ADHESIVE CHEMISTRY DEVELOPMENTS AND TRENDS

POLYMER SCIENCE AND TECHNOLOGY

Editorial Board: William J. Bailey, University of Maryland, College Park, Maryland J. P. Berry, Rubber and Plastics Research Association of Great Britain,

Shawbury, Shrewsbury, England A. T. DiBenedetto, The University of Connecticut, Storrs, Connecticut C. A. J. Hoeve, Texas A & M University, College Station, Texas Yoichi Ishida, Osaka University, Toyonaka, Osaka, Japan Frank E. Karasz, University of Massachusetts Amherst, Massachusetts Oslas Solomon, Franklin Institute, Philadelphia, Pennsylvania

Recent volumes in the series:

Volume 16 POLYMERIC SEPARATION MEDIA Edited by Anthony R. Cooper

Volume 17 POLYMER APPLICATIONS OF RENEWABLE-RESOURCE MATERIALS Edited by Charles E. Carraher, Jr., and L. H. Sperling

Volume 18 REACTION INJECTION MOLDING AND FAST POLYMERIZATION REACTIONS Edited by Jiri E. Kresta

Volume 19 COORDINATION POLYMERIZATION Edited by Charles C. Price and Edwin J. Vandenberg

Volume 20 POLYMER ALLOYS III: Blends, Blocks, Grafts, and Interpenetrating Networks Edited by Daniel Klempner and Kurt C. Frisch

Volume 21 MODIFICATION OF POLYMERS Edited by Charles E. Carraher, Jr., and James A. Moore

Volume 22 STRUCTURE PROPERTY RELATIONSHIPS OF POLYMERIC SOLIDS Edited by Anne Hiltner

Volume 23 POLYMERS IN MEDICINE: Biomedical and Pharmacological Applications Edited by Emo Chiellini and Paolo Giusti

Volume 24 CROWN ETHERS AND PHASE TRANSFER CATALYSIS IN POLYMER SCIENCE Edited by Lon J. Mathias and Charles E. Carraher, Jr.

Volume 25 NEW MONOMERS AND POLYMERS Edited by Bill M. Culbertson and Charles U. Pittman, Jr.

Volume 26 POLYMER ADDITIVES Edited by Jiri E. Kresta

Volume 27 MOLECULAR CHARACTERIZATION OF COMPOSITE INTERFACES Edited by Hatsuo Ishida and Ganesh Kumar

Volume 28 POLYMERIC LIQUID CRYSTALS Edited by Alexandre Blumstein

Volume 29 ADHESIVE CHEMISTRY: Developments and Trends Edited by Lieng-Huang Lee

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ADHESIVE CHEMISTRY DEVELOPMENTS AND TRENDS

EDITED BY

LIENG-HUANG LEE Webster Research Center Xerox Corporation Webster, New York

PLENUM PRESS • NEW YORK AND LONDON

library of Congress Cataloging in Publication Data

Symposium on Recent Developments in Adhesive Chemistry (1983: Seattle, Wash.) Adhesive chemistry, developments and trends.

(Polymer science and technology; v. 29) "Proceedings of a Symposium on Recent Developments in Adhesive Chemistry, held

March 21-23, 1983, in Seattle, Washington"-T.p. verso. Includes bibliographies and indexes. 1. Adhesives-Congresses. I. Lee, lieng-Huang, 1924- . II. Title. V. Series.

TP967.S96 1983 668'.3 84-24977

ISBN-13: 978-1-4612-9481-8

DOl: 10.1007/978-1-4613-2435-5

e-ISBN-13: 978-1-4613-2435-5

Proceedings of a symposium on Recent Developments in Adhesive Chemistry, sponsored by the Division of Organic Coatings and Plastics Chemistry of the American Chemical Society, held March 21-23, 1983, in Seattle, Washington

© 1984 Plenum Press, New York

Softcover reprint of the hardcover 1 st edition 1984

A Division of Plenum Publishing Corporation 233 Spring Street, New York, N.Y. 10013

All rights reserved

No part of this book may be reproduced, stored in a retrieval system, or transmitted in any form or by any means, electronic, mechanical, photocopying, microfilming, recording, or otherwise, without written permission from the Publisher

PREFACE

Since the first symposium on Recent Advances in Adhesion, held September, 1971 in Washington, D.C., this Division of the American Chemical Society has continuously sponsored several symposia on adhesion and adhesives. The chemists have gradually realized the importance of adhesion in various fields of science and technology. During these years, the science of adhesion has steadily grown along with progress in surface science and fracture mechanics. Moreover, new adhesives have been invented and applied in actual structures, for example, structural and aerospace adhesives.

