USH2276H1 - Branched amide polymeric superabsorbents - Google Patents
Branched amide polymeric superabsorbents Download PDFInfo
- Publication number
- USH2276H1 USH2276H1 US13/385,467 US201213385467A USH2276H US H2276 H1 USH2276 H1 US H2276H1 US 201213385467 A US201213385467 A US 201213385467A US H2276 H USH2276 H US H2276H
- Authority
- US
- United States
- Prior art keywords
- polymeric material
- superabsorbent polymeric
- material according
- organic liquids
- superabsorbent
- 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.)
- Abandoned
Links
- 150000001408 amides Chemical class 0.000 title claims abstract description 13
- 239000000463 material Substances 0.000 claims abstract description 34
- 239000007788 liquid Substances 0.000 claims abstract description 28
- 229920000642 polymer Polymers 0.000 claims abstract description 23
- 238000010521 absorption reaction Methods 0.000 claims abstract description 17
- 239000002904 solvent Substances 0.000 claims description 15
- 239000000203 mixture Substances 0.000 claims description 6
- 239000012454 non-polar solvent Substances 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 239000000835 fiber Substances 0.000 claims description 3
- 239000002245 particle Substances 0.000 claims description 3
- 239000002798 polar solvent Substances 0.000 claims description 3
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 2
- 239000000499 gel Substances 0.000 claims description 2
- 229930195733 hydrocarbon Natural products 0.000 claims description 2
- 125000002723 alicyclic group Chemical group 0.000 claims 1
- 125000001931 aliphatic group Chemical group 0.000 claims 1
- 150000002430 hydrocarbons Chemical class 0.000 claims 1
- 239000002250 absorbent Substances 0.000 description 8
- 230000002745 absorbent Effects 0.000 description 8
- 239000000178 monomer Substances 0.000 description 8
- 239000000126 substance Substances 0.000 description 5
- 229920000247 superabsorbent polymer Polymers 0.000 description 5
- 239000004583 superabsorbent polymers (SAPs) Substances 0.000 description 5
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000003463 adsorbent Substances 0.000 description 3
- 125000005250 alkyl acrylate group Chemical group 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- 238000004132 cross linking Methods 0.000 description 3
- 230000003993 interaction Effects 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000003999 initiator Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 239000002594 sorbent Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- -1 alicyclic hydrocarbons Chemical class 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 229920005605 branched copolymer Polymers 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000002894 chemical waste Substances 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 231100001261 hazardous Toxicity 0.000 description 1
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 229920000587 hyperbranched polymer Polymers 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 230000000116 mitigating effect Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/52—Amides or imides
- C08F220/54—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide
- C08F220/58—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide containing oxygen in addition to the carbonamido oxygen, e.g. N-methylolacrylamide, N-(meth)acryloylmorpholine
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
- C08F222/36—Amides or imides
- C08F222/38—Amides
- C08F222/385—Monomers containing two or more (meth)acrylamide groups, e.g. N,N'-methylenebisacrylamide
Definitions
- Embodiments of this disclosure relate to superabsorbents, also known as superabsorbent polymers or SAP, for the absorption of a broad spectrum of organic liquids at low percentages of absorber (5% or less).
- SAP superabsorbent polymers
- the disclosure describes branched amide polymeric superabsorbents for the mitigation of hazardous organic solvents in the environment.
- sorbents may require 10% (w/w) or more of material to immobilize organic liquids. They may also have a limited range of liquids for which they are highly effective. Generally, sorbents fall into two classes, i.e., adsorbents and absorbents. Adsorbents immobilize liquids through interaction of the liquid with the surface of the material and therefore have a capacity that can be limited by the material's surface area. Absorbents may also take liquid into the internal molecular structure of the material, resulting in much higher capacity relative to adsorbents.
- the balance of the interstitial solvent-material interactions and the absorption induced strain in the material determines the capacity of an absorbent material for a given solvent.
- the degree of swelling of a polymeric absorbent is solvent dependent, and depends on the chemical structure of the polymer backbone in addition to other factors.
- the polymers of the present disclosure have been developed as highly absorbent polymeric materials that can be manufactured at low cost, and cover a broader range of solvents.
- the superabsorbent polymeric material for absorption of organic liquids is at least one crosslinked branched amide polymer.
