Hydrocarbon resin, method for preparing hydrocarbon resin, and adhesive composition

Patent metadata

Field	Value
Publication number	US-10988644-B2
Application number	US-201515741099-A
Country	US
Kind code	B2
Filing date	Dec 31, 2015
Priority date	Jun 30, 2015
Publication date	Apr 27, 2021
Grant date	Apr 27, 2021

Abstract

Provided are a hydrocarbon resin and a method of preparing the same, wherein thermal polymerization of a diolefin and an olefin is performed, thus obviating a catalyst removal process, material supply problems can be solved, and a hydrogenated hydrocarbon resin can be prepared using a catalyst, which is inexpensive and is easy to handle, thereby realizing a yield and a preparation process that enable real-world application thereof. The hydrogenated hydrocarbon resin prepared by the method of the invention has excellent compatibility and a low specific viscosity, and can thus be efficiently used as a tackifier or an adhesive in a variety of fields.

First claim

The invention claimed is:

1. A method of preparing a hydrocarbon resin, comprising:
(S1) preparing a polymer through thermal polymerization of a dicyclopentadiene and a C6-C20 olefin mixed together in a solvent; and
(S2) hydrogenating the polymer of S1 using a hydrogenation catalyst,
wherein an amount of the solvent is greater than an amount of dicyclopentadiene,
wherein the olefin in S1 is a linear alpha-olefin (LAO),
wherein the hydrocarbon resin comprises a repeating unit represented by Chemical Formula 1 and a repeating unit represented by Chemical Formula 2,
wherein Formula 1 is

wherein Formula 2 is

wherein R 1 is hydrogen or a methyl group, R 2 is a C 4 -C 18 alkyl group when R 1 is hydrogen, and R 2 is a C 3 -C 17 alkyl group when R 1 is a methyl group, and m and n are each an integer of 0 to 10,
wherein the hydrocarbon resin includes 10 to 40 mol % of an olefin-derived component, and
wherein a ratio of a peak area of 5.9 ppm to 6.0 ppm to a peak area of 5.6 ppm to 5.9 ppm of the polymer in 1 H-NMR spectrum is 0.14 to 0.27.

2. The method of claim 1 , wherein the olefin in S1 is added in an amount of 0.1 to 2.0 mol relative to 1 mol of the dicyclopentadiene.

3. The method of claim 1 , wherein the thermal polymerization in S1 is performed at 200-320° C. for 0.5 to 4 hr.

4. The method of claim 1 , wherein the hydrogenation catalyst in S2 is at least one selected from the group consisting of nickel, palladium, cobalt, platinum and rhodium catalysts.

5. The method of claim 1 , wherein the hydrogenation catalyst in S2 is added in an amount of 0.001 to 0.5 mol relative to 1 mol of the dicyclopentadiene.

6. The method of claim 1 , wherein the hydrogenating in S2 is performed at a pressure of 50 to 150 bar and a temperature of 150 to 300° C.

7. A hydrocarbon resin, comprising a repeating unit represented by Chemical Formula 1 and a repeating unit represented by Chemical Formula 2,
wherein Formula 1 is

wherein Formula 2 is

wherein R 1 is hydrogen or a methyl group, R 2 is a C 4 -C 18 alkyl group when R 1 is hydrogen, and R 2 is a C 3 -C 17 alkyl group when R 1 is a methyl group, and m and n are each an integer of 0 to 10,
wherein the hydrocarbon resin includes 10 to 40 mol % of an olefin-derived component, and
wherein the hydrocarbon resin is prepared by hydrogenating a polymer,
wherein a ratio of a peak area of 5.9 ppm to 6.0 ppm to a peak area of 5.6 ppm to 5.9 ppm of the polymer in 1 H-NMR spectrum is 0.14 to 0.27.

8. The hydrocarbon resin of claim 7 , wherein the hydrocarbon resin has a weight average molecular weight of 500 to 3000 g/mol, a softening point of 10 to 150° C., and a color scale (APHA color) of 1 to 100.

9. The hydrocarbon resin of claim 8 , wherein the hydrocarbon resin has a peak area ratio S1 of 20% or more and a peak area ratio S2 of 50% or more, based on spectrum results after 1 H-NMR measurement, as determined by Equations 1 and 2,
wherein S 1= A 1/ A 3,
wherein S 2= A 2/ A 3, and
wherein A1 is a peak area of 0.8 to 1.0 ppm, A2 is a peak area of 1.0 to 1.4 ppm, and A3 is a peak area of 1.4 to 7.5 ppm, based on the spectrum results after 1 H-NMR measurement of the hydrocarbon resin.

10. An adhesive composition, comprising:
a hydrocarbon resin including a repeating unit represented by Chemical Formula 1 and a repeating unit represented by Chemical Formula 2;
at least one polymer selected from the group consisting of a styrenic block copolymer, polyethylene, polypropylene, ethylene vinyl acetate, and an ethylene-based polyolefin block copolymer; and
at least one oil selected from the group consisting of synthetic wax, animal natural wax, vegetable natural wax, aromatic oil, naphthenic oil, and paraffinic oil,
wherein Formula 1 is

wherein Formula 2 is

and wherein R 1 is hydrogen or a methyl group, R 2 is a C 3 -C 18 alkyl group, and m and n are each an integer of 0 to 10.

11. The adhesive composition of claim 10 , wherein the adhesive composition has a softening point of 50 to 150° C. and a melt viscosity of 300 to 10,000 cps at 160° C. and 200 to 8,000 cps at 180° C.

Assignees

• Kolon Inc

Inventors

• Lee Sang Hyun
• Park Jun Hyo
• Lee Joong Suk
• Cho Min Sik

Classifications

• C08F240/00 Primary

  Copolymers of hydrocarbons and mineral oils, e.g. petroleum resins · CPC title

• C09J145/00

  Adhesives based on homopolymers or copolymers of compounds having no unsaturated aliphatic radicals in a side chain, and having one or more carbon-to-carbon double bonds in a carbocyclic or in a heterocyclic system; Adhesives based on derivatives of such polymers (based on polymers of cyclic esters of polyfunctional acids C09J131/00; based on polymers of cyclic anhydrides or imides C09J135/00) · CPC title

• C08F8/04

  Reduction, e.g. hydrogenation · CPC title

• C09J157/02

  Copolymers of mineral oil hydrocarbons · CPC title

• C08F232/08

  having condensed rings (coumarone-indene polymers C08F244/00) · CPC title