US3558711A - Tertiary n-alkyl-n-(2-hydroxyalkyl)-polyhydroxy-alkylamines - Google Patents

Tertiary n-alkyl-n-(2-hydroxyalkyl)-polyhydroxy-alkylamines Download PDF

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US3558711A
US3558711A US700891*A US3558711DA US3558711A US 3558711 A US3558711 A US 3558711A US 3558711D A US3558711D A US 3558711DA US 3558711 A US3558711 A US 3558711A
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alkyl
carbon atoms
tertiary
hydroxyalkyl
products
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English (en)
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Arnold Heins
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Henkel AG and Co KGaA
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Henkel AG and Co KGaA
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    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
    • D06M13/46—Compounds containing quaternary nitrogen atoms
    • D06M13/463—Compounds containing quaternary nitrogen atoms derived from monoamines
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
    • D06M13/46—Compounds containing quaternary nitrogen atoms

Definitions

  • Z is a polyhydroxyalkyl of 3-6 carbon atoms
  • R1 is an alkyl of 8-18 carbon atoms
  • R2 is an alkyl of 6-18 carbon atoms, R1
  • This invention relates to tertiary N-alkylN-(2hydroxy alkyl)-polyhydroxyalkylamines, the quaternary ammonium compounds thereof and to methods for preparing and using the same.
  • R1 is alkyl having 8-18 carbon atoms, which alkyl may possibly be interrupted by an oxygen atom
  • R2 is alkyl having 6-18 carbon atoms, the total of the carbon atoms present in R1 and R2 together amounting to 24-36 and preferably 28-32
  • Z is polyhydroxyalkyl having 3-6 carbon atoms,the number of hydroxyl groups present in said polyhydroxyalkyl group being at least half the number of carbon atoms, and their corresponding quaternary compounds which in addition contain a further radical having up to 8 carbon atoms bound to the nitrogen atom can be obtained by reacting a secondary N- alkyl -polyhydroxyalkylamine of the formula:
  • R1 and Z are as above defined, with a terminal alkylene oxide having 8-20 carbon atoms and thereafter if the quaternary compound is desired, quaternizing the resultant tertiary amine by introduction of an organic radical containing at the most 8 carbon atoms.
  • the number of hydroxyl groups present in Z is preferably l less than the number of carbon atoms contained therein. Accordingly, there enter into consideration as illustrative of Z the following moieties:
  • the secondary amines having the formula Z-NH-R1 which are to be used as starting materials in accordance with the process of the invention can be prepared in the conventional manner, as for instance by reacting a primary amine R1-NH2 with a halohydrin or epoxide of a corresponding structure and which contains hydroxyl groups.
  • Suitable hexoses are in particular, glucose, mannose, galactose, fructose, sorbose or their mixtures, such as, for instance, invert sugar; however, their oligomers, such as maltose, can also be used. Mixtures of different hexoses and mixtures of hexoses and pentoses can also be employed.
  • the alkyl groups of the primary Rl-NH2 amines which may be used in the preparation of the Z-NH--R1 starting materials may be saturated or unsaturated, straight or branched chain, synthetic or of natural origin.
  • the R1 groups present in the amines can be derived from octyl, decyl-, dodecyl, tetradecyl, cetyl, stearylor oleyl-amine.
  • Amines in which the NH2 group and ether oxygen atom are separated from each other by 3 carbon atoms, are obtained, for instance, by the addition of acrylonitrile to a fatty alcohol of corresponding chain length followed by reduction of the nitrile group.
  • the alkyl groups of these amines can be present as mixtures of homologs, such as can be obtained, for example, from fats of natural origin, as for instance, from plants or land or sea animals. Instances of such natural materials are palm oil, linseed oil, cottonseed oil, peanut oil, rape oil, etc., lard, tallow, iish and Walrus oil. Fractions of the fatty acids contained in all these fats can also be used for the preparation of the amines.
  • the amines which are to be used are preferably not too highly unsaturated, i.e. the iodine numbers of the starting fatty acids should preferably not be more than 50 and in particular not more than 30'. Amines of substantially completely hydrogenated fatty acids having iodine numbers of less than and preferably less than 5 can also be used.
  • terminal epoxides which are to be reacted in accordance with the invention with the secondary N-alkyl-N-polyhydroxyalkylamines it is necessary only to carry out an epoxidation of a terminal olen which itself can be prepared by various known methods, as for instance, by the cracking of petroleum parains.
  • a mixture of the starting materials is heated to a temperature at which no water is split olf from the polyhydroxyalkylamine and preferably to a temperature within the range of 1Z0-170 C.
  • the starting materials are preferably employed in equimolar quantities, but small excesses of one component amounting to, for instance, up to 30 mol percent can also be used.
  • the reaction proceeds even in the absence of any catalyst at an industrially acceptable velocity. Solvents are not required, although it is possible to operate, particularly in the case of small batches, in the presence of inert solvents. In industrial operation, the use of solvents are dispensed with or they are used in such small quantities that they constitute at most 50% by weight of the total reaction mixture.