- a composition includes the superabsorbent polymeric material, which may be in the form of a film, a layer, a sheet, a pad, a gel, particles, or fibers.
- Other embodiments of the superabsorbent polymeric material and co-polymers for structural functionality are provided in the detailed description as provided.
- FIG. 1 is a first chemical structural view of cross-linked branched amide polymers with a high absorption capacity for organic liquids
- FIG. 2 is a second chemical structural view of cross-linked branched amide polymers with a high absorption capacity for organic liquids
- polymer is used to refer to a chemical compound that comprises linked monomers, and that may or may not be linear, crosslinked or thermosetting.
- monomer is used generically, unless otherwise indicated, to mean monomers, comonomers, termonomers, and tetramonomers.
- Branched polymers are understood to include hyperbranched polymers (containing two or more generations of branching), which are obtained via a polymerization reaction.
- the branched polymers of the present disclosure are crosslinked and may include statistical, gradient and alternating branched copolymers.
- organic solvents and “organic liquids” are interchangeable and understood to include a chemical class of compounds that are used routinely in commercial industries. They share a common structure (at least one carbon atom and one hydrogen atom), low molecular weight, volatility, and they exist in liquid form at room temperature. They may be grouped further into aliphatic-chain compounds, and as aromatic compounds.
- this disclosure provides a new class of superabsorbent polymers for use with non-aqueous organic liquids and solvents. These superabsorbent polymers have a high absorption capacity for both polar solvents and nonpolar solvents.
- the superabsorbent polymers of the present disclosure are capable of absorbing and retaining quantities of organic liquids equivalent to many times their own weight.
- the superabsorbents are crosslinked branched amide polymers, in which with each succeeding generation an additional branch point is introduced into the polymer's side chains. The additional branch point provides sites for solvent interaction with the backbone and a larger degree of sterically induced extension of the polymer backbone as solvent enters the interstitial sites along the polymer backbone.
- these polymeric materials absorb a broad spectrum of organic liquids with high efficiency, and have absorption capacities as high as 500 times their dry weight. These polymeric materials may also be relatively inexpensive to manufacture, as they can be prepared from readily available starting materials.
- FIGS. 1 through 3 show the general structure of the superabsorbent polymers.
- the illustrated general structure shows the mechanism and components for formulating the crosslinked branched amide polymers of the disclosure, which have a high absorption capacity for organic liquids.
- the R substitutents as shown in each first and second generation, are branched and substituted or unsubsitituted, in three case scenarios.
- any of the R substituents represents or contains an alkyl substituent group, these may be linear or branched and may contain up to 40, preferably up to six carbon atoms.
- An aryl group or moiety may contain from one to 40 carbon atoms.
- Crosslinking may be affected during polymerization by incorporation of suitable crosslinking monomers.
- the polymers can be crosslinked after polymerization by reaction with a suitable reactive crosslinking agent. Reaction temperature, pH, amount of added initiator, concentration, and reaction time may control the extent of crosslinking and molecular weight increase after addition of the initiator.
- the superabsorbent polymeric materials may be in the form of a film, a layer, a sheet, a pad, a gel, particles (granules), and fibers, and may be combined in compositions with other materials for higher absorption capacity and long-term effectiveness.
Abstract
A superabsorbent polymeric material for absorption of organic liquids which includes at least one cross-linked branched amide polymer for absorbing and retaining quantities of organic liquids equivalent to several times its dry weight.
Description
The invention described was made in the performance of official duties by one or more employees of the Department of the Navy, and thus, the invention herein may be manufactured, used or licensed by or for the Government of the United States of America for governmental purposes without the payment of any royalties thereon or therefor.
1. Technical Field
Embodiments of this disclosure relate to superabsorbents, also known as superabsorbent polymers or SAP, for the absorption of a broad spectrum of organic liquids at low percentages of absorber (5% or less). Specifically, the disclosure describes branched amide polymeric superabsorbents for the mitigation of hazardous organic solvents in the environment.
2. Discussion of the Prior Art
Current commercially available sorbents may require 10% (w/w) or more of material to immobilize organic liquids. They may also have a limited range of liquids for which they are highly effective. Generally, sorbents fall into two classes, i.e., adsorbents and absorbents. Adsorbents immobilize liquids through interaction of the liquid with the surface of the material and therefore have a capacity that can be limited by the material's surface area. Absorbents may also take liquid into the internal molecular structure of the material, resulting in much higher capacity relative to adsorbents.
