GB818844A - New hardenable derivatives of formaldehyde condensation products of the aminotriazine or urea group, and their manufacture and use - Google Patents

New hardenable derivatives of formaldehyde condensation products of the aminotriazine or urea group, and their manufacture and use

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Publication number
GB818844A
GB818844A GB24391/55A GB2439155A GB818844A GB 818844 A GB818844 A GB 818844A GB 24391/55 A GB24391/55 A GB 24391/55A GB 2439155 A GB2439155 A GB 2439155A GB 818844 A GB818844 A GB 818844A
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GB
United Kingdom
Prior art keywords
ether
melamine
methylol
ethylene oxide
reacted
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
GB24391/55A
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.)
BASF Schweiz AG
Original Assignee
Ciba AG
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 Ciba AG filed Critical Ciba AG
Publication of GB818844A publication Critical patent/GB818844A/en
Expired legal-status Critical Current

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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
    • C08G12/40Chemically modified polycondensates

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  • Chemical & Material Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Phenolic Resins Or Amino Resins (AREA)

Abstract

The invention comprises hardenable cationactive derivatives of formaldehyde condensation products of compounds of the urea or aminotriazine series or ethers thereof with C1-C4 alcohols, which derivatives have (1) at least one free or etherified methylol group, (2) a polyglycol chain or a plurality of hydroxyethyl groups, (3) basic nitrogen atoms, and (4) no epoxide group. The components for making the derivatives are (a) a formaldehyde condensation product of a compound of the urea or aminotriazine series or an ether thereof with a C1-C4 alcohol, or a derivative (e.g. ester or ether) containing a hydrocarbon radical of 7 or more carbon atoms (such product having at least two methylol groups, free or etherified); (b) a compound capable of introducing a polyglycol ether chain or a plurality of hydroxyethyl groups; and (c) a primary, secondary or tertiary amine or salt or quaternary derivative thereof; the product is converted into a water-soluble or quaternary derivative if not such already. The starting materials can comprise mixtures, and can be reacted together simultaneously or in stages in any order. It is preferred either to react (b) with (c) and then the product with (a), or to react (a) with part of (b), (c) with the rest of (b) and then the two condensation products together. If any starting material contains an epoxide group this is opened during the reaction by choosing appropriate reaction conditions. Component (a) can be a methylol derivative of melamine, melam, melem, ammeline, ammelide, halo-aminotriazines, guanamines, guanyl-melamines (see Specification 730,018), urea, thiourea, dicyandiamide, dicyandiamidine, guanidine, acetoguanidine or biguanide; an ether of the preceding with a C1-C4 alcohol; a partial ether of any of the preceding with a higher alkanol, alkenol or benzyl alcohol; a partial ester of any of the preceding with a higher alkanoic, alkenoic, cycloaliphatic or aromatic acid; an amide derivative analogous to the above esters; or a partially polymerized or condensed derivative of the above. Component (b) can be ethylene oxide or a polyglycol or ether or ester thereof, e.g. a methyl ether, a glyceryl ether or an acetate. Component (c) can be an alkylamine, alkanolamine, alkylene diamine or polyalkylene polyamine, especially one containing an alkyl, alkenyl or cycloalkyl group of 8-40 carbon atoms attached directly or via an ester, ether or amide group; a cycloalkylamine or aralkylamine; an amino-substituted aromatic or heterocyclic compound; a compound containing an N-atom in a ring. Many suitable compounds of the above types are mentioned (e.g. dimethylethanolamine). The quaternating agent used before or after the condensation may be e.g. dimethyl sulphate, benzyl chloride, chloroacetamide or Nmethylol-chloroacetamide. The relative proportions of the components depend on the number of methylol groups in component (a) and the extent of any higher hydrocarbon groups present. The reaction may be carried out wholly or in part on a substratum such as a textile fibre. In examples: (1) hexamethylol-melamine is reacted successively with methyl alcohol (to etherify all the hydroxyl groups), 3 mols. of Nmethylol-chloracetamide and 1.5 mols. of the product of reacting 15 mols. of ethylene oxide with 1 mol. of N-(tallow alkyl)-trimethylene-diamine; (2) as in (1) but reacting the hexa(methoxy-methyl)-melamine with 2 mols. of polyethylene glycol before the amide and using only 1 mol. of the last component; (2) the following are reacted in the order stated: diethylene triamine, ethylene oxide, N-methylol-stearamide, hexa-(methoxymethyl)-melamine, benzyl chloride; (4) the following are reacted in order: N-(tallow alkyl)-trimethylene diamine, ethylene oxide, hexa - (methoxymethyl) - melamine, dimethyl sulphate; (5) the following are reacted in order: diethylene triamine, stearic acid, ethylene oxide, hexa-(methoxymethyl)melamine, acetic acid; (6) the condensation product of triethanolamine and ethylene oxide is reacted with urea and formaldehyde, and acidified with hydrochloric acid. Compounds analogous to those of the present invention but without the residue of component (b) are described in Specification 779,232.ALSO:The invention comprises hardenable cationactive derivatives of formaldehyde condensation products of compounds of the urea or aminotriazine series or ethers thereof with C1-C4 alcohols, which derivatives have (1) at least one free or etherified methylol group, (2) a polyglycol chain or a plurality of hydroxyethyl groups, (3) basic nitrogen atoms, and (4) no epoxide group. The components for making the derivatives are (a) a formaldehyde condensation product of a compound of the urea or aminotriazine series or an ether thereof with a C1-C4 alcohol, or a derivative (e.g. ester or ether) containing a hydrocarbon radical of 7 or more carbon atoms (such product having at least two methylol groups, free or etherified); (b) a compound capable of introducing a polyglycol ether chain or a plurality of hydroxyethyl groups; and (c) a