CA1105187A - Process for the polymerization of formaldehyde - Google Patents

Process for the polymerization of formaldehyde

Info

Publication number: CA1105187A
Authority: CA; Canada
Prior art keywords: polymer; polyoxymethylene; formaldehyde; parts; catalyst
Prior art date: 1975-10-30
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

Application number

CA263,536A

Other languages

English (en)

French (fr)

Inventor

Pierino Radici

Paolo Colombo

Gaudenzio Bianchi

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Societa Italiana Resine SpA SIR

Original Assignee

Societa Italiana Resine SpA SIR

Priority date (The priority date 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 date listed.)

1975-10-30

Filing date

1976-10-15

Publication date

1981-07-14

1976-10-15 Application filed by Societa Italiana Resine SpA SIR filed Critical Societa Italiana Resine SpA SIR

1981-07-14 Application granted granted Critical

1981-07-14 Publication of CA1105187A publication Critical patent/CA1105187A/en

Status Expired legal-status Critical Current

Links

WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 title claims abstract description 123
238000006116 polymerization reaction Methods 0.000 title claims description 27
238000000034 method Methods 0.000 title claims description 19
-1 Polyoxymethylene Polymers 0.000 claims abstract description 76
229930040373 Paraformaldehyde Natural products 0.000 claims abstract description 57
229920006324 polyoxymethylene Polymers 0.000 claims abstract description 57
239000003054 catalyst Substances 0.000 claims abstract description 28
239000003085 diluting agent Substances 0.000 claims abstract description 13
239000012429 reaction media Substances 0.000 claims abstract description 13
239000002904 solvent Substances 0.000 claims abstract description 12
239000012986 chain transfer agent Substances 0.000 claims abstract description 7
229920000642 polymer Polymers 0.000 claims description 72
239000000178 monomer Substances 0.000 claims description 19
239000002245 particle Substances 0.000 claims description 16
238000006243 chemical reaction Methods 0.000 claims description 15
150000001875 compounds Chemical class 0.000 claims description 10
150000002596 lactones Chemical class 0.000 claims description 9
125000003118 aryl group Chemical group 0.000 claims description 7
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
125000000217 alkyl group Chemical group 0.000 claims description 6
125000004432 carbon atom Chemical group C* 0.000 claims description 6
229930195733 hydrocarbon Natural products 0.000 claims description 6
229910052751 metal Inorganic materials 0.000 claims description 5
239000002184 metal Substances 0.000 claims description 5
230000000737 periodic effect Effects 0.000 claims description 5
239000000470 constituent Substances 0.000 claims description 4
125000000753 cycloalkyl group Chemical group 0.000 claims description 4
239000007788 liquid Substances 0.000 claims description 4
238000002360 preparation method Methods 0.000 claims description 4
239000004215 Carbon black (E152) Substances 0.000 claims description 3
238000009835 boiling Methods 0.000 claims description 3
125000005466 alkylenyl group Chemical group 0.000 claims description 2
125000001453 quaternary ammonium group Chemical group 0.000 claims description 2
125000001424 substituent group Chemical group 0.000 claims description 2
PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 claims description 2
OZJPLYNZGCXSJM-UHFFFAOYSA-N 5-valerolactone Chemical compound O=C1CCCCO1 OZJPLYNZGCXSJM-UHFFFAOYSA-N 0.000 claims 1
229910052783 alkali metal Inorganic materials 0.000 claims 1
150000001340 alkali metals Chemical class 0.000 claims 1
125000003710 aryl alkyl group Chemical group 0.000 claims 1
GSCLMSFRWBPUSK-UHFFFAOYSA-N beta-Butyrolactone Chemical compound CC1CC(=O)O1 GSCLMSFRWBPUSK-UHFFFAOYSA-N 0.000 claims 1
VEZXCJBBBCKRPI-UHFFFAOYSA-N beta-propiolactone Chemical compound O=C1CCO1 VEZXCJBBBCKRPI-UHFFFAOYSA-N 0.000 claims 1
125000005843 halogen group Chemical group 0.000 claims 1
230000000379 polymerizing effect Effects 0.000 abstract description 2
229960004279 formaldehyde Drugs 0.000 description 35
235000019256 formaldehyde Nutrition 0.000 description 35
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 33
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 24
239000000725 suspension Substances 0.000 description 16
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 15
