Antifouling treatment composition, treating apparatus, treating method and treated article

Patent metadata

Field	Value
Publication number	US-11149149-B2
Application number	US-201615565061-A
Country	US
Kind code	B2
Filing date	Apr 5, 2016
Priority date	Apr 10, 2015
Publication date	Oct 19, 2021
Grant date	Oct 19, 2021

Abstract

A surface-treating agent for a nitrided surface, including a fluorine-containing compound having a carbon-carbon unsaturated bond at its molecular terminal as a group of —Y-A wherein Y is a single bond, an oxygen atom or a divalent organic group, and A is —CH═CH 2 or —C≡CH. Also disclosed is an article treated with the surface-treating agent, a method for forming a surface-treating layer on a surface of a base material, a surface-treating layer forming apparatus, and a process for producing an article including a base material and a surface-treating layer coating a surface of the base material.

First claim

The invention claimed is:

1. A surface-treating agent for a nitrided surface, comprising a fluorine-containing compound having a carbon-carbon unsaturated bond at its molecular terminal as a group of —Y-A wherein Y is a single bond, an oxygen atom or a divalent organic group, and A is —CH═CH 2 or —C≡CH, wherein the fluorine-containing compound having a carbon-carbon unsaturated bond at its molecular terminal is at least one compound of any of the following formulae (A1), (A2), (C1), (C2), (E1) and (E2):
(Rf—PFPE) γ′ —X 4 —(SiR a k R b l R c m R d n ) γ   (C1)

(R d n R c m R b l R a k Si) γ —X 4 —PFPE-X 4 —(SiR a k R b l R c m R d n ) γ   (C2)

(Rf—PFPE) ε′ —X 7 —(CR a2 k2 R b2 l2 R c2 m2 R d2 n2 ) ε   (E1)

(R d2 n2 R c2 m2 R b2 l2 R a2 k2 C) ε —X 7 —PFPE-X 7 —(CR a2 k2 R b2 l2 R c2 m2 R d2 n2 ) ε   (E2)

wherein:
A is each independently at each occurrence —CH═CH 2 or —C≡CH;
Y is each independently at each occurrence a single bond, an oxygen atom or a divalent organic group;
Rf is each independently an alkyl group having 1-16 carbon atoms which may be substituted by one or more fluorine atoms;
PFPE is each independently —(OC 4 F 8 ) a —(OC 3 F 6 ) b —(OC 2 F 4 ) c —(OCF 2 ) d —, wherein a, b, c and d are each independently an integer of 0 or more and 200 or less, the sum of a, b, c and d is 1 or more, and the occurrence order of the respective repeating units in parentheses with the subscript a, b, c or d is not limited in the formula;
R 11 is each independently a hydrogen atom or a halogen atom;
R 12 is each independently at each occurrence a hydrogen atom or a lower alkyl group;
X 1 is each independently a single bond or a 2-10 valent organic group;
X 2 is each independently at each occurrence a single bond or a divalent organic group;
t is each independently an integer of 2-10;
α is each independently an integer of 1-9;
α′ is each independently an integer of 1-9;
X 4 is each independently a single bond or a 2-10 valent organic group;
γ is each independently an integer of 1-9;
γ′ is each independently an integer of 1-9;
R a is each independently at each occurrence —Z—SiR 71 p R 72 q R 73 r R 74 s ;
Z is each independently at each occurrence an oxygen atom or a divalent organic group;
R 71 is each independently at each occurrence R a′ ;
R a′ has the same definition as that of R a ;
in R a , the number of Si atoms which are straightly linked via the Z group is up to five;
R 72 is each independently at each occurrence —X 5 —Y-A;
X 5 is each independently at each occurrence a single bond or a divalent organic group;
R 73 is each independently at each occurrence a hydroxyl group or a hydrolyzable group;
R 74 is each independently at each occurrence a hydrogen atom or a lower alkyl group;
p is each independently at each occurrence an integer of 0-3;
q is each independently at each occurrence an integer of 0-3;
r is each independently at each occurrence an integer of 0-3;
s is each independently at each occurrence an integer of 0-3;
with the proviso that (p+q+r+s) is 3;
R b is each independently at each occurrence —X 5 —Y-A;
R c is each independently at each occurrence a hydroxyl group or a hydrolyzable group;
R d is each independently at each occurrence a hydrogen atom or a lower alkyl group;
k is each independently at each occurrence an integer of 0-3;
l is each independently at each occurrence an integer of 2-3;
m is each independently at each occurrence an integer of 0-3;
n is each independently at each occurrence an integer of 0-3;
with the proviso that (k+l+m+n) is 3, and there is at least one the Y-A group in —(SiR a k R b l R c m R d n ) r ;
X 7 is each independently, a single bond or a divalent organic group;
ε is each independently an integer of 1-9;
ε′ is each independently an integer of 1-9;
R a2 is each independently at each occurrence, —Z 2 —CR 75 p2 R 76 q2 R 77 r2 R 78 s2 ;
Z 2 is each independently at each occurrence, an oxygen atom or a divalent organic group;
R 75 is each independently at each occurrence, R a2′ ;
R a2′ has the same definition as that of R a2 ;
in R a2 , the number of C atoms which are straightly linked via the Z group is up to five;
R 76 is each independently at each occurrence, —X 8 —Y-A;
X 8 is each independently at each occurrence, a single bond or a divalent organic group;
R 77 is each independently at each occurrence, a hydroxyl group or a hydrolyzable group;
R 78 is each independently at each occurrence, a hydrogen atom or a lower alkyl group;
p2 is each independently at each occurrence, an integer of 0-3;
q2 is each independently at each occurrence, an integer of 0-3;
r2 is each independently at each occurrence, an integer of 0-3;
s2 is each independently at each occurrence, an integer of 0-3;
with the proviso that (p2+q2+r2+s2) is 3;
R b2 is each independently at each occurrence, —X 8 —Y-A;
R c2 is each independently at each occurrence, a hydroxyl group or a hydrolyzable group;
R d2 is each independently at each occurrence, a hydrogen atom or a lower alkyl group;
k2 is each independently at each occurrence, an integer of 0-3;
l2 is each independently at each occurrence, an integer of 2-3;
m2 is each independently at each occurrence, an integer of 0-3; and
n2 is each independently at each occurrence, an integer of 0-3;
with the proviso that (k2+l2+m2+n2) is 3, and there is at least one the Y-A group in —(CR a2 k2 R b2 l2 R c2 m2 R d2 n2 ) ε .

