EP1133596A1 - Agent impermeabilisant pour appret de textiles - Google Patents

Agent impermeabilisant pour appret de textiles

Info

Publication number: EP1133596A1
Authority: EP; European Patent Office
Prior art keywords: branched; unbranched; amounts; carbon atoms; fatty
Prior art date: 1998-11-28
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.): Granted

Application number

EP99959286A

Other languages

German (de)

English (en)

Other versions

EP1133596B1 (fr

Inventor

Bernd Wahle

Ludwig BÖNNIGER

Wolfgang TÜRK

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.)

Cognis IP Management GmbH

Original Assignee

Cognis Deutschland GmbH and Co KG

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.)

1998-11-28

Filing date

1999-11-19

Publication date

2001-09-19

1999-11-19 Application filed by Cognis Deutschland GmbH and Co KG filed Critical Cognis Deutschland GmbH and Co KG

2001-09-19 Publication of EP1133596A1 publication Critical patent/EP1133596A1/fr

2004-03-17 Application granted granted Critical

2004-03-17 Publication of EP1133596B1 publication Critical patent/EP1133596B1/fr

2019-11-19 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

238000009988 textile finishing Methods 0.000 title claims description 5
238000004078 waterproofing Methods 0.000 title 1
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 12
239000000839 emulsion Substances 0.000 claims abstract description 11
150000003754 zirconium Chemical class 0.000 claims abstract description 9
150000002576 ketones Chemical class 0.000 claims abstract description 7
235000014113 dietary fatty acids Nutrition 0.000 claims abstract description 5
229930195729 fatty acid Natural products 0.000 claims abstract description 5
239000000194 fatty acid Substances 0.000 claims abstract description 5
150000004665 fatty acids Chemical class 0.000 claims abstract description 5
150000002191 fatty alcohols Chemical class 0.000 claims abstract description 5
150000002148 esters Chemical class 0.000 claims abstract description 4
150000001983 dialkylethers Chemical class 0.000 claims abstract description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 20
239000003795 chemical substances by application Substances 0.000 claims description 19
239000004753 textile Substances 0.000 claims description 16
239000000126 substance Substances 0.000 claims description 14
239000005871 repellent Substances 0.000 claims description 13
230000002940 repellent Effects 0.000 claims description 12
230000002209 hydrophobic effect Effects 0.000 claims description 9
238000000034 method Methods 0.000 claims description 5
DUFCMRCMPHIFTR-UHFFFAOYSA-N 5-(dimethylsulfamoyl)-2-methylfuran-3-carboxylic acid Chemical compound CN(C)S(=O)(=O)C1=CC(C(O)=O)=C(C)O1 DUFCMRCMPHIFTR-UHFFFAOYSA-N 0.000 claims description 3
150000005215 alkyl ethers Chemical class 0.000 claims description 2
239000000203 mixture Substances 0.000 abstract description 7
239000002245 particle Substances 0.000 abstract description 4
150000001875 compounds Chemical class 0.000 abstract description 2
150000002170 ethers Chemical class 0.000 description 6
239000012188 paraffin wax Substances 0.000 description 5
-1 polysiloxanes Polymers 0.000 description 5
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
239000000835 fiber Substances 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
NOPFSRXAKWQILS-UHFFFAOYSA-N docosan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCCCCCO NOPFSRXAKWQILS-UHFFFAOYSA-N 0.000 description 2
UKMSUNONTOPOIO-UHFFFAOYSA-N docosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCC(O)=O UKMSUNONTOPOIO-UHFFFAOYSA-N 0.000 description 2
239000003995 emulsifying agent Substances 0.000 description 2
239000004744 fabric Substances 0.000 description 2
YCOZIPAWZNQLMR-UHFFFAOYSA-N pentadecane Chemical compound CCCCCCCCCCCCCCC YCOZIPAWZNQLMR-UHFFFAOYSA-N 0.000 description 2
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
239000002994 raw material Substances 0.000 description 2
IIYFAKIEWZDVMP-UHFFFAOYSA-N tridecane Chemical compound CCCCCCCCCCCCC IIYFAKIEWZDVMP-UHFFFAOYSA-N 0.000 description 2
