WO1998040434A1 - Degradable composite polymer and method of making such composite polymer - Google Patents
Degradable composite polymer and method of making such composite polymer Download PDFInfo
- Publication number
- WO1998040434A1 WO1998040434A1 PCT/US1998/005281 US9805281W WO9840434A1 WO 1998040434 A1 WO1998040434 A1 WO 1998040434A1 US 9805281 W US9805281 W US 9805281W WO 9840434 A1 WO9840434 A1 WO 9840434A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- polymer
- weight
- resin
- comprised
- approximately
- Prior art date
Links
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B24—GRINDING; POLISHING
- B24C—ABRASIVE OR RELATED BLASTING WITH PARTICULATE MATERIAL
- B24C11/00—Selection of abrasive materials or additives for abrasive blasts
- B24C11/005—Selection of abrasive materials or additives for abrasive blasts of additives, e.g. anti-corrosive or disinfecting agents in solid, liquid or gaseous form
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B24—GRINDING; POLISHING
- B24C—ABRASIVE OR RELATED BLASTING WITH PARTICULATE MATERIAL
- B24C11/00—Selection of abrasive materials or additives for abrasive blasts
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L3/00—Compositions of starch, amylose or amylopectin or of their derivatives or degradation products
- C08L3/02—Starch; Degradation products thereof, e.g. dextrin
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L67/00—Compositions of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Compositions of derivatives of such polymers
- C08L67/04—Polyesters derived from hydroxycarboxylic acids, e.g. lactones
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L23/00—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers
- C08L23/02—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers not modified by chemical after-treatment
- C08L23/04—Homopolymers or copolymers of ethene
- C08L23/08—Copolymers of ethene
Definitions
- the present invention relates to composite polymers and methods for
- present invention are degradable. Still further, the present invention includes applications
- Plastic materials are any synthetic materials comprised of polymers which
- printable plastic materials are plastic materials which are able
- plasticizer incorporated into their formula which creates a residue on the surface of the
- Polylactic acid resin a degradable material, offers a quality printing
- polylactic acid is extremely hard, it is very abrasive on cutting tools.
- polylactic acid is a brittle material, it fractures, especially at
- starch and a plasticizer, are very soft and rubbery, and ink cannot be printed on such
- powder coatings include dipping the substrate material to be stripped into a pot of molten
- Another method involves putting
- the substrate material in a high temperature oven, approximately 600-900° F, to turn the
- Still another method involves using small glass beads in an abrasive process
- beads provide an unsatisfactory result by causing surface stress and possibly also changing the texture of the substrate. Thus, many coated materials must be scrapped
- Plastic media blast material is an effective way to surface clean various media blast material.
- polymer are needed for a variety of applications including those in which enhanced
- a further object of this invention is to provide degradable composite
- composite polymer and a method for producing the same wherein the composite polymer is produced in a range of hardnesses so that it can be used as a plastic media blast
- Still another object of this invention is to provide a degradable composite
- Another object of this invention is to provide a degradable composite
- Still another object of this invention is to provide a method for
- Still another object of this invention is to provide a process for producing
- a degradable composite polymer comprised of a polymer comprised of lactic
- This composite polymer is first created by combining the polymer and the
- This degradable composite polymer may be used, among other things, as plastic media blast material or
- novel degradable composite polymers of the present invention are:
- the polymer is comprised of lactic acid monomers
- the resin is comprised of a thermoplastic polymer, destructured starch, and a
- plasticizer If the polymer comprised of lactic acid monomers is a copolymer, in addition
- the other monomers in this polymer should be degradable
- the polymer is polylactic acid (PL A).
- One method of producing PLA includes catalyzing crude lactic acid,
- the polymer comprised of lactic acid monomers has a
- the lactic acid monomers in the polymer may be comprised of between about 0 and 90% D-lactide by weight.
- the lactic acid in the polymer is comprised of about 1% or less D-lactide
- the starch component of the resin may be any starch of natural or plant
- the starch component has
- amylopectin content of more than 70% by weight.
- starch starch, starch acetates, cationic starches, oxidized starches, cross-linked starches and the
- Starch is provided without processing, such as drying, and without the
- structured starch means a starch which
- the plasticizer used in the resin is preferably a polyol, polyol derivative,
- polyol reaction product polyol oxidation product or a mixture thereof.
- polyol oxidation product polyol oxidation product or a mixture thereof.
