CN114560989A - Polishing pad based on low-free polyurethane prepolymer and preparation method thereof - Google Patents
Polishing pad based on low-free polyurethane prepolymer and preparation method thereof Download PDFInfo
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- CN114560989A CN114560989A CN202210131797.3A CN202210131797A CN114560989A CN 114560989 A CN114560989 A CN 114560989A CN 202210131797 A CN202210131797 A CN 202210131797A CN 114560989 A CN114560989 A CN 114560989A
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- diisocyanate
- polishing pad
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- 238000005498 polishing Methods 0.000 title claims abstract description 50
- 229920001730 Moisture cure polyurethane Polymers 0.000 title claims abstract description 46
- 238000002360 preparation method Methods 0.000 title claims abstract description 27
- 125000005442 diisocyanate group Chemical group 0.000 claims abstract description 19
- 239000000945 filler Substances 0.000 claims abstract description 17
- 238000000034 method Methods 0.000 claims abstract description 14
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 13
- 239000002994 raw material Substances 0.000 claims abstract description 9
- 238000003786 synthesis reaction Methods 0.000 claims abstract description 5
- 229920005862 polyol Polymers 0.000 claims description 29
- 150000003077 polyols Chemical class 0.000 claims description 27
- 239000002245 particle Substances 0.000 claims description 25
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 24
- 239000011324 bead Substances 0.000 claims description 18
- 238000010438 heat treatment Methods 0.000 claims description 17
- 238000006243 chemical reaction Methods 0.000 claims description 15
- 239000011521 glass Substances 0.000 claims description 14
- 229920000909 polytetrahydrofuran Polymers 0.000 claims description 14
- 239000003054 catalyst Substances 0.000 claims description 13
- 238000003756 stirring Methods 0.000 claims description 12
- 239000004970 Chain extender Substances 0.000 claims description 10
- 150000001412 amines Chemical class 0.000 claims description 10
- 239000004005 microsphere Substances 0.000 claims description 10
- 238000002156 mixing Methods 0.000 claims description 10
- 239000007787 solid Substances 0.000 claims description 9
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 claims description 9
- 125000003158 alcohol group Chemical group 0.000 claims description 8
- 238000000465 moulding Methods 0.000 claims description 8
- 238000004073 vulcanization Methods 0.000 claims description 8
- 239000012974 tin catalyst Substances 0.000 claims description 7
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims description 6
- HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 claims description 6
- 229910010271 silicon carbide Inorganic materials 0.000 claims description 6
- ALQLPWJFHRMHIU-UHFFFAOYSA-N 1,4-diisocyanatobenzene Chemical compound O=C=NC1=CC=C(N=C=O)C=C1 ALQLPWJFHRMHIU-UHFFFAOYSA-N 0.000 claims description 5
- CTNICFBTUIFPOE-UHFFFAOYSA-N 2-(4-hydroxyphenoxy)ethane-1,1-diol Chemical compound OC(O)COC1=CC=C(O)C=C1 CTNICFBTUIFPOE-UHFFFAOYSA-N 0.000 claims description 5
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 claims description 4
- IBOFVQJTBBUKMU-UHFFFAOYSA-N 4,4'-methylene-bis-(2-chloroaniline) Chemical compound C1=C(Cl)C(N)=CC=C1CC1=CC=C(N)C(Cl)=C1 IBOFVQJTBBUKMU-UHFFFAOYSA-N 0.000 claims description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 4
- 229920001610 polycaprolactone Polymers 0.000 claims description 4
- 239000004632 polycaprolactone Substances 0.000 claims description 4
- -1 polyoxypropylene Polymers 0.000 claims description 4
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 3
- 239000010432 diamond Substances 0.000 claims description 3
- 229910003460 diamond Inorganic materials 0.000 claims description 3
- 239000011701 zinc Substances 0.000 claims description 3
- 229910052725 zinc Inorganic materials 0.000 claims description 3
- FKTHNVSLHLHISI-UHFFFAOYSA-N 1,2-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC=C1CN=C=O FKTHNVSLHLHISI-UHFFFAOYSA-N 0.000 claims description 2
- PTPIRFSXRFIROJ-UHFFFAOYSA-N 2-(3-hydroxyphenoxy)ethane-1,1-diol Chemical compound OC(O)COC1=CC=CC(O)=C1 PTPIRFSXRFIROJ-UHFFFAOYSA-N 0.000 claims description 2
- HDMRYQCGZUYLJJ-UHFFFAOYSA-N 4-chloro-2,6-bis(methylsulfanyl)benzene-1,3-diamine Chemical compound CSC1=CC(Cl)=C(N)C(SC)=C1N HDMRYQCGZUYLJJ-UHFFFAOYSA-N 0.000 claims description 2
- AOFIWCXMXPVSAZ-UHFFFAOYSA-N 4-methyl-2,6-bis(methylsulfanyl)benzene-1,3-diamine Chemical compound CSC1=CC(C)=C(N)C(SC)=C1N AOFIWCXMXPVSAZ-UHFFFAOYSA-N 0.000 claims description 2
- 229910052582 BN Inorganic materials 0.000 claims description 2
- PZNSFCLAULLKQX-UHFFFAOYSA-N Boron nitride Chemical compound N#B PZNSFCLAULLKQX-UHFFFAOYSA-N 0.000 claims description 2
- 239000005057 Hexamethylene diisocyanate Substances 0.000 claims description 2
