DE2138309B2 - Stabilisierung waessriger formaldehydloesungen - Google Patents
Stabilisierung waessriger formaldehydloesungenInfo
- Publication number
- DE2138309B2 DE2138309B2 DE19712138309 DE2138309A DE2138309B2 DE 2138309 B2 DE2138309 B2 DE 2138309B2 DE 19712138309 DE19712138309 DE 19712138309 DE 2138309 A DE2138309 A DE 2138309A DE 2138309 B2 DE2138309 B2 DE 2138309B2
- Authority
- DE
- Germany
- Prior art keywords
- formaldehyde
- solutions
- methanol
- concentrations
- percent
- 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.)
- Withdrawn
Links
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 title claims description 114
- 230000006641 stabilisation Effects 0.000 title claims description 3
- 238000011105 stabilization Methods 0.000 title claims description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 46
- 239000003381 stabilizer Substances 0.000 claims description 20
- 229920000151 polyglycol Polymers 0.000 claims description 18
- 239000010695 polyglycol Substances 0.000 claims description 18
- 150000002170 ethers Chemical class 0.000 claims description 16
- 239000008098 formaldehyde solution Substances 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 7
- 150000003918 triazines Chemical class 0.000 claims description 7
- 239000000194 fatty acid Substances 0.000 claims description 6
- -1 polyoxyethylene lauryl ether Polymers 0.000 claims description 6
- 238000009833 condensation Methods 0.000 claims description 5
- 230000005494 condensation Effects 0.000 claims description 5
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 5
- 150000002148 esters Chemical class 0.000 claims description 5
- 229930195729 fatty acid Natural products 0.000 claims description 5
- OFAPSLLQSSHRSQ-UHFFFAOYSA-N 1H-triazine-2,4-diamine Chemical class NN1NC=CC(N)=N1 OFAPSLLQSSHRSQ-UHFFFAOYSA-N 0.000 claims description 4
- GZVHEAJQGPRDLQ-UHFFFAOYSA-N 6-phenyl-1,3,5-triazine-2,4-diamine Chemical compound NC1=NC(N)=NC(C=2C=CC=CC=2)=N1 GZVHEAJQGPRDLQ-UHFFFAOYSA-N 0.000 claims description 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 150000004665 fatty acids Chemical class 0.000 claims description 4
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 claims description 4
- 229920000877 Melamine resin Polymers 0.000 claims description 3
- 150000002191 fatty alcohols Chemical class 0.000 claims description 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 3
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 claims description 3
- 230000000087 stabilizing effect Effects 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- 229930040373 Paraformaldehyde Natural products 0.000 claims description 2
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 2
- 239000004202 carbamide Substances 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 claims description 2
- 239000007795 chemical reaction product Substances 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- 229920002866 paraformaldehyde Polymers 0.000 claims description 2
- 238000001556 precipitation Methods 0.000 claims description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims 5
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 claims 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims 4
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 claims 4
- 239000004372 Polyvinyl alcohol Substances 0.000 claims 4
- 150000001241 acetals Chemical class 0.000 claims 4
- 229920002451 polyvinyl alcohol Polymers 0.000 claims 4
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 claims 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims 3
- 239000000600 sorbitol Substances 0.000 claims 3
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 claims 2
- BBMCTIGTTCKYKF-UHFFFAOYSA-N 1-heptanol Chemical compound CCCCCCCO BBMCTIGTTCKYKF-UHFFFAOYSA-N 0.000 claims 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 2
- 239000002202 Polyethylene glycol Substances 0.000 claims 2
- 239000000084 colloidal system Substances 0.000 claims 2
- 238000006482 condensation reaction Methods 0.000 claims 2
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 claims 2
- 235000011187 glycerol Nutrition 0.000 claims 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 229920001223 polyethylene glycol Polymers 0.000 claims 2