- plasticizer has a boiling point of at least 150°C. Examples of plasticizers that can be used
- glycerine include, but are not limited to, glycerine, polyglycerol, glycerol, polyethylene glycol, ethylene glycol, propylene glycol, sorbitol, marmitol, and their acetate, ethoxylate, or
- ethylene or propylene diglycol examples include, but are not limited to, ethylene or propylene diglycol, ethylene or propylene
- neopentylglycol trimethylolpropane, pentaerythritol, sorbitol acetate, sorbitol diacetate,
- mannitol monoacetate mannitol monoethoxylate
- butyl glucoside glucose
- thermoplastic polymer in the resin is a synthetic polymeric component
- Preferred polymeric components included in the resin are polyethylene, polyvinyl
- one of the polymers in the resin is an ethylene-acrylic acid
- copolymer with ethlylene contents of from about 10 to 44% by weight.
- the resin also may contain relatively low amounts, approximately 5% or less by weight of the overall
- composition of hydrophobic polymers, such as polyethylene, polypropylene and
- polystyrene Still further, other polymers such as polyamide, polyacrylic, polyester, and
- poly ether may be in the resin.
- the polymer and starch may be combined in a 1 : 19 to 19: 1
- the polymer component of the resin has a higher molecular weight
- neutralizing agents may, optionally, be added to the resin but are not essential
- a destructuring agent is added while making the resin.
- destructuring agent may be urea, alkaline and alkaline-earth hydroxides, and mixture
- alkaline and alkaline-earth hydroxides include but are not limited
- urea is added as the
- the amount by weight is preferably 1 to 35%.
- destructuring agent added to the resin is 2-20% of the weight of the starch.
- the resin also may contain cross-linking agents such as aldehydes like
- compositions for molding or extrusion such as fatty acids, esters
- the resin further may contain a neutralizing agent, such as ammonia or
- acidic polymer such as ethylene-acrylic acid copolymer is used.
- Ammonia may be added
- ammonia should be removed before or during extrusion.
- boron derivatives may be used in the resin.
- boron content is between about 0.002 and 0.4% and preferably between
- stabilizers such as, carbon black, may be added to improve the resistance of the articles
- inorganic salts of alkali or alkaline-earth metals particularly lithium chloride and sodium
- starch-based molding compositions such as fungicides, herbicides, antioxidants, fertilizers, opacifiers, stabilizers and plasticizers. All these additives may be used in
- the resin is made by mixing the essential components, namely, the starch,
- thermoplastic polymer plasticizer and thermoplastic polymer, and any other optionally included components, in
- a conventional device such as a heated extruder, which ensures conditions of temperature
- the starch's structure is interpenetrated or at least partially
- thermoplastic polymer interpenetrated by the thermoplastic polymer so as to obtain a thermoplastic melt.
- starch may be destructured before it is combined with the polymer, or as it is combined.
- a destructuring agent may be mixed with the starch and the plasticizer in a heated
- the mixture is extruded to form the resin at a
- the resin Preferably, according to one formulation of the present invention, the resin
- a film-grade material comprised of about 10-90% by weight polymer or copolymer
- destructuring agent 0-20% by weight destructuring agent, and about 0-6% by weight water. More preferably,
- the resin is comprised of about 20-70% by weight destructured starch, about 10-50% by
- polymer or copolymer about 2-40% by weight plasticizer, about 0- 10% by weight
- destructuring agent about 1-5% by weight water, and about 0.002-0.4%) by weight boron
- One of the most preferred formulations of the resin is 41% by weight
- composite polymers of this invention is resin sold by Novamont, S.p.A., via G. Fauser,
- the lactic acid polymer which is preferably PLA
- the resin which is
- Mater BiTM may be combined to form the degradable composite polymers of
- polymers of this invention which contain more resin are softer and more flexible.
- the composite may be a lactic acid polymer and the remaining 10-90%) by weight of the composite
- polymer is the resin.
- This degradable composite polymer is made by first combining the
- the polymer and the resin may be combined in a container and then fed into
- the extruder or the polymer and the resin may be combined in the extruder. Any combination thereof
- the extruder may be used.
- the extruder may be used.
- a colorant also may optionally be added to the mixture.
- the particles of resin are preferably, the particles of resin
- the extruder should be sufficiently heated so that the composite polymer
- the extruder should be at higher temperatures to form harder composite
- the temperature chosen for the process should be influenced by
- the composite polymer should be formed at a
- polymer has a relatively higher molecular weight, then, preferably, the composite
- polymer is formed at higher temperatures within the disclosed temperature range.
