EP0308914A2 - Esters de l'acide alkénylsuccinique contenant des groupes aminés - Google Patents
Esters de l'acide alkénylsuccinique contenant des groupes aminés Download PDFInfo
- Publication number
- EP0308914A2 EP0308914A2 EP88115534A EP88115534A EP0308914A2 EP 0308914 A2 EP0308914 A2 EP 0308914A2 EP 88115534 A EP88115534 A EP 88115534A EP 88115534 A EP88115534 A EP 88115534A EP 0308914 A2 EP0308914 A2 EP 0308914A2
- Authority
- EP
- European Patent Office
- Prior art keywords
- alkyl
- alkenyl
- weight
- parts
- amino groups
- 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.)
- Granted
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
- 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
- D06M13/402—Amides imides, sulfamic acids
-
- 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
- D06M7/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made of other substances with subsequent freeing of the treated goods from the treating medium, e.g. swelling, e.g. polyolefins
-
- 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
- D06M2200/40—Reduced friction resistance, lubricant properties; Sizing compositions
Definitions
- preparation agents When manufacturing synthetic fibers, it is absolutely necessary to apply so-called preparation agents to the fiber surface.
- the main task of these preparation agents is to avoid thread-metal friction, but also to adjust thread-thread friction and to prevent electrostatic charging.
- texturing polyester threads for example, the threads are passed through a spindle at high speed and then over heating sections to fix the bulk. Due to the high temperatures (above 200 ° C), the preparation agents are thermally decomposed or sublime, sit on the heating units and crack to solid black residues, which disturb the further texturing process. Therefore, the systems have to be shut down at regular intervals and the heating units have to be cleaned mechanically from the residues, which causes costs and can also be detrimental to the health of the workers responsible for cleaning. Therefore, there is great interest in thermostable lubricants that only form liquid residues on the heating units that are emulsifiable with water and can therefore be easily removed.
- alkenylsuccinic acid esters containing amino groups described below are suitable as fiber preparation agents and are distinguished by improved thermal stability.
- the invention thus relates to alkenylsuccinic acid esters of the formulas containing amino groups wherein R is linear or branched C1-C20-, preferably C5-C15-alkyl, R1 hydroxy-C2-C6-alkyl or C1-C4-alkyl, R2 methyl or ethyl, R3 C6-C20-, preferably C12-C18-alkyl or C6-C20-, preferably C12-C18 alkenyl, A -C2H4- or -C3H7- and n represent a number from 1 to 10, preferably from 3 to 8.
- alkenyl succinic acids of the formula or preferably their anhydrides first with about one mole of an amine of the formula implemented and the thereby obtained Alkenyl succinic acid semiesters with about one mole of an oxyalkylated alcohol of the formula R3 (OA) n -OH implements.
- the alkenylsuccinic anhydrides are obtained by reacting ⁇ -olefins with maleic anhydride at temperatures around 200 ° C.
- Linear or branched olefins such as tripropylene (i-non) or tetrapropylene (i-dodecene) can be used for this reaction.
- the oxyalkylated fatty alcohols are prepared by known processes by adding ethylene oxide or propylene oxide to the underlying alcohols.
- the reaction of the alkenylsuccinic anhydrides with the aliphatic amino compounds takes place at temperatures from 20 to 120 ° C., preferably at 60 to 100 ° C.
- the 2nd stage i.e. the esterification of the free carboxy group with the fatty alcohol oxyethylate is carried out at temperatures of 140 to 260 ° C, preferably at temperatures of 160 to 200 ° C with acid catalysis.
- the acids used for this can be inorganic compounds such as sulfuric acid, phosphoric acid, phosphorous acid etc. or organic acids such as p-toluenesulfonic acid or acidic ion exchangers.
- the amounts required for this depend on the type of acid, they are between 0.1 to 3% by weight, preferably 0.5 to 1.5% by weight.
- the water of reaction is separated off by distillation until an acid number below 10 is reached.
- the two stages of the reaction can be carried out both in the presence and in the absence of a solvent.
- Inert organic solvents with a high boiling point such as decalin or chlorinated aromatic hydrocarbons, are suitable as solvents.
- the alkenyl succinic acid esters according to the invention are used as preparation components for the preparation of fibers made of polyester, polyamide, polyacrylonitrile, polyolefins and Aramid fibers.
- lubricants such as mineral oils or ester oils, for example hexadecyl stearate
- they can be used, inter alia, in combination with emulsifiers based on ethoxylated fatty alcohols or in conjunction with antistatic agents, thread-locking agents.
- Their proportion in the filament preparations can range from 90 to 10%, preferably 60 to 30%.
- the requirements for preparation on the fiber generally range from 0.1 to 2%, preferably 0.3 to 1.2% by weight.
- alkenylsuccinic acid esters have the advantage that they are thermostable and that the residues of these compounds are liquid under the conditions under which they are used in textile fiber production and can therefore be easily removed.
- Example 2 The procedure is as described in Example 1, except that 50 g of i-nonenylsuccinic anhydride are used instead of n-dodecenylsuccinic anhydride. About 45 g of a light brown liquid with a pH of 7 are obtained.
