US3944587A
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Hydroxypolyfluoroalkyl-containing silane derivatives and manufacturing the same
Assignee: Daikin Industries Ltd
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Filing: 1974-04-10
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Granted: 1976-03-16
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Expires: 1994-04-10
Abstract
Abstract A hydroxypolyfluoroalkyl-containing silane derivative having the formula NHp-(R2-NHq)r-R4--SiXx ¦¦¦ ¦¦Zz R12-pR31-qy-z WHEREIN EACH OF R1 and R3 is alkyl; each of R2 and R4 is alkylene; X is alkoxyl, alkyl, hydroxy, chlorine or hydrogen and at least one of the groups represented by X is alkoxyl, hydroxy, chlorine or hydrogen; p is 0 to 2, q is 0 or 1, r is 0 to 5, y is 1 or 2 and x is 2 or 3, provided that the sum of p and qr is at least 1 and the sum of x and y is 4; z is 1 or 2 and is equal to or less than y; and Z is a group represented by Rp5R6 ¦¦ N-(R2-N)r-R4- ¦¦ R12-pR31-q WHEREIN R1, R2, R3, R4, p, q and r are the same as above and each of R5 and R6 is a hydrogen or OH ¦ RfCH2CHCH2- and at least one of the groups represented by R5 and R6 is OH ¦ RfCH2CHCH2-, Rf being a perfluoroalkyl group: the above compound being useful as water- and oil-repellent agent.
Inventors
- 👤 Atsuo Katsushima
- 👤 Shinichi Imazu
- 👤 Shoshin Fukui
- 👤 Akitoshi Iwatani
- 👤 Tadashi Akazawa
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-02 10:11
CPC Classifications
C; C09; C09D; C09D4/00; C07; C07F; C07F7/00; C07F7/02; C07F7/08; C07F7/18; C07F7/1804
Claims Analysis
Total Claims: 16
Claim 1
Independent Claim
276 words
A hydroxypolyfluoroalkyl-containing silane derivative having the formula ##EQU40## wherein each of R 1 and R 3 is an alkyl group having 1 to 5 carbon atoms; each of R 2 and R 4 is an alkylene group having 1 to 5 carbon atoms; X is an alkoxyl group having 1 to 5 carbon atoms, alkyl group having 1 to 5 carbon atoms, hydroxyl group, chlorine atom or hydrogen atom and at least one of the groups represented by X is an alkoxyl group having 1 to 5 carbon atoms, hydroxyl group, chlorine atom or hydrogen atom; p is zero or an integer of 1 or 2, q is zero or an integer of 1, r is zero or an integer of 1 to 5, y is an integer of 1 or 2 and x is an integer of 2 or 3, provided that the sum of p and qr is at least 1 and the sum of x and y is 4; z is an integer of 1 or 2 equal to or less than that represented by y; and Z is a group represented by ##EQU41## wherein R 1 , R 2 , R 3 , R 4 , p, q and r are the same as defined above and each of R 5 and R 6 is a hydrogen atom or ##EQU42## and at least one of the groups represented by R 5 and R 6 is ##EQU43## R f being a perfluoroalkyl group having 3 to 21 carbon atoms; each of said R 2 , R 4 , R 5 , R 6 and X being different or same when plural in number.
Claim 2
Dependent Claim
276 words
A hydroxypolyfluoroalkyl-containing silane derivative having the formula ##EQU40## wherein each of R 1 and R 3 is an alkyl group having 1 to 5 carbon atoms; each of R 2 and R 4 is an alkylene group having 1 to 5 carbon atoms; X is an alkoxyl group having 1 to 5 carbon atoms, alkyl group having 1 to 5 carbon atoms, hydroxyl group, chlorine atom or hydrogen atom and at least one of the groups represented by X is an alkoxyl group having 1 to 5 carbon atoms, hydroxyl group, chlorine atom or hydrogen atom; p is zero or an integer of 1 or 2, q is zero or an integer of 1, r is zero or an integer of 1 to 5, y is an integer of 1 or 2 and x is an integer of 2 or 3, provided that the sum of p and qr is at least 1 and the sum of x and y is 4; z is an integer of 1 or 2 equal to or less than that represented by y; and Z is a group represented by ##EQU41## wherein R 1 , R 2 , R 3 , R 4 , p, q and r are the same as defined above and each of R 5 and R 6 is a hydrogen atom or ##EQU42## and at least one of the groups represented by R 5 and R 6 is ##EQU43## R f being a perfluoroalkyl group having 3 to 21 carbon atoms; each of said R 2 , R 4 , R 5 , R 6 and X being different or same when plural in number.