The balance of the interstitial solvent-material interactions and the absorption induced strain in the material determines the capacity of an absorbent material for a given solvent. The degree of swelling of a polymeric absorbent is solvent dependent, and depends on the chemical structure of the polymer backbone in addition to other factors.
Very few highly absorbent polymers for organic liquids and solvents have been identified in the literature; nearly all of them are based on alkyl acrylates. The alkyl acrylates strongly absorb some non-polar solvents but are unsuitable for solvents of higher polarity. A copolymer of alkyl acrylates with a hydrophobic trialkylammonium salt showed inverse behavior with a high absorption capacity for polar solvents and a low absorption capacity for nonpolar solvents. While the absorption capacity of the copolymer may be impressive (over one-hundred times its weight for some solvents), the material suffers from a very high projected manufacturing cost. None of the known absorbents have high absorption capacities over a broad range of solvent polarities and types, i.e., alkyl, aromatic, non-polar, polar aprotic, polar protic, etc.
Accordingly, the polymers of the present disclosure have been developed as highly absorbent polymeric materials that can be manufactured at low cost, and cover a broader range of solvents.
In accordance with an embodiment of the disclosure, the superabsorbent polymeric material for absorption of organic liquids is at least one crosslinked branched amide polymer. In another embodiment of the disclosure, a composition includes the superabsorbent polymeric material, which may be in the form of a film, a layer, a sheet, a pad, a gel, particles, or fibers. Other embodiments of the superabsorbent polymeric material and co-polymers for structural functionality are provided in the detailed description as provided.
These and various other features and aspects of various exemplary embodiments will be readily understood with reference to the following detailed description taken in conjunction with the accompanying drawings, in which like or similar numbers are used throughout, and in which:
A more complete appreciation of the disclosure and many of the attendant advantages will be readily obtained, as the same becomes better understood by reference to the following detailed description when considered in connection with the accompanying drawing. In describing and claiming the present invention, the following terminology will be used in accordance with the definitions set out below.
The term “polymer” is used to refer to a chemical compound that comprises linked monomers, and that may or may not be linear, crosslinked or thermosetting. The term “monomer” is used generically, unless otherwise indicated, to mean monomers, comonomers, termonomers, and tetramonomers. “Branched” polymers are understood to include hyperbranched polymers (containing two or more generations of branching), which are obtained via a polymerization reaction. The branched polymers of the present disclosure are crosslinked and may include statistical, gradient and alternating branched copolymers.
The phrases “organic solvents” and “organic liquids” are interchangeable and understood to include a chemical class of compounds that are used routinely in commercial industries. They share a common structure (at least one carbon atom and one hydrogen atom), low molecular weight, volatility, and they exist in liquid form at room temperature. They may be grouped further into aliphatic-chain compounds, and as aromatic compounds. Examples of the organic solvents include, but are not limited to, alicyclic hydrocarbons such as cyclohexane and cyclopentane, aliphatic hydrocarbons such as n-pentane, n-hexane, n-heptane and ligroin, and aromatic hydrocarbons such as benzene, toluene and xylene.
In an embodiment, this disclosure provides a new class of superabsorbent polymers for use with non-aqueous organic liquids and solvents. These superabsorbent polymers have a high absorption capacity for both polar solvents and nonpolar solvents. The superabsorbent polymers of the present disclosure are capable of absorbing and retaining quantities of organic liquids equivalent to many times their own weight. The superabsorbents are crosslinked branched amide polymers, in which with each succeeding generation an additional branch point is introduced into the polymer's side chains. The additional branch point provides sites for solvent interaction with the backbone and a larger degree of sterically induced extension of the polymer backbone as solvent enters the interstitial sites along the polymer backbone.
In an embodiment, these polymeric materials absorb a broad spectrum of organic liquids with high efficiency, and have absorption capacities as high as 500 times their dry weight. These polymeric materials may also be relatively inexpensive to manufacture, as they can be prepared from readily available starting materials.
