EP0399706B1 - Procédé de traitement de matériaux fibreux - Google Patents

Procédé de traitement de matériaux fibreux Download PDF

Info

Publication number
EP0399706B1
EP0399706B1 EP19900305117 EP90305117A EP0399706B1 EP 0399706 B1 EP0399706 B1 EP 0399706B1 EP 19900305117 EP19900305117 EP 19900305117 EP 90305117 A EP90305117 A EP 90305117A EP 0399706 B1 EP0399706 B1 EP 0399706B1
Authority
EP
European Patent Office
Prior art keywords
reaction product
denotes
organopolysiloxane
piece
examples
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
Application number
EP19900305117
Other languages
German (de)
English (en)
Other versions
EP0399706A2 (fr
EP0399706A3 (fr
Inventor
Stephen Edward Cray
Franck André Daniel Renauld
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.)
Dow Silicones UK Ltd
Original Assignee
Dow Corning Ltd
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.)
Filing date
Publication date
Family has litigation
First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=10657290&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=EP0399706(B1) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Application filed by Dow Corning Ltd filed Critical Dow Corning Ltd
Publication of EP0399706A2 publication Critical patent/EP0399706A2/fr
Publication of EP0399706A3 publication Critical patent/EP0399706A3/fr
Application granted granted Critical
Publication of EP0399706B1 publication Critical patent/EP0399706B1/fr
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

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
    • D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
    • D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/643—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing silicon in the main chain
    • D06M15/6436—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing silicon in the main chain containing amino groups