- 239000005058 Isophorone diisocyanate Substances 0.000 claims description 2
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 claims description 2
- 229910052797 bismuth Inorganic materials 0.000 claims description 2
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 claims description 2
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 claims description 2
- 229910000420 cerium oxide Inorganic materials 0.000 claims description 2
- 239000010431 corundum Substances 0.000 claims description 2
- 229910052593 corundum Inorganic materials 0.000 claims description 2
- KORSJDCBLAPZEQ-UHFFFAOYSA-N dicyclohexylmethane-4,4'-diisocyanate Chemical compound C1CC(N=C=O)CCC1CC1CCC(N=C=O)CC1 KORSJDCBLAPZEQ-UHFFFAOYSA-N 0.000 claims description 2
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 claims description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 2
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 claims description 2
- ACCCMOQWYVYDOT-UHFFFAOYSA-N hexane-1,1-diol Chemical compound CCCCCC(O)O ACCCMOQWYVYDOT-UHFFFAOYSA-N 0.000 claims description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 2
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 claims description 2
- 238000002844 melting Methods 0.000 claims description 2
- 230000008018 melting Effects 0.000 claims description 2
- FSWDLYNGJBGFJH-UHFFFAOYSA-N n,n'-di-2-butyl-1,4-phenylenediamine Chemical compound CCC(C)NC1=CC=C(NC(C)CC)C=C1 FSWDLYNGJBGFJH-UHFFFAOYSA-N 0.000 claims description 2
- BMMGVYCKOGBVEV-UHFFFAOYSA-N oxo(oxoceriooxy)cerium Chemical compound [Ce]=O.O=[Ce]=O BMMGVYCKOGBVEV-UHFFFAOYSA-N 0.000 claims description 2
- 229920005906 polyester polyol Polymers 0.000 claims description 2
- 229920001451 polypropylene glycol Polymers 0.000 claims description 2
- ULWHHBHJGPPBCO-UHFFFAOYSA-N propane-1,1-diol Chemical compound CCC(O)O ULWHHBHJGPPBCO-UHFFFAOYSA-N 0.000 claims description 2
- 239000012948 isocyanate Substances 0.000 abstract description 15
- 150000002513 isocyanates Chemical class 0.000 abstract description 15
- 238000005516 engineering process Methods 0.000 abstract description 4
- 230000015572 biosynthetic process Effects 0.000 abstract description 3
- 239000000463 material Substances 0.000 description 15
- 239000004721 Polyphenylene oxide Substances 0.000 description 12
- 229920000570 polyether Polymers 0.000 description 12
- 239000000203 mixture Substances 0.000 description 11
- 239000004814 polyurethane Substances 0.000 description 11
- 229920002635 polyurethane Polymers 0.000 description 10
- 229920001971 elastomer Polymers 0.000 description 8
- 239000000806 elastomer Substances 0.000 description 8
- 230000018044 dehydration Effects 0.000 description 6
- 238000006297 dehydration reaction Methods 0.000 description 6
- 238000005187 foaming Methods 0.000 description 5
- 239000000178 monomer Substances 0.000 description 5
- 238000005086 pumping Methods 0.000 description 5
- 238000004321 preservation Methods 0.000 description 4
- 239000010409 thin film Substances 0.000 description 4
- 238000000227 grinding Methods 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- 230000007547 defect Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000010408 film Substances 0.000 description 2
- 230000020169 heat generation Effects 0.000 description 2
- 239000004065 semiconductor Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- VIOMIGLBMQVNLY-UHFFFAOYSA-N 4-[(4-amino-2-chloro-3,5-diethylphenyl)methyl]-3-chloro-2,6-diethylaniline Chemical compound CCC1=C(N)C(CC)=CC(CC=2C(=C(CC)C(N)=C(CC)C=2)Cl)=C1Cl VIOMIGLBMQVNLY-UHFFFAOYSA-N 0.000 description 1
- 239000006061 abrasive grain Substances 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 235000019437 butane-1,3-diol Nutrition 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000005304 optical glass Substances 0.000 description 1
- 238000007517 polishing process Methods 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920003225 polyurethane elastomer Polymers 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/48—Polyethers
- C08G18/4854—Polyethers containing oxyalkylene groups having four carbon atoms in the alkylene group
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
- C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
- C08G18/12—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step using two or more compounds having active hydrogen in the first polymerisation step
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/30—Low-molecular-weight compounds
- C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
- C08G18/3203—Polyhydroxy compounds
- C08G18/3206—Polyhydroxy compounds aliphatic
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/4009—Two or more macromolecular compounds not provided for in one single group of groups C08G18/42 - C08G18/64
- C08G18/4018—Mixtures of compounds of group C08G18/42 with compounds of group C08G18/48
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