In response to socio-economic demands, new forms of adhesives have been introduced to combat the problems of pollution and to promote energy-conservation. The developments of hot-melt adhesives, waterborne adhesives, and radiation-curable adhesives are vivid examples of successes in solving some of the problems. As chemists, our hatural desire is to understand how those new adhesives and new forms of adhesives are made. Thus, we are interested in learning about the chemistry of adhesives so that we may create new generations of materials to satisfy future needs. It was based on this common interest that w~ set forth to org'anize this Symposium on Recent Developments in Adhesive Chemistry. It was held from March 21 through 23, 1983 in the Westin Hotel, Seattle, Washington. The Symposium was very well attended. As a matter of fact, for the first two sessions, we had to move from the smaller Mt. St. Helen Room to the larger Grand Ballroom, not because of superstition, but because of sheer necessity to accommo­date a larger than expected attendance.

v

vi PREFACE

As a record of this successful Conference, all papers (after revision) presented to the Symposium and the discussions during the meeting are now published in these Proceedings. In addition, the contributions shortly after the Conference in projecting future trends of adhesive research are also included. As a result, the new title for the volume becomes "Adhesive Chemistry - Developments and Trends." The six parts following the or ig inal order of the Conference are:

I. Chemistry of Adhesion - The Importance of Interface

II. Physics of Adhesion - Characterization of Surface and Bulk of Adhesive Systems

III. Radiation-curable Adhesives

IV. High Temperature Adhesives

V. Anaerobic and Structural Adhesives

VI. Trends in Adhesive Research

As Chairman of the Symposium, I would like to take this opportunity to thank our contributors~ their names and biographies are at the end of this volume. And, I thank Session Chairmen: Dr. L. H. Sharpe, Dr. V. D. McGinniss, Dr. K. C. Stueben, and Professor J. P. Wightman. I sincerely appreciate the skill and patience of Ms. Jeraldine T. Allen and Ms. Nancy MacDonald in typing the entire Proceedings in a camera-ready format.

Acknowledgement is also made to the donors of the Petroleum Research Fund, administered by the Amer ican Chemical Society, for their partial support of this Symposium.

Lieng-Huang Lee June, 1984

CONTENTS

PART ONE: Chemistry of Adhesion -The Importance of Interface

Introductory Remarks

LIENG-HUANG LEE

Recent Developments in Adhesive and Sealant Chemistry

LIENG-HUANG LEE

Overview of Adherence Phenomena

DANIEL MAUGIS

An Analytical Method for Determining the

3

5

63

Surface Energy of Solid Polymers 95

MICHAEL C. H. LEE

Effect of Amine Surface Treatment on the Adhe s ion of a Polyu rethane to the Sur face 121

FASI LIANG AND PATRICIA DREYFUSS

Effect of Silane on Glass/Resin Adhesion Strength 139

YONA ECKSTEIN AND ELISABETH J. BERGER

Discussion 165

PART TWO: Physics of Adhesion -Characterization of Surface and Bulk of Adhesive Systems

vii

viii

Introductory Remarks L. H. SHARPE

New Applications of ESCA

D. BRIGGS

Fracto-Emission Accompanying Adhesive Failure

J. T. DICKINSON

Monitoring Epoxy Cure Kinetics with a Viscosity-Dependent Fluorescent Probe

R. L. LEVY AND D. P. AMES

Dynamic Mechanical Properties of Silicone Pressure Sensitive Adhesives

B. C. COPLEY

The Viscoelastic Properties of Pressure­Sensitive Adhesives

J. B. CLASS AND S. G. CHU

Block Copolymer Adhesive Stu'dies

T. C. WARD, ANNE WOOD BRINKLEY, MARGARET SHERIDAN AND PAUL KONING

Discussion

PART THREE: Radiation-Curable Adhesives

Introductory Remarks

V. D. McGINNISS

Ultraviolet Cured Pressure-Sensitive Adhesives

KENNETH C. STUEBEN

Recent Progress in Photoinitiated Cationic Polymerization

JAMES V. CRIVELLO

Polymer and Formulation Design Characteristics for Developing Bonding Capabilities of Radiation-Curable Coatings and Adhesive Systems