Definitions

  • This invention relates to a method of treating fibrous materials and more specifically to a method of treating textile materials.
  • fibrous materials is meant fibres of synthetic or naturally occurring materials, for example wool, cotton, polyester, carbon and blends of these.
  • the invention relates to the treatment of the fibres as such as well as to the treatment of fabrics or textiles incorporating the fibres.
  • compositions comprising amine-containing silicon compounds for imparting desirable properties, e.g. softness, water repellency, lubricity and crease resistance thereto.
  • the GB-A-1 491 747 for example provides a composition for treatment of synthetic fibres which comprises 1 part of certain aminosilanes and 1 to 20 parts of certain epoxysiloxanes.
  • the GB-A-1 296 136 provides a process for the treatment of synthetic organic textile fibres which includes the treatment with a composition comprising either a) a mixture of an aminosiloxane and a polyepoxide, b) a mixture of a liquid epoxysiloxane and a polyamine or c) a mixture of a liquid epoxysiloxane and an aminosiloxane.
  • a composition comprising either a) a mixture of an aminosiloxane and a polyepoxide, b) a mixture of a liquid epoxysiloxane and a polyamine or c) a mixture of a liquid epoxysiloxane and an aminosiloxane.
  • these materials tend to give a certain amount of yellowing of the treated fibres.
  • an improved treating composition can be made by restricting the amine-containing organosiloxane to those which are prereacted with a monoepoxide.
  • a method of treating fibrous materials which comprises the application to fibrous materials of a composition comprising as sole amine-containing organosilicon compound the reaction product of a organopolysiloxane having at least one unit of the general formula 03-aSiX a R-NH-2 R' and at least one unit having the general formula 04-bSi-X b with one or more monoepoxides, wherein X de- notes a monovalent hydrocarbon having up to 8 carbon atoms, R denotes a divalent alkylene group, R'denotes a hydrogen atom or a group of the formula R-Z, wherein Z is NHX, NH 2 , NHRNH 2 or NHRNHX, a has a value of 1 or 2 and b has a value of 2 or 3.
  • the organopolysiloxane used in the preparation of the reaction product may be any siloxane polymer having at least 1 unit of the general formula and at least one unit having the general formula .
  • it is a substantially linear polydiorganosiloxane polymer, although small amounts of units 2 which cause branching of the siloxane are possible.
  • Such units which should not be present in more than 5% of the total number of units, have the general structure O3SiX.
  • the substituent X may be any hydrocarbon group having up to 8 carbon atoms, for example alkyl, aryl, alkenyl, alkylaryl and arylalkyl.
  • X denotes a lower alkyl group.
  • X groups are methyl groups. It is, however, possible that small amounts of other substituents are present on silicon atoms, for example hydroxyl or alkoxy groups.
  • the group R is a divalent alkylene group, preferably having up to 8 carbon atoms, most preferably from 3 to 8 carbon atoms. Examples of the R group include dimethylene, propylene, isobutylene and hexylene.
  • the groups R' may be hydrogen or a group of the formula RZ, wherein Z denotes a primary or secondary amine group or a diamine of the formula NHRNH 2 or NHRNHX.
  • a has a value of 1 or 2, which means that the unit may be located in the siloxane chain or may be an end-unit of the siloxane chain.
  • the amine-containing substituent are OSi(CH 3 )(CH 2 ) 3 NH 2 , OSi(CH 3 )CH 2 CH(CH 3 )CH 2 NH 2 , OSi(CH 3 )CH 2 CH(CH 3 )CH 2 NH(CH 2 ) 2 NH 2 , O 1 ⁇ 2 Si(CH 3 ) 2 CH 2 CH(CH 3 )CH 2 NH(CH 2 CH 3 ), O 1 ⁇ 2 Si(CH 3 ) 2 (CH 2 ) 3 NH(CH 2 ) 3 NH(CH 2 ) 3 NH 2 .
  • the other units of the organopolysiloxane are units of the general formula wherein b has a value of 2 or 3 and X has the meaning as above. This means that the units may be present in the siloxane chain or as endgroups of the chain. It is preferred that polydiorganosiloxane having from to 10 to 1000 siloxane units, particularly from 100 to 500 units, most preferably about 400 units are used.
  • the viscosity of the polydiorganosiloxane tends to determine the softness which is imparted to the treated materials, the higher the viscosity, the softer the finish. However, for reasons of practicality it is preferred to use those materials which are liquid at room temperature.
  • Suitable organopolysiloxanes for the preparation of the reaction product for use in the method of the invention are known in the art and many are commercially available. They can be made by methods known in the art, for example by the condensation of aminofunctional silanes or hydrolysis products thereof with cyclic siloxanes in the presence of endblocking units, for example those provided by hexamethyldisiloxanes.
  • Monoepoxides employed in the preparation of the reaction product are organic compounds having one epoxy group.