RSJKGSCJYJTIGS-UHFFFAOYSA-N undecane Chemical compound CCCCCCCCCCC RSJKGSCJYJTIGS-UHFFFAOYSA-N 0.000 description 2
HLZKNKRTKFSKGZ-UHFFFAOYSA-N 1-Tetradecanol Natural products CCCCCCCCCCCCCCO HLZKNKRTKFSKGZ-UHFFFAOYSA-N 0.000 description 1
JPPRXACMNPYJNK-UHFFFAOYSA-N 1-docosoxydocosane Chemical compound CCCCCCCCCCCCCCCCCCCCCCOCCCCCCCCCCCCCCCCCCCCCC JPPRXACMNPYJNK-UHFFFAOYSA-N 0.000 description 1
HBXWUCXDUUJDRB-UHFFFAOYSA-N 1-octadecoxyoctadecane Chemical compound CCCCCCCCCCCCCCCCCCOCCCCCCCCCCCCCCCCCC HBXWUCXDUUJDRB-UHFFFAOYSA-N 0.000 description 1
HANWHVWXFQSQGJ-UHFFFAOYSA-N 1-tetradecoxytetradecane Chemical compound CCCCCCCCCCCCCCOCCCCCCCCCCCCCC HANWHVWXFQSQGJ-UHFFFAOYSA-N 0.000 description 1
RASARYSDGUNLQR-UHFFFAOYSA-N 7-ethyl-7-(7-ethylhexacosan-7-yloxy)hexacosane Chemical group CCCCCCCCCCCCCCCCCCCC(CC)(CCCCCC)OC(CC)(CCCCCC)CCCCCCCCCCCCCCCCCCC RASARYSDGUNLQR-UHFFFAOYSA-N 0.000 description 1
235000021357 Behenic acid Nutrition 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
229920000742 Cotton Polymers 0.000 description 1
101500021084 Locusta migratoria 5 kDa peptide Proteins 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
229910052782 aluminium Inorganic materials 0.000 description 1
BTFJIXJJCSYFAL-UHFFFAOYSA-N arachidyl alcohol Natural products CCCCCCCCCCCCCCCCCCCCO BTFJIXJJCSYFAL-UHFFFAOYSA-N 0.000 description 1
125000001204 arachidyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
229940116226 behenic acid Drugs 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
238000004140 cleaning Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
238000006356 dehydrogenation reaction Methods 0.000 description 1
229940085632 distearyl ether Drugs 0.000 description 1
229960000735 docosanol Drugs 0.000 description 1
125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
238000001035 drying Methods 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
KEMQGTRYUADPNZ-UHFFFAOYSA-N heptadecanoic acid Chemical compound CCCCCCCCCCCCCCCCC(O)=O KEMQGTRYUADPNZ-UHFFFAOYSA-N 0.000 description 1
IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 1
VKOBVWXKNCXXDE-UHFFFAOYSA-N icosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCC(O)=O VKOBVWXKNCXXDE-UHFFFAOYSA-N 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 1
BXWNKGSJHAJOGX-UHFFFAOYSA-N n-hexadecyl alcohol Natural products CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 1
GLDOVTGHNKAZLK-UHFFFAOYSA-N n-octadecyl alcohol Natural products CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 1
FBUKVWPVBMHYJY-UHFFFAOYSA-N nonanoic acid Chemical compound CCCCCCCCC(O)=O FBUKVWPVBMHYJY-UHFFFAOYSA-N 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000011049 pearl Substances 0.000 description 1
239000004014 plasticizer Substances 0.000 description 1
229920001296 polysiloxane Polymers 0.000 description 1
239000000047 product Substances 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
150000003333 secondary alcohols Chemical class 0.000 description 1
239000012748 slip agent Substances 0.000 description 1
239000002904 solvent Substances 0.000 description 1
125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 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
- D06M13/10—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 oxygen
- D06M13/184—Carboxylic acids; Anhydrides, halides or salts thereof
- D06M13/188—Monocarboxylic acids; Anhydrides, halides or salts thereof
- 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
- D06M13/10—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 oxygen
- D06M13/12—Aldehydes; Ketones
- D06M13/127—Mono-aldehydes, e.g. formaldehyde; Monoketones
- 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
- D06M13/10—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 oxygen
- D06M13/165—Ethers
- 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
- D06M13/10—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 oxygen
- D06M13/224—Esters of carboxylic acids; Esters of carbonic acid
- 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
- D06M2200/00—Functionality of the treatment composition and/or properties imparted to the textile material
- D06M2200/10—Repellency against liquids
- D06M2200/12—Hydrophobic properties

