CA2768856A1 - Making renewable polyoxymethylene compositions - Google Patents
Making renewable polyoxymethylene compositions Download PDFInfo
- Publication number
- CA2768856A1 CA2768856A1 CA2768856A CA2768856A CA2768856A1 CA 2768856 A1 CA2768856 A1 CA 2768856A1 CA 2768856 A CA2768856 A CA 2768856A CA 2768856 A CA2768856 A CA 2768856A CA 2768856 A1 CA2768856 A1 CA 2768856A1
- Authority
- CA
- Canada
- Prior art keywords
- polyoxymethylene
- formaldehyde
- carbon
- percent
- biobased content
- 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
- 229920006324 polyoxymethylene Polymers 0.000 title claims abstract description 97
- 229930040373 Paraformaldehyde Natural products 0.000 title claims abstract description 69
- -1 polyoxymethylene Polymers 0.000 title claims abstract description 62
- 239000000203 mixture Substances 0.000 title claims abstract description 59
- 238000000034 method Methods 0.000 claims abstract description 63
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 145
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 110
- 229910052799 carbon Inorganic materials 0.000 claims description 80
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 78
- 229920000642 polymer Polymers 0.000 claims description 25
- 230000015572 biosynthetic process Effects 0.000 claims description 21
- 238000003786 synthesis reaction Methods 0.000 claims description 21
- 239000000945 filler Substances 0.000 claims description 18
- 239000004698 Polyethylene Substances 0.000 claims description 11
- 229920000573 polyethylene Polymers 0.000 claims description 11
- 229920001038 ethylene copolymer Polymers 0.000 claims description 10
- 239000003054 catalyst Substances 0.000 claims description 9
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 9
- 229920001577 copolymer Polymers 0.000 claims description 8
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 claims description 8
- 229920012196 Polyoxymethylene Copolymer Polymers 0.000 claims description 6
- 239000011521 glass Substances 0.000 claims description 6
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 claims description 5
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 4
- 239000002028 Biomass Substances 0.000 claims description 4
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 claims description 4
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims description 4
- 125000005250 alkyl acrylate group Chemical group 0.000 claims description 4
- 150000002148 esters Chemical class 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 239000000843 powder Substances 0.000 claims description 4
- 239000007787 solid Substances 0.000 claims description 4
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 claims description 3
- 239000004952 Polyamide Substances 0.000 claims description 3
- 229920009382 Polyoxymethylene Homopolymer Polymers 0.000 claims description 3
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- 238000002156 mixing Methods 0.000 claims description 3
- 229920000747 poly(lactic acid) Polymers 0.000 claims description 3
- 229920002647 polyamide Polymers 0.000 claims description 3
- 239000004626 polylactic acid Substances 0.000 claims description 3
- 230000000379 polymerizing effect Effects 0.000 claims description 3
- 229920001897 terpolymer Polymers 0.000 claims description 3
- 239000003017 thermal stabilizer Substances 0.000 claims description 3
- WMGFVAGNIYUEEP-UHFFFAOYSA-N 2-[6-[[4,5-dihydroxy-3-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-6-[4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxyoxan-2-yl]methoxy]-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound OC1C(O)C(O)C(CO)OC1OC1C(CO)OC(OCC2C(C(O)C(O)C(OC3C(OC(O)C(O)C3O)CO)O2)OC2C(C(O)C(O)C(CO)O2)O)C(O)C1O WMGFVAGNIYUEEP-UHFFFAOYSA-N 0.000 claims description 2