  • epoxy is meant a group composed of oxirane oxygen attached to two vicinal carbon atoms.
  • Monoepoxides which are suitable for use in the present invention are those wherein the substituent of the said vicinal carbon atoms are hydrogen, hydrocarbon groups or ether or ester containing hydrocarbon groups.
  • one of the carbon atoms has only hydrogen atoms while the other carbon atom has an alkyl group attached to it, which may range from methyl to a linear C 21 alkyl group.
  • Most preferred are those monoepoxides wherein the alkyl group has from 1 to 10 carbon atoms, especially from 1 to 4 carbon atoms.
  • Suitable monoepoxides are ethylene oxide, propylene oxide, butadiene monoxide, 2,3-epoxy-cyclopentane, substituted olefin oxides, e.g. 2, 3-epoxy-propylbenzene, epoxy alcohols, e.g. glycidol, 2,3-epoxy- cyclopentanol, 3,4-epoxy-6-methylcyclohexylmethane, glycidyl ethers, e.g. phenyl glycidyl ether, butyl glycidyl ether or glycidyl esters, e.g.glycidyl acetate.
  • Preferred are those monoepoxides of the general formula wherein n has a value of from 0 to 20, preferably 0 to 8, most preferably 0 to 3.
  • the reaction product for use in the method of the invention may be prepared according to known methods.
  • the two reagents may be reacted together in the presence of a low molecular weight aliphatic alcohol or in the presence of a catalytic amount of water.
  • the reaction can be carried out at room temperature in the presence of such catalyst but is preferably carried out at increased temperatures, for example temperatures of 50°C or more.
  • a solvent which may be the alcohol mentioned above or other suitable solvents.
  • the amount of monoepoxide used in the reaction should be such that no more than 10% of all amine groups in the organopolysiloxane are retained unreacted in the reaction product.
  • two monoepoxide molecules can react with the amine. It is preferred that the majority of the amino groups in the reaction product are tertiary amine groups, although the presence of secondary amine groups to the exclusion of tertiary amine groups is also acceptable.
  • the amine groups in the reaction product may thus be tertiary, secondary, a mixture of these, or a mixture of either or both with up to a maximum of 10% primary amine groups.
  • reaction product is used in the method of the invention, and not a mere mixture of the polydiorganosiloxane and the monoepoxide.
  • Mere mixtures which contain polydiorganosiloxanes having relatively high amounts of primary amine groups are not satisfactory, since they will still display a yellowing of the treated materials. Even a mixture of the two components in the presence of water, e.g. by using an emulsion, is unsatisfactory as the yellowing upon treatment with such mixtures or emulsions is worse than treatment according to the invention.
  • no primary amines are retained in the reaction product. Most preferably no secondary amines are present either in the reaction product.
  • the method of the invention comprises the application to fibrous materials of a composition comprising as sole amine-containing compound the reaction product as described above.
  • This application may be done in any convenient way.
  • Application methods which are suitable include padding, dipping and spraying of a composition comprising the reaction product.
  • the compositions used may be in any suitable form, e.g. solutions, dispersions or emulsions.
  • the dispersions may be in aqueous or solvent based materials while the emulsions are preferably oil-in-water type emulsions.
  • emulsions particularly microemulsions according to European patent specification 138192.
  • Compositions which are useful in the method of the invention may comprise other ingredients which are useful in treatment compositions forfibrous materials, e.g. fatty acid softeners. Other ingredients e.g. surfactants in the emulsions are also useful. It is, however, preferred that the composition comprises no amine-containing compounds other than the reaction product.
  • the method of the invention is suitable for the treatment of both naturally occurring and synthetic fibres, for example carbon fibres, polyester fibres, cotton fibres and blends of cotton and polyester fibres.
  • the application may be done at the stage of making the fibres, at the stage of producing the fabrics or in a special treating step later, for example during laundering of a textile fabric.
  • Application may be followed by drying at room temperature or at increased temperatures. After the drying stage a further heat treatment of the fibrous materials is preferred.
  • the latter is particularly useful when the textile fabrics are treated at the time of their production.
  • the presence of small amounts of primary amine groups on the reaction product will increase the durability of the finish on the fibrous materials, especially when they are subjected to laundering operations.
