GB601983A - Manufacture of aminotriazine-aldehyde reaction products - Google Patents

Manufacture of aminotriazine-aldehyde reaction products

Info

Publication number
GB601983A
GB601983A GB11239/45A GB1123945A GB601983A GB 601983 A GB601983 A GB 601983A GB 11239/45 A GB11239/45 A GB 11239/45A GB 1123945 A GB1123945 A GB 1123945A GB 601983 A GB601983 A GB 601983A
Authority
GB
United Kingdom
Prior art keywords
triazine
water
aldehyde
reaction
clear solution
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
Application number
GB11239/45A
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.)
Monsanto Chemicals Ltd
Monsanto Chemical Co
Original Assignee
Monsanto Chemicals Ltd
Monsanto Chemical Co
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.)
Filing date
Publication date
Application filed by Monsanto Chemicals Ltd, Monsanto Chemical Co filed Critical Monsanto Chemicals Ltd
Publication of GB601983A publication Critical patent/GB601983A/en
Expired legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G12/00Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen
    • C08G12/02Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes
    • C08G12/26Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with heterocyclic compounds
    • C08G12/263Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with heterocyclic compounds with at least two compounds covered by more than one of the groups C08G12/28 - C08G12/32
    • C08G12/266Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with heterocyclic compounds with at least two compounds covered by more than one of the groups C08G12/28 - C08G12/32 one being melamine
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G12/00Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen
    • C08G12/02Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes
    • C08G12/26Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with heterocyclic compounds
    • C08G12/30Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with heterocyclic compounds with substituted triazines

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Phenolic Resins Or Amino Resins (AREA)