- 150000005846 sugar alcohols Polymers 0.000 claims 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims 2
- LNAZSHAWQACDHT-XIYTZBAFSA-N (2r,3r,4s,5r,6s)-4,5-dimethoxy-2-(methoxymethyl)-3-[(2s,3r,4s,5r,6r)-3,4,5-trimethoxy-6-(methoxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6r)-4,5,6-trimethoxy-2-(methoxymethyl)oxan-3-yl]oxyoxane Chemical compound CO[C@@H]1[C@@H](OC)[C@H](OC)[C@@H](COC)O[C@H]1O[C@H]1[C@H](OC)[C@@H](OC)[C@H](O[C@H]2[C@@H]([C@@H](OC)[C@H](OC)O[C@@H]2COC)OC)O[C@@H]1COC LNAZSHAWQACDHT-XIYTZBAFSA-N 0.000 claims 1
- JIHOVGXINXMLLR-UHFFFAOYSA-N 2-n-phenyl-1,3,5-triazine-2,4,6-triamine Chemical compound NC1=NC(N)=NC(NC=2C=CC=CC=2)=N1 JIHOVGXINXMLLR-UHFFFAOYSA-N 0.000 claims 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 claims 1
- NGYGUYRBWLUDRP-UHFFFAOYSA-N 6-propyl-1,3,5-triazine-2,4-diamine Chemical compound CCCC1=NC(N)=NC(N)=N1 NGYGUYRBWLUDRP-UHFFFAOYSA-N 0.000 claims 1
- 239000001856 Ethyl cellulose Substances 0.000 claims 1
- ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 claims 1
- 108010010803 Gelatin Proteins 0.000 claims 1
- MGJKQDOBUOMPEZ-UHFFFAOYSA-N N,N'-dimethylurea Chemical compound CNC(=O)NC MGJKQDOBUOMPEZ-UHFFFAOYSA-N 0.000 claims 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 claims 1
- MBHRHUJRKGNOKX-UHFFFAOYSA-N [(4,6-diamino-1,3,5-triazin-2-yl)amino]methanol Chemical compound NC1=NC(N)=NC(NCO)=N1 MBHRHUJRKGNOKX-UHFFFAOYSA-N 0.000 claims 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims 1
- NJYZCEFQAIUHSD-UHFFFAOYSA-N acetoguanamine Chemical class CC1=NC(N)=NC(N)=N1 NJYZCEFQAIUHSD-UHFFFAOYSA-N 0.000 claims 1
- PXAJQJMDEXJWFB-UHFFFAOYSA-N acetone oxime Chemical compound CC(C)=NO PXAJQJMDEXJWFB-UHFFFAOYSA-N 0.000 claims 1
- 150000001298 alcohols Chemical class 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 239000001913 cellulose Substances 0.000 claims 1
- 235000010980 cellulose Nutrition 0.000 claims 1
- 229920002678 cellulose Polymers 0.000 claims 1
- 230000007797 corrosion Effects 0.000 claims 1
- 238000005260 corrosion Methods 0.000 claims 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 1
- 125000005745 ethoxymethyl group Chemical class [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 claims 1
- 235000019325 ethyl cellulose Nutrition 0.000 claims 1
- 229920001249 ethyl cellulose Polymers 0.000 claims 1
- 235000019253 formic acid Nutrition 0.000 claims 1
- 229920000159 gelatin Polymers 0.000 claims 1
- 239000008273 gelatin Substances 0.000 claims 1
- 235000019322 gelatine Nutrition 0.000 claims 1
- 235000011852 gelatine desserts Nutrition 0.000 claims 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims 1
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 claims 1
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 claims 1
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 claims 1
- UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 claims 1
- 125000004184 methoxymethyl group Chemical class [H]C([H])([H])OC([H])([H])* 0.000 claims 1
- 229920000609 methyl cellulose Polymers 0.000 claims 1
- 239000001923 methylcellulose Substances 0.000 claims 1
- 235000010981 methylcellulose Nutrition 0.000 claims 1
- 239000001814 pectin Substances 0.000 claims 1
- 235000010987 pectin Nutrition 0.000 claims 1
- 229920001277 pectin Polymers 0.000 claims 1
- 229920000259 polyoxyethylene lauryl ether Polymers 0.000 claims 1
- 229920001451 polypropylene glycol Polymers 0.000 claims 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims 1
- 125000005767 propoxymethyl group Chemical class [H]C([H])([H])C([H])([H])C([H])([H])[#8]C([H])([H])* 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 22
- 239000000243 solution Substances 0.000 description 18
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 8
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 7
- 229960000541 cetyl alcohol Drugs 0.000 description 4
- IUCCYXZWZMFVPE-UHFFFAOYSA-N 2,2-bis(hydroxymethyl)propane-1,3-diol;dodecanoic acid Chemical compound OCC(CO)(CO)CO.CCCCCCCCCCCC(O)=O IUCCYXZWZMFVPE-UHFFFAOYSA-N 0.000 description 3