- C08G18/4266—Polycondensates having carboxylic or carbonic ester groups in the main chain prepared from hydroxycarboxylic acids and/or lactones
- C08G18/4269—Lactones
- C08G18/4277—Caprolactone and/or substituted caprolactone
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/48—Polyethers
- C08G18/4804—Two or more polyethers of different physical or chemical nature
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/65—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen
- C08G18/66—Compounds of groups C08G18/42, C08G18/48, or C08G18/52
- C08G18/6666—Compounds of group C08G18/48 or C08G18/52
- C08G18/667—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38
- C08G18/6674—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38 with compounds of group C08G18/3203
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J9/00—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof
- C08J9/0066—Use of inorganic compounding ingredients
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J9/00—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof
- C08J9/32—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof from compositions containing microballoons, e.g. syntactic foams
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2203/00—Foams characterized by the expanding agent
- C08J2203/22—Expandable microspheres, e.g. Expancel®
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2375/00—Characterised by the use of polyureas or polyurethanes; Derivatives of such polymers
- C08J2375/04—Polyurethanes
- C08J2375/08—Polyurethanes from polyethers
Abstract
The invention discloses a polishing pad based on low-free polyurethane prepolymer and a preparation method thereof, the polishing pad adopts the low-free polyurethane prepolymer obtained by a low-free technology, the content of diisocyanate is lower than 0.1%, and the prepared polishing pad has good dynamic performance and long service life; the preparation method uses a low-free synthesis process to prepare the prepolymer, thereby greatly reducing the free content of isocyanate in the prepolymer. The polishing pad based on the low-free polyurethane prepolymer is prepared from the following raw materials in parts by mass: 100 parts of a low-free polyurethane prepolymer A component, 20-60 parts of a curing agent B component and 10-50 parts of a filler C component.
Description
Technical Field
The invention relates to a polishing pad and a preparation method thereof, in particular to a polishing pad based on low-free polyurethane prepolymer and a preparation method thereof.
Background
The CMP polishing pad is a key consumable in a wafer CMP process, and has large consumption, but the market share of CMP in China is almost completely monopolized by imported products at present, and the current situation needs to be solved urgently.
Polyurethane (PU) has unique soft segment and hard segment structures, wherein the soft segment composed of polyol endows the material with elasticity and toughness, and the hard segment composed of isocyanate endows the material with strength and hardness, and the special microphase structure determines that the PU can be used as an ideal polishing material and applied to the industries of optical parts, semiconductors and the like. In a high-precision polishing process, a polishing material is required to have a certain removal rate on a polished substance, and the friction coefficient between the polishing material and the polished substance is not too large, so that a large number of scratches are caused on the surface, the polishing material is required to have certain rigidity and flexibility, and the structural characteristics of PU just meet the requirement. The polyurethane has the advantages of good wear resistance, small deformation, high polishing efficiency and the like, and can be used as a polishing material or a polishing pad for semiconductors and optical glass. The conventional polyurethane polishing pad used in the prior art has the defects of poor dynamic performance, high internal heat generation and the like, and is difficult to meet the increasing market demand; the low-free polyurethane elastomer can solve the problem, the low-free polyurethane prepolymer has the advantages of regular molecules, uniform molecular activity, long operation time, high curing speed, good dynamic performance, low endogenous heat and the like, and the polishing pad with excellent performance can be prepared based on the low-free polyurethane prepolymer.
Disclosure of Invention
The invention aims to solve the problems and the defects in the prior art, and provides a polishing pad based on low-free polyurethane prepolymer, wherein the low-free polyurethane prepolymer is obtained by adopting a low-free technology, the content of diisocyanate in the low-free polyurethane prepolymer is lower than 0.1%, and the prepared polishing pad has good dynamic performance and long service life.
