EP0564346A1 - Veredlung von Textilien mit Phosphinicobernsteinsäure, Phosphinicobisbernsteinsäure oder deren Mischung enthaltenden Zusammensetzungen - Google Patents

Veredlung von Textilien mit Phosphinicobernsteinsäure, Phosphinicobisbernsteinsäure oder deren Mischung enthaltenden Zusammensetzungen Download PDF

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Publication number: EP0564346A1
Authority: EP; European Patent Office
Prior art keywords: acid; phosphinicobissuccinic; phosphinicosuccinic; textile; finishing
Prior art date: 1992-04-03
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

EP93400806A

Other languages

English (en)

French (fr)

Other versions

EP0564346B1 (de

Inventor

Didier Wilhelm

Antonio Gelabert

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.)

Clariant Finance BVI Ltd

Original Assignee

Francaise Hoechst Ste

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.)

1992-04-03

Filing date

1993-03-29

Publication date

1993-10-06

1993-03-29 Application filed by Francaise Hoechst Ste filed Critical Francaise Hoechst Ste

1993-10-06 Publication of EP0564346A1 publication Critical patent/EP0564346A1/de

1997-01-15 Application granted granted Critical

1997-01-15 Publication of EP0564346B1 publication Critical patent/EP0564346B1/de

2013-03-29 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

239000002253 acid Substances 0.000 title claims abstract description 56
239000004753 textile Substances 0.000 title claims abstract description 23
239000000203 mixture Substances 0.000 title claims abstract description 16
238000000034 method Methods 0.000 claims abstract description 9
229920002678 cellulose Polymers 0.000 claims abstract description 5
239000001913 cellulose Substances 0.000 claims abstract description 5
239000003431 cross linking reagent Substances 0.000 claims abstract description 3
150000008044 alkali metal hydroxides Chemical class 0.000 claims description 4
239000003054 catalyst Substances 0.000 claims description 2
238000009988 textile finishing Methods 0.000 claims 1
150000007513 acids Chemical class 0.000 abstract description 3
239000000243 solution Substances 0.000 description 31
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
239000000047 product Substances 0.000 description 13
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 12
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
239000012153 distilled water Substances 0.000 description 11
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
239000004744 fabric Substances 0.000 description 8
KWSLGOVYXMQPPX-UHFFFAOYSA-N 5-[3-(trifluoromethyl)phenyl]-2h-tetrazole Chemical compound FC(F)(F)C1=CC=CC(C2=NNN=N2)=C1 KWSLGOVYXMQPPX-UHFFFAOYSA-N 0.000 description 7
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 7
229910052708 sodium Inorganic materials 0.000 description 7
239000011734 sodium Substances 0.000 description 7
229910001379 sodium hypophosphite Inorganic materials 0.000 description 7
238000003756 stirring Methods 0.000 description 7
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 6
239000012071 phase Substances 0.000 description 6
230000037303 wrinkles Effects 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 5
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
239000007864 aqueous solution Substances 0.000 description 4
238000006243 chemical reaction Methods 0.000 description 4
ACVYVLVWPXVTIT-UHFFFAOYSA-M phosphinate Chemical compound [O-][PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-M 0.000 description 4
LCPVQAHEFVXVKT-UHFFFAOYSA-N 2-(2,4-difluorophenoxy)pyridin-3-amine Chemical compound NC1=CC=CN=C1OC1=CC=C(F)C=C1F LCPVQAHEFVXVKT-UHFFFAOYSA-N 0.000 description 3
-1 2-ethyl tert-butyl Chemical group 0.000 description 3
238000010438 heat treatment Methods 0.000 description 3
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 3
239000012429 reaction media Substances 0.000 description 3
CHQMHPLRPQMAMX-UHFFFAOYSA-L sodium persulfate Substances [Na+].[Na+].[O-]S(=O)(=O)OOS([O-])(=O)=O CHQMHPLRPQMAMX-UHFFFAOYSA-L 0.000 description 3
239000000725 suspension Substances 0.000 description 3
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
238000005481 NMR spectroscopy Methods 0.000 description 2
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
238000013019 agitation Methods 0.000 description 2
238000004458 analytical method Methods 0.000 description 2