- JESXATFQYMPTNL-UHFFFAOYSA-N 2-ethenylphenol Chemical class OC1=CC=CC=C1C=C JESXATFQYMPTNL-UHFFFAOYSA-N 0.000 claims description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 2
- 239000004113 Sepiolite Substances 0.000 claims description 2
- 229920002472 Starch Polymers 0.000 claims description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 2
- 150000001252 acrylic acid derivatives Chemical class 0.000 claims description 2
- 239000004760 aramid Substances 0.000 claims description 2
- 229920003235 aromatic polyamide Polymers 0.000 claims description 2
- 229910000019 calcium carbonate Inorganic materials 0.000 claims description 2
- QXJJQWWVWRCVQT-UHFFFAOYSA-K calcium;sodium;phosphate Chemical compound [Na+].[Ca+2].[O-]P([O-])([O-])=O QXJJQWWVWRCVQT-UHFFFAOYSA-K 0.000 claims description 2
- 239000004927 clay Substances 0.000 claims description 2
- 229910052570 clay Inorganic materials 0.000 claims description 2
- HGGNZMUHOHGHBJ-UHFFFAOYSA-N dioxepane Chemical compound C1CCOOCC1 HGGNZMUHOHGHBJ-UHFFFAOYSA-N 0.000 claims description 2
- 150000004676 glycans Chemical class 0.000 claims description 2
- 239000010445 mica Substances 0.000 claims description 2
- 229910052618 mica group Inorganic materials 0.000 claims description 2
- 230000001590 oxidative effect Effects 0.000 claims description 2
- 229920002401 polyacrylamide Polymers 0.000 claims description 2
- 229920001282 polysaccharide Polymers 0.000 claims description 2
- 239000005017 polysaccharide Substances 0.000 claims description 2
- 229910052624 sepiolite Inorganic materials 0.000 claims description 2
- 235000019355 sepiolite Nutrition 0.000 claims description 2
- 239000008107 starch Substances 0.000 claims description 2
- 235000019698 starch Nutrition 0.000 claims description 2
- 229920006249 styrenic copolymer Polymers 0.000 claims description 2
- 239000000454 talc Substances 0.000 claims description 2
- 229910052623 talc Inorganic materials 0.000 claims description 2
- 239000004408 titanium dioxide Substances 0.000 claims description 2
- 239000010456 wollastonite Substances 0.000 claims description 2
- 229910052882 wollastonite Inorganic materials 0.000 claims description 2
- 239000003365 glass fiber Substances 0.000 claims 2
- VDFVNEFVBPFDSB-UHFFFAOYSA-N 1,3-dioxane Chemical compound C1COCOC1 VDFVNEFVBPFDSB-UHFFFAOYSA-N 0.000 claims 1
- 229920000945 Amylopectin Polymers 0.000 claims 1
- 229920000049 Carbon (fiber) Polymers 0.000 claims 1
- 239000006229 carbon black Substances 0.000 claims 1
- 239000004917 carbon fiber Substances 0.000 claims 1
- 238000007334 copolymerization reaction Methods 0.000 claims 1
- 229910052500 inorganic mineral Inorganic materials 0.000 claims 1
- 239000011707 mineral Substances 0.000 claims 1
- AHHWIHXENZJRFG-UHFFFAOYSA-N oxetane Chemical compound C1COC1 AHHWIHXENZJRFG-UHFFFAOYSA-N 0.000 claims 1
- 235000019256 formaldehyde Nutrition 0.000 description 42
- 239000000463 material Substances 0.000 description 36
- 239000007789 gas Substances 0.000 description 16
- 230000000694 effects Effects 0.000 description 7
- 239000000543 intermediate Substances 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- 241001465754 Metazoa Species 0.000 description 6
- 239000000654 additive Substances 0.000 description 6
- 239000012298 atmosphere Substances 0.000 description 6
- 239000003963 antioxidant agent Substances 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000011248 coating agent Substances 0.000 description 5
- 238000000576 coating method Methods 0.000 description 5
- 239000000194 fatty acid Substances 0.000 description 5
- 239000000835 fiber Substances 0.000 description 5
