DE1244410C2 - Verfahren zur Herstellung von vernetzbaren hochmolekularen Polymerisations-, Polykondensations- und Polyadditionsprodukten - Google Patents
Verfahren zur Herstellung von vernetzbaren hochmolekularen Polymerisations-, Polykondensations- und PolyadditionsproduktenInfo
- Publication number
 - DE1244410C2 DE1244410C2 DE1965F0045132 DEF0045132A DE1244410C2 DE 1244410 C2 DE1244410 C2 DE 1244410C2 DE 1965F0045132 DE1965F0045132 DE 1965F0045132 DE F0045132 A DEF0045132 A DE F0045132A DE 1244410 C2 DE1244410 C2 DE 1244410C2
 - Authority
 - DE
 - Germany
 - Prior art keywords
 - acid
 - weight
 - parts
 - isocyanate
 - molecular weight
 - 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 - Lifetime
 
Links
- 238000000034 method Methods 0.000 title claims description 38
 - 230000008569 process Effects 0.000 title claims description 19
 - 238000006068 polycondensation reaction Methods 0.000 title claims description 13
 - 238000004519 manufacturing process Methods 0.000 title claims description 7
 - -1 alkoxymethyl isocyanates Chemical class 0.000 claims description 38
 - 238000006243 chemical reaction Methods 0.000 claims description 31
 - 239000012948 isocyanate Substances 0.000 claims description 26
 - 238000006116 polymerization reaction Methods 0.000 claims description 11
 - 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
 - 150000005846 sugar alcohols Polymers 0.000 claims description 8
 - 229920000768 polyamine Polymers 0.000 claims description 7
 - 150000001414 amino alcohols Chemical class 0.000 claims description 3
 - CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 108
 - 239000000243 solution Substances 0.000 description 69
 - HTVHSOYSKFBUGY-UHFFFAOYSA-N isocyanato(methoxy)methane Chemical compound COCN=C=O HTVHSOYSKFBUGY-UHFFFAOYSA-N 0.000 description 54
 - 239000000047 product Substances 0.000 description 51
 - JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 46
 - ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 45
 - WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 42
 - 239000002253 acid Substances 0.000 description 38
 - 229920000728 polyester Polymers 0.000 description 32
 - LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 29
 - WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 24
 - 239000003054 catalyst Substances 0.000 description 24
 - 125000002887 hydroxy group Chemical group [H]O* 0.000 description 23
 - XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 23
 - 238000009833 condensation Methods 0.000 description 20
 - 230000005494 condensation Effects 0.000 description 20
 - XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 20
 - 239000011521 glass Substances 0.000 description 19
 - 239000000203 mixture Substances 0.000 description 17
 - NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 16
 - 150000007513 acids Chemical class 0.000 description 16
 - 238000010438 heat treatment Methods 0.000 description 16
 - XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
 - ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 15
 - 229920000570 polyether Polymers 0.000 description 15
 - 239000002904 solvent Substances 0.000 description 15
 - 238000009835 boiling Methods 0.000 description 14
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 - UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 13
 - 150000002513 isocyanates Chemical class 0.000 description 13
 - 239000001361 adipic acid Substances 0.000 description 12
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 - NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 12
 - 229920006324 polyoxymethylene Polymers 0.000 description 12
 - OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 11
 - 150000001298 alcohols Chemical class 0.000 description 11
 - 125000003368 amide group Chemical group 0.000 description 11
 - 150000001875 compounds Chemical class 0.000 description 11
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 - 229920005989 resin Polymers 0.000 description 11
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 - ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 10
 - 239000004721 Polyphenylene oxide Substances 0.000 description 10
 - 239000007795 chemical reaction product Substances 0.000 description 10
 - 229920001577 copolymer Polymers 0.000 description 10
 - 150000002605 large molecules Chemical class 0.000 description 10
 - RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
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 - WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 9
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 - QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
 - 229910000147 aluminium phosphate Inorganic materials 0.000 description 8
 - 230000003197 catalytic effect Effects 0.000 description 8
 - 239000007859 condensation product Substances 0.000 description 8
 - 238000004132 cross linking Methods 0.000 description 8
 - 239000007858 starting material Substances 0.000 description 8
 - RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 7
 - NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 7
 - 239000004593 Epoxy Substances 0.000 description 7
 - WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 7
 - 229910052751 metal Chemical class 0.000 description 7
 - 239000002184 metal Chemical class 0.000 description 7
 - 239000003960 organic solvent Substances 0.000 description 7
 - 239000004814 polyurethane Substances 0.000 description 7
 - 229920002635 polyurethane Polymers 0.000 description 7
 - IUTCEZPPWBHGIX-UHFFFAOYSA-N tin(2+) Chemical class [Sn+2] IUTCEZPPWBHGIX-UHFFFAOYSA-N 0.000 description 7
 - XVUXMGOWXURWBB-UHFFFAOYSA-N 1-(isocyanatomethoxy)-2-methylpropane Chemical compound CC(C)COCN=C=O XVUXMGOWXURWBB-UHFFFAOYSA-N 0.000 description 6
 - HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 6