239000008346 aqueous phase Substances 0.000 description 2
238000009835 boiling Methods 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
238000001816 cooling Methods 0.000 description 2
238000004132 cross linking Methods 0.000 description 2
LDCRTTXIJACKKU-ARJAWSKDSA-N dimethyl maleate Chemical compound COC(=O)\C=C/C(=O)OC LDCRTTXIJACKKU-ARJAWSKDSA-N 0.000 description 2
239000000675 fabric finishing Substances 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
238000009962 finishing (textile) Methods 0.000 description 2
ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical group O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 description 2
238000010992 reflux Methods 0.000 description 2
159000000000 sodium salts Chemical class 0.000 description 2
239000000080 wetting agent Substances 0.000 description 2
238000004383 yellowing Methods 0.000 description 2
NAWNZGXDXQECGO-UHFFFAOYSA-N (1,4-dimethoxy-1,4-dioxobutan-2-ylidene)-hydroxy-oxidophosphanium Chemical compound P(=O)(O)=C(C(=O)OC)CC(=O)OC NAWNZGXDXQECGO-UHFFFAOYSA-N 0.000 description 1
NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
INYFLFHWHIFXIF-UHFFFAOYSA-N 2-[(1,4-dimethoxy-1,4-dioxobutan-2-yl)-hydroxyphosphoryl]butanedioic acid Chemical compound COC(=O)CC(C(=O)OC)P(=O)(C(CC(=O)O)C(=O)O)O INYFLFHWHIFXIF-UHFFFAOYSA-N 0.000 description 1
DMPIBHMHWWHDLG-UHFFFAOYSA-N 2-[1,2-dicarboxyethyl(hydroxy)phosphoryl]butanedioic acid;sodium Chemical compound [Na].OC(=O)CC(C(O)=O)P(O)(=O)C(C(O)=O)CC(O)=O DMPIBHMHWWHDLG-UHFFFAOYSA-N 0.000 description 1
UDHXJZHVNHGCEC-UHFFFAOYSA-N Chlorophacinone Chemical compound C1=CC(Cl)=CC=C1C(C=1C=CC=CC=1)C(=O)C1C(=O)C2=CC=CC=C2C1=O UDHXJZHVNHGCEC-UHFFFAOYSA-N 0.000 description 1
229920000742 Cotton Polymers 0.000 description 1
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-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
238000007259 addition reaction Methods 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium peroxydisulfate Substances [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 1
VAZSKTXWXKYQJF-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)OOS([O-])=O VAZSKTXWXKYQJF-UHFFFAOYSA-N 0.000 description 1
229910001870 ammonium persulfate Inorganic materials 0.000 description 1
239000004176 azorubin Substances 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
150000001732 carboxylic acid derivatives Chemical group 0.000 description 1
125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 description 1
239000003729 cation exchange resin Substances 0.000 description 1
230000003750 conditioning effect Effects 0.000 description 1
238000004821 distillation Methods 0.000 description 1
150000002148 esters Chemical group 0.000 description 1
239000000835 fiber Substances 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
239000011707 mineral Substances 0.000 description 1
229920000847 nonoxynol Polymers 0.000 description 1
SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical class CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
150000002978 peroxides Chemical class 0.000 description 1
JRKICGRDRMAZLK-UHFFFAOYSA-L peroxydisulfate Chemical compound [O-]S(=O)(=O)OOS([O-])(=O)=O JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 1
238000004313 potentiometry Methods 0.000 description 1
238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
230000005855 radiation Effects 0.000 description 1
238000000926 separation method Methods 0.000 description 1
238000004513 sizing Methods 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000001384 succinic acid Substances 0.000 description 1
239000013589 supplement Substances 0.000 description 1
238000005406 washing Methods 0.000 description 1
238000005303 weighing Methods 0.000 description 1
239000002023 wood Substances 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
- D06M13/244—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 sulfur or phosphorus
- D06M13/282—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 sulfur or phosphorus with compounds containing phosphorus
- D06M13/285—Phosphines; Phosphine oxides; Phosphine sulfides; Phosphinic or phosphinous acids or derivatives thereof
- 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
- Y10T442/2369—Coating or impregnation improves elasticity, bendability, resiliency, flexibility, or shape retention of the fabric
- Y10T442/2393—Coating or impregnation provides crease-resistance or wash and wear characteristics

