Photocurable compositions

Patent metadata

Field	Value
Publication number	US-9217920-B2
Application number	US-201314409162-A
Country	US
Kind code	B2
Filing date	Aug 6, 2013
Priority date	Aug 9, 2012
Publication date	Dec 22, 2015
Grant date	Dec 22, 2015

Abstract

A photocurable composition comprising a photoresist component, and a perfluoropolyether silane is disclosed. The composition enables easier release of phototool from a photoresist.

First claim

What is claimed is:

1. A photocurable composition comprising:
a) a solder photoresist component, and
b) a perfluoropolyether silane of the formula:
(R PFPE —X 1 —CO—NH) x —R 1 —(NH—CO—X 2 —R Silyl ) y ,

where

R PFPE represents a perfluoropolyether group of the formula R PFPE *-Q where
R PFPE * is a monovalent perfluoropolyether group, and Q is a divalent alkylene group, said alkylene optionally containing one or more catenary (in-chain) nitrogen or oxygen atoms, and optionally containing one or more sulfonamide, carboxamido, or carboxy functional groups,
X 1 and X 2 are independently —O—, —S— or —NR 2 — where R 2 is H or C 1 -C 4 alkyl,
R 1 is a residue of a polyisocyanate,
R Silyl is a silane group-containing moiety containing one or more silyl groups,
subscripts x and y are each independently 1 to 6, and

c) a free-radical photoinitiator.

2. The photocurable composition of claim 1 , comprising 0.1 to 5 parts by weight of the perfluoropolyether silane compound relative to 100 parts by weight of the photoresist component.

3. The photocurable composition of claim 1 wherein the perfluoropolyether group, R PFPE , is of the formula:
R f 1 —O—R f 2 —(R f 3 ) q —, wherein R f 1 represents a perfluoroalkyl group, R f 2 represents a C 1 -C 4 perfluoroalkyleneoxy groups or a mixture thereof, R f 3 represents a perfluorinated alkylene group and q is 0 to 1.

4. The fluorochemical urethane of claim 3 wherein R f 1 is a monovalent perfluoroalkyl group comprising one or more perfluorinated repeating units selected from the group consisting of —F—C n F 2n —, F—(CF(Z)—, F—(CF(Z)C n F 2n —, F—C n F 2n CF(Z)—, F—CF 2 CF(Z)—, and combinations thereof, wherein n is 1 to 4 and Z is a perfluoroalkyl group or a perfluoroalkoxy group.

5. The fluorochemical urethane of claim 1 wherein said perfluoropolyether group is selected from one or more of —(CF 2 —CF 2 —O) r —; —(CF(CF 3 )—CF 2 —O) s —; —(CF 2 CF 2 —O) r —(CF 2 O) t —, —(CF 2 CF 2 CF 2 CF 2 —O) u and —(CF 2 —CF 2 —O) r —(CF(CF 3 )—CF 2 —O) s —; wherein each of r, s, t and u are each integers of 1 to 50.

6. The photocurable composition of claim 1 , wherein R Silyl is of the formula
—R 4 —Si(Y) p (R 3 ) 3-p , where

R 4 is a divalent alkylene group, said alkylene groups optionally containing one or more catenary oxygen atoms; Y is a hydrolysable group, R 3 is a monovalent alkyl or aryl group, and p is 1, 2 or 3.

7. The photocurable composition of claim 6 , wherein the Y group is an alkoxy, acetoxy or halide group.

8. The photocurable composition of claim 1 , wherein R Silyl is a (meth)acrylate oligomer having pendent silyl groups.

9. The photocurable composition of claim 8 , wherein R Silyl is of the formula:
X-(M Silyl ) a -(M 2 ) b -S—R 4 —

wherein
X is H, or the residue of an initiator,
M Silyl is the residue of a (meth)acrylate monomer having a pendent silyl group,
M 2 is the residue of (meth)acrylate ester monomer,
R 4 is a divalent alkylene or arylene groups, or combinations thereof, said alkylene groups optionally containing one or more catenary oxygen atoms; and
a is at least 2, b may be 0 and a+b is 2-20.

10. The photocurable composition of claim 1 , wherein the equivalent ratio of R PFPE groups to R Silyl groups is 1:1 to 1:10.

11. The photocurable composition of claim 1 wherein R 1 is an alkylene group, and arylene group or combination thereof, having a valence of x+y.

12. The photocurable composition of claim 1 , wherein R Silyl is a silane-containing moiety derived from the Michael reaction between a nucleophilic acryloyl compound and an aminosilane.

13. The photocurable composition of claim 1 further comprising a thermoset resin in the amount from 5 to 40 parts by weight, based on 100 parts by weight of the photoresist component.

14. A multilayer article comprising
a) a metallic base substrate,
b) a phototool,
c) a layer of the photocurable composition of claim 1 disposed therebetween.

15. A multilayer article comprising
a) a printed circuit broad substrate,
b) a phototool,
c) a layer of the photocurable composition of claim 1 disposed therebetween.

16. The multilayer article of claim 15 , wherein the photocurable layer has been partially cured by heat and/or light exposure.

17. The multilayer article of claim 15 , further comprising a hardcoat disposed on the surface of the phototool.

18. The partially cured composition of claim 16 having release value less than 100 g/in (˜39 g/cm).

19. A multilayer article comprising
a) a printed circuit board substrate,
b) a layer of the photocurable composition of claim 1 on a surface of the substrate.

Assignees

• 3M Innovative Properties Co

Inventors

• Fall Douglas C
• Qiu Zai-Ming

Classifications

• B23K35/24 Primary

  Selection of soldering or welding materials proper (B23K35/34 takes precedence) · CPC title

• G03F7/0046

  with perfluoro compounds, e.g. for dry lithography (G03F7/0048 takes precedence) · CPC title

• H05K3/3452

  Solder masks · CPC title

• H05K3/287

  Photosensitive compositions · CPC title

• G03F7/0755

  Non-macromolecular compounds containing Si-O, Si-C or Si-N bonds (G03F7/0752 takes precedence) · CPC title