials |
US11083823B2 (en) | 2005-09-28 | 2021-08-10 | Atrium Medical Corporation | Tissue-separating fatty acid adhesion barrier |
US9278161B2 (en) | 2005-09-28 | 2016-03-08 | Atrium Medical Corporation | Tissue-separating fatty acid adhesion barrier |
US20080113001A1 (en) * | 2006-11-06 | 2008-05-15 | Atrium Medical Corporation | Tissue separating device with reinforced support for anchoring mechanisms |
US9592324B2 (en) * | 2006-11-06 | 2017-03-14 | Atrium Medical Corporation | Tissue separating device with reinforced support for anchoring mechanisms |
US9492596B2 (en) | 2006-11-06 | 2016-11-15 | Atrium Medical Corporation | Barrier layer with underlying medical device and one or more reinforcing support structures |
US9427423B2 (en) | 2009-03-10 | 2016-08-30 | Atrium Medical Corporation | Fatty-acid based particles |
US10285964B2 (en) | 2009-03-10 | 2019-05-14 | Atrium Medical Corporation | Fatty-acid based particles |
US11166929B2 (en) | 2009-03-10 | 2021-11-09 | Atrium Medical Corporation | Fatty-acid based particles |
US10864304B2 (en) | 2009-08-11 | 2020-12-15 | Atrium Medical Corporation | Anti-infective antimicrobial-containing biomaterials |
US10322213B2 (en) | 2010-07-16 | 2019-06-18 | Atrium Medical Corporation | Compositions and methods for altering the rate of hydrolysis of cured oil-based materials |
US11097035B2 (en) | 2010-07-16 | 2021-08-24 | Atrium Medical Corporation | Compositions and methods for altering the rate of hydrolysis of cured oil-based materials |
US10888617B2 (en) | 2012-06-13 | 2021-01-12 | Atrium Medical Corporation | Cured oil-hydrogel biomaterial compositions for controlled drug delivery |
US9867880B2 (en) | 2012-06-13 | 2018-01-16 | Atrium Medical Corporation | Cured oil-hydrogel biomaterial compositions for controlled drug delivery |
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