 - OBETXYAYXDNJHR-UHFFFAOYSA-N 2-Ethylhexanoic acid Chemical compound CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 6
 - 239000004952 Polyamide Substances 0.000 description 6
 - ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 6
 - DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
 - PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 6
 - YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
 - 230000002378 acidificating effect Effects 0.000 description 6
 - 125000003277 amino group Chemical group 0.000 description 6
 - 235000013877 carbamide Nutrition 0.000 description 6
 - 150000004985 diamines Chemical class 0.000 description 6
 - MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
 - XLLIQLLCWZCATF-UHFFFAOYSA-N ethylene glycol monomethyl ether acetate Natural products COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 description 6
 - ACCCMOQWYVYDOT-UHFFFAOYSA-N hexane-1,1-diol Chemical compound CCCCCC(O)O ACCCMOQWYVYDOT-UHFFFAOYSA-N 0.000 description 6
 - FTVSQMOUCKBLDZ-UHFFFAOYSA-N isocyanatomethoxyethane Chemical compound CCOCN=C=O FTVSQMOUCKBLDZ-UHFFFAOYSA-N 0.000 description 6
 - VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 6
 - 229910052757 nitrogen Inorganic materials 0.000 description 6
 - 229920002647 polyamide Polymers 0.000 description 6
 - 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 6
 - GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 6
 - 238000003756 stirring Methods 0.000 description 6
 - 239000000126 substance Substances 0.000 description 6
 - ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 6
 - NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 5
 - IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 5
 - PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 5
 - CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 5
 - CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 5
 - 239000004202 carbamide Substances 0.000 description 5
 - 239000005018 casein Substances 0.000 description 5
 - BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 5
 - 235000021240 caseins Nutrition 0.000 description 5
 - XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 5
 - 239000000155 melt Substances 0.000 description 5
 - WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 5
 - 229920006295 polythiol Polymers 0.000 description 5
 - 239000011541 reaction mixture Substances 0.000 description 5
 - JRKRAGCSCGZLEI-UHFFFAOYSA-N 1-(isocyanatomethoxy)butane Chemical compound CCCCOCN=C=O JRKRAGCSCGZLEI-UHFFFAOYSA-N 0.000 description 4
 - HCRSNPPXQMGRPS-UHFFFAOYSA-N 1-(isocyanatomethoxy)propane Chemical compound CCCOCN=C=O HCRSNPPXQMGRPS-UHFFFAOYSA-N 0.000 description 4
 - KZJRJEIKWUJAKL-UHFFFAOYSA-N 2-(isocyanatomethoxy)propane Chemical compound C(C)(C)OCN=C=O KZJRJEIKWUJAKL-UHFFFAOYSA-N 0.000 description 4
 - PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
 - 108010010803 Gelatin Proteins 0.000 description 4
 - OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 4
 - VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
 - WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
 - SMEGJBVQLJJKKX-HOTMZDKISA-N [(2R,3S,4S,5R,6R)-5-acetyloxy-3,4,6-trihydroxyoxan-2-yl]methyl acetate Chemical group CC(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)O)OC(=O)C)O)O SMEGJBVQLJJKKX-HOTMZDKISA-N 0.000 description 4
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 - 230000009471 action Effects 0.000 description 4
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 - 150000001408 amides Chemical class 0.000 description 4
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 - 239000007864 aqueous solution Substances 0.000 description 4
 - IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 4
 - 229920002301 cellulose acetate Polymers 0.000 description 4
 - MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
 - XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 description 4
 - 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
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 - 235000011852 gelatine desserts Nutrition 0.000 description 4
 - FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 4
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 - 239000005056 polyisocyanate Substances 0.000 description 4
 - 150000008442 polyphenolic compounds Chemical class 0.000 description 4
 - 235000013824 polyphenols Nutrition 0.000 description 4
 - UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
 - KSBAEPSJVUENNK-UHFFFAOYSA-L tin(ii) 2-ethylhexanoate Chemical compound [Sn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O KSBAEPSJVUENNK-UHFFFAOYSA-L 0.000 description 4
 - VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 4
 - 238000005809 transesterification reaction Methods 0.000 description 4
 - IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 4
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 - 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 2
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 - YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
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 - KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
 - FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 2
 - LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical group COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
 - VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
 - 239000005977 Ethylene Substances 0.000 description 2
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 - C08G18/71—Monoisocyanates or monoisothiocyanates
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- 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
 - C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
 - C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
 - C08G73/08—Polyhydrazides; Polytriazoles; Polyaminotriazoles; Polyoxadiazoles
 