  • the crude products obtained are generally of yellowish color. Their consistency depends to a great degree on the nature of the two groups R1 and R2.
  • the products produced by the method of the invention constitute solids and are readily crystallizable. With an increase in the number of the isomers of different chain lengths present in the product, the products become waxlike or pasty. The presence of chain branchings also result in products of a pasty consistency.
  • a group containing at most 8 carbon atoms is introduced into the polyhydroxalkylamine in the conventional manner by reacting the tertiary polyhydroxyalkylamine with a known quaternizing agent.
  • Suitable quaternizing agents include, for instance, dimethlsulfate, diethylsulfate and other dialkylsulfates, alkyl halides, such as methylor ethyl bromide, alkylene halohydrins, such as ethylene bromhydrin, propylene bromhydrin, glycerin chlorhydrin, epichlorhydrin, etc.
  • Alkyl aromatic compounds such as benzyl chloride and benzyl bromide, can also be used as quaternizing agent.
  • the preferred agents are those having alkyl groups containing 1-4 carbon atoms. Quaternizing agents which contain hydoxyl groups or epoxide groups are of particular interest insofar as the solubility of the resultant quaternary compounds and their salts is improved by the presence of the oxygen function.
  • the tertiary and quaternary N-alkyl-N-(Z-hydroxyalkyl)-polyhydroxyalkylamine products of the invention are obtained as crude materials and can be used as such as textile softeners. If desired, the products and the tertiary compounds in particular can be purified by recrystallization or redissolving from suitable organic solvents.
  • the products of the invention are of poor solubility in water.
  • suitable water-soluble organic solvents such as monohydric or polyhydric alcohols having 1-4 carbon atoms, or ether alcohols, such as, for instance, the monoethers of the said monohydric alcohols, with ethylene glycol, ethylene diglycol, propylene glycol, butylene glycol or the monoor diethers of the said monohydric alcohols with glycerin.
  • the tertiary products are soluble in these solvents, as well as in lower water-soluble ketones. Of these solvents, those having boiling points of up to C. are particularly suitable for the recrystallization or redissolving.
  • the purified products separate from the solvent employed in crystalline or amorphous condition, depending on the nature of the alkyl groups.
  • the terrycloth samples were washed l5 times in succession in a drum washing machine using a commercial detergent intended for use in such Washing machines.
  • the wash-active substance of the 4washing agent used consisted essentially of a combination of capillary-active sulfonates and soaps. The highest temperature obtained during the boil washing was between 95 and 100 C.
  • Grade 1 Hand is full and very soft Grade 2: Hand is soft Grade 3: Hand is of medium hardness Grade 4: Hand is hard Insofar as the grades given by the individual testers did not agree, an average was obtained based on the individual grades.
  • the principle of the design of the apparatus used for the measurement can be noted from the accompanying drawing.
  • the material to be tested is allowed to rest on the base plate 1 and was compressed by the feeler which is movable vertically thereover.
  • the feeler consists of the feeler plate 2, the vertical shaft 3 and the bearing surface 4 and is guided by the vertical shaft 3 which, however, rests completely without friction on the base during the measurement. ln the extension of the feeler axis there is contained the feeler of a measuring dial 6 on the scale of which 0.01 mm. can be read off as the smallest unit.
  • the feeler plate 2 was lowered onto the base plate 1 and the feeler 5 was moved downward until it just contacts the bearing surface 4 of the feeler.
  • the moment of contact between feeler 5 and bearing surface 4 is indicated in the case of the apparatus employed through a glow lamp.
  • the sample of fabric to be tested was placed on the base plate 1, the fabric completely covering the base plate and extending beyond it at its edges.
  • the feeler (area 25 cm?, weight 50 g.) was then lowered onto the piece of fabric to be ⁇ tested and its thickness measured after a waiting time of one minute. The process was repeated a further two times on the same piece of fabric, the measuring pressure being increased by applying weights onto the feeler plate 2 to 10 times (500 g.) and 25 times (1250 g.) the initial value.
  • EXAMPLE 5 Z: polyhydroxyalkyl radical derived from glucose
  • R1 alkyl mixture derived from coconut fatty acid C12-C18
  • R2 alkyl mixture C13-C16 Crude product: yellowish brown paste Purilied product: yellowish paste Hand: 1.5 Compressibility:
  • EXAMPLE 6 Z: polyhydroxyalkyl radical derived from invert sugar R1: lkyl mixture derived from coconut fatty acid C12-C13,
  • R2 alkyl mixture C13-C16 Crude product: yellowish brown paste Purified product: yellowish paste Hand: 2.0 Compressibility:
  • the hardness of the terrycloth treated is in no way inuenced by the known products.
  • the use of the products in accordance with the invention results in a softness of the terrycloth sample which can be observed both subjectively and objectively.
  • R1 is a member selected from the group consisting of alkyl having 8-18 carbon atoms and alkyl having 8-18 carbon atoms interrupted by an oxygen atom
  • R2 is alkyl having 6-18 carbon atoms
  • R1 and R2 together have a total of 28-32 Carbon atoms.
  • R1 is alkyl interrupted by an ether oxygen atom, said oxygen atom being located between carbon atoms 2 and 3.
  • R1 is alkyl interrupted by an ether oxygen atom, said oxygen atom being located between carbon atoms 3 and 4.