primary, secondary or tertiary amine or salt or quaternary derivative thereof; the product is converted into a water-soluble or quaternary derivative if not such already. The starting materials can comprise mixtures, and can be reacted together simultaneously or in stages in any order. It is preferred either to react (b) with (c) and then the product with (a), or to react (a) with part of (b), (c) with the rest of (b) and then the two condensation products together. If any starting material contains an epoxide group this is opened during the reaction by choosing appropriate reaction conditions. Component (a) can be a methylol derivative of melamine, melam, melem, ammeline, ammelide, halo-aminotriazines, guanamines, guanyl-melamines (see Specification 730,018), urea, thiourea, dicyandiamide, dicyandiamidine, guanidine, acetoguanidine or biguanide; an ether of the preceding with a C1-C4 alcohol; a partial ether of any of the preceding with a higher alkanol, alkenol or benzyl alcohol; a partial ester of any of the preceding with a higher alkanoic, alkenoic, cycloaliphatic or aromatic acid; an amide derivative analogous to the above esters; or a partially polymerized or condensed derivative of the above. Component (b) can be ethylene oxide or a polyglycol or ether or ester thereof, e.g. a methyl ether, a glyceryl ether or an acetate. Component (c) can be an alkylamine, alkanolamine, alkylene diamine or polyalkylene polyamine, especially one containing an alkyl, alkenyl or cycloalkyl group of 8-40 carbon atoms attached directly or via an ester, ether or amide group; a cycloalkylamine or aralkylamine; an amino-substituted aromatic or heterocyclic compound; a compound containing an N-atom in a ring. Many suitable compounds of the above types are mentioned (e.g. dimethylethanolamine). The quaternating agent used before or after the condensation may be e.g. dimethyl sulphate, benzyl chloride, chloracetamide or N-methylol-chloracetamide. The relative proportions of the components depend on the number of methylol groups in component (a) and the extent of any higher hydrocarbon groups present. The reaction may be carried out wholly or in part on a substratum such as a textile fibre. In examples: (1) hexamethylol-melamine is reacted successively with methyl alcohol (to etherify all the hydroxyl groups), 3 mols. of N-methylol-chloracetamide and 1.5 mols. of the product of reacting 15 mols. of ethylene oxide with 1 mol. of N-(tallow alkyl)-trimethylenediamine; (2) as in (1) but reacting the hexa-(methoxymethyl)-melamine with 2 mols. of polyethylene glycol before the amide and using only 1 mol. of the last component; (3) the following are reacted in the order stated: diethylene triamine, ethylene oxide, N-methylolstearamide, hexa - (methoxymethyl) - melamine, benzyl chloride; (4) the following are reacted in order: N-(tallow alkyl)-trimethylene diamine, ethylene oxide, hexa-(methoxymethyl)-melamine, dimethyl sulphate; (5) the following are reacted in order: diethylene triamine, stearic acid, ethylene oxide, hexa-(methoxymethyl)-melamine, acetic acid; (6) the condensation product of triethanolamine and ethylene oxide is reacted with urea and formaldehyde, and acidified with hydrochloric acid. Compounds analogous to those of the present invention but without the residue of component (b) are described in Specification 779,232.ALSO:The surface conductivity of textile materials is improved by treating them with a compound as defined below, or with the components for making such a compound, the reaction being then completed on the fibre. The materials are impregnated with an aqueous or organic solution of the compound, dried, and, if desired, heated to, e.g., 120-150 DEG C., preferably in the presence of a hardening catalyst such as an acid or a salt thereof with a weak base. If an organic solvent is used this can be the acid or an ester which generates it on heating. If the compound contains a polymerizable group, this can be polymerized on the fibre in the presence of a catalyst such as a peroxide or per-salt, as in the process of Specification 779,232. The compounds of the invention are hardenable cation-active derivatives of formaldehyde condensation products of compounds of the urea or triazine series of ethers thereof with C1-C4 alcohols, which derivatives have (1) at least one free or etherified methylol group, (2) a polyglycol chain or a plurality of hydroxyethyl groups, (3) basic nitrogen atoms, and (4) no epoxide group. The components for making the compounds are: (a) a di- or poly-methylol derivative of melamine, melam, melem, ammeline, ammelide, halo - aminotriazine, guanamine, guanyl - melamine (see Specification 730,018), urea, thiourea, dicyandiamide, dicyandiamidine, guanidine, acetoguanidine or biguanide; an ether of the preceding with a C1-C4 alcohol; a partial ether of
GB24391/55A 1954-08-24 1955-08-24 New hardenable derivatives of formaldehyde condensation products of the aminotriazine or urea group, and their manufacture and use Expired GB818844A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH818844X 1954-08-24

Publications (1)

Publication Number Publication Date
GB818844A true GB818844A (en) 1959-08-26

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Application Number Title Priority Date Filing Date
GB24391/55A Expired GB818844A (en) 1954-08-24 1955-08-24 New hardenable derivatives of formaldehyde condensation products of the aminotriazine or urea group, and their manufacture and use

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GB (1) GB818844A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2003078490A1 (en) * 2002-03-15 2003-09-25 Shanghai Sujie Science-Technology Co. Ltd A kind of functional olefin mother grain and the method of it and the use of it

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2003078490A1 (en) * 2002-03-15 2003-09-25 Shanghai Sujie Science-Technology Co. Ltd A kind of functional olefin mother grain and the method of it and the use of it
US7282538B2 (en) 2002-03-15 2007-10-16 Shanghai Sujie Science-Technology Co., Ltd. East China University Of Science And Technology Preparation method of functional master batch of polyolefin and its application
US7531225B2 (en) 2002-03-15 2009-05-12 Shanghai Sujie Science-Technology Co. Ltd. Preparation method of functional master batch of polyolefin and its application

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