The invention also provides a preparation method of the polishing pad based on the low-free polyurethane prepolymer, which prepares the prepolymer by using a low-free synthesis process, greatly reduces the free content of isocyanate in the prepolymer, reduces the harm of volatile isocyanate to human health and environment, prolongs the pouring time, improves the dynamic performance of the product and prolongs the service life of the product. And meanwhile, the expanded beads are added, so that the foaming reaction is stable, and the problems of environmental protection and health are solved.
The invention is realized by the following technical scheme:
the polishing pad based on the low-free polyurethane prepolymer is prepared from the following raw materials in parts by mass:
100 parts of low-free polyurethane prepolymer A component
20-60 parts of curing agent B component
10-50 parts of a filler C component;
the component A of the low free polyurethane prepolymer is prepared from the following raw materials in parts by mass: 25-62 parts of polymeric polyol and 38-75 parts of diisocyanate; the curing agent B component is prepared from the following raw materials in parts by mass: 100 parts of amine or alcohol chain extender and 0.1-1 part of catalyst; the filler C component is prepared from the following raw materials in parts by mass: 100 parts of hollow glass beads, 10-30 parts of expanded beads and 35-100 parts of solid abrasive particles.
The polishing pad based on the low free polyurethane prepolymer has the further technical scheme that the polymeric polyol is one or the combination of polytetrahydrofuran polyol, polyester polyol, polycaprolactone polyol or polyoxypropylene ether polyol with the molecular weight of 400-3000; the diisocyanate is one or the combination of 4,4 '-diphenylmethane diisocyanate, toluene diisocyanate, p-phenylene diisocyanate, xylylene diisocyanate, modified 4,4' -diphenylmethane diisocyanate, hydrogenated MDI, hexamethylene diisocyanate and isophorone diisocyanate.
In a further technical scheme of the polishing pad based on the low-free polyurethane prepolymer, the amine chain extender may be one or a combination of 3,3 '-dichloro-4, 4' -diaminodiphenylmethane, dimethylthiotoluenediamine, 4 '-methylene-bis- (3-chloro-2, 6-diethylaniline), 2, 4-diamino-3, 5-dimethylthiochlorobenzene, 4' -bis-sec-butylaminodiphenylmethane, 1, 4-bis-sec-butylaminobenzene, and 3, 5-diamino-4-isobutyl chlorobenzoate; the alcohol chain extender is one or the combination of butanediol, propanediol, glycol, diethylene glycol, hexanediol, dipropylene glycol, hydroquinone dihydroxyethyl ether, resorcinol dihydroxyethyl ether and trimethylolpropane; the catalyst is one or the combination of an organic bismuth catalyst, an organic tin catalyst, an organic zinc catalyst or an organic amine catalyst.
The polishing pad based on the low free polyurethane prepolymer has the further technical scheme that the particle size of the hollow glass beads is 20-50 mu m; the particle size of the expanded bead is 10-50 μm; the solid abrasive particles are one or a combination of corundum, silicon carbide, diamond, cubic boron nitride and cerium oxide, and the particle size of the solid abrasive particles is 20nm-50 mu m.
The preparation method of the polishing pad based on the low-free polyurethane prepolymer comprises the following steps:
preparing a component A of a low-free polyurethane prepolymer: heating and melting the polymeric polyol, sucking the polymeric polyol into a reaction kettle in vacuum, heating to 90-110 ℃, and removing water in the polyol under 1kPa until the water content is less than or equal to 0.03 wt%; continuously dropwise adding the dehydrated polymeric polyol into diisocyanate for synthesis reaction, wherein the molar ratio of the polymeric polyol to the diisocyanate is 1: 2-8, reacting for 2-4h at 80-90 ℃, and removing bubbles in a stirring state after the reaction is finished; after defoaming, the synthesized product is injected into a film evaporator and a short-range evaporator, and free diisocyanate is removed under the conditions of 120-140 ℃ and the vacuum degree of 5Pa-10Pa to obtain a component A of the low-free polyurethane prepolymer, wherein the content of the free diisocyanate in the low-free polyurethane prepolymer is less than 0.1 wt%;
preparation of curing agent B component: heating the amine or alcohol chain extender to 90-130 ℃, dehydrating under 1kPa in vacuum until the water content is less than or equal to 0.03 wt%, and then adding a catalyst and stirring uniformly;
preparation of the component C of the filler: heating the hollow glass microspheres and the wear-resistant filler to 110 ℃ at the temperature of 100 ℃, dehydrating in vacuum at the pressure of below 1kPa until the moisture content is less than or equal to 0.03 wt%, adding the expanded microspheres, and uniformly mixing;
preparing a polishing pad: and uniformly mixing the component A, the component B and the component C according to the mass ratio at 40-90 ℃, pouring into a mold for molding, and performing post-vulcanization to obtain the polishing pad.