- BDPPZSFVSOBOIX-UHFFFAOYSA-N 6-nonyl-1,3,5-triazine-2,4-diamine Chemical compound CCCCCCCCCC1=NC(N)=NC(N)=N1 BDPPZSFVSOBOIX-UHFFFAOYSA-N 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- ARWLNYJOVMFZNY-KVVVOXFISA-N 2,2-bis(hydroxymethyl)propane-1,3-diol;(z)-octadec-9-enoic acid Chemical compound OCC(CO)(CO)CO.CCCCCCCC\C=C/CCCCCCCC(O)=O ARWLNYJOVMFZNY-KVVVOXFISA-N 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000006735 deficit Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/78—Separation; Purification; Stabilisation; Use of additives
- C07C45/86—Use of additives, e.g. for stabilisation
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19712138309 DE2138309B2 (de) | 1971-07-30 | 1971-07-30 | Stabilisierung waessriger formaldehydloesungen |
| NL7207295A NL169168C (nl) | 1971-07-30 | 1972-05-30 | Werkwijze voor het stabiliseren van waterige formaldehyde-oplossingen. |
| CH806372A CH571467A5 (enExample) | 1971-07-30 | 1972-05-31 | |
| CS517972A CS175435B2 (enExample) | 1971-07-30 | 1972-07-20 | |
| AT647172A AT329528B (de) | 1971-07-30 | 1972-07-27 | Stabilisierte wasserige formaldehydlosungen |
| FR7227368A FR2148090A1 (en) | 1971-07-30 | 1972-07-28 | Stabilising aq formaldehyde solns - with 2,4-diamino-triazines (1 3 5) or its methylol derivs and hydrophilic polyglycol ethers of |
| BE786965A BE786965A (fr) | 1971-07-30 | 1972-07-28 | Stabilisation de solutions aqueuses de formaldehyde |
| IT5184672A IT961754B (it) | 1971-07-30 | 1972-07-28 | Soluzioni acquose di formaldeide stabilizzate |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19712138309 DE2138309B2 (de) | 1971-07-30 | 1971-07-30 | Stabilisierung waessriger formaldehydloesungen |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2138309A1 DE2138309A1 (de) | 1973-02-08 |
| DE2138309B2 true DE2138309B2 (de) | 1977-12-22 |
Family
ID=5815372
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19712138309 Withdrawn DE2138309B2 (de) | 1971-07-30 | 1971-07-30 | Stabilisierung waessriger formaldehydloesungen |
Country Status (8)
| Country | Link |
|---|---|
| AT (1) | AT329528B (enExample) |
| BE (1) | BE786965A (enExample) |
| CH (1) | CH571467A5 (enExample) |
| CS (1) | CS175435B2 (enExample) |
| DE (1) | DE2138309B2 (enExample) |
| FR (1) | FR2148090A1 (enExample) |
| IT (1) | IT961754B (enExample) |
| NL (1) | NL169168C (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2495135A1 (fr) * | 1980-12-02 | 1982-06-04 | Sir Soc Italiana Resine Spa | Solutions aqueuses concentrees et stables de formaldehyde et procede pour leur preparation |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1063642B (it) * | 1976-11-05 | 1985-02-11 | Montedison Spa | Processo per la stabilizzazione di soluzioni acquose di formaldeide |
| DE3143920A1 (de) * | 1981-11-05 | 1983-05-11 | Degussa Ag, 6000 Frankfurt | Neue bismelamine |
-
1971
- 1971-07-30 DE DE19712138309 patent/DE2138309B2/de not_active Withdrawn
-
1972
- 1972-05-30 NL NL7207295A patent/NL169168C/xx not_active IP Right Cessation
- 1972-05-31 CH CH806372A patent/CH571467A5/xx not_active IP Right Cessation
- 1972-07-20 CS CS517972A patent/CS175435B2/cs unknown
- 1972-07-27 AT AT647172A patent/AT329528B/de not_active IP Right Cessation
- 1972-07-28 FR FR7227368A patent/FR2148090A1/fr active Granted
- 1972-07-28 IT IT5184672A patent/IT961754B/it active
- 1972-07-28 BE BE786965A patent/BE786965A/xx unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2495135A1 (fr) * | 1980-12-02 | 1982-06-04 | Sir Soc Italiana Resine Spa | Solutions aqueuses concentrees et stables de formaldehyde et procede pour leur preparation |
Also Published As
| Publication number | Publication date |
|---|---|
| CS175435B2 (enExample) | 1977-05-31 |
| NL169168C (nl) | 1982-06-16 |
| ATA647172A (de) | 1975-08-15 |
| AT329528B (de) | 1976-05-10 |
| CH571467A5 (enExample) | 1976-01-15 |
| BE786965A (fr) | 1972-11-16 |
| IT961754B (it) | 1973-12-10 |
| NL169168B (nl) | 1982-01-18 |
| NL7207295A (enExample) | 1973-02-01 |
| FR2148090B1 (enExample) | 1976-08-13 |
| DE2138309A1 (de) | 1973-02-08 |
| FR2148090A1 (en) | 1973-03-11 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| BGA | New person/name/address of the applicant | ||
| 8239 | Disposal/non-payment of the annual fee |