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
239000000243 solution Substances 0.000 description 9
WXNZTHHGJRFXKQ-UHFFFAOYSA-N 4-chlorophenol Chemical compound OC1=CC=C(Cl)C=C1 WXNZTHHGJRFXKQ-UHFFFAOYSA-N 0.000 description 8
238000013019 agitation Methods 0.000 description 7
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
238000011282 treatment Methods 0.000 description 6
230000015556 catabolic process Effects 0.000 description 5
238000006731 degradation reaction Methods 0.000 description 5
YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 4
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
239000011952 anionic catalyst Substances 0.000 description 4
230000003197 catalytic effect Effects 0.000 description 4
150000002430 hydrocarbons Chemical group 0.000 description 4
238000002844 melting Methods 0.000 description 4
230000008018 melting Effects 0.000 description 4
238000001556 precipitation Methods 0.000 description 4
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
238000012694 Lactone Polymerization Methods 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
125000001931 aliphatic group Chemical group 0.000 description 3
229920001577 copolymer Polymers 0.000 description 3
230000032050 esterification Effects 0.000 description 3
238000005886 esterification reaction Methods 0.000 description 3
150000002500 ions Chemical class 0.000 description 3
238000004519 manufacturing process Methods 0.000 description 3
239000012299 nitrogen atmosphere Substances 0.000 description 3
229940090668 parachlorophenol Drugs 0.000 description 3
229960000380 propiolactone Drugs 0.000 description 3
238000000746 purification Methods 0.000 description 3
239000000126 substance Substances 0.000 description 3
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 2
229910052784 alkaline earth metal Inorganic materials 0.000 description 2
150000001408 amides Chemical class 0.000 description 2
239000012298 atmosphere Substances 0.000 description 2
235000019445 benzyl alcohol Nutrition 0.000 description 2
229930188620 butyrolactone Natural products 0.000 description 2
150000001735 carboxylic acids Chemical class 0.000 description 2
239000007810 chemical reaction solvent Substances 0.000 description 2
238000001035 drying Methods 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
238000006266 etherification reaction Methods 0.000 description 2
150000002170 ethers Chemical class 0.000 description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
239000002002 slurry Substances 0.000 description 2
239000003381 stabilizer Substances 0.000 description 2
GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 2
238000005406 washing Methods 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
GRWFGVWFFZKLTI-UHFFFAOYSA-N α-pinene Chemical compound CC1=CCC2C(C)(C)C1C2 GRWFGVWFFZKLTI-UHFFFAOYSA-N 0.000 description 2
ZQXCQTAELHSNAT-UHFFFAOYSA-N 1-chloro-3-nitro-5-(trifluoromethyl)benzene Chemical compound [O-][N+](=O)C1=CC(Cl)=CC(C(F)(F)F)=C1 ZQXCQTAELHSNAT-UHFFFAOYSA-N 0.000 description 1
GRWFGVWFFZKLTI-IUCAKERBSA-N 1S,5S-(-)-alpha-Pinene Natural products CC1=CC[C@@H]2C(C)(C)[C@H]1C2 GRWFGVWFFZKLTI-IUCAKERBSA-N 0.000 description 1
JTXMVXSTHSMVQF-UHFFFAOYSA-N 2-acetyloxyethyl acetate Chemical compound CC(=O)OCCOC(C)=O JTXMVXSTHSMVQF-UHFFFAOYSA-N 0.000 description 1
WJQOZHYUIDYNHM-UHFFFAOYSA-N 2-tert-Butylphenol Chemical compound CC(C)(C)C1=CC=CC=C1O WJQOZHYUIDYNHM-UHFFFAOYSA-N 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
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
239000005977 Ethylene Substances 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
229920002292 Nylon 6 Polymers 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
229910000831 Steel Inorganic materials 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
239000003513 alkali Substances 0.000 description 1
150000001342 alkaline earth metals Chemical class 0.000 description 1
125000002877 alkyl aryl group Chemical group 0.000 description 1
MVNCAPSFBDBCGF-UHFFFAOYSA-N alpha-pinene Natural products CC1=CCC23C1CC2C3(C)C MVNCAPSFBDBCGF-UHFFFAOYSA-N 0.000 description 1
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
TZIHFWKZFHZASV-UHFFFAOYSA-N anhydrous methyl formate Natural products COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 description 1
125000000129 anionic group Chemical group 0.000 description 1
229910052787 antimony Inorganic materials 0.000 description 1
WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical group [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 1
239000003963 antioxidant agent Substances 0.000 description 1
150000004982 aromatic amines Chemical class 0.000 description 1
RBFQJDQYXXHULB-UHFFFAOYSA-N arsane Chemical class [AsH3] RBFQJDQYXXHULB-UHFFFAOYSA-N 0.000 description 1
229910052785 arsenic Inorganic materials 0.000 description 1
RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical group [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 description 1
150000005840 aryl radicals Chemical class 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
VFTUVESODZZQIP-UHFFFAOYSA-N azepan-2-one;lithium Chemical compound [Li].O=C1CCCCCN1 VFTUVESODZZQIP-UHFFFAOYSA-N 0.000 description 1
230000000903 blocking effect Effects 0.000 description 1
238000000071 blow moulding Methods 0.000 description 1
229910052796 boron Inorganic materials 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
229960001701 chloroform Drugs 0.000 description 1
238000001816 cooling Methods 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
239000007857 degradation product Substances 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
230000009977 dual effect Effects 0.000 description 1
125000001033 ether group Chemical group 0.000 description 1
KIWBPDUYBMNFTB-UHFFFAOYSA-M ethyl sulfate Chemical compound CCOS([O-])(=O)=O KIWBPDUYBMNFTB-UHFFFAOYSA-M 0.000 description 1
238000001125 extrusion Methods 0.000 description 1
238000011010 flushing procedure Methods 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
239000008187 granular material Substances 0.000 description 1
125000001475 halogen functional group Chemical group 0.000 description 1
239000002638 heterogeneous catalyst Substances 0.000 description 1
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
239000002815 homogeneous catalyst Substances 0.000 description 1
150000002429 hydrazines Chemical class 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
150000002466 imines Chemical class 0.000 description 1
238000001746 injection moulding Methods 0.000 description 1
239000012948 isocyanate Substances 0.000 description 1
150000002513 isocyanates Chemical class 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
239000000463 material Substances 0.000 description 1
150000002739 metals Chemical class 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
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
239000002674 ointment Substances 0.000 description 1
239000012430 organic reaction media Substances 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
239000012188 paraffin wax Substances 0.000 description 1
150000002989 phenols Chemical class 0.000 description 1
150000003003 phosphines Chemical class 0.000 description 1
150000008039 phosphoramides Chemical class 0.000 description 1
239000004033 plastic Substances 0.000 description 1
229920003023 plastic Polymers 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
229920001610 polycaprolactone Polymers 0.000 description 1
239000004632 polycaprolactone Substances 0.000 description 1
229920006149 polyester-amide block copolymer Polymers 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
239000000047 product Substances 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
IOVGROKTTNBUGK-SJCJKPOMSA-N ritodrine Chemical compound N([C@@H](C)[C@H](O)C=1C=CC(O)=CC=1)CCC1=CC=C(O)C=C1 IOVGROKTTNBUGK-SJCJKPOMSA-N 0.000 description 1
238000001175 rotational moulding Methods 0.000 description 1
238000000926 separation method Methods 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
239000007787 solid Substances 0.000 description 1
238000009987 spinning Methods 0.000 description 1
230000006641 stabilisation Effects 0.000 description 1
238000011105 stabilization Methods 0.000 description 1
230000003068 static effect Effects 0.000 description 1
239000010959 steel Substances 0.000 description 1
OUULRIDHGPHMNQ-UHFFFAOYSA-N stibane Chemical class [SbH3] OUULRIDHGPHMNQ-UHFFFAOYSA-N 0.000 description 1
150000003462 sulfoxides Chemical class 0.000 description 1
FAQYAMRNWDIXMY-UHFFFAOYSA-N trichloroborane Chemical compound ClB(Cl)Cl FAQYAMRNWDIXMY-UHFFFAOYSA-N 0.000 description 1
JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
239000008096 xylene Substances 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
- C08G2/08—Polymerisation of formaldehyde
- 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
- C08G2/06—Catalysts