In an embodiment, the polymeric material is poly[N,N-di(2-methoxyethyl)acrylamide, which absorbs organic liquids with dielectric constants between two and 40 at 15 times its weight or more. In another embodiment, the superabsorbent polymeric materials of the present disclosure may be prepared by mixing the monomers in desired stoichiometric ratios in solution and then initiating free-radical copolymerization. In addition, branched polymers may be generally prepared via a step-growth mechanism involving the poly-condensation of a mixture of mono-functional and multi-functional monomers. The mono-functional monomers polymer chains and where a multi-functional monomer is introduced into the chain a branch point is formed.
Crosslinking may be affected during polymerization by incorporation of suitable crosslinking monomers. Alternatively, the polymers can be crosslinked after polymerization by reaction with a suitable reactive crosslinking agent. Reaction temperature, pH, amount of added initiator, concentration, and reaction time may control the extent of crosslinking and molecular weight increase after addition of the initiator. In another embodiment, the superabsorbent polymeric materials may be in the form of a film, a layer, a sheet, a pad, a gel, particles (granules), and fibers, and may be combined in compositions with other materials for higher absorption capacity and long-term effectiveness.
In view of the above disclosure, the polymeric materials demonstrate organic liquid absorbent capability that has several commercial applications, including chemical waste treatment, spill clean up, and solvent entrainment. In addition, these polymeric materials may significantly outperform any commercially available material at comparable cost.
Obviously, numerous modifications and variations of the disclosure are possible in light of the above disclosure. It is therefore understood that within the scope of the appended claims, the disclosure may be practiced otherwise than as specifically described herein.
Claims (12)
1. A superabsorbent polymeric material for absorption of organic liquids consisting essentially of at least one crosslinked branched amide polymer.
2. The superabsorbent polymeric material according to claim 1 , wherein the superabsorbent polymeric material absorbs and retains quantities of organic liquids equivalent to several times its dry weight.
3. The superabsorbent polymeric material according to claim 1 , wherein the cross-linked branched amide polymer has an absorption capacity as high as 500 times its dry weight.
4. The superabsorbent polymeric material according to claim 1 , wherein the cross-linked branched amide polymer absorbs organic liquids with dielectric constants between two and 40 at 15 times its weight or more.
5. The superabsorbent polymeric material according to claim 1 , wherein the cross-linked branched amide polymer is poly[N,N-di(2-methoxyethyl)acrylamide].
6. The superabsorbent polymeric material according to claim 1 , wherein the organic liquids consist of polar and non-polar solvents.
7. The superabsorbent polymeric material according to claim 6 , wherein the solvents comprise alicyclic organic liquids.
8. The superabsorbent polymeric material according to claim 6 , wherein the solvents comprise aliphatic organic liquids.
9. The superabsorbent polymeric material according to claim 6 , wherein the solvents comprise aromatic organic liquids.
10. The superabsorbent polymeric material according to claim 6 , wherein the solvents comprise hydrocarbons.
11. A composition comprising the superabsorbent polymeric material according to claim 1 .
12. The composition according to claim 11 , wherein the composition is in the form at least one of a film, a layer, a sheet, a pad, a gel, particles, and fibers.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US13/385,467 USH2276H1 (en) | 2012-01-09 | 2012-01-09 | Branched amide polymeric superabsorbents |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US13/385,467 USH2276H1 (en) | 2012-01-09 | 2012-01-09 | Branched amide polymeric superabsorbents |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| USH2276H1 true USH2276H1 (en) | 2013-06-04 |
Family
ID=48484488
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US13/385,467 Abandoned USH2276H1 (en) | 2012-01-09 | 2012-01-09 | Branched amide polymeric superabsorbents |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | USH2276H1 (en) |