2. The surface-treating agent for a nitrided surface according to claim 1 wherein A is —CH═CH 2 .

3. The surface-treating agent for a nitrided surface according to claim 1 wherein Y is a single bond, an oxygen atom or —CR 14 2 —, and
R 14 is a hydrogen atom or a lower alkyl group.

4. The surface-treating agent for a nitrided surface according to claim 1 wherein Rf is a perfluoroalkyl group having 1-16 carbon atoms.

5. The surface-treating agent for a nitrided surface according to claim 1 wherein
PFPE is a group of any of the following formulae (a)-(c):
—(OC 3 F 6 ) b —  (a)

in the formula (a), b is an integer of 1 or more and 200 or less;
—(OC 4 F 8 ) a —(OC 3 F 6 ) b —(OC 2 F 4 ) c —(OCF 2 ) d —  (b)

in the formula (b), a and b is each independently an integer of 0 or more and 30 or less, c and d is each independently an integer of 1 or more and 200 or less, the sum of a, b, c and d is an integer of 10 or more and 200 or less, and the occurrence order of the respective repeating units in parentheses with the subscript a, b, c or d is not limited in the formula, and
—(OC 2 F 4 —R 15 ) n″ —  (c)

in the formula (c), R 15 is each independently a group selected from OC 2 F 4 , OC 3 F 6 and OC 4 F 8 , and n″ is an integer of 2-100.

6. The surface-treating agent for a nitrided surface according to claim 1 wherein
in PFPE:
OC 4 F 8 is OCF 2 CF 2 CF 2 CF 2 ,
OC 3 F 6 is OCF 2 CF 2 CF 2 , and
OC 2 F 4 is OCF 2 CF 2 .

7. The surface-treating agent for a nitrided surface according to claim 1 wherein
X 2 is —(CH 2 ) u —, and
u is an integer of 0-2.

8. The surface-treating agent for a nitrided surface according to claim 1 wherein the fluorine-containing compound having a carbon-carbon unsaturated bond at its molecular terminal is at least one compound of any of the formulae (A1) and (A2).

9. The surface-treating agent for a nitrided surface according to claim 1 wherein the fluorine-containing compound having a carbon-carbon unsaturated bond at its molecular terminal is at least one compound of any of the formulae (C1) and (C2).

10. The surface-treatin

Assignees

• Daikin Ind Ltd

Inventors

• Itami Yasuo
• Fuse Takashi
• Okkotsu Madoka
• Kinoshita Hidetoshi
• FUKASAWA Tatsuya

Classifications

• B05D2350/63

  ceramic layer · CPC title

• B05D2203/35

  Glass · CPC title

• B05D5/083

  involving the use of fluoropolymers · CPC title

• B05D1/60

  Deposition of organic layers from vapour phase (vapour phase deposition in general C23C14/00, C23C16/00) · CPC title

• C03C2217/78

  Coatings specially designed to be durable, e.g. scratch-resistant · CPC title