CA1101584A - Production of an improved non-reinforced polyoxymethylene molding composition which forms reduced mold deposits upon molding - Google Patents
Production of an improved non-reinforced polyoxymethylene molding composition which forms reduced mold deposits upon moldingInfo
- Publication number
- CA1101584A CA1101584A CA292,351A CA292351A CA1101584A CA 1101584 A CA1101584 A CA 1101584A CA 292351 A CA292351 A CA 292351A CA 1101584 A CA1101584 A CA 1101584A
- Authority
- CA
- Canada
- Prior art keywords
- polyoxymethylene
- molding composition
- free
- poly
- producing
- 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
Links
- 229920006324 polyoxymethylene Polymers 0.000 title claims abstract description 116
- -1 polyoxymethylene Polymers 0.000 title claims abstract description 107
- 229930040373 Paraformaldehyde Natural products 0.000 title claims abstract description 93
- 239000000203 mixture Substances 0.000 title claims abstract description 77
- 238000000465 moulding Methods 0.000 title claims abstract description 62
- 238000004519 manufacturing process Methods 0.000 title abstract description 4
- 125000003118 aryl group Chemical group 0.000 claims abstract description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 6
- 238000000034 method Methods 0.000 claims description 39
- 229920000642 polymer Polymers 0.000 claims description 37
- 150000001718 carbodiimides Chemical group 0.000 claims description 27
- 238000010438 heat treatment Methods 0.000 claims description 17
- 230000002787 reinforcement Effects 0.000 claims description 17
- 239000002253 acid Substances 0.000 claims description 16
- 229920001577 copolymer Polymers 0.000 claims description 10
- 238000001746 injection moulding Methods 0.000 claims description 10
- 239000003963 antioxidant agent Substances 0.000 claims description 8
- 239000000243 solution Substances 0.000 claims description 6
- 230000007062 hydrolysis Effects 0.000 claims description 5
- 238000006460 hydrolysis reaction Methods 0.000 claims description 5
- 239000002516 radical scavenger Substances 0.000 claims description 5
- 230000003078 antioxidant effect Effects 0.000 claims description 4
- GRWFGVWFFZKLTI-UHFFFAOYSA-N α-pinene Chemical compound CC1=CCC2C(C)(C)C1C2 GRWFGVWFFZKLTI-UHFFFAOYSA-N 0.000 claims description 4
- 238000002844 melting Methods 0.000 claims description 3
- 230000008018 melting Effects 0.000 claims description 3
- GRWFGVWFFZKLTI-IUCAKERBSA-N 1S,5S-(-)-alpha-Pinene Natural products CC1=CC[C@@H]2C(C)(C)[C@H]1C2 GRWFGVWFFZKLTI-IUCAKERBSA-N 0.000 claims description 2
- WXNZTHHGJRFXKQ-UHFFFAOYSA-N 4-chlorophenol Chemical compound OC1=CC=C(Cl)C=C1 WXNZTHHGJRFXKQ-UHFFFAOYSA-N 0.000 claims description 2
- MVNCAPSFBDBCGF-UHFFFAOYSA-N alpha-pinene Natural products CC1=CCC23C1CC2C3(C)C MVNCAPSFBDBCGF-UHFFFAOYSA-N 0.000 claims description 2
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical group NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 claims description 2
- 239000000835 fiber Substances 0.000 claims description 2
- AQLIOEZBUVJRMW-UHFFFAOYSA-N 4-tert-butyl-2-[(5-tert-butyl-2-hydroxy-5-methylcyclohexa-1,3-dien-1-yl)methyl]-4-methylcyclohexa-1,5-dien-1-ol Chemical group C1=CC(C(C)(C)C)(C)CC(CC=2CC(C)(C=CC=2O)C(C)(C)C)=C1O AQLIOEZBUVJRMW-UHFFFAOYSA-N 0.000 claims 1