Definitions

the present invention relates to a fabric finishing process, a fabric finishing bath using phosphinicosuccinic acid, phosphinicobissuccinic acid or mixtures thereof, finished textiles and the use of said acids as finishes.
Textile finishes are currently commonly used to impart wrinkle-resistant properties to cellulosic fabrics, but most contain free or combined formaldehyde, which is released either in the sizing workshops, or when the fabrics so finished are used.
Phosphinicosuccinic acid (I) as well as phosphinicobissuccinic acid (II) are described in the literature (United States patent No. 5018577). They are obtained in particular by adding an alkali metal hypophosphite such as sodium hypophosphite to maleic acid, a dialkyl maleate or maleic anhydride followed, if necessary, by acid or basic hydrolysis of the ester functions, when a dialkyl maleate is used as the starting product.
This addition reaction is generally catalyzed with a mineral peroxide derivative such as sodium persulfate, or an organic derivative such as 2-ethyl tert-butyl perhexanoate, TBPEH; it can also be carried out under ultraviolet radiation within acetone (French patent No. 2,356,658, United States patents 4138431, 4590014, 4632741, 5023000, 5018577, 4088678 and Beil. IV, 4th supplement, page 3497, 1959).
a mineral peroxide derivative such as sodium persulfate
organic derivative such as 2-ethyl tert-butyl perhexanoate
Phosphinicosuccinic acid (I) and phosphinicobissuccinic acid (II), as well as their mixtures in variable proportions, have, as has been said previously, very interesting properties of crosslinking of cellulose, which justify their application as 'textile finishes, to give cellulosic fabrics wrinkle-resistant properties.
the present invention therefore relates to a process for finishing textiles, characterized in that the textile to be treated is impregnated using a finishing bath comprising phosphinicosuccinic acid (I), acid phosphinicobissuccinic (II), or a mixture of these two acids. This mixture can be in variable proportions.
the textile dressing bath is partially neutralized with an alkali metal hydroxide in order to obtain a dressing bath having a pH of 2 to 7.
the finishes described above are characterized in that they do not contain any catalyst of any kind.
the present application also relates to a finishing bath for textiles, characterized in that it comprises a solution of phosphinicosuccinic acid (I), phosphinicobissuccinic acid (II), or their mixture partially neutralized at pH 2 at 7 using an alkali metal hydroxide, and in particular the baths described in the examples.
a finishing bath for textiles characterized in that it comprises a solution of phosphinicosuccinic acid (I), phosphinicobissuccinic acid (II), or their mixture partially neutralized at pH 2 at 7 using an alkali metal hydroxide, and in particular the baths described in the examples.
the above solutions are preferably aqueous solutions; they are advantageously added with a wetting agent well known from the state of the art.
the present application also relates to finished textiles, characterized in that they are obtained by the implementation of the process described above.
the present application also relates to the use, as a textile finish, of phosphinicosuccinic acid (I), of phosphinicobissuccinic acid (II), or of a mixture thereof.
the present application finally relates to the use of phosphinicosuccinic acid (I), phosphinicobissuccinic acid (II) or their mixtures in variable proportions, as crosslinking agents for the cellulose contained in particular in fibers textiles, wood chips, sawdust.
the wrinkle test is carried out according to the AATCC 66-1972 standard on samples as they are and on samples subjected to three household washes at 60 ° C; the crease resistance is expressed by the sum of the crease angles obtained in warp direction and in weft direction.
the tensile strength of the samples expressed in daN in the warp direction plus in the weft direction is produced according to standard AFNOR G 07.001.
the yellowing of the tissues carried out on a FIXOTEST device at 200 ° C for 30 seconds and the whiteness expressed in Berger degrees, are measured with a spectrophotometer.
the residual formaldehyde level on tissue was determined according to the method described in Japanese law 112-1973; in the fabrics of the examples, no formaldehyde could be detected.
This product dosed by potentiometry, contains 15.49 meq / g of acid functions, of which 2.756 meq / g of strong acid functions, or a ratio between carboxylic acid function and phosphinic acid function of 4.62: 1 (theory 4: 1).
a 100% cotton poplin fabric, scalded and bleached, is impregnated with the scarf, weighing approximately 130 g per square meter with a rate of expression of 75% in an aqueous bath, the pH of which has been adjusted with soda at the value indicated in table I, containing in solution the quantities of acid, as well as 2 g per liter of ethoxylated nonylphenol with 10 moles of ethylene oxide as wetting agent.
the fabric is then dried for 45 seconds at 120 ° C, then it is subjected on a laboratory oar to a heat treatment for 90 seconds at 180 ° C.
Comparison example C1 corresponds to the untreated tissue.
Example 5 is repeated, replacing the sodium persulfate with an equivalent quantity of ammonium persulfate. This gives about 1464 g of a clear, colorless aqueous solution containing about 2.5 moles of phosphinicobissuccinic acid monosodium, having an acidity of 6.96 meq / g (theory 6.83 meq / g) and no longer containing maleic anhydride determined by NMR analysis of the proton and carbon thirteen.
This solution, designated E is used in this form in Example 9.