- the degradable composite polymer forms in the heated extruder after the
- the composite is extruded for about 30-240 seconds.
- the composite is extruded for about 30-240 seconds.
- polymer forms after the polymer and the resin are extruded for about 50-90 seconds.
- the resulting degradable composite polymer is cut with a
- the polymer and the resin are combined in approximately a 1 : 1 ratio by weight
- the degradable composite polymer of the present invention has enhanced
- thermoform a high melting point and the ability to thermoform.
- the degradable composite polymer of the present invention is an
- novel degradable composite polymer of the present invention is useful
- this composite polymer be formed with this composite polymer by injection molding, thermoforming or blowing.
- composition should be any suitable plastic material. If used as a printable plastic material, the composition should be any suitable plastic material. If used as a printable plastic material, the composition should be any suitable plastic material.
- thermoplastic resin comprised of a thermoplastic
- polymer Preferably, for cutting purposes, it is
- This printable plastic material is made by first combining a polymer and
- the extruded mixture can be formed into sheets by any method known to those skilled in the art.
- the composite polymer is
- rollers for example, three vertically-arranged rollers
- the rollers should be cooler than the temperature of the mixture
- water having a temperature of about 10-50°C is pumped
- the stored plastic sheets are subsequently processed. They may be cut
- plastic cards such as phone cards or credit cards.
- the degradable composite is able to act as a substrate and retain the ink.
- polymer of the present invention may be printed with conventional or ultraviolet (UV)
- the polymer and resin are in about a 50/50 combination by weight so that the printing dies are not worn. If printed with
- the ink sets up at ambient temperature when exposed to light. If the
- UV ink material is printed with UV ink, then UV light must be used to cure or dry the ink.
- the UV light is flashed in intervals which last for a
- This degradable composite polymer can be
- the composite polymer which is later
- molded is formed at a temperature of about 160-190°C, if used as a printable plastic
- the degradable composite polymer of the present invention has a
- the mold release time as compared to typical plastics, can be increased
- the injection speed can be varied
- the nozzle pressure is about 1300 to 1400 bar.
- the minimum gate size is about 1 mm full round.
- the mold is made of an acid-resistant material such as an acid-resistant metal.
- cavities is enhanced when the molds are specially designed for a degradable material.
- One preferable design incorporates the use of rounded corners inside the mold, as
- the sprue length should be as
- Molded articles can be colored in numerous ways. The coloring of the
- degradable composite polymer can either be accomplished by compounding the PLA
- polymers of the present invention should be dried before being processed. Also, during
- LDPE low density polyethylene
- polymer of the present invention can be substituted for the LDPE.
- LDPE can be used to cleanse the equipment of the degradable composite polymer.
- a plastic media blast process is a process for the rapid, economic, and safe
- a plastic media blast process is a dry stripping
- plastic granules It is especially useful on surfaces which cannot tolerate damaging
- present invention is particularly useful as plastic media blast material.
- the plastic is particularly useful as plastic media blast material.
- particles are pneumatically applied at pressures of about 10-40 psi.
- Plastic media blast material is made by first combining a polymer and a
- the method involves feeding the extruded mixture, which is a soft, hot, molten resin, into a
- the rod die and forming the composite polymer into a continuous rod.
- the rod is
- pellets are then further reduced in size by grinding so as to form
- plastic media blast material of the present invention may
- plastic media blast material made entirely from lactic acid polymers cannot be made in
- lactic acid polymer must be combined with a resin comprised of a thermoplastic polymer
- the grit size of the plastic media blast particles can be varied. However,
- the degradable composite polymer of the present invention is ground to a very low density polyethylene
- the plastic media blast particles have equivalent
- the plastic media have equivalent diameters of between about 0.4 and 1.2 mm.
- blast material may be created in a variety of hardnesses to remove different substances
- the plastic media blast material of the present invention can be used in any convenient manner.
- polymer coatings and epoxy coatings. It may be used on any surface including flexible
- plastic media blast material can be used include, but are not limited
- the plastic media blast process is environmentally sound and is an
- composite polymer of the present invention as a plastic media blast material avoids the
- plastic particles and high flow rate permits rapid removal without warping panels or
- clad, anodized, galvanized and phosphate coatings may
- paint can be left in tact. And, in many cases, paint can be removed layer by layer down to the base
- composition containing the following components was prepared:
- PLA semicrystalline polylactic acid
- the temperatures employed were 180, 180, 190 and 190°C, respectively.