- VPKDCDLSJZCGKE-UHFFFAOYSA-N carbodiimide group Chemical group N=C=N VPKDCDLSJZCGKE-UHFFFAOYSA-N 0.000 abstract 1
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 33
- 239000000654 additive Substances 0.000 description 21
- 230000000996 additive effect Effects 0.000 description 16
- 230000015556 catabolic process Effects 0.000 description 15
- 238000006731 degradation reaction Methods 0.000 description 15
- 235000019256 formaldehyde Nutrition 0.000 description 11
- 229960004279 formaldehyde Drugs 0.000 description 11
- 239000003054 catalyst Substances 0.000 description 8
- 230000006641 stabilisation Effects 0.000 description 8
- 238000011105 stabilization Methods 0.000 description 8
- 238000005755 formation reaction Methods 0.000 description 7
- 230000002378 acidificating effect Effects 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 229920001519 homopolymer Polymers 0.000 description 5
- 239000012948 isocyanate Substances 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 5
- BGJSXRVXTHVRSN-UHFFFAOYSA-N 1,3,5-trioxane Chemical compound C1OCOCO1 BGJSXRVXTHVRSN-UHFFFAOYSA-N 0.000 description 4
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- 229920013683 Celanese Polymers 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 4
- 238000005917 acylation reaction Methods 0.000 description 4
- 238000012668 chain scission Methods 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 150000003949 imides Chemical class 0.000 description 4
- 150000002513 isocyanates Chemical class 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 125000005704 oxymethylene group Chemical group [H]C([H])([*:2])O[*:1] 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- 229920012196 Polyoxymethylene Copolymer Polymers 0.000 description 3
- 230000010933 acylation Effects 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 125000005442 diisocyanate group Chemical group 0.000 description 3
- 238000001125 extrusion Methods 0.000 description 3
- 239000000155 melt Substances 0.000 description 3
- 230000001590 oxidative effect Effects 0.000 description 3
- 230000000704 physical effect Effects 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- JRVZITODZAQRQM-UHFFFAOYSA-N 1-isocyanato-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1N=C=O JRVZITODZAQRQM-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 230000002411 adverse Effects 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 150000004292 cyclic ethers Chemical class 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 230000001419 dependent effect Effects 0.000 description 2
- RAABOESOVLLHRU-UHFFFAOYSA-N diazene Chemical compound N=N RAABOESOVLLHRU-UHFFFAOYSA-N 0.000 description 2
- 229910000071 diazene Inorganic materials 0.000 description 2
- 239000000314 lubricant Substances 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 238000003801 milling Methods 0.000 description 2
- CMESPBFFDMPSIY-UHFFFAOYSA-N n,n'-diphenylmethanediimine Chemical compound C1=CC=CC=C1N=C=NC1=CC=CC=C1 CMESPBFFDMPSIY-UHFFFAOYSA-N 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 230000000087 stabilizing effect Effects 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 description 2