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Engineering & Computer Science (AREA)
Textile Engineering (AREA)
Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Compositions Of Macromolecular Compounds (AREA)

EP93400806A 1992-04-03 1993-03-29 Veredlung von Textilien mit Phosphinicobernsteinsäure, Phosphinicobisbernsteinsäure oder deren Mischung enthaltenden Zusammensetzungen Expired - Lifetime EP0564346B1 (de)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
FR9204076A FR2689529B1 (fr)	1992-04-03	1992-04-03	Procede d'appretage de textiles, bain d'appretage pour textiles utilisant de l'acide phosphinicosuccinique, de l'acide phosphinicobisuccinique ou leurs melanges.
FR9204076		1992-04-03

Publications (2)

Publication Number	Publication Date
EP0564346A1 true EP0564346A1 (de)	1993-10-06
EP0564346B1 EP0564346B1 (de)	1997-01-15

Family

ID=9428441

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
EP93400806A Expired - Lifetime EP0564346B1 (de)	1992-04-03	1993-03-29	Veredlung von Textilien mit Phosphinicobernsteinsäure, Phosphinicobisbernsteinsäure oder deren Mischung enthaltenden Zusammensetzungen

Country Status (12)

Country	Link
US (2)	US5300240A (de)
EP (1)	EP0564346B1 (de)
JP (1)	JP3217894B2 (de)
KR (1)	KR100257986B1 (de)
AT (1)	ATE147805T1 (de)
CA (1)	CA2091656A1 (de)
DE (1)	DE69307375T2 (de)
DK (1)	DK0564346T3 (de)
ES (1)	ES2096235T3 (de)
FR (1)	FR2689529B1 (de)
GR (1)	GR3022662T3 (de)
TR (1)	TR26711A (de)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0976867A1 (de) *	1998-07-31	2000-02-02	Clariant (France) S.A.	Verfahren zur Veredlung von Textilien sowie Veredlungsbäder
CN1743532B (zh) *	2004-09-03	2010-05-26	株式会社岛精机制作所	纤维制品染色的预处理方法、预处理剂、染色方法及进行过预处理的纤维制品
CN109137526A (zh) *	2018-08-30	2019-01-04	常州大学	一种无甲醛抗皱整理剂的制备方法及应用
US11149202B1 (en)	2016-12-13	2021-10-19	Ecolab Usa Inc.	Tetracarboxylic acid combinations for corrosion inhibition

