US3406032A - Emulsion for hydrophobing textiles - Google Patents

Emulsion for hydrophobing textiles Download PDF

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Publication number
US3406032A
US3406032A US471397A US47139765A US3406032A US 3406032 A US3406032 A US 3406032A US 471397 A US471397 A US 471397A US 47139765 A US47139765 A US 47139765A US 3406032 A US3406032 A US 3406032A
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emulsion
hydrophobing
emulsions
quaternary
salt
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US471397A
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Enders Heinz
Deiner Hans
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Chemische Fabrik Pfersee GmbH
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Chemische Fabrik Pfersee GmbH
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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
    • D06M13/47—Compounds containing quaternary nitrogen atoms derived from heterocyclic compounds
    • 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
    • D06M13/02—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with hydrocarbons
    • 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
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T442/00—Fabric [woven, knitted, or nonwoven textile or cloth, etc.]
    • Y10T442/20—Coated or impregnated woven, knit, or nonwoven fabric which is not [a] associated with another preformed layer or fiber layer or, [b] with respect to woven and knit, characterized, respectively, by a particular or differential weave or knit, wherein the coating or impregnation is neither a foamed material nor a free metal or alloy layer
    • Y10T442/2221—Coating or impregnation is specified as water proof
    • Y10T442/2246—Nitrogen containing

Definitions

  • a product for hydrophobing textiles and other fibrous materials consists of an aqueous emulsion of paraflin with a quaternary ammonium salt as emulsifier which decomposes and produces Water repellency when heated, the emulsion containing 3 to 15 parts by weight of parafiin to 1 part by weight of the quaternary ammonium salt.
  • the salt has one aliphatic residue with at least 12 carbon atoms.
  • This invention relates to an emulsion for hydrophobing fibrous materials, particularly textiles.
  • An object of the present invention is to improve prior art hydrophobing products.
  • emulsions having 3 to 15 parts, preferably 5 to parts parafiin to 1 part of a salt of a quaternary nitrogen base which de compose when heatedthe base having 1 aliphatic residue with at least 12, preferably at least 16 carbon atoms-are more stable in concentrated, as well as diluted state, than 3,406,032 Patented Oct. 15, 1968 emulsions with a smaller amount of paraffin; it was further discovered that they have hydrophobing elfects which are more permanent in washing than those of the known emulsions.
  • the emulsions of the present invention are manufactured in the usual manner preferably in a concentrated state and in use are diluted with water.
  • R is an aliphatic, possibly branched off or unsaturated residue with at least 12, preferably at least 16 carbon atoms;
  • R R and R are aliphatic, cycloaliphatic or aromatic residues, such as methyl, ethyl, propyl, cyclohexyl or benzyl; however, NR R R can also represent a heterocyclic residue, such as pyridine or its homologs, oxyethylmorpholine, N-ethylpiperidine or chinoline.
  • X- is an anion used for salt formation, particularly an anion of a strong inorganic preferably volatile acid.
  • Y is a heteroatom, particularly oxygen, or an atom grouping containing at least 1 hetero-atom.
  • X is the anion of a strong inorganic acid, preferably hydrochloric acid.
  • parafiins such having a melting point above 45 C., preferably 50 Cr- C.
  • the melting point should not be higher than C.
  • the concentrated emulsions of the present invention are produced by mechanical emulsification in the usual manner; solvents for paraffin, such as aromatic hydrocarbons, or halogenated aliphatic hydrocarbons can be also included.
  • solvents for paraffin such as aromatic hydrocarbons, or halogenated aliphatic hydrocarbons can be also included.
  • these emulsions are very stable and can be stored for very lengthy time periods. Diluted emulsions are also stable, so that treating baths during continuous operations leave a much lesser coating upon the foulard rollers than prior art emulsion having less paraffin.
  • the treated textiles after drying are heated in a known manner to about C.- C., to complete the decomposition of the salt of the quaternary base and the fixing of the remaining compounds.
  • hydrophobic treatment of textiles with the emulsions of the present invention can be further improved in certain cases as far as resistance against hot washing is concerned, by the additional use of salt of 3 (or more) v-alent metals with inorganic or organic acids, particularly salts of zircon with low organic carboxylic acids.
  • the emulsions of the present invention can be combined with other usual textile finishing products.
  • EXAMPLE 1 30 gr. octadecyl-oxymethyl-pyridinium chloride were dissolved at 60 C. in 130 gr. water. 195 gr. parafiin-- melting point 58/ 60 C.-were added thereto in a thin spray with the use of a high-speed stirrer. The pre-emulsion was diluted with 295 gr. water containing 6 com. acetic acid (60% Then the final emulsification took place in a high pressure homogenizing machine at a temperature between 60 C. and 70 C. and at 200-300 super-atmospheric pressure. This emulsion contained 4.6% quaternary pyridinium salt and 28.5% paraffin.
  • Emulsions were produced in accordance with Example 1 by the use of octadecyl-oxymethyl-oxyethyl-morpholine chloride and increasing amounts of par-aflin, whereby in each case the total solid content (quaternary salt plus parafiin) amounted to 35%. l
  • a cotton sa-tin was finished with these emulsions in baths which always contained 200 gr. of the emulsion, 10 gr. cryst. zirconium oxychloride and 8 gr. sodium acetate. The drying and the heating of the fabrics took place in accordance with the procedure of Example 1.
  • EXAMPLE 4 As described in Example 1, an emulsion of 160 gr. of a 19% aqueous solution of octadecyloxy-methyldiethyl ammonium chloride and gr. paraffin (melting point 50/ 52 C.) was produced with the addition of water and acetic acid by stirring and homogenation.
  • a cotton fabric which was treated with a bath containing 400 gr. of this emulsion, 40 gr. of a 50% dimethylol ethylene urea, 10 gr. cryst. zirconium oxychloride and 8 gr. cryst. sodium acetate, dried and subsequently heated, receives a water absorption of 10%, which after 5 hot washings is increased to only 19%.
  • EXAMPLE 5 A cotton moleskin was saturated with a bath containing per liter 200 gr. of the emulsion indicated in Example 1, 40 gr. of a 50% aqueous pre-condensation solution (35% of dimethylol ethylene urea and 15% of a methylether of hexarnethylolmelamine), 15 gr. cryst. zirconium oxychloride as well as 8 gr. cryst. sodium acetate; it was dried and cured for 6 minutes at C. As the result of a spray test the fabric was found to have a water absorption of 7.9% which was increased after 5 hot washings to only 23.2%.

