GB1489588A - Wet-strength resins and processes for making and using same - Google Patents
Wet-strength resins and processes for making and using sameInfo
- Publication number
- GB1489588A GB1489588A GB48043/74A GB4804374A GB1489588A GB 1489588 A GB1489588 A GB 1489588A GB 48043/74 A GB48043/74 A GB 48043/74A GB 4804374 A GB4804374 A GB 4804374A GB 1489588 A GB1489588 A GB 1489588A
- Authority
- GB
- United Kingdom
- Prior art keywords
- polyureide
- epihalohydrin
- reaction
- urea
- formaldehyde
- 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
- 229920005989 resin Polymers 0.000 title abstract 7
- 239000011347 resin Substances 0.000 title abstract 7
- 238000000034 method Methods 0.000 title abstract 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N formaldehyde Substances O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 abstract 12
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 abstract 5
- 239000004202 carbamide Substances 0.000 abstract 5
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 abstract 3
- 239000000243 solution Substances 0.000 abstract 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 abstract 2
- 238000009833 condensation Methods 0.000 abstract 2
- 230000005494 condensation Effects 0.000 abstract 2
- 239000012530 fluid Substances 0.000 abstract 2
- 229920001281 polyalkylene Polymers 0.000 abstract 2
- 238000010791 quenching Methods 0.000 abstract 2
- 230000000171 quenching effect Effects 0.000 abstract 2
- 150000005846 sugar alcohols Chemical class 0.000 abstract 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 abstract 1
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 abstract 1
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 abstract 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 1
- 239000004952 Polyamide Substances 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 239000000654 additive Substances 0.000 abstract 1
- 239000003513 alkali Substances 0.000 abstract 1
- 125000002947 alkylene group Chemical group 0.000 abstract 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 abstract 1
- 150000008064 anhydrides Chemical class 0.000 abstract 1
- -1 aqueous HCHO Chemical class 0.000 abstract 1
- 125000002091 cationic group Chemical group 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 238000010790 dilution Methods 0.000 abstract 1
- 239000012895 dilution Substances 0.000 abstract 1
- 238000001879 gelation Methods 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 229910052500 inorganic mineral Inorganic materials 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 abstract 1
- 239000011707 mineral Substances 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 229920002647 polyamide Polymers 0.000 abstract 1
- 229920000768 polyamine Polymers 0.000 abstract 1
- 229920005862 polyol Polymers 0.000 abstract 1
- 150000003077 polyols Chemical class 0.000 abstract 1
- 235000021309 simple sugar Nutrition 0.000 abstract 1
- 239000006188 syrup Substances 0.000 abstract 1
- 235000020357 syrup Nutrition 0.000 abstract 1
- 229920001187 thermosetting polymer Polymers 0.000 abstract 1
- 229960001124 trientine Drugs 0.000 abstract 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
- C08G12/00—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen
- C08G12/46—Block or graft polymers prepared by polycondensation of aldehydes or ketones on to macromolecular compounds
-
- D—TEXTILES; PAPER
- D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
- D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
- D21H17/00—Non-fibrous material added to the pulp, characterised by its constitution; Paper-impregnating material characterised by its constitution
- D21H17/20—Macromolecular organic compounds
- D21H17/33—Synthetic macromolecular compounds
- D21H17/46—Synthetic macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- D21H17/47—Condensation polymers of aldehydes or ketones
- D21H17/49—Condensation polymers of aldehydes or ketones with compounds containing hydrogen bound to nitrogen
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Phenolic Resins Or Amino Resins (AREA)
- Paper (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Polyurethanes Or Polyureas (AREA)
Abstract
