Immersion oils having long service life

Patent metadata

Field	Value
Publication number	US-2021302712-A1
Application number	US-202117213549-A
Country	US
Kind code	A1
Filing date	Mar 26, 2021
Priority date	Mar 30, 2020
Publication date	Sep 30, 2021
Grant date	—

Abstract

An immersion oil for microscopy contains a) a first diester A1 based on a tricyclodecane radical K having one functional group and a first hydrocarbon derivative C1 having two functional groups, and b) a second diester A2 based on the tricyclodecane radical K having one functional group and a second hydrocarbon derivative C2 having two functional groups, where C1 and C2 are different. Methods can be used for the production of the immersion oil and for the use thereof in microscopy.

First claim

1 . An immersion oil for microscopy, comprising:
a) a first diester A1 based on a tricyclodecane radical K having one functional group and a first hydrocarbon derivative C1 having two functional groups, and b) a second diester A2 based on the tricyclodecane radical K having one functional group and a second hydrocarbon derivative C2 having two functional groups, wherein C1 and C2 are different.

2 . The immersion oil according to claim 1 , wherein the number of carbon atoms in the first hydrocarbon derivative C1 having two functional groups and the number of carbon atoms in the second hydrocarbon derivative C2 having two functional groups differ by at least one carbon atom.

3 . The immersion oil according to claim 1 , wherein the tricyclodecane radical K having one functional group is selected from the group consisting of:

4 . The immersion oil according to claim 1 , wherein the tricyclodecane radical K having one functional group is selected from the group consisting of:

5 . The immersion oil according to claim 1 , comprising:
a) 15-85% by weight of the first diester A1 based on a tricyclodecane radical K having one functional group and a first hydrocarbon derivative C1 having two functional groups, and b) 15-85% by weight of the second diester A2 based on the tricyclodecane radical K having one functional group and a second hydrocarbon derivative C2 having two functional groups.

6 . The immersion oil according to claim 1 ,
wherein the amount of the diesters A1 and A2 satisfies the following conditions: (i) % by mass(A1)=% by mass(A1) E ±5% by mass, (ii) % by mass(A2)=% by mass(A2) E ±5% by mass, wherein the % by mass(A1) E and the % by mass(A2) E correspond to the percentages by mass of A1 and A2 at the eutectic point in a phase diagram of a mixture of A1 and A2.

7 . The immersion oil according to claim 1 , wherein the dispersion value is within a range from 39±2 to 47±2.

8 . The immersion oil according to claim 1 , wherein transmission in the visible region is more than 70% at wavelengths greater than 350 nm.

9 . An immersion oil obtainable by:
(a) reacting in a spatially unseparated one-pot reaction
(i) a tricyclodecane radical K having one functional group and a first hydrocarbon derivative C1 having two functional groups, and
(ii) the tricyclodecane radical K having one functional group and a second hydrocarbon derivative C2 having two functional groups,
wherein C1 and C2 are different,
wherein the reacting produces a reaction product, and
(b) working up, distillative working up, or activated carbon filtering of the reaction product from (a).

10 . A method of microscopy, the method comprising:
increasing the numerical aperture of an objective with the immersion oil according to claim 1 .

11 . A process for producing the immersion oil according to claim 1 , the process comprising:
i) providing a first diester A1 and a second diester A2, as a mixture M, ii) optionally, providing further constituents, and iii) mixing the first diester A1 and the second diester A2 with any further constituents.

12 . The method according to claim 11 ,
wherein the providing of the mixture M comprises the following: iv) preparing a solution of a first hydrocarbon derivative C1 having two functional groups and a second hydrocarbon derivative C2 having two functional groups, in a solvent, v) adding a tricyclodecane radical K having one functional group, thereby producing a reaction mixture, and vi) optionally, heating the reaction mixture and optionally, adding an esterification catalyst, thereby producing an obtained crude product.

13 . The method according to claim 12 , wherein vi) is followed by:
vii) removing the obtained crude product, and viii) optionally, purifying the obtained crude product.

Assignees

• Zeiss Carl Jena Gmbh

Inventors

• Jaeger Jakob Benedikt
• Krieg Matthias
• Weippert Hans-Joachim

Classifications

• G02B21/33 Primary

  Immersion oils {, or microscope systems or objectives for use with immersion fluids} · CPC title

• C07C67/08

  by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds · CPC title

• C07C67/54

  by distillation · CPC title

• C07C2603/10

  containing five-membered rings · CPC title