- n-octadecenylsuccinic anhydride 70 parts by weight of n-octadecenylsuccinic anhydride are dissolved in 150 parts by volume of tetralin in a 500 ml vessel with stirrer, internal thermometer and short-path distillation attachment, and 21.6 parts by weight of N, N-diethylethanolamine are added dropwise at 35 ° C. in the course of 30 minutes with stirring and nitrogen sparge. The mixture is left to react within 4 hours at 50 ° C., cooled to room temperature and mixed with 107 parts by weight of stearyl alcohol 6 moles of ethylene oxide and 3 parts by weight of p-toluenesulfonic acid.
- Example 2 The procedure is as described in Example 2, except that 25 parts by weight of N, N-dimethylbutanolamine are used instead of 21.6 parts by weight of N, N-diethylethanolamine. About 193 parts by weight of a light brown, viscous oil with a pH of 7 are obtained.
Landscapes
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
- Liquid Crystal Substances (AREA)
- Lubricants (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE3732340 | 1987-09-25 | ||
DE19873732340 DE3732340A1 (de) | 1987-09-25 | 1987-09-25 | Aminogruppen enthaltende alkenylbernsteinsaeureester |
Publications (3)
Publication Number | Publication Date |
---|---|
EP0308914A2 true EP0308914A2 (fr) | 1989-03-29 |
EP0308914A3 EP0308914A3 (en) | 1989-11-23 |
EP0308914B1 EP0308914B1 (fr) | 1993-06-30 |
Family
ID=6336870
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP88115534A Expired - Lifetime EP0308914B1 (fr) | 1987-09-25 | 1988-09-22 | Esters de l'acide alkénylsuccinique contenant des groupes aminés |
Country Status (4)
Country | Link |
---|---|
US (1) | US4883495A (fr) |
EP (1) | EP0308914B1 (fr) |
JP (1) | JPH0196157A (fr) |
DE (2) | DE3732340A1 (fr) |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5032145A (en) * | 1987-04-20 | 1991-07-16 | Mobil Oil Corporation | Low temperature fluidity improver and compositions thereof |
JPH0412161A (ja) * | 1990-05-01 | 1992-01-16 | Mazda Motor Corp | エンジンの吸気装置 |
US5427589A (en) * | 1993-03-03 | 1995-06-27 | Springs Industries, Inc. | Method for dyeing fibrous materials |
US5437690A (en) * | 1994-05-25 | 1995-08-01 | Springs Industries, Inc. | Method for dyeing fibrous materials and dye assistant relating to the same |
EP1559500B1 (fr) | 2004-01-29 | 2011-08-17 | Siemens Aktiengesellschaft | Procédé et dispositif d'usinage mécanique d'un composant creux |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3497550A (en) * | 1966-11-07 | 1970-02-24 | Kendall & Co | Polymerizable monomers,copolymers thereof and adhesive made therefrom |
DD160287A1 (de) * | 1981-04-30 | 1983-05-25 | Juergen Peschel | Verschleissmindernd wirkende praeparation fuer schnellgesponnene pigmentierte polyesterendlosfaeden |
EP0149549A2 (fr) * | 1984-01-16 | 1985-07-24 | The Lubrizol Corporation | Sels de cuivre de dérivés d'anhydride succinique |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4185485A (en) * | 1978-06-30 | 1980-01-29 | Mobil Oil Corporation | Lubricant compositions for can forming |
US4435297A (en) * | 1978-09-27 | 1984-03-06 | The Lubrizol Corporation | Carboxylic acid derivatives of alkanol tertiary monoamines |
DE3526601A1 (de) * | 1985-07-25 | 1987-01-29 | Hoechst Ag | Oxalkylierte polyesteramine, verfahren zu deren herstellung und deren verwendung |
-
1987
- 1987-09-25 DE DE19873732340 patent/DE3732340A1/de not_active Withdrawn
-
1988
- 1988-09-21 US US07/247,277 patent/US4883495A/en not_active Expired - Fee Related
- 1988-09-22 EP EP88115534A patent/EP0308914B1/fr not_active Expired - Lifetime
- 1988-09-22 DE DE8888115534T patent/DE3882106D1/de not_active Expired - Fee Related
- 1988-09-22 JP JP63236664A patent/JPH0196157A/ja active Pending
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3497550A (en) * | 1966-11-07 | 1970-02-24 | Kendall & Co | Polymerizable monomers,copolymers thereof and adhesive made therefrom |
DD160287A1 (de) * | 1981-04-30 | 1983-05-25 | Juergen Peschel | Verschleissmindernd wirkende praeparation fuer schnellgesponnene pigmentierte polyesterendlosfaeden |
EP0149549A2 (fr) * | 1984-01-16 | 1985-07-24 | The Lubrizol Corporation | Sels de cuivre de dérivés d'anhydride succinique |
Also Published As
Publication number | Publication date |
---|---|
DE3732340A1 (de) | 1989-04-13 |
JPH0196157A (ja) | 1989-04-14 |
EP0308914A3 (en) | 1989-11-23 |
EP0308914B1 (fr) | 1993-06-30 |
US4883495A (en) | 1989-11-28 |
DE3882106D1 (de) | 1993-08-05 |
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