 - 
        
- 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
 - C08G75/00—Macromolecular compounds obtained by reactions forming a linkage containing sulfur with or without nitrogen, oxygen, or carbon in the main chain of the macromolecule
 
 - 
        
- 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
 - C08G75/00—Macromolecular compounds obtained by reactions forming a linkage containing sulfur with or without nitrogen, oxygen, or carbon in the main chain of the macromolecule
 - C08G75/30—Polysulfonamides; Polysulfonimides
 
 - 
        
- 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
 - C08G85/00—General processes for preparing compounds provided for in this subclass
 - C08G85/004—Modification of polymers by chemical after-treatment
 
 - 
        
- C—CHEMISTRY; METALLURGY
 - C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
 - C08H—DERIVATIVES OF NATURAL MACROMOLECULAR COMPOUNDS
 - C08H1/00—Macromolecular products derived from proteins
 
 - 
        
- C—CHEMISTRY; METALLURGY
 - C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
 - C08H—DERIVATIVES OF NATURAL MACROMOLECULAR COMPOUNDS
 - C08H1/00—Macromolecular products derived from proteins
 - C08H1/06—Macromolecular products derived from proteins derived from horn, hoofs, hair, skin or leather
 
 - 
        
- 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
 - C08J5/18—Manufacture of films or sheets
 
 - 
        
- C—CHEMISTRY; METALLURGY
 - C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
 - C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
 - C08L89/00—Compositions of proteins; Compositions of derivatives thereof
 - C08L89/005—Casein
 
 - 
        
- C—CHEMISTRY; METALLURGY
 - C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
 - C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
 - C08L89/00—Compositions of proteins; Compositions of derivatives thereof
 - C08L89/04—Products derived from waste materials, e.g. horn, hoof or hair
 - C08L89/06—Products derived from waste materials, e.g. horn, hoof or hair derived from leather or skin, e.g. gelatin
 
 - 
        
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
 - Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
 - Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
 - Y10S525/00—Synthetic resins or natural rubbers -- part of the class 520 series
 - Y10S525/911—Polymer from ethylenic monomers only, having terminal functional group other than unsaturation
 
 - 
        
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
 - Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
 - Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
 - Y10S528/00—Synthetic resins or natural rubbers -- part of the class 520 series
 - Y10S528/903—Polymerizing or processing an isocyanate under substantially anhydrous conditions
 
 
Landscapes
- Chemical & Material Sciences (AREA)
 - Health & Medical Sciences (AREA)
 - Organic Chemistry (AREA)
 - Chemical Kinetics & Catalysis (AREA)
 - Medicinal Chemistry (AREA)
 - Polymers & Plastics (AREA)
 - Engineering & Computer Science (AREA)
 - General Chemical & Material Sciences (AREA)
 - Materials Engineering (AREA)
 - Life Sciences & Earth Sciences (AREA)
 - Biochemistry (AREA)
 - Manufacturing & Machinery (AREA)
 - Dermatology (AREA)
 - Polyurethanes Or Polyureas (AREA)
 - Air-Flow Control Members (AREA)
 - Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
 