Citations (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2512606A (en) | 1945-09-12 | 1950-06-27 | Du Pont | Polyamides and method for obtaining same |
| US5071902A (en) | 1989-01-25 | 1991-12-10 | Rohm Gmbh | Aqueous synthetic resin dispersions |
| US5093030A (en) * | 1990-04-18 | 1992-03-03 | Agency Of Industrial Science And Technology | Method for production of dispersion containing minute polymer beads possessing thermosensitive characteristic |
| US5567797A (en) | 1992-07-25 | 1996-10-22 | A. Schulman, Inc. | Polyamide composition and process for its production |
| US6277911B1 (en) | 1995-02-01 | 2001-08-21 | Ems Inventa Ag | Transparent, colorless, amorphous copolyamides and molded articles made therefrom |
| US6884865B1 (en) | 2000-08-09 | 2005-04-26 | Rhodia Engineering Plastics S.R.L. | Copolyamides and compositions based on same |
| US6910823B2 (en) | 1998-11-09 | 2005-06-28 | The Procter & Gamble Company | Cleaning composition, pad, wipe, implement, and system and method of use thereof |
| US20060029782A1 (en) | 2002-10-25 | 2006-02-09 | Jorg Harren | Absorbent polymer structure with improved retention capacity and permeability |
| US7182537B2 (en) | 1998-12-01 | 2007-02-27 | The Procter & Gamble Company | Cleaning composition, pad, wipe, implement, and system and method of use thereof |
| US20080255531A1 (en) | 2005-08-05 | 2008-10-16 | Horst Ring | Superabsorbents, Nanofiber Nonwovens Finished Therewith and Use Thereof |
| US20090065436A1 (en) | 2007-03-15 | 2009-03-12 | Kalayci Veli E | super absorbent containing web that can act as a filter, absorbent, reactive layer or fuel fuse |
| US7615270B2 (en) | 2002-11-12 | 2009-11-10 | E. I. Du Pont De Nemours And Company | Films comprising a liquid-absorbant inner layer and an impermeable outer layer |
| US20100285094A1 (en) | 2006-04-20 | 2010-11-11 | University Of Utah Research Foundation | Polymeric compositions and methods of making and using thereof |
-
2012
- 2012-01-09 US US13/385,467 patent/USH2276H1/en not_active Abandoned
Patent Citations (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2512606A (en) | 1945-09-12 | 1950-06-27 | Du Pont | Polyamides and method for obtaining same |
| US5071902A (en) | 1989-01-25 | 1991-12-10 | Rohm Gmbh | Aqueous synthetic resin dispersions |
| US5093030A (en) * | 1990-04-18 | 1992-03-03 | Agency Of Industrial Science And Technology | Method for production of dispersion containing minute polymer beads possessing thermosensitive characteristic |
| US5567797A (en) | 1992-07-25 | 1996-10-22 | A. Schulman, Inc. | Polyamide composition and process for its production |
| US6277911B1 (en) | 1995-02-01 | 2001-08-21 | Ems Inventa Ag | Transparent, colorless, amorphous copolyamides and molded articles made therefrom |
| US6910823B2 (en) | 1998-11-09 | 2005-06-28 | The Procter & Gamble Company | Cleaning composition, pad, wipe, implement, and system and method of use thereof |
| US7182537B2 (en) | 1998-12-01 | 2007-02-27 | The Procter & Gamble Company | Cleaning composition, pad, wipe, implement, and system and method of use thereof |
| US6884865B1 (en) | 2000-08-09 | 2005-04-26 | Rhodia Engineering Plastics S.R.L. | Copolyamides and compositions based on same |
| US20060029782A1 (en) | 2002-10-25 | 2006-02-09 | Jorg Harren | Absorbent polymer structure with improved retention capacity and permeability |
| US7833624B2 (en) | 2002-10-25 | 2010-11-16 | Evonik Stockhuasen GmbH | Absorbent polymer structure with improved retention capacity and permeability |
| US7615270B2 (en) | 2002-11-12 | 2009-11-10 | E. I. Du Pont De Nemours And Company | Films comprising a liquid-absorbant inner layer and an impermeable outer layer |
| US20080255531A1 (en) | 2005-08-05 | 2008-10-16 | Horst Ring | Superabsorbents, Nanofiber Nonwovens Finished Therewith and Use Thereof |
| US20100285094A1 (en) | 2006-04-20 | 2010-11-11 | University Of Utah Research Foundation | Polymeric compositions and methods of making and using thereof |
| US20090065436A1 (en) | 2007-03-15 | 2009-03-12 | Kalayci Veli E | super absorbent containing web that can act as a filter, absorbent, reactive layer or fuel fuse |
| US7988860B2 (en) | 2007-03-15 | 2011-08-02 | Donaldson Company Inc. | Superabsorbent-containing web that can act as a filter, absorbent, reactive layer or fuel fuse |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| AS | Assignment |
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