The preparation method of the polishing pad based on the low free polyurethane prepolymer further adopts the technical scheme that the heating temperature of the polymeric polyol is 90-110 ℃, and the vacuum degree is 1 kPa; the heating temperature of the amine or alcohol chain extender is 90-130 ℃, and the vacuum degree is 1 kPa; the heating temperature of the hollow glass beads and the wear-resistant filler is 90-110 ℃, and the vacuum degree is 1 kPa.
Compared with the prior art, the invention has the following beneficial effects:
the invention adopts low-free synthesis technology, in the preparation process of the low-free prepolymer, a large amount of diisocyanate monomers are excessive, an NCO group on the free diisocyanate monomer has higher activity relative to an NCO group on an oligomer, and polymer polyol reacts with an NCO group on the free diisocyanate monomer more easily, so that a large amount of A-B-A three-unit structures are generated in a prepolymer system. And then separating free diisocyanate monomers in the system to obtain the low-free prepolymer with low free diisocyanate content, narrow relative molecular mass distribution and more regular molecular structure. Therefore, compared with the conventional polyurethane prepolymer, the elastomer prepared from the low-free prepolymer has a more regular molecular chain structure, so that a more regular micro-area structure can be formed, and the elastomer with higher comprehensive performance can be obtained. The content of free TDI monomer in the low-free TDI prepolymer is below 0.1%, and the steam pressure of the conventional TDI prepolymer is at least 5 times that of the TDI prepolymer with the free TDI content of 0.1%. Therefore, the low-free polyurethane prepolymer can well improve the working operation environment and is safer and more sanitary.
The prepolymer prepared by adopting the low-free technology has lower viscosity, longer service life in a kettle and longer storage life besides the content of free isocyanate being less than 0.1 percent, and the prepared product has better aging resistance, low internal heat generation and higher dynamic mechanical property. In the preparation process of the polishing pad, the expanded beads are adopted for foaming, compared with the foaming process in the conventional process in which water is used for foaming, the foaming process is more stable, and the density of the product is better controlled.
Detailed Description
The present invention will be described below with reference to specific examples, but the present invention is not limited to these examples.
Example 1
Preparing a component A of a low-free polyurethane prepolymer: the method comprises the following steps of dehydrating 940g of polytetrahydrofuran polyether with the molecular weight of 1000, 30g of 1,4 butanediol and 30g of 1,3 butanediol at the temperature of 95 ℃ and the vacuum degree of 1kPa until the content of water is below 0.03%, slowly adding the dehydrated polytetrahydrofuran polyether into 828g of toluene diisocyanate, slowly heating to 85 ℃, and carrying out heat preservation reaction for 2 hours. And after the reaction is finished, stirring to remove bubbles in the product. And after defoaming, pumping the material into a film evaporator. Then the mixture is gradually pumped into a short-range evaporator, and the excessive toluene diisocyanate is removed under the conditions that the temperature is 120 ℃ and the vacuum degree is 5-10 Pa. And detecting that the content of free isocyanate in the prepolymer is below 0.1 percent to obtain the qualified product. In the above process, the molar ratio of isocyanate to polyol is 2.95, and the final prepolymer NCO content is 8.6%.
Preparation of curing agent B component: heating 100 parts of 3,3 '-dichloro-4, 4' -diaminodiphenylmethane to 110 ℃, dehydrating under 1kPa in vacuum until the water content is less than or equal to 0.03 wt%, and then adding 0.1 part of organic tin catalyst and stirring uniformly for later use.
Preparation of the component C of the filler: 100 parts of hollow glass microspheres with the grain size of 40 microns and 35 parts of silicon carbide solid abrasive grains with the grain size of 20nm are uniformly mixed, vacuum dehydration is carried out at the temperature of 120 ℃ and the pressure of below 1000Pa until the moisture content is less than or equal to 0.03 weight percent, and 20 parts of expanded microspheres with the grain size of 10 microns are added and uniformly mixed.
Preparing a polyurethane polishing pad: mixing the A, B, C components according to the ratio of 100: 26: 15, pouring the mixture into a mold for molding, and performing post-vulcanization to obtain an elastomer with the Shore hardness of 50D, namely the polishing pad based on the low-free polyurethane prepolymer. The properties of the test sample are shown in Table 1.