  • Fibrous materials and textiles which are treated according to the method of the invention have an improved softener and lubricity, a pleasant feel and handle, without suffering from yellowing due to the treatment.
  • a fibrous material treated according to the method of the invention. Also included are fabrics or textiles incorporating fibres when treated according to the method of the invention.
  • reaction product which is believed to have the average formula wherein R' denotes
  • a bath was prepared with a 2.77% solution in perchloro ethylene of the reaction product prepared in Examples 1 to 5 in which a piece of polyester cotton (65/35) was treated by padding. The piece was heated to 110°C for 1 minute, followed by 2 minutes at 180°C after treatment. The piece had picked up 0.5% by weight of the reaction product.
  • reaction product which is believed to have the average formula wherein R' denotes
  • a bath was prepared with a 2.77% solution in perchloro ethylene of the reaction product prepared in Examples 6 to 10, in which a piece of polyester cotton (65/35) was treated by padding. The piece was heated to 110°C for 1 minute, followed by 2 minutes at 180°C after treatment. The piece had picked up 0.5% by weight of the reaction product.
  • reaction product which is believed to have the average formula wherein R' denotes
  • a bath was prepared with a 2.77% solution in perchloro ethylene of the reaction product prepared in Examples 11 to 15, in which a piece of polyester cotton (65/35) was treated by padding. The piece was heated to 110°C for 1 minute, followed by 2 minutes at 180°C after treatment. The piece had picked up 0.5% by weight of the reaction product.
  • reaction product which is believed to have the average formula wherein R' denotes
  • a bath was prepared with a 2.77% solution in perchloro ethylene of the reaction product prepared in Examples 16 to 20, in which a piece of polyester cotton (65/35) was treated by padding. The piece was heated to 110°C for 1 minute, followed by heating at 180°C for minutes aftertreatment. The piece had picked up 0.5% byweight of the reaction product.
  • a bath was prepared with a 2.77% solution in perchloro ethylene of the amino containing polydiorganosiloxane used in Examples 11 to 15 on its own, in which a piece of polyester cotton (65/35) was treated by padding. The piece picked up 0.5% by weight of the siloxane. (Comparative Example 1).
  • Comparative Example 2 As in Comparative Example 1, but using a mixture of 1 molar part of the polydiorganosiloxane of Comparative Example 1 with 2 molar parts of propylene oxide, but not reacted. (Comparative Example 2).
  • Comparative Example 3 was a piece of untreated polyester cotton (blank) as used in Examples 11 to 15.
  • a bath was prepared with a 2.77% solution in perchloro ethylene of the amino containing polydiorganosiloxane used in Examples 16 to 20 on its own, in which a piece of polyester cotton (65/35) was treated by padding. The piece picked up 0.5% by weight of the siloxane. (Comparative Example 4).
  • Comparative Example 5 was a piece of untreated polyester cotton (blank) as used in Examples 16 to 20.
  • Comparative Example 6 was a microemulsion of a mixture of the two reactants of Example 21, in the same proportions and with the same concentration, in which a piece of polyester cotton (65/35) was treated by padding. The piece picked up 1% by weight of the siloxane.
  • Comparative Example 7 was a microemulsion of the amino containing polydiorganosiloxane of Example 21 on its own in the same concentration, in which a piece of polyester cotton (65/35) was treated by padding. The piece picked up 1% by weight of the siloxane.
  • Comparative Example 8 was a piece of untreated polyester cotton (blank) as used in Example 21.
  • Comparative Example 9 was a piece of untreated polyester cotton (blank) as used in Examples 22 and 23.
  • Comparative Example 10 was a microemulsion of the amino containing polydiorganosiloxane of Example 22 on its own in the same concentration, in which a piece of polyester cotton (65/35) was treated by padding. The piece picked up 0.5% by weight of the siloxane.
  • Example 11 The whiteness index of Example 11 was measured using a Hunterlab Optical sensor, Model D25M and compared with Comparative Examples 1, 2 and 3. The following results were obtained:
  • Example 21 The whiteness index of Example 21 was measured using a Hunterlab Optical sensor, Model D25M and compared with Comparative Examples 6, 7 and 8. The following results were obtained:
  • the method according to the invention yields treated materials which have very little yellowing in comparison with materials treated according to the prior art, and have a whiteness index which is very close to that of the untreated material.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Silicon Polymers (AREA)
  • Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)