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* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2689529B1 (fr) *	1992-04-03	1995-06-23	Hoechst France	Procede d'appretage de textiles, bain d'appretage pour textiles utilisant de l'acide phosphinicosuccinique, de l'acide phosphinicobisuccinique ou leurs melanges.
US5496477A (en) *	1992-12-21	1996-03-05	Ppg Industries, Inc.	Non-formaldehyde durable press finishing for cellulosic textiles with phosphinocarboxylic acid
US5496476A (en) *	1992-12-21	1996-03-05	Ppg Indutstries, Inc.	Non-formaldehyde durable press finishing for cellulosic textiles with phosphonoalkylpolycarboxylic acid
US7169293B2 (en) *	1999-08-20	2007-01-30	Uop Llc	Controllable space velocity reactor and process
WO2001051496A1 (en) *	2000-01-14	2001-07-19	Rhodia, Inc.	Crosslinking agents for textile finishing baths
US6989035B2 (en) *	2001-10-18	2006-01-24	The Procter & Gamble Company	Textile finishing composition and methods for using same
US7018422B2 (en)	2001-10-18	2006-03-28	Robb Richard Gardner	Shrink resistant and wrinkle free textiles
US7144431B2 (en)	2001-10-18	2006-12-05	The Procter & Gamble Company	Textile finishing composition and methods for using same
US7169742B2 (en)	2001-10-18	2007-01-30	The Procter & Gamble Company	Process for the manufacture of polycarboxylic acids using phosphorous containing reducing agents
US7008457B2 (en) *	2001-10-18	2006-03-07	Mark Robert Sivik	Textile finishing composition and methods for using same
US6841198B2 (en)	2001-10-18	2005-01-11	Strike Investments, Llc	Durable press treatment of fabric
SG153838A1 (en) *	2004-06-24	2009-07-29	Dow Global Technologies Inc	Stretch fabrics with wrinkle resistance
JP2006316372A (ja) *	2005-05-11	2006-11-24	Tokai Senko Kk	セルロース系繊維の洗濯変色防止加工方法
JP2010511800A (ja) *	2006-11-30	2010-04-15	ダウグローバルテクノロジーズインコーポレイティド	防皺性を有する伸縮性布地のためのオレフィンブロック組成物
US9023784B2 (en)	2012-09-13	2015-05-05	Ecolab Usa Inc.	Method of reducing soil redeposition on a hard surface using phosphinosuccinic acid adducts
US9752105B2 (en)	2012-09-13	2017-09-05	Ecolab Usa Inc.	Two step method of cleaning, sanitizing, and rinsing a surface
US8871699B2 (en)	2012-09-13	2014-10-28	Ecolab Usa Inc.	Detergent composition comprising phosphinosuccinic acid adducts and methods of use
US8748365B2 (en)	2012-09-13	2014-06-10	Ecolab Usa Inc.	Solidification matrix comprising phosphinosuccinic acid derivatives
US20140308162A1 (en)	2013-04-15	2014-10-16	Ecolab Usa Inc.	Peroxycarboxylic acid based sanitizing rinse additives for use in ware washing
US9994799B2 (en)	2012-09-13	2018-06-12	Ecolab Usa Inc.	Hard surface cleaning compositions comprising phosphinosuccinic acid adducts and methods of use