Claim 3
Dependent Claim
168 words
The hydroxypolyfluoroalkyl-containing silane derivative having the formula ##EQU44## wherein each of R 2 and R 4 is an alkylene group having 1 to 5 carbon atoms; X' is an alkoxyl group having 1 to 5 carbon atoms or alkyl group having 1 to 5 carbon atoms and at least one of the groups represented by X' is an alkoxyl group having 1 to 5 carbon atoms; r is zero or an integer of 1 to 5, y is an integer of 1 or 2 and x is an integer of 2 or 3, provided that the sum of x and y is 4; z is an integer of 1 or 2 equal to or less than that represented by y; and each of R 5 , R 6 and R 7 is a hydrogen atom or ##EQU45## and at least one of the groups represented by R 5 , R 6 and R 7 is ##EQU46## R f being a perfluoroalkyl group having 3 to 21 carbon atoms.
Claim 4
Dependent Claim
168 words
The hydroxypolyfluoroalkyl-containing silane derivative having the formula ##EQU44## wherein each of R 2 and R 4 is an alkylene group having 1 to 5 carbon atoms; X' is an alkoxyl group having 1 to 5 carbon atoms or alkyl group having 1 to 5 carbon atoms and at least one of the groups represented by X' is an alkoxyl group having 1 to 5 carbon atoms; r is zero or an integer of 1 to 5, y is an integer of 1 or 2 and x is an integer of 2 or 3, provided that the sum of x and y is 4; z is an integer of 1 or 2 equal to or less than that represented by y; and each of R 5 , R 6 and R 7 is a hydrogen atom or ##EQU45## and at least one of the groups represented by R 5 , R 6 and R 7 is ##EQU46## R f being a perfluoroalkyl group having 3 to 21 carbon atoms.
Claim 5
Dependent Claim
46 words
The hydroxypolyfluoroalkyl-containing silane derivative according to claim 2, in which at least one of the groups represented by said R 5 and R 7 is ##EQU47## R f being a perfluoroalkyl group having 3 to 21 carbon atoms, and said R 6 is a hydrogen atom.
Claim 6
Dependent Claim
27 words
The hydroxypolyfluoroalkyl-containing silane derivative according to claim 2, in which said x is an integer of 3 and y and z are each an integer of 1.
Claim 7
Dependent Claim
33 words
The hydroxypolyfluoroalkyl-containing silane derivative according to claim 2, in which said R 2 is --(CH 2 ) 2 -- and said R 4 is an alkylene group having 3 to 5 carbon atoms.
Claim 8
Dependent Claim
23 words
The hydroxypolyfluoroalkyl-containing silane derivative according to claim 2, in which said R f is a perfluoroalkyl group having 9 to 17 carbon atoms.
Claim 9
Dependent Claim
213 words
A process for producing a hydroxypolyfluoroalkyl-containing silane derivative, which comprises reacting a perfluoroalkylpropylene epoxide having the formula ##EQU48## wherein R f is a perfluoroalkyl group having 3 to 21 carbon atoms with an aminoalkyl silane derivative having the formula ##EQU49## wherein each of R 1 and R 3 is an alkyl group having 1 to 5 carbon atoms; each of R 2 and R 4 is an alkylene group having 1 to 5 carbon atoms; X is an alkoxyl group having 1 to 5 carbon atoms, alkyl group having 1 to 5 carbon atoms, hydroxyl group, chlorine atom or hydrogen atom and at least one of the groups represented by X is an alkoxyl group having 1 to 5 carbon atoms, hydroxyl group, chlorine atom or hydrogen atom; and p is zero or an integer of 1 or 2, q is zero or an integer of 1, r is zero or an integer of 1 to 5, y is an integer of 1 or 2 and x is an integer of 2 or 3, provided that the sum of p and qr is at least 1 and the sum of x and y is 4; each of said R 2 , R 4 and X being different or same when plural in number.