Abstract

Solid aminotriazine-aldehyde condensation products, soluble in all proportions in water at ordinary temperature, are formed by reacting an aqueous mixture of an aminotriazine and a water-soluble aldehyde to form a clear solution capable of unlimited dilution with water without precipitation, dehydrating the solution so rapidly that the dry product has unlimited solubility in water and immediately cooling the dry product to 80 DEG C. or lower. Preferably the solution is spray dried but it may be dried on a drum preferably in vacuo. The reaction mixture is preferably kept alkaline. Suitable aminotriazines are melamine, ammeline, ammelide, 2, 4, 6,triethyl- or triphenyl-triamino-1, 3, 5-triazine; 2, 4, 6-trihydrazino-1, 3, 5-triazine; melam; melem; 2-amino-1, 3, 5-triazine; 2-chloro-4,6-diamino-1,3,5-triazine; 2 - phenyl - 4 - amino - 6 - hydroxy-1,3,5-triazine; and 6-methyl-2,4-diamino-1,3,5-triazine or mixtures thereof. Suitable aldehydes are formaldehyde, acetaldehyde, propionaldehyde, glycollic aldehyde, glyoxylic aldehyde, crotonaldehyde, acrolein, tiglic aldehyde, chloral, or glyoxal. The clear solution is preferably kept above crystallisation temperature before drying or it may be diluted to prevent crystallisation. Four examples describe the preparation of melamine formaldehyde condensation products with varying initial proportions of the reactants and of water. Example 5 describes the preparation of a condensation product from ammeline and formaldehyde. A continuous method of operation is described which avoids the difficulty when drying large patches of material that the last portions stand longer before drying than the first ones. In the method described predetermined quantities of reactants are fed to a reaction kettle, the pH of the mixture is adjusted and the reaction allowed to proceed. The clear solution is then filtered without being allowed to crystallise, stored and then continuously passed to a spray drier, the dried product cooled below 80 DEG C. passed to a powder recovery process and continuously removed and packed. At an appropriate time after starting a reaction in one kettle, a reaction is started in a second kettle so that a continuous supply of clear solution is available for drying. In a modification the reaction mixture may flow continuously through a reactor the temperature and length of which are related to produce a product which can pass immediately to the dryer. Aqueous solutions of the products are suitable for coating or impregnating, as adhesives or as intermediates for preparing etherified resins. Acidic or basic hardening agents may be added to the products. Plasticizers, colouring matters or other resins may also be added. Mixtures with hydroxylated vinyl resins containing sufficient OH groups to be self-dispersible in water are particularly useful. Specification 574,016 is referred to.ALSO:Solid aminotriazine-aldehyde condensation products, soluble in all proportions in water at ordinary temperature are formed by reacting an aqueous mixture of an aminotriazine and a water-soluble aldehyde to form a clear solution capable of unlimited dilution with water without precipitation, dehydrating the solution so rapidly that the dry product has unlimited solubility in water and immediately cooling the dry product to 80 DEG C. or lower. Preferably, the solution is spray dried, but it may be dried in a drum, preferably in vacuo. The reaction mixture is preferably kept alkaline. Suitable aminotriazines are melamine, ammeline, ammelide, 2,4,6-triethyl- or triphenyl-triamino-1,3,5-triazine; 2,4,6-trihydrazine-1,3,5-triazine; melam; melem; 2-amino-1,3,5-triazine; 2-chloro-4,6-diamino-1,3,5-triazine; 2-phenyl-4-amino-6-hydroxy-1,3,5-triazine; and 6-methyl-2,4-diamino-1,3,5-triazine or mixtures thereof. Suitable aldehydes are formaldehyde, acetaldehyde, propionaldehyde, glycollic aldehyde, glyoxylic aldehyde, crotonaldehyde, acrolein, lighter aldehyde, chloral or glyoxal. The clear solution is preferably kept above crystallization temperature before drying or it may be diluted to prevent crystallization. Four examples describe the preparation of melamino-formaldehyde condensation products with varying initial proportions of the reactants and of water. Example 5 describes the preparation of a condensation product from ammeline and formaldehyde. A continuous method of operation is described which avoids the difficulty when drying large batches of material that the last portions stand longer before drying than the first ones. In the method described, predetermined quantities of reactants are fed to a reaction kettle, the pH of the mixture is adjusted and the reaction allowed to proceed. The clear solution is then filtered without being allowed to crystallize, stored and then continuously passed to a spray drier, the dried product cooled below 80 DEG C. passed to a powder recovery process and continuously removed and packed. At an appropriate time after starting a reaction in one kettle, a reaction is started in a second kettle so that a continuous supply of clear solution is available for drying. In a modification, the reaction mixture may flow continuously through a reactor, the temperature and length of which are related to produce a product which can pass immediately to the dryer. Aqueous solutions of the products are suitable for coating or impregnating, as adhesives or as intermediates for preparing etherified resins. Acidic or basic hardening agents may be added to the products. Plasticisers, colouring matters or other resins may also be added. Mixtures with hydroxylated vinyl resins containing sufficient OH groups to be self-dispersible in water are particularly useful. Specification 574,016 is referred to.
GB11239/45A 1944-05-06 1945-05-03 Manufacture of aminotriazine-aldehyde reaction products Expired GB601983A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US601983XA 1944-05-06 1944-05-06

Publications (1)

Publication Number Publication Date
GB601983A true GB601983A (en) 1948-05-18

Family

ID=22027979

Family Applications (1)

Application Number Title Priority Date Filing Date
GB11239/45A Expired GB601983A (en) 1944-05-06 1945-05-03 Manufacture of aminotriazine-aldehyde reaction products

Country Status (1)

Country Link
GB (1) GB601983A (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1015438B (en) * 1953-11-30 1957-09-12 British Oxygen Co Ltd Process for the production of methylol melamine solutions
US2980676A (en) * 1957-07-24 1961-04-18 Ciba Ltd Glycidyl ethers of n-methylolamino-1:3:5-triazines
CN115739043A (en) * 2022-11-10 2023-03-07 郑州大学 Triazine structure functionalized cationic organic polymer, and preparation method and application thereof

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1015438B (en) * 1953-11-30 1957-09-12 British Oxygen Co Ltd Process for the production of methylol melamine solutions
US2980676A (en) * 1957-07-24 1961-04-18 Ciba Ltd Glycidyl ethers of n-methylolamino-1:3:5-triazines
CN115739043A (en) * 2022-11-10 2023-03-07 郑州大学 Triazine structure functionalized cationic organic polymer, and preparation method and application thereof
CN115739043B (en) * 2022-11-10 2024-01-26 郑州大学 Triazine structure functionalized cationic organic polymer and preparation method and application thereof

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