Patent US6938039B1 successfully refreshed from Google Patents.
US5011901A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Polyorganosiloxane with chloromethyl groups
Assignee: DuPont Toray Specialty Materials KK
•
Filing: 1989-11-13
•
Granted: 1991-04-30
•
Expires: 2009-11-13
Abstract
Abstract Polyorganosiloxane which are useful as resist materials for use in microprocesses such as large scale integration device fabrication are those of the formula ##STR1## where R 1 is a monovalent hydrocarbon group having 1 to 6 carbon atoms; R 2 is a hydrogen atom or a monovalent hydrocarbon group having 1 to 6 carbon atoms; x and z are positive numbers; y is zero or a positive number; and x, y, and z have values such that their ratios are 0.3≦(x+y)/z≦4; and zero ≦y/x≦100. The polyorganosiloxanes can be prepared by cohydrolysis or condensation reactions of hydrolyzable group-containing organosilanes or disiloxanes with tetrafunctional hydrolyzable silanes.
Inventors
- 👤 Yoshimi Fukutani
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-05 12:02
CPC Classifications
C; C08; C08G; C08G77/00; C08G77/04; C08G77/22; C08G77/24; G; G03; G03F; G03F7/00; G03F7/004; G03F7/075; G03F7/0757
Claims Analysis
Total Claims: 10
Claim 1
Independent Claim
76 words
Polyorganosiloxane with a molecular weight of 500 to 500,000 which has the following general formula ##STR23## in which R 1 is a monovalent hydrocarbon group having 1 to 6 carbon atoms; R 2 is a hydrogen atom or a monovalent hydrocarbon group having 1 to 6 carbon atoms; x and z are positive numbers; y is zero or a positive number; and x, y, and z have values such that their ratios are 0.3≦(x+y)/z≦4; and zero≦y/x≦100.
Claim 2
Dependent Claim
76 words
Polyorganosiloxane with a molecular weight of 500 to 500,000 which has the following general formula ##STR23## in which R 1 is a monovalent hydrocarbon group having 1 to 6 carbon atoms; R 2 is a hydrogen atom or a monovalent hydrocarbon group having 1 to 6 carbon atoms; x and z are positive numbers; y is zero or a positive number; and x, y, and z have values such that their ratios are 0.3≦(x+y)/z≦4; and zero≦y/x≦100.
Claim 3
Dependent Claim
16 words
The polyorganosiloxane according to claim 1 which is solid at room temperature and for which 0.3≦(x+y)/z≦1.0.
Claim 4
Dependent Claim
117 words
The polyorganosiloxane according to claim 1 which is made from reaction of 1,3-bis(alpha-chloromethyl)-1,1,3,3-tetramethyldisiloxane, hexamethyldisiloxane, and tetraethoxysilane, and which is a solid at room temperature having the values for 1 HNMR delta (ppm) of 0.3 (5.8H, br, CH 3 Si), 1.3 (0.5H, br, CH 3 CH 2 OSi), 2.7 (0.2H, br, ClCH 2 Si), 3.3 (0.3H, br, CH 3 CH 2 OSi); the values for 29 SiNMR delta (ppm) of 13 (0.57Si, br, (CH 3 ) 3 SiO 1/2 ), 7 (0.11Si, br, ClCH 2 (CH 3 ) 2 SiO 1/2 ), -100 (0.16Si, ROSiO 3/2 ), -110 (0.84Si, br, SiO 4/2 ); an M w of 1.6×10 4 ; and an M n of 4.7×10 3 .
Claim 5
Dependent Claim
137 words
The polyorganosiloxane according to claim 1 which is made from reaction of 1,3-bis(alpha-chloromethyl)-1,1,3,3-tetramethyldisiloxane, 1,3-divinyl-1,1,3,3-tetramethyldisiloxane, and tetraethoxysilane, and which is a solid at room temperature having the values for 1 HNMR delta (ppm) of 0.3 (4.2H, br, CH 3 Si), 1.3 (0.4H, br, CH 3 CH 2 OSi), 2.7 (0.4H, br, ClCH 2 Si), 3.3 (0.3H, br, CH 3 CH 2 OSi), 6.0 (0.9H, br, CH 2 ═CH--Si); the values for 29 SiNMR delta (ppm) of 13 (0.16Si, br, (CH 3 ) 3 SiO 1/2 ), 7 (0.18Si, br, ClCH 2 (CH 3 ) 2 SiO 1/2 ), 0 (0.28Si, br, CH 2 ═CH--(CH 3 ) 2 SiO 1/2 ), -100 (0.13Si, br, ROSiO 3/2 ), -110 (0.87 Si, br, SiO 4/2 ); an M w of 1.4×10 4 ; and an M n of 4.3×10 3 .
