IP Library Granted Patent US 11,807,710
Granted Patent B2
US 11,807,710 · App. 17/503,422 · Granted Nov 7, 2023

UV-curable resins used for chemical mechanical polishing pads

Inventors: Chen-Chih Tsai (Naperville, IL); Eric S. Moyer (Aurora, IL); Ping Huang (Naperville, IL)
Assignee: CMC Materials, Inc.
C08G18/8116B24B37/24C08F2/48C08G18/10C08G18/6725C08K3/04
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Quick Facts
Patent No.
US 11,807,710
App. No.
17/503,422
Granted
Nov 7, 2023
Kind
B2
Abstract

The invention provides a UV-curable resin for forming a chemical-mechanical polishing pad comprising: (a) one or more acrylate blocked isocyanates; (b) one or more acrylate monomers; and (c) a photoinitiator. The invention also provides a method of forming a chemical-mechanical polishing pad using the UV-curable resin.

Claims (27)

1. A UV-curable resin for forming a chemical-mechanical polishing pad comprising:

(a) an acrylate blocked isocyanate component, wherein the acrylate blocked isocyanate component comprises an acrylate blocking agent and an isocyanate terminated urethane prepolymer, wherein the acrylate blocking agents are selected from 2-hydroxyethyl acrylate (HEA), 2-hydroxyethyl methacrylate (HEMA), 2-(tert-butylamino) ethyl methacrylate (TBEMA), and 3-(acryloyloxy)-2-hydroxypropyl methacrylate (AHPMA), wherein the acrylate blocking agent and the isocyanate terminated urethane prepolymer form a capped prepolymer, and wherein there is a ratio of particular capped prepolymers in the acrylate blocked isocyanate component;

(b) one or more acrylate monomers; and

(c) a photoinitiator.

2. The UV-curable resin of claim 1 , wherein the acrylate blocked isocyanate component comprises polyisocyanates.

3. The UV-curable resin of claim 1 , wherein the isocyanate-terminated urethane prepolymers comprise aromatic prepolymers, aliphatic prepolymers, or combinations thereof.

4. The UV-curable resin of claim 1 , wherein the acrylate blocking agents forming the capped prepolymers are 2-(tert-butylamino) ethyl methacrylate and 2-hydroxyethyl acrylate.

5. The UV-curable resin of claim 4 , wherein the ratio of 2-(tert-butylamino) ethyl methacrylate capped prepolymers: 2-hydroxyethyl acrylate capped prepolymers is greater than 50:50.

6. The UV-curable resin of claim 5 , wherein the ratio of 2-(tert-butylamino) ethyl methacrylate capped prepolymers: 2-hydroxyethyl acrylate capped prepolymers is 75:25.

7. The UV-curable resin of claim 1 , wherein the one or more acrylate monomers are selected from isobornyl methacrylate (IBMA), 2-carboxyethyl acrylate (CEA), 2-hydroxyethyl acrylate (HEA), ethylene glycol dimethacrylate (EGDMA), neopentyl glycol dimethacrylate (NGDMA), 3-(acryloyloxy)-2-hydroxypropyl methacrylate (AHPMA) and trimethylolpropane triacrylate (TMPTA).

8. The UV-curable resin of claim 1 , wherein the photoinitiator is diphenylphosphine oxide (TPO).

9. The UV-curable resin of claim 1 further comprising an additive selected from stabilizers, plasticizers, porogen fillers, pigments and combinations thereof.

10. A chemical-mechanical polishing pad comprising polymerized material formed from polymerization of the UV-curable resin of claim 1 .

11. A method of forming a polishing pad comprising:

(a) preparing a UV-curable resin comprising:

(i) an acrylate blocked isocyanate component, wherein the acrylate blocked isocyanate component comprises an acrylate blocking agent and an isocyanate terminated urethane prepolymer, wherein the acrylate blocking agents are selected from 2-hydroxyethyl acrylate (HEA), 2-hydroxyethyl methacrylate (HEMA), 2-(tert-butylamino) ethyl methacrylate (TBEMA), and 3-(acryloyloxy)-2-hydroxypropyl methacrylate (AHPMA), wherein the acrylate blocking agent and the isocyanate terminated urethane prepolymer form a capped prepolymer, and wherein there is a ratio of particular capped prepolymers in the acrylate blocked isocyanate component;

(ii) one or more acrylate monomers, and

(iii) a photoinitiator;

(b) exposing a thin layer of the UV-curable resin to UV light, initiating a polymerization reaction, and thus forming a thin layer of solidified pad material;

wherein the method does not include a thermal curing step.

12. The method of claim 11 , wherein the isocyanate-terminated urethane prepolymers comprise aromatic prepolymers, aliphatic prepolymers, or combinations thereof.

13. The method of claim 11 , wherein the acrylate blocking agents forming the capped prepolymers are 2-(tert-butylamino) ethyl methacrylate and 2-hydroxyethyl acrylate.

14. The method of claim 13 , wherein the ratio of 2-(tert-butylamino) ethyl methacrylate capped prepolymers: 2-hydroxyethyl acrylate capped prepolymers is greater than 50:50.

15. The method of claim 14 , wherein the ratio of 2-(tert-butylamino) ethyl methacrylate capped prepolymers: 2-hydroxyethyl acrylate capped prepolymers is 75:25.

16. The method of claim 11 , wherein the one or more acrylate monomers are selected from isobornyl methacrylate (IBMA), 2-carboxyethyl acrylate (CEA), 2-hydroxyethyl acrylate (HEA), ethylene glycol dimethacrylate (EGDMA), neopentyl glycol dimethacrylate (NGDMA), 3-(acryloyloxy)-2-hydroxypropyl methacrylate (AHPMA) and trimethylolpropane triacrylate (TMPTA).

17. The method of claim 11 , wherein he photoinitiator is diphenylphosphine oxide (TPO).

18. The method of claim 11 , further comprising an additive selected from stabilizers, plasticizers, porogen fillers, pigments and combinations thereof.

Assignments (4)
CHANGE OF NAME Recorded Nov 8, 2023
From: CMC MATERIALS, INC.
To: CMC MATERIALS LLC
Reel/Frame 065517/0783 →
SECURITY INTEREST Recorded Jul 8, 2022
From: CMC MATERIALS, INC.; INTERNATIONAL TEST SOLUTIONS, LLC; QED TECHNOLOGIES INTERNATIONAL, INC.
To: MORGAN STANLEY SENIOR FUNDING, INC., AS COLLATERAL AGENT
Reel/Frame 060615/0001 →
SECURITY INTEREST Recorded Jul 8, 2022
From: ENTEGRIS, INC.; ENTEGRIS GP, INC.; POCO GRAPHITE, INC.; CMC MATERIALS, INC.; INTERNATIONAL TEST SOLUTIONS, LLC; QED TECHNOLOGIES INTERNATIONAL, INC.
To: TRUIST BANK, AS NOTES COLLATERAL AGENT
Reel/Frame 060613/0072 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 18, 2021
From: TSAI, CHEN-CHIH; MOYER, ERIC S.; HUANG, PING
To: CMC MATERIALS, INC.
Reel/Frame 057814/0550 →
Continuity (2)
Provisional Application 63093543 · Oct 19, 2020
Related Publication 20220119586A1 · Apr 21, 2022