- 239000002803 fossil fuel Substances 0.000 description 5
- 239000000314 lubricant Substances 0.000 description 5
- 229910001868 water Inorganic materials 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- 229920001519 homopolymer Polymers 0.000 description 4
- 238000000465 moulding Methods 0.000 description 4
- 230000003647 oxidation Effects 0.000 description 4
- 238000007254 oxidation reaction Methods 0.000 description 4
- 238000006116 polymerization reaction Methods 0.000 description 4
- 239000002243 precursor Substances 0.000 description 4
- 235000013311 vegetables Nutrition 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- BGJSXRVXTHVRSN-UHFFFAOYSA-N 1,3,5-trioxane Chemical compound C1OCOCO1 BGJSXRVXTHVRSN-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-NJFSPNSNSA-N Carbon-14 Chemical compound [14C] OKTJSMMVPCPJKN-NJFSPNSNSA-N 0.000 description 3
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 3
- 239000005977 Ethylene Substances 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 125000001033 ether group Chemical group 0.000 description 3
- 229930195729 fatty acid Natural products 0.000 description 3
- 150000004665 fatty acids Chemical class 0.000 description 3
- 239000000446 fuel Substances 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 241000196324 Embryophyta Species 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 239000004609 Impact Modifier Substances 0.000 description 2
- 239000012963 UV stabilizer Substances 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 238000000071 blow moulding Methods 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000001569 carbon dioxide Substances 0.000 description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000012937 correction Methods 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 238000001125 extrusion Methods 0.000 description 2
- 239000003925 fat Substances 0.000 description 2
- 239000008098 formaldehyde solution Substances 0.000 description 2
- 238000005227 gel permeation chromatography Methods 0.000 description 2
- 239000012760 heat stabilizer Substances 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 238000001746 injection moulding Methods 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- SNVLJLYUUXKWOJ-UHFFFAOYSA-N methylidenecarbene Chemical compound C=[C] SNVLJLYUUXKWOJ-UHFFFAOYSA-N 0.000 description 2
- 239000003607 modifier Substances 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 239000003345 natural gas Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 235000019198 oils Nutrition 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 229920002866 paraformaldehyde Polymers 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- 239000004014 plasticizer Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000002791 soaking Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 235000015112 vegetable and seed oil Nutrition 0.000 description 2
- 239000008158 vegetable oil Substances 0.000 description 2
- BYEAHWXPCBROCE-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-ol Chemical compound FC(F)(F)C(O)C(F)(F)F BYEAHWXPCBROCE-UHFFFAOYSA-N 0.000 description 1
- CHRJZRDFSQHIFI-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;styrene Chemical compound C=CC1=CC=CC=C1.C=CC1=CC=CC=C1C=C CHRJZRDFSQHIFI-UHFFFAOYSA-N 0.000 description 1
- QSRJVOOOWGXUDY-UHFFFAOYSA-N 2-[2-[2-[3-(3-tert-butyl-4-hydroxy-5-methylphenyl)propanoyloxy]ethoxy]ethoxy]ethyl 3-(3-tert-butyl-4-hydroxy-5-methylphenyl)propanoate Chemical compound CC(C)(C)C1=C(O)C(C)=CC(CCC(=O)OCCOCCOCCOC(=O)CCC=2C=C(C(O)=C(C)C=2)C(C)(C)C)=C1 QSRJVOOOWGXUDY-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
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- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 1