Example 2
Preparing a component A of the low-free polyurethane prepolymer: 900g of polytetrahydrofuran polyether with the molecular weight of 650 and 100g of polytetrahydrofuran polyether with the molecular weight of 1000 are dehydrated at the temperature of 95 ℃ and the vacuum degree of 1kPa until the content of water is below 0.03 percent, then the polytetrahydrofuran polyether is slowly added into 950g of p-phenylene diisocyanate, the temperature is rapidly reduced to 85 ℃ in a water bath, and the heat preservation reaction is carried out for 2 hours. And after the reaction is finished, stirring to remove bubbles in the product. And after defoaming, pumping the material into a thin film evaporator. Then the mixture is gradually pumped into a short-range evaporator, and the excessive toluene diisocyanate is removed under the conditions that the temperature is 120 ℃ and the vacuum degree is 5-10 Pa. And detecting that the content of free isocyanate in the prepolymer is below 0.1 percent to obtain the qualified product. In the above process, the molar ratio of isocyanate to polyol is 4, and the final prepolymer NCO content is 7.4%.
Preparation of curing agent B component: 100 portions of hydroquinone dihydroxyethyl ether are dehydrated in vacuum at 120 ℃ and below 1000Pa until the water content is less than or equal to 0.03 weight percent, and then 0.2 portion of organic tin catalyst is added and evenly stirred for standby.
Preparation of the component C of the filler: 100 parts of hollow glass microspheres with the particle size of 20 microns and 100 parts of silicon carbide grinding materials with the particle size of 50 microns are uniformly mixed, vacuum dehydration is carried out at the temperature of 120 ℃ and the pressure of below 1000Pa until the water content is less than or equal to 0.03 wt%, and 30 parts of expanded microspheres with the particle size of 50 microns are added and uniformly mixed.
Preparing a polyurethane polishing pad: mixing the A, B, C components according to the ratio of 100: 20: 10, pouring the mixture into a mold for molding, and performing post-vulcanization to obtain an elastomer with the Shore hardness of 55D, namely the polishing pad based on the low-free polyurethane prepolymer. The properties of the test sample are shown in Table 1.
Example 3
Preparing a component A of a low-free polyurethane prepolymer: 227g of polycaprolactone with the molecular weight of 1000 and 772g of polytetrahydrofuran polyether with the molecular weight of 650 are dehydrated at the temperature of 95 ℃ and the vacuum degree of 1kPa until the content of water is below 0.03 percent, then the dehydrated polycaprolactone is slowly added into 739g of toluene diisocyanate, the temperature is slowly raised to 85 ℃, and the reaction is kept for 2 hours. And after the reaction is finished, stirring to remove bubbles in the product. And after defoaming, pumping the material into a thin film evaporator. Then the mixture is gradually pumped into a short-range evaporator, and the excessive toluene diisocyanate is removed under the conditions that the temperature is 120 ℃ and the vacuum degree is 5-10 Pa. And detecting that the content of free isocyanate in the prepolymer is below 0.1 percent to obtain the qualified product. In the above process, the molar ratio of isocyanate to polyol is 3, and the NCO content of the final prepolymer is 7.3%.
Preparation of curing agent B component: heating 100 parts of 4,4' -methylene-bis (3-chloro-2, 6-diethylaniline) to 100 ℃, dehydrating under 1kPa in vacuum until the water content is less than or equal to 0.03 wt%, and then adding 0.1 part of organic zinc catalyst and stirring uniformly for later use.
Preparation of the component C of the filler: 100 parts of hollow glass microspheres with the particle size of 40 microns and 35 parts of diamond solid abrasive particles with the particle size of 50 microns are uniformly mixed, vacuum dehydration is carried out at the temperature of 120 ℃ and the pressure of below 1000Pa until the moisture content is less than or equal to 0.03 weight percent, and 1.5 percent of expanded microspheres are added and uniformly mixed.
Preparing a polyurethane polishing pad: mixing the A, B, C components according to the ratio of 100: 31: 15, pouring the mixture into a mold for molding, and performing post-vulcanization to obtain an elastomer with the Shore hardness of 52D, namely the polishing pad based on the low-free polyurethane prepolymer. The properties of the test sample are shown in Table 1.
Example 4
Prepolymer A was the same as in example 1.
Preparation of curing agent B component: heating 3,3 '-dichloro-4, 4' -diaminodiphenylmethane to 110 ℃, dehydrating in vacuum under 1kPa until the water content is less than or equal to 0.03 wt%, and then adding an organic tin catalyst to stir uniformly for later use.
Preparation of the component C of the filler: 100 parts of hollow glass beads with the particle size of 40 microns and 50 parts of zirconia solid abrasive particles with the particle size of 40nm are uniformly mixed, vacuum dehydration is carried out at the temperature of 120 ℃ and the pressure of below 1000Pa until the moisture content is less than or equal to 0.03 weight percent, and 10 parts of expanded beads are added and uniformly mixed.