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  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Colloid Chemistry (AREA)
  • Materials Applied To Surfaces To Minimize Adherence Of Mist Or Water (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)

Description

United States atent O EMULSION FOR HYDROPHOBING TEXTILES Heinz Enders, Stadtbergen, Augsburg, and Hans Deiner,
Neusass-Lohwald, Augsburg, Germany, assignors to Chemische Fabrik Pfersee G.m.b.H., Augsburg, Germany, a firm of Germany No Drawing. Filed July 12, 1965, Ser. No. 471,397 Claims priority, application Germany, July 22, 1964,
6 Claims. (Cl. 106271) ABSTRACT OF THE DISCLOSURE A product for hydrophobing textiles and other fibrous materials consists of an aqueous emulsion of paraflin with a quaternary ammonium salt as emulsifier which decomposes and produces Water repellency when heated, the emulsion containing 3 to 15 parts by weight of parafiin to 1 part by weight of the quaternary ammonium salt. The salt has one aliphatic residue with at least 12 carbon atoms.
This invention relates to an emulsion for hydrophobing fibrous materials, particularly textiles.
It is known in prior art to treat fibrous materials with quaternary ammonium salts which have at least one higher aliphatic residue and which decompose when heated, so as to produce water repellent effects. The hydrophobing results which are thus obtained are so completely unsatisfactory from the point of view of present day requirements, that the use of a technical charge as hydrophobing products is not even considered any more.
The addition of metal salts or synthetic resin precondensates, which has also been suggested, does not provide practically any improvement.
It was also suggested to add emulsions of parafiin to treating baths containing such quaternary salts. This requires a special manufacture of such emulsions.
Furthermore, it was stated that self-emulsifying astes could be manufactured from quaternary ammonium salts with one half of or at most the same amount by weight of parafiin with the addition of organic solvents, and that these pastes could be used for hydrophobing fibrous materials. These emulsions have often poor stability in concentrated as Well as diluted states and the hydrophobing effects produced by them, as well as their resistance against washing, do not satisfy modern requirements. An increase in the concentration of the quaternary ammonium salt does not yield an improvement which would be commensurate with the increased consumption of material.
An object of the present invention is to improve prior art hydrophobing products.
Other objects will become apparent in the course of the following specification.
During the accomplishment of the objectives of the present invention it was surprisingly found that emulsions having 3 to 15 parts, preferably 5 to parts parafiin to 1 part of a salt of a quaternary nitrogen base which de compose when heatedthe base having 1 aliphatic residue with at least 12, preferably at least 16 carbon atoms-are more stable in concentrated, as well as diluted state, than 3,406,032 Patented Oct. 15, 1968 emulsions with a smaller amount of paraffin; it was further discovered that they have hydrophobing elfects which are more permanent in washing than those of the known emulsions. Actually, it could have been expected that emulsions with a lower ratio of the emulsifier to the dispersed substance would be less stable and that an increase in the paraffin component which by itself is not wash resistant, would make substantially worse the wash resistance of the produced hydrophobic effects.
The emulsions of the present invention are manufactured in the usual manner preferably in a concentrated state and in use are diluted with water.
As salts of quaternary nitrogen bases are used known compounds having the formulae:
wherein R is an aliphatic, possibly branched off or unsaturated residue with at least 12, preferably at least 16 carbon atoms; R R and R are aliphatic, cycloaliphatic or aromatic residues, such as methyl, ethyl, propyl, cyclohexyl or benzyl; however, NR R R can also represent a heterocyclic residue, such as pyridine or its homologs, oxyethylmorpholine, N-ethylpiperidine or chinoline. X- is an anion used for salt formation, particularly an anion of a strong inorganic preferably volatile acid. Y is a heteroatom, particularly oxygen, or an atom grouping containing at least 1 hetero-atom. Carbon amido-groups are, however, less suitable since salts of such quaternary nitrogen bases have in general a worse emulsification capacity-even with respect to small amounts of parafiinand their aqueous solutions when standing in the heat often produce decompositions of the quaternary salts.
In accordance with the present invention compounds of the following formula are preferred, since they were found to be particularly successful in use:
They include tertiary heterocyclic amines, particularly pyridine. X is the anion of a strong inorganic acid, preferably hydrochloric acid.
The manufacture of the salts of quaternary nitrogen bases takes place in accordance with known processes.
As parafiins are used such having a melting point above 45 C., preferably 50 Cr- C. To avoid difficulties in the manufacture of the emulsion the melting point should not be higher than C.
The concentrated emulsions of the present invention are produced by mechanical emulsification in the usual manner; solvents for paraffin, such as aromatic hydrocarbons, or halogenated aliphatic hydrocarbons can be also included. Despite substantial excess of paraffin with respect to the emulsifyingly acting salt of the quaternary nitrogen base, these emulsions are very stable and can be stored for very lengthy time periods. Diluted emulsions are also stable, so that treating baths during continuous operations leave a much lesser coating upon the foulard rollers than prior art emulsion having less paraffin.
The treated textiles after drying are heated in a known manner to about C.- C., to complete the decomposition of the salt of the quaternary base and the fixing of the remaining compounds.
The hydrophobic treatment of textiles with the emulsions of the present invention can be further improved in certain cases as far as resistance against hot washing is concerned, by the additional use of salt of 3 (or more) v-alent metals with inorganic or organic acids, particularly salts of zircon with low organic carboxylic acids.
The emulsions of the present invention can be combined with other usual textile finishing products. By Way of example, there can be added to the finishing baths creaseproofing products, products preventing swelling, anti-slipping agents, filling agents, softeners, etc.
The following examples are given by way of exemplification only:
EXAMPLE 1 30 gr. octadecyl-oxymethyl-pyridinium chloride were dissolved at 60 C. in 130 gr. water. 195 gr. parafiin-- melting point 58/ 60 C.-were added thereto in a thin spray with the use of a high-speed stirrer. The pre-emulsion was diluted with 295 gr. water containing 6 com. acetic acid (60% Then the final emulsification took place in a high pressure homogenizing machine at a temperature between 60 C. and 70 C. and at 200-300 super-atmospheric pressure. This emulsion contained 4.6% quaternary pyridinium salt and 28.5% paraffin.
200 gr. of the emulsion were diluted with water to 1 liter. A cotton moleskin was impregnated with this bath, squeezed to 70% bath absorption, dried for 30 minutes at 120 C. and thereupon heated for minutes at 150 C.
This fabric in the original untreated condition had a water absorption of 87% (measured upon the Bundesmann apparatus with 10 minutes shower duration) and after 5 hot Washes with soap and soda according to the norm VTL 8305l25 had a water absorption of 90%. However after the finishing with the emulsion of the present invention the water absorption dropped to only 8.6%. After 5 hot washes the water absorption had risen to 34.8%.
Such good and wash-resistant hydrophobic effects can not be attained with the same finishing of the same cotton moleskin by the use of only \the quaternary salt, or by the use of paraffin alone, or by the use of an emulsion having equal parts of parafiin and quaternary salt, as is apparent from the following comparative treatment data:
(a) A bath of 9.2. gr. octadecyl-oxymethyl-pyridinium chloride per liter water and then squeezing to 70% bat-h absorption.