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 1
- 239000005639 Lauric acid Substances 0.000 description 1
- 229920002302 Nylon 6,6 Polymers 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
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- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
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- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
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- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- NZBSCACSYKRAHE-UHFFFAOYSA-N [O-2].[O-2].[Fe+2].[Mo+2]=O Chemical compound [O-2].[O-2].[Fe+2].[Mo+2]=O NZBSCACSYKRAHE-UHFFFAOYSA-N 0.000 description 1
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- RHZUVFJBSILHOK-UHFFFAOYSA-N anthracen-1-ylmethanolate Chemical compound C1=CC=C2C=C3C(C[O-])=CC=CC3=CC2=C1 RHZUVFJBSILHOK-UHFFFAOYSA-N 0.000 description 1
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- 150000001923 cyclic compounds Chemical class 0.000 description 1
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- RKISUIUJZGSLEV-UHFFFAOYSA-N n-[2-(octadecanoylamino)ethyl]octadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(=O)NCCNC(=O)CCCCCCCCCCCCCCCCC RKISUIUJZGSLEV-UHFFFAOYSA-N 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L59/00—Compositions of polyacetals; Compositions of derivatives of polyacetals
- C08L59/04—Copolyoxymethylenes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L59/00—Compositions of polyacetals; Compositions of derivatives of polyacetals
- C08L59/02—Polyacetals containing polyoxymethylene sequences only
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2/00—Addition polymers of aldehydes or cyclic oligomers thereof or of ketones; Addition copolymers thereof with less than 50 molar percent of other substances
- C08G2/08—Polymerisation of formaldehyde
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
-
- 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
- C08L3/12—Amylose; Amylopectin; Degradation products thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Manufacturing & Machinery (AREA)
- Materials Engineering (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US23078909P | 2009-08-03 | 2009-08-03 | |
| US61/230,789 | 2009-08-03 | ||
| PCT/US2010/044296 WO2011017359A2 (en) | 2009-08-03 | 2010-08-03 | Making renewable polyoxymethylene compositions |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2768856A1 true CA2768856A1 (en) | 2011-02-10 |
Family
ID=43527621
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2769195A Abandoned CA2769195A1 (en) | 2009-08-03 | 2010-08-03 | Renewable polyoxymethylene compositions and articles therefrom |
| CA2768856A Abandoned CA2768856A1 (en) | 2009-08-03 | 2010-08-03 | Making renewable polyoxymethylene compositions |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2769195A Abandoned CA2769195A1 (en) | 2009-08-03 | 2010-08-03 | Renewable polyoxymethylene compositions and articles therefrom |
Country Status (9)
| Country | Link |
|---|---|
| US (2) | US20110028631A1 (OSRAM) |
| EP (2) | EP2462193A4 (OSRAM) |
| JP (2) | JP2013501132A (OSRAM) |
| KR (2) | KR20120055590A (OSRAM) |
| CN (2) | CN102549067A (OSRAM) |
| BR (2) | BR112012002404A2 (OSRAM) |
| CA (2) | CA2769195A1 (OSRAM) |
| IN (1) | IN2012DN00561A (OSRAM) |
| WO (2) | WO2011017359A2 (OSRAM) |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8188169B2 (en) * | 2008-08-29 | 2012-05-29 | E. I. Du Pont De Nemours And Company | Polyoxymethylene compositions and articles made from these |
| US20110028631A1 (en) * | 2009-08-03 | 2011-02-03 | E. I. Du Pont De Nemours And Company | Renewable Polyoxymethylene Compositions and Articles Therefrom |