VINCENT D. McGINNISS

CONTENTS

171

175

193

245

257

269

297

311

317

319

351

363

CONTENTS

Dynamic Thermal Analysis Characterizations of Electron-Beam Cured Adhesives

F. J. CAMPBELL

Reactive Butadiene/Acrylonitrile Liquid and Solid Elastomers: Formulating Acrylic, Anaerobic, and Radiation-Curable Adhesives

R. S. DRAKE AND A. R. SIEBERT

Photoinitiators: A Review of Mechanisms and Applications

L. R. GATECHAIR AND D. WOSTRATZKY

ix

379

393

409

Discussion 439

PART FOUR: High Temperature Adhesives

Introductory Remarks

K. C. STUEBEN

Status of High Temperature Adhesives

P. M. HERGENROTHER

Polyimide Adhesives: Modified with ATBN

445

447

and Silicone Elastomers 467

ANNE K. ST. CLAIR, TERRY L. ST. CLAIR AND STEPHEN A. EZZELL

The Application of Thermodynamic and Spectroscopic Techniques to Adhesion in the Polyimide/Ti 6-4 and Polyphenyl­quinoxaline/Ti 6-4 Systems

S. DIAS AND J. P. WIGHTMAN

Evaluation of High Temperature Structural Adhesives for Extended Service

C. L. HENDRICKS AND S. G. HILL

Aminosilane and Metal Modifications of Polyimide Surfaces

H. J. LEARY, JR. AND D. S. CAMPBELL

481

489

517

x

Influence of Molecular Weight on Fracture Behavior of Polyphenylquinoxaline Thermosets

T. E. HELMINIAK AND W. B. JONES

Discussion

PART FIVE: Anaerobic and Structural Adhesives

Introductory Remarks

JAMES P. WIGHTMAN

Some Recent Developments in Scanning Electron Microscopy

R. BUCHANAN

Potential Anaerobic and Structural Acrylic Modified Polyester Adhesives

R. A. PIKE AND F. P. LAMM

Anaerobic Adhesives Containing Maleimides Having Improved Thermal Resistance

L. J. BACCEI AND B. M. MALOFSKY

Chemistry of Accelerators for Curing Anaerobic Adhesives - Reaction of N,N-Dimethylaniline Derivatives with Cumene Hydroperoxide

R. W. R. HUMPHREYS

Chemistry, Physical Properties and Durability of Structural Adhesive Bonds

A. V. POCIUS, D. A. WANGSNESS, C. J. ALMER AND A. G. McKOWN

Reactive Butadiene/Acrylonitrile Liquid and Solid Elastomers: A Bibliography for Formulating Epoxy Structured Adhesives

R. S. DRAKE AND A. R. SIEBERT

CONTENTS

525

533

539

543

575

589

603

617

643

CONTENTS

A Low Curing Temperature CTBN-Toughened Epoxy Adhesive

NIE XUZONG, WANG LIJIAN, XUE RUILAN, LI YIMING, AND YU YUNCHAO

Summarizing Remarks

JAMES P. WIGHTMAN

Discussion

PART SIX: Trends in Adhesive Research

Developments in and Limitations of Adhesive Materials for Severe Environments and a Long Service Life

LIENG-HUANG LEE

Elastomers and Resin Modifiers for Water-Base Adhesives

MARLENE J. JONES

"Aerobic" Acrylic Adhesives--New Technology in Acrylic Adhesives

ANDREW G. BACHMANN

Radiant Energy Curable Adhesives

CLAIRE BLUESTEIN

Isocyanatoethyl Methacrylate: A Latent Cross linker for Coating Adhesive Resins

PAUL E. CRANLEY

Moisture Permeation of Polymer Sealants

xi

655

665

667

675

693

725

753

765

and Interface Modifying Films 785

BONNIE L. RATHBUN AND PHILIPP who SCHUESSLER

ESCA and AES Studies of the Interfacial Chemical Bonding between Aluminum and Chromium (III) Fumarato­Coordination Compound

YANG QI-XIANG AND ZHOU QIN-LI 799

xii

Adhesive Research in China LIENG-HUANG LEE

Discussion

Contributors

Author Index

Subject Index

CONTENTS

821

833

835

845

857