Priority Applications (11)
| Application Number | Priority Date | Filing Date | Title | 
|---|---|---|---|
| DE1965F0045132 DE1244410C2 (de) | 1965-02-03 | 1965-02-03 | Verfahren zur Herstellung von vernetzbaren hochmolekularen Polymerisations-, Polykondensations- und Polyadditionsprodukten | 
| SE101766A SE313441C (sv) | 1965-02-03 | 1966-01-26 | Rymdförnätningsbara, högmolekylära polymerisations-, polykondensations- och polyadditionsprodukter samt sätt att framställa sådana produkter | 
| AT71566A AT267181B (de) | 1965-02-03 | 1966-01-26 | Verfahren zur Herstellung von vernetzbaren hochmolekularen Polymerisations-, Polykondensations- und Polyadditionsprodukten | 
| CH1041269A CH491167A (de) | 1965-02-03 | 1966-01-26 | Verfahren zur Herstellung von vernetzbaren Polymeren | 
| CH102766A CH478877A (de) | 1965-02-03 | 1966-01-26 | Verfahren zur Herstellung von vernetzbaren Polymeren | 
| GB3770/66A GB1139422A (en) | 1965-02-03 | 1966-01-27 | A process for the production of cross-linkable high molecular weight reaction products of isocyanates | 
| BE675926D BE675926A (enEXAMPLES) | 1965-02-03 | 1966-02-02 | |
| US524467A US3480591A (en) | 1965-02-03 | 1966-02-02 | Polymers containing n-alkoxymethyl groups | 
| FR48153A FR1466892A (fr) | 1965-02-03 | 1966-02-02 | Procédé de préparation de produits de polymérisation, de polycondensation, de polyaddition, réticulables | 
| NO161535A NO125099B (enEXAMPLES) | 1965-02-03 | 1966-02-02 | |
| NL666601400A NL149199B (nl) | 1965-02-03 | 1966-02-03 | Werkwijze voor het bereiden van een verknoopbaar macromoleculair polymerisatieprodukt, alsmede daarmee verkregen gevormd voortbrengsel. | 
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title | 
|---|---|---|---|
| DE1965F0045132 DE1244410C2 (de) | 1965-02-03 | 1965-02-03 | Verfahren zur Herstellung von vernetzbaren hochmolekularen Polymerisations-, Polykondensations- und Polyadditionsprodukten | 
Publications (2)
| Publication Number | Publication Date | 
|---|---|
| DE1244410B DE1244410B (de) | 1967-07-13 | 
| DE1244410C2 true DE1244410C2 (de) | 1968-01-18 | 
Family
ID=7100352
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date | 
|---|---|---|---|
| DE1965F0045132 Expired - Lifetime DE1244410C2 (de) | 1965-02-03 | 1965-02-03 | Verfahren zur Herstellung von vernetzbaren hochmolekularen Polymerisations-, Polykondensations- und Polyadditionsprodukten | 
Country Status (10)
| Country | Link | 
|---|---|
| US (1) | US3480591A (enEXAMPLES) | 
| AT (1) | AT267181B (enEXAMPLES) | 
| BE (1) | BE675926A (enEXAMPLES) | 
| CH (2) | CH491167A (enEXAMPLES) | 
| DE (1) | DE1244410C2 (enEXAMPLES) | 
| FR (1) | FR1466892A (enEXAMPLES) | 
| GB (1) | GB1139422A (enEXAMPLES) | 
| NL (1) | NL149199B (enEXAMPLES) | 
| NO (1) | NO125099B (enEXAMPLES) | 
| SE (1) | SE313441C (enEXAMPLES) | 
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title | 
|---|---|---|---|---|
| DE1644810A1 (de) * | 1967-09-07 | 1971-01-21 | Bayer Ag | UEberzugsmittel und Lacke | 
| DE1794221A1 (de) * | 1968-09-25 | 1972-01-13 | Bayer Ag | Verfahren zum Veredeln von Fasermaterialien | 
| DE2003415C3 (de) * | 1970-01-27 | 1978-05-11 | Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung von als Bindemittel für Pulverlacke geeigneten vernetzbaren Lackharzen | 
| DE2943469A1 (de) * | 1979-10-27 | 1981-05-07 | Bayer Ag | Pulverfoermige beschichtungsmaterialien | 
| US4397707A (en) * | 1982-01-20 | 1983-08-09 | Lord Corporation | Compositions and methods for improving adhesion to plastic substrates | 
| DE3334996A1 (de) * | 1983-09-28 | 1985-04-18 | Schering AG, 1000 Berlin und 4709 Bergkamen | Verfahren zur herstellung von einbrennlacken auf basis von acrylat- und alkydharzen unter mitverwendung modifizierter epoxidharze | 
| EP0295031A3 (en) * | 1987-06-12 | 1991-05-08 | SMITH & NEPHEW plc | Orthopaedic splinting material | 
| NZ250375A (en) * | 1992-12-09 | 1995-07-26 | Ortho Pharma Corp | Peg hydrazone and peg oxime linkage forming reagents and protein derivatives | 
| DE4492364T1 (de) * | 1993-04-20 | 1995-05-11 | Dainippon Ink & Chemicals | Härtbare Masse und Verfahren zur Bildung eines Films unter Verwendung derselben | 
| DE10305119B4 (de) * | 2003-02-07 | 2007-02-22 | Basf Coatings Ag | Beschichtungsstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung | 
| JP5321721B2 (ja) * | 2011-08-19 | 2013-10-23 | 富士ゼロックス株式会社 | 樹脂材料 | 
| CN115845818B (zh) * | 2022-12-13 | 2024-02-23 | 南京工业大学 | 一种木质素接枝n-[(二甲氨基)亚甲基]硫脲型重金属吸附剂及其制备方法与应用 | 
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title | 
|---|---|---|---|---|
| US2340757A (en) * | 1935-05-02 | 1944-02-01 | Heberlein Patent Corp | Isocyanates and related substances and process for their manufacture | 
| DE918777C (de) * | 1940-06-11 | 1954-10-04 | Bayer Ag | Verfahren zur Herstellung von Kondensationsprodukten | 
| US2466404A (en) * | 1944-03-08 | 1949-04-05 | Eastman Kodak Co | Polyvinyl carbamates | 
| US2592263A (en) * | 1947-08-13 | 1952-04-08 | Eastman Kodak Co | Method of reacting gelatin with naphthyl isocyanates and resulting products | 
| US2626278A (en) * | 1950-04-22 | 1953-01-20 | American Cyanamid Co | Method of preparing acyloxyethyl isocyanates | 
| US3205284A (en) * | 1960-07-20 | 1965-09-07 | Goodrich Co B F | Polymeric polyesters terminated with organic carbamate groups | 
| GB971607A (en) * | 1961-10-25 | 1964-09-30 | Grace W R & Co | Polymer products and preparation thereof | 
| DE1189544B (de) * | 1963-06-05 | 1965-03-25 | Bayer Ag | Verfahren zur Herstellung von Monoisocyanaten | 
| DE1205087B (de) * | 1964-02-26 | 1965-11-18 | Bayer Ag | Verfahren zur Herstellung von organischen Isocyanaten | 
- 
        1965
        