(b) A solution of 65 gr. paraffin in 1 liter=l630 gr. tetrachloroethylene and 100% bath absorption, so that there was the same amount of paraffin upon the fabric as with the previous finishes.
(c) A bath having per liter water 100 gr. of a paste corresponding to Example 1 of British patent specification No. 612,915 (30% stearamido-methyl-pyridinium chloride and 30% parafiin) with 70% bath absorption.
(cl) An aqueous bath of 100 gr. of a paste corresponding to that of paragraph (c), wherein however, stearamido-methyl-pyridinium chloride is replaced by the same amount of octadccyloxymethylpyridinium chloride, with 70% bath absorption.
The results obtained are set forth in the following table:
Emulsions were produced in accordance with Example 1 by the use of octadecyl-oxymethyl-oxyethyl-morpholine chloride and increasing amounts of par-aflin, whereby in each case the total solid content (quaternary salt plus parafiin) amounted to 35%. l
A cotton sa-tin was finished with these emulsions in baths which always contained 200 gr. of the emulsion, 10 gr. cryst. zirconium oxychloride and 8 gr. sodium acetate. The drying and the heating of the fabrics took place in accordance with the procedure of Example 1.
The spraying examination prior to and after hot washings produced the following results:
TAB LE II Water absorption (percent) Ratio of quaternary salt to paratiin Immediate After 5 hot washings EXAMPLE 3 EXAMPLE 4 As described in Example 1, an emulsion of 160 gr. of a 19% aqueous solution of octadecyloxy-methyldiethyl ammonium chloride and gr. paraffin (melting point 50/ 52 C.) was produced with the addition of water and acetic acid by stirring and homogenation.
A cotton fabric which was treated with a bath containing 400 gr. of this emulsion, 40 gr. of a 50% dimethylol ethylene urea, 10 gr. cryst. zirconium oxychloride and 8 gr. cryst. sodium acetate, dried and subsequently heated, receives a water absorption of 10%, which after 5 hot washings is increased to only 19%.
EXAMPLE 5 A cotton moleskin was saturated with a bath containing per liter 200 gr. of the emulsion indicated in Example 1, 40 gr. of a 50% aqueous pre-condensation solution (35% of dimethylol ethylene urea and 15% of a methylether of hexarnethylolmelamine), 15 gr. cryst. zirconium oxychloride as well as 8 gr. cryst. sodium acetate; it was dried and cured for 6 minutes at C. As the result of a spray test the fabric was found to have a water absorption of 7.9% which was increased after 5 hot washings to only 23.2%.
It is apparent that the examples described above have been given solely by way of illustration and not by Way of limitation and that they are capable of many variations and modifications Within the scope of the present invention. All such variations and modifications are to be included within the scope of the present invention.
What is claimed is:
1. Product for hydrophobing fibrous materials, said product consisting of an aqueous emulsion of paraffin with a quaternary ammonium salt which decomposes when heated as emulsifier having the formula wherein R is an alkyl with at least 12 carbon atoms, N.(tert.) is a tertiary heterocyclic nitrogen base and X is the anion of a volatile inorganic acid, wherein the emul- 5 6 sion contains 3 to 15 parts by weight parafiin to 1 part 6. A fibrous material treated by the product described by weight of the quaternary ammonium salt, said parafin claim 1. fin having a melting point between 45 C. and 90 C. References Cited 2. Product in accordance with claim 1, wherein the UNITED STATES PATENTS alkyl R has at least 16 carbon atoms. 5
3. Product in accordance with claim 1, wherein the 2,200,944 5/1940 tertiary heterocyclic nitrogen base is pyridine. 2,426,300 8/1947 Edelstem 106-271 4. Product in accordance with claim 1, wherein the 2,277,174 3/1942 Waitman 260' 297 inorganic acid is hydrochloric acid. 2,054,257 9/1936 Hueter 106 271 5. Product in accordance with claim 1, wherein the 10 2,125,901 8/1938 Evans 260-297 emulsion contains 5 to 10 parts by weight paraffin to 1 part by weight of the quaternary ammonium salt. ALLAN LIEBERMAN Pnnmry Exammer'
US471397A 1964-07-22 1965-07-12 Emulsion for hydrophobing textiles Expired - Lifetime US3406032A (en)