- 238000011282 treatment Methods 0.000 description 2
- 238000013022 venting Methods 0.000 description 2
- RBACIKXCRWGCBB-UHFFFAOYSA-N 1,2-Epoxybutane Chemical compound CCC1CO1 RBACIKXCRWGCBB-UHFFFAOYSA-N 0.000 description 1
- VUMCUSHVMYIRMB-UHFFFAOYSA-N 1,3,5-tri(propan-2-yl)benzene Chemical compound CC(C)C1=CC(C(C)C)=CC(C(C)C)=C1 VUMCUSHVMYIRMB-UHFFFAOYSA-N 0.000 description 1
- ULAGGPJVDRGWTI-UHFFFAOYSA-N 1,3,5-trioxepane Chemical compound C1COCOCO1 ULAGGPJVDRGWTI-UHFFFAOYSA-N 0.000 description 1
- VGHSXKTVMPXHNG-UHFFFAOYSA-N 1,3-diisocyanatobenzene Chemical compound O=C=NC1=CC=CC(N=C=O)=C1 VGHSXKTVMPXHNG-UHFFFAOYSA-N 0.000 description 1
- VDFVNEFVBPFDSB-UHFFFAOYSA-N 1,3-dioxane Chemical compound C1COCOC1 VDFVNEFVBPFDSB-UHFFFAOYSA-N 0.000 description 1
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 description 1
- ALQLPWJFHRMHIU-UHFFFAOYSA-N 1,4-diisocyanatobenzene Chemical compound O=C=NC1=CC=C(N=C=O)C=C1 ALQLPWJFHRMHIU-UHFFFAOYSA-N 0.000 description 1
- HHIRBXHEYVDUAM-UHFFFAOYSA-N 1-chloro-3-isocyanatobenzene Chemical compound ClC1=CC=CC(N=C=O)=C1 HHIRBXHEYVDUAM-UHFFFAOYSA-N 0.000 description 1
- ADAKRBAJFHTIEW-UHFFFAOYSA-N 1-chloro-4-isocyanatobenzene Chemical compound ClC1=CC=C(N=C=O)C=C1 ADAKRBAJFHTIEW-UHFFFAOYSA-N 0.000 description 1
- NPOVTGVGOBJZPY-UHFFFAOYSA-N 1-isocyanato-3-methoxybenzene Chemical compound COC1=CC=CC(N=C=O)=C1 NPOVTGVGOBJZPY-UHFFFAOYSA-N 0.000 description 1
- CPPGZWWUPFWALU-UHFFFAOYSA-N 1-isocyanato-3-methylbenzene Chemical compound CC1=CC=CC(N=C=O)=C1 CPPGZWWUPFWALU-UHFFFAOYSA-N 0.000 description 1
- ICLCCFKUSALICQ-UHFFFAOYSA-N 1-isocyanato-4-(4-isocyanato-3-methylphenyl)-2-methylbenzene Chemical compound C1=C(N=C=O)C(C)=CC(C=2C=C(C)C(N=C=O)=CC=2)=C1 ICLCCFKUSALICQ-UHFFFAOYSA-N 0.000 description 1
- FMDGXCSMDZMDHZ-UHFFFAOYSA-N 1-isocyanato-4-methoxybenzene Chemical compound COC1=CC=C(N=C=O)C=C1 FMDGXCSMDZMDHZ-UHFFFAOYSA-N 0.000 description 1
- KGRVJHAUYBGFFP-UHFFFAOYSA-N 2,2'-Methylenebis(4-methyl-6-tert-butylphenol) Chemical compound CC(C)(C)C1=CC(C)=CC(CC=2C(=C(C=C(C)C=2)C(C)(C)C)O)=C1O KGRVJHAUYBGFFP-UHFFFAOYSA-N 0.000 description 1
- VAYMIYBJLRRIFR-UHFFFAOYSA-N 2-tolyl isocyanate Chemical compound CC1=CC=CC=C1N=C=O VAYMIYBJLRRIFR-UHFFFAOYSA-N 0.000 description 1
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- MGYGFNQQGAQEON-UHFFFAOYSA-N 4-tolyl isocyanate Chemical compound CC1=CC=C(N=C=O)C=C1 MGYGFNQQGAQEON-UHFFFAOYSA-N 0.000 description 1
- 235000003930 Aegle marmelos Nutrition 0.000 description 1
- 244000058084 Aegle marmelos Species 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 1
- ZBVOEVQTNYNNMY-UHFFFAOYSA-N O=P1=CCCC1 Chemical class O=P1=CCCC1 ZBVOEVQTNYNNMY-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 1
- 230000021736 acetylation Effects 0.000 description 1
- 238000006640 acetylation reaction Methods 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000003712 anti-aging effect Effects 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 235000013877 carbamide Nutrition 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000003413 degradative effect Effects 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 235000013350 formula milk Nutrition 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000012760 heat stabilizer Substances 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 1