| FR2958649B1 (fr) * | 2010-04-07 | 2012-05-04 | Arkema France | Copolymere a blocs issu de matieres renouvelables et procede de fabrication d'un tel copolymere a blocs |
| CN102516705A (zh) * | 2011-12-16 | 2012-06-27 | 唐山中浩化工有限公司 | 光稳定的聚甲醛组合物 |
| KR20140015990A (ko) * | 2012-07-27 | 2014-02-07 | (주)엘지하우시스 | 자동차 내장재용 열가소성 수지 조성물 및 자동차 내장재 성형품 |
| WO2014100657A2 (en) * | 2012-12-20 | 2014-06-26 | Ticona Llc | Monofilament fibers made from a polyoxymethylene composition |
| KR101504676B1 (ko) * | 2013-03-27 | 2015-03-20 | 한국엔지니어링플라스틱 주식회사 | 유리섬유가 강화된 폴리옥시메틸렌-폴리락트산 조성물 |
| CN103289032B (zh) * | 2013-06-03 | 2016-01-20 | 中国科学院青岛生物能源与过程研究所 | 一种氧杂环丁烷衍生物共聚改性聚甲醛的制备方法 |
| US20150028247A1 (en) | 2013-07-23 | 2015-01-29 | Sabic Innovative Plastics Ip B.V. | Rigid foam and associated article and method |
| US9175160B2 (en) | 2013-08-28 | 2015-11-03 | Sabic Global Technologies B.V. | Blend of poly(phenylene ether) particles and polyoxymethylene, article thereof, and method of preparation |
| US9447227B2 (en) | 2013-10-03 | 2016-09-20 | Sabic Global Technologies B.V. | Flexible polyurethane foam and associated method and article |
| EP3092125B1 (en) * | 2014-01-09 | 2023-08-16 | Novalis Holdings Limited | Surface covering with a bio-based plasticizer |
| WO2016034668A1 (en) | 2014-09-05 | 2016-03-10 | Sabic Global Technologies B.V. | Polyoxymethylene compositions, method for manufacture, and articles made therefrom |
| CN104861412B (zh) * | 2015-04-29 | 2017-06-09 | 洛阳市河之阳高分子材料有限公司 | 一种用于空调曲柄的pom材料及其制备方法 |
| CN106221118A (zh) * | 2016-08-24 | 2016-12-14 | 桂林浩新科技服务有限公司 | 一种高延展性的聚甲醛树脂组合物 |
| NL2020686B1 (en) * | 2018-03-29 | 2019-10-07 | De Patent B V | Scratch resistant polymer composition |
| CN108912592A (zh) * | 2018-08-03 | 2018-11-30 | 安徽江淮汽车集团股份有限公司 | 一种聚甲醛复合材料及其制备方法 |
| WO2020232333A1 (en) * | 2019-05-16 | 2020-11-19 | Lungpacer Medical Inc. | Systems and methods for sensing and stimulation |
| JP2023537628A (ja) * | 2020-08-14 | 2023-09-04 | セラニーズ・インターナショナル・コーポレーション | ポリオキシメチレンコポリマーを製造するためのバイオマスの使用 |
| US11545318B2 (en) * | 2020-10-28 | 2023-01-03 | Dell Products L.P. | Keyboard containing recycled and renewable polymeric compositions |
| CN113912978B (zh) * | 2021-10-18 | 2024-03-22 | 浙江伟星实业发展股份有限公司 | 一种生物基注塑拉链及其制备方法 |
| CN114752134B (zh) * | 2022-06-15 | 2022-09-09 | 河北上东包装科技有限公司 | 一种聚乙烯易撕膜 |
| CN116359409A (zh) * | 2023-03-17 | 2023-06-30 | 海南省产品质量监督检验所 | 生物降解制品中不可降解塑料成分测定方法 |
Family Cites Families (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1383059A (en) * | 1920-05-26 | 1921-06-28 | Barrett Co | Process of producing formaldehyde |
| US1569775A (en) * | 1924-09-04 | 1926-01-12 | Basf Ag | Synthetic manufacture of methanol |
| US3198753A (en) * | 1960-03-22 | 1965-08-03 | Montedison Spa | Catalyst composition consisting of the oxides of molybdenum, iron and cobalt |
| US3883468A (en) * | 1972-12-22 | 1975-05-13 | Basf Ag | Thermoplastic molding compositions |
| JPS53111348A (en) * | 1977-03-10 | 1978-09-28 | Asahi Chem Ind Co Ltd | Polyoxymethylene composition |
| US5286807A (en) * | 1983-02-07 | 1994-02-15 | E. I. Du Pont De Nemours And Company | Impact resistant polyoxymethylene compositions |
| US5232965A (en) * | 1991-03-22 | 1993-08-03 | E. I. Du Pont De Nemours And Company | Stabilized polyacetal compositions |
| US6077908A (en) * | 1995-09-07 | 2000-06-20 | Asahi Kasei Kogyo Kabushiki Kaisha | Polyoxymethylene resin composition |
| DE19920830A1 (de) * | 1999-05-06 | 2000-11-09 | Ticona Gmbh | Trimerisierung von Formaldehyd in der Gasphase |
| WO2001018154A1 (en) * | 1999-09-06 | 2001-03-15 | Agrofuel Ab | Motor fuel for diesel engines |
| KR100590973B1 (ko) * | 2000-02-29 | 2006-06-19 | 미츠비시 쥬고교 가부시키가이샤 | 바이오매스 가스화 가스를 이용한 메탄올 합성 장치 및 이의 사용방법 |