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DEC33460A DE1290517B (en) 1964-07-22 1964-07-22 Water repellants for fiber materials

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AT (1) AT256779B (en)
BE (1) BE667153A (en)
CH (1) CH407035A (en)
DE (1) DE1290517B (en)
GB (1) GB1116511A (en)
NL (1) NL141258B (en)
SE (1) SE334140B (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3490925A (en) * 1967-03-15 1970-01-20 Diamond Shamrock Corp Water repellent
US4969952A (en) * 1986-12-22 1990-11-13 Grace Service Chemicals Gmbh Release agent for urethane foam molding

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2054257A (en) * 1933-11-17 1936-09-15 Deutsche Hydrierwerke Ag Emulsification process
US2125901A (en) * 1936-01-15 1938-08-09 Ici Ltd Finishing textile materials
US2200944A (en) * 1937-08-27 1940-05-14 Tootal Broadhurst Lee Co Ltd Textile finishing process
US2277174A (en) * 1936-05-19 1942-03-24 Heberlein Patent Corp Process for producing water-repellent textile materials and product therefrom
US2426300A (en) * 1944-04-03 1947-08-26 Sidney M Edelstein Method and composition for waterproofing

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR1269354A (en) * 1959-07-15 1961-08-11 Scan Vax Fabrikations Process for coating cellulosic materials, resulting product and their applications

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2054257A (en) * 1933-11-17 1936-09-15 Deutsche Hydrierwerke Ag Emulsification process
US2125901A (en) * 1936-01-15 1938-08-09 Ici Ltd Finishing textile materials
US2277174A (en) * 1936-05-19 1942-03-24 Heberlein Patent Corp Process for producing water-repellent textile materials and product therefrom
US2200944A (en) * 1937-08-27 1940-05-14 Tootal Broadhurst Lee Co Ltd Textile finishing process
US2426300A (en) * 1944-04-03 1947-08-26 Sidney M Edelstein Method and composition for waterproofing

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3490925A (en) * 1967-03-15 1970-01-20 Diamond Shamrock Corp Water repellent
US4969952A (en) * 1986-12-22 1990-11-13 Grace Service Chemicals Gmbh Release agent for urethane foam molding

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Publication number Publication date
AT256779B (en) 1967-09-11
NL6509087A (en) 1966-01-24
GB1116511A (en) 1968-06-06
SE334140B (en) 1971-04-19
DE1290517B (en) 1969-03-13
BE667153A (en) 1965-11-16
CH407035A (en) 1966-02-15
NL141258B (en) 1974-02-15

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