- 1965-02-03 DE DE1965F0045132 patent/DE1244410C2/de not_active Expired - Lifetime
 
 - 
        1966
        
- 1966-01-26 CH CH1041269A patent/CH491167A/de not_active IP Right Cessation
 - 1966-01-26 CH CH102766A patent/CH478877A/de not_active IP Right Cessation
 - 1966-01-26 SE SE101766A patent/SE313441C/xx unknown
 - 1966-01-26 AT AT71566A patent/AT267181B/de active
 - 1966-01-27 GB GB3770/66A patent/GB1139422A/en not_active Expired - Lifetime
 - 1966-02-02 US US524467A patent/US3480591A/en not_active Expired - Lifetime
 - 1966-02-02 FR FR48153A patent/FR1466892A/fr not_active Expired
 - 1966-02-02 BE BE675926D patent/BE675926A/xx unknown
 - 1966-02-02 NO NO161535A patent/NO125099B/no unknown
 - 1966-02-03 NL NL666601400A patent/NL149199B/xx unknown
 
 
Also Published As
| Publication number | Publication date | 
|---|---|
| AT267181B (de) | 1968-12-10 | 
| DE1244410B (de) | 1967-07-13 | 
| FR1466892A (fr) | 1967-01-20 | 
| NO125099B (enEXAMPLES) | 1972-07-17 | 
| NL6601400A (enEXAMPLES) | 1966-08-04 | 
| GB1139422A (en) | 1969-01-08 | 
| BE675926A (enEXAMPLES) | 1966-06-16 | 
| NL149199B (nl) | 1976-04-15 | 
| SE313441C (sv) | 1973-06-18 | 
| US3480591A (en) | 1969-11-25 | 
| CH478877A (de) | 1969-09-30 | 
| SE313441B (sv) | 1969-08-11 | 
| CH491167A (de) | 1970-05-31 | 
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Legal Events
| Date | Code | Title | Description | 
|---|---|---|---|
| E77 | Valid patent as to the heymanns-index 1977 | ||
| 8339 | Ceased/non-payment of the annual fee |