Definitions

the present application relates to water repellents for textile finishing, a process for the hydrophobic finishing of textiles and the use of certain fatty substances as water repellents.
hydrophobic finishing of textiles water repellents based on polysiloxanes, fluorocarbons or mixtures of aluminum or zirconium salts with paraffins are generally used (compare “Handbuch der Textilhilhilstoff”, A. Chwala, V. Anger, Verlag Chemie, New York 1977, Chapter 3.24 "Phobierstoff", page 735 ff).
the hydrophobic finishing of textiles serves to make them either water-repellent or water-impermeable.
the hydrophobizing agent is applied to the fibers of the textiles and is arranged there so that the hydrophobic parts of the molecule are perpendicular to the fiber surface. In this way, the tendency of the water to spread over the entire surface is greatly reduced.
the water takes on the spherical shape due to the cohesive forces and pearls off the textile surface.
hydrophobizing agents described in the prior art in particular the zirconium salt-containing paraffin emulsions, such as are described, for example, in DD-A1-218 564, enable sufficient hydrophobization of textile fabrics, there is the problem that such agents are not or not sufficiently biodegradable are.
paraffin emulsions when such paraffin emulsions are applied via a padder, paraffin deposits are observed on the paddle rollers after a longer period of time, which make cleaning the rollers and thus a costly interruption of the production process necessary.
hydrophobizing compositions which meet all the application requirements of the textile industry - in particular cause little or no deposits on the machine parts and at the same time are biodegradable.
a hydrophobizing agent for textile finishing which contains a zirconium salt in combination with a fatty substance, which is selected from the group of a) branched or unbranched, symmetrical or asymmetrical dialkyl ether with a total of 8 to 44 carbon atoms and / or the b) esters of branched or unbranched C12-22 fatty acids with branched or unbranched C-8-22 fatty alcohols and / or c) branched or unbranched, symmetrical or unsymmetrical dialkyl ketones with a total of 8 to 44 C atoms.
a fatty substance which is selected from the group of a) branched or unbranched, symmetrical or asymmetrical dialkyl ether with a total of 8 to 44 carbon atoms and / or the b) esters of branched or unbranched C12-22 fatty acids with branched or unbranched C-8-22 fatty alcohols and / or c) branched or unbranched,
Zirconium acetate is particularly preferred.
the fatty substances are known alkyl ethers of the general formula R 1 -0-R 2 , where R 1 and R 2 each represent alkyl radicals having 1 to 22 carbon atoms. The total number of carbon atoms in the molecule is 8 to 44. Both symmetrical ethers, ie R 1 and R 2 are identical, or unsymmetrical ethers (R 1 ⁇ R 2 ) can be used.
the alkyl radicals R 1 and R 2 can be saturated, unsaturated, branched or unbranched. Those ethers whose radicals R 1 or R 2 have a C chain length of 10 to 22 are particularly preferred.
the total carbon number of the ethers is preferably 20 to 44.
Preferred ethers are, for example, dibehenyl ether, distearyl ether, dipalmityl ether or dimyristyl ether.
An example of an asymmetrical ether is ethylhexyleicosyl ether.
the ethers can be prepared by all known technical processes.
esters of branched or unbranched C12-22 fatty acids with branched or unbranched C8-22 fatty alcohols are suitable.
Suitable fatty acids are, for example, caprylic, pearlagon, capric, undecane, tridecane, myristic, pentadecane, palmitic, heptadecanoic, octadecanoic, nonanoic, arachic or behenic acid.
Suitable fatty acids are, for example, caprylic, pearlagon, capric, undecane, tridecane, myristic, pentadecane, palmitic, heptadecanoic, octadecanoic, nonanoic, arachic or behenic acid.