Preparing a polyurethane polishing pad: mixing the A, B, C components according to the ratio of 100: 26: 16, pouring the mixture into a mold for molding, and performing post-vulcanization to obtain an elastomer with the Shore hardness of 47D, namely the polishing pad based on the low-free polyurethane prepolymer. The properties of the test sample are shown in Table 1.
Example 5
Preparing a component A of a low-free polyurethane prepolymer: 200g of polytetrahydrofuran polyether with the molecular weight of 650 and 800g of polytetrahydrofuran polyether with the molecular weight of 1000 are dehydrated at the temperature of 95 ℃ and the vacuum degree of 1kPa until the content of water is below 0.03 percent, then the polytetrahydrofuran polyether is slowly added into 620g of p-phenylene diisocyanate, the temperature is rapidly reduced to 85 ℃ in a water bath, and the heat preservation reaction is carried out for 2 hours. And after the reaction is finished, stirring to remove bubbles in the product. And after defoaming, pumping the material into a thin film evaporator. Then the mixture is gradually pumped into a short-range evaporator, and the excessive toluene diisocyanate is removed under the conditions that the temperature is 120 ℃ and the vacuum degree is 5-10 Pa. And detecting that the content of free isocyanate in the prepolymer is below 0.1 percent to obtain the qualified product. In the above process, the molar ratio of isocyanate to polyol is 4, and the NCO content of the final prepolymer is 5.2%.
Preparation of curing agent B component: 100 portions of hydroquinone dihydroxyethyl ether are dehydrated in vacuum at 120 ℃ and below 1000Pa until the water content is less than or equal to 0.03 weight percent, and then 0.2 portion of organic tin catalyst is added and evenly stirred for standby.
Preparation of the component C of the filler: 100 parts of hollow glass beads with the particle size of 40 microns and 35 parts of silicon carbide grinding materials with the particle size of 20nm are uniformly mixed, vacuum dehydration is carried out at the temperature of 120 ℃ and the pressure of below 1000Pa until the water content is less than or equal to 0.03 weight percent, and 15 parts of expanded beads are added and uniformly mixed.
Preparing a polyurethane polishing pad: mixing the A, B, C components according to the ratio of 100: 20: 10, pouring the mixture into a mold for molding, and performing post-vulcanization to obtain an elastomer with the Shore hardness of 50D, namely the polishing pad based on the low-free polyurethane prepolymer. The properties of the test sample are shown in Table 1.
Example 6
Preparing a component A of the low-free polyurethane prepolymer: 900g of polytetrahydrofuran polyether with the molecular weight of 1000 and 100g of polytetrahydrofuran polyether with the molecular weight of 2000 are dehydrated at the temperature of 95 ℃ and the vacuum degree of 1kPa until the content of water is below 0.03 percent, then the dehydrated polytetrahydrofuran polyether is slowly added into 420g of p-phenylene diisocyanate, the temperature is rapidly reduced to 85 ℃ in a water bath, and the heat preservation reaction is carried out for 2 hours. And after the reaction is finished, stirring to remove bubbles in the product. And after defoaming, pumping the material into a thin film evaporator. Then the mixture is gradually pumped into a short-range evaporator, and the excessive toluene diisocyanate is removed under the conditions that the temperature is 120 ℃ and the vacuum degree is 5-10 Pa. And detecting that the content of free isocyanate in the prepolymer is below 0.1 percent to obtain the qualified product. In the above process, the molar ratio of isocyanate to polyol is 4, and the NCO content of the final prepolymer is 3.9%.
Preparation of curing agent B component: 100 portions of hydroquinone dihydroxyethyl ether are dehydrated in vacuum at 120 ℃ and below 1000Pa until the water content is less than or equal to 0.03 weight percent, and then 0.2 portion of organic tin catalyst is added and evenly stirred for standby.
Preparation of the component C of the filler: 100 parts of hollow glass beads with the particle size of 40 microns and 40 parts of silicon carbide grinding materials with the particle size of 20nm are uniformly mixed, vacuum dehydration is carried out at the temperature of 120 ℃ and the pressure of below 1000Pa until the water content is less than or equal to 0.03 weight percent, and 2 percent of expanded beads are added and uniformly mixed.
Preparing a polyurethane polishing pad: mixing the A, B, C components according to the ratio of 100: 20: 10, pouring the mixture into a mold for molding, and performing post-vulcanization to obtain an elastomer with the Shore hardness of 45D, namely the polishing pad based on the low-free polyurethane prepolymer. The properties of the test sample are shown in Table 1.