Claim 10
Dependent Claim
213 words
A process for producing a hydroxypolyfluoroalkyl-containing silane derivative, which comprises reacting a perfluoroalkylpropylene epoxide having the formula ##EQU48## wherein R f is a perfluoroalkyl group having 3 to 21 carbon atoms with an aminoalkyl silane derivative having the formula ##EQU49## wherein each of R 1 and R 3 is an alkyl group having 1 to 5 carbon atoms; each of R 2 and R 4 is an alkylene group having 1 to 5 carbon atoms; X is an alkoxyl group having 1 to 5 carbon atoms, alkyl group having 1 to 5 carbon atoms, hydroxyl group, chlorine atom or hydrogen atom and at least one of the groups represented by X is an alkoxyl group having 1 to 5 carbon atoms, hydroxyl group, chlorine atom or hydrogen atom; and p is zero or an integer of 1 or 2, q is zero or an integer of 1, r is zero or an integer of 1 to 5, y is an integer of 1 or 2 and x is an integer of 2 or 3, provided that the sum of p and qr is at least 1 and the sum of x and y is 4; each of said R 2 , R 4 and X being different or same when plural in number.
Claim 11
Dependent Claim
24 words
The process according to claim 7, in which said R f of the epoxide is a perfluoroalkyl group having 9 to 17 carbon atoms.
Claim 12
Dependent Claim
20 words
The process according to claim 7, in which said epoxide is one species selected from the group consisting of ##EQU50##
Claim 13
Dependent Claim
117 words
The process according to claim 7, in which said amino-alkyl silane derivative has the formula [NH.sub.2 --(R.sup.2 --NH).sub.r --R.sup.4 ].sub.y SiX'.sub.x wherein each of R 2 and R 4 is an alkylene group having 1 to 5 carbon atoms; X' is an alkoxyl group having 1 to 5 carbon atoms or an alkyl group having 1 to 5 carbon atoms and at least one of the groups represented by X' is an alkoxy group having 1 to 5 carbon atoms; r is zero or an integer of 1 to 5, y is an integer of 1 or 2 and x is an integer of 2 or 3, provided that the sum of x and y is 4.
Claim 14
Dependent Claim
22 words
The process according to claim 10, in which said x is an integer of 3 and y is an integer of 1.
Claim 15
Dependent Claim
30 words
The process according to claim 10, in which said R 2 is --(CH 2 ) 2 -- and R 4 is an alkylene group having 3 to 5 carbon atoms.
Claim 16
Dependent Claim
50 words
The process according to claim 7, in which said aminoalkyl silane derivative is one species selected from the group consisting of H.sub.2 N(CH.sub.2 CH.sub.2 NH).sub.2 (CH.sub.2).sub.3 Si(OCH.sub.3).sub.3, h.sub.2 n(ch.sub.2 ch.sub.2 nh).sub.3 (ch.sub.2).sub.3 si(OCH.sub.3).sub.3, h.sub.2 n(ch.sub.2 ch.sub.2 nh).sub.4 (ch.sub.2).sub.3 si(OCH.sub.3).sub.3, h.sub.2 n(ch.sub.2 ch.sub.2 nh).sub.5 (cn.sub.2).sub.3 si(OHC.sub.3).sub.3 and H.sub.2 N(CH.sub.2).sub.2 NH(CH.sub.2).sub.3 Si(OCH.sub.3).sub.3.
References Cited (Backward Citations)
US3317577A
Cited
US3560543A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1979-03-16 | 1979-09-15 | 1980-03-16 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1983-03-16 | 1983-09-15 | 1984-03-16 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1987-03-16 | 1987-09-15 | 1988-03-16 | $7700.00 | Window Closed / Lapsed |