Claims (10)

1. Un procédé de traitement de matières fibreuses qui comprend l'application aux matières fibreuses d'une composition comprenant un composé organosilicié aminé, caractérisé en ce que le seul composé organosilicié aminé contenu dans la composition est le produit réactionnel d'un organopolysiloxane ayant au moins un motif de la formule générale
Figure imgb0038
et au moins un motif de la formule générale
Figure imgb0039
 avec un ou plusieurs monoépoxydes, où X représente un groupe hydrocarboné monovalent ayant jusqu'à 8 atomes de carbone, R représente un groupe alkylène divalent, R' représente un atome d'hydrogène ou un groupe de la formule RZ où Z est NHX, NH2, NHRNH2 ou NHRNHX, la valeur de a est 1 ou 2 et la valeur de b est 2 ou 3.
2. Un procédé selon la revendication 1, caractérisé en ce que l'organopolysiloxane est un polydiorganosiloxane sensiblement linéaire dans lequel au moins 80 % de tous les groupes X sont des groupes méthyle.
3. Un procédé selon la revendication 1 ou la revendication 2, caractérisé en ce que l'organopolysiloxane comprend 100 à 500 motifs siloxanes.
4. Un procédé selon l'une quelconque des revendications précédentes, caractérisé en ce que 1 à 10 mol % de tous les motifs siloxanes de l'organopolysiloxane sont des motifs de la formule 03-aSiXaRNHR'. 2
5. Un procédé selon l'une quelconque des revendications précédentes, caractérisé en ce que le monoépoxy- de répond à la formule générale
Figure imgb0040
où la valeur de n est de 0 à 8.
6. Un procédé selon l'une quelconque des revendications précédentes, caractérisé en ce que la majorité des groupes amino présents dans le produit réactionnel sont des groupes amino tertiaires, le produit réactionnel ne contenant pas plus de 10 % de groupes amino primaires.
7. Un procédé selon l'une quelconque des revendications précédentes, caractérisé en ce que le produit réactionnel ne contient aucun groupe amino primaire ou secondaire.
8. Un procédé selon l'une quelconque des revendications précédentes, caractérisé en ce que la composition est sous la forme d'une émulsion.
9. Un procédé selon l'une quelconque des revendications précédentes, caractérisé en ce que la composition ne comprend pas d'autres composés aminés que le produit réactionnel.
10. Textiles comprenant des fibres, caractérisés en ce que les fibres ont été traitées par un procédé selon l'une quelconque des revendications précédentes.
EP19900305117 1989-05-24 1990-05-11 Procédé de traitement de matériaux fibreux Expired - Lifetime EP0399706B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB898911970A GB8911970D0 (en) 1989-05-24 1989-05-24 Method of treating fibrous materials
GB8911970 1989-05-24

Publications (3)

Publication Number Publication Date
EP0399706A2 EP0399706A2 (fr) 1990-11-28
EP0399706A3 EP0399706A3 (fr) 1991-03-20
EP0399706B1 true EP0399706B1 (fr) 1993-09-01

Family

ID=10657290

Family Applications (1)

Application Number Title Priority Date Filing Date
EP19900305117 Expired - Lifetime EP0399706B1 (fr) 1989-05-24 1990-05-11 Procédé de traitement de matériaux fibreux

Country Status (6)

Country Link
EP (1) EP0399706B1 (fr)
JP (1) JP2846058B2 (fr)
CA (1) CA2016833A1 (fr)
DE (1) DE69003009T2 (fr)
ES (1) ES2043277T3 (fr)
GB (1) GB8911970D0 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8796198B2 (en) 2011-08-12 2014-08-05 Evonik Degussa Gmbh Process for producing polysiloxanes with nitrogen-containing groups