Table 1: polishing pad performance summary based on low free polyurethane prepolymers
Claims (6)
1. The polishing pad based on the low-free polyurethane prepolymer is characterized by being prepared from the following raw materials in parts by mass:
100 parts of low-free polyurethane prepolymer A component
20-60 parts of curing agent B component
10-50 parts of a filler C component;
the component A of the low free polyurethane prepolymer is prepared from the following raw materials in parts by mass: 25-62 parts of polymeric polyol and 38-75 parts of diisocyanate; the curing agent B component is prepared from the following raw materials in parts by mass: 100 parts of amine or alcohol chain extender and 0.1-1 part of catalyst; the filler C component is prepared from the following raw materials in parts by mass: 100 parts of hollow glass beads, 10-30 parts of expanded beads and 35-100 parts of solid abrasive particles.
2. The polishing pad of claim 1, wherein the polymeric polyol is one or a combination of polytetrahydrofuran polyol, polyester polyol, polycaprolactone polyol or polyoxypropylene ether polyol with molecular weight of 400-3000; the diisocyanate is one or the combination of 4,4 '-diphenylmethane diisocyanate, toluene diisocyanate, p-phenylene diisocyanate, xylylene diisocyanate, modified 4,4' -diphenylmethane diisocyanate, hydrogenated MDI, hexamethylene diisocyanate and isophorone diisocyanate.
3. The polishing pad of claim 1, wherein the amine chain extender is one or a combination of 3,3 '-dichloro-4, 4' -diaminodiphenylmethane, dimethylthiotoluenediamine, 4 '-methylene-bis- (3-chloro-2, 6-diethylaniline), 2, 4-diamino-3, 5-dimethylthiochlorobenzene, 4' -bis-sec-butylaminodiphenylmethane, 1, 4-bis-sec-butylaminobenzene, 3, 5-diamino-4-isobutyl chlorobenzoate; the alcohol chain extender is one or the combination of butanediol, propanediol, glycol, diethylene glycol, hexanediol, dipropylene glycol, hydroquinone dihydroxyethyl ether, resorcinol dihydroxyethyl ether and trimethylolpropane; the catalyst is one or the combination of an organic bismuth catalyst, an organic tin catalyst, an organic zinc catalyst or an organic amine catalyst.
4. The polishing pad based on low-free polyurethane prepolymer as claimed in claim 1, wherein the hollow glass beads have a particle size of 20 to 50 μm; the particle size of the expanded bead is 10-50 μm; the solid abrasive particles are one or a combination of corundum, silicon carbide, diamond, cubic boron nitride and cerium oxide, and the particle size of the solid abrasive particles is 20nm-50 mu m.
5. A method for preparing a polishing pad based on a low free polyurethane prepolymer as claimed in any of claims 1 to 4, comprising the steps of:
preparing a component A of a low-free polyurethane prepolymer: heating and melting the polymeric polyol, sucking the polymeric polyol into a reaction kettle in vacuum, heating to 90-110 ℃, and removing water in the polyol under 1kPa until the water content is less than or equal to 0.03 wt%; continuously dropwise adding the dehydrated polymeric polyol into diisocyanate for synthesis reaction, wherein the molar ratio of the polymeric polyol to the diisocyanate is 1: 2-8, reacting for 2-4h at 80-90 ℃, and removing bubbles in a stirring state after the reaction is finished; after defoaming, the synthesized product is injected into a film evaporator and a short-range evaporator, and free diisocyanate is removed under the conditions of 120-140 ℃ and the vacuum degree of 5Pa-10Pa to obtain a component A of the low-free polyurethane prepolymer, wherein the content of the free diisocyanate in the low-free polyurethane prepolymer is less than 0.1 wt%;
preparation of curing agent B component: heating the amine or alcohol chain extender to 90-130 ℃, dehydrating under 1kPa in vacuum until the water content is less than or equal to 0.03 wt%, and then adding a catalyst and stirring uniformly;
preparation of the component C of the filler: heating the hollow glass microspheres and the wear-resistant filler to 110 ℃ at the temperature of 100 ℃, dehydrating in vacuum at the pressure of below 1kPa until the moisture content is less than or equal to 0.03 wt%, adding the expanded microspheres, and uniformly mixing;
preparing a polishing pad: and uniformly mixing the component A, the component B and the component C according to the mass ratio at 40-90 ℃, pouring into a mold for molding, and performing post-vulcanization to obtain the polishing pad.
6. The method of claim 5, wherein the polymeric polyol is heated at 90-110 ℃ under a vacuum of 1 kPa; the heating temperature of the amine or alcohol chain extender is 90-130 ℃, and the vacuum degree is 1 kPa; the heating temperature of the hollow glass beads and the wear-resistant filler is 90-110 ℃, and the vacuum degree is 1 kPa.
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