1489588 Polyureide-epihalohydrin-formaldehyde resins SCOTT PAPER CO 6 Nov 1974 [12 Nov 1973] 48032/74 Heading C3R [Also in Division D2] A process for preparing a water-soluble cationic thermosetting polyureide - epihalohydrin-formaldehyde resin condensate comprises reacting at least one polyalkylene polyamine, having the general formula where R is a C 2 -C 8 alkylene group and n = 2-5, with a urea to form a polyureide, quenching the polyureide-forming reaction and then either reacting the polyureide with an epihalohydrin and then with formaldehyde, or reacting the polyureide first with formaldehyde and then with an epihalohydrin. The polyureide forming reaction may be quenched with water or preferably an organic hydroxyl-containing compound, e.g. aqueous HCHO, an aliphatic alcohol or polyol, simple sugars and sugar alcohols and anhydrides of sugar alcohols. The mole ratio of polyalkylene polyamide to urea is preferably from 0À1-1À0; the mole ratio of epihalohydrin to urea is preferably from 0À018-0À3; and the mole ratio of HCHO to urea is preferably from 1À0-3À0. The polyureide forming reaction is preferably carried out at atmospheric pressures by heating up to a temperature of 110-180 C. over a period of 1-4 hours and held at this temperature for 15 min. to 1 hour. The reaction with formaldehyde is generally a 2-stage reaction comprising: (A) methylolation of the polyureide-epihalohydrin intermediate at 65- 85 C. and at a pH of from 8-9À5 from 10-100 min.; and (B) condensation at 65-100 C. at a pH of from 4À5-7À0 for 30-120 min. A mineral acid, e.g. phosphoric acid, may be used to lower the pH for the condensation stage which stage is usually conducted until the solution of the resin condensate becomes a viscous syrup at the point of incipient gelation, at which time the reaction is terminated by dilution with water, aqueous HCHO or an alcohol and the pH is adjusted to form 6À0-7À0 with alkali, if necessary. In the examples resins are prepared as above by reacting a 2 : 1 mixture of triethylene tetramine and diethylenetriamine with urea, then quenching the reaction with ethylene glycol or water, and then reacting the quenched polyuriede either first with epichlorohydrin and then with HCHO or vice versa. The aqueous resin solutions produced are added to aqueous dye solutions to give printing fluids. Uses.-Wet-strength additives in papermaking processes; the resin component in aqueous printing fluids.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US00414649A US3839291A (en) | 1969-10-14 | 1973-11-12 | Wet-strength resins and processes for making and using same |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1489588A true GB1489588A (en) | 1977-10-19 |
Family
ID=23642339
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB48043/74A Expired GB1489588A (en) | 1973-11-12 | 1974-11-06 | Wet-strength resins and processes for making and using same |
Country Status (4)
| Country | Link |
|---|---|
| JP (1) | JPS5321711B2 (en) |
| CA (1) | CA1025589A (en) |
| DE (1) | DE2453826A1 (en) |
| GB (1) | GB1489588A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4452606A (en) * | 1981-05-14 | 1984-06-05 | Sandoz Ltd. | Compositions useful for improving the fastness of dyeings on cellulosic substrates: precondensates of N-methylol compound with polyalkylene polyamine-epihalohydrin product |
-
1974
- 1974-11-06 GB GB48043/74A patent/GB1489588A/en not_active Expired
- 1974-11-08 CA CA213,339A patent/CA1025589A/en not_active Expired
- 1974-11-11 DE DE19742453826 patent/DE2453826A1/en active Pending
- 1974-11-11 JP JP12982474A patent/JPS5321711B2/ja not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4452606A (en) * | 1981-05-14 | 1984-06-05 | Sandoz Ltd. | Compositions useful for improving the fastness of dyeings on cellulosic substrates: precondensates of N-methylol compound with polyalkylene polyamine-epihalohydrin product |
Also Published As
| Publication number | Publication date |
|---|---|
| DE2453826A1 (en) | 1975-05-15 |
| JPS50112486A (en) | 1975-09-03 |
| CA1025589A (en) | 1978-01-31 |
| AU7520174A (en) | 1976-05-13 |
| JPS5321711B2 (en) | 1978-07-04 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| 732 | Registration of transactions, instruments or events in the register (sect. 32/1977) | ||
| PCNP | Patent ceased through non-payment of renewal fee |