Fatty alcohols are, for example, capryl-caprin, lauryl, myristyl, palmityl, stearyl, arachidyl or Behenyl alcohol.
the water repellents can contain dialkyl ketones of the formula R 3 -CO-R 4 with a total of 8 to 44 carbon atoms.
alkyl methyl ketones such as octanonanon-2, nonanon-2, undecanon-2, dodecanon-2, tridecanon-2, tetradecanon-2, pentadecanon-2, heptadecanon-2, octadecanon-2, nonadecanon-2, pentadecanon-2, Heptadecanon-2, Octadecanon-2, Nonadecanon-2, Eicosanon-2 or Dodecasanon-2 can be used.
Symmetrical ketones such as Undecanon-6, Tridecanon-7, Pentadecanon-8, Heptadecanon-9, Nonadecanon-10, Tricosanon-12, Hentriacontanon-16, Pentatricanon-18, Nonatricontanon-20 or Triatetracontanon-22 are also suitable.
the ketones can be prepared by all methods known to those skilled in the art, for example by oxidation or dehydrogenation of secondary alcohols.
the water repellents according to the invention are preferably in the form of an aqueous emulsion. Water is then contained in amounts between 10 and 90% by weight.
the compositions preferably contain 30 to 80% by weight and in particular 40 to 60% by weight of water.
the zirconium salts are generally present in amounts of 1 to 20% by weight, preferably in amounts of 5 to 15% by weight and in particular in amounts of 5 to 10% by weight.
the fatty substances a) to c) are preferably present in the compositions in amounts of 10 to 95% by weight, in particular in amounts of 15 to 60% by weight and particularly preferably in amounts of 10 to 30% by weight.
the agents can contain other suitable ingredients in addition to the salts and the fatty substances, in particular emulsifiers, but also anti-slip agents, wet fastness improvers, grip products, plasticizers, solvents, for example ethanol, n-propanol or i-propanol and pH regulators such as organic acids or bases.
the pH of the aqueous emulsions is in the acidic range, preferably it is less than 4.5 and in particular it is in the range from 2.0 to 3.5.
the auxiliary substances are present in minor amounts between 0.5 and 5% by weight. As a rule, the agents according to the invention contain such auxiliaries in total in amounts of at most 10 wt.
the agents according to the invention are produced in a manner known per se by mixing the raw materials with water, heating them to temperatures between 40 and 90 ° C. and homogenizing them. Average particle sizes of less than 250 nm should be achieved. The average particle sizes are preferably in the range from 100 to 200 nm. After cooling, they can be used without further treatment.
the agents are usually in the form of an aqueous emulsion Applied to the textiles with the help of a foulard.
the agents according to the invention are suitable for the hydrophobic finishing of textiles made of synthetic or natural fibers, especially for cotton textiles.
a process for the hydrophobic finishing of textiles is claimed, agents according to the above description being suitably applied to the textiles. Furthermore, the use of these agents for the hydrophobic finishing of textiles is claimed.
Emulsifier 2.8% by weight
the agents were prepared as follows: The raw materials were presented, heated to 85 ° C. and homogenized. The agents were then cooled to 20 ° C.
the agents had pH values in the range from 2.8 to 3.0.
the particle size was in the range from 200 to 250 nm.
the Schopper test was carried out in accordance with DIN EN 20811: test fabric 100% CO (approx. 300 g / m 2 ), equipped with 150 g / l emulsion. Fleet intake 86%. Drying at 140 ° C.
the friction resistance was tested with a continuous runner with 120 g / l liquor, 5 bar pressure and a speed of 20 m / minute.
the friction resistance was interrupted when deposits on the paddle roller were recognizable:

Landscapes

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

EP99959286A 1998-11-28 1999-11-19 Agent impermeabilisant pour appret de textiles Expired - Lifetime EP1133596B1 (fr)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
DE19855081A DE19855081A1 (de)	1998-11-28	1998-11-28	Hydrophobiermittel für die Textilausrüstung
DE19855081		1998-11-28
PCT/EP1999/008886 WO2000032866A1 (fr)	1998-11-28	1999-11-19	Agent impermeabilisant pour appret de textiles

Publications (2)

Publication Number	Publication Date
EP1133596A1 true EP1133596A1 (fr)	2001-09-19
EP1133596B1 EP1133596B1 (fr)	2004-03-17

Family

ID=7889426

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
EP99959286A Expired - Lifetime EP1133596B1 (fr)	1998-11-28	1999-11-19	Agent impermeabilisant pour appret de textiles

Country Status (8)

Country	Link
US (1)	US6506316B1 (fr)
EP (1)	EP1133596B1 (fr)
AT (1)	ATE262068T1 (fr)
DE (2)	DE19855081A1 (fr)
DK (1)	DK1133596T3 (fr)
ES (1)	ES2219087T3 (fr)
PT (1)	PT1133596E (fr)
WO (1)	WO2000032866A1 (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE102005051589A1 (de) *	2005-10-27	2007-05-03	Wacker Polymer Systems Gmbh & Co. Kg	Fettsäureanhydride enthaltende Dispersionspulver
EP3450517A1 (fr) *	2017-08-30	2019-03-06	Govi	Objets composites en bois

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE218564C (fr)
US2635055A (en)	1948-07-08	1953-04-14	Hans G Figdor	Water repellent composition
DE905846C (de) *	1951-06-28	1954-03-08	Bayer Ag	Hydrophobierverfahren
FR1068657A (fr)	1951-06-28	1954-06-30	Bayer Ag	Procédé pour rendre hydrofuges des textiles, etc.
NL107002C (fr) *	1952-06-04	1900-01-01
US2759851A (en)	1954-01-29	1956-08-21	American Cyanamid Co	Water-repellent treatment for hydrophobic textile materials
NL125880C (fr)	1960-07-05	1900-01-01

1998
- 1998-11-28 DE DE19855081A patent/DE19855081A1/de not_active Withdrawn
1999
- 1999-11-19 WO PCT/EP1999/008886 patent/WO2000032866A1/fr not_active Ceased
- 1999-11-19 DE DE59908912T patent/DE59908912D1/de not_active Expired - Fee Related
- 1999-11-19 EP EP99959286A patent/EP1133596B1/fr not_active Expired - Lifetime
- 1999-11-19 ES ES99959286T patent/ES2219087T3/es not_active Expired - Lifetime
- 1999-11-19 DK DK99959286T patent/DK1133596T3/da active
- 1999-11-19 PT PT99959286T patent/PT1133596E/pt unknown
- 1999-11-19 US US09/856,674 patent/US6506316B1/en not_active Expired - Fee Related
- 1999-11-19 AT AT99959286T patent/ATE262068T1/de not_active IP Right Cessation

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO0032866A1 *

Also Published As

Publication number	Publication date
DE19855081A1 (de)	2000-05-31
ES2219087T3 (es)	2004-11-16
WO2000032866A1 (fr)	2000-06-08
US6506316B1 (en)	2003-01-14
ATE262068T1 (de)	2004-04-15
EP1133596B1 (fr)	2004-03-17
PT1133596E (pt)	2004-07-30
DE59908912D1 (de)	2004-04-22
DK1133596T3 (da)	2004-07-05

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DE1195265B (de)	1965-06-24	Verfahren zur antistatischen, weichmachenden und baktericiden Ausruestung von Geweben
DE3612479A1 (de)	1987-10-15	Waessriges konzentriertes textilweichmachungsmittel
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EP0491248B1 (fr)	1995-02-22	Produit pour le traitement de matériaux fibreux
EP0131865B1 (fr)	1988-09-07	Composés d'ammonium quaternaire oxalkylés estérifiés, procédé pour leur fabrication et leur utilisation comme agent de traitement pour fibres
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DE4133358A1 (de)	1993-04-15	Waessrige zusammensetzungen mit stickstoffhaltigen polysiloxanen
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