| CN1166736C (zh) * | 2000-09-13 | 2004-09-15 | 中国石油化工股份有限公司 | 一种高韧性聚甲醛组合物及其制备方法 |
| CN1307259C (zh) * | 2001-08-03 | 2007-03-28 | 东丽株式会社 | 树脂组合物和由该树脂组合物制成的成型制品、薄膜和纤维 |
| CR7573A (es) * | 2004-11-11 | 2005-06-08 | Araya Brenes Mario | Composicion de un combustible y/o biocombustible a base de alcohol para sustituir gasolina, diesel o aceites combustibles en motores convencionales de combustion interna y metodo para su empleo |
| AU2006236802B2 (en) * | 2005-04-15 | 2011-09-01 | University Of Southern California | Selective oxidative conversion of methane to methanol, dimethyl ether and derived products |
| DE102005030282A1 (de) * | 2005-06-29 | 2007-01-04 | Basf Ag | Biodieselkraftstoffgemisch enthaltend Polyoxymethylendialkylether |
| EP1922346A1 (de) * | 2005-08-26 | 2008-05-21 | Basf Se | Verfahren zur herstellung von polyoxymethylenhomo- oder -copolymeren |
| AU2007230667B2 (en) * | 2006-03-24 | 2011-02-03 | Virent Energy Systems, Inc. | Method for producing bio-fuel that integrates heat from carbon-carbon bond-forming reactions to drive biomass gasification reactions |
| CN101130621B (zh) * | 2007-09-14 | 2011-01-12 | 深圳市科聚新材料有限公司 | 一种增强增韧聚甲醛组合物及其制备方法 |
| MX2010005954A (es) * | 2007-12-19 | 2010-06-11 | Basf Se | Metodo para la produccion de homopolimeros o copolimeros de polioximetileno por homopolimerizacion o copolimerizacion de trioxano, iniciando a partir de metanol. |
| US20110028631A1 (en) * | 2009-08-03 | 2011-02-03 | E. I. Du Pont De Nemours And Company | Renewable Polyoxymethylene Compositions and Articles Therefrom |
-
2010
- 2010-08-02 US US12/848,506 patent/US20110028631A1/en not_active Abandoned
- 2010-08-02 US US12/848,528 patent/US20110028609A1/en not_active Abandoned
- 2010-08-03 KR KR1020127005667A patent/KR20120055590A/ko not_active Withdrawn
- 2010-08-03 WO PCT/US2010/044296 patent/WO2011017359A2/en not_active Ceased
- 2010-08-03 JP JP2012523714A patent/JP2013501132A/ja active Pending
- 2010-08-03 BR BR112012002404A patent/BR112012002404A2/pt not_active IP Right Cessation
- 2010-08-03 CN CN2010800451063A patent/CN102549067A/zh active Pending
- 2010-08-03 JP JP2012523713A patent/JP2013501131A/ja active Pending
- 2010-08-03 CN CN2010800450751A patent/CN102549066A/zh active Pending
- 2010-08-03 CA CA2769195A patent/CA2769195A1/en not_active Abandoned
- 2010-08-03 CA CA2768856A patent/CA2768856A1/en not_active Abandoned
- 2010-08-03 EP EP10807050.9A patent/EP2462193A4/en not_active Withdrawn
- 2010-08-03 EP EP10807052.5A patent/EP2462194A4/en not_active Withdrawn
- 2010-08-03 BR BR112012002402A patent/BR112012002402A2/pt not_active IP Right Cessation
- 2010-08-03 WO PCT/US2010/044294 patent/WO2011017357A2/en not_active Ceased
- 2010-08-03 KR KR1020127005665A patent/KR20120055589A/ko not_active Withdrawn
-
2012
- 2012-01-19 IN IN561DEN2012 patent/IN2012DN00561A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| BR112012002402A2 (pt) | 2019-09-24 |
| CA2769195A1 (en) | 2011-02-10 |
| BR112012002404A2 (pt) | 2019-09-24 |
| WO2011017359A3 (en) | 2011-05-19 |
| US20110028631A1 (en) | 2011-02-03 |
| IN2012DN00561A (OSRAM) | 2015-06-12 |
| CN102549067A (zh) | 2012-07-04 |
| WO2011017359A2 (en) | 2011-02-10 |
| WO2011017357A3 (en) | 2011-05-19 |
| WO2011017357A2 (en) | 2011-02-10 |
| KR20120055590A (ko) | 2012-05-31 |
| US20110028609A1 (en) | 2011-02-03 |
| EP2462194A2 (en) | 2012-06-13 |
| EP2462193A4 (en) | 2013-12-25 |
| JP2013501131A (ja) | 2013-01-10 |
| CN102549066A (zh) | 2012-07-04 |
| EP2462194A4 (en) | 2013-12-25 |
| KR20120055589A (ko) | 2012-05-31 |
| EP2462193A2 (en) | 2012-06-13 |
| JP2013501132A (ja) | 2013-01-10 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |
Effective date: 20150804 |