- 238000005065 mining Methods 0.000 description 1
- UCAOGXRUJFKQAP-UHFFFAOYSA-N n,n-dimethyl-5-nitropyridin-2-amine Chemical compound CN(C)C1=CC=C([N+]([O-])=O)C=N1 UCAOGXRUJFKQAP-UHFFFAOYSA-N 0.000 description 1
- RKISUIUJZGSLEV-UHFFFAOYSA-N n-[2-(octadecanoylamino)ethyl]octadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(=O)NCCNC(=O)CCCCCCCCCCCCCCCCC RKISUIUJZGSLEV-UHFFFAOYSA-N 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- AHHWIHXENZJRFG-UHFFFAOYSA-N oxetane Chemical compound C1COC1 AHHWIHXENZJRFG-UHFFFAOYSA-N 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- SQYNKIJPMDEDEG-UHFFFAOYSA-N paraldehyde Chemical compound CC1OC(C)OC(C)O1 SQYNKIJPMDEDEG-UHFFFAOYSA-N 0.000 description 1
- 229960003868 paraldehyde Drugs 0.000 description 1
- 229940059574 pentaerithrityl Drugs 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 239000000088 plastic resin Substances 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 125000005156 substituted alkylene group Chemical group 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000012815 thermoplastic material Substances 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- 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
- C08G2/30—Chemical modification by after-treatment
-
- 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
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L79/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen or carbon only, not provided for in groups C08L61/00 - C08L77/00
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Processing And Handling Of Plastics And Other Materials For Molding In General (AREA)
- Manufacture Of Macromolecular Shaped Articles (AREA)
- Polyurethanes Or Polyureas (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US75221276A | 1976-12-17 | 1976-12-17 | |
| US846,661 | 1977-10-28 | ||
| US05/846,661 US4293469A (en) | 1976-12-17 | 1977-10-28 | Production of an improved non-reinforced polyoxymethylene molding composition which forms reduced mold deposits upon molding |
| US752,212 | 1985-07-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1101584A true CA1101584A (en) | 1981-05-19 |
Family
ID=27115553
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA292,351A Expired CA1101584A (en) | 1976-12-17 | 1977-12-05 | Production of an improved non-reinforced polyoxymethylene molding composition which forms reduced mold deposits upon molding |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US4293469A (en, 2012) |
| JP (1) | JPS5377242A (en, 2012) |
| AU (1) | AU520367B2 (en, 2012) |
| BR (1) | BR7708341A (en, 2012) |
| CA (1) | CA1101584A (en, 2012) |
| DE (1) | DE2754579A1 (en, 2012) |
| FR (1) | FR2374364A1 (en, 2012) |
| GB (1) | GB1591263A (en, 2012) |
| IT (1) | IT1115698B (en, 2012) |
| NL (1) | NL184116C (en, 2012) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1246768A (en) * | 1983-02-25 | 1988-12-13 | Paul N. Richardson | Polyoxymethylene/polyurethane compositions containing polycarbodiimide |
| US4845161A (en) * | 1983-02-25 | 1989-07-04 | E. I. Du Pont De Nemours And Company | Polyoxymethylene/polyurethane compositions containing polycarbodiimide |
