US3406032A - Emulsion for hydrophobing textiles - Google Patents
Emulsion for hydrophobing textiles Download PDFInfo
- 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
- Authority
- US
- United States
- Prior art keywords
- emulsion
- hydrophobing
- emulsions
- quaternary
- salt
- 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 - Lifetime
Links
- 239000000839 emulsion Substances 0.000 title description 33
- 239000004753 textile Substances 0.000 title description 6
- 150000003839 salts Chemical class 0.000 description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- 238000010521 absorption reaction Methods 0.000 description 12
- 239000012188 paraffin wax Substances 0.000 description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 9
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- 238000005406 washing Methods 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 239000002657 fibrous material Substances 0.000 description 6
- 229920000742 Cotton Polymers 0.000 description 5
- 125000001931 aliphatic group Chemical group 0.000 description 5
- 239000004744 fabric Substances 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 150000001450 anions Chemical class 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 150000007522 mineralic acids Chemical class 0.000 description 4
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000004945 emulsification Methods 0.000 description 3
- 239000003995 emulsifying agent Substances 0.000 description 3
- 125000000623 heterocyclic group Chemical group 0.000 description 3
- 230000002209 hydrophobic effect Effects 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- CMOAHYOGLLEOGO-UHFFFAOYSA-N oxozirconium;dihydrochloride Chemical compound Cl.Cl.[Zr]=O CMOAHYOGLLEOGO-UHFFFAOYSA-N 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 239000001632 sodium acetate Substances 0.000 description 3
- 235000017281 sodium acetate Nutrition 0.000 description 3
- PUMIBBNWDCWIKR-UHFFFAOYSA-M 1-(octadecoxymethyl)pyridin-1-ium;chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCCOC[N+]1=CC=CC=C1 PUMIBBNWDCWIKR-UHFFFAOYSA-M 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- WVJOGYWFVNTSAU-UHFFFAOYSA-N dimethylol ethylene urea Chemical compound OCN1CCN(CO)C1=O WVJOGYWFVNTSAU-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- -1 heterocyclic amines Chemical class 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- ADABARLJFURQEM-UHFFFAOYSA-N n-(1-methylpyridin-1-ium-2-yl)octadecanamide;chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCC(=O)NC1=CC=CC=[N+]1C ADABARLJFURQEM-UHFFFAOYSA-N 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- IIGSLCSZHSIULZ-UHFFFAOYSA-N 4-[2-(octadecoxymethoxy)ethyl]morpholin-4-ium chloride Chemical compound [Cl-].C(CCCCCCCCCCCCCCCCC)OCOCC[NH+]1CCOCC1 IIGSLCSZHSIULZ-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- HTLZVHNRZJPSMI-UHFFFAOYSA-N N-ethylpiperidine Chemical compound CCN1CCCCC1 HTLZVHNRZJPSMI-UHFFFAOYSA-N 0.000 description 1
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 1
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000004855 creaseproofing Methods 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000000265 homogenisation Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000002940 repellent Effects 0.000 description 1
- 239000005871 repellent Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 229950011008 tetrachloroethylene Drugs 0.000 description 1
- 238000009988 textile finishing Methods 0.000 description 1
- 229910052845 zircon Inorganic materials 0.000 description 1
- GFQYVLUOOAAOGM-UHFFFAOYSA-N zirconium(iv) silicate Chemical class [Zr+4].[O-][Si]([O-])([O-])[O-] GFQYVLUOOAAOGM-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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%.
Landscapes
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Materials Applied To Surfaces To Minimize Adherence Of Mist Or Water (AREA)
- Colloid Chemistry (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEC33460A DE1290517B (de) | 1964-07-22 | 1964-07-22 | Hydrophobiermittel fuer Fasermaterialien |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3406032A true US3406032A (en) | 1968-10-15 |
Family
ID=7020842
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US471397A Expired - Lifetime US3406032A (en) | 1964-07-22 | 1965-07-12 | Emulsion for hydrophobing textiles |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US3406032A (de) |
| AT (1) | AT256779B (de) |
| BE (1) | BE667153A (de) |
| CH (1) | CH407035A (de) |
| DE (1) | DE1290517B (de) |
| GB (1) | GB1116511A (de) |
| NL (1) | NL141258B (de) |
| SE (1) | SE334140B (de) |
Cited By (2)
| 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 |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2222653C1 (ru) * | 2002-05-28 | 2004-01-27 | Ивановский государственный химико-технологический университет | Состав для обработки текстильных волокон и пряжи |
Citations (5)
| 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)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1269354A (fr) * | 1959-07-15 | 1961-08-11 | Scan Vax Fabrikations | Procédé de revêtement de matières cellulosiques, produit en résultant et leurs applications |
-
1964
- 1964-07-22 DE DEC33460A patent/DE1290517B/de active Pending
-
1965
- 1965-07-12 CH CH977565A patent/CH407035A/de unknown
- 1965-07-12 US US471397A patent/US3406032A/en not_active Expired - Lifetime
- 1965-07-14 NL NL656509087A patent/NL141258B/xx unknown
- 1965-07-14 AT AT645065A patent/AT256779B/de active
- 1965-07-14 SE SE09304/65A patent/SE334140B/xx unknown
- 1965-07-15 GB GB30139/65A patent/GB1116511A/en not_active Expired
- 1965-07-20 BE BE667153D patent/BE667153A/xx unknown
Patent Citations (5)
| 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)
| 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 |
Also Published As
| Publication number | Publication date |
|---|---|
| DE1290517B (de) | 1969-03-13 |
| NL6509087A (de) | 1966-01-24 |
| SE334140B (de) | 1971-04-19 |
| AT256779B (de) | 1967-09-11 |
| NL141258B (nl) | 1974-02-15 |
| GB1116511A (en) | 1968-06-06 |
| BE667153A (de) | 1965-11-16 |
| CH407035A (de) | 1966-02-15 |
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