- the extruded sheets were cooled and cut into 610 mm by 610 mm (24 in
- composition containing the following components was prepared:
- the opening was 3 mm.
- the extruder barrel was divided into 5 zones. The temperatures
- the extrudates were air cooled and then granulated using a C.W.
- composition containing the following components was prepared:
- the extruder barrel was divided into 5 zones. The temperatures employed
- the extrudates were air cooled and then granulated using a C.W.
- a composition containing the following components was prepared: 47.5%o by weight of amorphous polylactic acid (PLA) containing 18% D-lactide by
- the temperatures employed were 152, 149, 160 and 160°C, respectively
- rolls were 48, 60, and 43 °C, respectively for the top, middle and bottom rolls.
- the extruded sheets were cooled and cut into 610 mm by 610 mm (24 in
- composition containing the following components was prepared:
- PLA semicrystalline polylactic acid
- lactide by weight with a molecular weight of 80,000, 27.5% by weight of ZF03U/A class
- rolls were 48, 60 and 43 °C, respectively for the top, middle and bottom rolls.
- the extruded sheets were cooled and cut into 610 mm by 610 mm (24 in
- the degradable composite polymers of the present invention can be used.
- the composite polymer also has the ability to retain
- polymer is able to be cut easily without fracturing so that it may be cut into small plastic
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- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Mechanical Engineering (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Extrusion Moulding Of Plastics Or The Like (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Abstract
Description
Claims
Priority Applications (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
AU65641/98A AU6564198A (en) | 1997-03-14 | 1998-03-13 | Degradable composite polymer and method of making such composite polymer |
EP98911760A EP0966502A4 (en) | 1997-03-14 | 1998-03-13 | Degradable composite polymer and method of making such composite polymer |
CA002285458A CA2285458A1 (en) | 1997-03-14 | 1998-03-13 | Degradable composite polymer and method of making such composite polymer |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US4077997P | 1997-03-14 | 1997-03-14 | |
US60/040,779 | 1997-03-14 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO1998040434A1 true WO1998040434A1 (en) | 1998-09-17 |
Family
ID=21912892
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/US1998/005281 WO1998040434A1 (en) | 1997-03-14 | 1998-03-13 | Degradable composite polymer and method of making such composite polymer |
Country Status (4)
Country | Link |
---|---|
EP (1) | EP0966502A4 (en) |
AU (1) | AU6564198A (en) |
CA (1) | CA2285458A1 (en) |
WO (1) | WO1998040434A1 (en) |
Cited By (16)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2004002773A (en) * | 2002-03-29 | 2004-01-08 | Mitsui Chemicals Inc | Lactic acid type resin composition |
US6709526B1 (en) | 1999-03-08 | 2004-03-23 | The Procter & Gamble Company | Melt processable starch compositions |
US6723160B2 (en) | 2002-02-01 | 2004-04-20 | The Procter & Gamble Company | Non-thermoplastic starch fibers and starch composition for making same |
WO2004080656A1 (en) * | 2003-03-14 | 2004-09-23 | Workinter Limited | Method for selective removal of materials present in one or more layers on an object, and apparatus for implementation of this method |
US6811740B2 (en) | 2000-11-27 | 2004-11-02 | The Procter & Gamble Company | Process for making non-thermoplastic starch fibers |
EP1490435A1 (en) * | 2002-03-29 | 2004-12-29 | Mitsui Chemicals, Inc. | Lactic acid-based resin composition |
DE102008042893A1 (en) | 2008-10-16 | 2010-04-29 | Wacker Chemie Ag | Mixtures for the production of biodegradable moldings based on aliphatic polyesters and water-redispersible polymer powders |
EP2228175A1 (en) * | 2009-03-12 | 2010-09-15 | Ferton Holding SA | Powder for powder streams, powder mixture and use for processing in particular dental surfaces |