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US3300337A (en) *	1960-10-06	1967-01-24	Stauffer Chemical Co	Anti-static coated textile fiber
US3535073A (en) *	1967-10-25	1970-10-20	Us Agriculture	Crosslinking cotton with haloalkyl phosphine oxides
US3979533A (en) *	1972-12-04	1976-09-07	The United States Of America As Represented By The Secretary Of Agriculture	α,α'-Bis-(phosphono)dicarboxylic acid derivatives
EP0484196A1 (de) *	1990-10-30	1992-05-06	Societe Francaise Hoechst	Neue Derivate von Phosphonalkanpolykarboxylsäuren und deren Verwendung

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1993
- 1993-03-15 CA CA002091656A patent/CA2091656A1/fr not_active Abandoned
- 1993-03-29 DE DE69307375T patent/DE69307375T2/de not_active Expired - Lifetime
- 1993-03-29 EP EP93400806A patent/EP0564346B1/de not_active Expired - Lifetime
- 1993-03-29 AT AT93400806T patent/ATE147805T1/de active
- 1993-03-29 DK DK93400806.1T patent/DK0564346T3/da active
- 1993-03-29 ES ES93400806T patent/ES2096235T3/es not_active Expired - Lifetime
- 1993-04-01 TR TR93/0260A patent/TR26711A/xx unknown
- 1993-04-02 JP JP10017593A patent/JP3217894B2/ja not_active Expired - Fee Related
- 1993-04-02 US US08/041,463 patent/US5300240A/en not_active Expired - Lifetime
1994
- 1994-01-24 US US08/185,149 patent/US5385680A/en not_active Expired - Lifetime
1997
- 1997-02-26 GR GR970400349T patent/GR3022662T3/el unknown
1998
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Publication number	Priority date	Publication date	Assignee	Title
EP0976867A1 (de) *	1998-07-31	2000-02-02	Clariant (France) S.A.	Verfahren zur Veredlung von Textilien sowie Veredlungsbäder
FR2781821A1 (fr) *	1998-07-31	2000-02-04	Clariant France Sa	Procede pour appreter un textile et bains d'appretage
US6277152B1 (en)	1998-07-31	2001-08-21	Clariant (France) S.A.	Process for finishing a textile and finishing baths
CN1743532B (zh) *	2004-09-03	2010-05-26	株式会社岛精机制作所	纤维制品染色的预处理方法、预处理剂、染色方法及进行过预处理的纤维制品
US11149202B1 (en)	2016-12-13	2021-10-19	Ecolab Usa Inc.	Tetracarboxylic acid combinations for corrosion inhibition
CN109137526A (zh) *	2018-08-30	2019-01-04	常州大学	一种无甲醛抗皱整理剂的制备方法及应用
CN109137526B (zh) *	2018-08-30	2021-01-29	常州大学	一种无甲醛抗皱整理剂的制备方法及应用

Also Published As

Publication number	Publication date
US5300240A (en)	1994-04-05
KR100257986B1 (en)	2000-06-01
DE69307375D1 (de)	1997-02-27
FR2689529B1 (fr)	1995-06-23
EP0564346B1 (de)	1997-01-15
KR930021876A (ko)	1993-11-23
JP3217894B2 (ja)	2001-10-15
JPH0633374A (ja)	1994-02-08
DE69307375T2 (de)	1997-05-15
CA2091656A1 (fr)	1993-10-04
US5385680A (en)	1995-01-31
ATE147805T1 (de)	1997-02-15
FR2689529A1 (fr)	1993-10-08
DK0564346T3 (da)	1997-07-07
GR3022662T3 (en)	1997-05-31
ES2096235T3 (es)	1997-03-01
TR26711A (tr)	1995-05-15

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Publication	Publication Date	Title
EP0564346B1 (de)	1997-01-15	Veredlung von Textilien mit Phosphinicobernsteinsäure, Phosphinicobisbernsteinsäure oder deren Mischung enthaltenden Zusammensetzungen
DE2238734C2 (de)	1983-02-17	Bis-benzofuranyl-Verbindungen und deren Verwendung als optische Aufheller
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AT500342B1 (de)	2006-08-15	Verfahren zur herstellung von acetyliertem holz
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