Families Citing this family (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB9004627D0 (en) * 1990-03-01 1990-04-25 Dow Corning Composition for treating carbon fibre precursors and precursors treated therewith
DE4117864A1 (de) * 1991-05-31 1992-12-03 Pfersee Chem Fab Waessrige dispersionen von polysiloxanen
DE4211256A1 (de) * 1992-04-03 1993-10-07 Wacker Chemie Gmbh Vernetzbare Zusammensetzung auf Aminosiliconbasis
EP0577039B1 (fr) * 1992-06-29 1999-09-08 Witco Corporation Procedé pour le traitement d' un textile avec un aminopolysiloxane et textile traité
JP2590234Y2 (ja) * 1993-11-16 1999-02-10 マリンブルーブロー株式会社 花壇等に立設する中空状の柵体
DE4424914A1 (de) 1994-07-14 1996-01-18 Wacker Chemie Gmbh Aminofunktionelle Organopolysiloxane
US6136215A (en) * 1999-09-02 2000-10-24 Dow Corning Corporation Fiber treatment composition containing amine-, polyol-, amide-functional siloxanes
US6255429B1 (en) * 1999-09-02 2001-07-03 Dow Corning Corporation Amine-, polyol-, amide-functional siloxane copolymers and methods for their preparation
US6171515B1 (en) 1999-09-02 2001-01-09 Dow Corning Corporation Fiber treatment composition containing amine-, polyol-, functional siloxanes
GB0202631D0 (en) * 2002-02-05 2002-03-20 Dow Corning Hair care compositions containing polysiloxanes
JP4147067B2 (ja) * 2002-08-09 2008-09-10 花王株式会社 洗浄剤組成物
US20040053810A1 (en) * 2002-08-16 2004-03-18 Tully Jo Anne Liquid laundry compositions comprising silicone additives
US7790801B2 (en) 2007-07-24 2010-09-07 Momentive Performance Materials Inc. Organo-functional silicone in emulsion systems and process for preparing same
US20110243874A1 (en) * 2010-04-01 2011-10-06 Rajan Keshav Panandiker Care polymers
DE102010062156A1 (de) 2010-10-25 2012-04-26 Evonik Goldschmidt Gmbh Polysiloxane mit stickstoffhaltigen Gruppen
DE102010062676A1 (de) 2010-12-09 2012-06-14 Evonik Goldschmidt Gmbh Zubereitungen enthaltend Polysiloxane mit stickstoffhaltigen Gruppen
US9346023B2 (en) 2012-08-21 2016-05-24 General Electric Company Flux enhancing agent for improving composite polyamide reverse osmosis membrane performance
US9499671B2 (en) 2014-10-15 2016-11-22 Ramani Narayan Hydrophilic polysiloxane compositions containing carbinol groups
KR101640714B1 (ko) * 2015-06-11 2016-07-18 치 솅 엔터프라이즈 컴퍼니 엘티디. 스키화 바인딩

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1547884A (en) * 1975-08-20 1979-06-27 Nuova San Giorgio Spa Apparatus for reinserting broken yarn in an open end spinning unit
JPS6039792A (ja) * 1983-08-12 1985-03-01 松下電工株式会社 調光装置
JPS6110498A (ja) * 1984-06-25 1986-01-17 大日本塗料株式会社 浮彫模様の形成方法
JPS6375184A (ja) * 1986-09-19 1988-04-05 信越化学工業株式会社 合成繊維用処理剤
JPS6445466A (en) * 1987-08-14 1989-02-17 Shinetsu Chemical Co Textile treating composition

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8796198B2 (en) 2011-08-12 2014-08-05 Evonik Degussa Gmbh Process for producing polysiloxanes with nitrogen-containing groups

Also Published As

Publication number Publication date
CA2016833A1 (fr) 1990-11-24
GB8911970D0 (en) 1989-07-12
DE69003009T2 (de) 1994-01-13
DE69003009D1 (de) 1993-10-07
JP2846058B2 (ja) 1999-01-13
EP0399706A2 (fr) 1990-11-28
JPH0351375A (ja) 1991-03-05
EP0399706A3 (fr) 1991-03-20
ES2043277T3 (es) 1993-12-16