US7947766B2 (en) | 2003-06-06 | 2011-05-24 | The Procter & Gamble Company | Crosslinking systems for hydroxyl polymers |
US8623246B2 (en) | 2004-04-29 | 2014-01-07 | The Procter & Gamble Company | Process of making a fibrous structure |
US9017586B2 (en) | 2004-04-29 | 2015-04-28 | The Procter & Gamble Company | Polymeric structures and method for making same |
EP3210723A1 (en) * | 2016-02-25 | 2017-08-30 | Kamei Tekkousho Ltd. | Abrasive materials |
WO2017222824A1 (en) | 2016-06-21 | 2017-12-28 | 3M Innovative Properties Company | Graphic articles comprising semicrystalline polylactic acid based film |
WO2020079902A1 (en) * | 2018-10-17 | 2020-04-23 | 株式会社ダイセル | Treatment granules, compounding unit equipped with treatment granules, and production method for treatment granules |
US11066551B2 (en) | 2016-05-20 | 2021-07-20 | 3M Innovative Properties Company | Oriented polylactic acid polymer based film |
US11254812B2 (en) | 2014-12-22 | 2022-02-22 | 3M Innovative Properties Company | Compositions and films comprising polylactic acid polymer, polyvinyl acetate polymer and plasticizer |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN109611070B (en) * | 2019-01-07 | 2021-01-01 | 中国石油天然气股份有限公司 | Gel breaking degradation method for polyacrylamide polymer fracturing fluid |
Citations (2)
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---|---|---|---|---|
US5380347A (en) * | 1993-01-21 | 1995-01-10 | Church & Dwight Co., Inc. | Blast media containing surfactant-clathrate compound |
US5412005A (en) * | 1991-05-03 | 1995-05-02 | Novamont S.P.A. | Biodegradable polymeric compositions based on starch and thermoplastic polymers |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
IT1232909B (en) * | 1989-08-07 | 1992-03-05 | Butterfly Srl | POLYMERIC COMPOSITION FOR THE PRODUCTION OF BIODEGRADABLE PLASTIC ITEMS INCLUDING DESTRUCTURED STARCH AND ETHYLENE COPOLYMER |
US5939467A (en) * | 1992-06-26 | 1999-08-17 | The Procter & Gamble Company | Biodegradable polymeric compositions and products thereof |
IT1274603B (en) * | 1994-08-08 | 1997-07-18 | Novamont Spa | BIODEGRADABLE PLASTIC EXPANDED MATERIALS |
-
1998
- 1998-03-13 CA CA002285458A patent/CA2285458A1/en not_active Abandoned
- 1998-03-13 WO PCT/US1998/005281 patent/WO1998040434A1/en not_active Application Discontinuation
- 1998-03-13 AU AU65641/98A patent/AU6564198A/en not_active Abandoned
- 1998-03-13 EP EP98911760A patent/EP0966502A4/en not_active Withdrawn
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5412005A (en) * | 1991-05-03 | 1995-05-02 | Novamont S.P.A. | Biodegradable polymeric compositions based on starch and thermoplastic polymers |
US5380347A (en) * | 1993-01-21 | 1995-01-10 | Church & Dwight Co., Inc. | Blast media containing surfactant-clathrate compound |
Non-Patent Citations (1)
Title |
---|
See also references of EP0966502A4 * |
Cited By (34)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6709526B1 (en) | 1999-03-08 | 2004-03-23 | The Procter & Gamble Company | Melt processable starch compositions |
US9458556B2 (en) | 1999-03-08 | 2016-10-04 | The Procter & Gamble Company | Fiber comprising polyvinylpyrrolidone |
US6811740B2 (en) | 2000-11-27 | 2004-11-02 | The Procter & Gamble Company | Process for making non-thermoplastic starch fibers |
US6723160B2 (en) | 2002-02-01 | 2004-04-20 | The Procter & Gamble Company | Non-thermoplastic starch fibers and starch composition for making same |
JP2004002773A (en) * | 2002-03-29 | 2004-01-08 | Mitsui Chemicals Inc | Lactic acid type resin composition |
EP1490435A4 (en) * | 2002-03-29 | 2007-10-17 | Mitsui Chemicals Inc | Lactic acid-based resin composition |
EP1490435A1 (en) * | 2002-03-29 | 2004-12-29 | Mitsui Chemicals, Inc. | Lactic acid-based resin composition |
WO2004080656A1 (en) * | 2003-03-14 | 2004-09-23 | Workinter Limited | Method for selective removal of materials present in one or more layers on an object, and apparatus for implementation of this method |