| JPS59159846A (ja) * | 1983-03-03 | 1984-09-10 | Mitsubishi Gas Chem Co Inc | アセタ−ル樹脂組成物 |
| CA1273767A (en) * | 1986-06-26 | 1990-09-11 | Alex S. Forschirm | Polyacetal lighter body resin |
| US4772654A (en) * | 1987-07-21 | 1988-09-20 | E. I. Du Pont De Nemours And Company | Fire resistant polymers containing magnesium oxychloride |
| US5362500A (en) * | 1992-12-04 | 1994-11-08 | Wm. Wrigley Jr. Company | Method of stabilizing chewing gum with an antioxidant containing tissue and product thereof |
| US6121406A (en) * | 1998-04-20 | 2000-09-19 | Nisshinbo Industries, Inc. | Mixture of hydrophilic dicyclohexylmethanecarbodiimide |
| JP3349439B2 (ja) * | 1998-07-08 | 2002-11-25 | 日清紡績株式会社 | ポリアセタール樹脂組成物 |
| WO2011046566A1 (en) * | 2009-10-16 | 2011-04-21 | Rhein Chemie Rheinau Gmbh | New formaldehyde scavengers |
| EP2418250A1 (de) * | 2010-08-11 | 2012-02-15 | Rhein Chemie Rheinau GmbH | Langlebige biobasierte Kunststoffe auf Basis von Polyhydroxyalkanoat, ein Verfahren zu deren Herstellung und deren Verwendung |
| JP2013100393A (ja) * | 2011-11-08 | 2013-05-23 | Mitsubishi Engineering Plastics Corp | ポリアセタール樹脂組成物 |
| ITBS20120122A1 (it) * | 2012-07-27 | 2014-01-28 | Emer Spa | Dispositivo di sicurezza, particolarmente per impianti a gas per autotrazione |
| US20210163730A1 (en) * | 2018-07-26 | 2021-06-03 | Dupont Polymers, Inc. | Metal-polyacetal assembly |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE586592A (en, 2012) * | 1959-01-16 | |||
| US3135718A (en) * | 1960-04-19 | 1964-06-02 | Bayer Ag | Polymerization of formaldehyde |
| NL302727A (en, 2012) * | 1962-12-29 | 1900-01-01 | ||
| US3755242A (en) * | 1972-04-10 | 1973-08-28 | Minnesota Mining & Mfg | Polycarbodiimide prepolymers |
| US3839267A (en) * | 1973-04-12 | 1974-10-01 | Celanese Corp | Heterogeneous melt hydrolysis of oxymethylene copolymers |
| CA1056985A (en) * | 1975-03-17 | 1979-06-19 | Celanese Corporation | Polyesters for extrusion applications |
-
1977
- 1977-10-28 US US05/846,661 patent/US4293469A/en not_active Expired - Lifetime
- 1977-11-30 GB GB49867/77A patent/GB1591263A/en not_active Expired
- 1977-12-01 AU AU31133/77A patent/AU520367B2/en not_active Expired
- 1977-12-05 CA CA292,351A patent/CA1101584A/en not_active Expired
- 1977-12-08 DE DE19772754579 patent/DE2754579A1/de active Granted
- 1977-12-09 JP JP14727877A patent/JPS5377242A/ja active Granted
- 1977-12-12 NL NLAANVRAGE7713721,A patent/NL184116C/xx not_active IP Right Cessation
- 1977-12-15 BR BR7708341A patent/BR7708341A/pt unknown
- 1977-12-16 IT IT30860/77A patent/IT1115698B/it active
- 1977-12-16 FR FR7738076A patent/FR2374364A1/fr active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6131142B2 (en, 2012) | 1986-07-18 |
| AU3113377A (en) | 1979-06-07 |
| NL184116C (nl) | 1989-04-17 |
| FR2374364B1 (en, 2012) | 1981-10-02 |
| DE2754579A1 (de) | 1978-06-22 |
| NL184116B (nl) | 1988-11-16 |
| GB1591263A (en) | 1981-06-17 |
| AU520367B2 (en) | 1982-01-28 |
| BR7708341A (pt) | 1978-08-08 |
| FR2374364A1 (fr) | 1978-07-13 |
| IT1115698B (it) | 1986-02-03 |
| DE2754579C2 (en, 2012) | 1991-09-19 |
| NL7713721A (nl) | 1978-06-20 |
| US4293469A (en) | 1981-10-06 |
| JPS5377242A (en) | 1978-07-08 |
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