Similar Documents

Publication Publication Date Title
EP0399706B1 (fr) Procédé de traitement de matériaux fibreux
EP0441530B1 (fr) Procédé de traitement de matières fibreuses
EP3445822B1 (fr) Amino-organopolysiloxane et procédé pour sa préparation
US4283519A (en) Organosilicone terpolymers
US5540952A (en) Non-yellowing textile softening process in which a composition comprising a polyorganosiloxane is used
US4757121A (en) Silicone-based softening agent for synthetic fibers
CA1159073A (fr) Copyolymeres de silicone et de polyether
EP0342830B1 (fr) Composés organosiliciques
KR100517103B1 (ko) 질소 원자 함유 폴리실록산, 그의 제조 방법 및 섬유처리제 조성물
US4725635A (en) Silicone-based synthetic fiber finishing agent
JPH0798904B2 (ja) 新規アミノ官能性ポリシロキサンのエマルジョン組成物
JPS6310743B2 (fr)
JPH0366429B2 (fr)
US4625010A (en) Organopolysiloxanes having Si-bonded hydrogen and SiC-bonded epoxy groups and a process for preparing the same
US5824814A (en) Process for stabilising siloxane polymers
EP0523910B1 (fr) Composés organosiliciques
US4666745A (en) Organopolysiloxanes having Si-bonded hydrogen and SiC-bonded epoxy groups and a process for preparing the same
CA2449955A1 (fr) Polysiloxane et adjuvant textile contenant un polysiloxane
KR101003798B1 (ko) 친수성 아미노변성 폴리실록산 및 이의 제조방법
JPS584114B2 (ja) 羊毛を防縮加工するための調製剤
US6384254B1 (en) Quaternary ammonium salt-containing polysiloxane, making method, and fiber or fabric treating agent composition
JPS6129612B2 (fr)
KR100271593B1 (ko) 섬유 처리제
EP0044540B1 (fr) Compositions d'organopolysiloxanes pour le traitement de matières textiles; leur préparation, un procédé pour le traitement de matières textiles et matières textiles ainsi traitées

Legal Events

Date Code Title Description
PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

Free format text: ORIGINAL CODE: 0009012

AK Designated contracting states

Kind code of ref document: A2

Designated state(s): BE DE ES FR GB IT NL

PUAL Search report despatched

Free format text: ORIGINAL CODE: 0009013

17P Request for examination filed

Effective date: 19901221

AK Designated contracting states

Kind code of ref document: A3

Designated state(s): BE DE ES FR GB IT NL

17Q First examination report despatched

Effective date: 19930203

GRAA (expected) grant

Free format text: ORIGINAL CODE: 0009210

AK Designated contracting states

Kind code of ref document: B1

Designated state(s): BE DE ES FR GB IT NL

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: NL

Effective date: 19930901

Ref country code: BE

Effective date: 19930901

ITF It: translation for a ep patent filed

Owner name: JACOBACCI CASETTA & PERANI S.P.A.

REF Corresponds to:

Ref document number: 69003009

Country of ref document: DE

Date of ref document: 19931007

REG Reference to a national code

Ref country code: ES

Ref legal event code: FG2A

Ref document number: 2043277

Country of ref document: ES

Kind code of ref document: T3

ET Fr: translation filed
NLV1 Nl: lapsed or annulled due to failure to fulfill the requirements of art. 29p and 29m of the patents act
PLBE No opposition filed within time limit

Free format text: ORIGINAL CODE: 0009261

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: NO OPPOSITION FILED WITHIN TIME LIMIT

26N No opposition filed
PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: GB

Payment date: 20000327

Year of fee payment: 11

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: FR

Payment date: 20000330

Year of fee payment: 11

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: ES

Payment date: 20000510

Year of fee payment: 11

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: DE

Payment date: 20000529

Year of fee payment: 11

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: GB

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20010511

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: ES

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20010512

GBPC Gb: european patent ceased through non-payment of renewal fee

Effective date: 20010511

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: FR

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20020131

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: DE

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20020301

REG Reference to a national code

Ref country code: ES

Ref legal event code: FD2A

Effective date: 20030203

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: IT

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES;WARNING: LAPSES OF ITALIAN PATENTS WITH EFFECTIVE DATE BEFORE 2007 MAY HAVE OCCURRED AT ANY TIME BEFORE 2007. THE CORRECT EFFECTIVE DATE MAY BE DIFFERENT FROM THE ONE RECORDED.

Effective date: 20050511