Claim 6
Dependent Claim
117 words
The polyoganosiloxane according to claim 1 which is made from reaction of alpha-chloromethyldimethylchlorosilane and tetraethoxysilane, and which is a solid at room temperature having the values for 1 HNMR delta (ppm) of 0.3 (5.4H, br, CH 3 Si), 1.3 (0.5H, br, CH 3 CH 2 OSi), 2.7 (1.4H, br, ClCH 2 Si), 3.3 (0.3H, br, CH 3 CH 2 OSi); the values for 29 SiNMR delta (ppm) of 13 (0.15Si, br, (CH 3 ) 3 SiO 1/2 ), 7 (0.65Si, br, ClCH 2 (CH 3 ) 2 SiO 1/2 ), -100 (0.15Si, br, ROSiO 3/2 ), -110 (0.85Si, br, SiO 4/2 ); an M w of 2.7×10 3 ; and an M n of 1.9×10 3 .
Claim 7
Dependent Claim
118 words
The polyorganosiloxane according to claim 1 which is made from reaction of alpha-chloromethyldimethylchlorosilane, trimethylchlorosilane, and tetraethoxysilane, and which is a solid at room temperature having the values for 1 HNMR delta (ppm) of 0.3 (4.8H, br, CH 3 Si), 1.3 (0.5H, br, CH 3 CH 2 OSi), 2.7 (0.5H, br, ClCH 2 Si), 3.3 (0.3H, br, CH 3 CH 2 OSi); the value for 29 SiNMR delta (ppm) of 13 (0.38Si, br, (CH 3 ) 3 SiO 1/2 ), 7 (0.22Si, br, ClCH 2 (CH 3 ) 2 SiO 1/2 ), -100 (0.16Si, br, ROSiO 3/2 ), -110 (0.84Si, br, SiO 4/2 ); an M w of 2.4×10 4 ; and an M n of 5.4×10 3 .
Claim 8
Dependent Claim
117 words
The polyorganosiloxane according to claim 1 which is made from reaction of 1,3-bis(alpha-chloromethyl)-1,1,3,3-tetramethyldisiloxane, hexamethyldisloxane, and tetraethoxysilane, and which is a liquid at room temperature having the values for 1 HNMR delta (ppm) of 0.3 (14.6H, br, CH 3 Si), 1.3 (0.2H, br, CH 3 CH 2 OSi), 2.7 (0.8H, br, ClCH 2 Si), 3.3 (0.1H, br, CH 3 CH 2 OSi); the values for 29 SiNMR delta (ppm): 13 (1.36Si, br, (CH 3 ) 3 SiO 1/2 ), 7 (0.40Si, br, ClCH 2 (CH 3 ) 2 SiO 1/2 ), -100 (0.08Si, br, ROSiO 3/2 ), -110 (0.92Si, br, SiO 4/2 ); an M w of 1.2×10 3 ; and an M n of 1.1×10 3 .
Claim 9
Independent Claim
192 words
A method for the preparation of polyorganosiloxane with a molecular weight of 500 to 500,000 which has the following general formula ##STR24## in which R 1 is a monovalent hydrocarbon group having 1 to 6 carbon atoms; R 2 is a hydrogen atom or a monovalent hydrocarbon group having 1 to 6 carbon atoms; x and z are positive numbers; y is zero or a positive number; and x, y, and z have values such that their ratios are 0.3≦(x+y)/z≦4; and zero≦y/x≦100, said method comprising cohydrolysis or condensation reactions of (A) hydrolyzable group-containing organosilane as represented by the following general formula ##STR25## in which R 1 as defined as above, and M is a hydrolyzable group or (A') disiloxane as represented by the following general formula ##STR26## in which R 1 is defined as above, (B) hydrolyzable group-containing organosilane as represented by the following general formula ##STR27## in which R 1 , R 2 , and M are defined as above or (B') disiloxane as represented by the following general formula ##STR28## and (C) hydrolyzable silane as represented by the following general formula SiM.sub.4 M in the formula is defined as above.
Claim 10
Independent Claim
192 words
A method for the preparation of polyorganosiloxane with a molecular weight of 500 to 500,000 which has the following general formula ##STR24## in which R 1 is a monovalent hydrocarbon group having 1 to 6 carbon atoms; R 2 is a hydrogen atom or a monovalent hydrocarbon group having 1 to 6 carbon atoms; x and z are positive numbers; y is zero or a positive number; and x, y, and z have values such that their ratios are 0.3≦(x+y)/z≦4; and zero≦y/x≦100, said method comprising cohydrolysis or condensation reactions of (A) hydrolyzable group-containing organosilane as represented by the following general formula ##STR25## in which R 1 as defined as above, and M is a hydrolyzable group or (A') disiloxane as represented by the following general formula ##STR26## in which R 1 is defined as above, (B) hydrolyzable group-containing organosilane as represented by the following general formula ##STR27## in which R 1 , R 2 , and M are defined as above or (B') disiloxane as represented by the following general formula ##STR28## and (C) hydrolyzable silane as represented by the following general formula SiM.sub.4 M in the formula is defined as above.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1994-04-29 | 1994-10-29 | 1995-04-30 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1998-04-29 | 1998-10-29 | 1999-04-30 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2002-04-29 | 2002-10-29 | 2003-04-30 | $7700.00 | Window Closed / Lapsed |