Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C233/00—Carboxylic acid amides
  • C07C233/64—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings
  • C07C233/67—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
  • C07C233/68—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
  • C07C233/69—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom of an acyclic saturated carbon skeleton
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
  • C07C215/02—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
  • C07C215/04—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated
  • C07C215/06—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated and acyclic
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
  • C09D167/00—Coating compositions based on polyesters obtained by reactions forming a carboxylic ester link in the main chain; Coating compositions based on derivatives of such polymers

Definitions

• This invention relates to novel ⁇ -hydroxyalkylamides, a method for their production and their use.
• ⁇ -hydroxyalkylamides are very important as intermediate products and as cross linkers for polymers.
• ⁇ -hydroxyalkylamides are conventionally produced by the aminolysis of alkyl esters with ⁇ -alkanol amines in the presence of basic catalysts.
• the a hydroxyalkylamides are isolated and purified either by crystallization in a solvent or, especially with solid ⁇ -hydroxyalkylamides, without the use of solvent in a slurry process.
• a process of the above referenced type is described in U.S. Pat. No. 5,101,073 and in EP 0 473 380 B1.
• the slurry process is based on the fact that the equilibrium reaction that occurs during the production of the ⁇ -hydroxyalkylamides is shifted toward the desired end product as a result of the fact that the desired ⁇ -hydroxyalkylamide is precipitated from the melt by tempering in a defined temperature range and the melt is then crystallized.
• a disadvantage of this method is the use of equimolar quantities of alkyl ester and ⁇ -hydroxyalkylamide.
• EP-A-322 834 describes a powder coating which contains a polyester and ⁇ -hydroxyalkylkamides as cross linkers (curing agents). Corresponding coatings with good characteristics can be produced with the formulation described in said document.
• the object of this invention is to propose new, previously unknown ⁇ -hydroxyalkylamides and a corresponding process for their production.
• the invention teaches that this object can be accomplished with regard to the ⁇ -hydroxyalkylamides by the characterizing features of claim 1 , and with regard to the process for their manufacture by the characterizing features of claim 4 .
• the subclaims describe advantageous developments of the invention.
• the use of the ⁇ -hydroxyalkylamides claimed by the invention is described in the characterizing portions of claims 11 to 14 .
• R 1 stands for hydrogen or a linear or branched C 1 to C 10 alkyl.
• R 2 is a linear or branched C 1 to C 5 alkyl.
• the ⁇ -hydroxyalkylamides claimed by the invention are characterized in particular by the substituted carbon atom next to the OH group. In the ⁇ -hydroxyalkylamides claimed by the invention, the R 2 group is located here.
• the ⁇ -hydroxyalkylamide is preferably constructed so that the RI group is H, tert-butyl, isopropyl or pentyl and is located in the para position to the CO group.
• R 1 group is hydrogen and the R 2 group is methyl.
• R 1 and R 2 groups thereby have the definitions presented above.
• the R 3 group can thereby be a halogen, preferably chlorine, or an OR 4 group. If there is an OR 4 group, R 4 is a linear C 1 to C 5 alkyl, preferably a —CH 3 group.
• the conversion of the carboxylic acid derivative and the alkanol amine preferably takes place in a solution.
• Preferred solvents include but are not restricted to: aromatic hydrocarbons such as benzene, toluene or xylene. Ethers such as diethylether or mixtures of the solvents listed above are also suitable.
• An essential feature of the process claimed by the invention is that the carboxylic acid derivative having the general Formula II and the alkanol amine having the general Formula III are reacted with vigorous agitation of stirring.
• the alkanol amine is thereby preferably presented first and the carboxylic acid derivative is then added by drops with vigorous agitation of stirring.
• the conversion takes place at ⁇ 10 to 25° C., preferably at 0 to 10° C.
• the reaction time is normally 0.5 to 5 hours. A reaction time of 2 hours is most advantageous.
• the reaction temperature at RT is up to 150° C.
• the ⁇ -hydroxyalkylamide is particularly well suited as a cross linker for polymers.
• ⁇ -hydroxyalkylamide is particularly preferred as a cross-linker for powder coats with polyesters or acrylates as the polymer.
• the ⁇ -hydroxyalkylamide can be used as a cross linker (curing agent) analogous to the ⁇ -hydroxyalkylamides cited in EP-A-322 A34.
• the ⁇ -hydroxyalkylamides taught by the invention can also be used in combination with other curing agents.
• One example of this usage is the curing agent sold under the name PRIMID® by EMS—CHEMIE AG, Domat/Ems.
• PRIMID® is N,N,N′,N′ 2-hydroxyethyladipamide.

Landscapes

• Chemical & Material Sciences (AREA)
• Organic Chemistry (AREA)
• Chemical Kinetics & Catalysis (AREA)
• Life Sciences & Earth Sciences (AREA)
• Engineering & Computer Science (AREA)
• Materials Engineering (AREA)
• Wood Science & Technology (AREA)
• Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
• Paints Or Removers (AREA)

Priority Applications (1)

Applications Claiming Priority (2)

Related Child Applications (1)

Publications (1)

Family

ID=7661187

Family Applications (2)

Family Applications After (1)

Country Status (17)

Cited By (1)

Families Citing this family (6)

Family Cites Families (9)

• 2000
  • 2000-10-26 DE DE10053194A patent/DE10053194A1/de not_active Ceased
• 2001
  • 2001-07-20 US US09/909,573 patent/US20020055595A1/en not_active Abandoned
  • 2001-09-24 EP EP01122856A patent/EP1203763B1/fr not_active Expired - Lifetime
  • 2001-09-24 ES ES01122856T patent/ES2333643T3/es not_active Expired - Lifetime
  • 2001-09-24 DE DE50115225T patent/DE50115225D1/de not_active Expired - Lifetime
  • 2001-09-24 AT AT01122856T patent/ATE449063T1/de not_active IP Right Cessation
  • 2001-09-26 CZ CZ20013461A patent/CZ302774B6/cs not_active IP Right Cessation
  • 2001-09-26 AU AU76116/01A patent/AU784957B2/en not_active Ceased
  • 2001-09-28 PL PL349933A patent/PL204666B1/pl unknown
  • 2001-10-02 NZ NZ514573A patent/NZ514573A/xx not_active IP Right Cessation
  • 2001-10-05 TW TW90124706A patent/TW574183B/zh not_active IP Right Cessation
  • 2001-10-19 JP JP2001322105A patent/JP2002145839A/ja active Pending
  • 2001-10-22 MX MXPA01010682A patent/MXPA01010682A/es active IP Right Grant
  • 2001-10-23 CA CA2359768A patent/CA2359768C/fr not_active Expired - Lifetime
  • 2001-10-24 BR BR0104738-8A patent/BR0104738A/pt not_active IP Right Cessation
  • 2001-10-24 NO NO20015202A patent/NO328093B1/no not_active IP Right Cessation
  • 2001-10-26 CN CNB011375140A patent/CN1315785C/zh not_active Expired - Fee Related
  • 2001-10-26 KR KR1020010066270A patent/KR100821024B1/ko active IP Right Grant
• 2004
  • 2004-06-12 US US10/866,979 patent/US7030272B2/en not_active Expired - Lifetime

Also Published As

Similar Documents

Legal Events