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  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
US700891*A 1967-02-09 1968-01-26 Tertiary n-alkyl-n-(2-hydroxyalkyl)-polyhydroxy-alkylamines Expired - Lifetime US3558711A (en)

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DEH0061792 1967-02-09

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US3558711A true US3558711A (en) 1971-01-26

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US (1) US3558711A (is")
JP (1) JPS4842833B1 (is")
AT (1) AT280231B (is")
BE (1) BE710494A (is")
CH (1) CH496653A (is")
DE (1) DE1593894A1 (is")
DK (1) DK122273B (is")
ES (1) ES350302A1 (is")
FR (1) FR1562129A (is")
GB (1) GB1214581A (is")
NL (1) NL6800739A (is")
SE (1) SE358152B (is")

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4281201A (en) * 1979-12-10 1981-07-28 Quad Chemical Corporation Tertiary amines for use in water base hair care compositions
US4311692A (en) * 1979-12-10 1982-01-19 Quad Chemical Corporation Tertiary amine personal care composition
US4389526A (en) * 1981-08-03 1983-06-21 The Regents Of The University Of California Intermediates and synthesis of 2-amino-2-deoxytetritols
US4696771A (en) * 1985-12-03 1987-09-29 Henkel Corporation Aminopolyols and polyurethanes prepared therefrom

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS52160535U (is") * 1976-05-28 1977-12-06
EP0035728A1 (de) * 1980-03-10 1981-09-16 Henkel Kommanditgesellschaft auf Aktien Cytostatisch wirksame Aminopolyole, diese Verbindungen enthaltende Arzneimittel und ihre Anwendung
US4485259A (en) * 1982-09-30 1984-11-27 Ppg Industries, Inc. Pigment grinding vehicle

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4281201A (en) * 1979-12-10 1981-07-28 Quad Chemical Corporation Tertiary amines for use in water base hair care compositions
US4311692A (en) * 1979-12-10 1982-01-19 Quad Chemical Corporation Tertiary amine personal care composition
US4389526A (en) * 1981-08-03 1983-06-21 The Regents Of The University Of California Intermediates and synthesis of 2-amino-2-deoxytetritols
US4696771A (en) * 1985-12-03 1987-09-29 Henkel Corporation Aminopolyols and polyurethanes prepared therefrom

Also Published As

Publication number Publication date
AT280231B (de) 1970-04-10
GB1214581A (en) 1970-12-02
BE710494A (is") 1968-08-08
JPS4842833B1 (is") 1973-12-14
SE358152B (is") 1973-07-23
ES350302A1 (es) 1969-05-01
DK122273B (da) 1972-02-14
FR1562129A (is") 1969-04-04
DE1593894A1 (de) 1971-02-25
CH496653A (de) 1970-11-13
CH185268A4 (is") 1970-11-13
NL6800739A (is") 1968-08-12

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