Landscapes

Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Medicinal Chemistry (AREA)
Polymers & Plastics (AREA)
Organic Chemistry (AREA)
Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
Polyesters Or Polycarbonates (AREA)

CA263,536A 1975-10-30 1976-10-15 Process for the polymerization of formaldehyde Expired CA1105187A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
IT28814-A/75		1975-10-30
IT2881475A IT1043748B (it)	1975-10-30	1975-10-30	Procedimente per la polimerizzazione della formaldeide

Publications (1)

Publication Number	Publication Date
CA1105187A true CA1105187A (en)	1981-07-14

Family

ID=11224240

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA263,536A Expired CA1105187A (en)	1975-10-30	1976-10-15	Process for the polymerization of formaldehyde

Country Status (5)

Country	Link
CA (1)	CA1105187A (it)
DE (1)	DE2649800C2 (it)
GB (1)	GB1522879A (it)
IT (1)	IT1043748B (it)
NL (1)	NL7612012A (it)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP4015555A1 (de)	2020-12-18	2022-06-22	Covestro Deutschland AG	Verfahren zur herstellung eines monols oder polyols umfassend einen polyoxymethylen-block
CN114133537B (zh) *	2021-12-10	2023-09-12	开滦（集团）有限责任公司	一种聚甲醛-聚己内酯共聚物及其制备方法

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
IT1006689B (it) *	1973-12-28	1976-10-20	Sir Soc Italiana Resine Spa	Procedimento per la polimerizza zione della formaldeide

1975
- 1975-10-30 IT IT2881475A patent/IT1043748B/it active
1976
- 1976-10-14 GB GB4275476A patent/GB1522879A/en not_active Expired
- 1976-10-15 CA CA263,536A patent/CA1105187A/en not_active Expired
- 1976-10-29 NL NL7612012A patent/NL7612012A/xx not_active Application Discontinuation
- 1976-10-29 DE DE19762649800 patent/DE2649800C2/de not_active Expired

Also Published As

Publication number	Publication date
DE2649800A1 (de)	1977-05-18
DE2649800C2 (de)	1985-08-14
IT1043748B (it)	1980-02-29
NL7612012A (nl)	1977-05-03
GB1522879A (en)	1978-08-31

Legal Events

Date	Code	Title	Description
1998-07-14	MKEX	Expiry

Publication	Publication Date	Title
US3979480A (en)	1976-09-07	Process for the polymerization of formaldehyde
EP0629644B1 (en)	1999-10-13	Process for the preparation of a polyoxymethylene terpolymer
CA2274377A1 (en)	2000-03-08	Process for the preparation of polyacetal copolymers
US3442864A (en)	1969-05-06	Formals of norbornane-2,7-diols and copolymers thereof with trioxane
EP0559496B1 (en)	1997-08-27	Process for producing polyoxymethylene copolymers
CA1105187A (en)	1981-07-14	Process for the polymerization of formaldehyde
US3979479A (en)	1976-09-07	Block copolymers
JP4610805B2 (ja)	2011-01-12	ポリアセタール共重合体の製造方法
US4111912A (en)	1978-09-05	Process for the manufacture of coarse-granular oxymethylene polymers
US3170896A (en)	1965-02-23	Process for acylating polyoxymethylenes
JPH0542961B2 (it)	1993-06-30
EP0994135B1 (en)	2002-09-18	Process for the preparation of thermally stable polyoxymethylene copolymers
CN116635441B (zh)	2026-02-03	聚缩醛共聚物及其制造方法
CA1054741A (en)	1979-05-15	Block copolymers
US5300690A (en)	1994-04-05	Polyoxime derived from carbon monoxide-propylene polyketone
US3168495A (en)	1965-02-02	Production of polyoxymethylenes from trioxane
CA1043037A (en)	1978-11-21	Stabilization of acetal polymers
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