US7344651B2 (en) | 2003-03-14 | 2008-03-18 | Workinter Limited | Method for selective removal of materials present in one or more layers on an object, and apparatus for implementation of this method |
US9340657B2 (en) | 2003-06-06 | 2016-05-17 | The Procter & Gamble Company | Crosslinking systems for hydroxyl polymers |
US7947766B2 (en) | 2003-06-06 | 2011-05-24 | The Procter & Gamble Company | Crosslinking systems for hydroxyl polymers |
US7960453B2 (en) | 2003-06-06 | 2011-06-14 | The Procter & Gamble Company | Crosslinking systems for hydroxyl polymers |
US8088843B2 (en) | 2003-06-06 | 2012-01-03 | The Procter & Gamble Company | Crosslinking systems for hydroxyl polymers |
US8129449B2 (en) | 2003-06-06 | 2012-03-06 | The Procter & Gabmle Company | Crosslinking systems for hydroxyl polymers |
US8357237B2 (en) | 2003-06-06 | 2013-01-22 | The Procter & Gamble Company | Crosslinking systems for hydroxyl polymers |
US8617303B2 (en) | 2003-06-06 | 2013-12-31 | The Procter & Gamble Company | Crosslinking systems for hydroxyl polymers |
US8815003B2 (en) | 2003-06-06 | 2014-08-26 | The Procter & Gamble Company | Crosslinking systems for hydroxyl polymers |
US9017586B2 (en) | 2004-04-29 | 2015-04-28 | The Procter & Gamble Company | Polymeric structures and method for making same |
US8623246B2 (en) | 2004-04-29 | 2014-01-07 | The Procter & Gamble Company | Process of making a fibrous structure |
DE102008042893A1 (en) | 2008-10-16 | 2010-04-29 | Wacker Chemie Ag | Mixtures for the production of biodegradable moldings based on aliphatic polyesters and water-redispersible polymer powders |
US8202947B2 (en) | 2008-10-16 | 2012-06-19 | Wacker Chemie Ag | Mixtures for producing biodegradable aliphatic polyester-based molded bodies and for producing polymer powders that can be re-dispersed in water |
EP2228175A1 (en) * | 2009-03-12 | 2010-09-15 | Ferton Holding SA | Powder for powder streams, powder mixture and use for processing in particular dental surfaces |
US9888979B2 (en) | 2009-03-12 | 2018-02-13 | Ferton Holding S.A. | Method of powder blasting for cleaning of tooth surfaces |
US11787929B2 (en) | 2014-12-22 | 2023-10-17 | 3M Innovative Properties Company | Compositions and films comprising polylactic acid polymer, polyvinyl acetate polymer and plasticizer |
US11254812B2 (en) | 2014-12-22 | 2022-02-22 | 3M Innovative Properties Company | Compositions and films comprising polylactic acid polymer, polyvinyl acetate polymer and plasticizer |
EP3210723A1 (en) * | 2016-02-25 | 2017-08-30 | Kamei Tekkousho Ltd. | Abrasive materials |
US11066551B2 (en) | 2016-05-20 | 2021-07-20 | 3M Innovative Properties Company | Oriented polylactic acid polymer based film |
EP3472243A4 (en) * | 2016-06-21 | 2020-01-22 | 3M Innovative Properties Company | Graphic articles comprising semicrystalline polylactic acid based film |
CN109312147B (en) * | 2016-06-21 | 2021-04-16 | 3M创新有限公司 | Graphic article comprising semicrystalline polylactic acid-based film |
US10982090B2 (en) | 2016-06-21 | 2021-04-20 | 3M Innovative Properties Company | Graphic articles comprising polylactic acid polymer based film |
EP3835361A1 (en) * | 2016-06-21 | 2021-06-16 | 3M Innovative Properties Company | Graphic articles comprising semicrystalline polylactic acid polymer based film |
CN109312147A (en) * | 2016-06-21 | 2019-02-05 | 3M创新有限公司 | Graphic article including hypocrystalline polylactic acid basement membrane |
WO2017222824A1 (en) | 2016-06-21 | 2017-12-28 | 3M Innovative Properties Company | Graphic articles comprising semicrystalline polylactic acid based film |
WO2020079902A1 (en) * | 2018-10-17 | 2020-04-23 | 株式会社ダイセル | Treatment granules, compounding unit equipped with treatment granules, and production method for treatment granules |
Also Published As
Publication number | Publication date |
---|---|
EP0966502A1 (en) | 1999-12-29 |
AU6564198A (en) | 1998-09-29 |
EP0966502A4 (en) | 2000-05-10 |
CA2285458A1 (en) | 1998-09-17 |
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